Doubting your first hire? Here’s how to handle it.
👋 Hi, it’s Olivia, and I’m here with this week’s edition of The Midnight Text—Forum Ventures’ bi-weekly newsletter tackling the honest, messy, and often unspoken moments that keep founders up at night.
I’m a Partner & COO at Forum Ventures, where I lead our Platform team across marketing, post-investment support, and operations. I’ve spent my career building brands, launching products, and turning early traction into real momentum. I’m a generalist at heart, most at home in the zero-to-one chaos.
Up today: You’ve hired your first employee and you have a feeling it’s not working out.
It’s 2am. You’re staring at the ceiling. You’ve run this spiral a dozen times before:
Is it me? Is it them?
What if I can’t find someone else fast enough?
I need this to work.
Maybe next week will be better.
You’ve invested time and emotion in this hire, you don’t want to restart the process. It was long and exhausting the first time, and you really want it to work. But you also know it’s important to make a decision and take action.
So, what do you do when you start to feel that something’s off?
There are three common reasons why a first hire might not be working:
1. Skillset mismatch
They’re missing deadlines, needing too much direction, or not stepping into the role the way you expected.
2. Misalignment on role expectations
This happens when someone signs on thinking they’ll be a strategist, but the job needs an executor. Or they’ve come from a bigger org and weren’t ready to go full scrappy mode.
3. Culture or values misfit
Sometimes it’s not about output. At the early-stage, how people work together is just as important as what they get done. If collaboration feels heavy or values aren't aligned, it can slow down everything.
Let’s break them down and talk about how you can tackle each scenario.
Skillset or performance issues
While you’re not feeling satisfied with performance, remember that people need time to ramp. Give this employee grace to onboard effectively, and don’t expect the world from them from day 1.
If after a month or two you start to notice patterns like missed deadlines, not actioning feedback, or a lot of handholding without follow-through, it’s time to look more closely.
Here’s where many founders slip: They avoid the hard conversations, hoping things will magically improve. Avoiding feedback isn’t kind and it’s not what good leaders do.
It’s far kinder (and more effective) to be clear, direct, and give someone a real chance to succeed.
Before assuming it’s purely a performance issue, ask yourself some hard questions:
Have I been clear and explicit about what success looks like?
Have I provided them with the right tools, context, and support?
Have I created space for them to course correct?
If the answer is no to any of them, take time to talk to the employee, provide honest feedback, set very clear expectations, and give them a chance to come through. Try:
“Right now, I’m not seeing the execution I need in this role (provide examples of where they are falling short). Here’s what success looks like over the next 30 days (deliverables, numbers). Do you feel equipped to hit this? What do you need from me?”
You might be surprised by what you learn. Or confirm your initial hunch.
Role or company-stage mismatch
This happens more often than you think at startups. If an early hire hasn’t worked at a pre-seed stage company, they might not totally comprehend what you mean when you say they need to work lean, scrappy, and wear lots of different hats.
For example, a founder in our portfolio hired a “Head of Sales” expecting a strategic leader who could also outbound to prospects, take the calls, build the sales deck, and close the deal. But the hire was looking to lead, not do. So, unfortunately, they had to part ways.
Unless they’ve been a first hire before, you need to be very explicit during the interview process that they will have a small budget, little resources, next to no structure, and responsibilities that might fall slightly outside of this role. Use a lot of concrete examples of what things could look like:
“Here’s what our budget looks like. Here’s how much support you’ll have. Here’s what you’ll be responsible for in the weeds. Here is the realistic timeframe before you will hire your first report.”
Don’t assume they get what “early stage” means. Ask for specific examples of scrappy execution from their past.
If you’re realizing this is the cause of your current mismatch, talk to the employee. Level set on what the role entails, re-state what they can expect if they continue to work here, and provide the opportunity for them to re-commit with more knowledge or opt-out comfortably if they feel that this role is not for them.
Culture or values misfit
Here’s where most founders get stuck.
Early team dynamics feel off, but they don’t say anything. They hope it’ll sort itself out. That with time, process, or growth, things will just… click.
Spoiler: it won’t.
When you’re a tiny team, 4 people crammed into a WeWork, how you work is everything. Every hire shapes the vibe, the pace, the trust. If something feels misaligned now, it’s not magically going to fix itself later.
But that doesn’t mean you just cut ties the second things feel weird. If you’re feeling friction:
Say something early.
Be clear about where things aren’t clicking, whether it’s communication or collaboration or something else.
Set expectations and give them a real shot to course correct.
But if after that, it’s still not working? That’s your call to make. And yes, sometimes, “it’s just not the right fit” is enough. At the end of the day, your job is to protect the team you’re building. The real culture, not just the values on your Notion doc. In the early days, you can’t afford to get that wrong.
Can I avoid this next time?
The reality is, you won’t catch everything for every hire. Here are some quick tips for your hiring process that will give you the strongest chance of success:
Get extremely clear on what you need from that first hire: Execution? Experience in chaos? Someone who’s done it before?
Use paid trial projects or short-term contracts before a full-time offer.
Always, always check references. If you can backchannel, even better!
Layer in social touch points like a walk, a lunch, even a casual Zoom coffee, to get to know them as a person
Try a group working session with you and your co-founder
Look, when an early hire doesn’t work out, it sucks. But dragging it out can interrupt your sleep and slow down your company’s momentum. I know it feels like restarting the hiring process will slow you down. But trust me, keeping the wrong person will slow you down way more.
So get clear. Have the hard conversations. Set clear expectations. Give them the chance to meet them. And if it’s still not working, make the call.
You got this.
Olivia
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