Leadership Offsite: What They Are and How to Plan a Good One

We’ve all heard the term “offsite” before. We’ve probably participated in several team offsites throughout our professional lives. They are a fundamental and integral part of what it means to be part of a team. They help us align with our vision and goals, grow together as a team, get to know other team members, and importantly, lay the foundation for what we’ll be working on 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 the future of their company.

What do leadership teams do in an executive office?

Unlike other team meetings, the executive team will work on its strategic vision, address key issues, dedicate some time to creative teamwork, and even allocate a slot for team building. The bottom line, though, is that offsite meetings for leadership teams will focus on the big picture. It will typically have a much broader scope than your regularly scheduled management meetings held onsite. They often represent the primary opportunity for upper management to carve out a specific time slot just for this.

They will usually deal with some big questions for the business. Which direction is the company going? Is our company culture growing and shaping with us? Where are we leading this company for the next 5 or 10 years from here? These meetings are about peering across the horizon and conceptualizing a vision of the future that will shape real decision-making in the months and years ahead.

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

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

1. Know what this meeting has to achieve

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

2. Set up your action plan

Once you understand what your attendees expect from this all-important meeting, set up a checklist of tasks. What do you need to do to make this offsite a reality? Here are some examples:

  • Venue and facilities – Depending on the goals you have specified for this event, you need to find the corresponding venue. For example, if what the leadership team wants is laser-focused 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 some team-building, you need to make sure your venue can accommodate that.
  • Transport – Figuring out how to get the team comfortable to and from the venue can be difficult. When you want an inspiring location, you 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. For example, hosting an offsite on an Airbnb with lots of common space is a great way to encourage team bonding!

3. Create a careful offsite agenda

As with everything, your meeting agenda should be based on the goals your leadership team wants to achieve. You can create a detailed agenda consisting of “talking blocks”, each dedicated to a different theme. What’s more, your agenda should include the purpose of each slot, not just deadlines and speakers. By clarifying what needs to be accomplished in each session, your agenda serves as a catalyst for a goal-driven meeting.

It can also be helpful to provide participants 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 effective.

4. Assign a session moderator to each discussion

Often when meeting in person, regardless of who is involved, enthusiastic conversations can descend into chaos. It can be so easy to unconsciously steer a conversation towards the one topic a person most wants to discuss. Designating a moderator for each session from among your participants will help keep the conversation relevant and on track.

This person may also be responsible for ensuring that all opinions are heard in equal measure, all planned topics are covered, and all relevant data is presented in a timely manner. They can help maintain the momentum of a particular discussion, or block a topic that will be discussed at another time.

5. Help your leadership team prepare their content

It is imperative that every member of the management team be prepared for this offsite. If you are planning the event and arranging the agenda, it stands to reason that you will need to help coordinate their content. It is likely that for each session, a different team member will lead the conversation and as such will require clear messaging and even visual aids.

Now, you don’t actually have to write content for them. Many leadership team members prefer to do this themselves or keep it to a small pool of collaborators. That being said, an integral part of a successful leadership offsite plan is making sure everyone knows what is expected of them and is ready to bring their contributions to the table.

Are you planning a leadership team offsite soon?

If you’re tasked with planning an offsite soon for your leadership team, it can be difficult to know where to start. More and more companies are organizing private events to bring people together in a post-pandemic world. If you need some help getting started, don’t hesitate to contact us or request a demo soon!

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