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Checklist for a Successful Strategy Offsite

Hello, 2022!

It’s a new year, which means executive and leadership teams are gathering for strategy sessions.  It’s time to advance your strategic plans. It may also be an opportunity to bring your team together for the first time in a long time.  


A successful strategy offsite can mean the difference between a company grinding along and thriving. However, pulling it off takes careful planning and execution. The below outlines critical steps that apply in-person, virtually or a hybrid of the two to ensure your next offsite creates a clear and compelling path forward:


  • Define the goals: Focus the offsite on 1-2 business priorities instead of trying to solve every challenge in the business. Make the meeting norms and professional commitments clear, and have a moderator or assigned facilitator keep everything on track. The standards should include closed laptops or apps, a parking lot for off-topic ideas, time limits of sessions, guidelines to ensure every team member has a voice, etc.

  • Pre-reads: Circulate specific pre-read content aligned with the 1-2 business priorities and discuss them throughout the offsite. Content consumed before the meeting helps ensure that the forum doesn’t waste time orienting the team.  Even better, have an objective facilitator lead a project based on the pre-reads to increase the interactivity and incentive for reading and processing the information.

  • Over Communicate: Ensure the team knows what to expect and set expectations with their team, stakeholders, clients, etc. Location, planned breaks, any logistical steps should be precise, and it’s essential to stick to the timeline. Possessing clear information will reduce stress and improve focus amongst the team and clarify envisioned results and enable your team to remain focused.

  • Avoid failure by PowerPoint: I can't stress this enough. Attendees spending two weeks on a presentation delivered to their peers will ensure that they only focused on a solid showing instead of learning and collaborating. If you would like team members to contribute content, ask them to gather their thoughts on a single-page document that will be included as a prerequisite. It should be forward-looking instead of a focused retrospective. A helpful component would be some thoughts through a SWOT analysis framework that looks at external and internal factors.

  • Bring a whiteboard and sticky notes: Stay off a digital screen as much as possible.  Offsites should be a dynamic, living and breathing journey.  Leverage techniques such as brainwriting, mind maps, and SCAMPER. Documenting on a whiteboard with sticky notes will make the offsite progressive and collaborative.  If you’re running a virtual or hybrid offsite, I recommend using Miro.

  • Create a means to measure accountability: Tie the takeaways from the strategy offsite into the company and team goals. The first progress check-in should be no longer than two weeks out.  Don't walk away from the offsite without a mechanism to measure and create accountability. 

  • Create memories: Last, but certainly not least, make the offsite memorable and collaborative. Attention will wane if the team is stuck in a conference room for multiple days without respite. Find opportunities to create experiences, participate in team activities and projects, and enable team members to truly build relationships with those not part of their typical day-to-day.


Leadership is complex! But a successful offsite doesn't have to be. Get in touch with us for offsite facilitation support if you’re looking for a helpful guide to offsite success!