The Quiet Cost Of Keeping Loyal People Too Long
Growth happens slowly, then moves like a bullet train.
As it accelerates, the team that got you here may struggle to keep up. Momentum often outpaces the skills that first set it in motion.
The team that gets you to $1M, likely won’t get you to $20M. And when you get to $20M, that team won’t get you to $50M.
The strategies and mindset your team uses to get to $1M are significantly different from what your business needs to mature to $20M.
When momentum picks up, clinging to the way you’ve “always done it” becomes deadly.
It’s easy to spot the people on the team who are not performing.
It’s hard to spot the people who aren’t scaling with your business when they are also your dedicated, day-one team members.
Most founders have an incredibly difficult time with this transition.
I sure did.
I had a founding team member who I absolutely adored, and had been with us through it all. We had just reached a new stage of growth in revenue, product, and market saturation. It was everything we had worked so hard for.
Things were moving fast. We needed a lot more discipline in how our team worked.
We also needed specialists who could come in to lead without me telling them how to lead.
But this founding team member fought the momentum of these changes.
They pushed back on the new ways we needed to work, often complaining loudly to others about how much changed, reminiscing about the old ways of doing things. They became resentful, eventually disrupting the overall team and business.
I was confused.
We were supposed to change - that was clearly the goal. What I didn’t realize was that some people wouldn't want that change once it had arrived.
I mistakenly internalized their struggle, believing it was my job to fix it.
I tried changing how we worked so it fit them, and then I moved them to different roles (multiple ones). Nothing worked.
While the rest of the team moved forward, they lagged behind.
Unfortunately, no founder escapes this reality: Eventually, your business will outgrow your team.
Ignoring this is one of the biggest killers of scale - and team morale.
The toughest challenges you’ll face as CEO are often related to people. Not product. Not sales. People.
While uncomfortable, here’s a truth most CEOs need to hear: Keeping people around just because you like them is destructive.
It’s insulting to the person. It’s toxic for the business. It kills team morale.
People in your business need to add value - even the most dedicated ones who have been with you from the very beginning.
Today I’m diving into a topic that isn’t talked about much:
How do you navigate when your most dedicated team members won’t scale with your business?
Let’s dive in.
5 Ways To Navigate When Your Business Has Outgrown Your Team
I’ve had over a decade of experience building big businesses. Over the years, I have relied on these five simple tactics to help me navigate when my business has outgrown my team.
Awareness Over Delusion
It's tough to spot when a beloved team member starts working against your company's growth. We get attached. We ignore the signs. We don’t see clearly.
But scaling a business requires seeing things as they are, not as we wish them to be.
Having concrete indicators helps us cut through delusion and assess our team’s evolution with awareness.
Look out for these indicators:
Resistance to new processes or tech
Difficulty delegating or letting go of tasks they’ve always handled
Push back against new hires. I’ve seen new people brought on for the next stage get a ton of pushback from folks who don’t want things to change. For example, an older team member might find fault with a new product design specialist who is trying to implement more documentation and tracking to keep things moving fast.
Struggle with strategic thinking beyond day-to-day operations
Opposition to implementing systems to move faster with less chaos
Nostalgia for "the good old days" of the company
Assess Energy and Impact, Not Just Performance
It’s crucial to differentiate between temporary low energy due to circumstances and persistent energy-draining behavior.
I turn to a simple spreadsheet to assess my team’s energy and impact on a weekly basis.
This weekly assessment helps me spot patterns and identify trends. If I see a pattern, it's time to dig in. Sometimes I might need to get more info from other team members before making a decision. Sometimes I have enough info to know that I will need to have a tough conversation.
Feel free to steal my template here as a starting point for your own.
Have Tough Conversations Early and Quickly
I can’t stress enough how draining it is to carry around unresolved problems. It kills your focus. It steals your headspace.
Avoiding tough conversations always makes things worse.
Instead, learn to get good at having tough conversations. One of the most generous things you can do is to tell someone when you observe they aren’t succeeding in their role.
In the past, I’ve found it difficult to face when a dedicated team member couldn’t scale with us. But I realized that any excuses I made for them only harmed the rest of the team. And in the end, the longer I took to make a decision I already knew needed to happen, the more our relationship suffered.
Your job as a CEO is to build a team that evolves with your vision.
It’s also your job to help people leave with grace when it’s in everyone’s best interest.
So, face the tough conversation early - and quickly.
You’ll earn your team’s respect, and end the internal battle that's been draining your energy.
Normalize Personal Growth, Even When It Means Goodbye
Letting someone go doesn’t have to be a failure on either side.
The most powerful thing you can do as a CEO is create an environment where personal growth trumps business needs. This means actively encouraging your team to evolve, even if that evolution leads them away from your company.
When handled well, parting ways can be an opportunity for growth on both sides.
What this looks like in practice:
1. Open Dialogue About Growth
Regular career development conversations that go beyond company roles
Honest discussions about skill gaps and aspirations
Support for external learning opportunities, even if they don't directly benefit your business
2. Celebrate Departures as Wins
Share stories of team members who've successfully transitioned to better-fitting roles elsewhere
Maintain relationships with alumni who've grown beyond your company
Create a culture where "moving on" isn't taboo, it is celebrated as personal progress
3. Active Support for Transitions
When someone has outgrown a role, put in the effort to support their transition.
When one of our best product managers expressed that she wanted to move into venture capital, rather than trying to keep her, we connected her with our investors, adjusted her schedule for interviews, and celebrated when she landed her dream role. She's now one of our biggest advocates and has referred several great hires to us.
Here’s the counter-intuitive truth: when you support people's growth - even when at the risk that they might grow away from your company - you create stronger loyalty and more trust.
A lot of businesses have misplaced loyalty ingrained in their culture. I see it all the time in my clients, and peers. CEOs expect their team to give everything with unlimited loyalty to the business.
But the goal isn't to keep people forever.
It's to create an environment where they can do their best work while they're with you, and leave better than they came.
Your company should be a launching pad for personal growth, not a cage that holds people back from it.
Let Adaptability Be Your Team’s North Star
It is crucial to learn to recognize when the team that got you here is not the team that will get you there.
Equally as important is creating values that help your team evolve along with the company.
Since we’re in the business of growth - it’s crucial to embrace adaptability above all within your culture.
The most valuable asset in your company isn't a perfect strategy or a specific expertise—it's your team's ability to adapt and evolve with the business.
Imagine how unstoppable they’d be if they knew what was coming, and how to rise to meet it.
To do that, show your team what scaling looks like ahead of time. Instead of just focusing on revenue, outline what scaling looks like from an operational standpoint.
What does it look like to simplify complexity at all levels of the business?
What systems or tech will you need once you reach a specific market share or client base?
What mini machines will you build, and who will oversee them?
What does it take for our engineering team to work like a machine with precision, calmness, and urgency that is energizing, not draining?
What roles will no longer be needed once you’ve reached a new stage in your business?
One of my favorite tactics is to share future org charts with my team.
Org charts aren't just about who we have now—they're a roadmap for growth. They include blank spots for future roles and highlight areas where technology might replace manual work. This gives everyone a clear picture of how roles will shift and where new opportunities will emerge.
For example, if we have 7 sales development roles to help us build the sales machine, once we nail it, we’ll likely reduce the SDR role by 80% with automation. But we might expand the account management role, or bring on something new with the new customer demand we’ve uncovered.
The key here is to be transparent so the team has the opportunity to adapt as the business scales.
Putting It All Together
Scaling is not just about revenue, or market share. Where most CEOs go wrong is they focus so much on the end goal, they forget to think about how they will get there and with whose help.
Building a business that scales means being honest about who's scaling with you.
By following these five tactics, you can navigate the challenges of when your business has outgrown your team. Remember, it's not about replacing your team, but rather evolving it to meet the needs of your growing business.
Looking For More In-Depth Help?
Here's four ways I can help you:
⚫️ The 20 Hour CEO: Five-week live cohort where you'll learn how to scale yourself and your business, with 1:1 coaching from me. I share my exact methods, playbooks, and actionable strategies for building 3 businesses to $200M. Join the waitlist to learn when the course opens back up.
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