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Matt Verderamo is a consultant with Well Built Construction Consulting, a construction consulting firm based in Baltimore. The opinions are the author’s own.
One of the most important decisions an owner can make is deciding who will sit at the top of the organizational chart with them.
When you place someone in a role that will effectively help run the business, you are choosing someone who will shape the culture, pace, standards, accountability and future of the company.
Many landlords make the mistake of treating hiring as a normal executive search. It is not a normal recruitment.
As an owner, you are choosing someone who needs to think about the business the way you do.
They need to deeply care for themselves, feel ownership, find purpose in building something bigger than themselves, and want the kind of life that comes with serious responsibility.
It is important to ask yourself “Can they do the job?” But it’s potentially more important to ask, “Do they want life?” Because these roles don’t live perfectly within the 8 to 5. That’s not how most owners live.

Mat Verderamo
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Don’t go through all the risk, pressure, pain, and years of hard work unless, on some level, you care deeply about the mission. So if you’re evaluating someone to help run the company, they need to have the same kind of relationship with growth and responsibility.
That’s why I think the best talent on the org chart tends to have an established pattern in their career.
You should see evidence that:
- They have been starved for growth for a long period of time.
- They kept going into bigger challenges.
- They developed people under them.
- They improved the systems.
- They helped a business become stronger, more scalable, more disciplined and more capable.
The interview process
Once you find someone who seems to fit that profile, you can’t go through a normal interview process.
You can’t evaluate talent at the top of the org chart with one-hour perfunctory conversations. You need stories, details and enough time for the truth to emerge.
This is where many companies sabotage themselves. They run a high-level candidate through a normal interview sequence and wonder why the process is failing them.
If someone is potentially leaving a strategic leadership role to come help run your business, you should assume that this decision will affect every part of their life. Your workload. Your stress. His energy. Their familiar rhythms. Your journey Your identity
This means that 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 limited financial data, some leadership challenges, and some 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 that organizational change requires acceptance.
- If they talk like an operator, a builder and a leader.
- If they can see around the corners.
This type of process tells you a lot more than just another resume review.
The family connection
Here’s one more thing that I think gets overlooked: if the role is big enough, family alignment matters too. This may sound too personal for some people, but I don’t think it is.
When someone takes on one of these roles, so does their family. Not in the same way, but the demands are real. The sacrifices are real.
This is one of the reasons why I think owners should treat these hires very carefully. In some cases, even bringing the spouses together for dinner is not excessive; he is wise Better to understand the reality of the adjustment before the offer than after.
Because this really is closer to a marriage than a rental. The cost of getting it wrong is huge.
So take your time. Look for the person whose career shows growth, has helped others grow, and ultimately wants the life, not just the title.
