AI overload is real. The list of buzzwords is considerable: adoption, implementation, agents, agentic workflows, tools, context, memory, ethics, data protection, and on and on it goes. The vocabulary alone is challenging to absorb and keeping up with the ever-evolving AI tech space is a job in itself.

But, one thing is for sure. Used intelligently and with a clear outcome in mind, AI is a powerful enabler and capacity building tool that can give back time, which can be directed to the relationship work that advancement professionals do best.

For the past few years, and especially since moving into the consultancy and business ownership space myself, I have been using AI for a multitude of strategic and tactical purposes. However, one key insight has surfaced and remained consistent throughout — Humans first, AI second. Without the human creativity, judgement and direction, the AI does not deliver on relevance or quality.

For this article I wanted to test my thinking with some leading advancement practitioners and so I was delighted when brilliant colleagues Phillip Stork, Vice President, Future Students and Strategic Communications, of Griffith University in Australia and Rachael Green, Head of Alumni Engagement – Faculties, of the University of Nottingham (UK), agreed to share some insights into how their teams are deploying AI in advancement in two different parts of the world, and in two different advancement contexts.

Four common habits surfaced, in all our respective work applications.

1. Comprehensive CONTEXT

At the outset of my AI journey I allowed my LLM tool to interview me to generate what was called a context library (thank you Allie K Miller for the idea). It took a good half day of feeding responses to its probing questions. My business goals, my career goals, my life outside of work, one question at a time. The result, a repository of documents that the LLM could always draw upon when responding to my prompts of the future. I went all in on sharing, trusting in the process that better context (input) would mean better output. I was right, it was substantially better after the process.

Since then I have continued to build on that context. Continuously feeding market research findings in, showing the AI what good looks like to me through real examples from the marketplace (and my previous work), emails I have written, documents I have written. The more context the better. The output has continued to strengthen and responses coming back have been more relevant, personal and impactful.

Rachael’s team started in the same place. They developed a handbook of guidance to support how they manage their alumni email inbox. That context was then used to train Microsoft Copilot. “Historically, this was a full-time role in itself, but by training Copilot on our guidance and processes we’ve significantly reduced the time spent drafting responses”.

Phillip says communicators need “a clear set of key messages and overarching narrative before they start letting AI loose”. Another clear example of the importance of providing context first.

Context is not a one-off instance. At the end of each working session, I ask the system to consolidate what it has learned, to update our business system memory, update any agents’ capabilities (skills) and capture any outstanding tasks to my master task list (for later retrieval and action). This means the next conversation starts from a considerably improved state over the last and the context is ever evolving (and improving).

2. Allocation of the ROUTINE work

Phillip uses AI where volume is high. “We are using it extensively to support tier zero and one enquiries in our Current and Future Student Contact Centres, taking existing content and tailoring it to student needs…. We have also developed copywriting agents to support our marketing managers to produce consistent and student centric content for our websites, study guides and other student publications.”

At Nottingham it drafts replies for the alumni inbox and helps prepare volunteer communications, event plans, promotional copy, FAQs and briefing documents.

In my consultancy business it checks my daily emails, triages by importance and updates my CRM accordingly, surfaces important items on my daily dashboard and hands off to relevant agents in my team for further assessment and action.

A common thread: high volume, repeatable work, guided by something written down. Rachael’s team has its inbox handbook, Phillip wants key messages and narrative in place first and I use Standard Operating Procedures or Playbooks, so the AI understands how we do things for the routine work.

3. HUMAN JUDGEMENT is king

Phillip is direct: “Keeping a human in the loop in any personalised content, data analysis or copywriting is critical.” Phillip and his team do not use AI to make decisions. For him it is a way “to expedite repeatable or exploratory work.”

Rachael’s team uses AI to identify themes and highlight evidence when more than a hundred students apply for alumni volunteering opportunities. “AI can help identify themes, summarise applications and highlight evidence against predetermined criteria. When supported by a clear scoring matrix, it can be particularly useful in managing large applicant pools, helping my team quickly identify relevant experience, motivations and skills while maintaining consistency.”

Even so, she goes on to add: “All assessment decisions, scoring, judgement calls and final recommendations remain the responsibility of people, who provide the context, interpretation and accountability that AI cannot.”

In my context, I think of AI as a thought partner. It can support me in thinking through many opportunities and challenges in all aspects of my business, but the final decision always sits with me, drawing upon my 30+ years of professional experience as the foundation for that human judgement.

4. Check the OUTPUT

Phillip has seen it make mistakes: “I’ve seen a few examples where the AI tool has analysed the first few hundred data sets and then started to make assumptions.” His test is to: “treat the AI like you would an intern”, asking how it approached the task and what limitations it found.

Rachael’s team sees the same thing: “information is often presented with more confidence than it deserves.” Most of their corrections are “less about factual errors and more about tone, context and organisational knowledge that only a person would have.” On the alumni inbox, “AI proposes answers and pulls together relevant information, but staff still review, amend and approve every reply before it is sent.”

I run my own work through the same sort of process. Before anything is used externally, I put it through an agent within my team responsible for reputation management. That agent checks anything external against my brand intelligence guidance and surfaces any risk for my judgement. I also have guardrails set up that determines which folders or files that each agent can access and/or save to, and I have turned off the setting that allows my conversations to be used to train the provider’s models.

A useful set of words to improve an output can also be inserted into your prompt towards the end of a production schedule on an asset (email, agreement, analysis, report, presentation, copy etc). A simple ask for it to do a ‘red team critique’ and ‘conduct a blind spot analysis’ ensures you have run a more robust process. This has identified both excellent opportunities I may have inadvertently not seen, plus, saved me from some easy to miss mistakes on occasion.

Closing thoughts for practitioners

I asked both Rachael and Phillip what a team starting out should try first. Phillip’s advice, noted earlier, was to have the key messages and narrative in place first. Rachael’s answer was practical, “I’d start with low-risk, high-volume administrative tasks such as basic customer service activity (drafting simple emails with templates, summarising documents, preparing meeting notes, creating first drafts of reports and answering easy enquiries). These are areas where the efficiency gains are immediate and the risk is relatively low.”

From my perspective, I would add that AI is not always the solution. A useful framework I picked up from the AI Fluency Framework & Foundations course from Anthropic earlier this year was the 4d framework, which is a useful model for the application of AI:

* Delegation – what are you trying to accomplish? What can we handle ourselves and where can AI help? Recognise what AI can do well and not. This is about strategically choosing how AI fits into the process.

* Description – clear communication with AI. It needs detail rich conversations. What are you hoping or trying to achieve from the output? How the AI approaches the task and the context it needs for how you want it to work with you and the tone and style for the communication.

* Discernment – Thoughtfully evaluating what AI gives you. Are facts accurate, does reasoning make sense, do the recommendations align with my brand values and audience? Dos the output help me move forward. Develop judgement on recognising when it is good or not, or set aside entirely.

* Diligence – responsible AI interactions. How are you ensuring fairness and controlling for bias in a process? How is it verifying data? How am I being transparent in the use of AI? How am I being accountable and having ownership with the work with AI?

Humans first, AI second

The buzzwords will keep evolving and the technology will keep moving, but the principles above will remain for the foreseeable. Give AI comprehensive context (and continuously build on it), allocate the routine work and keep the human judgement and quality control top of mind at all times. By following these four principles, you can strengthen your confidence and capability in the deployment of AI in advancement.

Phillip and Rachael’s closing remarks give some good insights into their thinking for the immediate and near future.

“Just as digital became a foundation for all marketers about 15 years ago, the careful and considered use of AI is a critical skill I look for when hiring any marketers”.

Rachael added: “We’re experimenting in areas where we feel comfortable, learning what works and what doesn’t, and gradually expanding from there.”

I would be interested to hear about your own experiences, learnings and insights in deploying AI in advancement contexts across the globe.

Tristan Alltimes is a contributing editor at Speaking Engagement and the Founder and Principal Consultant of Alltimes Advancement Consulting (AAC).

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

What stuck with me is how much of this is a leadership and partnership problem, not a career-office problem. Andy credits a Wake Forest president who told every new faculty member to go meet the head of the career center, because their English and history majors needed to see their own way to the job market. And the model only works when career and advancement stop guarding turf and start multiplying each other, with advancement opening doors to alumni and parents as employers and the career team making those connections land. For a field that still parks career in a department off to the side, that’s the whole lesson. Career is everyone’s job, or it’s nobody’s.

Big Themes This Week

• Career services had to die to become a university-wide priority

• What makes students employable mostly lives outside the curriculum

• It’s a leadership and partnership problem, not a career-office problem

Team Discussion Questions

• Is career development layered across our student experience, or parked in one office?

• Where could career and advancement multiply each other instead of guarding turf?

• What would it take for our leaders to say out loud that this matters?

Keynote summary written primarily by AI

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

What stuck with me is how much of this is a leadership and partnership problem, not a career-office problem. Andy credits a Wake Forest president who told every new faculty member to go meet the head of the career center, because their English and history majors needed to see their own way to the job market. And the model only works when career and advancement stop guarding turf and start multiplying each other, with advancement opening doors to alumni and parents as employers and the career team making those connections land. For a field that still parks career in a department off to the side, that’s the whole lesson. Career is everyone’s job, or it’s nobody’s.

Big Themes This Week

• Career services had to die to become a university-wide priority

• What makes students employable mostly lives outside the curriculum

• It’s a leadership and partnership problem, not a career-office problem

Team Discussion Questions

• Is career development layered across our student experience, or parked in one office?

• Where could career and advancement multiply each other instead of guarding turf?

• What would it take for our leaders to say out loud that this matters?

Keynote summary written primarily by AI

Watch the full-length version on YouTube - 56 mins

DeVry has no homecoming, no tailgates, no nostalgia to lean on, so loyalty has to come entirely from continuing value. Deliver it persistently, Rich says, and the flywheel turns: graduates come back asking how they can help, and “we never have to make the ask.” For a field trained to appear at ask time, that is the whole lesson. Earn it first, every day, and the giving follows.

Big Themes This Week

• You don’t demand loyalty, you earn it through value

• Show up persistently, not just when something goes wrong

• Deliver value first and the ask takes care of itself

Team Discussion Questions

• When did our least engaged alumni last hear from us with no ask attached?

• What’s our version of catching the early signal before it becomes a problem?

• Where are we leaning on nostalgia instead of delivering ongoing value

Keynote summary produced primarily by AI

November Agora

Topic: Everybody’s Working for the (William & Mary) Weekend!

Date: Thursday, November 5 from 12 - 1 pm ET

Speaker: Kelly Holdcraft, Executive Director of Alumni Success at William & Mary

Kelly will detail William & Mary Weekend DC 2026 which featured nearly 50 events with more than half sold out, over 1,100 attendees, and 15 university schools and units represented over a four-day weekend. From a kickoff celebration with NFL alumni to an immersive MLB college game day to a presidential conversation on artificial intelligence to tours of our 90-foot coastal marine research vessel to a sold-out auction and more, the William & Mary Weekend offered once-in-a-lifetime intellectual, professional, cultural and social experiences to all who participated!

More details and register

Faculty-in-Residence

Topic: Faculty-in-Residence Symposium with Dr. Jay Dillon

Date: Tuesday, November 10 from 12:30 - 1:30 pm ET

Speakers: Jay Dillon, Ryan Catherwood, and SE Member Panelists

We’ll conclude this Faculty-in-Residence experience with Jay Dillon by hosting a round table discussion on the themes from Alumni Identity. The Symposium will be hosted by SE Publisher Ryan Catherwood, and led by SE Members.

More details and register

When I first began my last campus job, I had never led an alumni association board of directors. In actuality, I’d never led, managed, coached, or guided a volunteer board of any kind, or attended a meeting. My background was digital engagement. I was a total newbie on this front.

It quickly became my least favorite part of the job. I had so much anxiety in the run-up to meetings that I downloaded the Headspace app and started meditating. Part of the issue was circumstance. I learned right after starting the job that the incoming president of the board of directors was also my predecessor’s hand-picked successor, and I’d been selected instead of him.

To say we had a rough start working together would be an understatement. Thus, the meditation app. And it wasn’t just because the president hadn’t been selected for my job. My predecessor had been in the role for 41 years, and I was hired to do things differently. A mandate for change met my inexperience and other extenuating dynamics, creating a difficult situation I had to navigate.

But over time, the dynamics began to change. By the end of my tenure at Longwood University, I looked forward to my interactions with the board. Now, as I think back on that starting point and how things ended, I consider the shift I helped orchestrate one of the professional accomplishments I’m most proud of. I worked hard to create a vibrant alumni board experience for these highly engaged volunteers.

I thought I’d share eight strategies I tried while reflecting on those early, dark, frustrating days at the beginning, and how I created a productive, collaborative, and fun environment for the volunteers and the university by the end.

Deliver real wins. The reality is that nothing changed until I delivered clear wins. The biggest was executing a full-scale Alumni Weekend that had always remained out of reach. Once board members got to feel all the feels and sleep in the residence halls after fireworks, I gained momentum and began to earn their trust and respect.

Teach them what kind of board they are. The Longwood University Alumni Association was a separate 501(c)(3), but it had no employees, and the money that was brought in through royalty agreements didn’t cover the cost of their three meetings each year. It’s an example of an interdependent alumni association. I’m certain they didn’t realize the different models and the implications for the power they had and didn’t have. We often discussed our model specifically, and what that meant for how the board should think about supporting the Office of Alumni and Career Services, and not the other way around.

Narrow the mandate. When I first arrived, the board wanted to have a hand in every issue. They loved the school and wanted to make a difference in enrollment, retention, career outcomes, athletics, and philanthropy. We narrowed their impact area and focused on the board being the keepers of the university’s cherished traditions. This also aligned with the primary royalty revenue stream where they could make a difference: the class ring program.

Recruit by engagement, not friendships. When I first arrived in the role, an honest answer to the question, “How do I get to be on the alumni board?” was, “You have to know someone.” The board was selecting people from their friend groups. We built metrics and reporting with engagement scores, and I encouraged the board to first look at the highest scores and then at demographics. This ensured that the board members we invited were engaged in this new era and suite of programs.

Take money off the table — as much as possible. Over time, I deliberately gave the board less information about the overall budget. Instead, I brought in only the results of the class ring program and other royalty payments. I explained that the Office of Alumni and Career Services budget came from multiple sources, and it simply wasn’t part of their purview. They didn’t need to focus on annual budgets when the interdependent model simply didn’t call for it, and moving away from those conversations improved the experience for volunteers and staff.

Grow your future board. I always saw my role in moving the board forward to a better future state as putting “my people” on the board, who, of course, were those who were highly engaged with the initiatives of this new era and liked where the program was headed. I didn’t always get my way, but by the end of my tenure, most board members were aligned with my vision. I wanted to bring allies onto the board without abandoning the metrics-first approach.

Get out of the boardroom. One dynamic that created strong momentum was getting out of the boardroom and taking on different community service tasks. We spent time together at the local food bank and other nonprofits, where we could work together and have fun.

Make it a VIP experience. Building on the community service idea, we layered board meetings onto signature event weekends and hosted board receptions in different spots on campus and around Farmville. I wanted the volunteers to feel like being a board member was a VIP experience and one filled with joy and camaraderie with the other directors.

I’ll admit my focus wasn’t on creating a “working board.” My goal was to create more of a VIP experience for those who loved the school. I wanted the alumni board to feel like a culminating engagement experience for the university’s true “school color bleeders.” Yes, the board was helpful and functioned like an extension of our team in specific areas, but I did not need or want the board to feel pressure to get things done.

I made mistakes along the way, of course, but ultimately, I think back very fondly on many of those board members who made my tenure at Longwood University a positive one.

About Speaking Engagement

I’m beginning to assemble the SE calendar for the spring, and would love to hear from you on a few fronts:

1. Who are the movers and shakers you’d like to hear from on the Keynote?

2. Who have you heard present at a conference that would make a great Agora talk?

3. Are you interested in writing a guest article?

If you’ve got an idea or would like to contribute to SE, please let me know.

About the Next Keynote

On Monday, I’m sharing my interview with Andy Chan. Andy is the VP of Innovation and Career Development at Wake Forest University. We discuss his provocative TEDx talk from thirteen years ago called Career Services Must Die, and how things have evolved in the space. We also talk about experiential learning and what makes for great corporate partnership. A big thanks to Andy for sitting down with me for this convo.

Read more

For advancement, that reframes a familiar habit. Including a spouse in the room is not the same as treating her as a principal, and the sector’s instinct to close a “confidence gap” with literacy workshops misreads the problem. The piece calls it an authority gap, and the fix is not education but respect and engagement from the start, building a real, individual relationship with each partner long before any transfer forces the issue. The cost of getting it wrong is concrete: a donor who never felt seen in her own right rarely gives again once she is the one deciding.

The practical turn is to widen the frame. Ask how a donor makes decisions and who else is involved, whether that is a spouse, children, or an advisor, and bring those people into the life of the institution early, not just into the gift conversation. As the article concludes, the opportunity is not to prepare women for wealth as if they are late, but to redesign the conversation so they are no longer late.

Breakout summary created primarily by AI

November Agora

Topic: Everybody’s Working for the (William & Mary) Weekend!

Date: Thursday, November 5 from 12 - 1 pm ET

Speaker: Kelly Holdcraft, Executive Director of Alumni Success at William & Mary

Kelly will detail William & Mary Weekend DC 2026 which featured nearly 50 events with more than half sold out, over 1,100 attendees, and 15 university schools and units represented over a four-day weekend. From a kickoff celebration with NFL alumni to an immersive MLB college game day to a presidential conversation on artificial intelligence to tours of our 90-foot coastal marine research vessel to a sold-out auction and more, the William & Mary Weekend offered once-in-a-lifetime intellectual, professional, cultural and social experiences to all who participated!

More details and register

Faculty-in-Residence

Topic: Faculty-in-Residence Symposium with Dr. Jay Dillon

Date: Tuesday, November 10 from 12:30 - 1:30 pm ET

Speakers: Jay Dillon, Ryan Catherwood, and SE Member Panelists

We’ll conclude this Faculty-in-Residence experience with Jay Dillon by hosting a round table discussion on the themes from Alumni Identity. The Symposium will be hosted by SE Publisher Ryan Catherwood, and led by SE Members.

More details and register

By Dr. Jay Dillon, Chief Alumni Officer, UC Berkeley and Founder & Principal of Alumni Identity™

Early in my career at UCLA, I helped run one of the most fun events I’ve ever been part of. It was a young alumni reunion for everyone who had graduated in the past five years: a DJ, arcade games, a tiki bar, and thousands of recent grads back on campus. I wa…

Read more

Watch the full-length version on YouTube - 56 mins

DeVry has no homecoming, no tailgates, no nostalgia to lean on, so loyalty has to come entirely from continuing value. Deliver it persistently, Rich says, and the flywheel turns: graduates come back asking how they can help, and “we never have to make the ask.” For a field trained to appear at ask time, that is the whole lesson. Earn it first, every day, and the giving follows.

Big Themes This Week

• You don’t demand loyalty, you earn it through value

• Show up persistently, not just when something goes wrong

• Deliver value first and the ask takes care of itself

Team Discussion Questions

• When did our least engaged alumni last hear from us with no ask attached?

• What’s our version of catching the early signal before it becomes a problem?

• Where are we leaning on nostalgia instead of delivering ongoing value

Keynote summary produced primarily by AI

November Agora

Topic: Everybody’s Working for the (William & Mary) Weekend!

Date: Thursday, November 5 from 12 - 1 pm ET

Speaker: Kelly Holdcraft, Executive Director of Alumni Success at William & Mary

Kelly will detail William & Mary Weekend DC 2026 which featured nearly 50 events with more than half sold out, over 1,100 attendees, and 15 university schools and units represented over a four-day weekend. From a kickoff celebration with NFL alumni to an immersive MLB college game day to a presidential conversation on artificial intelligence to tours of our 90-foot coastal marine research vessel to a sold-out auction and more, the William & Mary Weekend offered once-in-a-lifetime intellectual, professional, cultural and social experiences to all who participated!

More details and register

Faculty-in-Residence

Topic: Faculty-in-Residence Symposium with Dr. Jay Dillon

Date: Tuesday, November 10 from 12:30 - 1:30 pm ET

Speakers: Jay Dillon, Ryan Catherwood, and SE Member Panelists

We’ll conclude this Faculty-in-Residence experience with Jay Dillon by hosting a round table discussion on the themes from Alumni Identity. The Symposium will be hosted by SE Publisher Ryan Catherwood, and led by SE Members.

More details and register

Watch the full-length version on YouTube - 54 minutes

It runs straight into how we measure. The four modes count what alumni do for us, not how known they feel by us, so Erin built a net known score: on a scale of zero to ten, how well does your alma mater know what matters to you right now? The move that follows is small and cheap, which is to stop asking for money first. She tells of a note with no ask that drew a reply in twenty minutes and, weeks later, a first-ever gift from someone who’d never given. The line I keep coming back to came from a birthday party, where a parent thanked the host for including them rather than inviting them. That’s the whole thing.

Summary of Keynote Article is Primarily AI-Generated

Big Themes This Week

• Alumni owe us nothing, which puts the work back on us

• We measure what alumni do for us, not how known they feel

• Recognition before the ask is the pipeline, not a detour from it

Team Discussion Questions

• If we put the net known score on our next survey, what would it say?

• Where are we leading with an ask when recognition would land better?

• What would it take to welcome our alumni in rather than invite them,

  ---

  November Agora

  Topic: Everybody’s Working for the (William & Mary) Weekend!
  
  Date: Thursday, November 5 from 12 - 1 pm ET

  Speaker: Kelly Holdcraft, Executive Director of Alumni Success at William & Mary

  Kelly will detail William & Mary Weekend DC 2026 which featured nearly 50 events with more than half sold out, over 1,100 attendees, and 15 university schools and units represented over a four-day weekend. From a kickoff celebration with NFL alumni to an immersive MLB college game day to a presidential conversation on artificial intelligence to tours of our 90-foot coastal marine research vessel to a sold-out auction and more, the William & Mary Weekend offered once-in-a-lifetime intellectual, professional, cultural and social experiences to all who participated!

  More details and register

One of the most challenging dynamics to manage on an on-going basis, particularly for medium- and large-sized institutions, is coordinating the central advancement unit with the colleges and schools. The relationship is often disorganized and can even become adversarial because deans and advancement leaders across eras have failed to build a synchronized engagement strategy. It’s like a pendulum slowly swinging between centralized and decentralized approaches.

Defining best practices for leading a fully coordinated, campus-wide approach to stakeholder engagement and external relations is often a topic in my consulting conversations with partners. After five years of client work with universities on this challenge, I believe there’s a clear framework all colleges and universities should pursue.

Introducing the 70/30 model

University advancement offices work to develop engagement events, programs, and volunteer initiatives. Most of these are pan-university initiatives, and stakeholders across the institution routinely participate. Think reunions, giving days, crowdfunding, homecoming, regional engagement, and digital engagement, including various technology platforms. I feel that 70% of engagement at any institution should happen through these initiatives.

Academic deans should first consider how they’re promoting and using these opportunities as the focal point of their engagement strategies, ideally before developing any separate and distinct initiatives. College- or school-based engagement can be layered on top of a pan-university initiative.

At the same time, 30% of engagement should be college- or school-specific, and contain the unique characteristics and personality traits of those entities. There is a need for individual colleges to build and execute their own engagement strategies. College deans and faculty build special relationships with their stakeholders, and many alumni meet lifelong friends through their academic coursework.

When metrics are missing

One of the most common dynamics I help schools work through is that, because central advancement hasn’t built a system to track engagement and report on engagement, develop a scoring methodology, and set measurable goals, a knowledge gap creates mistrust.

Every centrally-led engagement initiative attracts alumni with degrees from across the university. It happens every day; advancement engages graduates from colleges, schools, and faculties (if you’re in the UK or Australia). The problem is a lack of reporting. There’s no scorecard. There’s no hot list report of activated donors containing evidence that university advancement is providing this key service already.

That’s when academic deans throw up their hands and chart their own course.

What academic deans want isn’t control over engagement programs; it’s proof that what advancement is doing is working.

Staffing should support the 70/30 model

The first step in creating a stronger partnership between advancement and the colleges, schools, and units on any campus is to come together for strategic planning, then develop a top-notch approach to metrics and analytics. Facilitating buy-in and ongoing collaboration requires these two steps.

After that, the trick is to figure out how to staff the model. I struggle with the “college engagement officer” concept. It’ll be the subject of a future newsletter, but assigning an individual, often at an entry-level career stage, to coordinate this model, which ultimately must increase trust between senior campus leaders, seems like a tall ask. These positions change over constantly, and they position early-career engagement professionals as liaisons who must also be capable event producers, volunteer managers, and experienced communicators.

Senior leaders need to stop the pendulum and work together

The biggest hindrance to building a successful, coordinated, campus-wide engagement program is the lack of a plan, missing metrics, and senior leaders often handing relationship-building off to early-career colleagues.

A junior colleague can coordinate logistics, but they can’t really build trust between a dean and a vice president or even AVP-level leaders, and it isn’t fair to ask them to. Stopping the pendulum is senior leaders’ work, and it’s ongoing.

But it’s hard to overstate how important metrics are. Academic leaders build careers on research, which must be quantifiable. When engagement pros can’t provide evidence that their approaches increase participation, everything breaks down, and trust erodes. Success begins when academic deans can hold, or receive in their inbox, regular updates on stakeholder engagement and insights into how and with whom they should spend time.

The institutions that get this right treat the 70/30 model as a shared commitment, not a split to relitigate every time leadership turns over. They agree on the balance, govern to it, and let the analytics light the way. That is how what is sometimes a fractious relationship becomes one that picks up steam and starts getting wins chalked up.

As always, I’d love your comments!

About Speaking Engagement

We crossed the 500 subscriber mark this week! I’m really proud of how far SE has come over the last few months. I continue to receive positive feedback. It’s been a grind at times, but when I hear from folks that they find this resource valuable, that makes it all worth while.

To celebrate this milestone, I’d offering the opportunity for each member to gift one free six-month membership to a friend or colleague.

Refer a friend promo is through Nov. 6th, with free access ending April 30, 2027

Step 1: Ask a colleague at another institution if they’d like free members access to Speaking Engagement through April 30, 2027. Feel free to send a link to this info sheet.

Step 2: Once you get confirmation they are interested in a free six-month membership, send them this form to fill out.

I’ll batch upload all referees to Substack on Friday, Nov. 6th and will confirm access.

About the Next Keynote

I try to bring lots of different opinions and angles to Speaking Engagement. On the Keynote pod I’ll be sharing on Monday, my special guest is Rich Korczyk, Chief Experience Officer at DeVry University. DeVry is an almost 100 years old and they’ve been helping adult learners reach their professional goals for a very long time. Rich is a true expert in engagement and experience design. I know you’ll enjoy this convo. Tune in!

Busteed challenges a familiar myth, that the size of an endowment signals the quality of a student’s experience. It does not. What predicts a strong experience…

Read more

Busteed challenges a familiar myth, that the size of an endowment signals the quality of a student’s experience. It does not. What predicts a strong experience is far simpler: whether a student had a job or internship that mattered. Yet internships remain a weak spot, too few to go around and easiest to reach for students who already have resources and connections. The panel kept returning to the idea that the work has to be personal, and that advancement can help close the gap, whether by funding internships directly or by rethinking what a future endowment could be built to support.

Roth names the other half. Amid AI and a harsh job market, he argues that college still teaches people how to learn, and how to be human, and that using AI to skip the hard work means learning less. Where the two pieces meet is what binds alumni for life: the ability to trace one’s success, and one’s growth as a person, back to the place that shaped them. The job for advancement is to build those connective threads on purpose, and tell the stories well.

• Rod Danan, “Internships Beat Majors,” a conversation with Brandon Busteed (The Unpulled Lever, E4): https://www.linkedin.com/pulse/e4-internships-beat-majors-brandon-busteed-ceo-edconic-rod-h-danan-elq8e/

• Michael S. Roth, “Three Cheers for Students Starting College,” The New York Times (opinion), September 4, 2026: https://www.nytimes.com/2026/09/04/opinion/college-freshman-education.html

Breakout summary created primarily by AI

Alumni engagement work is not for the faint of heart. I remember many travel weekends during football season where we’d get up at some ungodly hour to get the early flight out of Seattle, hit the ground running (sometimes literally) by heading to meet with alumni and donors for lunches and coffees, fit in a quick site visit, host an event that night, ge…

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Watch the full-length version on YouTube - 54 minutes

It runs straight into how we measure. The four modes count what alumni do for us, not how known they feel by us, so Erin built a net known score: on a scale of zero to ten, how well does your alma mater know what matters to you right now? The move that follows is small and cheap, which is to stop asking for money first. She tells of a note with no ask that drew a reply in twenty minutes and, weeks later, a first-ever gift from someone who’d never given. The line I keep coming back to came from a birthday party, where a parent thanked the host for including them rather than inviting them. That’s the whole thing.

Summary of Keynote Article is Primarily AI-Generated

Big Themes This Week

• Alumni owe us nothing, which puts the work back on us

• We measure what alumni do for us, not how known they feel

• Recognition before the ask is the pipeline, not a detour from it

Team Discussion Questions

• If we put the net known score on our next survey, what would it say?

• Where are we leading with an ask when recognition would land better?

• What would it take to welcome our alumni in rather than invite them,

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  November Agora

  Topic: Everybody’s Working for the (William & Mary) Weekend!
  
  Date: Thursday, November 5 from 12 - 1 pm ET

  Speaker: Kelly Holdcraft, Executive Director of Alumni Success at William & Mary

  Kelly will detail William & Mary Weekend DC 2026 which featured nearly 50 events with more than half sold out, over 1,100 attendees, and 15 university schools and units represented over a four-day weekend. From a kickoff celebration with NFL alumni to an immersive MLB college game day to a presidential conversation on artificial intelligence to tours of our 90-foot coastal marine research vessel to a sold-out auction and more, the William & Mary Weekend offered once-in-a-lifetime intellectual, professional, cultural and social experiences to all who participated!

  More details and register

(Listen to the full-length version on YouTube 58-mins)

Underneath that instinct is a lot of unglamorous craft. He starts every event with roughly twenty questions before anyone talks about flowers. He’ll tell you the staffing plan matters more than the centerpiece, because “if you can arrange staffing correctly at an event, it doesn’t matter if the florist brought the wrong color flowers.”

And then the line that outlasts the whole conversation: traditions need a purpose. UVA keeps its traditions by letting them adapt, turning thousands of graduation balloons into a cohort that collects them for the children’s hospital. A tradition is only worth keeping as long as it still means something to the people living it now. The best events, like the best traditions, aren’t monuments. They’re built, every time, around the people in the room.

Big Themes This Week

• Design the room around the guest, not the venue

• Staffing and attention beat decor every single time

• Traditions survive only when they still serve the people in them

Team Discussion Questions

• Which of our events are quietly planned for the space instead of the people in it?

• If we had to name the five people who must leave each event feeling seen, who are they, and who’s responsible for making it happen?

• Which tradition are we protecting out of habit, and what purpose would justify keeping it?

Summary of Keynote is Primarily AI-Generated

November Agora

Topic: Everybody’s Working for the (William & Mary) Weekend!

Date: Thursday, November 5 from 12 - 1 pm ET

Speaker: Kelly Holdcraft, Executive Director of Alumni Success at William & Mary

Kelly will detail William & Mary Weekend DC 2026 which featured nearly 50 events with more than half sold out, over 1,100 attendees, and 15 university schools and units represented over a four-day weekend. From a kickoff celebration with NFL alumni to an immersive MLB college game day to a presidential conversation on artificial intelligence to tours of our 90-foot coastal marine research vessel to a sold-out auction and more, the William & Mary Weekend offered once-in-a-lifetime intellectual, professional, cultural and social experiences to all who participated!

More details and register

A few newsletters back, in the one titled The Main Character and the Understudy, I mentioned, almost in passing, that to reduce the internal dynamic that development matters more than alumni engagement, VPs should hire their own freelance or agency partner for development communications. It was a quick aside that needs more discussion, so I thought we could game this out a bit more: why it’s a critical move for today’s advancement shops.

We live in a totally different communications landscape than we did even a few years ago, and it’s constantly changing. But what hasn’t changed is that, to succeed, advancement leaders must capture and sustain alumni and donor attention through ongoing, strategic, communications-based engagement. It’s hard to get attention. Once we have it, even a little, we want donors to get involved and keep them involved as contributors over a lifetime. Messaging and conversions must be connected across every piece of content and experience.

So where have alignments failed to keep up with the attention economy, and where is that holding most advancement teams back?

Experiences should live downstream from communications

At the colleges and universities I consult, the most damaging dynamic to progress is a communications-as-a-service model. The individuals best equipped through skill and experience in capturing attention and designing strategies for donor journeys throughout the year are bogged down taking orders from development and alumni relations colleagues whose work should live downstream from the messaging.

This is the whole kit and caboodle, as my grandfather would say. We tend to treat communications as the thing that advertises the experiences and the programs. To meet the moment, we need to flip the script and say that communications builds and carries the event, volunteer experience, and the story. It’s what brings it all together. Without the connecting narratives, everything is just activities on a calendar, and we get the siloing that plagues so many teams. That is why I feel experiences should be downstream from communications, not the other way around.

Communications makes the other three CASE modes work

Communications is one of the four CASE modes, but the other three (Experiential, Volunteer, Philanthropy) require excellence in marketing and communications to be successful or even relevant.

But think about it from a tracking-of-activity standpoint. We want to track and measure communications-based engagement, like email click-throughs and LinkedIn followers, as much as possible, but we also need strong multi-channel marketing to advertise our events and scalable volunteer programs. In fact, there’s an entire experience brand to create and maintain that tells the story of involvement over a lifetime — from prospective student to graduate — that must be told by the advancement communications team.

Communications must be resourced to connect the dots effectively across the donor journey.

Free communications from one-to-one production

Any advancement leader who cares about showing ROI on strategies and tactics, and whose communications team is set up primarily to respond to production demands from other units within the division, is dramatically underserving both the needs of the current economy and sacrificing real opportunity to stimulate generosity.

Removing development-related, repetitive one-to-one tasks that require more design-level personalization from the core communications teams is an important part of creating more integration, not less. Proposal development, personalized stewardship, visit leave-behinds — all the materials that the major gifts team might need should go to a trusted freelancer or agency partner.

Here’s the thing: this is absolutely critical work. A healthy budget should go toward creating memorable experiences for our donors. Communications must be well-resourced; this is different work from devising internal and external messaging, developing campaigns, and connecting engagement initiatives.

Resource communicators as strategists first

For many alumni, communications is the only way they stay involved with their alma mater. Even highly engaged donors stay connected most of the year through communications, not through events or visits.

Advancement communications must be staffed and resourced, not necessarily with full-time employees, to operate with an annual messaging view and focus on conversions. This same group of individuals cannot also create new proposals, donor briefs, and stewardship projects. Maintaining a broader view of brand and messaging creates the space needed to build buzz around a campaign and design the storytelling apparatus.

The first step to owning a bigger piece of the attention economy is to create the bandwidth for communications teams to actually be strategists first, production support second. The only way to do this is to free up bandwidth by outsourcing a different part of the donor experience. It’s not just about freeing up time; it’s a philosophical shift that requires bringing communications into strategy planning and discussion early because content and messaging connect all opportunities to participate and contribute to the life of the institution.

When you free communicators from production and put them at the center of strategy, they become the team that spans the entire donor relationship and serves as the connective tissue between the experience and the ask. That continuity is what the donor experiences as the journey.

About Speaking Engagement

I’m using this section to call out the next Agora coming up on Thursday, November 5th at 12 pm ET featuring Kelly Holdcraft, Executive Director for Alumni Success at William & Mary. Kelly will present about executing W&M Weekend — a signature event in May that was held off-campus in Washington, DC. Kelly will share what they did, what they learned, and what she’d advise to any college or university thinking about a similar endeavor.

Join me and a great group for this Agora. We’ll follow Kelly’s TED-style talk with a moderated networking session on relevant topics.

Register

About the Next Keynote

On Monday, I get to share my interview with Erin Essak Kopp. Erin is an engagement strategist with experience in shops like Ohio State, University of Oregon, and Ohio University. More recently, Erin has built and launched Spark Plug — a new technology company that’s helping teams reach alumni and donors at the right moment. Erin and I talk it out on this episode and dig into the challenges facing alumni engagement professionals and how to meet the current moment.

What does it take to build a regional event weekend so good that alumni block their calendars a year in advance? So good that your president, your deans, your boards, your faculty, and your alumni all want a seat at the table, both to help plan it and to be part of it?

That is the question Kelly Holdcraft is going to answer at our next Agora.

Over the past decade, William & Mary has run five regional signature weekends in DC, New York City, Chicago, and San Francisco. These are not your typical regional receptions. They bring the best of the institution, its distinguished faculty, its network of Tribe faithful, and its unmistakable spirit of discovery, into iconic settings for a few days of connection, discovery, and celebration.

The numbers from William & Mary Weekend DC 2026 tell the story. Nearly 50 events, more than half of them sold out. Over 1,100 attendees. Fifteen schools and units represented across four days. The programming ran from a kickoff celebration with NFL alumni to an immersive MLB college game day, a presidential conversation on artificial intelligence, tours of W&M’s 90-foot coastal research vessel, and a sold-out auction. Once-in-a-lifetime experiences, intellectual, professional, cultural, and social, for everyone who showed up.

If you are thinking about regional signature events, wrestling with how to get campus partners to actually show up, or trying to figure out how to structure a big volunteer committee without it falling apart, this is the session for you.

Join us:

Register

Thursday, November 5, 2026 at 12:00 PM Eastern
Featuring: Kelly Holdcraft, Executive Director of Alumni Success, William & Mary

See what they built at weekend.wm.edu, then come hear how they actually did it. Block your calendar and bring your questions.

After Kelly’s presentation, we will break into smaller groups to talk through how these ideas apply at your own institution.

(In this clip, Kathryn shares the importance of alumni volunteers at Life at Elon.)

There’s a lot of relationship development happening. These programs are doing something about isolation and intergenerational distance that no four-year model touches, at least as they’re designed today, and it’s part of advancement at these schools and others, where the instinct is to measure everything in gifts. Both directors were careful here: the giving is real, but it follows the relationship, it never leads it. We talk during this session about the degree of integration that could or should be part of lifelong learning programs.

Text primarily written by AI

November Agora

Topic: Everybody’s Working for the (William & Mary) Weekend!

Date: Thursday, November 5 from 12 - 1 pm ET

Speaker: Kelly Holdcraft, Executive Director of Alumni Success at William & Mary

Kelly will detail William & Mary Weekend DC 2026 which featured nearly 50 events with more than half sold out, over 1,100 attendees, and 15 university schools and units represented over a four-day weekend. From a kickoff celebration with NFL alumni to an immersive MLB college game day to a presidential conversation on artificial intelligence to tours of our 90-foot coastal marine research vessel to a sold-out auction and more, the William & Mary Weekend offered once-in-a-lifetime intellectual, professional, cultural and social experiences to all who participated!

More details and register

(In this clip, Kathryn shares the importance of alumni volunteers at Life at Elon.)

There’s a lot of relationship development happening. These programs are doing something about isolation and intergenerational distance that no four-year model touches, at least as they’re designed today, and it’s part of advancement at these schools and others, where the instinct is to measure everything in gifts. Both directors were careful here: the giving is real, but it follows the relationship, it never leads it. We talk during this session about the degree of integration that could or should be part of lifelong learning programs.

Text primarily written by AI

November Agora

Topic: Everybody’s Working for the (William & Mary) Weekend!

Date: Thursday, November 5 from 12 - 1 pm ET

Speaker: Kelly Holdcraft, Executive Director of Alumni Success at William & Mary

Kelly will detail William & Mary Weekend DC 2026 which featured nearly 50 events with more than half sold out, over 1,100 attendees, and 15 university schools and units represented over a four-day weekend. From a kickoff celebration with NFL alumni to an immersive MLB college game day to a presidential conversation on artificial intelligence to tours of our 90-foot coastal marine research vessel to a sold-out auction and more, the William & Mary Weekend offered once-in-a-lifetime intellectual, professional, cultural and social experiences to all who participated!

More details and register