June 23rd, 2026

The most expensive hire you'll ever make is the one that makes a structural problem invisible for another eighteen months.

Many IT services owners hire when they're overwhelmed. That's understandable. It's also, more often than not, the wrong response to the right problem.

Overwhelm is a symptom. The cause is usually one of three things: the work has outgrown the process, the decisions have outgrown the decision architecture, or the team has outgrown its clarity about who owns what. Hiring into any of these conditions doesn't fix them. It adds a salary to a broken system — and for a while, it makes the system feel like it's working.

That feeling is the expensive part. When a new hire absorbs enough chaos to reduce the founder's immediate pressure, the underlying problem gets shelved. Six months later, the hire is struggling. The founder is getting pulled back in. The business is running essentially the same way it was before, just with a larger payroll.

You can't hire your way out of a structural problem. You can only make it more expensive.

The Difference Between a Capacity Problem and a Structure Problem

A capacity problem is real, and the solution is people. The team is doing the right things the right way, but there simply isn't enough time or bandwidth to do them at the volume the business requires. Hiring solves this. You add a person, throughput increases, and the problem goes away.

A structural problem is different. The team isn't doing the wrong things because they're bad at their jobs — they're doing the wrong things because nobody defined what the right things are. Roles overlap. Decisions land on whoever is available. Work gets done, but not in any repeatable way. Hiring into this makes it worse. You add a person to an undefined system, and now you have one more person contributing to the entropy.

Diagnosing the right problem does not have to be hard. When something breaks in your business — a client escalation, a missed deadline, a billing error — trace it back to its root. If the answer is 'we didn't have enough people,' that's a capacity problem. If the answer is 'we didn't have a clear process for that,' that's a structural problem.

Three Hires That Almost Always Happen Too Early

These aren't bad hires in the abstract. They're premature hires — brought in before the conditions for their success are in place. The pattern is consistent enough across IT services businesses to warrant naming directly.

The second-in-command: The founder is overwhelmed. Someone needs to take things off their plate. A COO or director of operations seems like the answer. If decision rights haven't been defined, the new hire inherits the chaos. They spend their first six months figuring out what they actually own. The founder remains the default for anything ambiguous — which is most things.

The sales hire: Revenue has plateaued. The founder is still closing most deals. A salesperson will free them up and accelerate growth. Without a documented sales process, the new hire spends months reverse-engineering how the founder sells — which they can't fully replicate. Win rates drop. The founder gets pulled back in. The hire looks like a failure when it's actually a process gap.

The project manager: Delivery is chaotic. Deadlines slip. Clients escalate. Someone needs to bring order to the operation. If escalation protocols and scope definitions don't exist, the PM spends their time triaging problems the system created. They become a very expensive coordinator for a process that was never designed.

The common thread across all three is the same. The hire is made to solve a pain the founder feels, without first identifying the root cause. Pain is not a job description. A job description requires knowing what the person will own, which decisions belong to them, what success looks like in 90 days, and what to escalate versus handle. Most businesses that make these hires prematurely can't yet answer those questions.

What to Fix Before You Hire

The sequence matters. Three things are worth getting clear on before any senior hire — not because perfection is required, but because each one directly affects whether the person you hire can succeed.

Define what the role owns — not what it does. A role that owns outcomes is accountable. A role that does tasks is a pair of hands. Before hiring, write down the three things this person will be responsible for delivering in the next 12 months. Not activities — results. If you can't write that list, the role isn't ready to be filled.

Map the decisions that currently land on you. Take 15 minutes to list every recurring decision that comes your way — in email, Slack, and side conversations. For each one, ask whether it genuinely requires your judgment or whether it defaults to you because no one else has been given the authority to handle it. The second category is your delegation map. That's what the new hire will own.

Document the one process most likely to break under them. Every new hire touches a process on day one. If that process isn't documented, the hire will either invent their own version or ask you every time something unusual happens. Before they start, write down how that process works today — not how you'd like it to work, but how it actually works. That document is their onboarding manual, and it takes you two hours to create.

The Right Question Before Any Hire

Before signing an offer letter, answer this honestly: if this person joined tomorrow and you disappeared for three weeks, what would break? If the answer is 'everything,' the hire will fail because there's no system for them to operate in. If the answer is 'a few specific things,' good. Document those things. Then hire.

Hiring is not the time to build the system. It's the time to bring someone into a system that already exists. The founder's job before the hire is to build enough structure so the person they're bringing in has something to work with on day one. That work is unglamorous and is almost always deferred. It's also the only thing that determines whether the hire succeeds.

What's the next hire you're considering — and have you answered the three questions above? Hit reply. I read every response.

JP Van Steerteghem

+1-617-548-3863

[email protected]

https://calendly.com/jvansteerteghem