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Matt Verderamo is a consultant at Well Built Construction Consulting, a Baltimore-based construction consulting firm. Opinions are the author’s own.
One of the highest-stakes decisions an owner can make is deciding who will sit at the top of the org chart with them.
When you place someone into a role that is effectively going to help run the business, you are choosing someone who will shape the culture, the pace, the standards, the accountability and the future of the company.
So many owners get this wrong when they treat the hire like a normal executive search. It is not a normal hire.
As an owner, you are choosing someone who must think about the business the way you do.
They need to care deeply, feel ownership, find purpose in building something greater than themselves and want the kind of life that comes with carrying serious responsibility.
It’s important to ask yourself “Can they do the job?” But it is potentially more important to ask: “Do they want the life?” Because these roles do not live neatly inside 8 to 5. That is not how most owners live.

Mat Verderamo
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You do not go through all the risk, pressure, heartache and years of hard work unless, at some level, the mission matters to you deeply. So, if you are evaluating someone to help run the company, they need to have that same kind of relationship with growth and responsibility.
That is why I believe the best top-of-org-chart talent usually has an established pattern in their career.
You should see evidence that:
- They have been hungry for growth over a long period of time.
- They kept stepping into bigger challenges.
- They developed people under them.
- They improved systems.
- They helped a business get stronger, more scalable, more disciplined and more capable.
The interview process
Once you find someone who appears to fit that profile, you can’t just conduct a business-as-usual interview process.
You cannot evaluate top-of-org-chart talent with shallow, one-hour conversations. You need stories, specifics and enough time for the truth to show up.
This is where many companies sabotage themselves. They run a high-level candidate through a normal interview sequence and wonder why the process fails them.
If someone is potentially leaving a strategic leadership role to come help run your business, you should assume this decision will impact every part of their life. Their workload. Their stress. Their energy. Their family rhythms. Their travel. Their identity.
That means your interview process should feel like a deep mutual evaluation.
One of the best ways to do this is with scenario-based conversations.
For example, give them a case study that presents them with limited financial data, some leadership challenges and a few organizational bottlenecks. Base it on your experience or create variables that align with your own current challenges.
Then ask them what they would do in the next 12 months. Pay attention to:
- What they notice first.
- What they ignore.
- If they understand organizational change requires buy-in.
- If they talk like an operator, builder and a leader.
- If they can see around corners.
That kind of process tells you much more than another résumé review ever will.
The family connection
Here is one more thing that I think gets overlooked: If the role is big enough, family alignment matters too. That may sound too personal for some people, but I do not think it is.
When someone takes on one of these roles, their family is taking it on, too. Not in the same way, but the demands are real. The sacrifices are real.
This is one reason why I think owners should treat these hires with enormous care. In some cases, even getting spouses together for dinner is not over the top; it is wise. Better to understand the reality of the fit before the offer than after.
Because this really is closer to a marriage than a hire. The cost of getting it wrong is enormous.
So take your time. Look for the person whose career shows growth, has helped others grow and ultimately who wants the life, not just the title.

