7 Regrets Even the Most Successful CEOs Have — and What You Can Learn From Them

Even the most successful CEOs can point to decisions they wish they’d made differently. What sets great leaders apart isn’t the absence of mistakes; it’s how they respond to them.

Throughout my career, I’ve noticed that the most effective leaders approach regret with humility, using it as a tool to improve their decision-making, sharpen their judgment and hone their leadership skills.

The following are some common leadership regrets and the ways great leaders learn from them to make better decisions.

1. Not being present

Many CEOs regret how they spend their time. When they are at work, they think about what they should be doing at home. At home, they think about work. As they juggle the demands of leading a business, they often find it difficult to carve out enough time with their loved ones.

Eventually, leaders learn that it matters most that they are fully present — whether they are with friends, family or in a business meeting. They strive to be intentional with their time and prioritize the things that matter most, both professionally and personally. Being a whole person allows them to show up as their best selves each day at home and at the office.

2. Getting stuck in the weeds

Many CEOs regret spending too much time working “in” the day-to-day details of the business instead of “on” business strategy that leads to more opportunities for growth.

The best leaders know that when they fixate on execution instead of delegating, they forfeit strategic work only they can do, such as scouting new opportunities, setting direction and developing top talent.

3. Not acting fast enough on people issues

Another recurring regret among CEOs is waiting too long to act on people issues. Even if it’s evident early on that an employee is not a right fit, leaders often take too long to do something about it.

This can put the organization’s operations and culture at risk. It can also jeopardize the credibility of the leader for failing to make a tough call.

The most successful CEOs make personnel decisions that align with their culture, even when it’s hard.

4. Making decisions in isolation

Ego can lead CEOs to think they need to make decisions on their own. But making decisions in isolation almost always ends in regret. The most strategic decision-makers create time and space for feedback — and not just from those who they know will agree with them. Hearing diverse perspectives from people who will challenge their ideas ultimately helps CEOs make decisions with confidence.

Leaders who join communities, whether it’s a peer advisory group or something less formal, have the opportunity to learn from peers who have walked in their shoes. As the business environment rapidly changes, it’s especially important to gather feedback from those on the frontlines with customers. That ensures the company can pivot quickly as customers’ needs evolve.

5. Avoiding risk altogether

The most common regret I hear from CEOs is about not taking a risk. CEOs regret what they didn’t do and the decisions they didn’t double down on. Rather than being paralyzed, high-performing CEOs recognize that there is often more than one right answer.

They move forward after a disciplined risk assessment: Do the homework, quantify the downside, set clear guardrails, and then act. Once a decision is made, they fully commit.

When CEOs take ownership, they’re going to find a way to turn it into a right decision. As long as there is a solid contingency plan in place, they know a bold move that fails is typically less damaging than making no move at all. And if they need to pivot, they look at it as a learning opportunity that will help the company adapt for the next big move.

6. Justifying decisions that don’t align with core values

Decisions that compromise organizational values erode company culture. It can be easy to align actions with core values when the business is doing well. But even when things get hard — or the tides change — the best leaders don’t abandon ship. They hold true to their values.

Great leaders align every decision to their organization’s mission, vision, purpose and values. This also means ensuring all the leaders on the executive team align their actions with the strategy.

7. Covering up mistakes

How CEOs act after a mistake often matters more than the mistake itself. Great CEOs know that owning decisions and accepting accountability preserves trust and enables faster course correction. They take responsibility by processing how they made the decision, evaluating the outcomes and analyzing the circumstances that surrounded the bad decision. When a mistake has been made, they focus less on justification and more on correction and accountability.

The best CEOs use regret to sharpen judgment and make better future decisions. That requires discipline: soliciting tough feedback, owning mistakes and turning failures into learning opportunities.

Leaders who do this consistently build stronger decision-making skills and, ultimately, better leadership performance.