Each year I plan and organize a Winter Strategic Retreat for the leadership team at Port X Logistics.  I find this to be the most important time of their upcoming year. I take the team off site to a place that is relaxed and comfortable. No boardroom tables with leather chairs. The team comes in their sweats, hoodies, and slippers if they choose! The environment is safe and casual allowing them to let their guard down and get real. 

I never use a typical retreat center. I find casual spaces with couches and comfortable chairs. For example, Airbnb’s or boutique hotels. This is an organized event, but there is nothing formal about it. In my experience the most meaningful discussions happen when teams are in a creative head space, absent of the noise or chatter of the daily grind. This year I took the @portxlogistics team to @innbuffalo in Buffalo, NY. It was perfect.  

Here is the process I follow to ensure a successful and productive retreat: 

  1. PLAN AHEAD: You can’t pull together a meaningful leadership retreat by planning the week before, or by spending only an hour or two thinking about the agenda. Invest time thinking about the intention and desired outcomes. What does the team need to accomplish during the retreat and how do you need to design an agenda to effectively meet those goals? Ideally you should share the plan with the team weeks ahead of time, to set expectations, be transparent, and arouse thinking around what you’ll be focusing on. 
  2. ASSIGN PRE-WORK: To make the best use of the team’s time together I assign pre-work. Our strategic planning retreat is only three days, so time is limited. The team needs to be prepared and focused from the start. The pre-work helps the team come ready to dive into the bigger, more challenging topics and discussions. 
  3. GET A FACILITATOR: Do not try to lead your own retreat with your team. It’s difficult to facilitate your own team and be a participant. You cannot fully immerse yourself in the conversations adding your insights if you’re worrying about managing the agenda and time. I am the facilitator of the Port X retreats to ensure they stay on time and task. I also ensure each member of the team has equal participation and involvement. 
  4. DON’T RUSH: It’s critical that you allow enough time and space for discussions — real discussions. Do not over book your agenda. The intention for time spent out of the office is to have deeper conversations with ample time to explore. The goal is to slow down the pace so ideas, thoughts and discussions can go deep and be more meaningful. 
  5. PLAN OF ACTION: I take notes throughout the retreat keeping track of action plans. Once the team returns to the office, I hold them accountable to the plans they have developed. You may have had great conversations, but if you don’t commit to doing something, all those great ideas and new insights will be lost as soon as you step foot back in the office. Commit to a detailed action plan, before you leave. And make it a priority to follow up.

Leadership retreats can be transformational if they are productive. Additionally, they will have an impact on your leadership team providing an opportunity to build camaraderie, trust and connection. I have witnessed some of the most impactful leadership discussions happen during a game of billiards after a shared dining experience. 

Think about what your team needs to focus on this year? Is there a strategic plan in place that provides direction and specific goals and outcomes? Does your team have the headspace to think, reflect and explore new ideas? Maybe its time to consider a leadership retreat for your team.