When to Hire and Fire - Lessons from a Founder

Nothing is more destructive than working with the wrong people

My career in technology has stretched over 20 years, across 12 countries, operating in startups to large corporations and everything in between. I’ve served many roles including founder, CEO, group leader, hiring manager, producer, program manager, and marketer. This professional journey has been packed with tough challenges as much as it was blessed with unimaginable opportunities. Above all, it’s been a path rich in lessons. Occasionally, I’ll write about some of the things I’ve learned from my journey as an entrepreneur, tagged as ‘Lessons from a Founder’. My hope is that in sharing some personal experience, I may lighten the load of other brave builders.

---

Over the years, I’ve interviewed, hired, and coached hundreds of people. I’ve felt the pain of firing someone for underperformance or toxicity. I’ve known the devastating heartache of letting go of a team because the money ran out. What may seem like a mundane set of activities within an organization actually tends to be the most emotionally intense.

As a leader of a growing organization, hiring is one of the most important responsibilities you must bear. The decision you make by bringing someone onto your team will have some of most significant and long-lasting impact on your business. Why?

It’s About the People

At the end of the day, every business and organization is built by PEOPLE. Say what you will about AI automating all the jobs away, it will be a very long time before you can run a business without any humans. Not only are people your primary teammates, partners, and allies, they are also your customers.

In a traditional job, it’ll be your co-workers who you spend nearly 1/3 of your waking life with. It’s for good reason, they do a lot for your organization:

• Share the load and get the work done.

• Possess unique skills and ideas, leveraging their creativity and imagination to drive innovation.

• Provide perspective and judgement.

• Create culture—attracting, retaining, and motivating other talent.

• Represent your first customers, building and informing your product and services.

• Serve as ambassadors of your brand.

Where Hiring Goes Wrong

Over the years, I’ve made many hiring mistakes— bringing in wrong team members due to lack of due diligence and biases from close relationships. Over time, they became profound lessons in discernment.

Who you bring onto your team will affect your business in myriad ways.

Cost

Running a business is hard, and the primary way to drive it into the ground is spending more than you can make. Talent is most often one of the most expensive aspects of your business, tread carefully.

Complexity

Every person you add to your team compounds the lines of communication between people, generally represented as the formula: L = n(n-1)/2

L = total lines of communication and n = number of people in the organization. This table illustrates how this progression quickly escalates:

When you’re busy managing internal relationships, getting people on the same page, cleaning up misunderstandings, establishing and maintaining processes—you’re not solving the real problems for your customers.

Alignment

The Principal Agent Problem is a mental model that depicts the conflict of interest that arises when a business owner (the Principal) delegates a responsibility to an employee (the Agent). In a nutshell—because everyone has competing self-interests, it’s difficult to ensure that your team members are always working in your best interest.

This problem compounds the more people you add to the organization, creating a complex web of personal motivations and power dynamics. It’s no longer about the mission, it’s about who wins their own personal battle. We often experience this phenomena as ‘office politics’.

Culture

Culture is what fuels the best organizations— creating fertile ground for trust, innovation, and collective energy. Culture can only be created by people, a byproduct of consistent behavior. If you bring in people that lack a grounded sense of morality, model a poor work ethic, or skew towards unhelpful negativity—that energy will spread like a plague through your team.

Lessons Learned

• Understand your needs, problems, and gaps extremely well. Don’t rush to hire until you know exactly what you are hiring for.

• Don’t hire until you absolutely have to. If you can do the job yourself, simplify it, automate it, outsource it, or deprecate it—do that first. Keeping your organization lean will save you money, time, and complexity in the long run.

• It’s hard to find good talent. Be patient and don’t settle for less than the best. You’re not just looking for skills, you’re seeking goal alignment, values, trustworthiness, and compatibility. Hiring someone needs to feel like a ‘fuck yes!’

• Do your research. Even a simple internet search can reveal a lot about a candidate’s history. History doesn’t repeat itself, but it often rhymes.

• Check your blind spots. We all have our unique perspectives and experiences, but it can never be universally comprehensive. Bring in other trusted partners who can help you sniff out the details that you might miss and are willing to challenge your assumptions.

• Set up a trial run when you can. A 3-month finite project can tell you so much more about a candidate than you can possibly glean in an interview—how they communicate, collaborate with others, get things done, adapt, or handle adversity. This also gives you a smoother exit opportunity in case it’s not working out.

• Communicate clearly. Know your standards, set expectations, consistently give constructive feedback, guide, support, and course correct.

• Don’t let fear stop you from having the tough conversations. Burying your head in the sand will only delay and compound suffering. You’ll discover that you have surprising strength in handling difficulty, your diplomacy will level up, and people often learn the most from healthy confrontation.

• When it’s not working, let go. Know your own limits and the limits of your team. Trying to force something that’s not a right fit can cause more damage to your organization than you can imagine. Make the decision to part ways and know that it often leads to better outcomes for all parties over time.

• The nature of work is changing. Tasks and specialities have become atomized and globally distributed, thanks to innovations in technology. Solopreneurs take on simultaneous fractional gigs as opposed to a single full time role. This trend may fit better with your needs depending on the type of work you need done. Leverage contractors and gig workers to your advantage and let things grow from there.

I hope these nuggets prove useful to you and your organization. Building a team is a beautiful thing. When done right, not only do you accomplish amazing things, but it feels like absolute magic.

There’s so much more to say on this topic. If you’d like to delve deeper feel free to leave a comment or shoot me a DM. I enjoy exchanging experiences and ideas.

Thanks for reading! If you like my creations, you can sub for free, upgrade, comment, or click the ❤️ or 🔄 button. It goes a long way. I appreciate you. 🙏

What I’m Doing This Week

Gratitude

I’m grateful to be surrounded by loving friends and family who have my back.

Lesson Learned

Don’t forget all the little miracles of the present moment hiding in plain sight.

Listening to

Feels Like by Gracie Abrams

Watching

I had fun guest-hosting on julie’s podcast, psycho-analyzing the curious drama driving dating shows. Check it out for a taste of future podcasts to come on Poets’ Corner.

Reading

Study Details Transformative Results from LA Guaranteed Basic Income Program

Self-care

Meditation, volleyball, ocean, cold plunge, stretching, swimming, hot baths, sauna, sunlight, deep tissue work, shockwave therapy, squats, reiki, float tank, HBOT