Slow Down to Speed Up: You Can’t Afford to Skip the Offsite
At Wisdom Partners, we’ve worked with dozens of founders navigating this tension. And one of the most powerful tools we’ve seen for restoring clarity and connection is an offsite intensive.
You know the feeling: your team is technically functioning, Slack is buzzing, projects are moving… but something’s off. Miscommunications pile up. Progress feels slower than it should. Everyone's working hard, but not necessarily in the same direction.
It’s not dysfunction; it’s disconnection. And for fast-moving startups, especially remote-first ones, it’s one of the biggest momentum killers.
At Wisdom Partners, we’ve worked with dozens of founders navigating this tension. And one of the most powerful tools we’ve seen for restoring clarity and connection is an offsite intensive.
This blog is drawn from a candid conversation between Josh Broward and the leadership team at Mark My Words Media (MMWM), which includes David Dripps and Wisdom Partners co-founder Charles Jolley. They didn’t set out to become offsite evangelists, but after running a series of retreats with us, that’s exactly what they’ve become.
Why Offsite Intensives Work (When Done Right)
David Dripps, MMWM’s CEO, admitted he was skeptical at first. Coming from corporate America, he’d been to plenty of offsites, usually well-produced but forgettable affairs where 80 people watched slides in a hotel ballroom.
That’s not what we do.
When MMWM ran their first offsite with us, David and Charles had just acquired the business. Six months in, they understood the basics: who did what, what worked, where the pressure points were. But they didn’t realize how many assumptions needed resetting.
That retreat changed the game.
David shared, “The collaboration, output, and quality of conversations were dramatically better after that retreat – especially among the people who spent that time together in person.”
The Magic Isn’t the Mountains; It’s the Format
Our offsites aren’t corporate getaways. They’re highly planned intensives designed for companies that need clarity, fast.
We help teams surface how they see their work and themselves. Then, we help them walk through misalignments and rebuild a shared perspective in real time. It’s efficient, clarifying, and surprisingly energizing.
People don’t just hear the vision; they see themselves in it. When teams reflect on what they’re building and how they contribute, that’s how a sense of deep ownership happens.
As Charles Jolley put it: “Founders often say, ‘Why can’t my team just think like me?’ But alignment doesn’t come from telling people what to think, it comes from hearing what they think, and building from there.” Our retreats help the key team members put forward their thoughts on critical issues, and then the whole team refines their understanding and planning in real time. It’s game changing because the team gets real about problems, solutions, and core assumptions.
The Real ROI? Months of Progress in a Week
We’ve heard the objections: Offsites are expensive. You don’t have time. It feels indulgent.
But here’s the truth we’ve seen again and again: a well-run offsite is the single most efficient tool for alignment and acceleration.
It compresses what would take months of 1:1s, Zoom calls, and Slack threads into a few days of shared understanding and renewed energy. Teams return clearer, faster, and more accountable.
Charles put it bluntly:
“One week can save you months of trying to align people remotely. In some cases, we couldn’t even get out of the starting gate until we did it.”
Not All Offsites Are Created Equal
We’ve mostly stopped calling these “retreats.” This isn’t a group vacation at a spa. This is getting your core team away from normal distractions to do deep, hard work on how you operate as a company, where you’re going next, and how you’re going to get there.
We have a road-tested format that works because we’ve lived it, both as founders ourselves and alongside the teams we guide. Here’s what makes our offsites effective:
Pre-work that drives clarity, not complexity
Live, facilitated discussion where teams actually think and solve together
Behavioral tools that build understanding, not personality quizzes that collect dust
Space for connection, because shared meals do more than shared docs
Flexible agendas that let real issues rise and get addressed
And they’re not just for early-stage chaos. These experiences help even mature leadership teams sharpen their focus, align on growth, and re-commit to the mission together.
So, Founder to Founder…
If your company’s moving, but your gears aren’t fully aligned …
If your people are good, but not fully bought in …
If you’re stuck translating vision over Zoom …
If you’ve all been grinding hard, but you’re not sure you working on the best things …
It’s time to step away. To reconnect. To refocus. To reset.
At Wisdom Partners, we run offsites for founders and leadership teams who are ready to think harder, lead with more clarity, and build healthier companies. It’s not a break. It’s a lever.
Let’s get your team in the room.
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