This Is Most Senior Leaders’ Single Biggest Weakness

Greetings friends!

I wish I had figured this one out while I was still serving as General Counsel of my S&P 500 company.

Looking back, it seems so obvious to me. But it wasn’t at the time. And that’s why I can say with confidence this is a weakness many senior leaders share.

I hope by raising this issue and discussing it openly, I encourage currently serving leaders to help themselves become even stronger in their roles.

So now you’re wondering, “What’s the big issue, James?” It’s this:

Senior leaders have no obvious mentors within their companies

Senior leaders such as C-suite executives are in lonely roles. There is no one inside the company who understands all the issues that they face. And worse, they have little incentive to seek help from within.

I’ll use my experience as General Counsel to illustrate.

The General Counsel cannot discuss many senior management and board-related topics with other legal team members, even senior ones. Confidentiality forbids. And until a person has held the responsibility themselves, they simply don’t feel the weight of it the same way.

Other senior executives can no doubt relate. The chief financial officer or head of human resources have similar responsibilities they bear alone. But just as we won’t understand the scope of the CFO’s role and the intricacies of their concerns, so they do not understand ours.

Our boss is probably in the best position to understand our challenges. But do we really want to air uncertainties, stress, and frustration to our boss? We do not. So, we keep those thoughts to ourselves.

Interestingly, although the reverse is not the case, our boss can get sympathy from us. Every CEO who has felt the urge to vent their frustration at the latest board outrage will find the General Counsel to be most understanding.

Generic sympathy is nice, but not substantively helpful

We can and do have ways to find a sympathetic ear.

General Counsel probably have friends, maybe even people who mentored us along the way, with whom we feel comfortable airing our frustrations. And periodically letting off steam can be helpful.

Such people can give us generic advice about generic situations. They can also give us advice about managing our emotions and our expectations. We should be grateful for every assistance we get.

But the relief is temporary, and anyway is a far cry from providing substantive aid. As in, “I’m facing a really tough decision. Let me tell you what I think and why I’m leaning this way. What are your impressions? What would you do if you were in my shoes?”

The solution is to talk to someone who knows exactly what you’re feeling

Now some of you may be thinking, “That’s why I go to industry meetings. The C-Suite club puts me next to other senior leaders for precisely this reason.”

I used to think that as well. While those industry groups can be great, the interactions are fleeting and infrequent and everyone you meet is just as frantically busy as you are. In a day or two, they go back to their job, you go back to yours, and that was that.

No, what you want is someone who has not only walked a mile in your shoes but has time to focus on your issues. And you want them when you need them, and as much as you need them.

Yes, I’m referring to an executive coach. But not just any coach. You want as a coach a senior leader who knows from first-hand experience exactly what it feels like to make the decisions you’re making. So a former CFO coach for CFOs, a former Head of HR for HR heads, and a former General Counsel for GCs.

Talking with someone who can provide substantive advice as well as emotional support is immensely powerful. Now instead of having to make critical decisions completely alone, you have a sounding board to help you work through the process.

It’s obviously so helpful. Why don’t more senior leaders use executive coaches? Why didn’t I do it?

I can think of three reasons:

1. It never occurs to us to seek out such a coach;
2. We don’t know they exist or where to find them; and
3. We’re embarrassed to ask for help.

For smart people, senior leaders can be remarkably stubborn

Let’s face it. No one makes it to the seniormost levels of leadership without healthy doses of independence, masochism, and competence.

You get used to doing things yourself (independence). Sometimes that means great effort and sacrifice because the situation demands it (masochism). And you wouldn’t keep advancing if you weren’t very good at it (competence).

Unfortunately, all three factors mean it rarely occurs to a senior leader that seeking tailored help is even an option.

Executive coaches who specialize in C-suite roles are rare

Executive coaches are plentiful. Chances are, as a senior leader you’ve recommended coaching more than once in connection with someone’s development.

But coaches who focus on helping C-suite executives are rare. And those who were themselves C-suite executives even more so.

To conclude, there’s a final reason senior leaders might not seek out coaching even upon acknowledging it could be hugely beneficial to them.

Senior leaders don’t like to show weakness

Remember the independent, competent, but masochistic executive? There we go again. This reflects itself in our sometimes refusing to take simple steps to improve our lives.

I believe we can break out of this mindset. Ask yourself what you’d recommend to a colleague who wants to develop. Would you look down on them for taking advantage of the best resources on offer?

Of course not. If anything, you’d consider a person foolish for letting their pride or indifference hold back their career.

Don’t handicap your chance of being the best executive you can be.

Be well.

I published a version of this article in the ACC Docket, the global magazine for the Association of Corporate Counsel. If you liked this piece, I encourage you to read more.