Tech Leader Pro podcast 10, Handling someone quitting your team

Published on 2021-06-19 by John Collins. Socials: YouTube - X - Spotify - Amazon Music - Apple Podcast



As a leader, at some point in your career, someone will quit on you. This is inevitable, so you need to be ready to handle that process.

The first time this happens you may be upset, you may even be shocked. This is normal.

Over time, you will come to realize that people quit for many different reasons, as people are complex. Some of it may be your fault, and there are lessons here for you to learn from, but many of the reasons why people quit will be factors outside of your control.

As a Stoic, I will always advocate the acceptance of those factors that you cannot control. However, that does not mean that you should not have a process in place, in order to limit the impact on the remainder of your team.

In this episode, I will firstly look at some of the reasons why someone quits, the processes you should have in place for handling someone quitting, succession management, retention, and finally and most importantly, why you as a leader must remain positive throughout.

So let’s begin by looking at why people quit.

Reasons for quitting

There is an old adage that “people leave their managers, not their roles”. Sometimes that is true, and when someone leaves your team it is an opportunity to reflect on your approach to managing that team member, in case you done something wrong that you can learn from.

Naturally when someone says they want to leave, you need to speak with them immediately. Firstly if they are a great team member, you need to try to convince them to stay. If it becomes clear they are determined to leave, then you need to see why.

There are many reasons why someone decides to leave a role, some examples include:

  1. They are not happy with you, their manager, and they want to leave you. Try not to take this personally, it happens!
  2. They no longer believe in the company, or the vision.
  3. They are bored.
  4. They are having issues with other members of the team, and they want to get away from them.
  5. They were passed over for promotion.
  6. They got a better offer from someone else, actually in my experience in the software industry that is the most common reason.

Whatever the reason, you need to understand why this person decided to leave, in case there is something you can learn from in order to prevent others following them out the door.

Processes for handling someone quitting

The first thing to do when someone announces they are quitting is to talk to them. During that conversation, if it becomes clear that they are determined to leave and you cannot change their mind, then you must lead the conversation to what happens next.

Firstly, you need to agree on a finish date. In terms of remaining on friendly terms, you should allow the person to leave early if they choose to do so, for example if they have remaining annual leave days that they want to consume.

The reality is, the person has already left mentally once they announce their resignation officially, so there is no point in trying to drag things out on your side.

Once that date is agreed between both parties, and it is in-line with the employment contract, then you should ask the person to email your HR team that finish date, in order to make it official, and to enable them to prepare final payroll and so forth.

You will also need to announce to the rest of the team that the person is leaving: give plainly the reasons for their decision, without going into any personal details. It is best to be open here, in order to stay ahead of any rumours that might spread. Once its official, let everyone know right away.

Next up, you need to agree on a hand-over plan. The hand-over should be the primary activity of the person during their remaining time in your team, as there is no point in them continuing to work on projects. Instead, they need to transfer any knowledge they have on those projects to remaining team mates, via:

  1. Writing documentation.
  2. Giving demonstrations of the features they worked on.
  3. Walking people through the code they worked on.
  4. Recording videos explaining what they worked on.

Put simply, the hand-over is critical and needs to happen smoothly before the person leaves, as afterwards it is too late.

Succession management

As a leader, you need to look around your team periodically and ask yourself two important questions:

  1. Who are your most critical team members, namely those people who will hurt your team the most if they quit?
  2. For each of those people, do you have a back-up in place, namely someone who has the same set of skills and knowledge that could step in and take over if one of your critical people quit?

If the answer to the second question is no, then you need to start thinking about successor management. Engineers can think about this in terms of redundancy, or fail-over, where you ensure that you have at least two copies of mission-critical systems. You can think the same way about people: you need to have at least two people to cover each critical function in your term, not only in case one of them quits, but even for more mundane situations like vacations or illness.

The challenges with experts in your team with deep product knowledge is getting them to train their successor, without making it obvious. As a leader, you never want to communicate your anxiety to an individual that you are worried they might quit, but at the same time you need to have cover in place in case they do. Its a delicate balance.

In my experience, the best way to approach your experts is to tell them that you want them to train team mates in order to remove the burden on them, so that others within the team can cover them when they go on vacation for example. Its better to focus the conversation on the mundane situations, not the bad situations where they quit for good.

Fundamentally you do not want to be an exposed situation, where an irreplaceable expert leaves your team at short notice, and you have zero successor in place. That can really set back the rest of your team, and your project deliveries. It is your job as a leader to ensure a “plan B” is in place well ahead of time.


Naturally if we are going to talk about people quitting, we should also talk about retention, as prevention is better than cure. Just as the reasons why people quit are varied, the reasons why others stay is also varied.

In my experience, people stay in a company that they are emotionally invested in. They stay because they love the product, the people, or the overall company culture, and they have a strong sense of belonging to something great. If the company fails, they feel that they are failing and it hurts them deeply, so they do not want that to happen. People who are that invested in the success of the company tend to stay longer, and rarely leave due to money. For them, it’s personal. You should give these people as much ownership as possible.

People in the software industry have many options, and are rarely unemployed. I have had people leave my teams in the past because they were offered 20% more money to work elsewhere, so they simply followed the money. It is a bit mercenary, but you know I am perfectly fine with this: we all have bills to pay and mouths to feed. For such a person, the level of emotional investment in the company is not the same, for them its a simply transaction of their time and expertise for money, so retaining such people is usually a negotiation around money. For these mercenaries, you need to be wary of successor management.

Another big aspect affecting retention is you, the leader: if you are good at your job, some people will stay because they enjoy working with you. They may see you as a mentor that they can learn from, or simply someone who they enjoy spending time with. I have had team mates work with me in multiple companies in the past, and even follow me to different companies. This is very satisfying for a leader, when trust is that high that they value the relationship with you more highly than the company you both work for.

Fundamentally, there is only so much you can do with regards to retention. You can do all of the basics, like regular salary reviews and one-to-one check-in meetings, but the reality is when someone decides to leave, its just a matter of time before they move on.

Remaining positive

When someone decides to move on, the number one rule is that you must remain positive in your dealings with them. It is never personal, it is business. Depending on the cultural norms in your country, you should:

At such social gatherings, use the opportunity to publicly praise the person who is leaving, and thank them for their hard work while in your team. Highlight specific examples of features or projects that they worked on, to prove to them and the rest of the team that you really do pay close attention to their contributions. Show everyone that their work is really valued.

Finally, remember that person who is leaving will now act as an ambassador for your company, and more importantly you as a leader, with each new company they work for from that point forward. Its better to have them leaving happy and saying nice things about you, than bad-mouthing you in the wider industry. Offer them a great reference to help that good feeling blossom.

Aim to keep it friendly, or at the very worst, keep it civil.


Lets recap what we have covered today:

  1. People will quit your teams eventually. This is a normal part of being a manager, so you need to be ready for this and have a process in place to handle it.
  2. Some of it may be your fault, so you need to be honest with yourself about this: if someone quits because of you, there are lessons you can learn from it.
  3. Many times however, people quit due to factors outside of your control, so you just have to accept that it happens now and again.
  4. If they are a great team member, you should talk with them immediately and see if there is anything you can do to convince them to stay.
  5. If they are determined to leave however, then you need to understanding why they want to go. Typically there are a number of factors that fall into two broad categories:
    1. Push factors – things that they are not happy with in their current role, that are pushing them out emotionally.
    2. Pull factors – things that are appealing about the new role they have accepted elsewhere, that are pulling them out.
  6. Once the person quitting has formalized their resignation and a finish date has been agreed, you should remove the person from active projects and instead ask them to spend their remaining time on knowledge transfers, documentation, and other handover-related tasks.
  7. Successor management relates to the process of pre-emptively ensuring that you have some redundancy in your teams for key people, in case one of them quits in the future. You should aim to have at least two people covering each critical role.
  8. Another aspect that you need to look at is retention, namely building a culture in your teams that people are likely to enjoy enough to want to stay. In general, people will stay in a team where they are highly invested, and you as a leader need to encourage that investment as much as you can.
  9. Finally first and foremost, you must remain positive throughout this process. You want the person leaving to do so on positive terms, by wishing them well and offering them a reference. It is nothing personal, and does not have to be awkward in any way. Keep it friendly!

I hope you enjoyed this episode, and I look forward to covering the next topic in this series with you! In the interim if you want to follow me online, you can find my blog at, or follow me on Twitter @TechLeaderPro.

Thanks for your time, take care and have a great week!


File details: 20.3 MB MP3, 14 mins 05 secs duration.

Title music is "Still Cold" by Crystal Shards, licensed via


Apple Podcasts (iTunes)


Google Podcasts

Amazon Music

Main RSS feed


Five.Today is a highly-secure personal productivity application designed to help you to manage your priorities more effectively, by focusing on your five most important tasks you need to achieve each day.

Our goal is to help you to keep track of all your tasks, notes and journals in one beautifully simple place, which is highly secure via end-to-end encryption. Visit the URL Five.Today to sign up for free!