Elements of a Great Offsite Meeting | Mark MacLeod

December 7, 2022 - Mark MacLeod

Elements of a Great Offsite Meeting

It’s that time of year when leadership teams are meeting to plot and plan for the coming year. So, here are some thoughts on how to create a great exec offsite meeting.

Onsite vs offsite: Choose the right environment

Many companies have offices sitting vacant at the moment. It can be tempting to get into a board room there. But that context is not offsite for people. It’s not a change. I know you’re wasting money on rent but consider actually getting away.

Choose a venue out of the city for your offsite meeting. Hard-charging execs likely don‘t spend enough time in nature. 60 – 90 minutes travel time at most.

Consider traveling to the offsite together

It was a bit cheesy, but in a previous role, we took a stretch limo together to and from our offsites. We relaxed and bonded instantly. As a side note, they are not as comfortable as I would have expected. But the benefit in terms of bonding was there.

Get everyone involved in offsite planning

Many CEOs take it all on their shoulders to come up with an agenda and plan the offsite event. To me, Exec off sites are like potluck dinners – everyone brings something. Everyone contributes to the agenda. It is a shared success.

Poll your leadership team and what they did and did not like about previous offsite meetings, what would be most valuable to cover now, and come up with a plan for this one together.

Insist on focus

This should be a rule for all meetings, not just an offsite, but nobody should be doing email or checking Slack while the meeting is on. Now, your leaders have functions to run. The world doesn’t stop for them. So, this means scheduling in breaks to allow everyone to check in and respond to people and issues.

Consider a meeting facilitator

If you are leading the meeting then you are not sitting back and thinking like the rest of your team. Consider having a 3rd party running the working sessions.

Bonus points if that facilitator is trained and can lead you all through a personality assessment or other exercise that helps everyone better understand their team members.

Celebrate & recognize your team

Startups are really bad at this I find. Because the expectations are so high. Because we have never ‘arrived’. The roadmap is never done. The revenue is never enough.

This hunger is good. It promotes striving for greatness. But it is also relentless. Stop and smell the roses together. As you sign up for another mountain to climb next year, stop and recognize the mountain you just climbed!

Include some fun offsite activities

Not unrelated to the last point. Schedule some fun activities. I have done past offsites at wineries, and glamping sites, and have gone zip-lining, and canoeing for hours. These are important moments in helping the exec team actually be a team.

Nail your next offsite meeting

There you have it. Give these suggestions a try at your next offsite. These are important meetings that can have a big impact on your team and your company’s results. Take the time to get them right for maximum impact and enjoyment.

Photo by Campaign Creators on Unsplash

Your journey is never done

Sign up to my newsletter and join an inspired community of leaders who realize that the journey to achieving their full potential is never done.

    If you’re curious about my coaching and deal work you can learn more here.

    back to blog

    Latest Blog Feed

    From Burnout to Balance: Chris Savage’s Strategies for Leadership

    Check out my discussion with Chris Savage, the co-founder and CEO of Wistia, on The Startup CEO Show. In this episode, we unpack the deeply rooted values that have shaped Chris’s company, emphasizing the importance of genuine connections, personal growth, […]

    read more

    Competitor Analysis in an AI-Driven World with Jason Smith

    Listen to my conversation with Jason Smith, CEO of Klue, as we dive into the gritty details of building and leading a tech company in the Competitive Enablement space. Dive into the Transcripts for Key Insights from this Episode Mark […]

    read more

    Startup Resilience: How Notch Pivoted to Success with Jordan Huck

    Tune into my conversation with Notch’s CEO, Jordan Huck, where we dive into the critical decisions and pivots that shape a startup’s journey. Delve into the Transcripts for Key Takeaways from this Episode Mark MacLeod:Jordan, welcome to The Startup CEO […]

    read more


    Email : me@markmacleod.me

    Follow me:

    Mark MacLeod ICF Member

    Send Me A Message