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Why are some executive leaders more successful than others?

I’ve been working with a software engineering firm that serves the Federal government.  They are very talented and have had a great track record of designing and implementing innovative tracking systems over the last ten years. But for the last six months, they are not doing well at all.  They lost two important clients and failed repeatedly to bring in new business. Even worse, they saw a handful of people depart the company, including a top executive leader, who left to go work for a competitor.

As a result of these circumstances, the firm was tense and frustrated.  They just keep doubling down on what they’d been doing, rather than being open to new possibilities.

“This can’t continue,” the leader of the company told me in one of our team leadership development sessions, standing at his window with his back turned to me, “or we’re going to die a slow and painful death.”

Louis (not his real name) was a French-born technologist in his mid-fifties.  Typically outgoing and boisterous, he was clearly changed.  When he turned around, I saw he had a hard look to his mouth and eyes.  I pointed out that he seemed miserable.

“We’d better be miserable!” he growled.  “We’re losers!”

“How could you be a loser?” I asked.  “You’ve had so much success here over the last ten years.  Surely two underperforming quarters don’t negate all the victories you’ve achieved.”

Louis sat down and covered his face with his hands.  I tried to help him understand that his identity and the identity of his team shouldn’t be bound up in their performance.  It should be bound up in their essence: who they are as people.  For example, Louis was a courageous innovator, someone who set a clear vision and rallied people to achieve it.  If he saw who he was in essence, and if his team could see who they were in essence, they would be able to relax about their circumstances.

“But I can’t relax with all this bad stuff happening!” he said.

“You can relax,” I encouraged him.  “First, it will help you to give up the idea that there are good circumstances and bad circumstances.  There just ARE circumstances.”

“Losing my top executive to a competitor?” he said.  “That’s not bad?”

“No,” I replied.  “It simply is.”

“Losing our two best customers?” he said.  “Not bad?  It simply is?”

“That’s right,” I said.  “And if you can learn to see everything as neutral, neither good nor bad, even your successes, it will give you the freedom to contemplate some new ideas and see opportunities that you haven’t been able to see.”

Louis took a deep breath.  His face softened, and I could see he was trying out this concept.

“Is this why some executives are more successful than others?” he asked.  “They don’t label things as good or bad?”

I said that was part of it.  They are also open to receiving new ideas.

“OK,” he said with a slight smile.  “And I think I know where the new ideas are going to come from.  We still have the most talented engineers in the industry – I’ll ask them.”


I agreed that this was a smart plan. To help him make these sessions as positive and productive as possible, I worked with Louis through my executive coaching program on how to have open and honest conversations, given that his team was likely to need to vent their frustrations at first.


Here are five tips that any leader in Louis’ situation would be wise to adopt:

  1. Listen, don’t talk – listening is the secret to becoming quiet and open as a leader.
  2. Ask questions – find out as much as you can about precisely what this situation is about; what do you have to learn here?
  3. Claim what you own – take responsibility for what you did, or did not do, to create these circumstances. Understand that you have some role in creating almost everything that happens to you and around you.
  4. Wonder – how can you benefit from the lessons you are learning?  How can you apply the lessons more broadly?
  5. Show genuine appreciation – let the team know how grateful you are that these circumstances brought some important lessons to light, that you will learn from them and get better as a result.

Being the kind of leader who is willing to overcome his own dense areas will help Louis drop his defensive, miserable posture and encourage others in the company to do the same.  While they may not immediately turn their circumstances around, that’s not the point.  The point is to be open and vulnerable, not closed and self-righteous, so that you can be the most successful leader you can be, regardless of the circumstances. Only then will you be truly free.

Are you faced with circumstances that have you feeling miserable? If you are open to expanding your possibilities, please consider calling for a coaching session. One conversation can get you pointed in the right direction.

If you’re not ready to call, I encourage you to download my white paper, “Curiosity,” which gives more insights to help you see through your blind spots and be a leader with a lighter heart.

To your success!


About Jack Skeen

Jack Skeen
Jack Skeen, founder of Skeen Leadership, has been coaching bright and successful leaders for close to two decades, spending thousands of hours addressing every imaginable leadership, business and life issue with wisdom and professionalism.

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