How to Retreat

To retreat, in the tactical sense, is to strategically cede ground by withdrawing; to double back, in the face of overwhelm, in order to reassess. This isn’t fully how we use the term in organizational design and development, though I would argue that it’s apt, given how overwhelmed many of us feel in the day-to-day. Either way, the intent is to step back, look at the field from afar, and weigh options anew and gain perspective.

I’ll also add: our field of attention holds far too much these days, and so the other hallmarks of a retreat practice are depth, presence, and focus.

More than anything— money, new clients, sleep, a new hire— I think most business leaders just need space to gain perspective. Often I hear this expressed as I need more time, but I find usually what people mean is they need space away from doing, doing, doing to be able to reconsider some aspect of their life or business. A cessation of meetings and demands on their attention to attend to a different viewpoint.

A chunk of my November was spent traveling to facilitate team retreats, and so these precious spaces of withdrawal are on my mind. I want to offer some thoughts and suggestions on the two broad types of retreating in the context of small business and organization: leadership retreats and team retreats.

The Building Blocks of Retreating

This is a non-exhaustive lists of the types of distinct activity that might comprise a retreat:

Reflect + Celebrate
Wander + Dream
Brainstorm + Imagine
Gather + Bond
Surface Patterns + Sort
Analyze + Unblock
Architect + Design
Deliberate + Decide
Plan + Commit
Play + Chill

When I plan retreats I often imagine an energetic shape for the day. A spiral or funnel is a common energy pattern, starting the day zoomed out on big picture things like values and strategy, then zooming towards the tactical as the day moves along. Retreats can pulse too, moving back and forth between imagining possibilities and planning tactics. Sometimes they might even go sideways, if a particular long-simmering conflict emerges during the course of the day.(A good reminder to allow flexibility for emergent issues).

One way to structure a retreat is around timespans: decide the longest timeframe you need to address (Five years? One year?) and design from there, planning blocks of activity accordingly. Different types of activity lend themselves naturally to different timespans:
Reflection and Celebration are usually about the recent past.
Wander and Dream invite longer time, perhaps even a decade or more.
Plan and Commit best fit the next few weeks or months ahead.

A note on balancing planning and emergence: Experience has taught me that I will always attempt to stuff too much into an agenda. This isn’t always a bad thing! Asking a team to rise to the occasion of an ambitious agenda can be invigorating for all, as long as there’s flexibility to adjust if the group needs to slow down or tackle fewer things.

Another trick is to craft an agenda that leaves me nervous about having too little to fill the time. The worst that can happen (I’m speculating, we always fill the time) is that folks get some extra space to shoot the shit.

Taking the long view: Leadership Retreats

These might be solo if you’re the only owner¹, or with your business partner or key leaders.

Rhythm-wise, I have a few clients who take themselves off quarterly, usually away from home for a day or two to spend time in contemplation and strategy. For others a yearly cadence makes more sense. A regular practice of white space to work on your business takes the pressure off a retreat, and can also support a clearer sense of how often and what to retreat about.

It’s certainly possible to retreat at home, but strange contexts support perspective shifts that are impossible to provoke amidst the proverbial laundry and dishes. Familiar spaces have too much of our stuff in them.

That said, you don’t need a secluded mountain top or a lot of planning. When I lived in Philly, I occasionally used the Hotel Tonight app for a day-of hotel room for deep work, and once supported a client in devising a scheme to take a train from Philadelphia to Pittsburgh and back to work on some big picture business stuff.

The content will vary on the season and need of the owner and business. Sometimes it will be obvious that you just need two days to fully dig into re-imagining a new operating system or a product line. Other times call for meandering long walks.

Coming together: Team Retreats

There are so many reasons to hold team retreats!

• Because you’re a remote team and want to build connection in person.

• To have complex or demanding conversations: every organization has a reserve of conversations that are not being had because they’re too hard, require too much time, or because the people involved need outside facilitation to have them.

• To brainstorm new ideas and create connections that can only arise out of a specific group of people coming together outside of their normal context.

• To Reset (I love a retreat for shaking up routine meetings that need to chucked or redesigned.)

• To onboard people to new ideas and ways of working and to create buy in around change.

• To bring more people into longer timespans: while leadership may be comfortable thinking bigger picture, not all teammates get the opportunity to think beyond their immediate production.

It’s not necessary to have outside facilitation, though there are certain corners of your business or culture that will never get touched without someone outside to shine a light on them; we’re too close to our own work to see everything.

The real gift of outside facilitation has to do with allowing a team to step outside of habitual power dynamics and norms. A business owner that always plans and leads their own retreats is never an equal participant, having someone come in with (temporarily) more power tips dynamics and opens up possibility.

Sometimes the best way to shift perspectives is to bring in an entirely new one. And sometimes you just need to pay someone to say out loud the thing that everyone already knows to be true.

Returning from Retreat

On the other side, it’s easy enough to slip right back into waiting pile of dirty dishes.

• The one nonnegotiable part of any retreat agenda should be the one where you identify and commit to what’s next, which is often going to be accountability structures and rhythms.

• Aim to have a clear answer for who and when for any what.

• Assume that you won’t have it all figured out, there will be percolations after, and that you need some dedicated space to circle back on whatever you didn’t resolve. Put it on the calendar.

• Commit or recommit to regular protected time to revisit the nebulous and exciting visions you concocted. I mentioned white space above: time for leaders (or anyone) to spend on the business, outside of daily demands.

• Be explicit about protecting any decisions made during retreat time from being immediately eroded by operational pressures. If you figured out you need to overhaul a client onboarding process, you probably need a half day blocked off to tackle it. Yep, calendar that too.

Retreats in other places:

Social media publishing company Buffer’s peek inside their process of planning annual retreats for their internationally distributed team.