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"Goodbye" Is The Hardest Word: What To Do When Your First Employees Are Hitting A Ceiling
- Milly Barker
- Apr 2
- 6 min read
In the beginning, there was the word. And the word was basically what you imagine a panicked version of the shrug emoji would sound like. You had a lot of shit to get done, but you weren't 100% sure what that shit was or how to do it or who would do it.
It was just you and a few gallant builders against the world. And these gallant builders, your first hires, didn't join your company for the perks or the pension; they joined for the mission. Chances are that they were "Generalists" - Swiss Army knives masquerading as humans who could wear five hats at once, happily worked alongside you late into the night, and absolutely duct-taped your MVP together when it was falling apart.
You owe them a lot and you know it. Perhaps, if you're truly honest with yourself, you owe them everything.
But as a startup matures from a scrappy project into a scaling product-market fit machine, a painful reality often emerges: the skills that got you to £1m are rarely the same skills that will get you to £10m. And I'm not just talking about YOUR skills as a Founder, I'm talking about those people to whom you owe this world you've built.
When you start to wonder if your first employees are hitting a ceiling, it's really easy for panic and worry to set in. But please don't worry, this is a common (and necessary) part of growth and a sign that you're doing something right.
The Generalist vs. The Specialist
In the early days of a business, you need people who can pivot on a penny. You need firefighters and champions and brave, brave defenders. But scaling is different; scaling requires single-minded architects and planners and targeted missiles of humans who live to build repeatable systems, manage large teams, and who thrive in the kind of structured environment that early hires can find stifling.
It is a rare individual who can transition from being the person who does the work to the person who builds the system that does the work and who steps back without feeling bored to actual tears. When an early employee hits their ceiling (again, yourself included), nothing inherently "wrong" has happened and it isn't a failure of character, it’s just a shift in the company’s biological needs.
The cost of hesitation when your first employees are hitting a ceiling
I have this conversation a lot with our clients in the "scaling" stage of their growth - it feels "kind" to keep a loyal early hire. You tell yourself you’re being loyal to them too. But, in reality, stalling this decision is one of the most unkind things you can do.
The kindest thing you can do for everyone involved in your company (again, yourself included) is keep it running. And that involves making some very hard decisions because here's what happens if you don't:
For the employee: Keeping someone in a role when they are underwater is a recipe for burnout and anxiety. They know they are struggling, and watching the company outgrow them in real-time is demoralising and scary.
For the team: A scaling business needs functional leadership. If a department head can't build the necessary processes, the high-performers underneath them will eventually leave out of frustration.
For the business: Investors look at the strength of the company as a whole. If your C-suite is comprised entirely of "day-one" friends who lack the experience to scale, it signals a lack of operational maturity that can kill a funding round.
How to handle it your first employees hitting a ceiling with grace and care
Moving on from an early hire doesn't have to mean a bridge-burning exit - if you do it right (and that never involves leaving it too long). If handled thoughtfully, you can preserve the relationship while also protecting the business:
Be transparent early on: Don't let it be a surprise. Have regular "role fit" conversations as the company hits new milestones.
Don't inflate titles: Your first marketing hire doesn't need to be called "CMO". Honestly, in the earlier stages of the business, a Founder might not even need to be "CEO". It gives me the ick a little when I meet really early stage businesses and they have a full C-Suite but no clear problem statement or solution - it's a little "cosplaying at bizniz" for my tastes.
The "right seat" conversation: Sometimes the early hire doesn't need to leave, they just need to move. Even if you've given a higher title than perhaps you needed to, can they move laterally? A "Head of Sales" who loves selling but hates managing a team of 20 might be much happier (and more effective) as your "Lead Individual Contributor" or "Founding Account Executive." Senior doesn't always mean "managing people".
Honour the legacy: If they do need to move on, celebrate them. Acknowledge publicly that the company exists because of their contribution.
Generous off-boarding: If they’ve helped you build a valuable company, ensure their exit package and equity treatment reflect that if you can.
5 questions to ask yourself to determine if your first employees are hitting a ceiling
The ultimate loyalty of a Founder is to the mission (the promises you've made to your customers) and the entire team, not just the first five people who walked through the door.
It feels cold, but if you're the Founder, your job is to ensure the company survives to fulfil the promise you made to everyone - including those early believers. Sometimes, being a "good leader" means making the heartbreaking choice to bring in the specialist who can take the baton for the next leg of the race.
Here are some prompts you can use to ask yourself if it's time for some tough conversations:
If I were hiring for this leadership role today, knowing what the next 18 months look like, would I hire this person? Don't look at who you have and determine what their role should be - look at what you need to get done and determine what your hiring strategy should be.
Is this person struggling because of a lack of resources, or because the complexity of the role has fundamentally changed?
Are the high-performers underneath this person thriving, or are they stagnating?
Is my hesitation to change roles based on the business's needs, or my own guilt? It can help to ask an objective, external adviser if you're struggling with this one (if in doubt, give me a call - I'll tell it to you straight).
What is the "opportunity cost" to the company of having a B-player in this A-player role for another six months? What do you need to achieve and what are you actually going to achieve if you keep this person in their current seat?
Building a business is a series of evolutions, and your role as a leader is to shepherd the company through every single one of them. It’s important to remember that outgrowing a role isn't a reflection of an individual's worth, it's a reflection of the company’s success - your company. If you weren't growing, you wouldn't have these issues. Be proud that you've gotten to this place because most companies don't.
That said, knowing that a change is necessary and actually executing it are two very different things. The emotional weight of these decisions is exactly why so many founders wait too long and only take action once the friction has started to damage the culture or the bottom line.
Please remember, you don’t have to navigate these high-stakes transitions in isolation. You're not the only one going through this and it's ok to ask for help. Sometimes, you need a neutral, experienced perspective to help you audit your org and identify where the gaps are, and, most importantly, help you design a transition plan that is both professionally rigorous and deeply human.
If you’re feeling the friction and aren’t sure how to move forward without breaking the culture you’ve worked so hard to build, let’s talk.
Before you go: a final gut-check
If you’re still on the fence about whether it’s time to make a change, ask yourself this:
"If I don’t make this choice today, am I being loyal to one person at the expense of the mission we all signed up for?"
True leadership isn't about avoiding the hard conversations. It's about having them with the clarity and kindness that your early believers deserve.
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