Breakthrough Or Boondoggle? 3 Ways To Make Your Next Executive Offsite Pay Off

They're working out in the fresh air today

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As we head into the final months of 2019, leaders are increasingly focused on 2020 and beyond. Given that it’s a “decade” year, many executive teams will take the opportunity to reflect on the past (hindsight’s 2020!) and look to the future.

An executive offsite is an ideal forum for that deeper level of reflection and more expansive exploration. Sadly, the term may bring to mind a regrettable blow-the-budget dinner in Napa or bizarre scavenger hunt around London. Perhaps you’ve traveled to some gorgeous setting only to sit in a windowless room for three days or used a tree’s worth of flip charts, without much to show for it.

Those risks are real, but so are the upsides. A well done offsite can yield an energized team, smarter decisions, bolder aspirations and a greater readiness to execute in the long-term.

Have an offsite on your horizon? Here are three tricks of the trade to create a breakthrough, not a boondoggle.

1. Build The Agenda Around Questions, Not Topics

The best executive retreats are built around a curated set of big questions that don’t get answered in the course of regular work. While your big questions will be specific to your situation, here are a few powerful examples:

  • Reflection: What surprised us in the last year? What capabilities and strengths will be a source of competitive advantage going forward? In the areas where we excelled or fell short, what are the real lessons learned?
  • Current Context: What core beliefs or assumptions are driving our strategic choices? Which of those should we challenge or adapt? What’s changed internally or in the market that creates new risks or opportunities for us?
  • Future-focused: What do we want this organization to look like in X years? What will it take to get there? Is our current course and speed enough to achieve our long-term aspirations? If not, how much of a shift is required? What would need to change?

Use your upcoming 1:1s or leadership team Slack channel to source potential questions. Narrow in on the best ones, decide on the logical sequence, and identify the data or other inputs needed to have rich, informed dialogue during the retreat.

2. Secure A Physical Space That Supports The Purpose Of The Retreat

If you’re investing the time, invest the money for a location that will elevate the conversation. The absolute worst choice is the conference room you use every day. Just being in that room will trigger a “business as usual” mindset, which undermines the whole purpose of an offsite.

If you have the budget for a nice offsite location, go for it. But if not, finding somewhere just a little out of the way can make a big difference. Consider meeting at a team member’s home or securing a unique venue on Liquid Space or a similar site. If your organization has other buildings or is in other cities, you can head to one of those for an “onsite offsite.”

There are plenty of options from affordable to opulent. In making your decision, optimize for natural light and access to fresh air, along with privacy and plenty of space to move around.

3. Sustain Energy And Focus

It’s a retreat—a time to think and replenish. A packed agenda and too many slides will sap the energy (and potential) right out of the room. Instead:

Build white space in the agenda

  • Have fewer, longer sessions. The best conversations in an executive retreat tend to be 90 minutes or more
  • Start late or end early so the team has time to address urgent issues, get in a workout, connect informally, call home, etc.
  • Schedule a real lunch (60 – 90 minutes) to allow for informal conversations or a walk around the block and make the breaks long enough (20 – 30 minutes) to get something done

Design for active engagement

  • Minimize “inform” conversations. Use pre-reads or pre-briefings so the time at the retreat is dedicated to dialogue
  • Minimize the slides. Don’t project anything if you can possibly avoid it. If your group needs ready access to specific data, print it
  • Keep the topics at the higher altitude. Resist the temptation to throw in a “business as usual” item, as they will pull everyone back to reality

With these time-tested strategies, you will be able to use your 2020 executive retreat to bring your future into perfect focus.


Shani Harmon and Renee Cullinan founded Stop Meeting Like This to change the way the world works. Follow them on LinkedIn and Twitter, and subscribe to their quarterly newsletter.

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As we head into the final months of 2019, leaders are increasingly focused on 2020 and beyond. Given that it’s a “decade” year, many executive teams will take the opportunity to reflect on the past (hindsight’s 2020!) and look to the future.

An executive offsite is an ideal forum for that deeper level of reflection and more expansive exploration. Sadly, the term may bring to mind a regrettable blow-the-budget dinner in Napa or bizarre scavenger hunt around London. Perhaps you’ve traveled to some gorgeous setting only to sit in a windowless room for three days or used a tree’s worth of flip charts, without much to show for it.

Those risks are real, but so are the upsides. A well done offsite can yield an energized team, smarter decisions, bolder aspirations and a greater readiness to execute in the long-term.

Have an offsite on your horizon? Here are three tricks of the trade to create a breakthrough, not a boondoggle.

1. Build The Agenda Around Questions, Not Topics

The best executive retreats are built around a curated set of big questions that don’t get answered in the course of regular work. While your big questions will be specific to your situation, here are a few powerful examples:

  • Reflection: What surprised us in the last year? What capabilities and strengths will be a source of competitive advantage going forward? In the areas where we excelled or fell short, what are the real lessons learned?
  • Current Context: What core beliefs or assumptions are driving our strategic choices? Which of those should we challenge or adapt? What’s changed internally or in the market that creates new risks or opportunities for us?
  • Future-focused: What do we want this organization to look like in X years? What will it take to get there? Is our current course and speed enough to achieve our long-term aspirations? If not, how much of a shift is required? What would need to change?

Use your upcoming 1:1s or leadership team Slack channel to source potential questions. Narrow in on the best ones, decide on the logical sequence, and identify the data or other inputs needed to have rich, informed dialogue during the retreat.

2. Secure A Physical Space That Supports The Purpose Of The Retreat

If you’re investing the time, invest the money for a location that will elevate the conversation. The absolute worst choice is the conference room you use every day. Just being in that room will trigger a “business as usual” mindset, which undermines the whole purpose of an offsite.

If you have the budget for a nice offsite location, go for it. But if not, finding somewhere just a little out of the way can make a big difference. Consider meeting at a team member’s home or securing a unique venue on Liquid Space or a similar site. If your organization has other buildings or is in other cities, you can head to one of those for an “onsite offsite.”

There are plenty of options from affordable to opulent. In making your decision, optimize for natural light and access to fresh air, along with privacy and plenty of space to move around.

3. Sustain Energy And Focus

It’s a retreat—a time to think and replenish. A packed agenda and too many slides will sap the energy (and potential) right out of the room. Instead:

Build white space in the agenda

  • Have fewer, longer sessions. The best conversations in an executive retreat tend to be 90 minutes or more
  • Start late or end early so the team has time to address urgent issues, get in a workout, connect informally, call home, etc.
  • Schedule a real lunch (60 – 90 minutes) to allow for informal conversations or a walk around the block and make the breaks long enough (20 – 30 minutes) to get something done

Design for active engagement

  • Minimize “inform” conversations. Use pre-reads or pre-briefings so the time at the retreat is dedicated to dialogue
  • Minimize the slides. Don’t project anything if you can possibly avoid it. If your group needs ready access to specific data, print it
  • Keep the topics at the higher altitude. Resist the temptation to throw in a “business as usual” item, as they will pull everyone back to reality

With these time-tested strategies, you will be able to use your 2020 executive retreat to bring your future into perfect focus.


Shani Harmon and Renee Cullinan founded Stop Meeting Like This to change the way the world works. Follow them on LinkedIn and Twitter, and subscribe to their quarterly newsletter.

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We cofounded Stop Meeting Like This to revolutionize how work gets done. We help complex, global organizations become more agile, productive, innovative, and energizing....