Scaling Culture Without Losing Connection: The Old Guard vs. New Guard Tension

Being a great place to work is the difference between being a good company and a great company.
— Brian Kristofek, President and CEO, Upshot

Even the fastest-growing companies can lose their soul, and most leaders don’t see it happening until it’s too late.

We often work with hypergrowth companies, and recently partnered with one that had just doubled its headcount in under a year. On paper, they were thriving: revenue was up, A new CEO had come in with a proven track record of scaling, and the board was excited about the company’s future.

But in our first session, the tension was obvious. The founder, now sitting on the board, still held deep loyalty of the early employees. They shared  history from the early days: late nights in the garage,  scrappy beginnings, the inside jokes that built belonging. The new CEO, meanwhile, brought operational rigor and discipline, but wasn’t part of those formative chapters. The connection just wasn’t there…yet.

Minding the Cultural Gap

The old guard and new guard were looking at the same company through very different lenses. Conversations felt careful. The old guard clung to traditions; the new guard pressed for change. No one was wrong but the divide was real. What began as misalignment started to surface as cultural friction.

There was no single moment where culture broke. Just a growing gap between history and ambition, belonging and scale. Left unchecked, that unminded gap quietly erodes the very culture that made the company worth scaling in the first place.

Why Connection Is the True Growth Engine

Teams that thrive through growth don’t just scale systems, they scale connection.

That doesn’t mean trust falls or pizza Fridays. It means:

  • Ensuring new hires don’t just learn the job, but feel part of the story.

  • Creating rituals where the old guard and new guard can share, align, and build together.

  • Catching misalignment before it calcifies into cliques or silos.

  • Training leaders to model empathy while still driving ambition.

Most companies try to preserve culture by documenting values or hosting all-hands. But culture isn’t what you say,  it’s what people feel every day. If connection isn’t intentionally designed, it quietly disappears.

A team aligned behind a vision will move mountains. It doesn’t matter how smart the strategy is; if people aren’t aligned, execution falls apart.
— Kevin Rose, Entrepreneur & VC

What Happens When You Don’t Scale Culture?

New hires struggle to find their place, so ramp-up slows

  • Teams fracture into “us vs. them”, so collaboration suffers

  • High performers leave because they feel it is not the company, or mission, they joined

  • Leaders make decisions in a vacuum because trust is thin

    We’ve seen this play out across industries (tech, healthcare, construction, finance, and beyond), and found an undeniable theme. Culture begins with strong, well-articulated, shared goals. The growth stories may differ, but the root issue is the same: culture doesn’t scale unless you design for it.

The Groops Take

Scaling culture is the hidden challenge of growth, and one of the most overlooked by leaders.

Most companies focus on systems: org charts, workflows, onboarding processes. But systems don’t hold a company together - the people do. And when growth accelerates, the bonds that made a team strong in the early days can quietly fray.

The best leaders understand that scaling isn’t just about adding headcount, it’s about strengthening connection and alignment. They create rituals that tie the old guard and new guard together, model empathy while driving ambition, and catch misalignment before it calcifies into silos.

Something to Try: Audit Your Old Guard vs. New Guard Dynamic

At Groops, we help leaders make culture scalable by design. Using psychology, coaching, and AI-powered insights, we give teams the tools to stay connected, aligned, and resilient as they grow. Because growth without cohesion isn’t growth, it’s fragility.

Here’s a quick way to spot the divide before it widens:

  • Name it: “Let’s take five minutes to reflect on how our company feels as we grow.”

  • Ask: “Where might the old guard and new guard be experiencing this culture differently?”

  • Listen: Ask yourself, “Are tensions showing up in decision-making, onboarding, or collaboration?”

Close the loop: “What’s one small ritual or practice we can create to keep us united as we scale?”

These conversations surface the invisible divides that growth creates and keeps culture connected as the company evolves.

Ready to Scale Without Losing Connection?

Groops brings experts in team psychology into companies during hyper-growth moments to help teams stay connected, aligned, and resilient as they scale.

If you want to chat about how to grow without losing what makes your culture strong, let’s talk.


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