One of the hardest parts of reinventing an agency has nothing to do with strategy.

You can figure out the new positioning, decide which services to stop selling, identify the clients you want to work with, and put together an ambitious three-year vision. Then you look at your team and realize the people who helped you build the agency you have today may not be the same people you need to build what comes next.

This is where a lot of agency reinventions stall, and we understand why. You may have people who have been with you for five, eight, even ten years. You've gone through difficult clients, lost pitches, payroll scares, and countless changes together. When you decide to reinvent the business, the natural instinct is to assume you'll figure out the next version together.

Sometimes you will. But avoiding the possibility that the team may need to change can keep the entire business stuck in its previous chapter.

The Ship of Theseus, Agency Edition

There's an old thought experiment called the Ship of Theseus. A ship leaves port and, over the course of its journey, its wooden planks are replaced one by one. Eventually, every original plank has been replaced.

When the ship arrives at its destination, is it still the same ship?

We've found this to be a useful way to think about agencies. An agency's identity isn't stored in any single employee, or even in the founder. It's in the standards you've built, the reputation you've earned, the way you approach problems, and the kind of work clients know you for. The people, roles, and organizational structure are the planks. Those can change without erasing the identity of the agency.

Every team is built in response to a particular version of the business. The people you hired at $1 million in revenue were hired to solve the problems of a $1 million agency. The leadership team that worked when you had 20 employees may not be the leadership team you need at 50. The business changes, and sometimes the role changes faster than the person sitting in it.

Why This Is So Hard

Most founders can see when something isn't working. The harder part is acting on it, particularly when the problem involves people who have been part of the company for years.

Team changes are slow, disruptive, and emotionally expensive. Meanwhile, the agency keeps running. Clients still need work delivered, payroll still needs to go out, and new business still needs to close. There's no pause button where you can redesign the organization and start again. You're rebuilding the ship while it's at sea.

There's also loyalty. Keeping someone who has been with you for years can feel like what a good leader should do. We've wrestled with this ourselves. But if the business has outgrown someone's role and you know there isn't a place for them in the organization you're building, keeping them indefinitely isn't necessarily loyalty. Often, you're simply delaying a decision, and usually they can feel it too.

The rest of the organization feels it as well. If you're talking about building a more ambitious agency while continuing to organize the business around yesterday's needs, people notice the disconnect.

Reinvention Also Means Bringing New People In

This conversation isn't only about determining who no longer fits. You also need to ask who you're missing.

If you're serious about building a substantially better agency over the next three years, there's a good chance some of the people you need aren't currently inside the company. This is where senior external hires can make an enormous difference.

They're expensive and can make the P&L uncomfortable in the short term. But the right senior hire changes more than their individual function. They bring experience your organization doesn't have, question things your existing team may have stopped questioning, and introduce a different sense of what's possible.

Promoting from within is important, and we've done plenty of it, but internal promotions and external hires do different things. One compounds institutional knowledge. The other introduces new knowledge. Healthy organizations need both.

Sometimes the Founder Is One of the Planks

We experienced this ourselves at Barrel.

A few years ago, we handed the CEO role to Lucas after running Barrel for roughly 18 years. If you want to extend the Ship of Theseus analogy, we were some pretty old planks.

Stepping out gave Lucas room to reshape the organization in ways that would have been difficult with us continuing to run the company day-to-day. He brought different energy, ideas, and ways of operating. Watching Barrel evolve under his leadership reinforced something we believe much more strongly now: sometimes the company needs fresh perspective more than it needs continuity.

That doesn't always mean someone has to leave. A founder can move out of the CEO role. A longtime leader can take on a different responsibility. Someone struggling in one part of the organization might thrive somewhere else. The point is being willing to question the current configuration, including your own place in it.

Build the Team for Where You're Going

If you're thinking about reinventing your agency, temporarily forget your current org chart and start with the business you're trying to build.

Write down what your best-fit clients will need from you three years from now. What capabilities will you need? What level of talent will they expect? What will technology change about how you deliver the work? What will clients expect from you that you simply can't do today?

Then look at your current team and ask: Who can grow into what we'll need? Who is better suited to the version of the agency we have today? What capabilities are completely missing?

The goal isn't to replace people for the sake of replacing people. When someone does need to leave, they deserve clarity, respect, meaningful severance when possible, and recognition for what they helped build.

The goal is to make sure your talent strategy matches your business strategy. If the agency you're trying to build looks meaningfully different three years from now, it shouldn't be surprising if the team does too.

That's not a failure of the old team. It's part of building the next version of the company.

The ship can remain yours even when the planks change.