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5 Mistakes To Avoid When Planning A Leadership Retreat

By June 19, 2019 No Comments

Are you planning a leadership retreat for your team?

If not, it’s time to make it happen.

While there is never a bad time to bring your team together to celebrate wins, troubleshoot challenges and update plans…every organization should plan at least two such events, each year. Typically one at the mid-point of the year (June, July, August) and another at the end/start of the year (December, January, February).

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I facilitate a lot of these events and wanted to share the five most common mistakes leaders make when it comes to creating a great retreat experience for your team.

Here we go…

Mistake #1: Not Having A Leadership Retreat

This is not a nice-to-do, it’s a must-do. 

I understand that you and your team are “really busy,” but that only makes a retreat more essential, not less.

Regular leadership retreats are simply “good hygiene” — a standard operating procedure of any high-performing team.

The retreat environment creates an invaluable opportunity for your team to reconnect, realign and recharge. A mid-year retreat gives you the leverage you need to powerfully, and positively, impact the fortunes of the organization for the rest of the year; leverage that diminishes with every passing day.

Mistake #2: Not Spending Your Retreat Time The Right Way

Done well, a leadership retreat should take at least one full day, and as many as two or three days.

If you’re wondering “what the heck are we going to do with all that time?” here a simple structure that works:

1. Strategy Review + Planning (60% of your time)

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This includes all activity related to working on the business (e.g. review performance, discuss new opportunities and challenges, set targets and allocate resources for the rest of the year).

2. Relationship Building (30% of your time)

A good retreat will not only lead to better business outcomes, it should lead to better business relationships, too. At a minimum make sure the team is able to spend time around the table, sharing a meal. Even better, incorporate shared learning, adventure or fitness into the agenda. It doesn’t matter how long your team has been working together, don’t overlook the importance of reinforcing and strengthening existing relationships.

3. Personal Review + Reflection (10% of your time)

The most commonly overlooked element of a great team retreat is personal time. When creating your agenda make sure that you factor in some “unscheduled” time for each individual to do his or her own reflection and planning.

Mistake #3: Only Talking About Your Problems

During the team strategy review and planning, it’s easy (and instinctive) to start with the problems that need to be solved.

The most creative, innovative teams however take a different approach: they start by acknowledging and celebrating the highlights and key accomplishments of the year, so far.

Not only does set a positive and enthusiastic tone for the entire retreat, but it often leads to more profound insights, as well.


Want help designing a powerful leadership retreat? 


The research of social psychologist Barbara Frederickson has shown that starting a meeting with “good” news (i.e. highlights, key accomplishments, customer success stories, etc.) can lead to more creativity, innovation and good ideas for the rest of the session.

Mistake #4: Only Talking About Your Goals

When planning a retreat, it’s tempting to try to get quickly to the “action-items.”

We want to drill down on two specific questions:

  1. What are our goals?
  2. What do we have to do to hit them?

It would seem that answering these two questions is why you went on retreat in the first place, right?

Well, sort of.

For better or worse, before you can thoughtfully answer the question “what are our goals?” you and your leadership team need to revisit two, more foundational questions:

  1. What are our Core Values?
  2. What is our Vision?

Your company Core Values and “Vision” are essential inputs in any thoughtful strategic plan. Your “Core Values” create a healthy constraint on your strategy (see image below) — you can pursue any opportunity or path as long as it is consistent with your values.

Your “Vision” is the 3-5 year view of the company, team and/or outcomes that you are trying to create.

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That said, Core Values and Vision can and do evolve over time.

Every time you hire a new employee, launch a new product or acquire a new company, your create an opportunity for change. That’s why it’s essential to revisit these ideas during your retreat.

A few important questions to ask your team…

On Values:

  • How, if at all, have our values changed over the last 3, 6, 12…months?
  • Are there values that we have grown out of?
  • Are there new values that we need to adopt, going forward?

On Vision:

  • Where do we want to be, as a team, in 3-5 years time?
  • How big do we want to be?
  • How fast do we want to grow?
  • Whom do we want to serve?
  • What trade-offs are we willing to accept?

Only with answers to these questions can you, as a team, confidently decide “what are we going to do?”

Mistake #5: Not Using A Professional Facilitator

Many leaders think: “I’ll just lead this myself.”

Don’t do that.

A trained, professional facilitator can help you 10X the value created through this retreat by, among other things:

  • Creating a strong, structured agenda for the day.
  • Teeing up the retreat with thoughtful prep work for the team.
  • Keeping conversations moving forward (as opposed to spinning in circles).
  • Serving as a discussion “referee;” highlighting where assumptions are being made, biases shared, and/or where more data (or discussion) is needed.
  • Making sure everyone in the room is heard.
  • Allowing you (the leader) to focus your energy entirely on the strategic conversation taking place, as opposed to worrying about lunch, breaks, agendas, etc.
  • Synthesizing the day and helping to create an action plan that ensures that the decisions you make get implemented.

Some leaders worry that the facilitator won’t “know our business.” That’s OK. They don’t have to.

The role of the retreat facilitator is not to teach you about your business, or tell you what to do but, instead, to ask the questions you need to be asked in order to discover the path forward for yourself

Getting Started: Three First Steps

Carve out 45 minutes, this week, to start planning your retreat. The first three steps are easy:

  1. Pick a date.
  2. Pick a location.
  3. Find a facilitator.

Good luck, have fun, and make it happen.


Want some help in developing a powerful leadership retreat? 

Ben Sands

Author Ben Sands

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