CEO Coaching: The Five Reasons You’ll Fail

Many newer CEOs have contacted me during the pandemic, seeking answers about how to succeed in the role. They’re a bit lonely and frightened. Their questions and statements, however, are often phrased like, “How do I keep my job?” or “I want to avoid making big mistakes right out of the gate” or “I don’t want to fail!”

Many sources say “do this” or “do that” to be successful as a leader. Some advice is good, some theoretical and some off base. As you probably know, successful leaders come with various skills, personalities and psychological profiles. Although my experience tells me that some behaviors and activities are more successful than others, there isn’t one way.

I have, however, watched leaders fail over my long career as an executive and executive coach. In response to the “How do I keep my job?” questions, I offer the following reasons that you’ll fail if you aren’t diligent.

1. Poor relationships. You must be good at them. Developing and fostering healthy relationships with your board, employees and customers is key. Don’t think about being manipulative; think about being genuine. You won’t get everyone to love you — and that’s not only OK but also means you’re making the tough decisions. You should, however, strive to build relationships (whether you’re superior or subordinate in the food chain) that are based on trust, shared values, honest communication and appreciation. A word of caution … When you get to the big seat, you won’t hear the truth very often, because others want to please you. Over time, you’ll become blind to it and start breathing your own exhaust. That will cause you to fail. Make sure the relationships are “real!”

2. Weak or missing leadership skills. Just because you were promoted to CEO doesn’t mean you have all the leadership skills to succeed. And, per my warning above, few people will tell you what you’re missing or where you’re misguided. Have someone (e.g., a coach) get feedback about your strengths and weaknesses so you can eliminate fatal flaws and continually work to get better. Many years ago, when I first got my pilot’s license, the examiner shook my hand and said, “Congratulations, you now have a license to learn.” If you don’t get to a high level of leadership capability, you’ll eventually fail. Keep learning!

3. Misunderstanding/weak strategy. Just like being a CEO doesn’t infer great leadership skills, it also doesn’t mean you have a great grasp of what strategy is, how to craft it and whether yours is good. Strategic thinking isn’t a birthright — it’s a series of actions that must take place. Many CEOs don’t get this, and if they’re on a profitable trajectory, they might be OK for a few years. When things don’t go right, they won’t know what to do. Better to learn the skills before you need them, or you’ll fail!

4. Poor management skills. If leaders drive change, managers tame complexity. They make the trains run on time. If you’re a CEO, you need both skill sets! If you’re a whizbang entrepreneur who creates great ideas and aren’t interested in learning to lead and manage, sell your company and do it again. Don’t stick around and drive everyone nuts and likely diminish your equity. If you don’t have management skills to go with the leadership skills, you need to find the perfect COO, but most likely you’ll fail. The trains have to mostly run on time!

5. Lack of courage. Scott Galloway, author of “The Algebra of Happiness,” says “serendipity is a function of courage.” He’s right. Most of the “lucky” people I know failed many times. Train yourself to think of failure as learning; a coach can help here as well. Humility is  critical for a good leader — and you have to be confident to get back up after falling and say, “Well, that was interesting!” It’s natural to be afraid, but without some level of courage, you’ll fail. You have to be afraid and do it anyway!

Now that you know why you might fail, make sure you don’t!

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