Right now, the primary reason seems to be philosophical. Bringing together alumni and annual giving teams points to a belief that small-dollar giving is just another way to engage. Philanthropy as one of the four CASE modes for alumni engagement reinforces that paradigm. Another dynamic at play is limited staffing resources, so combining these units under a single senior leader is economical.

More often than not, however, the alignment isn’t strategic. These units aren’t brought together in a way that includes ongoing consideration of how to grow and maintain a pipeline by creating robust donor journeys. Instead, both units run their own programs. Annual giving runs the giving campaigns, creates and delivers a set of fundraising appeals, and manages a Digital Experience Officer or student-caller program. Alumni teams manage boards, run chapters and groups, and execute large on-campus events.

The exception is usually Giving Day and reunions. These two specific, signature initiatives bring teams together almost year-round. Creating fun, memorable experiences that drive fundraising success requires the continuous coordination and layered strategies that only a cross-team collaborative approach can deliver. Giving Day and reunions are when the alumni engagement and annual giving merger comes to life.

But what would it be like if the AE/AG alignment wasn’t just about the success of two programs with everything else operating independently, but rather the units actually shared the same goals?

A truly integrated approach between the two units presents an extraordinary opportunity to build a culture that positions generosity, displayed through both time and treasure, as the primary strategic objective. Key ingredients for shared goals include using enhanced engagement metrics, sharing a joint calendar, and, most importantly, working together on next steps in the journey for a cohort of unassigned donors.

The Same Scorecard

To fully integrate AE/AG teams, education organizations must produce metrics that can segment donors by engagement level. The first step is to track activity, the second is to calculate engagement scores, and the final step is to produce segments that both teams understand as the target for dedicated resources.

(Altered data from private liberal arts college built and presented as a CMAC Engagement Constellation Report by my colleague, Melissa Schipke)

With segments defined by levels of engagement, AE and AG teams can work together to move a percentage of the 9,480 Moderately engaged stakeholders into the Highly engaged category, for example. With both AE and AG teams focused together on building journeys from segments established by engagement metrics, we can get much closer to offering personalized next steps to each individual.

In a recent Keynote, Almabase’s Kalyan Varma talked about the potential of combining engagement metrics with AI to enable this dynamic of sorting through engagement signals and providing next steps. It’s happening in leading non-profits like the Heritage Foundation. It can be done in higher ed.

The War Room, All Year

When alumni engagement and annual giving teams come together, it’s usually about program execution, but not shared goals. Even for a day of giving or reunion, the teams have separate goals. One is responsible for direct dollar conversions; the other is responsible for event registrations.

For annual giving and alumni teams to function as one, they need regular dialogue that enables “air traffic control.” These individuals, now working as one team to move moderately engaged alumni and friends to a highly engaged status, must coordinate next steps so they don’t bump into each other and create a negative donor experience. This is like having the Giving Day “War Room” but on a regular cadence throughout the year.

One Continuous Invitation

Another opportunity is to design a series of interconnected experiences that all contain messaging about generosity and opportunities to get more deeply involved across the four CASE modes. Every event includes an on-ramp to be more generous, including opportunities to give time or treasure. When people make a gift, they’re then introduced to another opportunity to volunteer or participate in some way. Again, this brings to life a cohesive strategy for involvement over a lifetime, rather than two units trying to coordinate different conversions.

Habits that Radiate

The big hurdle is the historical scope of traditionally separate teams. Alumni teams traditionally work to engage an entire community of graduates with non-giving opportunities. In contrast, annual giving teams focus more on donor retention and converting gifts from donor segments like LYBUNTS (Last-Year-But-Unfortunately-Not-This-Year) and SYBUNTS (Some-Years-But-Unfortunately-Not-This-Year).

This week, I spoke with my friend Dr. Jay Dillon at Cal Berkeley. We were prepping for his upcoming Faculty-in-Residence on his research into Alumni Identity. During the discussion, Jay mentioned the idea that we want generosity to “radiate” outward from individuals and segments of alumni over a lifetime. I love this phrasing. The problem is that without a new paradigm that means approaching alumni engagement and annual giving as really one endeavor designed to stimulate generosity, the future returns just won’t be there.

About Speaking Engagement

I selected three books for a potential next read for our Book Club and we had a members vote. I’m pleased to report we have a clear WINNER! Starting (officially) on Nov. 16 and ending after the holiday break on January 15, we’re going to read:

Flourish: The Art of Building Meaning, Joy, and Fulfillment — Daniel Coyle (2026)

From the author of The Culture Code, Flourish looks at wildly different thriving groups — trapped Chilean miners, a Dutch soccer club, a revitalized Paris neighborhood — and finds they all do two things well: they make meaning and they build community. Coyle blends real-world stories with science to offer practical tools for creating connection and belonging, whether in an organization or a neighborhood. An energizing pick that ties experience design and community-building together.

Finish up whatever you’re reading and make room for Flourish in your plans for this fall. If your a SE member and you’d like to be part of our Book Club but aren’t receiving my emails, drop me a line at ryan@speakingengagement.org or fill out this form.

About the Next Keynote

I mentioned Melissa Schipke in this newsletter in the context of her working with CMAC helping our partners on alumni engagement metrics and reporting. On Monday, we’re going to talk about something entirely different. (Well… mostly different). Melissa is the Creator & Host of Pitch-a-Friend, and it’s taking the singles world by storm. We talk about what she’s learned building this new type of networking experience and how she’s built a volunteer-led chapter network around the world.

Mallory unpacks how stress reshapes behavior, from the busy work of a flight response to the perfectionism of a freeze response, and why practice, rather than another new strategy, may be the most underrated tool in fundraising. She also makes the case for operational transparency: showing donors the steps of the journey rather than only the destination, as a way to build trust and turn affinity into a genuine sense of cause.

Upcoming Member Events

Agora

Behind the Scenes of a Signature Alumni Event: Lessons from the Bentley Alumni Conference

A great alumni conference can do more than bring people together — it can create the conditions for relationships to grow, alumni expertise to strengthen the institution, and university priorities to become meaningful and relevant to graduates.

In this Agora, Allison Kerivan, Executive Director of Advancement Relations, will take attendees behind the scenes of the Bentley Alumni Conference, the university’s flagship professional development and networking experience, and share how it has evolved into a strategic platform for alumni engagement and donor cultivation.

Date: Thursday, September 3 from 12 - 1 pm

Learn More (Members)

Faculty-in-Residence

For six weeks beginning August 17 - September 25, Speaking Engagement welcomes Mallory Erickson — executive coach, creator and host of the What the Fundraising podcast, and author of the book by the same name — as our inaugural resident.

We’ll have a final live Symposium event for members on September 23.

Learn More (Members)

Working groups and committees are usually effective at coming up with creative new ways to solve old problems. But we shouldn’t confuse creativity with innovation.

Creativity introduces a new idea. It takes the path with a slightly different angle, or a different toolset, or a different voice. Innovation changes the road.

Real innovation examines the structures and systems in which those new ideas work. That’s important in advancement and engagement because we’re usually a very creative bunch. We’ve been asked to do more with less for decades. Creativity is a badge of honor; ‘look at this new way we came at the problem.’

But it’s much easier to create something with a new alumni engagement program without examining the goal of alumni engagement. We can add another channel or messaging to fundraising outreach without paying attention to the actual processes involved in a donor’s relationship with the institution. Which, on some campuses, may well be the only way we can.

What comes from those creations may look like innovation while leaving the underlying systems unchanged. We end up creating around a problem, leaving everything underneath it untouched.

A good example is career support and placement. Connecting students to real-world experience and training is something everyone wants - employers, families, students, and institutions all see it as a foundational part of the college process. The idea that a degree delivery should deliver a one-to-one career return has become nearly universal. Families considering colleges want to know the practical career outcomes before they look at the residence halls. What kind of job will this college and this major result in, and is this investment in a degree program going to make more than it costs?

What resulted from that new calculus has been hundreds of incredibly creative programs that have made materially measurable value and have begun to address the expectations of students and their families. What didn’t come from it, mostly, was real innovation.

Most schools have the same departments in the same places with the same systems of connecting with employers. The same core curricula in degree programs. They do it much better than they used to because of the dedication and the creativity of their staff and leadership. But eventually, doing the same system better will run into its limits.

Then it becomes a systems question.

Kevin Grubb’s work around work-based learning offers a way to think about it. Before expanding to a broad view of the issue, he saw it firsthand at Villanova from the institutional level: what students gained from practical work experiences, where access broke down, and how employers and alumni could help. He also learned how difficult it was for any one campus to solve the problem on its own.

The interesting lesson for advancement is not that work-based learning matters.

It’s that good ideas keep running crosswise with the way our institutions are organized.

A student today probably interacts with career services, college-level programs, alumni relations, corporate relations, and development as entirely different parts of the university. An alumnus may encounter those same offices as five different requests for five different kinds of help.

That is the difference between creativity and innovation. Creativity would build a sixth program for that person. Innovation would let the five offices see that they are talking to the same human being.

Inside the institution, those distinctions make sense. Each office has its own directives, budget, goals, data, and metrics that define its success. But outside the institution, those distinctions can be almost meaningless.

I used to joke that many of the people I talked to seemed to imagine the entire university in one big building with the president at one end and the football coach at the other, and the rest of us just steps away from whatever solution they were looking for.

The alum who can introduce a student to an employer may also be a donor. The employer offering an internship may also be a corporate partner. The graduate willing to mentor a student may eventually become a volunteer​.

One person who our systems turn into categories. That’s what makes innovation harder.

When I worked in the advancement office at my alma mater, an alumnus I was an undergrad with became a very successful entrepreneur and started a multimillion-dollar direct-to-consumer brand that grew incredibly fast. Let’s call him Steve.

Steve now has a business relationship with Athletics Licensing, which puts the billboards in the stadium. He works with career services as a business that hosts internships. He’s been invited by the College of Business as a speaker and guest lecturer. Of course, the advancement office is interested in him as a donor, and student affairs knows him as an involved alum of his fraternity and the campus programming organization.

Because Steve loves his alma mater, he says he isn’t annoyed by the overlapping phone calls and requests to appear, but how many like him stop answering some of those calls?

Advancement loves the idea of one person “owning the relationship.” But a real alum’s relationship is nuanced and distributed.

It’s relatively easy to ask alumni relations to create a mentoring program. It’s much harder to build a system in which alumni engagement, career services, advancement, academic units, and employer relations can see that mentoring relationship as part of the same larger experience.

Fundraising has its own versions of the same problem.

We can produce a more creative annual giving appeal while leaving the donor journey unchanged. We add personalization to an email while continuing to segment people according to categories that tell how they give, but very little about why they give. We can adopt artificial intelligence tools to produce content faster while preserving a process that was not particularly effective before AI arrived.

Those things may be worthwhile. But we shouldn’t call them innovation. Putting a faster engine into a machine designed for the wrong job doesn’t fix anything.

So what does real innovation look like?

First, the highest value moves almost never come with a press release or a public announcement. That’s not always true, but much of the true innovation in higher ed is quiet, structural, and far more likely to change something. Some of the most important innovations in advancement may not look particularly innovative.

Letting information move between offices that have always guarded their own data or measuring alumni engagement so that helping a graduate find a job counts towards success, even when no gift follows. Allowing room for the idea that the donor journey shouldn’t just be about upgrade velocity.

We tend to talk about innovation as a way to do something new. Real innovation may be a way to stop doing something old.

That process asks different questions and requires different choices. Budgets, metrics, staffing, data structures. Those are all choices. The separation of careers services and alumni engagement is a choice. All of those choices were probably perfectly reasonable when they were made. Some of them still may be. But until we question some of those choices in light of a changing world, the creative ways we build around them may not be enough.

Creative, dedicated people can become extraordinarily good at compensating for a system that should have been reconsidered. But as W. Edward Deming said:

“A bad system will beat a good person every time.”

I helped build an event at my institution that, by the numbers we measured - attendance, mainly - was a success. We were happy because the room was full.

When we started asking questions about who was in the room, we realized a lot of work went into making a lot of people happy, but those happy people were engaged, in general, only with that event. They weren’t donors, they weren’t volunteers, they weren’t mentors. They weren’t doing anything that we asked of ‘engaged alumni.’

So we changed nearly everything. The concept remained the same, but we designed everything around it to reach and attract the alumni we were looking for specifically.

It worked: new attendees were more involved and more aligned with an engaged alumni base. We quickly realized that, while a few dozen people loved the old event, it was out of step with an alumni base of 250,000.​

The new event ran smaller numbers, but after a year, the people in the room were more involved than they had been the year before.

There were a few vocal alumni who were particularly annoyed by the new formats. Those I spoke with were sincere, and I was genuinely disappointed to disappoint them, but I knew what we were doing was better by every measurement that mattered.

The future of advancement will introduce new technologies, new ways of connecting people, and new ways to engage alumni and friends with our campuses. There will be new ways to connect students with experiences and networks that will advance their future careers.

But the institutions that drive real innovative change won’t be the ones with the most new ideas.

They will be the ones willing to ask a different question:

What if we built this around the people we serve instead of the structures we inherited?

Dave Hail is a fundraising strategist and storyteller who works with nonprofits and institutions to design stronger donor relationships and more effective engagement strategies. His work focuses on helping teams move beyond transactional communication toward systems that support long-term connection and growth.

His perspective sits at the intersection of strategy, systems, and storytelling, with a focus on helping organizations act with greater clarity and intention.

Dave is a lifelong learner, husband and dad, and lives in Oklahoma.

Upcoming Member Events

Agora

Behind the Scenes of a Signature Alumni Event: Lessons from the Bentley Alumni Conference

A great alumni conference can do more than bring people together — it can create the conditions for relationships to grow, alumni expertise to strengthen the institution, and university priorities to become meaningful and relevant to graduates.

In this Agora, Allison Kerivan, Executive Director of Advancement Relations, will take attendees behind the scenes of the Bentley Alumni Conference, the university’s flagship professional development and networking experience, and share how it has evolved into a strategic platform for alumni engagement and donor cultivation.

Date: Thursday, September 3 from 12 - 1 pm

Learn More (Members)

Faculty-in-Residence

For six weeks beginning August 17 - September 25, Speaking Engagement welcomes Mallory Erickson — executive coach, creator and host of the What the Fundraising podcast, and author of the book by the same name — as our inaugural resident.

We’ll have a final live Symposium event for members on September 23.

Learn More (Members)

Watch the full-length version on YouTube (47 mins)

Creating a structure around work-based learning isn’t about finding every student one internship, it’s designing a path that moves them across the whole continuum, and. It takes an enormous number of people, good data most schools don’t have, and a recognition that great work-based learning looks completely different in nursing than it does in business.

In our discussion we talk about where to start: not with some big new employer push, but by looking inward. Every school is already an employer, with campus jobs and work-study roles that could be turned into real, resume-worthy experiences. The opportunity is often already sitting right there on campus.

As states and systems rally around this, the temptation will be to chase numbers and let quality slip. If we grow work-based learning but the experience is hollow, especially for the students who need it most, we’ve missed the point. Getting it right is the whole thing.

Big Themes This Week

• Work-based learning is a continuum, from job shadows to apprenticeships, and the real work is designing a path across all of it, not landing one internship.

• It’s hard for concrete reasons: it takes a lot of people, the data barely exists, and good work-based learning looks different in every discipline.

• Start where you already are. Every school is an employer, and campus jobs and work-study can become real experiences.

Team Discussion Questions

• Are we thinking about the whole continuum, or just internships?

• Could our own campus jobs and work-study roles become stronger, resume-worthy experiences?

• As we scale, how do we protect the quality of the experience, especially for students with the most barriers?

Upcoming Member Events

Agora

Behind the Scenes of a Signature Alumni Event: Lessons from the Bentley Alumni Conference

A great alumni conference can do more than bring people together — it can create the conditions for relationships to grow, alumni expertise to strengthen the institution, and university priorities to become meaningful and relevant to graduates.

In this Agora, Allison Kerivan, Executive Director of Advancement Relations, will take attendees behind the scenes of the Bentley Alumni Conference, the university’s flagship professional development and networking experience, and share how it has evolved into a strategic platform for alumni engagement and donor cultivation.

Date: Thursday, September 3 from 12 - 1 pm

Learn More (Members)

Faculty-in-Residence

For six weeks beginning August 17 - September 25, Speaking Engagement welcomes Mallory Erickson — executive coach, creator and host of the What the Fundraising podcast, and author of the book by the same name — as our inaugural resident.

We’ll have a final live Symposium event for members on September 23.

Learn More (Members)

In a section of the book that begins on page 245 called “Return to First Principles,” Will quotes his Dad as he’s looking to affirm the mission statement for Eleven Madison Park.

Speaking Engagement is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

“Don’t run away from what you don’t want; run toward what you do.”

In my experience working with advancement teams over the last few years, there’s a must-do-everything-for-everyone mentality that shapes decision-making. If there’s one dynamic that will thwart most alumni leaders from reaching the level of personalized, memorable engagement that Will describes in Unreasonable Hospitality, it’s the fact that leaders struggle to run towards their desired future state. Instead, they try to put a wrapper around all the work they’ve been doing and call it a mission.

Will talks about making radical change to reach a freshly articulated mission statement and their objective “to be the most delicious and gracious restaurant in the world.” To get there, he writes about making tough decisions like cutting their menu in half and decreasing the number of courses.

Will Guidara’s vision for Eleven Madison Park was to create a truly unique dining experience where the customer’s vision and expectations is merged with the restaurant staff’s ability to bring it to life.

Alumni leaders are often restricted from moving to a desired future state by entrenched processes, but even more so by an inability to run toward something. The mission statement is too big, and because “everything” is wrapped up in it, there’s no ability to stop something to focus on reaching the desired future state.

Most advancement teams should run toward Unreasonable Hospitality through the lens of providing opportunities for alumni to help students.

Enrollment is down. Fewer college-age students are available to enroll. Colleges and universities need to attract and retain students. Alumni are massively underutilized in this effort. Meanwhile, we know that alumni really want to help students, and that volunteers give more over a lifetime.

Alumni might want other things too, but to reach Unreasonable Hospitality, they’ll have to find those things elsewhere. To work towards this mission of alumni helping students, the school must pour itself into the alumni that want a seat at this table.

To make a significant pivot like the one I’ve described, the right tactical next steps are needed.

Take a strategic pause from business as usual.

As Will describes in the book, it’s important to create the space you need. In my view, most teams try to “build the plane while flying it.” Instead, leadership must be comfortable taking a strategic pause on legacy programs that aren’t explicitly connected to the new mission. On page 143, Guidara notes that, “...no aspect of your business should be off-limits to reevaluation.”

Lean on your board members to act as advocates.

Throughout the book, Guidara describes how important his employees are as ambassadors for the restaurant. When a strategic pause is needed, both staff and leadership boards must be brought in and trusted with the plan to serve as public advocates for the changes underway. Board members are often the ones clamoring for change. They must also help provide the space for it but talking up what the school is doing, and even be willing to put the board itself on hiatus.

BTW… you’ll know if you’ve got the right alums on the board if they can not only stand by but create energy and enthusiasm during this building process.

Build on existing structures that present opportunity.

Let’s say advancement has an imperative to help build support for athletics. The President has weighed in. To stay true to the mission, tailgate experiences, for example, must include opportunities to help students. The innovation lies in embedding advice and reflection from alumni that’s shared or collected at an athletics event and brought back to students.

Make the experiences memorable, and emphasize convenience.

Throughout the book, Guidara describes the importance of creating unforgettable experiences. But he’s also clear that removing friction from the guest experience is imperative. Advancement is highly practiced in this area for donors making gifts, but not nearly so for volunteers hoping to give their time. Alumni want to help students; they just don’t have much time to give. The ask must be small and the process frictionless, and the alum needs to feel like their fifteen minutes might change a student’s path.

Last week, I wrote about the leadership lessons that jumped out at me from Unreasonable Hospitality. The big one is to slow down and make room for growth. My big takeaway from the book is that most alumni teams try to be everything to everyone. It didn’t work at Eleven Madison Park, and it hasn’t worked in higher ed. Every advancement leader needs to figure out what “their thing” is. I contend that this moment calls for a pivot — to run toward something different. For advancement, that means alumni, at scale, helping students, and building Unreasonable Hospitality around making it happen. Everything else on the menu, at the vast majority of schools, we should be brave enough to cut.

About Speaking Engagement

One aspect of starting a new endeavor like SE that I mentally prepared myself for, but could never fully be ready, is the number of people who have said “no.”

Today, one alumni leader shared that he’d wait until things were more “developed” before their organization would consider joining. WFT does that mean?!! Innovate with me!

That said…

The thing I learned long ago, going back to doing outreach to alumni and making volunteer asks, is never to be sad or frustrated by those who have said no. Instead, get excited about those that have said yes. Twenty-two schools have entered into paid member partnerships to date. These teams are led by and comprised of amazing engagement pros.

Over the last couple of weeks, 50 individuals from the University of Virginia joined Speaking Engagement. As a guy who lives in Virginia and spent a few years around Grounds, nothing makes me happier than having this group as part of the community. Welcome Hoos!

About the next Keynote

Kevin Grubb is my guest on the Keynote coming up on Monday, 8/24. For years, Kevin led the career unit at Villanova University, eventually becoming Associate Vice Provost, Professional Development and Chief Career Officer. Kevin left Villanova for Strada Education Foundation and the role of Vice President, Work-Based Learning. And if you guessed that we absolutely nerd out on how higher ed can tackle getting students relevant experiences on their resumes by the time they graduate, you’d be right.

Speaking Engagement is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

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When alumni engagement professionals talk about lifelong learning, our minds often go to familiar places, faculty lectures, continuing education, webinars, or panels featuring experts on our campus. These are valuable offerings that reinforce higher education’s great strengths, its ability to generate and share knowledge. But I wonder if we’ve unintentionally defined lifelong learning too narrowly.

That question has stayed with me throughout my first year in alumni engagement.

Before transitioning into alumni engagement, I spent much of my career in higher education in career services and experiential education, where learning was not confined to classrooms, it happened through internships, research projects, professional challenges, and reflection. Those experiences shaped students just as greatly was coursework did. When I moved into alumni engagement, I brought that perspective with me, and I began noticing that alumni continue to learn in many of those same ways long after graduation.

One experience challenged my own assumptions.

At the institution I currently serve, we launched a service in the summer event inspired by our intentional focus on educating for service. As I watched alumni serve together, I realized the impact extended far beyond giving back. They shared stories about their careers, reflected on why service still mattered to them years after graduation, exchanged ideas about their communities, and encouraged one another. I realized while we were not gathered in a classroom, meaning learning was still happening.

It made me ask: What if lifelong learning in alumni engagement is not about recreating the classroom after commencement? What if it is about creating opportunities for alumni to continue learning with, from, and alongside one another throughout their lives?

This is not an argument against academic programming. Faculty expertise, research, and continuing education remain important. Rather it is an invitation to broaden how we think about learning itself.

Learning does not happen exclusively through formal instruction in a classroom. It also develops through experience, reflection, dialogue, mentorship, and service. Experiential learning theory reminds us that meaningful learning occurs when people engage in experiences and intentionally reflect on them. Alumni engagement creates countless opportunities for exactly that kind of learning, through mentoring, service, leadership, storytelling, and shared experiences that deepen both knowledge and connection.

Alumni do not leave those ways of learning behind when they graduate. Perhaps learning in alumni engagement can be understood as any experience that helps alumni gain new knowledge, develop new skills, or see themselves, others, and the world from a different perspective. Viewing it this way, learning is already happening across many of the experience’s alumni are a part of.

A recent graduate navigating a first promotion learns from an alumnus who spent decades leading teams. A volunteer mentoring current students gains fresh insight into their own leadership style. Alumni participating in a community service project deepen their understanding of the communities they serve while reconnecting with their institutions mission. A reunion conversation between classmates becomes an opportunity to reflect on shared experiences, changing identities, and the unexpected paths life has taken them. None of these moments resemble a classroom. Yet learning can take place at all of them.

I have challenged myself to think about lifelong learning in alumni engagement through four different categories that often overlap.

This first is intellectual learning, the traditional academic experiences many of us immediately associate with. Lectures, research presentations, continuing education. These remain valuable ways for alumni to engage with ideas and continue to learn and adapt.

The second is professional learning. Alumni continue to develop throughout their careers, whether they are changing industries, leading organizations, launching businesses, or mentoring others. Alumni engagement professionals in collaboration with other campus and community partners can create spaces where those experiences are shared across generations benefiting both the alumni and current learners.

The third is civic learning. Many institutions encourage students to become engaged in the communities around them. Why should that expectation end at graduation? Service opportunities, volunteer leadership, and community partnerships allow alumni to continue learning through action while strengthening their connection both to their alma mater and their communities.

Finally, there is personal learning. Life continually invites us into new seasons, becoming a parent, caring for aging parents, navigating retirement, building resilience after setbacks, discovering new passions, or redefining our purpose. These experiences may never appear on a course catalog, but they often become the most transformative learning experiences. Alumni engagement has an opportunity to provide meaningful spaces to explore these transitions together. Viewing lifelong learning through these broader categories also changes the questions we ask alumni engagement professionals.

Instead of asking, How can we add learning to this event?

Perhaps we should ask, Where is learning already happening, and how can we intentionally create more opportunities for it?

Maybe this broader understanding of learning also challenges how we measure success. If mentoring, service, storytelling, and meaningful conversations are forms of learning, then they are not simply engagement activities, they are educational outcomes.

That shift moves alumni engagement simply beyond delivering content. It positions us as facilitators of relationships, conversations, service, and shared experiences where learning naturally occurs. Alumni themselves carry decades of expertise, lived experience, and wisdom. One of our greatest opportunities is to not just share knowledge from our institutions to alumni, but to create opportunities where alumni can generously share that knowledge with one another and across generations and different life stages.

Many institutions promise more than four years of education. They aspire to prepare graduates for lives of purpose, leadership, citizenship, and service. If that mission truly extends beyond commencement, then alumni engagement is more than maintaining relationships, or increasing attendance at events. It becomes an extension of the institution’s educational mission, a way of supporting alumni as they continue to grow, contribute, and learn throughout their lives.

If we believe education has the potential to transform lives, then perhaps alumni engagement is not simply about helping graduates stay connected to their institutions, perhaps it is about ensuring they never stop learning and growing because of it.

Rebekah Harriger is the Director of Alumni Engagement and CEO of the Elizabethtown College Alumni Association. She has worked in higher education since 2016, with nearly a decade of experience spanning career services, experiential learning, and alumni engagement. Her work centers on helping students, alumni, and professionals articulate the value of their experiences, build confidence, and pursue meaningful career pathways.

Prior to her current role, Rebekah served as the Senior Director of Career Services and Experiential Learning at Harrisburg University of Science and Technology, where she led campus‑wide career readiness and experiential learning initiatives that aligned student learning with workforce needs.

In her current role, Rebekah brings a strategic and relational lens to alumni engagement, leading efforts to strengthen lifelong connections, cultivate alumni involvement, and inspire graduates to give back through service, philanthropy, and connect with current students.

Upcoming Member Events

Agora

Behind the Scenes of a Signature Alumni Event: Lessons from the Bentley Alumni Conference

A great alumni conference can do more than bring people together — it can create the conditions for relationships to grow, alumni expertise to strengthen the institution, and university priorities to become meaningful and relevant to graduates.

In this Agora, Allison Kerivan, Executive Director of Advancement Relations, will take attendees behind the scenes of the Bentley Alumni Conference, the university’s flagship professional development and networking experience, and share how it has evolved into a strategic platform for alumni engagement and donor cultivation.

Date: Thursday, September 3 from 12 - 1 pm

Learn More (Members)

Faculty-in-Residence

For six weeks beginning August 17 - September 25, Speaking Engagement welcomes Mallory Erickson — executive coach, creator and host of the What the Fundraising podcast, and author of the book by the same name — as our inaugural resident.

We’ll have a final live Symposium event for members on September 23.

Learn More (Members)

A big idea from her excellent book, What The Fundraising: Embracing and Enabling the People Behind the Purpose is that the ask is really an offer. You’re not extracting a gift, you’re giving someone a way to live out their values. Get curious about what actually drives a person and you build a partnership instead of a transaction.

She’s also blunt about scarcity. You can only raise what you believe is possible, and a shop grumbling about “only ten thousand alumni” is sitting on a base most nonprofits would envy.

She says burnout isn’t really about overwork. It’s rejection, uncertainty, and the stories we tell ourselves about the discomfort. Worth sitting with.

Big Themes This Week

• Fundraising is sacred work. Done well it helps people move money toward what they care about most, and the stigma comes from society, not from the work itself.

• Great fundraising is not an ask, it’s an offer. Alignment means understanding what drives the other person and co-creating a win-win, not extracting a gift.

• You can only raise what you believe is possible. Scarcity mindset, not the size of your alumni base, is often the real ceiling.

Team Discussion Questions

• Are we brave enough to tell someone this isn’t the right fit right now, and trust that honesty builds the relationship?

• Where is scarcity thinking quietly capping what we believe is possible with our base?

• When the ask feels like dread, are we blaming overwork instead of the beliefs and pressures underneath it?

Upcoming Member Events

Agora

Behind the Scenes of a Signature Alumni Event: Lessons from the Bentley Alumni Conference

A great alumni conference can do more than bring people together — it can create the conditions for relationships to grow, alumni expertise to strengthen the institution, and university priorities to become meaningful and relevant to graduates.

In this Agora, Allison Kerivan, Executive Director of Advancement Relations, will take attendees behind the scenes of the Bentley Alumni Conference, the university’s flagship professional development and networking experience, and share how it has evolved into a strategic platform for alumni engagement and donor cultivation.

Date: Thursday, September 3 from 12 - 1 pm

Learn More (Members)

Faculty-in-Residence

For six weeks beginning August 17 - September 25, Speaking Engagement welcomes Mallory Erickson — executive coach, creator and host of the What the Fundraising podcast, and author of the book by the same name — as our inaugural resident.

We’ll have a final live Symposium event for members on September 23.

Learn More (Members)

There’s a better pathway forward for all alumni associations to create a strategic plan that everyone can rally around.

Speaking Engagement is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

There are really three types of alumni associations. The first is fully independent. There are a very small number of these left in the U.S., where the association brings in revenue, covers all or most of its operating costs, and employs its own staff. Another organization type can be classified as interdependent, which is when a separate 501(c)(3) non-profit alumni association exists and brings in money through various royalty agreements, but the school employs all the staff. There are varying degrees of interdependence. A third type is the alumni association in-name-only. There’s no separate 501(c)(3) organization, but the university’s advancement office has elected to brand all alumni-facing programs as coming from an alumni association.

None of these alumni organizations need their own strategic plan.

My reasoning is that, without exception, alumni engagement is not limited to the events, programs, and initiatives created and executed by the alumni association. Engagement is happening all over the institution, all the time, and often without any connection to the alumni association and its resources.

Career services offices engage alumni at career fairs and as mentors. Alumni help admissions offices by volunteering at regional high school enrollment fairs. Athletics departments often engage their former athletes in mini-reunions put on by coaches, and academic deans have their own cohorts of alumni they involve in classroom panels and presentations. These are just a few examples.

Alumni engagement is happening all over the institution, and the alumni association often has nothing to do with it. Sometimes the administrative and volunteer leaders don’t even know anything about the engagement happening elsewhere on campus, so why should an association have a strategic plan that paints the picture that somehow they’re “in charge” of alumni involvement when they’re plainly not?

Alumni engagement is a symphony.

The analogy I use most often when conducting strategic planning workshops is to suggest that alumni engagement at any institution is a symphony. Each institution must develop its own time signature — the beats in the measure and the value of each beat. Everyone across the university needs to be playing from the same sheet of music.

I often describe the alumni association as the percussion section of the symphony. It’s there to help by keeping the beat and to make sure the other sections of the symphony stay connected so the music sounds great. To continue the metaphor, the College of Business is then the woodwinds section, and athletics is the strings, and career services is the brass, etc. These sections often have their own soloists.

The percussion section (alumni association) is also capable of producing some incredible solos, too. Still, broadly speaking, it exists to help keep the rest of the symphony in time, with a distinct tempo and form. But when a good plan is in place, and everyone is bought in, the symphony creates beautiful music.

When it’s not, the song sounds like shit because everyone is playing over each other.

An alumni association should play a significant but ultimately supporting role in conducting enterprise-wide engagement.

Whenever I do strategic planning for alumni and constituent engagement with my CMAC clients, I work with my partners in advancement or the alumni association to bring together a task force of individuals from across the institution to help inform and build the finished plan. These are representatives from all the sections in the symphony.

The reason for this is not just because these task force members (faculty, administrators, students, and volunteers) are already engaging alumni in their day-to-day work; it’s to avoid silos and ensure everyone is playing from the same sheet of music.

So no — your alumni association doesn’t need its own strategic plan. Instead, it needs to play the most important supporting role. All educational organizations need an enterprise-wide plan for alumni engagement, and the association is the percussion section that keeps everyone in time; that’s how you get a Boston Pops-quality performance.

About Speaking Engagement

Last week, I promised a Part 2 article about the tactics for creating Unreasonable Hospitality based on Will Guidara’s book. I’ll get back to that next week.

Here’s an update on the content format and delivery method moving forward so subscribers and members can anticipate what’s arriving and on which days. I also want to be conscious of not hitting your inboxes too much.

Subscribers (free) and Members (paid):

Mondays: The Keynote podcast. Starting Monday (8/17), you’ll always be able to watch or listen on LinkedIn via our SE Page, speakingengagement.org, or in the Substack app, but I’m not going to hit your inbox.

Fridays: My newsletter - delivered by email, podcast (AI-reading), and available through the app or site.

Members-only:

Tuesdays: A featured article from our Contributing Editors, our Faculty-in-Residence, or a guest post from an SE member - delivered by email newsletter, podcast, app, or site.

Wednesdays: Our additional video podcast for the week, including the Breakout, a recent Agora presentation, or an extended conversation featuring the research from our Faculty-in-Residence or Book Club commentary. This will be delivered by podcast or through the app and website.

Thursdays: Every other week, you’ll receive an announcement of an upcoming event, program, or initiative. This will be delivered as an email and available on the site or Substack app.

What this all means is that free Subscribers will receive one email from us per week, and Members will receive two emails most weeks, three on announcement weeks.

Up Next on The Keynote

We begin our Faculty-in-Residence experience by featuring Mallory Erickson on the Keynote. Mallory is our resident for the next six weeks, starting on Monday!

Mallory Erickson works at the intersection of fundraising strategy, executive coaching, and behavior design to help nonprofit professionals excel at the most human part of their job, connection. A former fundraiser turned coach, she has trained over 100,000 fundraisers. She is the creator of the Power Partners Formula™️, a framework that helps nonprofit leaders raise more from the right funders so they can move more money toward what matters most, without burning out.

She is the author of What the Fundraising and host of the podcast by the same name, where she unpacks the hidden systems that shape how fundraisers show up, from chronic stress and perfectionism to the scarcity mindset embedded in the sector’s DNA. Her work centers on the belief that when we support the people behind the purpose, we get better results and a more sustainable social impact sector.

In 2025, Mallory launched Practivated, an AI-powered fundraiser readiness platform. Readiness, the way Practivated defines it, is the combination of skills, confidence, and muscle memory, and until now, fundraisers have had almost no structured way to build it. From big asks to tough objections, Practivated gives fundraisers a safe, dynamic space to practice the conversations that matter most, building the internal capacity to show up, adapt, and connect no matter who walks in the room.

Speaking Engagement is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

Across both, the conversation keeps returning to treating engagement as the strategy and philanthropy as one of its outcomes, and to building a culture of philanthropy that starts well before the first gift. It also gets practical about the real barriers, staffing, budget, accountability, and patience, and what schools on a tight timeline can do right now.

Referenced in this episode:

• Kelly Dolan-Sapp and Yiesha Thompson, “Why Alumni Networks Are the Most Undervalued Belonging Strategy,” University Business: https://universitybusiness.com/alumni-networks-are-the-most-undervalued-belonging-strategy/

• Darren Miller, “A Joking Truth: Why It’s Time to Move Beyond Annual Giving,” LinkedIn: https://www.linkedin.com/pulse/joking-truth-why-its-time-move-beyond-annual-giving-darren-miller-shvle/

Upcoming Member Events

Agora

Behind the Scenes of a Signature Alumni Event: Lessons from the Bentley Alumni Conference

A great alumni conference can do more than bring people together — it can create the conditions for relationships to grow, alumni expertise to strengthen the institution, and university priorities to become meaningful and relevant to graduates.

In this Agora, Allison Kerivan, Executive Director of Advancement Relations, will take attendees behind the scenes of the Bentley Alumni Conference, the university’s flagship professional development and networking experience, and share how it has evolved into a strategic platform for alumni engagement and donor cultivation.

Date: Thursday, September 3 from 12 - 1 pm

Learn More (Members)

Faculty-in-Residence

For six weeks beginning August 17 - September 25, Speaking Engagement welcomes Mallory Erickson — executive coach, creator and host of the What the Fundraising podcast, and author of the book by the same name — as our inaugural resident.

We’ll have a final live Symposium event for members on September 23.

Learn More (Members)

If you’ve seen The Princess Bride, this rings bells for you. If you haven’t here’s some context: One of the characters, a gangster named Vizzini, uses (er, misuses) the word repeatedly the Dread Pirate Roberts overcomes challenge after challenge to try to rescue the titular princess, whom Vizzini has kidnapped. Another character—his colleague in crime, Inigo Montoya—finally says to him: “You keep saying that word. I do not think it means what you think it means.”

In alumni and donor engagement, we have a word like that. It’s “community.”

It appears on our websites, strategic plans, donor appeals, and social media posts. It’s operationalized through programs and events, such as tech platforms, happy hours, tailgates, networking nights, and 5K runs, to name a few.

The roots of that approach, as Richard Millington noted in a recent Keynote episode, are in part structural. The founder of FeverBee and expert in online communities explained that, while higher ed advancement teams have no shortage of staff with event-planning or content-creation skills, they lack people with skills specifically geared toward community building.

But the reasons are also philosophical. Too often, when our own institution’s engagement efforts fizzle after an initial burst, we look outward for other ideas. We ask, “What programs earned a CASE Award for alumni engagement last year?” “Who in our field is the best at building community among their constituents?”

If an advancement team had a specific community engagement specialist position, and that person were well-versed in community-building strategies, they’d ask a different question:

Do we know what community means to our people?

The answer is likely, “Not really.”

Historically, we’ve tracked how alumni feel about us through proxy metrics like response rates, RSVPs, and net promoter scores. Yet these metrics don’t measure relevance—which is what the latest National Alumni Survey results show as critical to alumni’s interest in engaging and giving back to their alma maters. To have that kind of relationship, alumni need the institution to show up in their lives organically, no matter their age or stage.

(Spoiler alert: “Showing up organically” doesn’t mean through an annual report or tear-jerker Giving Tuesday appeal.)

Answering the question of what community means to our alumni and donors isn’t easy. Our knee-jerk reliance on “best practices” or other institutions’ models likely won’t help much—both because I’m not sure there’s an institution that’s really figured this out, and because what works for one alumni population may not work for another.

An answer I keep circling back to is a bit of a paradox: What if building a stronger alumni community is less about connecting alumni to the institution and more about connecting alumni to one another? What if a key to keeping the institution relevant in the lives of alumni has very little to do with the institution itself?

In our first episode of Keynote way back in April, Whop’s John Hill spoke with Ryan about how, in an AI-driven world, human connection is becoming a commodity. Community, in a sense, has a luxury item. With sophisticated data collection, analysis, and—yes—some help from AI tools, alumni engagement teams can become purveyors of this luxury item to their constituents.

They can help people moving to new cities, states, or even countries find at least one person with a shared connection to show them the ropes. First-time parents in an area could connect with fellow alumni to compare notes on potential babysitters. Someone seeking a weekly running group could find local graduates who lead one. When the football team comes to town to play a local rival, alumni could coordinate a meetup for themselves and their families.

What are the mechanics of this kind of model? That’s where I get a little stuck. Is it a new kind of digital platform that succeeds where we’ve previously failed with Facebook groups and bespoke alumni communities? Is it an investment in staff whose entire job is to focus on building these kinds of communities, rather than leaving it all up to volunteers?

Whatever the solution is, it’ll require experimentation. Maybe, for one year, it’s transforming Homecoming from an on-campus event to a regional observance, empowering local alumni to celebrate their shared tie to the institution wherever they are. Maybe it’s transferring some of the funding for an alumni chapter program that’s floundering to building, maintaining, and moderating digital tools that alumni can use to build community on their own.

The entire program won’t be perfect from the get-go. And, as Millington says, it shouldn’t try to be.

“If you look at how communities generally develop, the ones that really succeed and are sustainable for the long term, they usually begin small,” he says. It can be as few as five or ten people organized around one particular idea.

“Associations and alumni groups often go wrong because they try to launch a hundred groups at once, and then they’re surprised when all these groups don’t burst to life. But that’s not how it works,” he says. “You create one group at a time, get that going, then move on to the next one.”

Ten graduates deeply connected over issues that matter in their lives may sound small, but they’re probably worth more to an institution than a thousand dormant accounts on an alumni portal. It’s not a number that CASE will hand out an award for, and it may not turn the heads of institutional leaders. But it’s a starting point.

Maybe an alumni community that serves the institution and keeps it relevant in graduates’ lives isn’t so inconceivable after all.

Upcoming Member Events

Agora

Behind the Scenes of a Signature Alumni Event: Lessons from the Bentley Alumni Conference

A great alumni conference can do more than bring people together — it can create the conditions for relationships to grow, alumni expertise to strengthen the institution, and university priorities to become meaningful and relevant to graduates.

In this Agora, Allison Kerivan, Executive Director of Advancement Relations, will take attendees behind the scenes of the Bentley Alumni Conference, the university’s flagship professional development and networking experience, and share how it has evolved into a strategic platform for alumni engagement and donor cultivation.

Date: Thursday, September 3 from 12 - 1 pm

Learn More (Members)

Faculty-in-Residence

For six weeks beginning August 17 - September 25, Speaking Engagement welcomes Mallory Erickson — executive coach, creator and host of the What the Fundraising podcast, and author of the book by the same name — as our inaugural resident.

We’ll have a final live Symposium event for members on September 23.

Learn More (Members)

(Watch the full length version on YouTube - 54 mins)

That scattering is why he says the word we all reach for, integration, has become “the most abused word” in advancement technology, thrown around for anything down to moving a file out of one system and into another. His team poured effort into engagement scoring, and he admitted, plainly, that very few of their customers use it, because everyone defines engagement differently and few have a plan for what to do with a score once they have one.

Kalyan is refreshingly clear that AI is an enabler of human work, not a replacement for it, and genuinely optimistic that we can make every donor feel stewarded like a major one. I think people connect to him because he is both a builder and a straight shooter, and our field could use more of both.

Big Themes This Week

• Declining participation, not total dollars, is the real threat to a program’s long-term sustainability.

• “Integration” has become the most abused word in advancement tech. Real integration means seeing the same person whole across every system.

• Engagement and fundraising aren’t two worlds with a handoff, they’re one continuum, and our systems and teams should reflect that.

Team Discussion Questions

• Are we watching participation as closely as we watch dollars?

• Where do our tools promise to connect but quietly don’t, leaving the same person split across systems?

• Do we treat engagement and fundraising as a continuum, or as a handoff?

Upcoming Member Events

Agora

Behind the Scenes of a Signature Alumni Event: Lessons from the Bentley Alumni Conference

A great alumni conference can do more than bring people together — it can create the conditions for relationships to grow, alumni expertise to strengthen the institution, and university priorities to become meaningful and relevant to graduates.

In this Agora, Allison Kerivan, Executive Director of Advancement Relations, will take attendees behind the scenes of the Bentley Alumni Conference, the university’s flagship professional development and networking experience, and share how it has evolved into a strategic platform for alumni engagement and donor cultivation.

Date: Thursday, September 3 from 12 - 1 pm

Learn More (Members)

Faculty-in-Residence

For six weeks beginning August 17 - September 25, Speaking Engagement welcomes Mallory Erickson — executive coach, creator and host of the What the Fundraising podcast, and author of the book by the same name — as our inaugural resident. We’ll have a final live Symposium event for members on September 23.

Learn More (Members)

The wait was worth it.

The first 200 pages make it clear that Guidara’s ideas for executing this extraordinary level of hospitality actually live downstream from essential leadership. It’s not possible to get to the top echelon of service he describes without building towards it, carefully but deliberately over time. So this week, I thought I’d write about the leadership constructs that really connected with me, and next week I’ll come back to the tactics he describes to create Unreasonable Hospitality, and both the connections and implications for advancement teams.

Go slow to go fast

“We’re building the plane while flying it.” It’s the phrase I hear often as a consultant and the one I hate most because it’s usually how leaders describe never slowing down. I understand what this means in terms of having to make adjustments while still moving forward, but in reality it usually means chaos and leadership isn’t taking the time to make sure everyone is on the plane, and no one is left on the tarmac.

Everything is go-go-go, and it usually doesn’t work out very well.

Will talks about a realization that while the leadership at Eleven Madison Park was pushing hard to go from three to four Michelin stars, and the team was on board, he soon realized the pace was causing a meltdown he hadn’t anticipated. Everyone at the restaurant was so busy putting the patrons first that they forgot to take care of themselves.

This dynamic happens in the advancement field all the time. We’re so busy taking care of alumni and donors on nights and weekends after we’ve worked all day, too, planning those events, that self-care is often neglected.

He writes, “We encouraged them to find their oxygen and to take the time to breathe. Slowing down wasn’t just about nurturing them in the moment. It was about building a more solid foundation for the future, so that when we needed to speed up again (and we would, very soon) our minds and hearts were in top shape.” (pg. 158)

Of all the excellent concepts in the book that are important for creating a culture where next-level hospitality can thrive, this one stood out to me as the most important. It’s also something that engagement pros are really bad at. We’re always adding, and rarely subtracting. It’s incredibly important to build this muscle of slowing down in order to eventually gain speed again. Deconstruct in order to rebuild, but better.

Empower young staff to “own something”

Another concept from the book that I love is that Guidara bolds certain text containing a key point he wants to get across. On page 110, he writes (in bold), “Often, the perfect moment to give someone more responsibility is before they’re ready.”

He describes how he empowered his new team members to own important aspects of the restaurant during his time at Eleven Madison Park. He assigned ownership of all components of the restaurant’s coffee service to one person who was particularly knowledgeable of and passionate about it. He assigned beer to another person. Same with the linens and organizing the reservations office. Ownership of these tasks was offered to new team members as they began working in the restaurant.

He writes, “These ownership programs gave these motivated, creative people a project to engage with while they earned their stripes. And the investment of time and trust and education was almost always worth it, because when we mentored someone into full ownership, our jobs became easier over the long term.” pg. 108

In a typical alumni/advancement office, we tend to fold these opportunities into job descriptions and spread them across a program team. We also treat ownership as a reward for seniority rather than something that propels career growth. His idea of ownership is about a new hire who appears to have a knack for something taking on a task before clearly demonstrating readiness for it.

What could a young person have ownership over? For starters, I’d give someone ownership over a swag program and even something as big as owning the visiting-volunteer experience on campus, and they can decide how to build it and make it great.

New traditions for the team that meet a need

In our space, we tend to think of traditions as a events or symbols we honor and steward for our alumni and the broader university community. However, it’s rare for advancement teams to have a special tradition that allows the team members to feel seen and heard.

In Unreasonable Hospitality, Guidara describes how Thanksgiving became a special occasion not just for guests, but for the team that works at Eleven Madison Park. He writes that, “People who are gifted at hospitality tend to be sensitive. They notice everything, feel deeply, and care a lot. These are superpowers, though that tenderness can also make them a handful to manage.” (pg. 145)

My own experience with engagement pros is that they’re similar in nature to hospitality professionals and need that extra dedicated time along with something to look forward to. Often, advancement leaders tackle these challenges but without building a tradition for the staff that serves a purpose or fills a need. It’s usually a big employee appreciation event in the dining hall, but for everyone who works at the school. It’s a staff awards program that leadership starts, but the staff feels is forced and a bit of a drag.

I think alumni leaders have an opportunity to build special moments for the staff into the traditions that they construct for alumni and donors; maybe it’s right before or right after reunions or alumni weekend. It doesn’t have to be big, but it does need to be something that the team can genuinely look forward to.

I’m just scratching the surface with the great leadership lessons in Unreasonable Hospitality. More next week!

I’d love your thoughts and examples of how you or your leaders have worked to create a culture that models or resembles the one at Eleven Madison Park described in the book. If you’ve read the book, what leadership lessons stand out to you?

(Also, a big thanks to Matt Brandon at William & Mary for sending me a copy of Unreasonable Hospitality and for the homework assignment to read it and bring some ideas back to the team later in August.)

About the next Keynote

On Monday I’ll be publishing my interview with Kalyan Varma, the Co-Founder & CEO of Almabase. We discuss the challenges that face engagement leaders from an operational perspective, and Kalyan will share his view on some of the roadblocks that cause teams to stumble from a technology standpoint. I’ve known Kalyan, and I’m psyched to have him on the Keynote.

Upcoming Member Events

Agora

Behind the Scenes of a Signature Alumni Event: Lessons from the Bentley Alumni Conference

A great alumni conference can do more than bring people together — it can create the conditions for relationships to grow, alumni expertise to strengthen the institution, and university priorities to become meaningful and relevant to graduates.

In this Agora, Allison Kerivan, Executive Director of Advancement Relations, will take attendees behind the scenes of the Bentley Alumni Conference, the university’s flagship professional development and networking experience, and share how it has evolved into a strategic platform for alumni engagement and donor cultivation.

Date: Thursday, September 3 from 12 - 1 pm

Learn More (Members)

Faculty-in-Residence

For six weeks beginning August 17 - September 25, Speaking Engagement welcomes Mallory Erickson — executive coach, creator and host of the What the Fundraising podcast, and author of the book by the same name — as our inaugural resident. We’ll have a final live Symposium event for members on September 23.

The conversation works through Dobosz's argument that a first gift is a question rather than a transaction, and his four-part fix for a donor's first 90 days. It also gets honest about why that fix is far harder to run in a real advancement shop than it looks on paper. The episode closes on what actually earns a second gift and gives donors a reason to stay.

Upcoming Member Events

Agora

Behind the Scenes of a Signature Alumni Event: Lessons from the Bentley Alumni Conference

A great alumni conference can do more than bring people together — it can create the conditions for relationships to grow, alumni expertise to strengthen the institution, and university priorities to become meaningful and relevant to graduates.

In this Agora, Allison Kerivan, Executive Director of Advancement Relations, will take attendees behind the scenes of the Bentley Alumni Conference, the university’s flagship professional development and networking experience, and share how it has evolved into a strategic platform for alumni engagement and donor cultivation.

Date: Thursday, September 3 from 12 - 1 pm

Learn More (Members)

Faculty-in-Residence

For six weeks beginning August 17 - September 25, Speaking Engagement welcomes Mallory Erickson — executive coach, creator and host of the What the Fundraising podcast, and author of the book by the same name — as our inaugural resident. We’ll have a final live Symposium event for members on September 23.

Learn More (Members)

I created a new digital habit, and it stuck, but I know from experience they often don’t.

As my career progressed, I found the normal outlets. I went to conferences (maybe once a year) and tried networking with the other fundraisers in my organization. I started a newer fundraiser group for all those new(ish) people to fundraising and we started gathering monthly in person to talk about what we were learning, hearing, and seeing from the road. That was when I started to realize how much community and accessible content or professional development would be critical to my own growth and engagement with work.

Fast forward to COVID and I’ve stepped into my first talent management and senior leadership role. That eagerness to build community, find support, and access resources more easily than once a year at a CASE conference only grew. Fortunately, I was invited to join a group of talent managers in advancement who connected on Zoom monthly. What started as support to make it through the pandemic turned into a regular connection point to talk shop, share resources, and compare notes about what was working or not working in our institutions. No one was presenting at each other — we posed questions and shared our perspectives or resources.

That group eventually evolved into Advancement Talent Co, which now supports hundreds of talent managers across 60+ institutions with thousands of resources being shared. What I learned from watching it grow is something I probably should have known already: the real growth happens not only by consuming professional development but by engaging in it fully with other humans.

Professional development in advancement has mostly been a solo sport. You go to the conference once a year, if you’re lucky and if your institution has the budget. But since 2020, we’ve seen a host of new opportunities crop up that are digital-first, hybrid, and combinations of synchronous and asynchronous learning.

I said yes to Speaking Engagement because I’ve seen what’s possible when advancement professionals find each other and start showing up consistently. But I’d be lying if I said I wasn’t worried about it too.

Building ATC was easier in one unexpected way - COVID forced the habit. Everyone was already on Zoom, already looking for connection, already willing to try something new digitally. Speaking Engagement doesn’t have that same tailwind.

We’re asking a new group of people to come together and form a new habit from scratch, and new digital habits are genuinely hard to build. There’s been some impressive growth already - 330+ members across 25 institutions over four months is impressive growth. And yet, the comments are quiet and the synchronous events are still finding their footing. But, this is where the rubber meets the road for community building - to transition from content to community will require intentional engagement from both SE contributors as well as readers.

And, as any good fundraiser would say: I’d be remiss if I didn’t invite you to join us. Make a comment, pose a question or come to our next Agora.

Watch the full-length version on YouTube (57 mins)

Back in 2016, Liz was co-presenting on social listening at a higher ed marketing conference. The room was so full people sat on the floor, and afterward the line to talk to her was long, and everyone said the same thing: this makes complete sense, and here is why I will never be able to do it on my campus. “Listening and showing up really aren’t the same thing,” she says. You can learn what a community thinks without barging in to correct the record, and most of the time barging in is exactly the wrong move.

Liz is rigorous and refreshingly honest, no single metric to rule them all, no barging into every Reddit thread. But she is also optimistic that people are finding their way back to real community, online and in person.

Big Themes This Week

• The most trusted voice about your institution is usually an anonymous peer, not your official account. Trust is transferable, and it moves in conversations you aren’t watching.

• Listening and showing up aren’t the same thing. You can learn from a community without barging in, and often you should stay out.

• Followers and reach are vanity metrics. Measure the conversations that matter, and whether you’re activating other people to tell your story.

Team Discussion Questions

• Where are we broadcasting at people when we should be listening to them?

• Which metrics are we reporting that don’t actually connect to our goals?

• Who among our students and alumni are already telling our story well, and how could we support them?

Upcoming Member Events

Agora

Behind the Scenes of a Signature Alumni Event: Lessons from the Bentley Alumni Conference

A great alumni conference can do more than bring people together — it can create the conditions for relationships to grow, alumni expertise to strengthen the institution, and university priorities to become meaningful and relevant to graduates.

In this Agora, Allison Kerivan, Executive Director of Advancement Relations, will take attendees behind the scenes of the Bentley Alumni Conference, the university’s flagship professional development and networking experience, and share how it has evolved into a strategic platform for alumni engagement and donor cultivation.

Date: Thursday, September 3 from 12 - 1 pm

Learn More (Members)

Faculty-in-Residence

For six weeks beginning August 17 - September 25, Speaking Engagement welcomes Mallory Erickson — executive coach, creator and host of the What the Fundraising podcast, and author of the book by the same name — as our inaugural resident. We’ll have a final live Symposium event for members on September 23.

Learn More (Members)

Although Dartmouth enjoys extraordinary school spirit and alumni engagement feels like it’s part of the fabric of the school much more so than others, it was interesting to listen to discussions about the best way to generate a focused set of strategies that strengthens a “for life” approach, and really hone-in on this part of life — those years immediately post graduation. Even schools that have broad alumni loyalty are struggling to keep recent graduates connected after they toss their caps in the air at Commencement.

Our clear opportunity to boost young alumni engagement

At the heart of the opportunity with young grads is actually the same fundamental dynamic that should shape broader engagement across ages and life stages: average lifetime giving to alma mater is significantly higher among alumni who volunteer.

Howard Heevner’s research and that of my colleagues from CMAC and Washburn McGoldrick around The National Alumni Survey has really elevated the discussion around this important fact about alumni volunteerism. In the recently released Volunteering Signals Engagement and Giving Potential: Supplemental Report to the 2026 National Alumni Survey Annual Report, Heevner and team note that alumni are volunteering, just not with their alma mater. Higher education ranks eighth in the Top 10 Volunteer-Supported Causes.

Schools must scale volunteerism through Alumni Messenger programs.

I contend that the big reason young alumni aren’t as engaged as they could be is that there simply aren’t enough fun and meaningful opportunities to help. What opportunities exist feel like a heavy lift, like a chapter leadership role, or uninspired, like a digital ambassador social sharing program that’s more about the reshare than the advice.

Every educational organization needs at least one Alumni Messenger program. These are programs where the principle volunteer ask if for a brief amount of time (an hour or less, perhaps) to provide advice, reflection, and/or praise to students or others in the community. Within this classification of programs examples include:

• Alumni writing congratulatory postcards to accepted students

• Alumni making welcome phone calls to students who have deposited

• Grads interviewing prospective or admitted students

• Graduates writing advice on cards that are pinned to the doors of first-year students at move-in

• Alumni volunteers providing feedback on scholarship applications

• Alumni recording short videos of welcome, encouragement, or congratulations that are distributed to students by text or email

• Technology like Protopia that scales alumni-supplied advice to students and faculty

We need to be thinking about thousands of volunteers, not hundreds.

These programs that I’d classify as micro-volunteering are what every university needs: at least one Alumni Messenger program that provides a joyful and accessible way for alumni to help in short bursts of time, no matter where they live. These strategies require creativity and resources, but I’m certain that they’re essential to modern approaches to alumni engagement because they represent both an on-ramp and re-engagement because they can scale and help develop a culture of generosity.

Our main challenge is that we need more volunteer opportunities. Our young alumni aren’t ready to make gifts of treasure, and we’ve not done a good enough job providing avenues for anyone who wants to help to make a gift of time by sharing their reflections, advice, or offering words of encouragement.

This feels like an easy fix, but then again, there’s plenty we’ll have to stop doing in order to start and dedicate resources to Alumni Messenger programs.

About Speaking Engagement

If you’ve come to find our SE community valuable as a professional development resource, there are a few ways that we could use your help spreading the word.

1. Consider leaving a review on Apple Podcasts for the Keynote podcast. This helps more people find Speaking Engagement that might be looking for content on advancement engagement.

2. Follow and share Speaking Engagement on LinkedIn recommend our Page to your network.

3. Download the Substack app for your phone and consider recommending the Publication to your network.

I’m trying to get better at posting Notes in Substack. If you’re a Substack fan, please consider chiming-in! That aspect of Substack is kinda like X/Twitter, which I’m not sure how I feel about. More on that…

About the next Keynote

I’m psyched to share my interview with Liz Gross, Ph.D. Liz is the Executive Director, Strategic Enrollment Services at The College Board and an expert on social intelligence in higher education. During our discussion, we hit on how modern web functions to elevate different conversation that are happening about institutions, often without schools knowing it.

Watch for the episode to drop on Monday at 7 am ET.

Upcoming Member Events

Agora

Behind the Scenes of a Signature Alumni Event: Lessons from the Bentley Alumni Conference

Date: Thursday, September 3 from 12 - 1 pm

Speaker: Allison Kerivan, Executive Director of Advancement Relations at Bentley University

A great alumni conference can do more than bring people together — it can create the conditions for relationships to grow, alumni expertise to strengthen the institution, and university priorities to become meaningful and relevant to graduates.

In this Agora, Allison Kerivan will take attendees behind the scenes of the Bentley Alumni Conference, the university’s flagship professional development and networking experience, and share how it has evolved into a strategic platform for alumni engagement and donor cultivation.



Learn more

Register

Faculty-in-Residence

For six weeks beginning August 17 - September 25, Speaking Engagement welcomes Mallory Erickson — executive coach, creator and host of the What the Fundraising podcast, and author of the book by the same name — as our inaugural resident. We’ll have a final live Symposium event for members on September 23.

Learn More (Members)

Her central reframe: burnout isn’t a badge of honor, and it isn’t your fault. It’s largely systemic — the product of workplaces that expect too much with too little, and of work norms we absorbed early (first in, last out, always on, say yes to everything) that quietly trained us to live without boundaries.

The heart of the talk was her Honest Capacity Audit, a five-step framework (informed by Immunity to Change and Britt Frank’s The Science of Stuck): (1) name a draining behavior — say, checking email every night; (2) surface the “shadow incentive” — both what you gain by continuing it and what you fear if you stop; (3) calculate the “capacity debt” it’s costing you — the yoga class, the walk with the dog, the time with your kids; (4) set a micro-boundary, deliberately tiny so your brain accepts the change and builds a new pathway (e.g., no phone Wednesdays 6–7 p.m.); and (5) assess how it went — usually the feared consequences never materialize — then loop back and set the next one, chaining small wins into sustainable boundaries.

She closed with three tips: find an accountability partner (not your boss), work on one behavior at a time, and prepare for resistance — when others push back, remember it’s about them, not you.

Nobody who uses it can feel rejected. Nobody can feel guilty.

A student asks a question about breaking into consulting. The system finds a few alumni who might have something useful to say. If one of them is buried this week and lets it pass, the ask quietly moves to someone else. The student never sees the pass. The alum never sees the disappointment. The no leaves almost no residue.

Compare that to how most volunteer asks work. A mass email goes to 4,000 alumni looking for mentors. A few hundred open it. Forty respond. The other 3,960 did something we never account for: they said no, silently, and some of them felt it. Do that a few times a year for a decade and the silence starts to read like apathy. What it actually is: the residue of asks that made saying no expensive.

The deeper principle here isn’t guilt. It’s friction. Max’s design reduces the emotional transaction cost of participating. Institutions already spend enormous effort making yes easier: shorter forms, one-click RSVPs, prefilled gift amounts. Almost nobody spends effort making no inexpensive.

Designing away the sting also changes who gets asked. A cheap no means the system can safely route questions to alumni who have never been tapped, instead of leaning on the same proven volunteers every cycle. More people get a moment where the institution needed them specifically. More people get to imagine themselves as someone this place still calls on.

We measure opens, clicks, conversions, volunteers, mentors, gifts. We almost never measure what it costs someone to decline.

Maybe we should.

Max’s full conversation is on the Keynote feed July 27. The part about why helping someone can feel even better than being helped is worth the listen on its own.

Dave Hail is a fundraising strategist and storyteller who works with nonprofits and institutions to design stronger donor relationships and more effective engagement strategies. His work focuses on helping teams move beyond transactional communication toward systems that support long-term connection and growth.

His perspective sits at the intersection of strategy, systems, and storytelling, with a focus on helping organizations act with greater clarity and intention.

Dave is a lifelong learner, husband and dad, and lives in Oklahoma.

Big Themes This Week

• AI belongs in the background as a scaling mechanism, not out front as the selling point.

• The smallest act of kindness is often enough. Ask for five minutes, not an hour.

• Design so no one feels guilty and no one feels rejected. No just means not right now.

Team Discussion Questions

• Where are we asking alumni for more than they can give, when five minutes would do?

• Are we using technology to widen the door to connection, or to replace it?

• What in our process quietly makes people feel bad for saying no?

Upcoming: Faculty-in-Residence
Aug. 15 - Sept. 25

For six weeks beginning August 17, Speaking Engagement welcomes Mallory Erickson — executive coach, creator and host of the What the Fundraising podcast, and author of the book by the same name — as our inaugural resident.

Our Live (Members-Lead) Symposium with Mallory will be on September 23 from 11:30 am -12:30 pm ET.

Learn More (Members)

He started helping people with their resumes by hand, passing them around his own network and asking, do you have five minutes to help this person. And people did not just say yes. They came back asking for another one. “It feels amazing to make a difference in someone’s life,” he told me, and that discovery became the whole company. He turned to his partner and said he did not know how he would make money, but this was all he wanted to do. A decade later he still sounds like that.

Watch the full-length version on YouTube (52 mins)

That origin explains why Protopia is built the way it is. AI does the matching in the background so a connection that once took thirty minutes now takes three, but the technology stays out of the way, because the conversation itself is the point. Max is careful about what should never be automated, and his design reflects it.

Big Themes This Week

• AI belongs in the background as a scaling mechanism, not out front as the selling point.

• The smallest act of kindness is often enough. Ask for five minutes, not an hour.

• Design so no one feels guilty and no one feels rejected. No just means not right now.

Team Discussion Questions

• Where are we asking alumni for more than they can give, when five minutes would do?

• Are we using technology to widen the door to connection, or to replace it?

• What in our process quietly makes people feel bad for saying no?