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Leadership Offsites

PREMIUM PLAYBOOK & TOOLS

Leadership Strategy Offsites


Companies often host offsite meetings with the hope that executives will leave energized, inspired, and tasked to bring their teams to the next level. A lofty goal like this is well worth the time, assuming the meeting is productive.


Unfortunately, many offsites don’t accomplish this goal and when that’s the case, the whole trip is a huge collective waste of time.  There are usually many reasons for this failure, but in my experience the big ones are:


  • They don’t address the real problems in the team

  • Too much is packed into the agenda and it’s more like a task list

  • The loudest voice wins and we don’t hear from everyone

  • We think making time with each other creates connection

  • We don’t discuss the elephants in the room well enough, or at all

  • There is not a close enough linkage to the business operations and strategic choices


Some of these failures are easier to avoid than others.  The good news is there is a standard playbook on the do’s, don’ts and best practices to holding an awesome and productive offsite.  Just some of these include:


  • Clearly articulate the objectives – Make sure everyone is aiming at the same target and know in advance what you hope to accomplish. Obvious yes, but often skipped.

  • Don’t try to 'boil the ocean' - Attack a limited number of items and go deep on each in order to bring them to meaningful conclusion.   Trying to cover too much ground is a recipe for being unproductive.

  • Pick an inspiring location – A dimly lit hotel conference room won't maximize creativity.  For centuries, artists and musicians have gone to inspiring places to be inspired.  Pick a location and venue that will stimulate the senses.  AirBnB works a treat.

  • Demand brutal honesty – There's a great African proverb - "when friends argue, truth happens".  Encourage friendly fire and realize that direct feedback is a gift.  The more candor, the better the results.  It’s hard and subtle to get right, but worth the effort.

  • Start and end big – The opening and closing are the most important segments, just like a fireworks show.  Start with the big vision and end with something inspirational that will encourage the team to seize their full potential.  Starting with "housekeeping" and ending with "announcements” will kill momentum.  Don’t be boring.

  • Keep a "parking lot" list – Engaging discussions can easily wander off topic.  Keep a running list of ideas or discussion topics that come up so that you can keep conversations focused and then attack your parking lot list later in the agenda.  This will avoid distractions and ensure that important topics don't run off course.  Your Chief-of-Staff has a vital role to play here.

  • Each session should have an outcome – After each segment, the team should agree on what happens next.  What are the next steps?  Who has primary ownership? What is the deadline?  Feel-good sessions that lead to no action are pointless, so make sure each topic has a specific action plan before moving on to the next.  Send out a summary of these and incorporate offsite actions follow-up into your weekly exec actions list.


Done right your Exec offsite is inspiring and energizing.  As a general rule, for a rapidly scaling business *big* multi-day offsites should take place twice a year with your senior team. If you are growing rapidly and/or find you have lots to discuss doing a day-long “onsite” offsite in the other two quarters followed by a dinner may make sense as well.


Probably the single thing that has the biggest impact on the culture of an organization is the culture of the leadership team. When the leadership team is aligned, the culture is healthy, naturally everything else just gets better.  The offsites you hold together are an absolute cornerstone of getting the leadership team working together, so don’t screw it up.


I have nearly two decades of experience planning and facilitating Exec team offsites - including nearly a decade running Google's leadership team retreats - so I have plenty of ideas on how to make these some of the most impactful time you spend with your team.   In the ScaleUp System you get everything you need to outline, build and run an off-site everyone remembers and wants to do again.  Except sunshine and good food and drink.  That you need to provide for yourself. :-)


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