How to plan a successful team offsite or retreat

Taking time out of the office is essential for team development — it’s a unique opportunity to get together in person to discuss strategy and evaluate progress.

Unfortunately, there’s some confusion between a team offsite and a fun team outing. That’s why some articles say that corporate team building is a waste of time and money.


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But there’s a difference between getting your team together to have fun or to improve how it is working.

Some executives believe that merely taking people out of the office — with the help of alcohol and fun activities — will solve all the problems. There’s nothing wrong with having fun. But, improving team performance needs more than bonding — it requires understanding and hard work too.

An effective team offsite can create positive and long-lasting effects.

Here are some suggested best practices.

Differences between Team Building and Team Development

The term ‘team building’ has become more prominent in recent years as organizations want to promote a happy environment. It’s mostly associated with bonding together and improving how everyone gets along. In most of the cases, it’s simply about getting away from the office to enjoy time together.

Most team building activities are fun — somewhat superficial — and create a social context to foster deeper relationships. But, if not managed well, team building activities can backfire — they can bring out hostility and competition between individuals.

Team development, on the other hand, is about taking time to explore and unleash the team’s full potential — it raises self-awareness and focuses on improvement.

Team building retreats are good to build morale and camaraderie but don’t necessarily improve team performance in the long-term. A team development offsite, on the other hand, requires people to work, not just to have fun. It delivers a more intentional, change-oriented, and lasting impact to your organization.

Both can be enjoyable and complement each other. For this article, I use the terms ‘team offsite’ or ‘team retreat’ to refer to team development.

What Are the Reasons to Hold an Offsite?

There are various motives for why teams want to spend time together. Most companies struggle to find time to take a ‘day off’ to work on what matters, while everyday problems keep piling up. As the saying goes, we don’t have time to do it right the first time but find time to do it twice (or thrice).

Based on our experience having facilitated hundreds of sessions, we’ve found that a team offsite is particularly useful for:

  • Building Trust and Collaboration: Fear is a pervasive emotion in the workplace — 7 out of 10 employees silence their suggestions, thoughts, and ideas. This is one of the most often reasons why companies have an offsite — they want to build a safe space to regain trust
  • and communication.
  • Strategy and Alignment: Offsites are invaluable for solving big problems or addressing long-term strategies. They allow leaders to spend time together collaborating, learning, and discovering new territories. By shaping the future together, people are more engaged and aligned.
  • Learning and Experimenting: Whether you are trying to avoid lengthy approval mechanisms, increase accountability, improve self-awareness, or make meetings more efficient, an offsite provides a safe space for people to learn and experiment with new ways of working.
  • Tackle large initiatives: Taking time out of the office is a very effective way to focus on projects that require attention. With fewer interruptions and having the key participants in the same room, your team can make much more progress than when at the office.
  • Team Awareness: Reflecting on collective behaviors, mindset, and achievement helps identify blind spots, areas of opportunities as well as build on what’s working for the team. Providing feedback and addressing tensions help the team accelerate performance.

What are you trying to solve?

Before embarking into a team offsite make sure you define a clear objective for the session. I usually ask clients for three goals and then to prioritize them using the following categories: critical, important, and nice-to-have.

It’s also important to agree on expectations and what the ideal outcome should look like.

The more clear and focused the goal, the more effective the offsite will be. As author Stephen Covey famously said, “The main thing is to keep the main thing the main thing.”

Be ready to reframe the problem

Understanding the problem is the key to designing the right experience. However, keep your mind open. One of the key benefits of an offsite is that the session itself helps to reframe the problem — the real tensions become more evident as the team is solving them.

Most of the times, the initial assessment differs from the real problem. The pre-work phase (interviews, surveys, etc.) provide valuable insights to better understand what’s going on and bridge the gap between what management sees and what the team members observe.

Acknowledge there’s a problem

Most senior executives tend to minimize people or cultural issues — they are either too detached from the frontline or idealize the reality of their organization.

This is hard for many executives to accept. I usually notice certain skepticism among leaders — their teams are more excited about the prospect of an offsite, but CEOs tend to be more hesitant. One of the reasons is that team retreats open many doors — not everyone is ready to listen or to feel exposed.

However, tensions won’t disappear because they are not addressed — they actually get worse.

Plan Your Team Offsite Ahead

Who owns it?

A team offsite involves a lot of planning and people. Usually, either leaders want to be in charge, or they delegate the authority to one person or small team. Our recommendation lies in the middle.

A diverse small group — the leader included — should be involved in the key design phases and approval — you don’t want to kick off a session and realize that key people feel blindsided or that the CEO doesn’t agree with the goals or agenda.

Pre-work

Preparing the team is vital without putting too much additional load on their shoulders. Sending out some pre-reads or exercises can help create curiosity.

Usually, we perform a survey to assess the tensions and have some one-on-one interview with diverse team members to get a broad perspective of mindset, moods, and dig deeper into the tensions.

The flow

Most team retreats are very demanding in terms of attention and energy. It’s key to mix activities to manage emotions and depth. For example, after an intense brainstorm, a stoke can relax people. Or a short guided meditation can bring some tranquility after activities that were more challenging or made people feel vulnerable.

Having a clear agenda with planned activities and break is critical, but facilitators must be flexible to adapt to what’s happening at the moment. This means probably spending more time in one section and sacrificing other portions — the outcome is more important than rigidly sticking to the agenda.

To keep the energy flowing, group dynamics must change — switch partners, alternate sitting and standing activities, mix reflection with creative activities or switch the group settings.

Plan small breaks for recovery, decompression, and bio needs. Make room for debriefing the activities — discuss learnings and address tensions.

End on a high note. Review learnings and commitments. Create a celebratory team ritual to wrap up the session in a good mood.

Write a team contract

Improving team performance requires both individual and collective commitments. Signing a team contract is a fun and effective way to carve those in stone. Each person adds two post-its. One with a behavior s/he commits to improving; the other, with one behavior s/he expects the team to provide. Then the entire team signs the contract.

The follow-up is everything

Document the process. Make sure to take lots of photos, capture insights and decisions — assign one person to consolidate everything after the session.

Every offsite must include a concrete action plan with clear responsibilities. Set goals in the one day, one week, one month format (one day being the first day the team is back in the office).

Set up a follow-up meeting (30–60 minutes) to monitor performance and identify tensions — ideally, one week after the offsite.

The facilitator should ensure the team is on track with commitments, keep the momentum going, and address new tensions associated with implementing new practices or habits.

A Team Offsite Allows Experimentation

Build a Safe Space

The whole process should be designed to make people feel comfortable to be themselves and take interpersonal risks. Of course, facilitation is key to create a safe space. But, every step sends a signal.

Transparency and clear communication build trust. Share the purpose and desired outcome ahead of the offsite — if it’s meant to solve a particular issue, make it explicit, don’t sugarcoat the problem.

Make sure to keep pre-interviews or surveys confidential. I strongly recommend the results are shared during the session, in front of the entire team. When management sees the findings first, it creates the impression that results can be filtered or manipulated.

Everyone plays with the same rules

I can’t stress this enough; leaders are part of the team. Thus, part of the problem. Don’t behave like others have an issue, but you don’t. Everyone has to be open to challenge and improve their mindsets and behaviors — leaders included.

I’ve seen many CEOs being an observer rather than an active participant. People are watching — your behavior can encourage or discourage them. Model the behavior you want them to practice. If you expect people to be more candid or creative, start by embracing your own vulnerability first.

Also, set up the room to ensure titles don’t get in the way of honest conversations.

The benefits of external facilitation

Calling out certain behaviors or encouraging people to participate more, for example, become less personal when done by a third party. External facilitation provides a neutral perspective too.

Unfortunately, not everyone in a team is trained in effective facilitation — running a training workshop, and an offsite are two different animals. An employee may bring his/her own biases to the session.

Lastly, external facilitators can share tools and learnings from working with multiple teams across various organizations.

Encourage Participation

Ensuring everyone is listened — especially the voices of quiet people — will increase participation. Senior executives, loud people, and men, in particular, tend to be more outspoken and inhibit or influence other participants’ thoughts.

Clear ground rules, facilitation, and specific methods — like conversation turn-taking — are key to avoid someone from taking over.

What Type of Offsite Is Right for You?

There are different types of team retreats depending on the challenges you are facing. This matrix will help you choose the right one.

“Reflection” versus “Transformation:” The first type is about a deeper understanding of the team’s mindset and behaviors — to reflect on performance and identify growth opportunities. The second type is when a more significant transformation is needed either at a team or organizational level.

“Crisis” versus “Opportunity:” The first is about solving urgent matters to unblock team performance (or even guarantee its survival). The latter is about focusing on strategic conversations and longer-term issues.

1. Team Stabilization:

Think of this as the ER for a team. Toxic behaviors, frictions, and lack of trust are bleeding a team to death. You can’t make any improvements until you stabilize the team first.

A Team Stabilization offsite helps rebuild trust and builds hope.

2. Team Timeout:

A halt in the game can dramatically change the result of a match. Or your business goals for that matter. Taking a timeout is critical for a team to reflect on what’s working (or not), experiment with new ways of working, or even reset their mindset.

A Team Timeout offsite provides a space for reflection and continuous improvement.

3. Team Reboot:

Both Team Stabilization and Team Reboot are perfect when there’s an urgent need to change. The difference is that, in this particular situation, the team is underperforming, but hasn’t reached high levels of toxicity or distrust.

A Team Reboot offsite is like resetting the operating system of your team.

4. Innovation Session:

Its purpose is to focus on designing what’s next. A team gets out of the office to address big-picture issues — removing distractions and short-term mentality is critical.

An Innovation offsite is perfect to generate new ideas and solve current problems or identify new opportunities.

Team Offsite Logistics

Frequency
Teams should have an offsite at least once a year. In our experience, companies that hold them every six or four months, build a better cadence and momentum than those that do it every 12 months.

Duration
For a regular team offsite, one day is usually enough. To address more complex issues or to solve a problem, you might need 2 to 3 days.

Food
Don’t underestimate the value of good food. People are expecting something better than what they get at regular meetings. Also, a team offsite is very demanding. Make sure people are hydrated (water), caffeinated (coffee) and get plenty of sugar (fruits, cookies, chocolate, etc.) throughout the session.

Avoid heavy food and alcohol, so people don’t feel sleepy after the lunch break.

Space
Ideally, it should be outside the building, so it feels different from everyday work. However, you don’t need an exotic location to make the experience successful.

People value being taken out of the familiar — it helps remove distractions to promote higher-level thinking. Flexibility is key to play with the space and adjust it to the different activities and dynamics.

Having a team retreat with intentionality and purpose around growing the organization together has a transformational effect. When people work together — without distractions — to address shared issues and solve them as a team, magic happens.

This article was first featured on Medium


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