Why Most Corporate Retreats Suck—And How to Fix Them
This essay is autogenerated from my x.com threads.
Why Most Corporate Retreats Suck—And How to Fix Them
Most corporate retreats are a waste of time. Just saying the phrase "corporate retreat" makes my skin crawl. It conjures images of forced fun, empty speeches, and a general sense that this is an expensive exercise in checking a box.
I’ve never heard a friend say, “Wow, that corporate retreat was amazing.”
And that’s a shame because when done right, these events can be incredibly impactful.
We recently hosted one of our Boom & Bucket Sales Kickoff Retreats, designed specifically for our remote sales team. But here’s the key difference:
This was not a generic corporate event.
This was not an awards ceremony to pat upper management on the back.
That kind of retreat is a slap in the face to employees. They don’t need a few days of performative hype. They need something that directly helps them do their jobs better.
The Real Problem: Remote Work is Harder Than We Admit
The challenge we were solving for is simple but critical: human psychology makes remote work difficult.
When you’re not in an office, you don’t get daily reminders of the company’s vision.
It’s easier to blame coworkers when you don’t see them in person.
There’s no natural outlet for venting or camaraderie.
Over time, this can lead to isolation, misalignment, and tension. And ultimately, that tension turns into attrition—great employees quit.
The Fix: 3 Goals for a Sales Kickoff
Our Sales Kickoff Retreat was designed to accomplish three specific things:
Reduce the distance between our sales and support teams—both literally and metaphorically.
Release any built-up tension from miscommunications, missed expectations, or just the natural friction of remote work.
Refuel our team’s energy, inspire them, and remind them why they joined us in the first place.
You can’t put these outcomes into a spreadsheet. You can’t A/B test them with a control group. But when a retreat works, you feel it.
At the end of our two-day event, the energy in the room had shifted. People were refueled, excited, and ready to win.
If your corporate retreat doesn’t deliver that feeling, you’re doing it wrong.
Want to iterate on this further? Let me know!