By Chief Maker Executive Development Academy

Team Offsites, Executive Retreats or Strategic Planning Meetings are a critical element in the annual calendar for any business. They are a magnificent method for building trust amongst your team, getting aligned on your purpose, paving the way forward and having some well-deserved fun. 

Unfortunately, a lot of organisations are sceptical about running these annual events. They see it as ‘another two days wasted, out of the office and away from important work’. They haven’t budgeted for travel or a venue, and they certainly haven’t budgeted for an external facilitator to help navigate the process. They are cautious to proceed without help, and so often, they don’t proceed at all.

With the rise of hybrid and remote workforces, it’s more important than ever that businesses make time for their people to get together, in person, to talk about vision, strategy, roles, metrics, purpose and values.

So whether it’s your first time preparing, or your fifth time planning, here are 10 steps to help you facilitate a team offsite that will inspire and invigorate your people. 

 

1. Diagnose your biggest challenges 

Start by gathering some data and analysing the most important problems or challenges you need to solve. Put together a survey for your people, collate the responses, and identify what’s most pressing. By focussing on what’s most important, your meeting will have an intention and your people will see it as a valuable use of time. 

 

2. Form a clear agenda (but be flexible) 

A clear agenda, distributed ahead of time, is crucial for everyone to mentally prepare for what is going to be discussed. But remember, as the conversation flows during your meeting, you must be prepared to leave the agenda if necessary. If this happens, have the courage to address an elephant in the room - never ignore it.

 

3. Have great templates

If you’re doing strategy work, make sure you’ve got the best templates you can possibly get. If you want to tease out a new vision, have a process to follow. If you’re trying to establish a new operating rhythm, get a framework for doing so. Your sessions will run smoothly and you’ll get far more out of your people if you have a process to follow.

 

4. Share session facilitation

If it makes sense, give everyone in your team a session to facilitate. People love being involved and having responsibility, particularly if it’s a topic they know a lot about. It also helps share the workload and reduce the monotony of a single voice facilitating the entire offsite. Just make sure you give them plenty of notice so they can prepare accordingly. 

 

5. Go off grid

Get out of the city and as far away from your office as possible. You want to connect with nature - land or sea. And you want your people to truly disconnect so that they have the space to find creativity and innovation. If you don’t have the budget for a fancy hotel, find a cool AirBNB and do it yourselves.

 

6. Serve one another

Change it up and do things differently. Cook for each other, clean together, take turns organising activities. This shared approach has an amazing effect on the group and makes people feel involved. It’s a great way of tightening the bonds and discovering connections amongst your team that you never knew existed.

 

7. Establish the rules of the game

At the very start of your retreat, make sure everyone understands the basic rules around phone use, leaving the room and staying present. Also consider the language you use, reinforce your company values and make sure everyone shows respect for one another. You want the best version of each person in the room, and nothing less is acceptable. 

 

8. Find time to tell a story

Make sure that storytelling is part of your agenda - around the dinner table or a campfire. Ask people about their family, something they’ve done that defines them, or perhaps their favourite movies or songs. This personal activity forms connections, builds trust and humanises the experience. 

 

9. Make sure you hear from everyone

Keep an eye out for people who don’t speak up as much. If you’re brainstorming, don’t just have people fire ideas out loud - you’ll only hear from your extroverts. Instead, give everyone a minute to write down their ideas first. Then ask each person to share their answers. This gives your introverted leaders a comfortable way to engage and ensures every single person is heard. 

 

10. Wrap it up

Finish your retreat with a clear list of tasks and who is responsible for doing them. Communicate this with everyone involved and hold them all accountable. For your executive retreat to have real impact on the business, you must be able to measure progress and see the results.


These ten steps will ensure you plan and facilitate a smooth running, results-driven team offsite that everyone raves about. But remember, you can’t have an annual staff offsite without having quarterly, monthly and weekly meetings to make sure your team is executing the company strategy. This is known as your Operating Rhythm and it’s your pipeline for automating productivity and accountability amongst your people. 

Build these habits and routines now, and you’ll be creating a real drumbeat for the success of your business, all while motivating your people and driving tangible results.