5 Questions to Optimize Your Next Offsite

I just wrapped up another Breakthrough Offsite for a client, helping their leadership team frame their 2022 plan and prepare for delivering that plan to their upcoming company and sales kickoff meetings.

I love seeing teams come back together in person – many for the first time in nearly two years – and I am honored to be a resource to help them make the most of the significant time and cost investment of strategic planning sessions.

If you’ve been tagged to take a crack at developing the agenda for your next offsite – and you’re looking for an idea on how to get started – I’d love to help by sharing five key questions I use when a client asks me to jump into their offsite planning.

In advance of the offsite, I meet 1:1 with each participant to build rapport, look for areas of alignment, and surface challenging areas that could derail the team’s work. Here are the five core questions I use during those discussions:

1. What are the three most important questions we have to answer while we’re together?

2. What will be the most challenging questions to answer (or topics to discuss)?

3. What were three meaningful moments for the business over the last year?

4. What activities or exercises can create greater team cohesion?

5. Is there anything you’re concerned about that you’d like to flag?

I close these discovery conversations by asking how else I can be helpful to the process, then I summarize the feedback in a discussion guide that’s used to frame the agenda and the big questions to answer.

I hope these questions are helpful for you, too. If you’re looking for additional support, please let me know. I love working with leadership teams to design and deliver tailored programs that spark creativity, sharpen focus, and leave everyone aligned (and excited) for what’s next. If you’re looking to inject that into your next offsite, reach out and we’ll set up a time to jam.

PS: Have you seen my just-released Six Practices for High Performance? I’m grateful for the incredible feedback I’ve received, including this gem, “My day is better because I prioritized ten minutes this morning to watch your Six Practices.” Unlock your free copy today!