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How to Run an Executive Retreat

Executive retreats are one of the most powerful avenues for clarity of purpose, solving major problems, and making important decisions.

Chase Damiano
10 min read
How to Run an Executive Retreat

Today’s zeitgeist tends to portray executive retreats as campy team-building weekends filled with trust falls, Two Truths and a Lie, and egg-and-spoon races. So, understandably, many executives don’t give them much thought.

But when you enter a retreat ready to make a difference with thorough plans for the outcomes you want to achieve, they can provide a vital reset for leadership teams and entire companies. Executive retreats are one of the most powerful avenues for achieving clarity of purpose, solving major problems, and making important decisions.

Bill Gates is a great example of an innovator who allotted significant time every year to do deep thought work—while running Microsoft no less! He hid in a cabin to read books, articles, and research materials, to think, and to write. Although his retreats were done solo, his purpose was similar to the executive retreat: to solve challenges, make difficult decisions, and set his company up for success in the future without day-to-day distractions. The one major addition that the typical executive retreat offers is a greater level of connection between executives.

But if you’ve never done an executive retreat before, or you need some fuel to feel good about deciding to do one, this article lays out some of the information that will help, including three top uses for retreats and nine things to be sure to do when you have one.

What to use executive retreats for

Focusing on difficult decisions/challenges

Early in my career, the company at which I was an executive had a huge decision on its hands: to acquire or not to acquire another company. Since this decision would change the trajectory of the entire business, we processed it in an executive retreat. These were the big questions we posed:

  • What does a successful acquisition look like?
  • What are the flags that will signify that this venture is failing?
  • Is the valuation at the right price?
  • What’s our 90-day post-acquisition plan that will set us up for a high probability of success?

Through lots of collaboration and debate, we found our answers.

Setting up for the future

Executive retreats aren’t just great for present-day problems and short-term planning for quarters one and two. They can also help executives reach clarity at the end of each year and guide them to plan for the company’s future. Here are four aspects of your business you can create clarity around during this time:

  • Vision: What does our company look like, in detail, 3-5 years from now?
  • Goals: What are the right focus areas for this year that propel us toward the Vision?
  • Roles: Are the right people in the right roles? Do we need more clarity around responsibilities and decision-making autonomy within the executive team (or others)?
  • KPIs: What are the 5-7 most influential metrics that define success and/or prove the health of our business?

These conversations can be lengthy and heavy. Again, they aren’t going to happen in your one-hour executive team check-ins. They require time and space.

Building connections

Companies often try to over-solve for a lack of connection in their workplaces by simply having occasional drinking events like open bars. It’s true—when people get drunk, they do open up and let their guards down. But this isn’t necessarily conducive to creating an amazing workplace culture post-retreat.

But you can have people share their beliefs, hobbies, and practices at a retreat. You can plan time for a member of the team to lead an event, like a restorative yoga class, a hike, a pottery class, or anything else that they’re passionate about. Anything that shows a fuller picture of who they actually are as people—not just the “workplace version” of themselves.

It can be hard for us to bring our full, authentic selves into the workplace for a variety of reasons—psychological safety being at the forefront—but executive retreats offer a unique opportunity to break this rigid mold. A well-structured and facilitated retreat can create a space for people to open up, be more vulnerable, share their personal lives, and forge stronger bonds with one another.

Logistics

How do you ensure that your executive retreat isn’t a waste of time and capital? Preparation.

Here’s a nine-point plan that can help you reach your expectations:

1. Set the outcome.

Be intentional and aim for powerful, tangible outcomes. Create a document with the written vision that’s been decided on and agreed upon by everyone.

“What’s the goal? What do we want out of this? How will we know that we’ve accomplished it?”

A poorly constructed goal is: “We’re going to discuss vision or discuss the long-term.” or “I just want to team build and bring people together.”

A well-constructed goal is: “The intent of the retreat is to ‘clear the air’ within the executive team accumulating over the past few months, to make a decision on spending $X to acquire ABC Company, to define success criteria for the acquisition, and to prioritize and delegate the top strategic goals over the next 6 months. After the retreat, we’ll hold an all-hands company meeting to share our decisions.”

2. Carve out the time.

How many days are you going to commit to the retreat? I’ve experienced and facilitated one-, two-, and three-day retreats, and I believe four- and five-day retreats can be increasingly valuable. Generally speaking, if the retreat is well-structured and planned, it will be successful, and if you can carve out more time, you can get more done.

People may not see the value of spending this much time away from their day-to-day work, but it’s up to the planners to articulate why everyone should buy into the program. Often, the value is this: You save tremendous amounts of time by engaging in focused, intentional conversation and debate, alleviating the cognitive burden of unmade decisions or plans. Instead of continuing to talk about a big, open-ended problem, why not commit to action and move it forward?

“We really want to reach this outcome. This is valuable. Here’s why…”

3. Create the agenda.

Once you’ve decided on the time frame, you need to plan out the entire retreat. Otherwise, you’re beginning at a disadvantage.

Start by dividing the goals for each of the retreat days and prioritizing the most important and challenging decisions first. If you crave more detail in your structure, you can block time by the hour with each hour representing a specific step toward your ultimate outcome.

Planning the retreat in advance also allows attendees to focus less on logistics and more on the problems at hand. Participants will be more capable of contributing to the bigger picture when micro-decisions have been taken off their plates in advance.

4. Prepare attendees in advance.

Having people come prepared is key. If you’re facilitating around annual goals, for example, you might send a survey asking, “What do you think should be the goals for the company? If you were the CEO, what would your top priorities be?”

When everyone comes prepared, everyone has the opportunity to offer thoughtful insights. It helps structure the conversation from the start. It’s like the preseason of any sport: With data collected before the real start, there’s less wasted time on experimentation when games need to be won.

You don’t want to get caught having people creating an analysis, doing research, and looking things up during active communication sessions. Everyone should be fully engaged—trying to reach the same outcomes.

5. Facilitate the conversation.

  1. Use an in-house facilitator. Have an executive on your team with ample retreat experience bring their own playbook and act as the lead facilitator.
  2. Hire an outside facilitator with a number of years of experience both inside a company and as a third-party facilitator or coach.

Either should be able to work with you and your team to translate your ultimate outcome into a structured agenda that delivers that result.

One extra benefit of the outside facilitator is that they can focus solely on their job—facilitating the retreat. On the flip side, an in-house facilitator has a lot of responsibility on their hands—both facilitating the conversation and actively participating in it. Balancing both can lead to an erosion of the quality of their participation (failure to contribute creative ideas and perspective) or erosion of the quality of their facilitation (failure to get the ultimate outcome).

6. Interlace positivity and gratitude.

Conflict, debate, and disagreements should be expected in this environment. Part of the facilitator’s job is to keep conversations productive and ease over tensions that may arise.

I’ve found beginning retreats with expressions of gratitude bears good fruit. As executives, we don’t always allow ourselves to show this type of vulnerability and appreciation for our teammates, so it can be powerful to go around the room and have each person answer questions like, “Why are you grateful that so-and-so is here? What has this person contributed to the organization that you’re grateful for?”

I experienced this multiple times in my career. In one particular retreat with my former company, the team had been experiencing tons of infighting—blaming each other and disagreeing on goals. To cut away the tension, we began by expressing gratitude. The groups were hesitant at first, but with some encouragement, soon the flood gates opened with huge statements of respect, appreciation, and love. Some folks even shed tears, having never experienced so much gratitude in the workplace before. This set us up for a powerful session to collaborate on translating vision to action.

7. Keep on track and take strategic breaks.

What happens on Day 1 can impact the pace and decisions of the rest of the retreat. It’s the facilitator’s job to keep everything on pace. There’s only a finite number of hours available, so conversations must be steered in the right direction.

Structure retreats with more breaks! Personally, this is something I’ve had to actively work on. Pushing forward isn’t always the answer. People have different learning styles. Everyone processes things differently. Structured breaks—short or long—can lead to greater productivity. They help people regroup and refocus their attention, and in the long run, they help us stay on track.

8. Clarify everything.

Chunk decisions down with action steps. Make “We” statements and personal statements like, “NAME decided to move forward with X.”

Sometimes, with more clarity, homework may arise in between retreat days. If the group discovers vital information is missing, someone might be tasked to do research so the group can move forward the next day without missing a beat. I’m not one to promote after-hours work typically, but with the intent of reaching these outcomes in such a limited timeframe, sometimes it’s necessary.

Make action items more tangible by tracking them with project management/workflow management tools. This ensures that each item has an owner. Really, this is “Action Items 101.” Everyone needs to know their precise next step and how it’ll be tracked. And everyone needs to know when they’ll need to articulate their progress. It holds people accountable to the greater mission of the group.

Sometimes after the retreat, when we get back to work on Monday, all of a sudden we have all these emails and meetings that belong to the pre-retreat paradigm that we just changed. Our positive mental energy about the future state of the company can easily erode if we shift back to the pre-retreat mental model. So by clarifying our decisions, action steps, accountability processes, ownership, and meeting times, we’re essentially translating what was discussed into action and blocking any fall-back into the old mental model. We’re following up on and moving forward with our momentum. This step turns nice ideas into clear plans.

9. Communicate to the company.

This step often gets missed, and it shouldn’t. After a few days of invaluable discussion and experience, your direct reports will surely want details. Here’s how not to communicate with them:

“How was the retreat?” “It was fine.”

“What’d you talk about?” “Oh, you know, big-picture stuff.”

Share the rich insights you discussed with your team. This can be a source of energy that helps people understand the commitment of their leadership and get them excited about the journey ahead. The exciting energy from the retreat can easily translate down the company hierarchy if executive teams are willing to share it.

I practiced this at Commonwealth Joe. After running executive meetings, we’d have company all-hands meetings. We’d share the different decisions that were made, how we planned on executing, and what to expect down the line. We’d even reveal things we weren’t sure about and didn’t know. It’s okay not to know everything. It’s okay not to have the perfect step-by-step, month-by-month roadmap. Entrepreneurial companies don’t grow that way anyway.

Communicating to the company—getting everyone talking, giving feedback around what they’re hearing, and asking questions—can really help solidify plans and boost morale. And acting quickly on this point is important. You’ve got to keep the energy pumping. Don’t let the investment of time and resources fade.

Take your company to the next level

Founders can get so wrapped up in the day-to-day business that we forget there’s a whole mess of strategy, direction, and thought necessary for taking our companies into the future. We need to allow ourselves to do this work, and a sure-fire way to do it is by going on executive retreats.

Executive retreats can break communication barriers and open us up to our peers in a way that wouldn’t be possible in a normal business setting. When planned thoroughly and led by a high-quality facilitator, executive retreats allow leadership teams to reach previously unrealistic outcomes.

They aren’t easy, but they can make things a whole lot easier in the long run if we just allow ourselves to take the time to engage.

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