Matt Verderamo is a consultant at Well Built Construction Consulting, based in Baltimore. The views expressed in this article are solely those of the author.

For business owners, one of the most critical decisions is deciding who will stand alongside them at the top of the organizational structure. When you place someone in a position that will effectively help run the business, the person you choose will shape the company's culture, pace, standards, accountability mechanisms, and future prospects.

However, many business owners make a mistake at this point—they handle this decision like an ordinary executive hire. But this is not an ordinary hire.

As a business owner, the person you choose must think about the business the way you do. They need to care deeply, have a sense of ownership, find meaning in building something beyond themselves, and desire the lifestyle that comes with significant responsibility.

Asking yourself "Can they do the job?" is important, but perhaps more important is asking: "Do they want this life?" Because these roles cannot be strictly confined to a nine-to-five—most business owners' lives are not like that.

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Mat Verderamo
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Unless the mission matters deeply to you on some level, you wouldn't endure all the risk, stress, heartbreak, and years of hard work. So, if you're evaluating someone to help run the company, they must have the same attitude toward growth and responsibility.

That's why I believe the best top-tier talent typically shows an established pattern throughout their career. You should see evidence of the following:

  • They have remained hungry for growth over a long period.
  • They have continually taken on bigger challenges.
  • They have developed the people under them.
  • They have improved systems.
  • They have helped make businesses stronger, more scalable, more disciplined, and more capable.

The interview process

Once you find someone who seems to fit this profile, you can't just use the standard interview process. You can't assess top-tier talent with a shallow one-hour conversation. You need stories, details, and enough time for the truth to surface.

This is where many companies limit themselves. They put a senior candidate through the standard interview process and then wonder why the process let them down.

If someone might leave a strategic leadership role to help run your business, you should assume this decision will affect every aspect of their life—workload, stress, energy, family rhythm, travel, identity. That means your interview process should be like a deep, two-way assessment.

One of the best ways to achieve this is through scenario-based conversations. For example, give them a case study with limited financial data, some leadership challenges, and a few organizational bottlenecks. Design the case based on your experience, or set variables that align with your current challenges.

Then ask what actions they would take over the next 12 months. Pay attention to the following:

  • What they notice first.
  • What they overlook.
  • Whether they understand that organizational change requires buy-in.
  • Whether they speak like an operator, builder, and leader.
  • Whether they have forward-thinking vision.

This kind of process tells you far more than any resume review.

The family factor

There's another point I think is often overlooked: if the role is important enough, family alignment matters too. This may sound too personal to some, but I don't think so.

When someone takes on these roles, their family takes them on too. Though in different ways, the demands are real, and the sacrifices are real. That's why I believe business owners should be extremely careful with these hires. In some cases, even having dinner with the spouses isn't excessive—it's wise. It's better to understand the reality of the fit before extending an offer rather than after.

Because this really is more like a marriage than a hire. The cost of getting it wrong is enormous. So, take your time. Look for people whose careers show growth, who have helped others grow, and who ultimately want this life rather than just a title.