How to Develop a Great Strategic Leadership Offsite Agenda

Posted 02.20.2024

Over the course of this year, I’m going to develop the agendas and facilitate around a dozen strategic offsites for C-Suite executives and their senior leadership teams. Most of these will be day-long offsites for client company leadership teams to help them make sure they step back from the day-to-day swirl three times a year to set a course, assess their progress, and ensure that their time and attention are focused on the things that matter most. For three of my client companies, this is the third consecutive year that they’ve asked me to do this kind of work with them. 

With all that experience, I’ve learned a lot about how to develop and write an agenda that gets a leadership team engaged to create meaningful insights and outcomes. In this post, I’m sharing what I’ve learned about how to develop an agenda that yields results. What follows is a mix of lessons on process and content.

Make it Relevant – The quickest way to lose the room is to work from an agenda that misses the mark. To ensure that the agenda is relevant, do the homework. About a month before each offsite, I conduct 20-to-30-minute structured interviews with each participant to learn what everyone thinks are the most important challenges and opportunities facing the team. From there, I do a pattern analysis to come up with a draft agenda that addresses the most relevant and frequently mentioned topics.

Review the Draft – When the draft is ready, I review it with the principal C-Suite officer and finalize the agenda based on their input.

Send It Early – Once the agenda is final, I send it to the participants 7 to 10 days before the offsite. This timeline gives them plenty of time to prepare for the meeting.

The agendas usually include the following elements and considerations:

  • Define the Objectives – At the top of page one, offer 3 to 5 clear and succinct objectives for the offsite. They should clearly communicate to the team why the meeting is relevant and serve as a reference point and reality check before and during the meeting.
  • Open Soft –Begin with some sort of quick participatory conversation that provides a soft open for everyone to center themselves and connect with each other. The goal is to establish an atmosphere of safe vulnerability and a positive tone for the day.
  • Set the Table – Then move to a quick recap of how the group’s input informed the agenda. Ask the principal officer for their thoughts on goals for the day and then solicit early input from others. A good way to do this to play back some of the input they provided in the discovery interviews and give them space to elaborate on the trends in that input.
  • Leave Space – It’s important to leave space in the day for the group to think and dive deep. That means limiting the work to no more than 2 or 3 big topics for the day. It’s better to go deep on the things that matter most than wide on a long list of stuff to do.
  • Sequence the Work – The sequencing and flow of topics makes a big difference. Quite often, there’s work that needs to be done first to set the table for work scheduled later in the day.
  • Frame the Questions – For each segment of the meeting, come up with 2 to 5 questions for participants to consider and address during their work on that topic. Include the questions in the agenda so participants can think and prepare in advance.
  • Provide Digestible Pre-Work – Position participants to come to the meeting prepared by giving them digestible bites of pre-work to complete ahead of time. People are already too busy, so pre-work should be manageable and require no more than two hours in total to complete. Pre-work can be brief topical articles to read, a podcast episode to listen to, or a worksheet to review and think about ahead of time. Tie the pre-work to the topics by including references and links to the pre-work at the appropriate spots in the agenda.
  • Mix Up the Modalities – To keep the meeting out of droning talking heads mode, I mix up the modalities of the ways people work together. It’s typically a mix of large group conversations, small group work and report outs, individual idea generation shared and captured on post-it notes, and one on one peer coaching followed by group debriefs.
  • End with Takeaways, Appreciations and Next Steps – Leave at least 30 minutes at the end of the meeting for participants to share their takeaways and ah-ha’s, express their appreciation to each other, and clearly articulate individual and collective next steps coming out of the meeting.
  • Respect the Clock – Establishing clear time blocks for each segment helps set expectations and keeps the meeting on track. If the meeting starts at 8:30 am or 9:00 am, respect the body clocks in the room by ending no later than 3:00 pm. Meetings like this require a lot of participant energy and brain power. The diminishing returns accelerate after mid-afternoon. Better to end early and leave people fresh than to squeeze in two more hours of exhausted conversation.

Take Big Notes, Send Little Notes – One more process point – take a lot of notes on flip chart pages that are visible to the participants. These can be used to capture the big ideas and action steps, and to confirm alignment throughout the day. When the meeting is over, use the flip chart pages to create a coherent summary of the day’s work and the next steps coming out of it. Send this to the participants within a week of the offsite.

Whew, that reads like a lot! That’s because it is a lot. Strategic leadership offsites are a lot of work – before, during, and after for both the participants and the people prepping and facilitating the meeting. They’re a big investment of time and effort and, when well executed – before, during, and after – are totally worth it. Let me know your thoughts on what makes an effective strategic leadership offsite agenda. Email me or leave a comment on LinkedIn.

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