How to plan a great team offsite

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Should we all stay in one big house?

I could feel my heart pounding as I looked around the room at the people seated in the massive circle.

I took a sip of coffee and tried to relax in my chair. The relaxing was the hardest part because the voice in my head was telling me this was the most critical day of my tenure as CEO.

This team had to come together. We had to make sure nobody would quit.

Days earlier, we had laid off 40 people. In the face of a major shift in the venture capital climate, we decided to shift our strategy. We would focus on getting profitable and growing revenue without the benefit of a large sales team. That meant painful changes.

To help the remaining team pull together, mourn the loss of their teammates, and find a path forward, my coach suggested we take a couple of days for a company offsite.

We had done offsites before, but they had been dry, boring events held in nearby hotel conference rooms. This one needed to be different. It needed to be connecting, alive, and real. It needed to work.

So we took a different approach.

We headed to the mountains.

We invested two full days. We stayed together in one big house. We took time to talk about the changes we were going through as a team, to talk openly about how we were each experiencing those changes, and to explore together what we needed to move forward. We also took a hard look at the business. We zoomed out to look at the ten-year plan, the adjustments we made, and the necessary tweaks to the road ahead. We ripped through the financial model openly, shared recent board feedback, and answered every question the team held.

I am so glad we did.

That team pulled together, stuck together, and 5x'ed our revenue over the next two years without additional headcount.

Following that first epic offsite, offsites became a critical part of our practice at Twenty20. We designed quarterly offsites into our planning cadence, budget, and culture.

Since moving into coaching work myself in 2019 and scaling that work with Sanity Labs, we have taken the learnings we developed beginning with that critical offsite and helped dozens of other organizations benefit.

I believe that offsites done well are one of the most powerful tools in the CEO's quiver.

Most companies do not do them well.

Let's talk about how to get them right.

Your team will thank you.

Signs your company may be hungry for better offsites

When we begin working with new coaching clients, one thing we will often do in the early months is spend time with the company's leadership teams.

When we hear the following feedback, it is often a sign the team does not have a sufficient offsite practice:

• People are not clear on near-term or long-term goals
• There is a lack of buy-in across the team for the current strategy
• Employees are unclear about how decisions are made (including near-term goal setting, budgets, fundraising plans, etc.)
• The team does not seem to know and trust one another (this is particularly common with distributed teams)

When themes like these pop up, exploring how the CEO or leaders think about supporting the team's ability to connect, zoom out, pick their heads up, or think strategically is helpful. Offsites are often a critical component for doing so.

Why invest in offsites?

Offsites are a powerful tool for helping your team get to know one another.

We talk a lot about the importance of trust for high-performing teams, but we rarely talk about how to help teams develop high levels of trust.

Humans are wired to trust those we know, have spent time with, and live near. Particularly for distributed teams, but even for those who spend time together in the office regularly, establishing this kind of innate trust can be challenging.

Spending even a few days here and there living together somewhere outside the day-to-day can help tremendously.

Offsites also help your team pick up their heads and see the whole chessboard.

When I ask a CEO whether they want their team to see the big picture, they always immediately say 'yes'! When I ask how they help them to do that, the answers are often slow-coming.

Offsite can help.

They help you and your team get your heads out of the day-to-day slog of work...and life.

Time to pick your head up is crucial if you want your team to think strategically about long-term opportunities and needs.

Finally, offsites are a great time to consider the 'company' and the business:

• The business is comprised of the products or services you sell to customers.
• The company is comprised of the humans you have pulled together around a shared mission.

Most often, in the day-to-day, we tend to the business but negate caring for the company. We develop company debt alongside tech debt. Offsites are a great way to address company debt and set your team up for greater success in the future.

How to design a great offsite

Include the team

If you are going to invest in offsites, let's make them great!

Here's how.

First, include the team. As a founding CEO, I often found it tempting to put my headphones on and design shit myself. Do not fall into the same trap as me.

Invite the team in. Design the goals and the broad strokes of the offsite together. Then have individual people or teams take parts of the offsite to own. You might even use this post as a blueprint but feel free to edit/adjust it and make it your own!

Consider helpful facilitators

It is a tall ask of yourself or other leaders to be both a facilitator and a participant in an offsite.

Consider hiring someone to help with facilitating. We spend a lot of our time at Sanity Labs helping with the design and facilitation of offsites. There are a lot of other great folks out there as well.

Having a facilitator present can make it easier for you as leaders to relax into being present as participants and be free of the need to manage people's experiences, the clock, or the agenda.

If your stage or budget precludes hiring help, consider inviting another CEO or advisor to help out. Even if they only come in for a portion of the time, you may find the assistance helpful.

Location, location, location

One of the most critical mistakes I see teams make when planning offsites is their space selection.

Selecting a nearby, low-cost hotel conference room can be tempting to manage time or budget. Please do not do this!

We are creatures of our environment. Our minds, emotions, and nervous systems all respond to our surroundings. If you want your team to be creative, connected, and thinking big, do not stuff them in a small room with fluorescent lights.

You do not need to blow the bank. You do need to get creative.

I prefer a big house where everyone can meet or even stay together. (If staying together, make sure everyone has comfortable sleeping arrangements and that needs are met regarding comfort, safety, gender respect, etc.)

Aim for a space that feels different from the day-to-day.

The most critical element is a large, open meeting space where people can sit comfortably in a circle.

Walls are helpful so you can post things (including sticky notes! More to come on that below.) Whiteboards are not necessary.

Access to nature is a huge positive. People's minds and bodies light up near nature. You may also want to use any trails or open areas for partner walks or breaks (more below).

For similar reasons, you will want room to roam. This could take the form of nature trails or city sidewalks.

Divide time between the business and the company

As noted above, in our approach at Sanity, we explore the difference between the business and the company.

For offsite planning, we like to divide time between the business and the company.

For example, if we plan a two-day offsite, we might spend the first day focused on the business and the second day on the company.

The first day might include topics like:

• Review of 10-year and one-year vision
• Review of the last quarter's goals and results
• Deep dive on product and customer learnings
• Check-in on performance against the financial plan
• Recommendations on goals for the next quarter

While the second day might include topics like:

• How well are we working together as a team?
• What would help us work even better together in the quarter ahead?
• What practices or working norms are we finding most helpful? Which are feeling harmful or in the way?
• What might we start/stop/continue to help improve our recruiting in the next year?

The first day is focused on products, services, financials, and the like. The second day is focused on the humans. Looking back, most leaders find they over-invested in their business and under-invested in their company. The company is typically where long-term competitive advantages lie.

Set clear goals

Before designing an offsite, get clear on the goals of the time.

When we meet with leaders to help with offsite design, they often have a strong sense the team needs a reset but have not yet written down their goals for the time.

Pull together whoever is involved with the offsite preparation, take the time, and write down a few clear goals for the time.

It may be helpful to ask:

• What do we want to leave the time with?
• What do we want to be different on our first day back from the day we leave?
• What do we want to achieve while we are together?
• How do we want to feel coming back from the offsite?
• If we could only achieve one thing, what would it be?

Consider the appropriate size (all-company vs. team)

In light of the goals you hold for the offsite, be thoughtful and selective about who should attend.

It may be helpful to have offsite throughout the year for:

• Board members
• Founders (especially in the early years)
• The leadership team
• Sub-teams within the organization (especially as the organization scales)
• The whole company

If this sounds like a lot of time outside the office, consider two things:

1. Not everyone is attending every offsite
2. This is not time away from work. This is the most valuable work.

It may also be helpful to think of each group as a team. For example, what would you do if you think of your board as a team where you want to build high-trust and high-function? One thing you might do is ensure those folks get to know one another.

There's no one-size-fits-all here; break down the approach as you see fit.

Mix up the mediums.

Now that you are clear on where you are going, with whom, and what you are trying to achieve, it is time to design how you will spend the time.

If you have already divided the time into company and business, you might further divide the time around your goals.

As you do so, mix up the space and the mediums.

If your first session is inside, brainstorming verbally, sitting in a circle, do the next one journaling outside, followed by partner walks to share what came up.

Changing locations helps keep the energy up and increases creativity.

People process information better while moving from side to side, so mixing in times of walking to help with digesting ideas is helpful.

People also have different styles of learning and sharing. Some prefer reading information, while others prefer hearing it audibly or diving in and working with it. Design accordingly to ensure you engage the full team.

I will share a variety of mediums below that you might pull from.

Design time for the team's needs

This may sound obvious, but many people miss it in their offsite design.

Build-in time for the team's needs. These should include:

• Food, water, bathroom
• Home needs: people have kids, aging parents, and more. Having time to check in will help them relax and engage for the rest of the day.
• Work needs: your team members may have varying abilities to be fully offline for an offsite day. Let them know when there will be times to check email and the like; check-in to ensure that works for the people present.
• Breaks to move, stretch, process.

Identify and divide helpful pre-work

As your design comes into high fidelity, explore what kinds of pre-work might be helpful.

This might include things like:

• Summaries of work completed and learnings unlocked
• Supporting data
• Updated financial forecasts
• Identification of key-questions
• Updated hiring plans

...or anything else that would set you up with everything you need to achieve the goals you noted above.

You might divide the pre-work so that multiple people are involved and carrying the load. I prefer to pull together all the pre-work into a packet and print one packet for each person present at the offsite.

You might then set time on the front end for everyone present to read through the pre-work materials before heading into the meat of the offsite. That way, everyone starts on the same page with the same information.

It may feel tempting to ask everyone to read before the offsite, but this approach tends to break down. You will feel like you are saving time, but someone will fail to do the reading, they won't want to admit it, and you'll pay the price in weaker collaboration.

Give people time in the room to read and review the data. This also allows for any questions to be answered right after reading while they are fresh.

Helpful mediums for offsite

You may have read above my recommendation on 'mixing up the mediums' and thought: 'What are mediums?' or 'What are my options?' Let's explore a few mediums or tools we use as coaches in offsite facilitation.

You do not need to use all of them for every offsite. Pick and choose and play with those that sound interesting to you.

Let yourself and your team design the offsite that feels right for you!

Here are some tools we love. Try them and edit them as you like. There are many more out there, and you can also invent your own!

Guided journaling

Guided journaling is a wonderful place to start when you have a group of people together in the room, and you want to get some of what's in their heads and hearts out into the conversation.

Guided journaling means:

• Giving people journals and pens (or something to write on and with)
• Providing a series of prompts
• Giving them time to write about each

Once each person has completed the writing, you can invite sharing in any way you like (open popcorn-style discussion, partner walks, or small group huddles, to name a few, as discussed below).

Guided journaling yields deeper, more interesting results than simply opening up conversations for group discussion. This is because:

1. People get to go deeper into their own thoughts before shifting into listening mode
2. Everyone gets a chance to form their thoughts, not only those inclined to share first or those with the most power, privilege, etc.
3. Folks who prefer to process in writing have time to do so. Folks who prefer to process out loud can still do so when sharing, but journaling first puts everyone on equal footing.
4. Everyone is left with a record of their thoughts to which they can refer back.

Open discussion or "brainstorming."

This is the old standby. People sit in a circle. A question is presented. People share.

There are a variety of ways to do this:

1. Popcorn-style. Anyone who wants to shares when they feel inclined to do so. This is nice when you want to allow those feeling inspired to go first or where you sense that allowing more reserved folks to sit back may be helpful. The downside is you often hear from the same people.
2. Around-the-circle. One person at a time shares in order around the circle. This way ensures everyone gets time to share. It helps you, as a facilitator, ensure everyone's voice is heard. If you time-box or provide instructions on the length of sharing, it also ensures everyone's voice is given equal stage time.
3. Inner and outer circle. In this format, a smaller group sits in the middle and brainstorms or shares. A larger circle of people surrounds the small group, listens, and takes notes. Afterward, each circle takes turns sharing what came up. This can be a powerful way to 'observe' or 'coach from the sidelines or to see the whole chessboard at hand easily.

Partner walks

Each person pairs off with one other person. It can be fun to ask people to partner with someone they know least in the group (this is a great way to give people a chance to know one another better). Then:

• Give each pair a length of time (i.e., 20 minutes)
• Instruct each pair to walk away from the meeting place for half the time and then back (i.e., 10 minutes out and 10 minutes back).
• One partner speaks on the way out. The other partner listens. Then, at the halfway point, they swap roles.
• You might then ask everyone to share with the group. They might share what they heard from their partner, any commonalities that arose, or whatever other elements feel helpful to you as a facilitator.

Small group huddles

Invite the broader group to break up into smaller groups. They might share responses to a prompt or journal entries or do some assigned shared work. Give them clear guidelines and time to return to the larger group. This is a great way to get people involved, have their voices heard, and work with people they may not interact with daily.

Affinity diagramming (i.e., sticky-note brainstorming)

This is one of my personal favorites!

Affinity diagramming is a powerful collaborative technique used to categorize and analyze large sets of information by placing them into natural relationships or themes. It's particularly useful during brainstorming sessions, project planning, or problem-solving meetings to distill complex issues into manageable parts.

The technique allows you to physically group similar items so that you can focus on broader themes and patterns, making it easier to strategize and take action. This method is often employed with a team to create a collective understanding of a complex situation, though it can also be used individually.

Steps for Affinity Diagramming:

1. Gather Materials: You'll need sticky notes, pens, and a large wall or board on which to stick these notes.
2. Assemble Your Team: Gather the team who'll be working on this exercise. Ensure the team includes people from different perspectives related to the problem at hand.
3. List Ideas: Ask participants to write their ideas, observations, or feedback on sticky notes. One idea per note.
4. Random Layout: Place these sticky notes on the wall/board randomly. At this point, everyone should be able to see all the notes clearly.
5. Categorize: Ask participants to silently arrange the sticky notes into related groups or clusters. No talking is allowed during this process to ensure that categorization is based on intuitive 'gut-feel.'
6. Discuss & Refine: Once all the notes are grouped, facilitate a discussion about why certain notes were grouped together. Feel free to move notes around if the team agrees they belong in different groups.
7. Label Themes: Create header cards or use a different colored sticky note to label each group. These labels should encapsulate the theme or idea that binds each group of notes.
8. Prioritize: Depending on the purpose of your session, you may decide to prioritize groups or individual notes based on importance, urgency, or relevance.
9. Action Plan: Identify next steps, delegate tasks, or make decisions based on the now-organized information.
10. Document: Take photos or transcribe the affinity diagram into a digital format for future reference and for those who couldn’t attend the session.

Affinity diagramming is a simple yet powerful tool that allows teams to organize their collective knowledge and insights, turning chaos into actionable clarity.

A note on note-taking and takeaways

Speaking of takeaways, this piece of outside planning is so valuable yet commonly overlooked; thus, I will give it its own section.

It is helpful to have a designated note-taker in every section of your offsite. In addition to writing down any takeaways from the work, this person should memorialize any generated ideas, agreements, or other work product and ensure it makes its way back to the office.

I have attended too many offsites where valuable work was done, but it was left to wither in everyone's memories rather than captured and protected.

If you are going to spend the time to hold an offsite, which I am obviously in favor of, make the most of your investment but capture and organize the work done.

Entering the space and creating agreements

Now that you have a well-planned offsite and are equipped with a menu of tools to make the most of your time lets talk about how you can help your team or whoever is present enter the space and show up ready to do great work.

When discussing ceremonies, we often think of indigenous cultures or formal affairs like weddings and funerals. But designing some ceremony into any human interaction can help set up the environment necessary for a shared experience.

In the case of a team offsite, here are a few elements that may help create the space:

Do something to mark the beginning and end of the time.

This might be as simple as ringing a bell or a gong, doing a funny team dance or chant, or anything else you can think of.

Marking the beginning and end of a shared time helps create a sense of container and an awareness in our psyches that this is a different time. This is not office time; this is not daily life; this is something different entirely.

Make conscious commitments

As you enter the space, invite the team to make conscious commitments about the time. This can include anything the team wants or needs to make the time effective.

Samples include:

• Any confidential portions
• An agreement to hold outcomes loosely
• A commitment that we will leave with clear next steps
• Promising to hit the pause button if any topics become too heated or personal

...or anything else you and your team might need.

Holding expectations loosely

Speaking of holding outcomes loosely, I would suggest making this an explicit part of any team offsite.

This is not to say you must drag out decisions or avoid committing to goals. But setting an ambitious agenda for an offsite and then insisting that everything gets done is a recipe for mediocre, uncreative work and soft commitments to outcomes.

We are looking for spaciousness, creativity, and out-of-the-box thinking. These expressions are more about hunting a wild animal than playing whack-a-mole. You need to be patient, quiet, and wait for them to approach you. Rushing is a recipe for missing the good stuff.

Common mistakes in offsite planning and facilitation

Having attended or facilitated dozens of offsites over the years, here are some of the most common mistakes I have committed or witnessed.

Focusing only on business goals

You are building a company, not just a business. If you will get your people together, talk about the people stuff too. The people are what make the business possible.

Trying to do too much

If you are wondering if you have too many goals or sections planned for your offsite, you probably do!

Put the important stuff up front. Be ready to adjust or cut as needed.

Things going 'off track' often means you are getting to the good stuff. Make time for it.

Efforts at connecting are lame or fratty

Mostly humans connect over shared new experiences and open conversations.

Over-engineering 'team bonding' or requiring everyone to get plastered at a dive bar to fit in with the team can be unhelpful roads to head down.

Not stepping out of the day to day

If you remove only one thought from this article, let it be that your people need an invitation out of the day-to-day.

Change the location, get close to nature, and turn off the laptops.

If you want your team to see the whole chessboard, pick their heads up, and think strategically like owners, you must treat them accordingly.

Facilitating it all yourself

If I could go back and do one thing differently in my earliest offsites as CEO, I would bring in someone else to run them.

It is hard to be a facilitator and a participant. And there is an art to creating the environment and structure needed to help a team flourish in their exploration.

It does not have to be a professional coach (although we are here if helpful!); especially in the early days, it might be an experienced founder friend or advisor.

Going cheap (time or money) on location

You do not have to spend a fortune on a fancy house in Tahoe. You can go cheap in the desert. But if you cut your team short on time or try to make a dingy Holiday Inn conference room a place of deep collaboration, you are setting yourself up for failure.

Take the time.

Find open space where you are comfortable.

Find a place where you feel like your heart and mind can breathe. Those are good signs.

Closing thoughts

Facilitating the kind of container a group of humans needs to develop deeper connections or to do thoughtful, long-term strategic work is a craft.

It may take practice for you as a leader. It may also take your team practice to get into this mode together.

The more you do it, the better you will become.

Don't beat yourself up if your team's first offsite does not meet your expectations. Do a post-mortem, learn from what worked and what didn't, and keep improving. The skill of helping your team find space of this kind to connect and do big-picture work will pay dividends.

I appreciate that you are here. If you were forwarded this email and it resonates, you can subscribe here.

If I can be helpful along the way, please reach out!

In the meantime, wishing you riches in the desert.

-Matt

Looking for some support? If now is the time to consider coaching (or a CEO peer circle) reach out here.