Letting Someone Go

This in my opinion is the hardest thing about running a business or being a leader in one.

Conversion issues? Operational inefficiencies? Company pivots? Send them my way.

Letting someone go is the hardest conversation you’ll have. The first time I did it, I threw up in a trash can immediately after. Now 10 years later - I have found it doesn’t get any easier.

I used to believe that if I wanted to be a seasoned entrepreneur, I’d have to get used to it. With time I’ve realised - it’s okay.

I don’t want to lose myself in the process and become desensitized.

Over the years, I’ve learned a few principles that help make these conversations less awful—for everyone involved. Not easy, not painless. Just… cleaner.

🧠 Do the prep work

Write down exactly why you’re making the decision. Be brutally honest with yourself. This is not a debate. This is a one-way communication. Prep helps you stay clear and grounded instead of rambling through guilt.

It also helps you ensure that you don’t back down if faced with resistance - it can be difficult if they have strong rebuttals and you forget your core reasons for letting them go.

🪓 Cut to the chase

Avoid the long, awkward lead-in. Don’t build up to it. Just start with:

“I’ve made the decision to let you go.”

Then explain the rationale. Clear > Comforting.

📋 Don’t linger

You just dropped a bomb. Don’t hover trying to patch it. That’s for you, not them. Say your piece. Be kind. Let them process privately.

The one exception here is when they aren’t shocked and ready for the conversation expecting a bit more feedback. Sometimes they’ll say, “I kinda saw this coming.” If they ask for feedback, offer it gently. But don’t coach mid-termination. That’s not the moment.

🔕 Don’t expect closure

Some folks may want a follow-up. Others may not. Respect that. Post-firing clarity is rare. If they want to talk later, let them come to you.

You’ll be tempted to get some sort of resolution. Don’t kid yourself. It’s not for them, it’s just to help you feel better.

🚪 Offboard quickly

Once the decision’s made, move fast. A long goodbye helps no one. Even if they offer to help wrap up projects—don’t. Close the loop. Exit clean.

If they are integral try and do the handover in a few hours and then move on. They won’t do their best work

😐 Don’t center your emotions

Don’t say “This is hard for me too.” That shifts the burden to them. Let them feel what they feel. Your job is to be steady, not to ask for comfort.

🤺 Talk facts, not character

Keep it about fit, skills, performance—not personality.

“The role requires X, and we haven’t seen enough progress toward that.”

Not: “You’re not good at X.”

📑 Be prepared with logistics

Don’t wing the admin. Have a tight script

• Final paycheck

• Severance (if any)

• Healthcare/benefits

• Equipment return

• Admin contact

🤝 Help where you can—within limits

If they ask for support and it’s doable (intro, LinkedIn blurb, reference)—help them. That five minutes of effort could change their trajectory.

Just don’t let kindness become a time sink or a one-sided obligation.

🧽 Bonus: Debrief for yourself

Afterwards, write a quick reflection:

• What signs did I miss?

• Was the role poorly defined?

• Did I delay this too long?

  This is where the real learning happens.

TL;DR: Letting someone go sucks. You owe it to them to make it clear, respectful, and fast. You owe it to yourself to learn from it. And you owe it to your team to move forward cleanly.

Until next time,

Ajay

P.S if you’re on my team - you guys are all crushing it! ❤️ This is just top of mind after a recent experience that already happened. Just in case any of you are freaking out!