Executive Retreat Facilitation for High Performers
Strategic Planning Retreats that Go Beyond Trust Falls
Executive and strategic planning retreats provide the space for high-performing teams, founders, and executive groups to dig into the deeper conversations that are difficult to have in the middle of a normal workday. The extra space available allows for a fluid approach and multiple backup plans so that teams can take full advantage of unexpected breakthroughs. These are customized engagements focused on strategy, organic trust-building, difficult conversations, and organizational alignment.
Who These Retreats are For
High-performing teams, founders, executive teams, and boards who:
- Are willing to be uncomfortable in order to win
- Value alignment and progress over individual egos
- Are ready to have difficult conversations
- Want follow-through and traction, not just a ‘nice event once a year’
Key Topics in Strategy Focused Retreats
- Is communication flowing in a manner that optimizes resource utilization?
- What topics do we avoid?
- What are the critical decisions that will impact us in the near, intermediate, and longer term?
- Are there economic, competitive, or sociopolitical forces that may require us to pivot strategy?
- What pressure points do we need to position against as we manage growth?
First Principles of Approach to Retreats
♦ Customization.
One size fits most approaches do not yield optimal ROI. Team retreats are customized to the type and needs of the organization, the personality trends, preferences and dynamics of those attending, and the longer-term goals of the business.
♦ High face validity.
Face validity, means that the team can easily see the value of the activities and how it applies to their teams and their goals. Everyone engages when discussions focus on the gritty work of relationships and organizational goals.
♦ Long-term value.
The best retreats are those in which brief follow-ups can be built into the daily processes. Rather than having an event as a “one-off” day or weekend, it should be used as a springboard for additional strategies.
Fluffy vs. Effective: ROI Failure
- Too often, team-building efforts rely on doing fun stuff together or having an event once a year. While the intention is good, this surface level attempt at team-building yields limited results. Cohesive teams, those marked by high-trust, often take time and intentionality to create. This extra attention on the front end increases the efficiency of the team. They are able to make decisions-more quickly, prevent miscommunication and conflict, and use their resources in an increasingly proactive versus reactive manner. Poorly functioning teams spend a lot of energy managing their own interpersonal dynamics; high functioning teams are free to focus their energy on building the business.
Alternative or Complement to Full-Day Retreats:
Topic-Based Guided Discussions
Not every team wants a full-day retreat, and/or it may not be the right decision for their goals at hand. Some prefer targeted facilitation to guide them through critical conversations and decision-making.
For organizations that want to maximize the investment of a full retreat, guided discussions afford more effective deep dives because everyone is already “warmed up.”
Guided discussions are structured facilitation sessions–typically 2-4 hours, recurring as needed–where we dig into specific strategic or interpersonal challenges. They have high face validity, lower time commitment, and are easier for overwhelmed teams to manage.
“We sat around the table, trying to get to the bottom of some operational issues hindering organizational growth. Part of the problem was that people thought they were speaking the same language, but they weren’t. One of my dominant strengths is that I am a translator. I saw the gaps in understanding, and I forced clarity. I was a little concerned about being tedious, but I knew that if we didn’t understand the premise of each other’s assumptions, the rest of the time would be wasted. Somehow, it started to feel like fun.
It became a fun challenge because what they thought was clearly an easy task on the front end, was obviously not. One of the men watching got into it. I remember him saying, “Wait, I want to play.” Once we figured out the communication conundrum, we moved on to discussing and planning.”
We Put Chocolate In the Center of the Table
It wasn’t just about the chocolate. It was about taking the edge off. Most of these men had been in combat, the police force or both. They’ve seen hard, and they were smart enough to understand that real problem-solving and alignment can be hard. So the chocolate was a tangible way of adding play, of grounding. We were going to relax around the table, talk about hard stuff, eat some chocolate, and get the job done.
The team and I did that for a while – spent each Friday afternoon getting some mileage. We stopped when it was a good pausing point, or when the chocolate was gone, then reconvened the next week.
Guided Discussion versus All Day Events
Guided Discussion Groups
All Day Events
PROS: Budget-friendly, time-efficient, higher face validity, increased traction, organic bonding
CONS: Less exciting than off-site retreat, requires high topic prioritization, less opportunity for fun/new learning.
PROS: Memorable, allows for variety/fun, extended time for slow-to-warm-up members, different environment affords fresh perspectives and casual bonding opportunities
CONS; Learning often doesn’t carry forward, higher investment, time away is stressful for overwhelmed teams
Both options help teams move forward. They can also be integrated—for example, an all-day event that combines fun in the morning with guided conversation in the afternoon. For all-day events, planned afternoons or half-days for followup throughout the year can create significant long-term gains. In order to make the idea a reality, follow-ups should be budgeted and calendared into the annual plan.
Retreat facilitation and guided discussions are available to current clients and to organizations seeking a high-investment, fully customized engagement. If this is the right fit, we’ll design it together.
Coordinating with the primary stakeholder throughout the process, from the initial phone consult to the day of the event, ensures direct and efficient communication on the variables that are most important for a successful event.
I do not submit proposals or extended contracts about what the event will include. These decisions are made during the information-gathering phase as I learn the needs of the organization and its attendees.
Debriefing - The Value that May be Higher than the Event Itself
Team-building events inevitably yield information about each person’s leadership potential, personality styles, cognitive styles, and motivators. Depending on the specific activities, the strengths, needs, and tension points of the team are evident. Sometimes unrealized resources or opportunities become clear. I often meet with the primary stakeholder/leader at the end of the event to discuss these observations and offer recommendations where appropriate.