Leadership offsites: what they are and how to plan a good one

29 Sept 2022 · 6
We’ve all heard the term “offsite” before. We’ve probably even attended a number of team offsites throughout our professional lives. They’re a fundamental and integral part of what being part of a team means. They help us align on our visions and goals, grow together as a team, get to know other team members, and importantly, form the foundation of what we’ll be working towards for the coming year.
That’s not all that different for leadership teams. Almost all management teams around the world take a day or two each year to come together and plan for their company’s future.

What do leadership teams do at an executive offsite?

Not unlike other team meetings, the executive team will work on its strategic vision, tackle key issues, dedicate some time to creative teamwork, and even allocate a slot to team building. The bottom line, though, is that offsite meetings for leadership teams will focus on the big picture. It’ll have a much broader scope than your more regularly scheduled management meetings that usually take place onsite. They often represent the primary opportunity for upper management to carve out a specific slot of time just for this.
They’ll usually tackle some of the greater questions for the business. What direction is the company headed in? Is our company culture growing and shaping along with us? Where are we steering this company from here to the next 5 or 10 years? These meetings are about peering beyond the horizon and conceptualizing a vision of the future that will shape practical decision-making in the months and years to come.

How can you create a leadership offsite with a lasting impact?

What does a successful offsite for leadership teams look like? It’s about more than just choosing the right hotel and the perfect dates. You want to organize an offsite for your leadership team that’s going to have a lasting effect, and generate the right conversations that will yield the results you want. So, how can you do that?

1. Know what this meeting needs to achieve

Before you even start planning your executive offsite, understand what the leadership or management team needs to get out of it. Generally, these offsites tend to focus on strategic planning for the short, medium, and long term - but what that actually looks like will vary from team member to team member. That’s why your first step should always be to sit down with each person to understand their needs and expectations.

2. Set up your action plan

Once you’ve understood what your attendees are expecting from this all-important meeting, set up a checklist of tasks. What’s everything you need to do to make this offsite a reality? Here are just a few examples:
  • Venue & amenities - depending on the goals you outlined for this event, you’ll need to find the corresponding space. For example, if what the leadership team wants is to laser focus on brainstorming and problem-solving sessions, you’ll need a hotel or an Airbnb with a comfortable conference room. If the team also wants to add in a bit of team-building, you’ll need to make sure that your venue can accommodate that.
  • Transportation - figuring out how to get the team comfortably to and from the venue can be tricky. While you do want an inspiring location, you also don’t want to make it a hassle for them to get there and back.
  • Accommodation - this is another great example of a tool to help you achieve the goals you set out for. For example, hosting an offsite in an Airbnb with plenty of common spaces is a great way to encourage team bonding!

3. Develop a careful offsite agenda

As with everything, your meeting agenda should be based on the objectives that your leadership team wants to achieve. You can create a detailed agenda comprised of “talking blocks”, each dedicated to a different theme. What’s more, your agenda should include the objectives for each slot, not just the timeframes and speakers. By making it clear what is to be achieved in each session, your agenda acts as a facilitator for a goals-driven meeting.
It can also be helpful to provide attendees with a tool like Miro that gives them access to templates for different frameworks. Things like a SWOT table, a BCG matrix, or a lean canvas are just a few examples of useful tools to make each session more actionable.

4. Assign a session moderator to each discussion

Often when meeting in person, spirited conversations can descend into chaos regardless of who is involved. It can be so easy to get off topic or to unconsciously steer the conversation towards a topic an individual wants to discuss most. Nominating a moderator for each session from among your pool of attendees will help keep the conversation relevant and on track.
This person can also be responsible for making sure that all opinions are heard in equal measure, that all planned topics are covered, and that all relevant data is presented in a timely fashion. They can also help keep the momentum of a particular discussion going, or block a topic that would best be discussed at another time.

5. Help your leadership team prepare their content

It’s essential that each member of the management team is prepared for this offsite. If you’re planning the event and sorting out the agenda, then it stands to reason that you’ll need to help coordinate their content. It’s likely that for each session, a different team member will lead the conversation and as such will require clear messaging and maybe even visual aids.
Now, you don’t have to be the one to actually write the content for them. Many leadership team members prefer to do this themselves or keep it among just a small pool of collaborators. That being said, an integral part of planning a successful leadership offsite is making sure that everyone knows what’s expected of them and are ready to bring their contribution to the table.

Are you planning a leadership team offsite soon?

If you’ve been tasked with planning an offsite for your leadership team soon, it can be difficult knowing where to start. More and more companies are organizing in-person events to bring people together in a post-pandemic world. If you’d like some help getting started, don’t hesitate to reach out to us or request a demo soon!
Written by
Sofia Bogunovic
Sofia Bogunovic
Brand Content Manager at TravelPerk
Train Plane Travel

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