How to do fun and interesting executive dinners, round tables, etc. - online and in-person

Here’s what I’ve learned in doing 30 (maybe more like 40?) executive events in person and online over the past four or so years. Over my career, I’ve done these on and off, but it’s become a core part of my job since moving to EMEA to support Pivotal and now VMware Tanzu with executives.

At these events, I learn a lot about “digital transformation,” you know, how people at large organizations are changing how they build software. But, below are some notes on what I’ve learned about doing the events themselves.

The events

These usually get together a of 8 to 12 people who’re up “upper management” and involved in changing organization structure, practices, and “culture” to get their groups better at software. They’re usually very large companies: banks/insurance, manufacture/pharma, government, etc.

We used to host dinners, in person to meet these people and tell them about Pivotal, now VMware Tanzu. These dinners were eight to about twelve people. You have pre-dinner drinks and hanging out, sit at a table and eat a meal (fish, meat, or chicken - usually very good from a luxury hotel kitchen), discuss “digital transformation” during dinner, and then have drinks on the bar with about four or five of the attendees who stay.

This doesn’t work when you’re in lock-down for two years now. So, we shifted to doing these events online. I’ve been the primary anchor - the entertainment, as it were - for something most of these in Europe that are in English.

When we started, we didn’t know if they were going to work or how and had to figure it out along the way. Now, we’ve got a good formula and here are some things that work:

  1. First, the format, or “run of show”: fun chit-chat as people join the meeting, an introductions round, the novel event, a short presentation to establish the topic and provoke some questions, open discussion, and then a thanks and tiny vendor pitch at the end.
  2. Do an introductory round at the start. Each person gives their name, title/role, what they’re working on, and most important what they’re looking to get out of the event. This is good for both parties (vendor and attendee) to get to know each other, and their interests good. It also comes into play in moderating the discussion at the end. For discussion in the group, this part is really handy because it lets everyone know what people will be interested in talking about.
  3. Have a “novel event,” a fun activity some kind that often involves something you’ve sent the attendees. For most of these, we’ve had a sommelier do wine tasting. We ship three little bottles of wine to each attendee and the sommelier walks through each wine for about 30 or forty minutes. The one we work with is fantastic, telling the history of the wine and the region it’s from more than the mechanics of drinking. We’ve also had beer tasting, and in the States they’ve done bourbon tasting. For Christmas we did gingerbread tasting. I once ran a Nutella tasting. A nice dinner is the “event” of an in-person round-table, and you need a hook for these online ones.
  4. Alcohol is a good ice-breaker and the best event to have. I don’t know what to tell you: it works and people appreciate getting free wine. The wine is good, but the stories and conversation around the wine get people’s in a sort of learning/thinking mode.
  5. For online events, have a PowerPoint. I use that word instead of presentation because it evokes the most cringe. For in-person events, interrupting a sit-down dinner with someone going up and presenting slides is practically taboo, and certainly weird. It just makes things too commercial and introduced a formal tone that messed up the conversation. But, online, things are very different. We ended up coming up with a 10 or 15 minute presentation that basically describes what good software development looks like with a few customer examples: “product, not project” to use one framing. I found that doing this is much less about discussing exact technologies (or “vendor pitching”), and more about level-setting what we’re going to be talking about, introducing topics and problems to discuss. It’s important to have at least one story that illustrates this point. The mechanic of this presentation is to say “this is what we’re talking about, here’s a language for it, and here is one example we can refer to.” Without a shared vocabulary and some anchors, you’ll end up spending all of your discussion time on definitions. This defines “the what,” the end goal that attendees are shooting for. Most people are struggling with “the how” of getting there. So, at the end I put up a list of common hurdles and problems. This is what drives the third part:
  6. Moderated open discussion about people’s challenges and successes in changing their organization (transforming). I end my little presentation with a list of about ~15 common hurdles. Then I ask people to share their stories, things that have worked, that they struggle with. Sometimes getting people to start talking is like pulling teeth. I’ve had to specifically call people out before. But, often there’s at least one person who will start with a story, e.g., “you listed finance as a problem. I agree, we are struggling with getting finance onboard with shorter development cycles and being open to changing plans.” At that point, people start talking, often even giving advice to each other. I love this part!
  7. After the first few comments, this is where I’ve forced myself to do actual conversation moderation. I say forced because, if you know me, you’d be shocked that I would be doing this - I don’t like talking with groups. I’ve learned to figure out the people who are talkers, the ones who are reluctant to talk, and to balance out the two. This requires two things: predicting a topic that someone could comment on and abruptly changing the topic of conversation, often by calling on someone new to talk. Predicting what people can talk about is usually drawn from the introductions, or past comments they’ve made in the chat. You don’t want two or three people to dominate the conversation, which is a common risk. So you have to draw people in. To do this, you can ask them directly to follow up, or you can just change the topic of conversation all the sudden and have them kick it off: “Those were some interesting comments on dealing with finance. Now, I’m interested in how you’re dealing with legacy systems. In the introductions, it sounded like the bank Alexandra works with had a lot of legacy systems: Alexandra, how have you been dealing with that?”
  8. At the end, you wrap up by saying “let me tell you a little bit about what we actually do and how you can engage with us more.” If you keep this to five minutes and thank everyone for showing up, it’ll be fine and not too “don’t do a vendor-pitchy.”
  9. In person events are slightly different. There is no presentation. Instead I have to sort of wing it and rather than being methodical and laying it all out (a presentation!), I just talk about what it means and looks like to do software better: the practices, an example story, what new tools make all this possible, and a few common hurdles. This generally works to get people to the open discussion, which is the goal of these get togethers. I’ve gotten a little rusty at this as all the events have been online for the past two years, but after a couple so far, I’m starting to remember how to do this.
  10. For in person events, I think it’s handy to have about 30 minutes of hanging out before things start, and even an event or some type. Most recently, we did a Formula One simulation game. An event is always fun and relaxes people, but all of this time also allows me to meet people and find out what they’re interested in. It’s totally workable (and not weird) to ask people what they work on and what they want to get out of this event. People will just tell you - and happily! And then you can start up conversations with them that you later draw on.
  11. Again, the goals of all of this is for people to get to know one another and learn from each other. You can do a surprising amount of that in 90 to 120 minutes. I think this is because people are genuinely interested and engaged/learning and because my co-hosts and I have learned how to moderate and drive conversations.
  12. Sometimes, instead of my short presentation, we’re lucky enough that to get one or two customers to speak. These are great, I usually I ask a few questions and sometimes the customer does a short presentation. We’ve had people from Audi, Rabobank, Daimler, Tesco Bank, Cerner, and other places. When you do this, you of course need to spend time with the person up front: not so much on content (you should let them talk about whatever they want however they want), but more just get friendly with them to set the tone of the meeting. And, of course, it’s a chance to meet and learn from someone new! Having a customer talk is always preferable, but rare to be lucky enough to get.

Behind the scenes

I don’t do much or the behind the scenes work for these, and it’s a lot of work. I’ve been very fortunate to have the support, belief, and, really, my ongoing nurturing/training from my co-workers who actually run all of this. My friend Hinada Neiron has done a lot of that work and she’s done a great job putting up with me and making sure I don’t slack.

Here’s the behind the scenes stuff that happens:

  1. Finding and recruiting the attendees. I’m not too sure how this happens as we work with an agency that helps us. They’re great at it. Also, sales people and inside sales people also try to recruit people. I haven’t done much work here: I think I got two people to show up. The problem here is that you’re trying to meet new people, so you need to find them.
  2. The agency also reminds people to show up and will call them if they haven’t shown up yet (like, on the phone!). This actually works well and brings in people who wouldn’t have made it otherwise.
  3. We spend a lot of time on the landing page/description of the event. At first, I thought this was too much, but I’ve come to realize that it needs to be near perfect because people you’re inviting don’t know us too well or what we do, so we need to get their attention and interest.
  4. It’s important to make notes and plan followup right after the last person leaves. It’s then equally important to talk directly with whoever it going to follow-up with customers. The goal of these events, on the vendor side, is meeting new people to start working with, so you have to push your people to do that.
  5. I send a thank you to all the attendees on LinkedIn, asking to connect with them. And, we of course send a thank you email.
  6. Ongoing, I think it’s good to discuss with the team what’s working and not working, to come up with new things to try, and always be trying to make things slightly different. You don’t want to get stuck doing the same thing every time, otherwise you won’t find new things that work even better. Also, it just gets boring if you’re not experimenting a little here and there.

My own transformation

Overall, these events are great. As you can probably tell by some of my comments above, it’s not natural for me to talk with groups of strangers, or even individuals. I go out of my way to avoid it on my life - I love self-checkout!

So, I was very worried about that at first, but with encouragement, just doing it over and over, and also experimenting with what works and doesn’t work, I’ve gotten over it.

Most of all, I’ve made sure I enjoy these events by talking about things I’m interested in and asking people whatever questions I’m curious about. You could call this “listening,” which I suppose it is. Several years ago when I was talking about this nervousness with my wife, she reminded me that I love talking about tech stuff, and learning about it…and that’s exactly what we talk about at these events! Once I realized that these were the kinds of conversations I wished I could have all the time and people I wanted to meet, it was easier to transform myself a little bit.

Anyhow, they’re good events, and I enjoy them. Hopefully I’ll see you at one of them!,, @cote,,