What to Do When You’ve Outgrown Your Early Hires

When loyalty meets performance debt: how to move gracefully (and avoid entitlement culture).

Author

Regina Gerbeaux
August 31, 2025 • Reading Time: 10 minutes

Hi! Welcome to another issue of Force Multipliers, your weekly briefing from Regina Gerbeaux, where Silicon Valley's behind-the-scenes operators get battle-tested frameworks for their toughest challenges, from putting out chaotic fires to managing strong personalities.

Dear Regina,

I'm struggling with a situation that's keeping me up at night. We've grown from 8 people to 85 in the last 18 months, and some of our earliest hires are struggling. These aren't bad people; they're culture carriers who bled for this company when we had no money and worked weekends for equity that might have been worthless.

But we need specialists now, not generalists. We need people who can navigate high-stakes decisions, not just hustle through whatever comes their way. I feel like an awful person even thinking about this, but I'm worried that keeping them in their current roles is actually hurting both them and the company.

How do I handle this without looking like I don't value loyalty? And how do I know when someone can grow into the role versus when I need to hire externally?

Dear Operator,

You're dealing with one of the most emotionally complex challenges in scaling companies: what to do with early hires when they can no longer keep up.

The tension between honoring early contributions and doing what's best for the company's future is real and can be very painful.

I’ve heard it said many times in coaching sessions: leaders tell me they’re afraid of letting early hires go. They worry that they’re sending a message that they don’t value longevity and loyalty. They feel like letting an early hire go, even when it’s necessary for the company, means they’re being disloyal to their early teammates.

But here's what I want you to understand: having this conversation doesn't make you disloyal. Avoiding it does.

When you let someone struggle in a role they've outgrown, you're not being kind. You're being cowardly. And both they and your company suffer for it.

Let me give you a playbook for navigating this with integrity and care.

The Playbook on Managing Outgrown Early Hires

Step 1: Understand the Two Types of Outgrowing.

Communities work exceptionally well if you’re willing to put in the time and effort to make the most out of it.

The Generalist-to-Specialist Shift

Early stage companies need people who can learn quickly and handle a little bit of everything. But as you scale, you need depth over breadth.

The operations generalist who used to handle finance, partnerships, and vendor management now needs to choose a lane and go deep.

This isn't about intelligence. The company needs focus and specialization now, so this generalist needs to adapt.

The Risk Tolerance Evolution

In the early days, if the company messes up and makes mistakes, you're irrelevant. So no one cares.

Breaking rules and asking for forgiveness works when you're selling stuff without a license just to see if people will buy.

But when you're worth hundreds of millions and attracting attention, you need someone wise enough to know when risk is worth it and when to play it safer. The stakes have fundamentally changed.

Step 2: Look Beyond the Horizon.

The best operators don't wait for these conversations to become emergencies. They plan ahead.

If you want to simplify it, here it is: If I were hiring for this role from scratch today, would I hire this person? That gives you your answer.

FURTHER QUESTIONS TO ASK YOURSELF:

If we're doing international expansion two quarters from now, can our current expansion person handle that complexity?

If we're launching premium partnerships, can our partnerships owner manage VIP relationships?

What does success look like in each role 12 months from now?

Thinking ahead helps you figure out if you can ask someone to rise to the occasion, or if you need to hire someone more senior.

Step 3: Create Psychological Safety for Honest Conversations.

The best employees often have enough self-awareness to know whether they're capable of stepping into bigger shoes. When there's real psychological safety, they'll share their own fears about not being able to keep up.

Start with what the company needs, not what the person is lacking:

"As we scale, we're going to need someone who can build complex financial models and manage enterprise vendor relationships. I want to talk about whether this feels like an exciting challenge for you, or if it's outside your zone of genius."

Notice how this frames it around company needs and personal strengths, not personal deficiencies.

Did you miss last week’s Force Multipliers write-up? I dive into how you can create psychological safety with your team - read more here.

Step 4: Consider the Partnership Model.

Here's where most operators get this wrong: they think the only options are promote or fire.

There's a third option: the partnership model.

This is where you layer the early employee by bringing in someone with more technical skills and experience.

But you don’t let the early employee go. Instead, you…

  1. Involve the early hire in the hiring process of their layered hire

  2. Present it as a “partnerships” kind of relationship (think of it like a CoS role to the senior hire)

The external person has the technical knowledge but lacks cultural understanding and historical context. Your early hire has that in spades. Together, they're stronger than either would be alone. This is a situation where 1+1 truly equals 3.

I've seen this work beautifully when framed correctly. Instead of a demotion, it becomes hands-on mentorship and cultural preservation.

Step 5: Decide when to hire externally, and when internal growth works.

Sometimes you do need to hire externally. This is especially true for big leaps in seniority or highly specialized roles.

It's hard for an early ops hire to jump into a COO role. It's hard for someone who helped with local business development to lead international expansion.

These transitions aren't impossible, but they're not common. Be realistic about the gap and the timeline.

On the flip side, internal growth makes sense when the product or customer base is so specialized that external context would actually hurt.

Does it make sense for someone leading rideshare expansion domestically to also handle international markets? Maybe, if government relationships and local cultural knowledge are more important than pure expansion experience.

The more your product is shaped by specific regulations, cultures, or unique customer needs, the more valuable that internal context becomes.

Step 6: Handle the Conversation with Care

When you're ready to have the conversation, remember that the best early hires are culture carriers. They deserve respect and transparency.

Start with appreciation: "You've been fundamental to getting us here. Now I want to make sure we set you up for success as we continue growing."

Then get clear on what would make them happy moving forward - whether that's with the company in a different capacity, or somewhere else where they can thrive.

If they're not keeping up and don't want to be "siloed" into what feels like a lesser role, ask directly: "What would make you happy and fulfilled in your next chapter?"

Sometimes the kindest thing is helping them find a role elsewhere where they can be a star again.

The Loyalty Question

Let me address the elephant in the room: loyalty.

True loyalty isn't keeping someone in a role where they're struggling. True loyalty is having honest conversations about where they can thrive and setting them up for success, even if that means they leave.

The best early hires want to see the company succeed. When you frame these conversations around company needs and personal fulfillment rather than personal shortcomings, you'll be surprised how often they're relieved to have the conversation.

Remember, the people watching these decisions aren't just looking at how you treat the person leaving. They're looking at how you handle difficult conversations with honesty and care.

Final Thoughts

Outgrowing early hires is a sign of success, not failure. It means you've built something that's scaling beyond what any of you originally imagined.

The goal isn't to avoid these conversations. The goal is to handle them with the same thoughtfulness and care that those early employees showed you when you had nothing to offer but equity and a dream.

Your early team took a bet on you when the outcome was uncertain. Now it's your turn to take care of them as the company evolves.

Sometimes that means creating new opportunities within the company. Sometimes it means helping them find their next great adventure elsewhere.

Both can be acts of loyalty and respect.

Until next time,

And if you’re reading this - you're already ahead.

Because you know where to find the stuff that’s actually good. Like my templates and resources, and this newsletter.

Resources Mentioned 📌 

Was this newsletter forwarded to you? Are you here for the first time? If so, remember to subscribe below…

Want more operational content?

Check out Coaching Founder for over a dozen free, downloadable Notion templates to use at your company, and tons of write-ups on how to level up your execs, your teams, and yourself.

About Regina Gerbeaux

Regina Gerbeaux was the first Chief of Staff to an executive coach who worked with Silicon Valley’s most successful entrepreneurs, including Brian Armstrong (Coinbase), Naval Ravikant (AngelList), Sam Altman (OpenAI / Y Combinator), and Alexandr Wang (Scale).

Shortly after her role as Chief of Staff, then COO, she opened her own coaching practice, Coaching Founder, and has worked with outrageously talented operators on teams like Delphi AI, dYdX, Astronomer, Fanatics Live, and many more companies backed by funds like Sequoia and Andreessen Horowitz.

Her open-sourced write-ups on Operational Excellence and how to run a scaling company can be found here and her templates can be found here.

She lives in the Pacific Northwest with her partner Lucas and dog Leia, and can be found frequenting 6:00AM Orangetheory classes or hiking trails nearby.

Reply

or to participate.