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28 September 2021
Startup leaders: You’re probably lacking this critical skill
Unsplash © The Humantra

Startup leaders: You’re probably lacking this critical skill

In a recent issue of Teaching Startup (#68), I answered a question from a former corporate leader turned first-time entrepreneur about how to deal with the loss of a key employee for an indeterminate length of time for personal reasons.

I laid out an answer as best I could about replacing key functions and how early stage startups especially have to spread that risk of loss across all their resources. I also talked about separating the emotional response from the business response, but also clarifying that separating the emotional response doesn’t mean removing it.

In other words, if empathy isn’t in your arsenal of leadership skills, it’s time to get up to speed really quickly.

Don’t be Steve Jobs, because none of us are

The fact that this startup leader reached out for help in figuring out how to handle this situation is a sign that this person cares about that employee. And that’s an upset in my book, considering where this startup leader came from and how little experience they had running such a small organisation.

The traits I hate to see the most in startup leaders are the ones that are obviously learned from corporate leaders. Why? Because startups don’t have the room for error that large corporations have. If you lead your startup like you think Elon Musk or Mark Zuckerberg or God forbid Jack Welch would lead your startup, you’re going to kill your startup.

For example, I’ve met at least one first-time founder CEO who has like five employees and one of them is a personal assistant. It makes me want to scream.

On a more serious note, it’s a little-known fact that startup leaders need to care very much about every single person in their organisation. Most startup leaders I know are brilliant people, and they can be very good at vision, at tech, at finance, at deal-making, at networking.

But they suck at personal relationships.

Hey. Me too. No judgment here.

However, being cold and detached is not a requirement for startup success. Maybe it is when you’ve got tens of thousands of employees across five continents who ultimately report to you. But when your team is under 50 folks, you don’t have the luxury of being distant.

Why empathy is important

Unless you’re paying way more than market salary or everyone at your company has options that are about to mature into riches, you’re playing from behind. You have far less artillery than most of your competition and definitely less than the incumbents in your industry. You need every advantage you can get.

This includes your rapport with your employees. All of them.

When I was young and talented (as opposed to old and experienced), I didn’t think twice about walking away from a company that I didn’t think cared about me. Not that they didn’t give me the things I wanted or I thought I deserved. Not that they didn’t listen when I had what I thought were amazing ideas. Not that I got passed over for bumps and promotions for reasons I didn’t think were fair.

I mean, those sucked too, but those were things I could understand.

What really got me disengaged was when I was working for someone who didn’t seem to care about who I was, or what was important to me, or even what was going on in my life.

And yeah, that’s fine too. As a startup leader, you don’t have to be everybody’s best friend. And if you’re old like me, please don’t invite yourself out to happy hours or whatever it is the kids are doing on Friday afternoons.

But when it matters, you have to show up and care. Because if you don’t, you’ll not only lose that employee, you’ll lose everyone they hang with, talk to, or is in that private slack group that you’re not invited to.

You don’t have to break or bend rules for them. You don’t have to get behind their causes. You don’t have to put them on any sort of pedestal. But you DO have to make an attempt to understand who they are, what’s important to them, and what’s going on in their life.

To a certain extent. Please don’t pry.

The only way to learn empathy is to start showing it, and that takes guts. But if you wait for someone to suffer a personal or professional crisis before you try to hone that skill, you’re playing from behind.

This article was originally published on Medium by Joe Procopio

Joe Procopio is a multi-exit, multi-failure entrepreneur. He is the founder of startup advice project and is the Chief Product Officer of mobile vehicle care and maintenance startup Get Spiffy. You can read all his posts at