If you lead retreats long enough, eventually you learn a very important lesson: You cannot make everyone happy. And more importantly, you shouldn’t try.

That can be a hard thing for retreat leaders to accept because most of us genuinely care about the people we serve.

We want everyone to love the retreat. We want them to love the venue, the food, the activities, the schedule, the teaching, the excursions, and probably us too. So when someone isn’t happy, it can feel deeply uncomfortable.

• Maybe one participant wants more free time while another thinks there isn’t enough scheduled.
• One person wants deeper conversations while someone else feels things are getting too emotional.
• Someone loves the healthy menu while another wonders why there isn’t more comfort food.
• One participant wants to stay up talking until midnight while another wants the group quiet by 9 PM.

…and suddenly you find yourself trying to make adjustments so everybody gets what they want! That sounds like excellent customer service. But sometimes it’s actually people-pleasing.

Leadership is different from people-pleasing.

There is an important difference between listening to your participants and allowing every individual preference to determine how you lead.

Excellent leaders listen. They pay attention. They make thoughtful adjustments when something genuinely needs changing. But they also remember that they are responsible for the entire group experience, not the happiness of every individual person in every individual moment.

That distinction is huge. Because sometimes what one person wants would negatively affect everyone else.

• If one participant continually needs additional attention, giving it to them may mean the rest of the group gets less of you.
• If someone wants you to change an activity because it makes them uncomfortable, you need to decide whether the activity is actually inappropriate… or whether being stretched a little is part of why they came.
• If someone wants an exception to a policy, you have to consider what that exception means for everyone else who agreed to the same terms.

Good leadership isn’t simply asking: “How do I make this person happy?” It’s asking, “What serves this person, the group, and the purpose of the retreat?” Those are very different questions.

You see, sometimes discomfort is part of the experience.

This is particularly important when we lead transformational retreats. People don’t always come to retreats simply to be comfortable.

They come because something in their life needs to shift. And change can be uncomfortable.

• A meaningful conversation can be uncomfortable.
• Meeting new people can be uncomfortable.
• Being asked to look honestly at yourself can be uncomfortable.
• Putting your phone away can be uncomfortable.
• Sitting in silence can be uncomfortable.
• Trying something you’ve never done before can be uncomfortable.

Our job isn’t necessarily to remove every uncomfortable moment. Our job is to create a safe, well-held environment in which people can experience those moments without feeling abandoned, pressured, or unsafe. There’s a big difference.

Of course, sometimes the participant is right. Not every complaint is people-pleasing territory. Sometimes someone points out something we genuinely missed.

For example, maybe the schedule was too packed, or dietary needs weren’t handled properly, or an activity didn’t land the way we thought it would, or someone didn’t feel included, or perhaps… our communication wasn’t clear.

Being a strong leader doesn’t mean becoming defensive and saying, “Well, you can’t please everyone.” Quite the opposite.

Good leaders are willing to listen without automatically assuming they did something wrong.

We can ask: Is there something useful for me to learn here? Sometimes the answer will be yes. And sometimes the answer will be no. This person simply wants something different from what I’m offering. And that’s okay too.

One unhappy person does not mean you failed. This may be one of the hardest lessons for caring retreat leaders. You can have fifteen people who are thrilled with the experience and one person who is unhappy and guess which person you’ll think about when you go to bed? The unhappy one.

We humans are funny that way. But one person’s disappointment doesn’t erase the experience of everyone else. And it doesn’t necessarily mean you need to change what you’re doing.

• Sometimes a person wasn’t the right fit for the retreat.
• Sometimes their expectations were different from what was clearly communicated.
• Sometimes they’re going through something that has very little to do with you.
• And yes, sometimes we simply cannot give someone exactly what they want.

That doesn’t make us bad leaders. It makes us human. Your job is to lead the room. When I’m leading a retreat, I try to remember that my responsibility is NOT to keep everyone happy every minute.

My responsibility is to create a thoughtful, safe, meaningful experience and then lead it with integrity. That means listening. It means being flexible when flexibility serves the group. It means admitting when I’ve missed something. It means changing course when necessary.

But it also means being willing to say: “I hear you, and we’re going to continue with the plan.” Or, “I understand this isn’t what you would prefer, but this is what serves the group right now.” You can say those things with kindness. And you can say them without making anyone wrong.

Because here’s the deal…

Leadership isn’t about winning a popularity contest… it’s about creating a container where people feel seen, heard, held and where the purpose of the retreat remains bigger than any one person’s preferences.

Take a moment to share your feelings below – I’d love to know!

xo Sheri