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Running Executive Offsites Without Losing Your Mind (Part 1)

By In Technology

Running an offsite is one of those things that sounds straightforward until you actually try to do it. Then you realize it’s more like attempting to teach a cat how to swim.. like, it’s possible, but the trial and error is going to leave you with scars and trauma for you and the cat. The truth is, I didn’t learn how to run these from some leadership book. In fact, there aren’t many practical resources out there on this topic. Zack Urlocker (famous to me from MySQL) has a great article on the subject, and the HBR book “How to Plan a Team Offsite That Actually Works” is pretty good, and I’ve read and can partly “Retreats That Work“. But compared to other tactical or strategic business topics, there is suprisingly little stuff out there on how to plan and run what I think is one of the most important processes in a functioning executive team. So most of what I know has been pieced together by experimenting, failing, adjusting, and occasionally stumbling onto something that worked.

Over the years, I’ve realized that the best offsites aren’t just about staring at spreadsheets in a new zip code. They need to hit a few big goals if they’re going to be worth all the planning headaches.

  1. First, they give us strategic focus. It’s the one time everyone can step out of the chaos of Slack notifications and email fires and actually think about the future of the company. No one is allowed to answer a support ticket from a kayak.
  2. Second, they create leadership alignment. If you’ve ever tried to get a group of executives pointing in the same direction, you know it’s a bit like herding caffeinated cats (second cat reference already). Offsites are where we stop doing the daily functional stuff and agree on what we’re actually chasing this quarter or even the year.
  3. And finally, they build team cohesion. This doesn’t mean trust falls or awkward icebreakers where you have to say your “spirit animal.” It means real connection. Cooking dinner together, laughing at terrible pickleball form, or having spouses bond over yoga and day drinking. That’s the glue that makes the work stick.

Strategy and alignment and synergy and other business words are important. But if you don’t also have a little fun, then honestly, what’s the point?

Who Gets Invited?

One of the first questions people ask me is who actually gets to come. The answer is simple: just the people who report directly to me. That means my VPs and my C-levels. Keeping the group small matters. Too many people and it stops being a strategy session and starts to feel like you’re at an HOA meeting with whiskey. That’s actually the only way I would attend an HOA meeting, but that’s besides the point.

The Rhythm of Our Offsites

Over time, we’ve settled into a pattern that works for us.

  • We hold one-day offsites each quarter, right at the beginning of the quarter, to reset and align.
  • At the beginning of Q4, we host a three-day offsite. This one is much more involved, both in planning and in structure.

That Q4 gathering has become the cornerstone of our leadership rhythm. It’s where we not only map out the next year but also strengthen the relationships that help us make better decisions together.

The Big Airbnb Weekend

An example AirBNB we’ll rent

The three-day offsite is a little different. Actually, a lot different. Instead of cramming into a conference room for eight hours, we rent a big Airbnb within driving distance. It has to have something that makes it feel special. Maybe it’s a weird swimming pool, a pickleball court, a river with kayaks, or a beach nearby. Basically, something that makes it feel less like a board meeting and more like an executive retreat with paddleboarding skills designed to test our key-person insurance. A lot of these places are pretty weird. Getting a place where 5 couples can comfortably stay in a single house means either super luxurious mansions, or strange homes that have winding corridors, mapping our the evolutionary path of the renovations that made it a desirable property for events like ours.

We also come prepared. That means swimsuits, a fully stocked bar, and a Nintendo Switch for late-night Mario Kart battles. For the record, those races have only ended in tears two or three times, which I consider an acceptable casualty rate.

Spouses and partners join us for the whole weekend, from Friday through Sunday. Friday night we cook a big meal together. Saturday night we all go out to dinner. In between, the partners, who jokingly call themselves “the tech wives” even though the group definitely includes men, do their own thing. They go to yoga, they day drink, they sometimes prepare lunch for us, and in return we make sure to take them out for dinners. They get a vacation, and we get the benefit of stronger connections across the group.

A Tech Wife Grilling

It might sound unusual to mix work and family life, but it has been incredibly useful. When the people at home know and trust the people at work, it changes the dynamic completely. It creates more openness, more support, and a lot more resilience when things inevitably get tough.

Timing Is Everything

When you schedule an offsite matters almost as much as where you hold it. For example, I’ve found the sweet spot for our first offsite of the year is the third week of January.

  • If you schedule it the first week of January, no one is really in the office yet. Everyone is still half in vacation mode.
  • If you push it to the last week of January, the new year’s energy has already started to fade.

So the third week is usually just right.

For our one-day offsites, I like Mondays. That’s already the day we hold our management meetings, which means I have two hours of my executives’ time on the calendar anyway. It’s easier to rearrange schedules if we’re already starting from that block.

The Q4 offsite follows a set pattern too. We begin Friday morning at 9 a.m. and wrap up Sunday afternoon. Since we usually rent the Airbnb through Monday, people often stick around a little longer. Sometimes kids show up and end up swimming in the pool or playing pickleball, which is honestly a pretty great way to close things out.

Wrapping Up Part 1

That’s the foundation: who comes, when we meet, and how we structure the year. These basics took a few years of trial and error to figure out, but once we found the rhythm, it became much easier to plan and run these without burning out.

In Part 2, I’ll share what actually happens inside the offsite, including how I structure agendas, the kinds of exercises we run, and why you should never try to build your offsite plan in a Word document.

There is now a Part 2!

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I help companies turn their technical ideas into reality.

CEO @Sourcetoad and @OnDeck

Founder of Thankscrate and Data and Sons

Author of Herding Cats and Coders

Fan of judo, squash, whiskey, aggressive inline, and temperamental British sports cars.

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The Million-Line MVP

In Technology

A founder told me last week that his chatbot understands him better than most people he works with, and he wasn’t joking.

He had been alone in his house for the better part of a year building an app on one of the popular AI coding platforms, and he wanted me to take a look. Almost a million lines of code, one developer (him), no engineering co-founder, no senior reviewer, no nobody. The app had an ERP module, a CRM module, a custom AI agent with a name and a voice, built in mini-games (yes, really), dozens of character personas, a few landing pages, and a small army of social media accounts in multiple languages. He had not yet had a paying user, or even a free one.

He was, by the way, very excited.

(I’ve changed some details, since the pattern is what I want to talk about and not the founder. I see something close to this on roughly one out of every three sales calls now.)

What used to slow you down was the point

Building software used to be annoying for mostly good reasons. You had to hire developers, or learn to code yourself, or convince a co-founder to come along for the ride. Then, you would grind out every line, which would come at a cost (time, money, conversations, arguments, etc.)… basically friction. And that friction was not a bug, but it was like this ting that you are forced you to deal with, before adding any feature, whether the feature actually needed to exist.

Startup advice has been more or less the same for twenty years, maybe more:

  • Build something small
  • Show it to real people
  • Find out what they actually want
  • Don’t build a million things at once.

The Lean Startup came out in 2011 and we have all been quoting it at each other ever since (poorly, mostly).

This is what we talk about when we discuss “startup discipline”. It’s really not very complicated, but it can be really hard. It used to be hard because building was hard, and now it’s hard for a completely different reason.

How does one person build almost a million lines of code in a few months?

The honest answer is they don’t, the AI does, and the AI has no opinion on whether any of the code should exist.

This is the part I want to sit with for a minute, because I think it’s the heart of the problem. Imagine you’re building a startup that lets local news anchors rent out their unused toupees by the hour (try not to overthink this). You sit down with one of the AI coding tools and you say “build me a marketplace where toupees can be listed by the hour,” and the AI builds it. Then you say “actually, add a loyalty rewards program,” and the AI builds that too. Then you say “and also, add a Pokemon-style mini-game where users battle each other’s toupees,” and the AI starts coding.

It doesn’t pause or ask why, and it doesn’t say “dude, I love your enthusiasm but I am genuinely worried we are losing the plot here,” it just builds the toupee-battle-feature.

This removes the single most useful thing about a good engineering team, which is that engineers PUSH BACK. A senior developer, or a seasoned product manger, asked to add a toupee-battle mini-game to a B2B rental marketplace would slowly take off their glasses, set them on the desk, and ask one of those long quiet questions that means “we are not doing this.” The AI this is a sycophantic drone that has the eagerness of an underfed puppy to please you, and it has no glasses to take off. It also has unlimited keystrokes and believes that every single idea you’ve ever come up with is absolutely genius. At least it tells me that everything I’ve ever written or thought about is pretty clever.

A few months ago I ran into the perfect name for this, which is Slurm Coding. I used to call it AI crack coding, because the dopamine loop is very real, and I have really needed another hit of that good AI crack just one more time before I went to bed on more than one occasion. But Slurm is both more insidious in its combination of addictiveness and corporate outreach.

The MVP don’t change

Here’s what hasn’t moved in twenty years of startup thinking:

  1. Build the smallest thing that solves one specific problem for one specific person.
  2. Show it to that person (a real person, probably not your spouse, definitely not your mom, and DEFINITELY not my mom, and 100% not your chatbot).
  3. Find out what they actually do with it (which is probably not what you thought).
  4. Kill features, pivot, or double down based on what you learned.
  5. Repeat.

What’s new is that step one is basically free, and while not perfect, free is very alluring. You can build the smallest thing in an afternoon, or the largest thing if there’s no one around to tell you not to. Steps two through five still require getting out of your house, talking to humans, accepting that most of your assumptions are wrong, and throwing real work away. None of that is faster than it was in 2005, none of it is fun, and none of it scratches the “I NEED MORE SLURM” build-a-thing itch the way an AI tool does.

So a certain kind of founder just skips it, staying in the build phase indefinitely, because the build phase now feels like winning at a casino while getting unlimited free martinis. The feature ship (how to get them onto a server is someone else’s problem) the codebase grows, the agent agrees with everything. Meanwhile the only thing that actually matters, which is whether anyone wants this, goes unanswered.

It’s the founder version of Wilson the volleyball. In your unwashed isolation, you’ve made a friend, you’ve named the friend, and the friend agrees with everything you say. The problem is that the friend is also the boat, the island, and the ocean, and you haven’t actually left the house yet.

To be fair, I am not above this myself, by the way. I have, in my time, built things that nobody asked for and gotten weirdly emotional about them, but the difference is that mine were three hundred lines of code over a weekend, not almost a million lines of code over the better part of a year, which is sort of the whole point. No one asked for my William S. Burroughs poetry writing twitter bot, but I loved it anyway.

Codebases don’t love you back

Code you wrote yourself CAN hard to let go of, and code you wrote with an AI, when you are not a trad-coder, seems to be way harder. Experienced engineers seem to be more than happy to throw away AI code or rebuild it in a heartbeat. But I can see how even if you didn’t actually write the lines, but the shape of the thing is yours (you named the characters, you picked the voice, you spent months in a chair with this thing as your only collaborator), and you have feelings about it.

But one day, if you’re lucky, and it does have SOME product market fit, a real engineering team is going to need to look at your masterpiece. And they are not going to share those feelings. They’re going to tell you, as gently as they can manage, that most of it has to go. Not because they’re mean (they might actually be mean), but because almost a million lines of AI-generated code, written by one person, in one tool, with no architectural review, is never maintainable, almost guaranteed to not be secure, and almost never going to scale past the “prototype” it currently is.

So what should you actually do?

I mean, I already told you… Build the smallest thing you can, then show it to ten strangers and actually listen to them. Throw away half of what you built and build a slightly different smallest thing, and repeat until one of those things is real. Keep your runway reserved for the moment you realize you were WAY off about something important, because, like, you will be, and that moment is what your runway is for.

Use AI tools, because they are legit amazing. But treat them like a coffee machine (fast, useful, no opinions of their own), not like a co-founder or worse, a slot machine. Co-founders are supposed to tell you no, slot machines whisper “just one more hit baby!”