CEOs are people too

The Pink-Haired PM
Adventures in Tech
Published in
4 min readNov 22, 2022

Ok. Of course I know that CEOs are human beings. But, after decades of working to disrupt existing systems and find better ways of doing things, I realized that I’m often alienating the people I’m trying to impress by challenging them, rather than treating them as the humans they are. It’s not that I don’t see them as people, but, rather, that I see them as the establishment. But, if I want to get ahead, I’ve got to see them differently.

A woman wearing a suit holding a sign that says “Chief Executive Officer.”
Image by Gerd Altmann from Pixabay

I love people. I am told I am good with them. My ability to network and connect with people and make them feel good with my endless curiosity about their lives has served me well in my personal and professional life.

At the same time, Silicon Valley likes to disrupt, and, so do I. In my career, I’ve found a niche in helping organizations change the way they think about content. I look at their documents and processes with a critical eye. I get to know the personalities that cause the current systems to work the way they do. And, I methodically challenge and change this and work to create new and better processes and tools.

But now I’m reaching a point in my career where I am creating the systems that others challenge. I don’t see all the nuance that the people on the ground do. I rely on them to tell it to me. Fortunately, as a person who likes to disrupt, I appreciate when someone helps me see where we can disrupt a process I created. This might make me a good leader, but, ultimately, I won’t go anywhere in my career if I can’t get along with other people at the top. And, it occurred to me, what if someone starts acting towards me the way I’ve been acting towards leaders. I cringe at the thought. And, that’s not good.

Put another way, even if I am excellent at my job, if I am unpleasant, I probably won’t be around for long. Thus, I need to be both good at my job and reasonably pleasant. As a people person, I hope I can do better than “reasonably pleasant!”

I realized that it is time to change my approach. It probably isn’t helpful to my career to challenge the new CEO (or SVP or other senior role) on every decision they make. I don’t think I’d like it much if someone who worked for me provided mostly negative feedback and criticism of everything I did. I’d respect it, maybe, but it would get old. This approach doesn’t do much to build relationships with these people either. And, up until recently, I’ve been a little scared to approach people in these roles at all.

So how does a person who likes to disrupt, who is critical of leadership (and a little scared) do better? Well, it turns out, I have to see leaders and treat them as human beings.

Dr. John Gottman, arguably the world’s leading expert on what makes relationships work, says that for a relationship to be healthy, you need to have 5:1 positive to negative interactions (Gottman source). While we aren’t talking about a romantic relationship, this is a good rule of thumb for maintaining a positive relationship with any human. If all my interactions with a CEO or other leaders are negative, and few interactions are positive (for example, 1:6 positive to negative interactions), I am probably not going to have a good relationship with them. Thus they may not want to be around me, and I probably won’t get to sit with them at their executive leadership meetings.

I’ve gotten pretty good at connecting with individual contributors to be effective at my job. There’s almost nothing I enjoy more than making someone feel comfortable and turning them into a friend. So why haven’t I been replicating this success with the people at the top? Because I forgot to see the CEO as a human with thoughts, feelings, emotions, and insecurities, just like me.

So, I am trying something new. What if I started to get to know this person? What if I found out their passion and tried to connect with them on that? How can I genuinely notice and champion positive things the CEO has done? I don’t have to be fake. I can choose to see and say positive things more often.

I can also be curious. Who is this person in the leadership position? What are their thoughts, feelings, and struggles? How did they learn to do the job of a CEO? Ask questions without judgement. I find that being curious almost always helps and creates a positive outcome. And, bonus! I might learn something, too.

Most CEOs at small- to mid-size companies say they are willing to meet with individual contributors (open door policy, anyone?). And, if the CEO is out of reach, I bet there’s another leader you can build a relationship with.

So, the path forward for me is to see people in leadership positions as the people they are. Yes, they may represent or be the establishment. But, what’s stopping me from being their friend? Me. What’s stopping me from treating them with the human kindness I’d like to be treated with? Me.

I need to get out of my own way and work towards accepting people at the top as humans. We all want to be treated with kindness, respect, and as the professionals we are. People often surprise me, why not a CEO?

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