021. [Founder Psychology Lesson] How to evolve from cowboy to leader

Founders might feel attacked by this one

Introducing a new series, Founder Psychology Lessons! For each edition, I'll deep-dive on one mental and human challenges of being a startup founder. Check out the first lesson below, and lmk what you think! 

I’ve been thinking about founder psychology and human dynamics of startups for a long time. But it’s especially top of mind these days, since as the Founder/CEO of Workflow, my job is to support early-stage CEOs, as well as the teams/cultures they’re building.  

There’s no shortage of advice out there for startup founders, but much of it tends to be focused on Productivity! Performance! Extreme Calendaring/Time Hacks! Which can be useful, sure – but my personal approach takes a different angle:

Being a startup founder means personal growth on (activate monster truck voice here) extreme hard mode. The internal work is the key to truly scaling yourself, and often the biggest challenge that can make or break the company.

There are so many angles I can cover, but we're kicking off this series with an extremely founder development challenge - the transition from hyper-independent wunderkind to a mature organizational leader.

Cowboy → Leader 

If “drive” and “ability to grind” were a sport, then startup founders would be Olympic athletes. But in a classic case of “What got you here won’t get you there,” the exact set of skills and traits that allow them to take a company from 0 to 1, are the exact things that start causing problems. 

After Product-Market Fit, the job of a venture-backed founder is to grow an organization. But the speed through which founders have learned to operate during the early stages, leads to major breakdowns when the team is getting built out. They need to learn to lead their team rather than jumping into the trenches with them. When a founder is used to yee-hawing it at 8000 mph, they will struggle to truly work with their team, rather than swooping in to do things themselves.

True collaboration involves training/documenting, building processes, asking people why things happened, and taking the time to gather input on various perspectives/constraints/opinions. And the power of their position makes it very difficult for founders to receive honest feedback from their team unless they’re explicitly carving out the space for it.  

What it looks like

This is the breakdown I see too often: A founder, struggling to adjust their execution in the context of a newly-forming team around them, starts to get frustrated and disparaging. They start to see their employees as “not being able to handle it” or “just not good enough.” The real problem is the assumption that their employees are exactly the same as them – weirdos who can thrive in a structureless environment – when most employees, even the very best ones, require some structure to work within.

And when managers blame employees for this problem instead of recognizing their own leadership gap – externalizing their own problems – they become resentful of the people they have power over. This starts a toxic spiral that’s very difficult to break out of. Defensiveness is never a good look, but especially for those at the top of the chain. 

Why does it happen?

Oof, so many reasons. Our industry’s collective consciousness doesn’t really understand the nuances of startup psychology, power dynamics, and great People practices. (I’m working on it! Tell your friends to subscribe to this newsletter!!) Pretty much all founders have to overcome this hurdle, yet there are so few meaningful support systems or accessible solutions. (Do not get me started on the proliferation of ineffective startup executive coaches and useless VC platform services. That's a whole other post I need to write 🙃)

If you're successful as a startup founder, there will come a moment when you have to rapidly transition from being a builder yourself, to primarily being a manager of builders. And this is not a pretty task. Transitioning from IC to a manager is difficult for anyone – much less doing it in an environment where everything is changing and somehow you’re in charge of everyone.

In this phase, so many leaders get caught by surprise and end up making lots of People mistakes. And People mistakes have a way of sticking around for a long time, even as you try your best to clean them up. This isn’t like Sales or Engineering, where the worst case scenario means throwing some work out and starting from scratch. People problems create painful, expensive holes that you’ll have to dig out of. Software doesn’t remember your mistakes, but people do. And they will probably hold them against you 😬

And even if you as a leader are doing everything right, employees themselves could be contributing to the difficult dynamic. Frequently, employees struggle to understand and internalize the extremely unique social contract that is working at a startup. Most people simply don’t have that level of ambiguity tolerance and resilience when they come in the door, though they can learn – through the environment that you, as a leader, can create! (I've written about that here.)

As a founder, you’re constantly thinking about the need to hit X goal by Y time to be able to raise Z round, so the company can survive – but if you’re not regularly telling employees this, then they won’t know! This sounds so painfully obvious, but it's a surprisingly common point of friction at startups I see. If you don’t tell your employees the why constantly, they’ll think that you’re micromanaging them, and/or you’re an asshole who’s cracking the whip. It’s a vicious cycle – it causes founders to feel alienated from their employees, and vice versa. 

How to overcome it

If this all sounds uncomfortably familiar, (feeling attacked? 😅) – it's all right, awareness is the first step to change. This is your plan from here on out: 1) empathize with your employees, and 2) communicate more effectively with your employees, so that they can empathize with you.

Founders carry a huge burden and risk in trying to get a business off the ground. All under immense pressure from investors and various stakeholders. But YOU are in the leadership role, so the burden of communicating this to employees is on you, as is the burden of understanding those employees. They say it’s lonely at the top, but that doesn’t mean you have to feel alone. Exercising mutual empathy is how you get to feeling like you’re truly a team. 

So in the rollercoaster that is startup life, try to be extra aware of ever taking things out on employees. “Why is X person so slow? Why can’t they run as fast as me? Why don’t they just do Y?” is generally not a productive line of thinking. Listen – if they could, they probably wouldn’t be working for you, they’d be starting their own companies! 

In these moments, step into your awareness and try to calm the f*ck down. (Literally. Take some deep breaths.)  Then, be honest about the ways you could be contributing to the problem, or the ways process/culture is still lacking. These do not have to be moral failings or anyone’s “fault,” but simply showing you the work that needs to be done. (And yes, this is what the Workflow team and I help startups with! 🤩)

Validate your own strengths as a superstar executor, AND recognize that this overused strength points to your next growth area: bringing others with you. And you might even end up surprised by how much of a difference that just a little bit of investment can make here, when you realize how much your team WANTS to run alongside you, they just need an on-ramp. That's the work of being a leader, and this is the job. Transitions are hard, but you've done way harder things. You got this.    

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Look out for future editions of Founder Psychology Lessons in the coming weeks! A preview of upcoming topics:

• "Let yourself be a human, not just your title"

• "The truth about executive hiring"

• “Give away your legos,” Founders’ Edition

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Also! Workflow has upcoming capacity for 1 more client, starting in end of February. If you’re a hypergrowth startup interested in benefitting from best-in-class Recruiting & People Ops temporary resourcing, let’s connect! 

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Jennifer Kim is the CEO/Founder of Workflow, an education and consulting company that trains the next generation of startup leaders on all things Recruiting, People Ops, and DEI. Through its flagship program, the HireEd Accelerator, Jen and her team have taught hundreds of startup leaders to make hiring a competitive advantage. Previously, Jen was Head of People at Lever and advised dozens of top startups. She is known for her hot takes on tech industry and culture as @jenistyping.