Exits are hard. It does not matter whether it is your first one or your fiftieth. Losing people is the hardest part of this job and I have never found a version of it that stops being hard.

In the course of my career, I have run a lot of these exits. Three or four were ugly, and I could have handled them better. You always learn the hard way. 

It’s never an easy conversation. For example, we had a prodigy who was amazing in the first two years of their career and eventually couldn’t keep up. We had to take the hard call to part ways after they had spent over three years in the company. While we tried to make it as smooth as possible, it meant that an the individual would lose their whole identity, friend circle and safe space. The idea that the company decided to part ways when just a few quarters ago they were the top performers was shocking to them. 

I think about those more than I think about the good ones.

When it comes to exits, I can only speak for startups. I have not worked inside a large MNC and I am not going to pretend I know how any of this plays out there. I assume the principles remain the same. 

What a bad exit actually costs

While the idea of a dramatic exit sounds romantic, the world is much smaller. I am often reminded of an episode from Mad Men, where one of the leads choses to break the news that she is leaving the company after being treated poorly by her manager, someone she treats as her mentor. The tension is palpable, but it is done with more grace than one should afford her manager.  Mad Men - Peggy Leaves

For starters, the world is small

The reference that decides your next job is usually not one you listed. Hiring managers call somebody they already know at your old company, because that person will say things a listed referee will not. There are only so many hiring managers across funded startups in this country. Most of them have worked with each other, hired from each other, or sat on the same panels. Recruiters move every two or three years and take what they know with them. Founders have WhatsApp groups. A functional leader you may have never met is a first degree connection with someone you worked with for two years. 

An exit is always more nuanced than it seems

Exists are usually a mismatch of expectations, with the person outgrowing the company or vice versa. Unfortunately, the Rashomon effect is at play here – both sides leave with their own incomplete idea of what went wrong. Whatever you say about somebody afterwards has to fit into a sentence or two. So the version that travels is always cruder and less nuanced than what happened, and the crude version is the one that sticks. 

It is not a nice thing to do

We often forget that the people doing a job are… people. It is a personal relationship in a transactional environment, and we end up treating them as one-dimensional beings. Most burnt bridges are a result of  people processing the ending while it is still happening, saying things in that state that they would not say six months later. 

A working relationship is transactional, and I do not mean that coldly. A company exists to get somewhere and it needs particular people to get there. You can have been exactly the right person at one point and stop being the right person later, and most of the time that is all that has happened. Once you can see an exit that way, doing the right thing at the end stops being difficult.

What I tell people who are leaving

Tell your manager before you have decided. 
‍
Something along the lines of: “I have been restless for a while, I think I am going to start looking, I have nothing lined up and I am not giving you notice. I did not want to do this behind your back.” 

It gives your manager a real chance to fix whatever is wrong. It also gives them time to work it out with you. A manager who is scrambling tends to make the exit about themselves. And it changes what you are to each other afterwards. However, this only works in companies with high-trust cultures. I could do it at inFeedo because I had been there six and a half years and knew exactly who I was talking to. That is not most people's situation.

Ask yourself three questions: Would they be sorry to lose you? Have you actually watched this manager receive bad news in the room, and seen what they did with it. And if you are wrong about them, can you afford it? If you cannot answer all three, say nothing until you have signed something else. That is not dishonesty. It is a reasonable thing to do in a relationship where one side holds most of the cards.

What I tell the companies they are leaving

Companies hold a lot of power after the employee leaves. Not doing the right thing here does your employee a gross injustice. Here are some things you definitely should get right. 

Full and final settlement. One of my early mentors, Behram, then at Tata CLiQ, told me they processed full and final settlement on the same day as the exit. It sounded impossible when I heard it, but it is not. It needs finance and the people team to agree in advance on what is owed, instead of starting after the person has gone. We built it at inFeedo and we are working on it at Aftershoot.

Letters. The relieving letter and the experience letter decide somebody's next joining date. Sitting on them because a handover is unfinished uses a person's next job as leverage over their last one.

Reference checks. This one is the quietest and it reaches the furthest, which is why the circumstances of the exit matter. A bad last impression can have a lasting impact, irrespective of who’s fault it is. 

I am often amused by how there is an entire industry around hiring, with structured panels and employer branding and thirty-day onboarding plans, and almost none of it exists for the other end. A white space in a crowded HRMS market, perhaps?

With experience you learn that you need to have a process for ALL exits. It has to be calculative, objective and fair. While there can be exceptions once in a while, that cannot be the rule. A good litmus test is to count how many exceptions you have to make to your exit policy in the last six months – if it’s greater than 3, you need to change something. 

Where you must burn bridges 

No matter how difficult the exit was, you do not bad-mouth your people. The only exception is a clear ethical breach, not because they left at an inconvenient moment or were difficult in their last month.

Three days after somebody joined us, his previous founder messaged me to say the person had been fired over a POSH complaint, that they had not been able to make it official, and that he was telling us out of good will. He burned that bridge deliberately and he was right to.

The same exception runs the other way. Harassment, wage theft, discrimination, or being pushed to sign a resignation when what happened was a layoff. Walking away loudly from any of those is not burning a bridge, and nothing else in this piece should be read as a reason to stay quiet about them.

The most useful thing you can do as a founder is stop over-promising. Do not call your team your family. And do not demand loyalty. It is not important that somebody stays with you forever. You earn loyalty through what you actually do, and if somebody you love working with finds a better job, the right response is to bless them and mean it.

If you have spent two years telling somebody they are family, neither of you have an honest way to have the conversation when the role stops making sense. What should have been a slightly awkward conversation becomes a heated exchange about loyalty and betrayal.

Exits arrive at bad times, when the company is under pressure and nobody has slept, and knowing better is not much use on a day like that. What I have learned is to build the process so that it works when I am not at my best.

Remember – what makes an exit less painful is being objective about the decision and generous about the process.