How to Lead a Powerful Team Retreat: 8 Executive Coaches Weigh In

Most of us don’t have many opportunities to get away and connect with the people in our lives, especially when it comes to our coworkers. But as our team of executive coaches has seen firsthand, teams who get away from the office to work together at a retreat or off-site return more engaged, aligned and excited to achieve their shared vision.

We recently asked 8 of our executive coaches and CEO Mentors to share what makes for an effective team retreat. Here are their tips to help you and your team get away, slow down and discover how to work even better together.

Create an Energizing Environment

  • “Be in a room that’s well-lit, preferably with natural light.
  • Feed people an assortment of good, healthy food known for keeping energy levels as even throughout the day as possible.
  • Choose venues that are aesthetically pleasing and physically comfortable: good artwork, nice architecture, cozy chairs, areas that allow for quiet thinking and solitude.
  • Build thinking and processing time into the agenda.
  • Don’t overload the agenda; less is more. Allow the conversations to go deep.
  • Have at least one meal together that is a non-working meal.
  • Build time into the agenda for something fun – a game, a contest, an excursion, an activity.”

Executive Coach Laurel Emory, Ph.D

Establish a Clear Path to Your Win

“When I reflect on team retreats, there are always a few key ingredients: First, find a location away from the work environment to help people explore new ideas together.

Next, create an agenda that has a good balance between hard work and fun — this keeps the team engaged and helps teammates connect on different levels.

And once you have those two set, establish a clear path to a “win” for the time away so the team can stay focused on that mission during the retreat. With those ingredients in place, you have lots of possibilities for success!”

Executive Coach Michael Regan

Tackle the Most Difficult Tasks First

“List the important and high-payoff items you need to get done during the retreat and start on them during your first morning together. Teams usually get most of these items done the first day. Tackle the hard tasks sooner than later — don’t let them linger — and make sure you’re communicating the good and not-so-good things quickly.”

CEO Mentor Jerry Baker

 Give Your Team the Gift of Time

“A team retreat might not always seem to be the best investment of time or money, especially for busy, high performing executives, but if it’s done right, there will always be significant ROI.

The ‘where’ is really important. It’s worth making the investment to take the team away to somewhere special that has plenty of natural beauty, preferably where they have to stay overnight. And use the facility and environment fully; go for walks, go out on the water to play, ride horses, have some fun zip-lining or whatever the location has to offer.

There’s no substitute for simply spending time together to get to know each other as fellow human beings. Retreats should give team members plenty of time and space to just connect. This is the best way to build trust.

I’ve designed and facilitated dozens of such retreats, and the biggest lesson I’ve learned is ‘Less is More’. Don’t overcrowd the agenda or try to pack too much in. Give people the gift of time to build connection, process together and dig deeper for better quality decisions.

Recently, many of the leaders and teams I’ve worked with have expressed a need to improve their health and cohesiveness — how they operate as a team, versus what they work on. As a result of just spending 2-3 days together, I have seen tremendous deepening in the amount of trust team members have for one another, and the level to which they’re willing to be held accountable, and hold each other accountable, for their actions and behaviors. This can pay dividends in the months and years ahead.”

Executive Coach Jonathan Rogers

Take an Intermission

“I for one have never liked to use the word ‘retreat,’ in creating a working meeting. For many, the simple word equates with ‘Boondoggle’ or sponsored vacation! I like to think of team gatherings as ‘Intermissions’ — a place to openly discuss the reality of our team’s current condition and mid- and long-term targets. Intermission allows everyone to voice a way forward for the next portion of the mission.

In my experience, the best way to ensure success is to have a convenient, comfortable environment away from the workplace. Critical to the success is also an agreed-upon policy against outside communication, and the lure of email, text message and phone interruptions. An exercise I find valuable at the end of the meeting is an individual share from all attendees on an action to hold them accountable for until the next ‘intermission.’”

Executive Coach Ross Stonecipher

A Change of Place + A Change of Pace

“Mark Batterson’s quote of ‘A change of place + a change of pace = a change in perspective’ is so relevant for team retreats.

First, getting the team outside of their office to meet somewhere else allows for different conversations. The conditioned responses to think about the work at hand in the office changes once you get a team away. Also, it’s highly recommended that you get the team out overnight. Something happens over a meal, especially dinner, that allows the team to connect on a more human level. Communication lines open up much better with time and space to discuss key issues. And when your retreat is led by a coach or another skilled outside facilitator, it allows the whole team to get fully involved in the right sorts of conversations, which drive decisions more effectively.

The pace of an effective retreat should allow the team to not be rushed and to have the complete perspective of holistic opportunities and challenges that very few schedules allow. When a facilitator can architect the agenda, they can focus on the team’s desired end results first and then create the right processes, meeting flow and topics to achieve those desired end results. A good facilitator will mine for needed conversations around high-conflict dynamics, drive to agreement and ensure clarity around decisions so that ultimately the team will leave the retreat feeling aligned, clear and fired up about the next steps of their journey.”

Executive Coach Greg Harkavy

Ensure Alignment

“Effective retreats occur when you ‘retreat.’ Leave the crush of the day-to-day operating environment and find a different, inspiring or unusual setting that makes a statement about being ‘in retreat mode.’

Work to describe a desired end result before the retreat. Facilitators can be helpful because they allow all participants to be equal participants in thought and discussion. No one is burdened with leading sessions, coordinating agendas or watching the clock, so everyone is free to be a team member.

Build in time to have fun and get to know each other as people, not just coworkers. Review the decisions, directions and communication plans you’ve discussed and agreed upon before you adjourn for alignment.”

CEO Mentor Gerrit Cormany

End with a Shared Meal

  • “Having a schedule is important, but not every moment should be scheduled. Give people time to bond, some time to recover.
  • Have activities and topics build on each other, rather than skipping around.
  • Have people work in different groups from their normal teams
  • Pick a great location — peaceful, serene, conducive for contemplation. Make sure the room is conducive to great conversation by having as many windows as possible — no mirrors — and a place to be outside to see nature and breathe fresh air.
  • End with a communal meal at a large round table, so each and every person can toast (not roast!) each other, share stories and express gratitude.”

CEO Mentor Raymond Gleason


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