How (and Why) to Hold a Leadership Retreat

So you have a growing firm. And you have wisely created a leadership team to take some of the weight off your shoulders as an owner and to help manage the day-to-day activity of running the firm.

But have you considered taking them out of the day-to-day activity of running the firm? Have you considered holding an annual leadership team retreat, with just firm owners and leadership team? You should!

Why A Leadership Team Retreat?

My partner and I say to clients we consult with “you can’t read the label on your own bottle.” In order to read the contents, in order to get a higher level view of what is happening inside the bottle, you have to read it from the outside. Running a firm is like that; you cannot work on the higher level, strategic aspects of the firm while you are inside the firm, working on the day-to-day activities of a firm’s operations.

It turns out what is true for our clients, and for my partner and I as firm owners, is also true of leadership teams.

Your leadership team cannot truly assist with brainstorming and problem-solving the higher level strategic initiatives you set as the owner, while they are busy serving the larger team and doing their daily work.

Only by being pulled out of those daily rhythms and work can a leadership take a look at the firm from the higher perspective you share with them as the firm owner, and contribute their thoughts and solutions to the problems you have already identified. In addition, taking them outside of the daily rhythms of work helps your team strengthen their connections to each other and to you as firm owner(s).

That is what a leadership team retreat is all about.

How Do You Run A Leadership Team Retreat?

There are probably as many different ways to run a leadership team retreat as there are firms. I can tell you how we have done leadership team retreats with our team for the past three years (it is an evolving work-in-progress). You may decide to run your leadership team retreat differently. Feel free to be creative with this.

However, it is important to plan the retreat, and to create an agenda that details what you want to cover and how much time you will spend on each activity. Actually, planning is a strategic activity that aids any event, meeting or gathering to be more intentional and effective!

What our Leadership Retreat Looks Like

Here are some of the specific things we do in our firm’s leadership team retreat:

  • We gather our leadership team together in one place for three days. This is particularly valuable to our firm because we are a remote firm with team scattered across the country.
  • We remove all distractions. Of course, there will be a way to check urgent texts or emails. But this should be a time apart from the everyday business of work to enjoy talking with each other about firm and personal goals.
  • We look back on the successes of the past year in meeting the strategic initiatives laid out in the previous year’s retreat. We may have accomplished only some of what we had planned on; that’s okay because the unexpected circumstances of life can affect the timing of our work. But we celebrate what we have accomplished.
  • We look forward with our shared vision of where the firm is going in the coming year; we communicate this to our leadership team and encourage them to ‘catch our vision.’
  • We remind them of their value as leaders. We want them to feel encouraged and joined together in the shared purpose of serving the greater team.
  • We schedule time for our leadership team, both together and individually in separate spaces, to creatively brainstorm solutions to the issues we have picked out as focuses for the coming year. We limit the number of focuses so the team actually has time to brainstorm on these and present some solutions within the limited time we have together.
  • And we eat! We end the days with a meal together before we break for the day, so we can just enjoy each other’s company and connect together.

These are just some ideas of how to run a leadership team retreat. There are lots of other activities you could do to team-build and strengthen relationships before diving back into the daily grind of work. This valuable time together will strengthen your team, provide a jumping-off point for your strategic initiatives during the year, and have lasting positive effects on your entire firm.

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