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I was meeting with a small company recently. They are in one of those exciting moments where everything is growing at once. They are opening new offices. They are hiring aggressively. They are investing in beautiful new spaces. Their conference table alone probably cost more than most people’s cars.
But here’s the disconnect. For all the money going into new hires and new office space, not a dime is being spent to invest in their first-time managers.
And that is exactly where their growth is most at risk.
This is something I see over and over. Companies hit a growth spurt and start spending on everything that looks like growth: people, space, product. But the managers, especially the first-time managers, are left to figure it out alone.
Here is what usually happens. A top-performing IC gets promoted. They know the product better than anyone. They’ve been loyal from the early days. They have crushed it in their role. Six months later, their team is disengaged, turnover is ticking up, and leadership is confused about why things are slipping.
The story is almost always the same. It is not a culture fit problem. It is not that the person wasn’t ready. It is that the company never gave them the tools to lead.
What Happens When You Don’t Invest
When you skip investing in first-time managers, you are not saving money. You are creating hidden costs that pile up fast:
Attrition goes up. People do not quit jobs, they quit managers.
New hires fail to ramp. Onboarding lives or dies by the manager.
Your new manager burns out. The rockstar IC who was once your most reliable employee now feels like they are failing.
Recruiting costs explode. Instead of building on the team you have, you are stuck backfilling again and again.
What First-Time Managers Actually Need
It is not complicated. They do not need a week-long retreat or a 500-page playbook. They just need real support.
Clarity about what “good management” looks like at your company.
Training on the basics, like running 1:1s, giving feedback, and coaching instead of doing everything themselves.
A mentor or someone safe to call when things get messy.
Feedback loops so they know what is working and what is not.
The ability to admit they are new at this without fear of being seen as weak.
Give them that, and your best ICs can become your best leaders. Leave them on their own, and you are setting them up to fail.
Why This Matters for Recruiting
This is not just a people team issue. It is a recruiting issue.
If your managers cannot lead, your best hires will leave.
Word travels fast. Poor management kills your reputation, and suddenly sourcing gets harder.
You inflate your costs by constantly backfilling instead of compounding on the talent you already have.
Recruiting does not stop at the offer letter. It continues every single day through the people who lead your teams.
For Candidates
If you are interviewing at a growth-stage company, pay attention to how they talk about managers. Ask about how they train, support, and invest in them. If the answer is fuzzy, vague, or gets brushed off, take note. That lack of investment in leadership will eventually be your problem.
Here is why this matters: your manager will be the single most important factor in your long-term success and happiness. They are the person who clears roadblocks for you, advocates for you, and shapes your day-to-day. A good manager can fight for you, coach you, and help you grow faster than you thought possible. A bad manager can make even the “dream job” miserable.
We recently saw this play out in real time. A candidate of ours was offered a role, and at first, they declined. The sticking point? An internal PTO policy. Most people would have shrugged and moved on, but the hiring manager knew this candidate was exactly who they wanted on their team. So he fought for it. He went back to HR, pushed for a change, and made the case that this candidate’s impact was worth changing the rule. The company agreed, the offer came back around, and this time the candidate said yes.
That is what a great manager does. They fight for their people before they are even officially on the team.
So when you are evaluating opportunities, do not just focus on the title, the salary, or the product. Focus on the manager. Ask how they are trained. Ask how they are supported. Ask how they advocate for their team. Because the answer to those questions will tell you more about your future than any job description ever could.
The Bottom Line
Your first-time managers are the backbone of retention. They are the bridge between your vision and your employees’ day-to-day.
If you ignore them, you will bleed talent. If you invest in them, every hire you make will stick longer, grow faster, and compound.
Because recruiting does not stop at the offer. It lives or dies with the people leading your teams.
👉 If you are unsure whether your managers are helping or hurting retention, reply to this email. Let’s talk about a Hiring Health Check.
See you next Monday,
Robin
#gorogue
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