Leadership Retreats – Making the Most of an Annual Offsite

I enjoy this time of year because it’s when our team starts planning our annual leadership retreat. This leadership offsite is a critical part of our business as it’s one of a limited number of times leadership can work on the business instead of working in the business. We spend much of each day blocking and tackling, and the offsite gives us a chance to take a step back and identify areas for growth and improvement. More importantly, the retreat is a time to further our relationships outside of the normal day-to-day grind, which we believe is critical to developing a trust-based culture amongst leaders.

What is always hard, though, is determining the right formula for the retreat. How many days should it be? When should it be? Where? Who should attend? What’s on the agenda? At Holder, our retreats have evolved, but we believe there’s always room for improvement. As we start planning, we look back on the year prior, what worked and what didn’t bring as much value as we’d hoped.

First, the when. Based on our business we focus on taking a few days in the fall. By then we’ve made progress through the year to review and discuss, yet there’s still time before the year is over to focus and push forward.

Next, the who. At Holder, we’ve found that bringing executive leadership together with associates at the VP level or higher allows us to keep the group tight, but with diverse perspectives.

Next, the fun pieces. The where and even more importantly the what. Location-wise, we aim to keep the destination drivable within a few hours from our offices. Keeping things a little closer to ‘home’ allows us to accomplish a lot in a short amount of time, ensuring we are respecting the personal responsibilities we’re all balancing. We are lucky to have such varied geography within an easy drive from Atlanta – lakes, mountains, even the coast as we get down in the Savannah, St. Simons areas. 

Finally, the most challenging, rewarding, and seemingly ever-changing – what’s the agenda overall, and even more, what’s the focus for our meeting sessions? We try to balance talking about the business with spending time together. This tends to shake out into three working sessions, one to two team-building activities - golf, spa, cold plunge, shooting competitions and, yes, sometimes a bike ride that is WAY more challenging than anticipated - and great meals.

As for our meetings, we have found it productive to spend time recapping the major successes of the year and discussing where we are focused for the remaining months. We also spend time homing in on future growth opportunities. These conversations are led by our executive team members but allow all associates to share perspectives about what they are seeing, hearing, and what they are excited about. From a leadership growth perspective, we have had success bringing in outside experts to speak on various topics. One year the topic was on managing direct reports (managing down) and another year the topic was on improving communication and collaboration across company functions (managing laterally). This outside perspective in an offsite setting provides a safe zone to improve how we function as a team. In my opinion, the best thing that comes out of these sessions is alignment and a shared understanding of how we can all work better together.

So for us, the question is “What’s next?” How do we continue to evolve our formula to be effective and worthwhile from a growth perspective, but also fun for the team? What have you found makes a leadership retreat worth it? What does your company do that is most impactful?