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.  According to the author, throughout his career, he has 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.
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.
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.