Hiring the right Chief Operating Officer (COO), Managing Director, VP of Operations, or Director of Operations can feel like finding a unicorn.
You’re looking for someone who can execute your vision effectively, solve complex people problems, and handle challenges with finesse. In other words, you want someone who blends Warmth and Competence—someone who can lead without steamrolling your team.
As an agency owner, you also need a COO who respects that it’s your company… while being willing to challenge you constructively when necessary. It’s a balance between independent thinking and alignment with your leadership style is critical. If you follow EOS, they’re the “Integrator” to you as the “Visionary”—or what I refer to as “Finisher vs. Starter.”
Want to ensure you hire the right person, instead of a secretly toxic employee? One key is to conduct thorough reference checks.
To help you navigate this process, here’s a guide to 12 essential reference-check questions designed to uncover whether your candidate is truly the right fit for you and your agency. It’s the latest in my series on hiring a second-in-command at your agency. You can ask yourself these questions, if you’re promoting from within.
1. How likely are you to re-hire them, on a scale of 0-10? Why that number?
This opening question forces the reference to quantify their overall impression of the candidate. In practice, think twice about hiring anyone who isn’t a 9 or 10. (The exception: when a reference says they’re someone who “never gives anyone a 10.” Uh huh.)
Follow up on the “why” behind the number to uncover any hidden concerns or standout qualities. An agency owner once responded, “11. She’s amazing. If I had budget right now, we wouldn’t be talking, because I’d have hired her myself.”
How they answer matters, too. For instance, when I was a Director of Client Services, I asked a reference this question. They paused for a long time, and said, “7. No wait, 8.” When I asked them to elaborate, they seemed to be hiding something. We didn’t hire that candidate.
2. What was the biggest internal project they took on for you? How did it go?
This question gives you insight into the candidate’s ability to tackle large-scale challenges. Did they manage a significant operational overhaul, launch a new system, or fix problems with team structure? Dig into the details: Was the project completed on time? What impact did it have on the business?
Look for signs of problem-solving skills, project management expertise, and an ability to rally teams around a common goal. You also want someone to manage their boss’ expectations if something is off-track.
This also gives you a sense of their experience. I remember being stressed about printing 200 copies of a new booklet. My colleague Diane shared a perspective that reassured me… from her experience doing print runs of 100,000 copies.
2. What metrics did they focus on improving? How did they perform?
Strong operational leaders love metrics. Ask the reference what key performance indicators (KPIs) the candidate prioritized. Did they improve profitability, streamline processes, or increase team efficiency?
Odds are, your ideal COO is more numbers-oriented than you are. But you also want someone who understands that metrics aren’t just numbers—they’re tools to measure and drive success. If the candidate wasn’t metrics-focused, consider if that’s a mismatch.
At the same time, watch out for someone who always prioritizes numbers over people. That isn’t good, either.
3. How did they approach disagreeing with you on a plan?
Conflict is inevitable… but it’s how they handle it that matters. Did they propose alternatives when they disagreed with the owner? Or did they seem to blindly follow instructions, even if they had reservations?
The ideal COO should practice “intelligent disobedience”: respecting your authority but speaking up when they believe a decision might backfire.
I once spoke with a client’s VP of Operations, who seemed to have a morale problem. Turns out, it was partly the owner’s problem. The owner would come up with a new harebrained scheme, and the exhausted ops head just went along with it. Their comment to me: “So I suffer in silence.” Ouch.
4. Where are they on the “get consensus” versus “take action” continuum?
This is about their leadership style. Are they consensus-driven, preferring to involve the entire team in decision-making? Or are they more action-oriented, taking swift steps when time is of the essence?
Either approach can work—or cause problems. Your agency’s culture will drive which approach works best. If your team values collaboration, a consensus-oriented leader might be ideal. If you operate in a fast-paced environment, someone who leans toward decisive action may be a better fit.
5. What’s a time they had a significant issue with a direct report? What happened?
People management is a core responsibility for a COO. In some agencies, you might have them manage almost everyone (other than, perhaps, your sales and marketing team members).
Ask about a specific situation where the candidate had to address performance issues, resolve a conflict, or navigate a tough conversation with a direct report.
Pay attention to how they handled the situation. Did they balance empathy with accountability? Were they able to resolve the issue effectively? Or did things seem to continue to fester?
6. What was your favorite part about working with them? Your least favorite part?
This open-ended question allows the reference to share both strengths and areas for improvement.
Look for patterns. For example, if multiple references mention challenges around communication or follow-through, that might be a red flag. Or if everyone mentioned how the COO made work fun for the people around them—even during tough times—that’s a plus.
7. How do they approach delivering bad news to the team? What about delivering bad news to you as their manager?
COOs often have to deliver difficult news—whether it’s about budget cuts, missed goals, or organizational changes. Their approach to delivering bad news reveals their communication style and emotional intelligence (EQ).
Do they sugarcoat bad news, leaving room for ambiguity and hurt feelings? Or are they straightforward while offering a path forward? Their ability to deliver bad news well is critical for maintaining team morale and your trust as their leader.
They likely have also read books like Crucial Conversations, to finetune this skillset.
8. What did they do in the job that no one else could have done?
This question highlights their unique contributions. Did they develop a proprietary system? Implement a process that transformed operations? Cultivate relationships that were critical to the business?
Great COO candidates will have multiple examples. If their reference struggles to answer, it might indicate the candidate didn’t leave a lasting impact. Or if the candidate is coming from a much larger organization, they might not have experience “shipping” things… which isn’t a match for your agency.
9. What’s a time their work took longer than expected? What happened?
Even the best operational leaders encounter delays. The key is how they handle those situations. Did they communicate proactively and manage the boss’ expectations? Or did they try to sweep things under the rug?
This question can also shed light on their time management and problem-solving skills. If they’re not on top of their own schedule, they’ll struggle to keep you moving, too.
10. To be honest, our agency has high expectations for employees. Where might they need coaching while under pressure?
No one is perfect, and this question invites the reference to share potential weaknesses. Be specific about your agency’s high standards, so you get a realistic sense of whether the candidate can handle the demands of the role. I sometimes refer back to the old Peace Corp recruiting slogan: “The toughest job you’ll ever love.”
For example, if they struggle with delegation (especially if the team has sufficient Desire, Competence, and Capacity) or managing stress, consider whether that’s a dealbreaker. If someone is a Director of Operations, they’ll need more coaching than a seasoned COO.
11. What’s your sense of their long-term career goals? From what you’ve seen, is that realistic? What would they need to change to reach that goal?
Understanding a candidate’s career aspirations helps you assess alignment with your agency’s future. Are they happy to be a career COO, or do they want to keep moving up?
If they’re aiming for a CEO role in five years, will they be content in a COO position long enough to add value to your agency? Or is that a plus, if you want to step back or sell the agency?
A candid reference can also shed light on the candidate’s self-awareness and growth mindset. Our industry keeps changing, so your leaders need to find a balance: manage the present while preparing for the future.
Why these COO reference-check questions matter
Hiring a COO isn’t just about finding someone with the right resume. It’s about finding a partner who complements your leadership style, aligns with your agency’s culture, and has the skills to drive results.
These 12 questions are designed to give you a well-rounded view of the candidate’s capabilities, character, and fit for your agency. Don’t rush the reference-check process—it’s one of the most valuable steps in ensuring a successful hire. For even more on reference checking, check out Extreme Referencing.
But remember, no candidate is perfect. The goal is to understand their strengths and weaknesses so you can make an informed decision. The right COO won’t just help you run your agency; they can help you take it toward your long-term goals. And if you need help refining your vision and goals—before the new COO’s salary starts ticking—check out my Agency Growth Diagnostic.
QUESTION: What reference-check questions would you add to the list?
