3 Overlooked Qualities to Consider in an Executive Hire

Hiring your first executive leader can feel like handing over the keys to your house while you’re still living in it.

You’re not just giving them a title. You’re trusting them with your clients, your team, and the culture you’ve been carefully shaping since day one.

This hire will change the way your business feels. Not just what gets done, but how decisions are made, how people interact, and what happens when things get hard.

Yes, you’ll hire for the resume, but the real story is in the intangibles. You want to know the way they make calls under pressure, handle bad news, and steer the ship when you’re not in the room.

Hiring an executive isn’t just about who they are on their best day, but rather who they are on the day everything goes sideways.

Those are the skills you can’t easily put in a job description.

I’ve seen too many founders get swept up in the hard skills and miss the quieter signals that tell you how someone will actually lead. Before you make the leap, here are three little-talked-about things to look for when hiring a senior leader. This is the stuff no glossy hiring checklist will cover, but ultimately makes or breaks your first executive hire.

1. What’s Their Relationship to Accountability?

Accountability isn’t just about taking ownership when things go wrong. Accountability is how someone holds themselves and others to what matters most without burning the whole team out in the process.

We’ve seen some executives lean so far toward empathy that they can’t have the hard conversations. Others are so focused on accountability that they end up smothering their team and quietly doing everyone’s job to keep things moving. Both burn out, one slowly, and one spectacularly.

We look for leaders who can balance both. An ideal leader can sit with an underperforming team member and say, “I get it, this was a hard quarter,” and also, “Here’s what’s going to change moving forward”.

Pay attention to how they talk about mistakes, especially their own. If they never bring up a time they dropped the ball, that’s a red flag. But so is the person who takes the blame for everything. It might sound noble, but it’s typically a sign they can’t delegate in a way that truly frees up their time and capacity to lead. An executive who can’t delegate becomes another very expensive bottleneck.

When you’re interviewing, give them a real scenario from your world. Try something like, “We missed a major deadline because two team members didn’t deliver. How would you handle it?”

You’re not looking for a perfect answer, but rather for their instincts. Do they go straight to who to blame? Or do they start by asking why it happened and how to prevent it next time?

2. Have They Had to Lead Through Unpopularity?

A lot of leaders get to the top by being well liked. They have been able to keep the peace, make people feel good, and avoid conflict to maintain connections.

That charm can open doors, but sooner or later, every executive hits a wall where being liked and doing the right thing are not the same. This is where you find out if they can actually lead.

When you hire your first executive, you’re handing them the authority to make calls that might not win applause. They may have to cut a beloved but underperforming service line, restructure a team, or tighten up client boundaries. If they’ve never been in that position before, you’ll see hesitation, sugar-coating, or the “maybe it’ll fix itself” stall. Hard decisions don’t fix themselves; they just compound.

Ask them about a time they made an unpopular decision. Not just what they did, but how they navigated it. Did they explain the why? Did they own it publicly instead of hiding behind the company? Did they come out the other side still respected, even if not adored?

Leadership isn’t a popularity contest. Leadership is a stamina test. You want to hire the person who can stand in discomfort long enough to see the right decision through, handle the side-eyes in the hallway, and stay steady while people adjust to change they didn’t choose. 

The executives who can do that are rare, and they’re worth their weight in gold.

3. Do They Have Strategic Maturity?

Strategic maturity isn’t about having the smartest idea in the room. It’s about knowing which problems to solve, and in what order, when everything feels urgent.

An immature leader will zoom straight in on the person who messed up, because that’s the obvious target. A mature leader questions what in our system allowed this to happen. They know you can replace a person, but if the system stays broken, the problem will keep coming back.

Additionally, make note of how they prioritize. When presented with five fires, do they run to the biggest flames or start with the sparks that could turn into bigger ones? Do they see the short-term wins without losing sight of the long-term play?

Strategic maturity isn’t about being slow or overly cautious. It’s about being nimble without being reactive. A great leader can zoom out to see the whole board, then zoom in to make the right next move.

Ask them about a time they had to choose between a short-term opportunity and a long-term strategy. How did they decide? What did they weigh first? If all they talk about is the immediate win, that’s a sign they may not have the altitude to build for the future.

Your first executive leader needs to be able to hold the tension between today’s demands and tomorrow’s growth. They need to know when to play offense, when to shore up defense, and when to step back and reset the entire game plan.

That’s not just leadership. That’s stewardship.

To wrap it up

Hiring your first executive leader will change your business in ways you can’t fully anticipate. It’s not just about what they do, but about how they lead, what they notice, and how they show up when the easy answers are gone.

Their resume will tell you if they can do the job, and the interview will tell you if they can talk about the job, but these little-known filters will tell you how they’ll actually lead when it’s your job and theirs on the line.

When you find someone who balances empathy with ownership, who can stand steady in the face of hard decisions, and who sees the whole playing field before they move a single piece, you’ve found a partner, not just an employee.

That’s the real goal. We are not looking to fill a seat, but to share the table with someone who will help turn the business into an asset worth protecting.

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