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How Top Execs Solve Their Toughest Leadership Challenges

Leaders want counsel from someone who understands where they’re coming from, and who has the skill to push them to create real shift in their thinking.

a lighthouse overlooking the sea

I recently conducted a series of interviews with executives near the top of America’s corporate ladder. My goal was to find out where these execs turn for help when they can’t solve their hairiest leadership challenges on their own. My research revealed some interesting insights.

Right off the bat, I learned that senior leaders feel that there are very few people they can turn to for help. They don’t want to ask their boss. That feels too risky. They don’t really want to turn to their peers. That can be awkward. And of course, it feels weird to ask for help from a direct report – after all, the boss is supposed to know everything.

This lack of options leaves top executives feeling quite alone in the rarefied air of their companies’ upper ranks. Which is not great, because they really do need help sometimes. After all, getting the big promotion doesn’t mean that you automatically have all the answers.

And senior leaders want help. According to a recent Stanford Graduate School of Business poll of more than 200 CEOs, board directors and senior executives across the North American public and private sectors, nearly 100 percent responded that they appreciate receiving leadership advice. The only problem is, good advice is rarely easy to find. I learned that myself, sometimes the hard way, in my 20+ years as a CFO at Fortune 100 companies.

This leads us to the trusted confidant. Many of the execs I interviewed told me they’d prefer to receive advice from a person who knows how to keep their problems confidential. One CEO said, “I need someone to talk to. Someone to challenge my thinking. Someone to run ideas by without feeling like I’ll be compromised.” Many leaders have told me they know one or two people like that. A loyal peer, for example, or their life partner. A few of them mentioned a mentor or an executive coach.

But when it comes to a confidant, trustworthiness alone is not enough. Senior executives are results-driven folks, so when they get to the stage where they need help, they want serious support. As one Chief People Officer put it, “In the past, I’ve often gone to a confidant whose confidentiality and competency I trust. The problem is that it's rare to find someone who truly has both traits.”

As many of my executive coaching clients have confirmed, top leaders don’t want to expose themselves and their challenges to just anyone. And they’re certainly not just looking for a shoulder to cry on. They want someone who understands where they’re coming from, and who has the skill and fierce courage to push them hard enough to create shift. That is, shift in mindset. As Einstein once said, “We cannot solve our problems with the same level of thinking that created them.”

Throughout my interviews with these execs, I discovered that trusted, competent confidants come in two varieties. The first is the mentor. “Listen,” the mentor says, “I’ve faced this issue myself before. Here’s what you do…” In other words, the mentor advises from a place of experience and expertise. This is highly valuable, particularly when time is of the essence and the stakes are high. It’s a bit like applying a tourniquet to stop bleeding. In an emergency, the leader needs an immediate solution more than a new skill. The shortcoming of pure mentoring, though, is that it can be more like giving someone a fish than teaching them how to fish. It might solve the problem at hand, but it doesn’t always prepare that person to deal with problems down the road.

Interestingly enough, senior executives tend to have an intuitive sense about this. While virtually all the execs I interviewed mentioned that they’re open to outright advice under the right circumstances, especially from those with relevant expertise, what they want even more is a second type of confidant.

This second type of confidant is the coach. While most of the leaders I talked with didn’t use that label, as they talked about what they really want from a confidant, they were clearly describing the qualities of a coach.

Here’s what they said they want:

“It's less about having someone deliver a solution, but more about getting help calibrating my mindset. I need other perspectives. Not so much specific advice.” – Chief Product Officer

“I need some help reframing things and adjusting my lens. Being a sounding board, validating options, providing a safe place, allowing for vulnerability.” – Chief Procurement Officer

“What I need is someone to talk to, someone to challenge my thinking. Someone who knows the business but won't judge.” – Chief Executive Officer

“Some of the help I need is practical, and some of it is just emotional. Every once in a while, it's just to laugh about something, and let down the façade. It can be lonely when you are at the top.” – Senior Vice President, Strategy

“I find that my executive coach is very, very good. I like her openness, directness, and feedback. More on the EQ side more than the actual technical side.” – Chief Financial Officer

In other words, the coach doesn’t come right out and say, “Here’s what to do.” Instead, a coach works alongside the leader, creating a safe place for intellectual and emotional exploration, acting as a sounding board, providing feedback, challenging assumptions, and helping crack open new ways of thinking.

Here’s my challenge for you today: next time you need help solving a particularly tough leadership challenge, don’t try to go it alone. There’s too much at stake. And it’s unnecessary. Instead, reach out to competent people you trust, and ask for help. That’s one of the most courageous things you can do. And one of the smartest.

Who are your trusted, competent confidants? If you don’t have any, it’s time to find some. Those who have gone before you, peers, and, yes, executive coaches, are a great place to start.

When you connect with your own confidants, here’s what you’re likely to find:

  • A safe place to be vulnerable

  • Someone who will push you, hard

  • Access to your most creative, mind-blowing thinking

So, what big, hairy problem is vexing you today? Yeah, that’s a tough one. Now, go get some help with it!


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