The Hardest Decision You'll Ever Make (And Why You Can't Avoid It)

That Shakespeare quote comes to mind often when I feel afraid to do something I know I need to do. Right now I’m preparing for the most important hire of my career—a Vice President of Growth. Building the right team in our business is the most important thing we do. Part of building the right team is letting people go.

If you're running a business, there is nothing more important than hiring and firing. Your business is a group of people. The better that group is, the better your business is. when it comes to letting someone go, here's the uncomfortable truth: if firing is easy for you, you're probably a sociopath. It has never, ever been easy for me.

The First Fire: A Baptism by Anxiety

I remember my first firing like it was yesterday. I'd never managed anyone before starting my property management business—I'd cut my teeth on management in my own company, having always been either self-employed or a 1099 contractor.

The employee in question was doing their best. They weren't malicious, weren't stealing time, weren't lying. They were genuinely trying. They just couldn't meet the standards the role required—in this case, they couldn't pass the real estate licensing exam that was essential for their position.

I lost sleep over it. I talked myself out of it repeatedly. I felt like I was betraying someone who had dedicated their time and talents to my business. The guilt was overwhelming.

The problem? I was struggling with codependency. I felt responsible for their livelihood and success. I convinced myself that firing them would harm them, when in reality, I was harming everyone—including them—by keeping them in a role where they couldn't succeed.

The Framework That Changed Everything

My business coach and accountability group finally helped me see what I couldn't see on my own. They gave me the framework I desperately needed (this clip from Moneyball is classic):

When you fire someone, you do this:

1. Ask them to meet with you (unscheduled)

2. Bring a witness with you to the conference room

3. State their name and say: "For business reasons, today is your last day working here. We really appreciate your contributions thus far, and we wish you the best going forward. [Witness name] will help you gather your things and you will be paid through today."

4. Stand up, shake their hand, look them in the eye, say thank you, and walk out

5. Never explain, justify, argue, or defend (don't JADE: Justify, Argue, Defend, Explain)

The Aha Moment

Here's what I discovered after that first firing: the reality is always far less terrifying than the stories we create in our minds. The anticipation, the guilt, the endless mental rehearsals—they were all worse than the actual conversation.

More importantly, I realized something crucial: if you keep someone in a role they're struggling with, you're actually being cruel to them. You're preventing them from finding opportunities where they can truly succeed and contribute.

The Ripple Effect of Inaction

If you're reading this and thinking "I know I need to let someone go, but I keep finding excuses," here's what you need to hear:

Stop. You're hurting yourself. You're hurting them. You're hurting your family. You're hurting the rest of your team members and you're hurting your clients and customers.

You can't hire the A-players you need if you're keeping C-players around. If you're convincing yourself that C-players will magically improve, or that you can't afford A-players, you're destined to run a mediocre business.

As one of my colleagues in the ASU MBA program once told me: "If I have to fire somebody, I either made a mistake when I hired them or I'm making a mistake when I'm firing them." That's complete ownership of outcomes.

The Always-Be-Hiring Mindset

Most of us don't have the luxury of being expert hirers. We don't have robust processes, clear role definitions, or the right support systems. That's why we should never stop interviewing. Never stop hiring.

It's way too late to wait for someone to quit or need to be fired before you start your hiring machine. Build a bench of talent you can call on when the need becomes urgent.

Two of my friends: Tony Cline (awesome PM coach) and Dylan Scroggins (awesome recruiter) sat down to talk about building teams in property management. The entire interview is great but watch 2-3 minutes right here at this clip about the importance of having “a bench” to enable you to terminate someone when you need to. It’s worth watching.

Your Next Step

If you know you need to fire someone but keep putting it off:

1. Write down a commitment to yourself with a deadline (or email me right now with your commitment, seriously!)

2. Reach out for support from trusted, intelligent people who've been there before

3. Write down when you'll do it and this simple statement: "Doing this will be beneficial to me, to them, to my team, to my clients, and to my family"

4. Let your obligation to all those stakeholders propel you forward

If you don't need to fire anyone right now:

• Adopt a policy of always hiring

• Build that bench of talent

• Read "Who" by Geoff Smart and Randy Street

• Work on the most important process your business has: the hiring process

Remember: What got you here won't get you there. Sometimes the most compassionate thing you can do is make the hard decision that frees everyone—including yourself—to pursue excellence.

How hard was your first fire? I'd love to hear your story—hit reply and share your experience with me.

Recent Posts That Generated Buzz:

You’re Going to Fail (gee thanks man)

Don’t Let The News Be Your Guardrail

Three Things I Love Dearly (my two boys and this country)

Update on the Plaid: I got nothing. No tickets, no racing, no flooring it off the line all the time. This section of the newsletter (yawn) is going into hibernation (for now).