Themes for Leadership Retreats

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What do you talk about at a leadership retreat? At leadership retreats, it’s important to use the time in the best manner such that you can create a stronger connection within the leadership team and that you’re strengthening your vision, mission and strategy.

When you get prepared to talk about all of this at your leadership retreat, there’s a chance something else is going to get in the way. After facilitating leadership retreats for 20 years, I’ve seen it, and experienced it time and time again.

Just like in this video when I was creating this video and got kicked out in the lobby of the Omni San Diego Hotel. I got kicked out exactly when I was talking about what I care about. We didn’t set this thing up. This is kind of the way life goes, doesn’t it? 

 If you have the guts to do the deep dive to figure out what you care about, there’s always something that comes up. 

  • I have to take care of my kids.
  • Gotta put food on the table. 
  • I need to call my mom.
  • Gotta take care of the dog. 

Well, for us, and on this day, what came up was being kicked out of the lobby the Omni Hotel. 

We immediately decided to finish the video of what I care about in the room that I would be leading a two-day leadership retreat with a Fortune 500 Company.

It takes a lot of guts to determine what you care about, and as I was being kicked out of the lobby, I declared that I care about leadership development. I care about leadership development at the highest level, so much so, that I was okay with working for 17 years to really live my dream. My dream has been to work with the leaders of a global Fortune 500 company (much like the one I got fired from) to transform who they are as executives and as human beings. So, what I have learned over 17 years is the way to transform a leader is to get them emotionally, intellectually, and spiritually in touch with what they care about

Questions To Ask at a Leadership Retreat

When I am hosting a leadership retreat, I go with the deep question that causes a leader to challenge whether he or she is living his or her care and purpose as a leader and a contributing member of the team. Team cohesiveness has everything to do with being deeply connected to the purpose of your team and your own purpose as a leader.

Just as Jennifer Porter mentioned in her recent HBR Article, effective teams have to go slow to go fast by investing time and energy into the critical skills of reflection and commitment that we focus on at our leadership retreats. She explains the odds of improving teams in a meaningful and sustainable way are strengthened if every team member – including the – leader learns to master internal & external self-awareness and personal accountability.

In the leadership retreats I facilitate, I cover all of these with three simple, yet complex questions. 

What do you care about?

Do you own it?

What is stopping you?

Let’s look into how these question help build self-awareness and accountability.

What do you care about? 

Skill: Internal Self-awareness

When was the last time someone asked you that question?

The answer is probably, never.

How often do you have the conversations around your care for family, connectedness, purpose, making a difference, living a meaningful life, or impacting your community?

For leaders and teams, this should be at the core of the conversations. Leaders must understand what they care about and wake up every day and own what they care about. 

If I woke up every day and didn’t focus on what I cared about, what kind of leader would that make me? 

In today’s fast-paced society, we all run around being so busy, that we seem to lose touch with what we really care about. When leaders and teams take the time to really dig deep and get connected to the things that they care about, they build an incredible foundation to their journey of self-awareness and team-connectedness. 

Do you own it? 

Skill: Personal Accountability

Many people have never been asked what they care about, and even fewer have been asked, “Do you own it?” This question normally stops most leaders in their tracks as they take a long, hard look at their life and ask themselves that question.

“Do you own it?” asks whether you put your care or your purpose at the center of your life.  Leaders ask themselves, are they here to make a paycheck, or are they here to make a difference?  Do they wake up everyday with their purpose in mind, and do they take that into every conversation that they have…with their direct reports, with their family, with a stranger?

What is stopping you?

Skill: Purposeful Living

After being asked the previous questions, it leads us straight into the next question, “what is stopping you from taking care of what you care about?” This question exposes the barriers that we put in place that hold us from putting our cares front and center in our lives.

Your ability to lead comes down to your ability to identify what you prioritize over the things you care most about.  Seems ironic that we “prioritize” so many things over those things we ‘care’ about. A Leadership Retreat, in order to be successful, must have all the leaders in the room handle the things that are getting in the way of the leaders’ true priorities.

Followers can only commit to a Leader who is leading from his or her purpose and care.  It is only through the realignment at a Retreat that a Leader can go back to the business at hand, and have others commit to the future that the Leader is there to create with the team.

Bonus Question: What is relevant to you? 

I want to share with you another story, and this is probably the most profound. It’s definitely the most profound event that happened to me this year, if not the last 10 years. 

Some of you know I volunteer and help teenagers develop entrepreneurial skills. Last night, the teenagers were assigned to go out and design a new business: a news outlet focused on teenagers. Their task was to “create a news outlet that is relevant to teenagers, like you.”

We jumped into research. I jumped in too.  We looked at what news outlets are out there, what applications teenagers were consuming, what exactly are teenagers consuming.  Their conclusion, “We must create a news outlet with short fun videos.”

But what we never did, and I’m to blame (and I’m the leadership guy,) was say, “you know what, let’s just stop. Stop the research. Stop the work. Let’s ask the big question, “what is relevant to you? As a teenager, what do you care about?  What is important to you? What concerns you and what is NOT being talked about?”

We had a guest come in from Shaar HaNegev, a city on the Israeli-Gaza border, and he woke these kids up. He had been a principal for 30 years, and he was not buying what the teenagers were selling.  

He asked the question, “What is relevant to you?” & “What is important to you?”

The kids didn’t have any answers.

Just by asking these questions, he changed the mood. Then, feeling like he had landed on a major problem, the problem that all people have, which is avoiding the biggest questions, he asked, “What is love?” And at that point, you could have heard a pin drop, which was odd for a bunch of teenagers who were usually pretty noisy. They couldn’t answer the question. The kids couldn’t answer the question, “What is love?” It was clear they were making excuses. Their responses were, 

“I’m too young.” 

“I haven’t experienced it.”

“We don’t have answers for that question.”

They couldn’t answer the question, “What is relevant for you?” & “What is important to you?? “

And these questions aren’t just difficult for 17 years old.  From my experiences, they are difficult for 27-year-olds, and 37-year-olds, and 47-year-olds. At Leadership Retreats, we talk about these questions because the answers lie in the core of your leadership team. When teams don’t talk about what they care about, they miss crucial connections that can help them become a truly high-performing team.

Leadership Retreats are for having deep conversations.

Leadership retreats are to identify:

“What do you care about?”

“Do you own what you care about?”

“What is stopping you?”

“What must you do to completely live as a leader embodying that which you care about most?”

Followers follow Leaders who live their lives in integrity.  Leadership retreats are to help leaders continually check their own integrity and to develop together as a team. Just like Stan Slap says, “You can’t sell it outside if you can’t sell it inside.

Leadership Retreats are about going inside so when you go outside to lead your team, you lead from a place of purpose, power, and commitment.”


  • the way to transform who you are is to get in touch with what you really care about
  • If you have the guts to even do the deep dive to figure out what you care about theres always something that comes upWhat-to-talk-about-at-a-leadership-retreat-san-diego-3-2
  • what do you care about? Do you own it? What is stopping you today? What-to-talk-about-at-a-leadership-retreat-san-diego


Porter, J. (2019, January 29). To Improve Your Team, First Work on Yourself. Retrieved from

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