Professional Development for the Rest of Us

September 12, 2026

I spent the last couple of days in Chicago at Tech & Learning’s EdExec Summit, and I am exhausted. Not bad exhausted. The kind of exhausted that comes from two days of conversations, sessions, dinners, introductions, debates, catching up with old friends, meeting new ones, and trying to squeeze one more conversation into a day that ran out of hours a long time ago.

I’ve been involved with Tech & Learning’s EdExec Summit for the past three years and have had the opportunity to serve on its advisory board, helping provide feedback as the event has evolved. Going into this year’s Summit, I was thinking a lot about the professional development available to those of us who work in education technology. Coming out of it, I’m thinking even more about something much simpler. There is still enormous power in getting people in the same room.

There is an interesting irony in EdTech because a lot of us came from education. When I was a teacher, principal, and district administrator, professional development was simply part of the job. We had certifications to maintain. We went to conferences. We participated in professional learning communities. We had mentors. We were expected to keep learning because the profession expected us to keep getting better.

Then some of us moved into education technology. The responsibilities got bigger. The decisions involved millions of dollars, employees, investors, products, customers, and potentially millions of students. Yet somewhere along the way, structured professional development became much harder to find. There are plenty of conferences, sales events, and places to meet customers. There aren’t nearly as many places designed specifically to make education technology leaders better at leading education technology companies.

That distinction is one reason I’ve been such a believer in what Tech & Learning is trying to build with the EdExec Summit. There is always pressure to turn an event like this into a go-to-market opportunity, and I understand why. If a company is paying to fly an executive to Chicago, put them in a hotel, and take them away from the business for a couple of days, somebody understandably wants to know what they’re getting in return. Customers are there. Relationships get built. Some of those relationships may eventually lead to business. But I hope we resist the temptation to make that the point. Sometimes the ROI is simply getting smarter.

We covered some significant issues this week. We talked about the financial pressures facing education companies, the screen-time debate, evidence and efficacy, and how all of those things are changing the market. I led a conversation about something I’ve become increasingly interested in, evidence as go-to-market. It isn’t enough to say your product works anymore. Increasingly, companies need to understand how proving that it works becomes part of the way they build trust with the market.

Those were important conversations, but I’m not sure they were the most valuable part of my trip. For me, some of the best professional development happened between the professional development.

It happened over meals, in hallways, over a drink, walking from one place to another, or sitting down with someone and realizing the 15-minute conversation you planned has somehow become an hour. I had younger leaders reach out before the Summit and essentially say, “Are you going to be in Chicago? I’ve got some things I’d love to talk through with you.” At the same time, I was reaching out to people who have been doing this longer than I have and asking for exactly the same thing.

After nearly 30 years in education and technology, that may be the network I value most. These are the people you can call six months from now and say, “Here’s what I’m dealing with. Have you ever seen this before?” Often, they have. They’ve seen the movie before.

Sometimes that person is another operator. Sometimes it’s an investor. Sometimes it’s a superintendent or technology leader who sees your company from the customer’s side. Sometimes it’s someone working in policy who understands something happening around the corner that hasn’t hit your radar yet. Getting all of those perspectives in one place is incredibly powerful because the person across from you doesn’t necessarily have to give you the answer. Sometimes they just get you far enough out of the weeds to ask, “Have you thought about it this way?”

I think that is also how professional development changes as your career progresses. Earlier in your career, you may need the course, the framework, or the person standing at the front of the room. Later, the most valuable learning is often much more immediate. You have a real problem, a real decision, and a handful of people you trust enough to call and ask, “What am I missing?”

After nearly 30 years, I’ve been around enough corners that people sometimes call me with those questions. Just as importantly, I still have people I call because they’ve been around corners I haven’t reached yet. I hope that never changes. The moment we decide our experience means we no longer need people challenging our thinking is probably the moment our experience starts becoming a liability.

Maybe that’s also why I left Chicago thinking about an idea I’ve been kicking around for a while. What if we stripped away most of the traditional conference and brought six or eight education technology executives together at Halcyon Ranch for a couple of days? No giant exhibit hall. No racing from session to session. No expectation that somebody needs to leave with a pipeline report to justify the trip.

Instead, everybody brings one or two genuinely difficult business problems they’re trying to solve. We spend some time working and some time outside. We eat well. Maybe we bring in a superintendent, investor, or another leader who sees the market through a completely different lens. And at the end of the day, we sit around a fire and have the kinds of conversations that normally get squeezed into the 20 minutes between conference sessions.

I don’t know exactly what an EdTech Ranch Retreat looks like yet. Maybe that’s part of the fun. But after the last couple of days in Chicago, I’m more convinced than I was before that we need spaces like that. We need opportunities to get out of our companies, out of our lanes, and sometimes just out of the weeds long enough to think with people we trust.

Technology keeps making it easier for us to connect. AI can give us an answer in seconds. Zoom can put ten people on a screen from ten different cities. Slack can keep us connected all day long. All of those things are valuable, but none of them quite replicates what happened in Chicago this week.

Sometimes you still need to get in the same room.

Or maybe, every once in a while, around the same fire.

Who’s in?