How to fire someone without blindsiding them

A framework for letting people go fairly, starting from the job offer

The worst part about being a leader is having to fire someone.

It never gets easier. It always sucks. I’ve never walked away from letting someone go and thought “that was fine.”

The first time I had to fire someone, I couldn’t sleep for two nights leading up to it. I had delayed it for months because I was terrified. I liked the person, and I was worried about what would happen to their career. These feelings are natural for any human with empathy.

When I finally fired them, they were shocked. They genuinely thought they were doing a good job. It wasn’t fair that they were caught offguard, and it was 100% my fault.

The reality is, if you want to build a high-performing team, you must learn how to fire someone the right way. Even if you’re a really good interviewer, you’re only going to get it right some of the time. As Ryan Simonetti, President and CEO of Convene Hospitality Group, shared, “I still think hiring is the hardest thing. And even if you’re world-class, you’re probably only batting like .400.”

Phil Hernandez, CEO of Marketo, also shared the complexities of hiring and how getting it right 100% of the time is impossible:

This article covers the process I use to manage performance and remove the element of surprise. Following it won’t make firing easy or painless, but it will ensure the employee isn’t blindsided and boost your confidence as you navigate these difficult (and inevitable) conversations as a leader.

Table of contents

• The spectrum of firing

• Why people delay firing

• Step 1: Set expectations at the offer

• Step 2: The first 90 days

• Step 3: When performance slips

• Step 4: The second warning

• Step 5: The termination meeting

• It’s about fit, not failure

• What other CEOs say

The spectrum of firing

Not all firings are the same. There’s a spectrum, and understanding where your situation falls helps you choose the right approach.

Instant terminations

On one extreme are instant terminations. I once had someone send a derogatory email to the entire company at 2 am. They meant to send it to one person, but hit the company-wide distribution list. My head of people and I waited at the elevator door the next morning and let them go on the spot. I once had a sales rep game the commission system by buying the product on their credit card, canceling the card, and collecting huge commission checks for months. These situations require immediate action.

Mutual exits

On the other extreme are mutual exits. These typically involve long-tenured employees who have been with your company for years, but the company has outgrown them, or they’ve outgrown their own role. These people have given everything to your company. They deserve a different conversation, where you work together on a transition plan, potentially with higher severance and time to find their next opportunity.

Melanie Fellay, CEO of Spekit, on how some employees don’t grow at the same pace as the company:

Performance issues

Most cases fall in the middle of those extremes. In these situations, the person isn’t performing, and it’s not mutual, but it’s also not instantaneous. This is what the rest of this article focuses on. These are the people you know have potential but are not properly contributing and require some course correction.

Why people delay firing (and why you shouldn’t)

I’ve coached dozens of first-time managers and CEOs on how to fire someone, and almost all of them delay it just like I did early in my career. After seeing this time and time again, I’ve noticed some patterns in what holds them back. It always stems from these fears:

The first fear is purely of the conversation itself. You’ll lose sleep. You’ll feel sick. This fear is natural, and honestly, it never fully goes away. But you can’t let it paralyze you.

The second is fear of backfilling. “This person isn’t the best, but they’re keeping the seat warm. If I fire them, who’s going to do the work?” The reality is that a mediocre person in the seat is worse than an empty seat. They’re preventing you from finding someone great, and they’re dragging down everyone around them.

The third is personal. Maybe you hired a friend, or you’ve worked with this person for years and genuinely like them. You’re wondering: will they hate me? Will this end our friendship? This is real, but your job as a manager is to do what’s best for the team, even when it’s hard.

The fourth is worrying about the team’s reaction. I’ve worked with CEOs who are terrified that every single firing will make the entire company think layoffs are happening or that firing a team leader will undercut morale. But your team is smarter than that, and they probably already know this person isn’t performing.

The fifth is questioning yourself. “Do I have enough reason to fire them?” If you’re asking yourself this question, you already know the answer.

All of these fears are real. But delaying only makes the situation worse for you, for the person, and for your team.

Step 1: Set expectations at the offer

The firing process doesn’t start when someone’s performance slips. It starts the moment you give them the job offer.

The hiring manager should make the offer call. Not HR or the recruiter. This is a critical moment in the manager-employee relationship. During this call, I always start by identifying 2-3 “yellow” flags that came up during the interview process.

Here’s an example: “We really enjoyed our meetings with you. However, when we circled up as a team, there were two things we were concerned about. First, you’ve never worked at a company this size, and even though you said you’re ready to get your hands dirty, you’ve always had a large team supporting you. Second, you’ve never marketed to our target audience. Marketing to CMOs is very different from marketing to SREs. That said, we think you’ll overcome those things. If you do, we’re sure you’ll crush it. So with that, we’d love to have you join the company.”

I’ve never interviewed someone where everything was perfect. There’s always something. Maybe they haven’t managed a team before, they’re switching industries, or they’ve only worked at big companies. By naming these concerns upfront, you’re setting expectations from day one. The person knows you’ll be watching these areas, and if they can’t overcome them, they won’t be successful.

I’ve had people tell me years later, “I remember the three things you brought up in that call. I was so scared I wouldn’t get the job. I hope I proved you wrong.”

Step 2: The first 90 days

On the new hire’s first day, schedule a formal 90-day check-in. Tell them clearly: “By day 90, we expect you to be performing and contributing. If there are any issues, we want to address them early.”

Leading up to this check-in, give informal feedback in every one-on-one. Share what you’re observing, give feedback on their first projects, and ask how they’re doing. Are they surprised by anything? Do they feel like they’re getting a sense of the product, market, and customer?

The 90-day check-in should be formal. Give feedback verbally and in writing. This is your system of record, and it’s a forcing function. Everyone is working towards this date.

The new hire is asking themselves: Do I even like this job? Is this what I expected? Do I feel like I’m contributing? And the manager is asking themselves: Is this person doing the job we hired them to do? Are they showing any of the yellow flags we identified in the interview process? Are they on a good trajectory? Am I happy I hired them?

I’ve had a couple of situations where both the person and I agreed at the 90-day mark that it wasn’t a good fit, and we mutually parted ways. It doesn’t happen often, but it’s an important checkpoint.

I once had a head of people who literally wanted us to be like Facebook with unlimited perks, massive budgets, all of it. At 90 days, I said, “We’re not Facebook. We’re never going to be Facebook.” We agreed to part ways. I gave her a three-month severance even though she’d only been there a short time, and she left almost immediately.

By setting expectations at the offer and conducting a formal performance check-in at 90 days, you accomplish two critical things: you immediately correct hiring mistakes and set long-term expectations that you can leverage and revisit on an ongoing basis.

Step 3: When performance slips

Someone’s performance can start to slip at any point. It could be a few months in, a year, or 5 years. You could have someone who was crushing it for years, and one day they stop performing. If performance issues last for about a month, you need to give written feedback. This is where most managers fail. Their feedback is usually too informal, too late, or not specific enough.

Instead, write an email. Start by acknowledging what they’ve achieved recently, then reiterate that you want them to succeed. This is genuinely true. Replacing someone is painful, expensive, and time-consuming, so every manager would prefer the person in the seat to turn it around.

Then, list the specific areas where they need to improve, and for each one, include three things:

1. What needs to improve and why it’s important

2. A specific example of how they’ve underperformed

3. Exactly what I want to see instead

Here’s an example:

“When you joined, we talked about the importance of learning the product. To be successful in your role, it’s critical that you can speak to customers as a true expert. What I noticed is that you haven’t been investing the time to learn the product, and the last time I saw you do a demo, it was clear that you were just reading off a script, and the customer could tell. I want you to spend the time necessary to learn the product like the back of your hand. Then, you’ll do a mock call with me where I’ll act as the customer and ask questions, push you to go to areas of the product you currently don’t know, and essentially create an environment where you won’t be able to use a script.”

The end of the message says: “It’s critical that you improve on these things in the next couple of weeks. If you have any questions, concerns, or don’t agree with any of this, please let me know.”

Before sending it, verbally walk them through the email in a one-on-one. I read it to them so they know exactly what I’m about to send. As soon as you finish the meeting, hit send.

This is such an important tactic. There’s zero question about what was said, and the process of writing down the feedback gives you time to think about what you’re going to say, and how. And now the feedback has been clearly shared with the employee: it’s written down, been shared verbally, and they’ve had a chance to ask questions.

Some people get this feedback and turn it around completely. In my experience, it’s about 10-15% of people. But when it happens, it’s magical. I’ve seen some employees who read that feedback and immediately become the best at their function.

I’ve had others who receive it, and the next day, they’re doing the exact same thing I asked them not to. Other people opt out at this point because they feel the expectations are unfair, or don’t want to improve in those areas, and just quit.

Step 4: The second warning

If they don’t improve within a couple of weeks, you repeat the same process. Same format, but this time the tone is much more serious, and you should loop in your HR team or head of people.

Reference the previous message and the date you sent it. Make it crystal clear: “At this point, if you don’t improve on these things, we will have to let you go.”

The timeline here is measured in days, not weeks. Usually, at this point, people won’t quit; they’ll wait to be fired and hope for severance.

Here’s what I’ve learned from doing this many times: if someone is good and wants to change, they’ll take the feedback and do it after the first warning. If they don’t, it doesn’t matter how many times you tell them. They’re not going to change the fifth time if they didn’t change after the first.

Step 5: The termination meeting

If they still haven’t improved, it’s time for a termination meeting.

Include the employee, someone from HR (or another witness if you don’t have HR), and come prepared with all of the separation paperwork. Have a standard severance based on level and tenure. This avoids negotiation and ensures consistency.

Keep the meeting short. Refer to the previous messages and warnings, and acknowledge that you wanted them to succeed, but it’s clear this isn’t a good fit. Communicate that their skills and way of working will be a better fit at another company where they can thrive.

Don’t debate it. Don’t say sorry. Don’t negotiate. They might be emotional (for good reason), but you’ve made your decision and you know what’s best for the company and for them. I’ve had people walk in, sign the paperwork, and leave without any conversation because they already knew it was coming.

It’s about fit, not failure

I’ve fired people who went on to do amazing things. They became founders, leaders at other companies, made more money, and found roles they loved.

I have countless examples of this, including a CMO who was great at vision and strategy but wasn’t the strongest at execution. This is fine at a larger company with big teams and budgets, but not for a scrappy startup.

I had a customer support rep who truly cared about helping people solve problems. He was great at talking with customers, but he wasn’t good with technical products or complex issues. He was better suited to work on a less technical product.

The list goes on.

The point is: the reason for firing someone is not always that they suck. It’s often that for this company, this stage, this product, this part of their career, it’s just not a good fit. Remember that the next time you feel the fear of firing holding you back.

When you follow this framework for firing someone, you’ve given them the blueprint to succeed. If they can’t or won’t, then you’re giving them the opportunity to find a place where they will thrive.

Building a strong team is extremely hard, and it starts with your hiring process. Check out our guide on building a hiring system that works.

What other CEOs say

Promote from within
Ryan Simonetti, Co-Founder and CEO of Convene, states that hiring remains his biggest challenge, estimating a 40% success rate and particularly struggling with external executive hires. Despite using structured assessments in hiring, he notes it often takes 6-12 months to truly evaluate an executive’s impact due to the complexity of horizontal influence and cultural assimilation.

Hire for can-do attitude
Flint Lane, Founder and CEO of Major League Table Tennis, emphasizes that a 70–80% success rate in hiring is realistic and that no one has a perfect track record. He prioritizes candidates with a demonstrated “can-do” attitude and relevant past success in the specific function being hired for. Lane assesses this through questions about difficult projects, both successful and failed, to understand mindset and resilience.

Teams are orchestras
Phil Fernandez, Co-Founder and CEO of Marketo, views hiring as assembling a complementary team rather than filling static roles, emphasizing adaptability and synergy over rigid models. He believes hiring is inherently complex, combining skills, organizational behavior, and interpersonal dynamics, making a success rate above 60% unrealistic.

Backchannel leaders 360 degrees
Nick Mehta, CEO of Gainsight, describes his executive hiring success rate as low and emphasizes evaluating a candidate’s ability to manage up, down, across, and out. He uses in-depth backchannel referencing, including inquiries into both promoters and detractors, to assess leadership impact across stakeholders.

Scaling leaders is hard
Melanie Fellay, Co-Founder and CEO of Spekit, discusses the challenges of executive hiring, citing a 50% success rate and the difficulty of scaling early leaders as company needs evolve. She highlights the risk of hiring based on desperation, overvaluing industry experience, and underestimating the importance of self-awareness and operating style fit. Successful hires at Spekit often lacked conventional credentials but aligned well with company needs and her own hands-on leadership style.