A few weeks ago, after a session we facilitated for a team whose people had worked together for ten or fifteen years, one of the leaders said something I haven’t stopped thinking about. “I came in here thinking that I had known all of you. What I realize is that I really don’t know you guys the way that I thought that I did.”
If a leader who has worked with a room that long can learn that much in two days, imagine what a brand-new CEO doesn’t know yet.
The succession season is here
Challenger, Gray & Christmas counted 186 U.S. CEO exits in August, up 55% from July, and Andy Challenger said it plainly: “CEO exits increased in August as companies assess leadership ahead of the final quarter of the year” (Challenger, September 24, 2026). Fortune’s weekly Power Moves column has tracked a run of Fortune 500 companies naming longtime insiders as their next chief executive, many of them effective January 1 (Fortune, October 23, 2026). In Houston, Expand Energy’s new CEO takes over on October 26 after an interim stretch that began in February (The Oklahoman, October 19, 2026).
Insider or outsider, a new CEO gets about one quarter before the leadership team decides what kind of leader they have. They decide in meetings, in hallway conversations and in how the first hard decision gets made.
The first offsite matters more than the first all-hands
The all-hands is where a new CEO tells the company who they are. The leadership offsite is where the team finds out. Here is how we would run the first 90 days.
Interview every leader one on one first. We interview every leader before we write a word of a retreat agenda. A new CEO should do the same: what is working, what isn’t, what are you afraid I’ll change, what are you hoping I’ll change? You’ll hear things in private that no one will say in a room of thirteen.
Begin with the end in mind. Brittany starts every retreat design with one question: “What does success look like?” Then we work backwards. A new CEO needs the team to agree on the destination, two or three priorities for the year, measured from X to Y by when.
Let the team choose the route. I tell leaders it’s like a climb. You set the destination. There are a couple of routes. If the team says take the ridge line, then when you’re up on the ridge line and it’s scary, you all chose that route together. People defend what they helped build.
Don’t facilitate your own offsite. A new CEO who runs the room can’t also listen to it. An outside facilitator lets you be a participant and watch how your team works.
Say it until you’re tired of saying it. John Kotter’s classic research on why transformations fail named it plainly: leaders undercommunicate the vision by a factor of ten. A new CEO who thinks the message landed at the all-hands is usually wrong.
Close to home works
A first offsite doesn’t need a flight. For a Dallas–Fort Worth team, a ranch or lake house within two hours keeps the focus on the people (see places near DFW). For teams elsewhere, our venue guide lists places near New York, Chicago, Boston, Nashville and more.
The new year is ten weeks away. If you’re stepping into the job on January 1, or you just hired the person who is, talk with the founders about the first offsite now, while there’s still time to interview every leader before it.
Frequently asked questions
What should a new CEO do in the first 90 days?
Meet every leader one on one, agree with the leadership team on two or three priorities for the year, and hold an early leadership offsite where the team chooses how to get there. Then communicate the plan far more often than feels necessary.
Should a new CEO hold a leadership retreat?
Yes. An early, facilitated offsite shows the team how decisions will get made, builds trust faster than a series of meetings and turns the CEO’s direction into a plan the team owns.
Why use an outside facilitator for a new CEO’s offsite?
A CEO running the room can’t also listen to it. An outside facilitator manages the agenda and the hard conversations, so the CEO can participate and learn how the team works.
Related service: Executive Leadership Retreats
