Over the past couple of weeks, after I posted pictures from our leadership retreat in Hawaii, I have been asked the same question more than a few times.
Why do you do a manager retreat?
It is a fair question, especially when the pictures include sunsets, the PayNW Olympics, and a baby goat that was four days old.
But here is the thing. The fun parts are not actually the point.
This year marked our tenth manager retreat. We have been doing them for eleven years now. We skipped one year during COVID and even held a virtual retreat when that was the only option, because the retreat was never really about the destination. It was about the time together.
And we started doing them long before PayNW became the organization it is today.
Our first retreat was in 2016. There were five or six of us. Everyone took the same ferry from Seattle to Victoria, Canada, and we spent two days together talking about the business.
Not working in it, but talking about it.
That distinction matters more than people realize.
Most leadership teams spend their days focused on the trees: customer issues, team conflicts, deadlines, and the never-ending to-do list. All important. All necessary.
But when every day is spent dealing with the next tree in front of you, you rarely get the chance to step back and see the forest.
That is what a retreat creates. Two days where the leadership team steps out of the day-to-day operations and into conversations about the bigger picture: how the business performed over the last year, where we are going next, what is working, and what needs to change.
And maybe most importantly, making sure the leadership team is aligned.
We do not talk about this enough, but leadership teams only work when the leaders see themselves as a team first.
One of the principles that matters most to me is that our leaders are on the leadership team first and their department second. That might sound simple, but in a service organization it can get complicated quickly.
The tax team has frustrations with service. Service has frustrations with implementation. Implementation has frustrations with tax. Everyone is usually convinced their problem is the most urgent one.
That dynamic is natural. But if leaders only interact when something goes wrong, those relationships can become transactional very quickly.
A retreat changes that.
When leaders spend time together outside the pressure of day-to-day operations, they begin to see each other differently. The tax manager is no longer just the person who escalates issues. They are the person you stayed up too late laughing with during game night.
So when the next issue pops up, the conversation starts in a very different place. Less defensive. More collaborative.
Now, if you follow me on LinkedIn, you have probably seen some of the more entertaining parts of our retreats.
There was the goat dairy in Maui where we got to hold baby goats, including one that was only four days old. Another year we did a bike and food tour through Portland. One year Brittany and I built an escape-room style challenge for the group.
And every year we end the retreat with a game night. Wavelength has become a bit of a tradition.
Those moments are not filler. Shared experiences build relationships faster than conference room meetings ever will.
I also like to include moments that encourage a little bit of self-reflection. One year we went to Barnes and Noble and everyone had to buy two books, one for themselves and one for someone else whose name they drew.
Another year I handed everyone $100 cash and told them to go buy something for themselves.
That turned out to be more interesting than I expected. Two leaders looked at me and said, “I never spend money on myself. What am I supposed to buy?”
That moment stuck with me, because leaders spend so much time taking care of their teams, their clients, and their families that they rarely pause to think about themselves. Sometimes a retreat simply gives them permission to do that.
And if I am being honest, there is another reason I love doing these retreats.
It is my chance to say thank you.
I once described the retreat on LinkedIn as a love letter to my leadership team, and the more I thought about it, the more I realized that is exactly what it is.
Most of our leaders are parents, and many of them do not get the opportunity to step away for a few days very often. Every year someone tells me they slept through the night for the first time in years, or that they forgot what it felt like to slow down for a minute.
That alone makes the retreat worth it.
This year we did something new.
For the first time, we invited spouses and significant others. Honestly, I thought it would simply be fun. What I did not expect was how meaningful it would be.
We included them in a welcome dinner, some of the lunches, and they came to watch the PayNW Olympics. What surprised me most was how quickly the spouses connected with each other. They spent time together while we were working and apparently even started a group chat.
Which I suspect occasionally includes messages like, “Why is my spouse still working?”
But it also creates something bigger: a support system and a deeper understanding of what this work looks like on both sides. Our leaders do not do this work alone. Their families are part of the journey too.
Now, I will be honest. Hawaii was expensive.
We went because the team had an incredible year. We had only 2.8 percent controllable attrition and we beat our sales goals. The team worked incredibly hard, and it felt like the right moment to celebrate that.
On the last day of the retreat, one of our leaders said something that stuck with me. She said she appreciated the trip, of course, but what she appreciated even more was that it made her more motivated than ever to produce results that might earn another one.
I did not plan the retreat as a carrot.
But if we have another year where we absolutely knock it out of the park, why not celebrate that together?
Because great leadership teams do not happen by accident. They happen when you invest in alignment, in relationships, in reflection, and yes, in a little bit of fun along the way.
Sometimes that investment looks like two days away from the day-to-day so the team can finally step back and see the forest instead of just the trees.
And occasionally…
It looks like holding a baby goat in Maui.
And honestly, I cannot recommend that leadership strategy enough.
Gratefully,