How to Handle It When a Key Employee Wants to Leave

Few moments feel as unsettling as when a key employee says they want to leave, or worse, threatens to. For small and mid-sized businesses, losing one critical person can shake your entire operation, impact morale, and hit your bottom line hard.

In this episode, we share how to handle these situations with clarity and leadership. From spotting early warning signs to creating a culture where no one is irreplaceable, we talk through strategies that protect your business, your team, and your future.

We cover:

• Why you should never be surprised when someone wants to leave and how to stay ahead of it
• What to do when an employee “threatens” to leave as leverage
• Why letting go of a toxic high-performer may actually strengthen your team
• How quarterly check-ins reveal concerns before they become exits
• Ways to create win-win transitions where both the business and the employee benefit
• Why building a culture of delegation ensures long-term resilience

At some point, every employee relationship ends, but when you approach it as a leader, your business can come out stronger on the other side.

Want to grow your leadership skills and build a resilient business? Join our free Visionary Founders Club. A community for small and mid-sized business owners to connect, learn, and grow together. Click here to join.

“If a resignation surprises you, it’s on you as the leader.” – Anna Angelova

Transcript for “What to Do When a Key Employee Wants to Leave”

The transcript below was automatically generated. Please ignore any errors or inconsistencies in the text.

Anna Angelova   0:04
Guten tag, Joris, we get.

Jores Minasvand   0:07
When I’m talking now.
Hello from Hello from Austria.

Anna Angelova   0:11
OK.
Hello. Hello. Yeah, yeah, not really. Anyway, more than just task management. This is the podcast you’re.

Jores Minasvand   0:19
Mhm.
You speak more German than I do, so.

Anna Angelova   0:24
Yeah, I studied German for like 4-5 years, four years in high school. I remember a few things, but not a lot. So anyway, where were we? Oh, Tuesday.

Jores Minasvand   0:31
Oh, wow.

Anna Angelova   0:42
It is.
Montak is Monday. Donerstuck. Anyway, enough of German lessons. This is more than just task management, your favorite daily podcast where we help you build a thriving business and sometimes learn German or Spanish. And I’m Anna Angelova, co-host of this podcast and a business coach and consultant.

Jores Minasvand   0:47
Mhm.
Yeah.
Mhm.

Anna Angelova   1:04
And I have Joris Minestan here with me, my fellow co-host and business consultant who speaks Spanish, Armenian, Farti and English and and what else?

Jores Minasvand   1:18
There is on Norwegian.

Anna Angelova   1:19
Oh, Norwegian. I forgot Norwegian.
Yep, Yep. So that’s why sometimes you, as you listen to us and learn about building your business, you also learn some words in different languages. So where are we? Oh, Tuesday.

Jores Minasvand   1:36
Mhm.

Anna Angelova   1:40
We are talking about today. We are talking about.
Something that you might have faced or you might be facing or as a business owner who has a team, and this is when a key employee wants or threatens to leave. What do you do? Like how do you handle a situation like this? And this can be a really tough situation, right? Especially when?
When we talk about a small mid-size business, right? Like your team is probably not 10,000 people and because even when in a in a corporation when good people leave it, this they feel this like the team that the person was part of, they feel this. Yes, the overall impact might not be like there might not be.
That much of an overall impact on the bottom line when it comes to you running small or mid-sized business, a key employee leaving can really impact your bottom line. It can impact your whole business, the morale and everything so.
How you handle it, it’s really important.

Jores Minasvand   2:42
Hmm.
Agreed. Yeah.

Anna Angelova   2:48
And yeah, and and where it could, what I want to start with is that first and foremost, if this is a surprise to you that your employee wants to leave or threatens to leave, this is on you like this is on you as the manager.
As the leader of the team, because you should never be surprised when someone says I want to leave, I’m looking for something different. You should actually know as a leader, first and foremost as the leader of the team of the business.
You should have practices in place where you have this kind of actually proactive conversations with your team.
Where once every few months you even ask them what would make you leave. So if someone says I want to leave and or threatens to leave.
Then and you are surprised, then it’s on you. It’s on you 100%. Now if you know about this, like if you’re not surprised, if you were expecting it, then of course like you can manage this in a better way. But either way, whether you were were expecting it or not. So the the the idea is like what do you do when this happens?
And I would actually start with if someone threatens to leave, I I would cover this little bit first, because for me, when an employee threatens to leave, it points to something completely misaligned within the culture.
And within the within the team because like threatening to leave there, there’s something like it reveals something about this person as well. And letting this person go might be the best approach because like if they threaten you ultimately and when we say threaten, it’s like you know what?
What it is, right? Like when they ultimately, it’s like they hold your hand behind your back and like twist your hand and it’s like, oh, I’m so special and special and you need to increase my salary or give me more vacation days or or whatever or give me the title of something.
If they can’t force you right, unless you do something they would leave, then it actually reviews a lot about the character of this person. And my personal opinion is that letting go of this person is probably the best option. And yes, it it might hurt your bottom line.
In the beginning, it might be tough to find a new person or to train someone to take over, but one of the things when it comes to attitude is that attitude is kink and you need to remove bad apples as soon as possible.
Even if they are some of the best performing people on your team, so.
This is on the threatening part. Joris, I want to hear your thoughts.

Jores Minasvand   5:53
So I’ve seen so many of these and you’re right, this is the cancer. It will spread. The attitude will spread to others and soon all of your employees will be disgruntled and and they’ll hold you hostage. That kind of negotiation, that’s not even negotiation. Like you said, that’s hostage.
What you do is you immediately cut that off and teach everybody else a lesson. I have seen this. I have been in the situation where I’ve replaced these people. I walked in to replace these people temporarily until nobody.
Is irreplaceable. All of us can be replaced absolutely, positively. And if we think that that we’re we can’t be replaced, you’re wrong given the right time and money.
Everybody. And anyhow, like you said, maybe your revenue will dip for a short period, but it will come back up if it’s a healthy business. So that kind of threat, absolutely. But if they want to negotiate, there are ways to negotiate. We talked about this. We had another session a while back.
On having a path and a system where you can find leaders in your in your team and enable them and build them and all that. So same thing with as part of your.

Anna Angelova   7:12
Oh, yeah. In your team. Yes. Yeah. Yeah, absolutely.

Jores Minasvand   7:22
As part of your employee retention, you need to, like you said, you need to be in tune with the customer and sorry, with your workers. You need to know if they’re not happy. You need to know how to make them happy.
And again, some people, I just had a conversation today with a co-worker. He gave me an example. One of his team members was offered a 60% increase.
Our salary from another company.
Some people are just for money, especially if they’re young. In this case, again, there’s no negotiation because there’s no way for you to be able to increase the 60% because the other company has a different model. They have cash infusion to that’s how and and a lot of times the 60% is on temporary.
You will crash, the person will come back, but that’s a different story. But you can if you can negotiate, if the person is really good, if they’re not just for money, negotiate. If you can give them the 25, you work out in different, see what else there.
I’m happy leadership training, whatever it is, traveling, whatever it is, you try. But I think the best thing is for you to have systems in place where it doesn’t get to to the.
Point where your employees go out and put themselves out out there and get offers, especially for your core team.

Anna Angelova   9:05
Yeah, prevention is the best. Yeah, absolutely. Prevention is the best for your core team to.

Jores Minasvand   9:08
Yeah, sure.
Go ahead.

Anna Angelova   9:18
Yeah, it’s the best thing that where where you proactively help them grow and give them what they would they want. And it’s a relationship, it’s a partnership, right? Like you said, if they have a 60% offer from somewhere else increase on top of what they’re earning, you might not be able to do this. So and that’s OK.

Jores Minasvand   9:31
I understand.

Anna Angelova   9:38
And the other thing that I was thinking as you were sharing these things, though, is that at some point there is a time when people outgrow us, we outgrow them, right? Like there is a time when it’s just the end of the relationship, right? It’s just the end, like it’s not.

Jores Minasvand   9:38
Yeah.
Yeah.
M.

Anna Angelova   10:09
Employee and someone who you’ve nurtured, you’ve empowered, and you have that good culture. Ultimately, let them go, right? Let them go. And this is where you can structure a way for their exit, where they help with.
As much as possible with the transition, with the knowledge transfer, with even choosing their own replacement, right? And again, when you are proactive, you can know about this soon. You can know about this actually so well in advance where like here in in Canada.
And I think US is similar. We have what, two week notice like this is what we are supposed to give like a two week notice. But if you are proactive, if we’re proactive and you do this kind of check in with your team.

Jores Minasvand   10:56
Mhm.

Anna Angelova   11:02
Once a quarter, for example, you can know that something is going on and this person is starting to think about other options and you can actually help this person, your key employee, find their next step while they also help you with replacing them.

Jores Minasvand   11:25
Yes. And the other thing that you can do is, and a lot of time happens when leaders and business owners, they get busy with running the business, they don’t pay attention that an employee becomes irreplaceable. They get into a key position, whether it’s.
Quarters or with the passwords or finances or whatever it is. Stop this from happening and one of the things that.
We talked about culture, right? So from a culture perspective, from a leader’s perspective, what you can instill and you can tell your your team and your people is.
And and I say this myself and I practice this myself, I always am the most useless person in the in the team and if I’m replaced, nothing breaks and you should also have this culture.
In your team and useless doesn’t mean not productive. Useless is in in the in the meaning of if I get hit by the bus tomorrow, the work will continue. I’m not in the critical path. I’m not holding anything back or it’s like in a.
Where if you have kids and family and assets and stuff, not having a will is the same thing, right? So make sure your team is grown and nurtured in a culture where you keeping secrets.
Becoming indispensable is not job security.
Delegation and letting other people grow, letting teaching other people what you know, and then you go do better things. That’s a culture. That’s the culture that should be. And I’ve seen it so many places where people actually hold things.
Hostage just to make sure that the company will never get rid of them. Lo and behold, come Friday morning, they walk in. None of the personal stuff is on their desk, their ID’s locked. They can’t access computer.
HR walks in and says, well, guess what? We’re going to pull the plug before it’s too late. So if you can get your people to have that culture where they enable everybody else and they’re also.
Don’t think job security is in becoming indispensable. Then you have a good culture and you don’t have to worry about replacements, but it’s going to become a very positive cycle and then people won’t even leave.

Anna Angelova   14:14
The thing is that people, at some point people live, right? Like, yeah, it won’t be something that happens often, but you know that it is still like we all grow each other, right? What I remember though from what you were saying is that something that corporations do which you can also implement is.
Mandatory vacations, right? Where where you need to go on vacation at least for consecutive 5 days once a year, at least for consecutive 5 days. So someone else can take over what you’re doing and do these things.

Jores Minasvand   14:37
Mhm.
Yes.
Mhm.

Anna Angelova   14:51
And what this way you prevent what you were saying that like one person or is so ingrained and does everything that no one else knows what’s going on with this part of the business. But again, there’s a lot about like team management and leadership and I would highly encourage you if you haven’t joined our visual.
Visionary founder Scorpiet join it. We talk about this more there. There is there’s some resources and and of course like we have trainings on this as well to help you become a better leader, a visionary leader and founder. So highly recommend the link is in the comments, not comments.
Description of the episode. Check the Visionary Founders Club. Join it. It’s free and it pay to pay dividends for you and knowing how to lead your team and what to do when a key employee is about to leave.
It matters because when when you do it the right way, when you handle the situation as a leader, your team will benefit. Like Joris, like you said in the beginning, it might be that yes, your bottom line gets hurt or or something like this, productivity drops, but in the long term.
Things will get better and better. You get better and stronger, your team gets stronger, your business gets more resilient. So although your initial reaction might be a little bit of level one or two reaction with oh, why me or oh.
This person is an idiot. After all these years we were together and so on. Like step out of this, take a breath and go into. I love level 5 energy, the win win. It could go into win win thinking. How can you approach this situation?
In a way that the company wins, the person who is leaving wins, the new person who comes in wins and and everyone wins.

Jores Minasvand   16:55
Absolutely. Oh, again, back to the culture you lead, how you build your teams is how it will continue. So put a good basis in your company and and you will avoid these issues forever.

Anna Angelova   17:11
Yes, yeah, absolutely.
So I know we talked a lot today. Yesterday was a shorter episode. Today’s a little bit longer, but these conversations are important and you stepping up as your role as a leader, it’s so, so key for you to have a thriving business.
And we’ve probably just scratched the surface on the whole topic. So again, highly recommend join the Visionary Founders Club if you haven’t yet and come back tomorrow when we’ll be talking about simple way to manage your calendar.
Especially if you’re a solopreneur. Now this conversation, if you already have a team, it can still apply. There might still be some things, useful things for you there, so feel free to drop in and listen to the episode. If you are a solopreneur, this episode is definitely for you. How many you may.
If your calendar really shows.
What you’re focusing on. So come back tomorrow for another episode of More Than Just Task Management, your favorite daily podcast where we help you build a thriving business. Joris, thank you so much and we’ll be back tomorrow.

Jores Minasvand   18:24
Thanks for having me. Bye.

Anna Angelova   18:25
Bye.