Why You Need Executive Coaching

Kevin Lee
Personal Development
Last Updated: 
November 5, 2020

“I can’t believe I’m spending a few hundred dollars per hour on this. I’m a pre-launch founder with no revenue. The last thing I should be spending money on is coaching.”

Moments before I joined the first video call session with my executive coach, these were the thoughts still racing through my mind.

We made some small talk and I commented on the great quality of his webcam. 

Anything to avoid talking about myself.

He cleared his throat and looked into my eyes. He asked his first question: 

“So what’s going on?”

My immigrant parents raised me the only way they knew - with the values their parents passed on to them.

  • Always push yourself harder: A test score of 99 was nothing to be proud of. It meant that I could have avoided the mistake that prevented me from reaching 100.
  • Express humility in every situation: When guests were invited for dinner, we would prepare a massive feast - enough to feed everyone for a week. Yet, when the guests arrived, my parents would apologize profusely for not preparing enough food. 
  • Anticipate needs: At the dinner table, I was constantly reminded to keep an eye on everyone’s tea cups and never let one go empty.

These cultural values have a time and place and they’ve served me well in life. I’ve never let myself grow complacent. I care deeply about others and appear to make friends easily.

When I left a career in tech to start a food company, I was ecstatic. I’d finally taken the leap of faith to set out on my own path. 

But a year into the startup, the cultural values I grew up with started backfiring.

I saw every single flaw in our product – flaws that most people wouldn’t even notice. 

I rationalized that being critical and pushing myself harder was a good thing. Founders should always be the biggest critic of their own product. 

At dinner tables with friends, I preemptively set low expectations: “Oh, you won’t like our food. It’s different from what you’re used to. You’ll probably hate it.” 

I thought to myself that humility would only help in the long run. Even the smallest dose of confidence in our product would erase any hunger to make it better.

I didn’t realize how fast these sabotaging voices were compounding. I was destroying my mental health with a thousand self inflicted cuts.

Instead of feeling proud of the fact that our company’s food enriched people’s health, I was losing confidence in the product, and in our upcoming launch.

I was frustrated all the time. And as much as I tried, I couldn’t break out of this funk. I needed help, so I decided to message an old acquaintance: a former founder and venture capitalist who told me over coffee a year ago that he was making a transition into executive coaching.

We exchanged a few brief messages and set up some time to chat.

“So what’s going on?”

I struggled to find the right answer.

I thought about the imposter syndrome I felt around owning marketing responsibilities when I had no professional marketing experience.

I thought about the anxiety I felt every day and how I felt a complete lack of control over any outcomes.

I thought about my insecurity around whether anyone would care about our launch.

These were all valid concerns that I’d lost sleep over. 

But the biggest thing on my mind that I was afraid to admit?

Deep down, I was afraid that people would hate the food product that we’d spent close to 18 painstaking months creating, day in and day out. 

And if people hated the product, then surely I’ve failed as a founder.

Before I could rationalize my way out of telling the truth, my instincts took over.

I told him how much I feared negative reception on our product. How each negative taste review from beta community members sent me deeper into a spiral in my own head. How I interpreted negative feedback as, “I’ve done a poor job. This is about me. I’m failing as a leader.”

He listened. And after letting me rant for awhile, he provided a piece of generative framing that has forever changed my mentality.

First, he labeled the ego in my way of thinking.

“As someone who is always pushing himself harder, you can always find more reasons why the product isn’t good enough, and therefore, why you are not good enough. But your job is not to get other people to like you. Your job is not to get people to like your product. Your job is to understand what needs people have and how to meet them. An interpretation of negative feedback is just that you haven’t quite met their needs yet. If you focus on the broader mission of meeting their needs, then everything along the way is not just about you, which is fundamentally about ego.” 

Something very powerful happens when an objective third party helps to reframe your mindset like this. 

Now, whenever I hear a piece of negative feedback about our product, I don’t feel like a personal failure. My confidence remains intact.

The old me might have sulked at a harsh piece of feedback. It likely ruined my day and slowed my work output to a trickle. 

The new me is excited. I’m working twice as hard to get this product into the hands of even more people. 

Some of them don't like it? Okay, that's fine. Instead of beating myself up, let's use this generative mindset to remind myself why I'm doing this.

“My job is to serve our users and meet their needs. My job is not to boost my own ego. I'm reminded of my commitment to serve these people and the broader community.”

The startup journey is first and foremost, a mental battle.

Coaching helps to develop a calloused mind so that you can survive and flourish. And to callous the mind, you need to go to the source of all your fears and insecurities. 

You need to understand how your cultural values hold you back. You need to label patterns of thinking when they are happening, so that you can stop the sabotaging voices before they start. You need to add generative frameworks to your mental toolbox.

David Goggins is a Navy SEAL and author who puts it best: 

"Under the hood, we all have huge reservoirs of potential and a ‘governor’ impeding us from reaching our maximum velocity. [The governor is] the software that delivers personalized feedback, in the form of pain and exhaustion, but also fear and insecurity, and it uses all of that to encourage us to stop before we risk it all. Our [governor] can’t stop us unless we buy into its bullsh*t and agree to quit. Once you know that to be true, it’s simply a matter of stretching your pain tolerance and letting go of your identity and all your self-limiting stories, so you can get to 60 percent, then 80 percent and beyond without giving up."

Despite all of my initial hesitations, I now consider these coaching sessions to be the most valuable use of my time. This is my $10,000 per hour work - my highest leverage activity.

I've changed my perspective entirely on coaching. It's not a cost. It's an investment.

The limit of any company is the capacity of its team. Investing to improve the capacity of your emotions and well-being increases your ability to perform and deliver better results. Whether you’re part of a 5 person company, or a 50,000 person company, you want to do the same thing: invest to make yourself and your team more capable.

Investing in yourself is the best investment you can make.

If you are interested in learning more, please feel free to DM me on Twitter. I’m happy to share a few coach recommendations and answer questions to help you in your own search.

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