I’ve hosted a lot of executive dinners for work - maybe 50 or 60 over the past several years…? These are commercial oriented. At my work, we’re trying to meet new people to sell our software to, or people who know people, etc. Getting to know “executives” is directly related to the sales process. The secondary goal is more brand and thought-leadership marketing: just making the attendee aware of us and what we do, and, hopefully, our “vibe.” And the priorities after those two are what you’d expect: networking, fun/useful conversation, and doing some overall “community management” and participation.

Here’s some behind the curtain stuff on doing them, especially targeted at people like me who don’t like group conversations. I’ll skip over the “sales” tactics I use1 and creating the “content strategy,” and just focus on getting a good conversation going and structuring the at-table event. “Surviving moderating an executive dinner,” so to speak :)

Here’s what I try to do, big picture:

1. Have some kind of five to ten minute “talk” that defines a topic. With me, this is usually discussing agile development, DevOps/platform engineering, etc. In the last one I did I threw out the topic: “you should centralize and standardize the platform your app developers use.” That was a good one!

2. Find a problem with that topic, especially the “it depends” kinds of implementation topics. One of the problems with the centralize platform thing was: the developers don’t like it, and won’t use it.

3. Ask people what they’ve encounter, done, or found.

4. Get them in a conversational fly-wheel, all talking and exchanging ideas with each other as peers.

To do this, you have to bootstrap the group into talking and then maneuver things to make sure they keep sharing, and asking each other questions: monitor and spin the fly-wheel when it starts to slow down.

This is all difficult for me because I don’t really like talking with/in groups, so I have to force myself to be involved rather than just sitting back and listening. I love just sitting back and listening.

My introverted self believe this is all impossible. But, it’s totally possible: they all want to talk, listen, and exchange ideas…to learn - that’s why they came!2 - but usually they need help getting going.

What is an executive dinner

If you don’t know what an executive dinner is it, here’s what it is. First, it’s hosted by someone who has a commercial interest in the attendees. In my case, we’re looking to sell Pivotal/Tanzu products and services that help companies build and run their software.

You find some decision makers (they have needs and budgets) at companies that you want to sell your stuff to. You invite them to a sit-down dinner in a private room of a fancy restaurant.3 Everyone sits at a big table so they can see and (mostly) hear each other. The dinner lasts for 2 hours or so. People talk during the dinner. That’s what it looks like from the outside.

It’s like really high-touch, really-expensive lead-gen. I’ll cover the goals inline below.

(And, hey, I’m being totally transactional and mercantile here. Cold-hearted, HA HA! BUSINESS. It’s also possible, encouraged, and necessary to just be chill and, like, human. But, let’s focus on the business part.)

Finding things to talk about

In the at-the-table conversation, it’s good to call on people who will have something interesting to say, and be on topic. But these people are strangers, so you don’t know who those people are per topic. Here’s a trick that. Often, you have a pre-sit-down “cocktail” party as you wait for people to show up (like a 30 minute windows). People stand around, get drinks, and eat tiny food.

During this time, you move around the room and just get to know people.4 The good thing is, they all came for a topic and will want to talk about. You can just dive right into that topic, it’s not like fishing for topics at a playdate with mixed normals.

I usually ask people “what do you do [at work/in subject matter area]?” They’ll give a long answers! “Well, I’m the director of application development, so oversee three teams that work on our customer facing loan app.”

Next, I either ask them to:

1. Clarify things I don’t understand5 - “whoa - what does ‘generative cyber-analytical responsiveness’ mean?”

2. I ask for some more detail - “what kind of methodology do you use?” “Oh, why do you run on public cloud?” “Is Google Cloud good? Why not Azure”)

3. Or, I just say “is that fun?”

The last question usually throws people for a loop, and they have to stop and do some original thinking, breaking out of the usual small talk pattern. And from there, you just ask questions about why it’s fun or not. This usually evokes problems and challenges, or victories and success they have. And, the “is it fun” question also downshifts the conversation from professional to more whimsical.

So, you walk around and talk with three or five people in this pre-event. Now, you know three or five people who can talk about some topics. During the dinner conversation, you call on those people when the topics come up (or when cold-start bring the topic up), and you know that they have something (interesting) to say. “On that topic, Geraldine: we were talking about the challenges of managing 50 plus SKUs in the salty snacks industry earlier. What have y’all been doing to make that better…and does it work?”

Keep “intros” very short

Everyone is sitting, and you have to start. The main thing I’ve learned to avoid is having each person do an open-ended introduction. You need to know who each person is, but you have to really make people keep it short. Some people’s introductions include their “life story,”, and can extend to 5, even 10 minutes if you don’t manage it. Asking “what brought you here?” usually evokes a lengthy response. And these lengthy intros snow-ball: once one person gives an extensive into, the next people start modeling them and giving long intros. So, if you have 8 to ten people to go through, you’ve blown 10, even 15 minutes of time.

You can avoid this by not asking people to say what their interest in the topic is, this usually results in two or three people telling you everything about their involvement and experience in the topics, which can be 5+ minutes which ads up. It’s risky to ask them what they’re interested in hearing, but worth it to get topics on the table that you can refer to when boot-strapping.

I try to be blunt: “let’s go around and introduce ourselves, but keep it really short so we can get to talking: tell us who you are, where you work, and just briefly what you’re interested in hearing from the group [maybe even just one thing].”

Now, there’s a trade off you’re making here. Your sales people would love to hear an extended list of wants, needs, and problems that each person has. A huge point of these events is to do a lot of sales intelligence gather all at once, and knowing people’s background and examples of what they do is very useful for qualification and structuring “customer journeys,” etc.

Moderating - keeping things conversational

About ten or 15 minutes in, you have to watch for things turning into a series of lectures from individuals. People will just give “readouts” about a topic. You might also get people who are the “let me solve this problem once and for all,” dead-ending into a conclusion rather than people doing structured shooting-the-shit. In general, you just have to let that person sort of run, and then immediately call on someone else to share their experience, or change the topic. Another tactic for the readout people is to be like: “that sounds great, but how do you get people to decide to actually do it?”

Sometimes, only a few people talk. You want “most everyone” talking. So, you have to call on people who aren’t talking. Like, just specifically on a topic: “what do you think?” - “has that been your experience?” - etc. Or, you can try to bring the conversation back to the table by saying things like “what are the rest of you experiencing/doing?”

Sometimes the conversation stalls out, and then you have to do talking. Have some 2-3 minute monologs ready. I don’t have first hand experience most of the topics at these dinners, so I go over what other people have told me, things I’ve read, etc. When you’re re-starting the conversation, you have to do the “say something that can be objected to” thing, and then ask people what their experience is.

Another trick for managing the conversation flow, is timing the meal courses. We try to have the main conversation before the food (appetizers) is brought out. Group talking while you’re eating is hard.

Having the serving staff bring in food 15 minutes after you sit down gives you a natural hard stop: you can time box the focused, group conversation, and when the food shows up, transition to side conversations.

That shift usually happens when the entree is brought out. In the appetizer phase, you’re slowing down the single thread group talk, and people are starting to talk in pairs and small tuples. This transition kind of takes over the table, and then you have lots of little conversations going on, which is my goal for the rest of the dinner.

Ending it

Closing out depends on what you want. Eventually you need to announce the formal end of the event, and throw out a “what’s next”/call-to-action. In our sales focused dinners that means saying “hey, this was great! We’re here to talk about how we solve these problems, so feel free to talk with us more.”

I don’t like the retro/summing up/what’s your take away thing like you might do at work. That’s just extra work you’re asking people to do, and also it’s usually lame, and no one’s going to do anything with it (probably).

At the end, do your CTA, just thank people, and close out. Also, people are both tired, full, and maybe booze-buzzed - not the best time for “read outs.” I used to hang out after as people moved to the bar. But, following the Ann Richards Evening Activities Principle (roughly quoted: “well, y’all, I’m leaving now, because nothing interesting/useful/good happens after 9pm”), I usually leave. Sales people sometimes stick around.

Also, sometimes it just doesn’t work. This especially true if you have free-loaders, cynics, and too heterogenous of topic areas/SME’s. When that happens, wherever: you usually met 1 or 2 people that are interesting.

Oh, and the organizing it part is a whole other thing that I don’t have a lot of experience with. We use agencies for that. They have big lists of people, and the other thing they do is gently encourage people to show up. They’ll call them the day before, and sometimes they call them if they haven’t shown up to see why. This will get some people who dropped out to decide to come! The organizers also move around in the background to time things like the food delivery above and to welcome stragglers, shuffle them into the room.

Cultures

I’ve done these events in several European countries, and, of course, America. If you’re not acculturated to different cultures, it’s good to go in with some sense-making tools. Apply these tools with care: they’re stereotypes, generalizations, etc. ¯\_(ツ)_/¯

Americans are pretty good at organically getting a conversations going. You have to be careful with them when it comes to individuals dominating the conversation, and the “readout” person above. American business culture is surprisingly hierarchical: HiPPO, and all that.

UK people and the Dutch have the relaxed, gregarious American stereotype, but much less HiPPO: they tend to speak as equals.

Despite stereotypes, most (other) continental Europeans are like this too: but (if you’re American) you have to get ready for continental European bluntness: where they tell you you’re wrong and that’s considered polite and helpful - I think of it as “free advice.”

Also, there can be language frictions. I only speak English, so there can be barriers with the French, Italians, Spanish, and Belgians. Germans are usually confident in their English (and, of course, the Dutch are bilingual, so English is no problem). But, in the world of IT, everyone speaks English very well, they just may feel like they don’t. In those cases, I try to make fun of myself for being a dumb-and-lazy American, linguistically, and that usually opens things up a little.

Motivating myself

Have I said, yet, that I don’t like talking in groups? This means that if I don’t catch myself, in a dinner like this I’m just maneuvering to run out the clock. That’s not commercially good! How do I motivate myself to do this thing that comes very unnaturally to me and also feels…not fun?

First, it’s my job. It’s amazing how “get over yourself” effective that is for me.

Second, I’m want to hear what have people to say, if it’s interesting. I was talking with Sasha Czarkowski yesterday, and I realized that one of the main reasons I don’t like group conversations is that I fear being stuck in a boring conversation.6 So, a lot of my tactics in dinners are about keeping things interesting to me. This risks going off commercial-topic, sure. But I have the job I do because I’m interesting in what my work does and what people do with our ideas and products. So, driving conversations to what I’m interested in is rarely off topic.

Presentations

I haven’t mentioned presentations because those are a bad idea for in-person dinners. Contrary to that, if you’re doing an online event, I think presentations are excellent, maybe even required. I wrote up more on that in my previous how to do executive dinners article.

I have the easy job

The other thing to keep in mind is that I just show up and talk. There is a lot more that goes into these events. You’ll need a professional field marketing person to lead and own the event: actually planning, arranging, running everything, and making sure it has tracked ROI. You’ll need people (probably an outside agency) to recruit people and call them, even day of, to remind them to show-up. Most importantly, you’ll need someone who makes sure all the post-event activities happen. These are not your sales people, it’s that field marketing person.

Anyhow. There you go: now go do some executive dinners :)

Also, here’s an older write up (from 2022) of some more of my tactics and general strategies for these kinds of event. It covers much of the above, but has a lot more on my experience doing them online (during COVID), and more detail managing the event (pre- and post-), which is the hard part.

Logoff

That was long! I’ll save the strange finds and links for next time.

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