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Five Steps for Hosting Your Next Leadership Offsite

Five Steps for Hosting Your Next Leadership Offsite

author two

Samantha Shankman

4 Nov 2022
3 minute read
Luxury ranch.

Leadership offsites can be significant turning points in any company’s trajectory. The events have the potential to turn ideas into action, shift directions on important projects, and create cohesion among team members. They’re also essential for in-person strategic planning and big-picture brainstorming.

But these offsite meetings are also expensive due to factors including the cost of travel logistics and business leaders’ valuable time. It’s important that facilitators select the right environment and provide context for executives to make the most of their time together in order to make the leadership offsite as productive and enjoyable as possible.

Five Things to Keep in Mind for a Successful Offsite

1. Set the Right Environment

Keep executive offsites between two days and three days. The leadership team is in high demand, and everyone has outside responsibilities. Keeping the offsite to a couple of days during the week will ensure that teams can focus energy on the present initiatives. These leaders also have direct reports, who will be without guidance throughout the event.

After a duration is set, select a venue outside a city center, ideally in nature, with lots of space to walk, ideate, and chat in private. Two examples are ranches under the big Montana sky or secluded beach resorts on the Mexican coast.

2. Provide Context Before Arrival

A point person or facilitator should provide an offsite agenda, including check-in time, on-site amenities, goals for strategic planning sessions, and key decision-making items to consider before arrival. The executive team can make the most of the in-person connections by thinking through the offsite’s goals, preparing relevant metrics, and balancing big-picture strategic planning with the follow-through needed to get there.

3. Create Opportunities for Serendipity

The typical team-building activities associated with an offsite don’t necessarily make sense when it comes to leadership team meetings. These professionals already spend time convening and problem-solving throughout the week. They likely know each other well, having made big decisions together in a virtual or real-life conference room. 

The goal of a leadership team offsite isn’t to promote collaboration but rather to give team members a chance to work through some of the company’s more strategic directions in a more relaxed, open environment. Brainstorming can take place on horseback instead of at the HQ coffee bar, for example, while decision-making can happen throughout the day rather than in a single kick-off meeting. Leaders can air, discuss, and reimagine ideas for the next year without sticking to a template or the clock ticking down to another breakout meeting.

4. Follow Up With Executive Team Insights

While the facilitator might not be privy to what’s discussed at an offsite leadership meeting, at least one attendee should be responsible for drafting a summary of the big ideas and conclusions. This turns an offsite into an action plan and provides business leaders with takeaways.

5. Book With a Team Travel Solution for Optimal Cohesion

Executives are busy folks who often require specific travel plans in order to meet their many responsibilities. The best way to create cohesion when planning such a high-profile event is to provide flexibility and a powerful booking experience with a team travel solution.

How Navan Team Travel Powers Leadership Offsites

The Navan Team Travel tool is an innovative solution for facilitators, travel planners, and executive teams to use when organizing a company offsite. It offers travel managers, HR teams, EAs, and company leaders an intuitive booking platform that takes into account changing country restrictions, company policies, offsite location, and environmental affect to help make the best decisions while streamlining the booking process. 

Even better, the Navan integrated solution comes with Reed & Mackay’s award-winning meetings and events services, including a dedicated event team, dynamic budget management, group travel experts, and 24-hour on-site assistance for proactive support. It combines a state-of-the-art booking platform with experienced agents to provide boutique support for high-touch events.

The executive team deserves an incredible travel experience on its way to discussing ideas that can potentially change company history.

Learn more about how the Navan Team Travel solution can help make your offsite a success.

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