Bootstrapped Giants

Firing people doesn’t have to suck

Published 2 months ago • 5 min read

“Thank you for FINALLY doing it, Jesse.”

One of my top performers stopped by my desk with a relieved look on her face.

“What do you mean FINALLY?” I responded

“Well, Bob has been a toxic employee for almost 2 years and we all knew it. We figured you had your reasons for keeping him on and trusted you but it's hard not to feel a little lighter with him gone.”

I felt relieved but also… embarrassed.

Because I kept trying to accommodate Bob – despite his incompatibility with the role, our culture, and our values – my whole team suffered.

It was a shitty, unpleasant experience.

This (composite) example was how ALL of my firings went for the first 7 years of my entrepreneurial career. They were cumbersome, agonizing, and usually ended with lots of hurt people.

Even just moving someone around to a different job or department took months to decide and implement.

We entrepreneurs LOVE to talk about markets, ideas, products, $$ but the real job of entrepreneurship is PEOPLE.

And the hardest thing in PEOPLE is changing their jobs, especially if it means moving someone OUT of the organization.

I have good news: After years of working on this, today, when I let people go (or they quit) it's usually with a hug and lots of gratitude all around.

Not the BS kind. Real genuine appreciation. Sometimes, they even end up working for me at other jobs that they're more suited to.

How did I make the shift??

Insight 1: Get clear on what I want

When I was 26 years old I had no idea what I was doing. I didn’t know myself, my ideal company culture, or “my people” were. As a result, my hiring and expectations were all over the place.

When I hired an engineer, I expected him to architect, code, and even sell! Since I didn’t know my expectations, I (obviously) didn't communicate them.

I got lucky a lot, mostly by hiring people like me. Familiar backgrounds, schools, job histories, etc. It was easier for me to communicate and build trust with these people.

But without a clear vision for what I wanted from my team, it was SO hard for anyone to know if they were doing their job well or not.

And so of course when I switched their job or let them go, they were left wondering what they did wrong. There was frustration all around.

Today, I have a REALLY clear sense of what I’m looking for in people.

I’ve shared it many times: Entrepreneurial Rigor. That means equal parts Entrepreneurial Hustle – fast, creative, resourceful – and Analytical Rigor – quantitative, logical, and reflective.

I want people who care about others and about self. I like ownership and candor.

Not only do I have this at a high level in my organization, but I’m constantly being clear about my expectations for people on my team, whether it's for the next quarter or the next assignment. It's one of the most important things I do as a leader.

Insight 2: Alignment vs Certainty

The biggest unlock for me has been: Understanding that what I want and think is simply that… MY opinions. I DO NOT claim to be “right” about it. It's just “Jesse's way.”

Also, all my statements above are about ME, not about another person. They're the things I want, like, etc.

That difference may seem insignificant but it's a BIG shift.

For example, if someone I hired walked into a meeting and didn’t KNOW their numbers and presented without data, I immediately JUDGED them as an under-performer, not smart, and doing it the WRONG way.

So I’d jump into fix-it mode. I’d teach them why they were wrong, cajole, lecture, and maybe even yell in exasperation.

And guess what, it never really mattered and all it did was piss the other person off. No one likes feeling made wrong for something.

Today, if someone doesn’t use numbers and data… I don’t make them wrong, I don’t try to “fix” them. I can meet them where they are. I might ask “Do you want feedback?” or “Do you think numbers are important?” I can be curious to understand why they don’t align with my view (not who is right/wrong). I can also ask if they are aware of my expectations and why I believe they are important. 9/10 times… it's a teaching moment or a moment to align expectations. 1/10 times we both realize there just isn’t ALIGNMENT and that’s okay. In every case, no one leaves feeling hurt or upset.

This keeps me from falling into the pattern of blaming, correcting, arguing etc.

Of course, I share this feedback with the person, but when my heart is truly not trying to prove I'm right and not judging them, I come across as supportive and helpful.

Insight 3: Trust, Candor and Curiosity

I GENUINELY want anyone I work with to learn, grow, and thrive in their careers. That’s important to me and if you work with me, you can feel it.

That’s not what I used to want… I used to want them to do work, to build my company so I could have amazing success. People could feel that, too.

So when they experience my candor they also trust my intentions.

While I'm candid when someone's work isn't aligned with my vision, they know that I'm genuinely looking out for their success. And if a role isn't right, I want them to land in one that's more aligned with their needs.

Looking out for their alignment and success comes from genuine curiosity. When I say, "This role doesn't seem right for you. What do you think?" I'm not doing it to covertly nudge them out the door. People can feel that. I'm genuinely curious about their opinion.

With my heart in the right place and a lot of candor and curiosity, the answer for what to do with a misaligned team member usually becomes clear to both of us.

Sometimes it means letting them go to another company.

More often, the answer is that they need a few additional things from me or from the company to be successful. That’s easy.

Occasionally, a job shift within my organizations is what’s right.

How this looks in practice.

At GrowthAssistant, my staffing company, our first salesperson was a rare Swiss Army Knife type of person, but he seemed unproductive and uninterested in his work.

Instead of thinking that he was wrong for being unproductive, I expressed genuine curiosity.

When I asked why he seemed disengaged, his answer was clear: “I hate feeling like a used car salesman.” Even though he did the job, he hated sales! Yeesh. What a misalignment.

I asked him how he felt about helping our existing clients grow their businesses and adding value to them. HIS EYES LIT UP.

So we moved him quickly out of his sales role to a role more focused on client growth. Since then, our expansion revenues are up 25% and he's feeling happy and energized.

Of course, sometimes the right thing for the person is to shift outside the company. And that is okay too. It can be done in a respectful and patient way that supports everyone.

When done properly, past employees can become future business partners, customers, and friends.


PS - If you’re finding value or have questions from these emails, PLEASE reply and share feedback/questions with me. I read and respond to every email and hearing from people encourages me to keep going!

PPS - just hit reply and tell me about your business in one sentence.

Bootstrapped Giants

Jesse Pujji

Bootstrapped to an 8 figure exit @ampush. Now building a $1B+ bootstrapped venture studio @GatewayX and sharing everything I learn along the way.

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