Why CEOs Need Brutal Honesty to Grow (and How to Get It)

Jan de Vries · 2026-11-10

Like everyone, CEOs have blind spots. But unlike everyone else, there’s no manager to point them out. No performance reviews. No development plans. Nobody taps you on the shoulder and says, “Hey, you could do better.” Honest feedback is incredibly hard to come by when you’re at the top. I’ve learned that there’s always more to learn and always someone with more experience to learn from. But in my own case, I was missing someone who could see what I couldn’t. And the higher you climb, the harder that person is to find. At board meetings, I’d hear the same refrain: “Everything is clear. Keep doing a great job.” It frustrated me. I didn’t feel like I was doing a great job. I knew I could do better. Turns out, I wasn’t alone. Nearly two-thirds of CEOs don’t get any outside leadership advice at all, but nearly all want it, according to a survey by Stanford and The Miles Group. Without feedback, bad calls go unchallenged and compound over years. When you’re at the top, few people are willing to challenge you. So if honest feedback doesn’t come naturally, you have to build a system that provides it. As founders and CEOs, we spend all our time tackling the company’s biggest challenges, so we naturally have strong views. That can make it hard to consider others’ perspectives. So when I recruited my next board member, I specifically looked for someone who wouldn’t back down until one of us had proved our point. ### How Friction Builds Better Businesses At first, I wondered if I’d made a mistake. Preparing for board meetings took longer and demanded more conviction. They often turned into lengthy arguments. Over time, though, I came to appreciate how much those challenges forced me to question my assumptions and think more critically about my decisions. Research from Stanford Graduate School of Business backs this up: constructive dissent helps teams make better decisions than teams where everyone always agrees. But for this to work, you have to be willing to be wrong. That’s why it’s crucial that the challenge comes from someone with relevant experience—someone whose opinion you genuinely respect. A less senior person might make the same argument, but they won’t have the same experience as a board member who’s been where you are. Mine had worked with a similar company and business model, so he knew better than I what was possible and offered solid, well-supported arguments that could convince me. > “The higher you go, the harder it is to find someone who will tell you the truth.” ### Four Qualities to Look for When Hiring a Board Member Who Will Argue Back - **Independent thinker**: They don’t follow the crowd or the most senior person in the room unless they genuinely believe it’s the right path. Research by psychologist Charlan Nemeth shows that genuine disagreement sparks more creative solutions, while playing devil’s advocate does no better than having no dissenter at all. So the right person disagrees only when they believe it matters—not just to show they can. - **Experience you respect**: It’s easy to dismiss advice from someone who’s never been in your shoes. So appoint someone you’re genuinely willing to listen to, even when they go against you. They need enough experience in your sector and with your business model to back their arguments. - **Challenges you from the start**: Hire the person who questions you before they even join the board: “Why do you need that? Why do I need that? What will happen when we disagree? How will we reach a final decision?” If they’re questioning your decisions before you make an offer, they’re proving they can do the job you require. - **Engages with the team**: If a board member only ever speaks to the CEO, they only see a small part of the company. Seek someone willing to spend time with your team, so they can see the dynamics and culture firsthand. After spending time working in our office, for instance, my board member gained a much clearer picture of the business—and could offer even sharper challenges. Building a system for honest feedback isn’t easy. It takes humility, patience, and a willingness to be uncomfortable. But if you want to grow as a leader, it’s the best investment you can make.