If you’re looking for an executive retreat about how to do the work better, there are plenty — I run one. But less than a year into taking over as Table XI’s CEO, that’s not what I needed help with (or at least not the only thing I needed help with). I wanted to learn how to be a better CEO from peers I admired. I wanted to understand how the stress was affecting them as leaders and as people. I needed answers. What does work-life balance really look like for the CEO of a growing company? And when, if ever, did people think about life after retirement?

So I led a group of nine executives into the depths of the Scottish Highlands.

It’s less … kidnappy … than it sounds. The idea was to take OpsConf, our conference where operational leaders at mid-sized tech companies swap ideas about how to run businesses, and strip out some of the structure. Usually we rely on facilitation techniques, sticky notes and whiteboards to discuss topics and pull innovative ideas and advice out of people. This time, I wanted to try replacing the typical executive retreat agenda with the act of hiking.

“All truly great thoughts are conceived by walking” —Friedrich Nietzsche

executive retreat group

In my theory, we’d trade the workshop for a Walkshop. The trails on our three-day trek would guide the conversation. When the path narrowed, people would pair off for one-on-one conversations. When the hiking got tough, everyone would focus on walking and stay quiet with their thoughts. When we reached a clearing, we could sit together for a group chat. The goal was to engage people physically, so they could open up mentally and emotionally. With that in mind, we charted a hiking path through the Highlands.

Planning an executive retreat without the usual activities

Finding a way to get 10 people from all over the U.S. and U.K. to one location, then moving to a different lodge each day on foot required some tricky logistics. Harder than that, though, was making sure that once they got to Scotland, they’d get something valuable out of our three days together.

four hikers in the pasture

The first step was picking the right group. We went in with the idea of “dedicated time with dedicated people.” We wanted folks who were at the top of their game, and who were willing to really go for it. They had to leave their technology behind and commit to a trip without any work distractions. We ended up with a hand-selected group of 10, including an Irish woman living in Florida, an Englishman living in Scotland, an improv expert and a person in the middle of a career transition.

We wanted to encourage authentic, natural conversation, but we also had to turn 10 strangers into friends in a relatively short period of time. To give just enough of a prompt, we skipped the usual executive retreat topics and picked a different focus for each day:

  1. Day One: Firsts
  2. Day Two: Change
  3. Day Three: Future

The topics gave us the direction we needed to have serious conversations: Where do you want to be in 2040? How does change affect you? What was your first big failure? That’s ultimately what gave us the thing we needed most from the trip — deep relationships with people facing similar problems who we can now rely on when things get tough.

What we got out of our executive leadership retreat in the Highlands

The value is mostly in these relationships we forged through a lot of hiking, some kayaking and a very singular hitchhiking event with a Scottish Highlander (which I will happily discuss over drinks). But it took a lot of reasons to keep us trudging through three days of hikes. Our unconventional executive retreat ideas were in pursuit of these goals:

Be present

We really meant that bit about leaving distractions at home. We needed people to be present for each other, and for themselves — hiking is risky enough that you really should be paying attention.

Executive Retreat Activities

To test the skill, at one point in the hike we challenged each person to sit down and build something using only materials within arms’ reach. We got some elaborate structures, and a much greater awareness of our surroundings. That mindfulness is the first thing we lose when we’re busy. Walkshop gives us a chance to build up those practices, so when we return to our regular lives, we can continue to be present for the things that matter.


Everyone on this trip has a million demands on their time. Their average days are spent zipping from task to task, mentally exhausted but physically awake. We wanted to flip that, exhaust the body and let the mind recuperate.

executive retreat direction

Hiking gave us a completely different scale for time. If we heard about an intriguing distillery an hour away, we’d just start walking, instead of thinking about all the other things we could do with that hour. The walk encouraged us to slow down and stop hopping immediately from one task to the next.

Disconnect to reconnect

Wandering far away from the WiFi forces you to genuinely disconnect. No more checklists, emails, social media or meetings. At Walkshop, you get to unplug in every sense of the word.

It’s only then that you can reconnect with what matters. You really get a better appreciation of nature when you’re not looking at it through a screen. You also have much more meaningful conversations with the people around you. The distraction-free environment allows you to reconnect with yourself — giving you time to consider your journey.


Without the constant daily distractions, you find a focus on the trail that you could never get in an office. A single thought or discussion can truly consume your attention. It’s much easier to arrive at solutions when you’re in a contemplative mood.

Stretch your creative limits

We’ve heard the studies: Stanford researchers finding a 60 percent increase in creative output while walking. University of Essex scientists finding that mood and wellbeing are boosted significantly with as little as five minutes of outdoor exercise. Walkshop gives you a chance to put those ideas into practice.

The change in scenery triggers a change in mindset. Being in an unfamiliar environment helps you to consider new ways to make work more meaningful. Your fellow hikers will also push your assumptions, so you can bring out your most creative thinking and apply it to your toughest problems.

Dedicated time with some very dedicated people

Perhaps the single best thing about Walkshop is the time it gives you with extremely talented people. When else can you get 72 uninterrupted hours with CEO-level talent? Each person on the trail has unique insights and accomplishments, and you get three days to ask them any questions you’d like. After the hike, those shared experiences will be the basis for relationships you can rely on long after you've put your boots away.

executive retreat benefits

Keeping things going beyond the business retreat

I learned so much about myself specifically and about life in general — but that’s another blog post. I know I need to nurture all that creativity and peace of mind until I can get on the next Walkshop. Some of that’s accomplished with easy changes. I’ve been setting aside a regular 30 minutes each day to practice mindfulness with the Calm app. I’m also taking more of my meetings while walking, inspired by Table XI’s Director of Operations Dan Hodos, who talked about the practice on our podcast on how to facilitate effective 1:1 meetings.

Other things are harder. I’ve joined my first board, with a nonprofit that helps to bring arts education to Chicago-area schools. I need to keep turning away from work to make time for other things that matter, like giving back or taking time with my family. It is hard to maintain the discipline and focus that I had on the trail. At least now, though, I have nine people I can call when I have questions about how best to do it.

Want access to more articles like this?  Subscribe now to stay up to date on the latest from Table XI