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The Leadership Gap CEOs Don’t See Until It’s Too Late

Mitch McWilliams
September 16, 2026

The launch went great. Sales did their job, the retailer was thrilled, we got the shelf space. Then three weeks in, we’re out of stock because no one flagged that the co-man couldn’t scale fast enough. I hired a COO so I wouldn’t be finding out about this stuff after it was already a problem.

That’s a version of a conversation we have regularly. The names and products change, but the shape doesn’t. A launch hits every individual milestone. Sales sells it. Product development ships it on time. Then the thing falls apart at the seam between functions nobody was watching, because everyone was heads down doing their own job well. 

Nearly a year into this particular hire, the CEO wasn’t questioning whether the COO was competent. He’d proven that already. What he was questioning was whether hiring him had actually solved the problem he thought it would solve. 

That CEO owns part of this too, and to his credit, he’d admit it if you asked him. He hired for operational experience and a clean track record. He never asked in the interview process how this person had handled a moment exactly like the one that just happened. Most CEOs don’t. The gap didn’t start with the COO. It started with a search that screened for competence and never tested for the things that actually mattered. 

The job description usually reads the way you’d expect. Strategic. Experienced. Strong operator. They’re real criteria, and most finalists in a well-run search meet all of them. That’s exactly the problem. If the same criteria determine who is shortlisted and who is ultimately hired, and the hire still doesn’t work out, then the process was never evaluating what really mattered. 

Here’s what the process missed. Supply chain and plant operations report to the COO directly. Sales usually reports to the CEO. Product development is split depending on the company, sometimes ops, sometimes its own function reporting up separately. So a COO’s real job isn’t managing three departments that answer to them. It’s getting functions that don’t answer to them to move in sync anyway. That’s a harder thing to screen for than anything on a job description, and it’s exactly what the call above exposed. Supply chain didn’t know the co-manufacturer’s capacity limits until it was too late. Sales didn’t know to ask. Product development hit its date and considered its job done. 

CEOs describe this differently depending on how frustrated they are that week. Sometimes it’s, “I still have to catch things myself.” Sometimes it’s simpler: “I hired someone so I could stop doing this.” Either way, it’s the same complaint underneath. They didn’t hire someone to be good at their job. They hired someone to make a set of problems go away, and the problems are still showing up on their desk. 

Interviews miss this a lot. Typically, they reward someone who tells a clean story about supply chain, sales alignment, and product timelines. What they don’t reveal is whether that person has actually stood in the middle of those three groups and forced them to reconcile before a launch went out the door. 

The way to find that out is to ask different questions. Ask them to walk through a launch that went sideways and listen for where they place themselves in the story. A leader who was in the room for the miss, who can point to exactly where the breakdown happened and what they changed afterward, is a different hire than someone describing it from a distance, like it happened to their team rather than something they were accountable for. 

It also shows up in how a candidate talks about functions they don’t own. Ask a COO candidate how they’d handle a sales team overselling a launch timeline product development can’t hit. If the honest answer is “that’s not really my lane,” that’s useful. It’s also the kind of thing a resume will never tell you. 

The CEO on that call didn’t need a more talented COO. He needed one who saw the seam between supply chain and sales as his problem before the stockout made it everyone’s problem. He also needed a search process built to uncover that before the offer went out, not a year into the hire. 

CEOs aren’t looking for a collection of functional experts who each run their own piece of the business well. They need a leadership team that anticipates what’s coming, sees where one function’s decisions will affect another, and addresses those gaps before they become company-wide problems. When that happens at the top, it sets the tone for the rest of the organization too: communicate earlier, think beyond your own lane, and solve problems together. 

That kind of alignment doesn’t happen by accident. It starts with identifying executives who already think that way and making sure the search process is designed to find them.

 

For businesses evaluating leadership needs or preparing for an executive search, reach out to our team. We’d be glad to share what we’re seeing in the market and help you think through what the right leader needs to bring to your organization.

 

Meet The Author

Mitch McWilliams Team Photo

Mitch McWilliams

Mitch brings more than a decade of experience in executive search and an earlier 13-year career in engineering and operations at Harley-Davidson. This blend of technical and leadership experience gives him a strong understanding of how great people shape performance, culture, and growth. He partners closely with executives to build leadership and commercial teams that last and is known for his thoughtful, transparent approach and his ability to connect with people in a way that builds trust and clarity throughout the search process.

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