Successful Strategic Retreats

January 24, 2019

Successful Strategic Retreats

As I’ve become deeply immersed in the world of strategic retreats for mission-driven organizations, several people have asked me for some tips on how to lead successful sessions – workshops, retreats, etc.  

Oh the irony….. as I was (and still am!) one of the hardest-to-please retreat participants, finding flaws or being bored in my 15+ years of professional development in the corporate and education sectors. However, a handful of great sessions – plus years to research, craft, practice and refine my own – have left me with a base set of guidelines that I use to design and execute my own strategic retreats:

  1. Know your audience!  This is pretty much my #1 rule in life and is especially pertinent when I facilitate retreats with audiences that don’t know or trust me.  To know my audience, I invest participants in agenda creation through a simple, anonymous, survey or if the group is small enough, I conduct short 30-minute interviews (both methods are confidential).  The data from the survey and/or interviews allows me to gauge team culture (I love using Gallup Q12 plus specific questions on goals, priorities, strengths, weaknesses, etc.) and create an organizational SWOT.  In groups with some dissension, I may do a combination of the survey and interviews to determine the right content and activities based on participant preference.  Gathering this valuable insight also provides a foundation for teams’ key priorities, which gives us a head start on setting the organization’s strategy.
  2. Customize content based on team development.  Per Tuckman’s Stages of Group Development,  or per Lencioni’s Five Dysfunctions of a Team, teams must go through many stages in order to cohesively perform.  Therefore, when I lead retreats, I use the participant feedback, as well as the leader’s insights/background data, to determine where the team is on the Tuckman/Lencioni spectrum.  Last year, I led a multi-day retreat that focused more on ‘soft’ areas as the team was struggling with trust, communication and a somewhat toxic workplace environment. We were able to weave in SMART goal-setting for teams and individuals after we built trust amongst team members.  On the flip side, I recently led a small leadership team who wanted to get straight to work on strategy setting – but even here, it’s necessary to have some brain breaks and team bonding activities to keep the energy up.

  3. Keep it interesting.  The majority of learning in my life (high school, college, professional development, etc.)  has been through whole group formats….how boring is that?! I learned very quickly as a 6th grade teacher to use a variety of engagement formats:  think/pair/share, breakout sessions, turn and talk to a partner, games, role play, etc. This is especially important if you are leading a longer session and the post-lunch-afternoon-lull sets in – this is when I put my most energetic activities to keep people excited and learning.

  4. Be prepared.  Ok, this is tied with “know your audience” for my #1 rule in life.  I detest being unprepared and this is amplified 1000x when everyone is looking to you for a flawlessly executed event – whether it’s a 1-hour session or a weekly retreat.  I’m a hawk when it comes to details, and I schedule in multiple rehearsal times to make sure that I have 99% of the session ready prior to the actual execution. It helps to become really good friends with the venue contact (Can I get in early? Who can help me setup the internet/projector?), as well as the organization’s key logistics person (who is usually not the team leader) to help with flawless logistics.  Finally, as obvious as this sounds, hungry/uncomfortable teams can’t focus on learning – so bring in lots of snacks and water, plan accordingly for breaks and meals, make sure the temperature is comfortable, etc.

If you lead retreats or workshops, I’d love to hear your ideas on how you execute successful events!


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