Designing Your Leadership Team Retreat - 3 Planning Questions

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I'm just returning from a time in the mountains. 

Breathing in the Colorado mountain air this week, I sat with an executive at a four-day leadership retreat. He exhaled after a full week he shared, "I know this will make me a stronger leader. " Then in an emotional moment he reflected, " I believe this will change my life as a human. It's making a difference from the inside out and who I want to become a better husband, father, and at work."

Coaching alongside this man I learned that ultimately he felt guilty about taking time away. I asked him a question I believe was at the heart of the issue. Where do you find joy in life? Once again with tears in his eyes, he told me about his three and seven-year-old sons. He's missing some of the memorable moments in their life. His love for hunting and fishing was evident as he talked about stories of getting outdoors. "When's the last time you did some of those things?" I asked. It has been over a year for fishing and three years for hunting. I want to get my boys out with me. Every year in January the HR director asked me about my vacation plans and I laugh because I feel guilty for taking time away from the duties of work. 

It turns out that he's not alone 54% of millions of Americans have unused vacation time because they feel that by leaving that reduce their value to the company and could be replaced even though their bosses encourage them to go. This executive specifically had some issues with the long-term impacts of chronic stress and how it was affecting his attitude expressed in anger among his team members. After my meeting with him, I could he see he was a good-natured and kind-hearted man. However, his 360 reviews showed some of the internal challenges that were beginning to wear him thin. I asked him how can you possibly deal with conflict and manage your stress if you're not getting time away to enjoy life. Then I discovered he has trouble sleeping and deals explicitly with issues of sleep apnea. The issues were catching up to him. 

17 years on the job he indeed has shown his commitment to the company and the work before him now the effects of not having healthy rest and recreation room crippling his effectiveness. Even though team members are encouraged to take a break and do the things they love for one reason or another it just doesn't happen. Sometimes a team leadership retreat gives the space in the conversations to focus on what truly matters most. Often, personal vacations are working weeks away from that we feel like we need a vacation from our vacation by the time we're back at work.

As a facilitator of team retreats, I've consistently observed that when you create space to talk about the issues of business as well as your health as an individual, it begins to form a mindset for change.

When you're team needs a breakthrough maybe what they need is a break.

It's these breakthrough moments that often come by getting out of the office on the mountainside or lakeside that is a joy to witness.

Whether it's summertime or your fall season, this is a great time to begin designing a time that meets the needs of your team.

I would encourage you today to examine...

1. What does your team need to thrive? 
2. What are barriers holding them back? 
3. What would be the impact of a healthy, unified, trusted team?


For most leaders and executive teams, this is new territory. When they take time to work on their business it's offsite including an agenda it leaves little room for discovery and development.

After years and hundreds of team engagements, I've observed the principle that Investing in your WHO (team) will make an exponential impact on the effectiveness of WHAT they do. 

Your first step might be a fun activity to celebrate some of the wins of your business. It could be a lunch to say thank you after working through a difficult season. It may be a half-day planning session somewhere outside of the office. Still, you may sense there is untapped potential, and you're not sure how to unlock your team members. It may be a four-day leadership retreat that will be the catalyst for new growth and connection for your organization. 

Wherever you find yourself today entering this summer a few minutes of creativity, planning, and scheduling a date will be well worth the investment building your team.

If you need help designing or executing your leadership team retreat we're here to serve you.