What I Learned About Myself In a C-Suite Job

In exec life I discovered what I’m good at, what I’m not, what I like, what I don’t and what I fear.


Shane Kinkennon

3 years ago | 6 min read

Nothing illuminates strengths and weaknesses like a high-pressure role

Just over three years ago, I found myself in a C-level job unexpected in my grand career scheme. I had spent the previous 12 years as a home-based solo communications consultant and strategic-planning facilitator. I liked that life and had imagined finishing my career that way.

But a client CEO created an appealing new position and asked me to fill it. My ego was stroked, it sounded like an interesting challenge, and my spouse coincidentally had been itching for a change of scenery. So I thought, “Why the hell not?.”

Because I’d never imagined myself as a senior business leader, I had not spent time pondering what executive life might be like. I had been in consulting for most of my career so didn’t have much experience working “in house.” Certainly not working in-house in a senior-leader capacity, responsible for both people and results.

So no surprise, when the job began, the lessons came fast and furious. I learned a lot really quickly about how to run a complex business. I’m forever grateful for those lessons, which will useful for the rest of my career. But those lessons are for another article.

What was fascinating and humbling was what I learned about myself. Being thrust into a C-suite job without having done my time in a traditional training ground afforded me opportunities, at times jarring ones, to see more clearly what I’m good at, what I’m not, what I like, what I don’t, and what I fear.

For those folks who aspire to a senior-executive role, or work in one today, there are useful lessons in what I discovered.

1. I’m sadly prone to severe imposter syndrome.

I discovered that, even deep into my career with not-insignificant accomplishment under my belt, I’m still as quick as I was in my 20s to conclude that I’m not good enough.

Early in the job, without a shred of evidence, I became convinced that every one of my peers and most of the senior staff saw me as questionably qualified. It wasn’t true, I don’t think, but that didn’t really matter. My mental narrative was a runaway frieght train.

In time I shook off most of the imposter syndrome, compiling enough little wins to surrender in an “OK, I guess I’m fine” kind of way. Yet the learning was vivid. It appears easy for some accomplished people to feel like a big shot. For me, it’s easy to feel like a fraud.

Takeaway: Imposter syndrome plagues all manner of conscientious, successful people. If you’re prone to it, knowing it equips you to do something about it when it arises.

2. I have a high need to trust.

I discovered that if my success or fate is tied to other people, particularly when big things are on the line as they tend to be for senior leaders, I really, really need to trust those people. I need all us singing from the same songbook, I need rapport, and I need a measure of raw chemistry.

When those things are in place for me, I can move mountains. When they’re not, it’s hard to keep my heart in it. This need is a burdensome, unfortunate one because you don’t really get to choose most of your coworkers. They’re kind of like family in that way. Yet I’m hardwired with a need to be able to move about with my guard down.

Takeaway: Gallup’s 30+ years of employee-engagement surveys have found a direct link between “having a best friend at work” and the amount of effort employees expend on their job. And research shows that employees in high-trust organizations are more productive and energetic, they collaborate better, and they stay longer.

3. I really, really love the people part of leadership.

In my 12 years as a solo flyer, I bragged nonchalantly about “not having to deal with staff.” Turns out that assertion was absurd. When I became an executive, mentoring and coaching was quickly my favorite part of the job. I don’t mean being the boss — yuck.

I mean practicing servant leadership — doing my best to behave as though my purpose was to serve the people around me, not manage them. I discovered that I love helping people unlock their full potential.

So much so that I’m now making a career of it. When I left the C-suite job a few months ago, the hardest part was leaving behind those coaching and mentoring opportunities that meant so much to me.

Takeaway: To be strive to be a servant leader is really to have one’s heart filled. If you have the opportunity to lead, put yourself at the bottom of the pyramid, not the top. Let go any preoccupation with power or leverage. Think persuasion over coercion. The fulfillment you’ll experience is worth it.

4. I wildly underestimated the value of soft skills.

I happen to have standout soft skills. Yet I had long believed that they were little more than nice-to-haves, the kind of thing that enables you to get by on looks (so to speak) rather than substance. I believed technical skills were far more essential.

Yet I learned the higher you rise in the ranks, the more soft skills matter. When you’re senior in an organization and really lean into your soft skills, people respond in extraordinary ways. I was able to persuade and influence people to work in high concert to get crucial things done.

I could do so in a way that more technically minded leaders simply couldn’t. My boss called it “being the kind of person who people want to follow.” This was perhaps my greatest discovery of all.

Takeaway: Invest effort to hone your soft skills (things like communication, critical thinking, conflict resolution, and capacity to motivate). When you reach executive-leadership ranks, you’re guaranteed to be surrounded by equally smart, technically accomplished people. Your soft skills may be what sets you apart.

5. The transition from doer to exec is a real challenge.

Being a good executive means setting direction, interpreting strategy, clarifying priorities, situating your people to succeed, and getting out of the way.

Not rolling up your sleeves and doing the work. I learned that after working for so many years as a solo operator, I struggle to step back to let others do the work.

At times I gave in to the temptation “add value” in places where it wasn’t really needed, and I took on tasks that should have been delegated. It was the result of inner control freak at work, and it was the result of fear that I must produce something almost daily in order to earn my keep. It got better during my three years, but there’s more progress to be made. It’s something that executives everywhere, particularly newer ones, struggle with.

Takeaway: There is a cost when executives don’t let go of detail. Your role is to step up and back, not down and in.

6. I have a huge independent streak.

I learned that I really can’t help but to question authority. Not in a disrespectful or rude way — bosses tend to like me. I was a dutiful deputy, in fact. It’s more a case of my intrinsic desire to go my own way and act quickly.

Personality assessments rate me high on independence, enterprise, and creativity, and low on manageability. It’s a tough combo of traits to assimilate into a setting in which I’m required to follow direction set by someone else.

I learned that my independent streak may be even more pronounced now that I’m older and more confident in my instincts. Or maybe it makes me a great candidate for consulting, which is a key reason why I left that wonderful job and returned to that life.

Takeaway: Plenty of people are more than happy to follow a lead with little to no questioning. I’m not among them. It’s my duty to know that about myself and thus find professional situations (like my current solo gig) in which I have latitude to flex and adapt as I need to in order to feel whole, and to not torment leaders who are doing the best they can.

I don’t imagine I’ll ever return to another C-suite job. But I wouldn’t trade the experience or the skills gained for all the world. And what I learned about myself is worth its weight in gold.


This article was originally published August 29, 2020 in The Startup on Medium. It also is featured on


Created by

Shane Kinkennon

Certified Executive Coach. I work with CEOs of company up to $500M to help them get the most of their human capital and to lead change.







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