Free Training: Leadership Secrets of 'Top 1%' CEOs


with Ben Sands


with Ben Sands

A world-class facilitator and coach that I recommend without reservation.

- Stuart Breslow

Global Chief Compliance Officer, Morgan Stanley

blog image

5 Mistakes To Avoid When Planning A Leadership Retreat

August 08, 20235 min read

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).

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

Here we go.

Mistake #One: Not Having A Leadership Retreat

A leadership retreat 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 organization's fortunes for the rest of the year, leverage that diminishes with every passing day.

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

A good 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 is a simple structure that works:

1. Strategy Review + Planning (60% Of Your Time)
Strategy review and planning includes all activities related to working on the business (e.g., reviewing performance, discussing new opportunities and challenges, setting targets, and allocating 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, ensure the team can spend time around the table, sharing a meal. 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, ensure you factor in some "unscheduled" time for personal 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 organization's most pressing problems.

However, the most creative, innovative teams take a different approach: they start by acknowledging and celebrating the highlights, key accomplishments, and lessons learned since the last retreat.

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

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 What You're Going To Do

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's 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.

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

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

Only with clarity around your Values and your Vision can you, as a team, confidently decide, "What are we going to do going forward?"

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  0X 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 the assumptions, biases, limiting beliefs, and/or where more data (or discussion) is needed.

  • Ensuring everyone in the room contributes, as appropriate, to the discussion and that all perspectives are accounted for.

  • 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 create an action plan that the next steps are crystal clear.  

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 create the environment, and ask the questions, that can move your thinking forward.

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 With Your Next Retreat?

We love facilitating high-energy, high-impact, team retreats. 

Click here to schedule time to speak with us about what you are looking to do. 

Even if we don't decide to collaborate, we'll happily help you brainstorm how to create a great event.

Back to Blog



Ben Sands is an executive coach and founder of Sands Leadership.

Ben Sands is the perfect mix of coach and consultant and he has been coaching me to higher levels of clarity and meaning for almost 10 years! In leadership and life, we all have a lot of big decisions to make and Ben has taught me is how to make those big decisions confidently, and in a values-aligned way. His coaching is an investment that has paid off exponentially.

Alex Budak

Professional Faculty,

UC Berkeley Haas School of Business & Author,

Becoming A Changemaker