What are the most Difficult Conversations in your Startup?

The conversation with my team members about their separation is one of the hardest things for me.

Anju Aggarwal
4 min readJul 20, 2022


Photo by Tim Gouw on Unsplash

Many people, including myself, dread doing it.
I get cold feet by thinking about it.
At that moment, my job looked like the hardest thing in the world.
Many times, I even prayed that the world would stop, so I would not have to deal with this task.

What is it?

The task is letting your team members go or asking your team members to part ways with your company.

Fortunately, I am not the only one with such a reaction to this specific task.

Last year, I met a friend. He has been an entrepreneur for the past six years. He narrated an incident where he had hired an intern. He gave him three months to learn on the job with some low-priority tasks and a few professional training.

But even after three months, he could not finish the task within the desired timelines. Eventually, my friend decided to let go of this internship. He planned to discuss this matter with him the next day.

Surprisingly, the intern did not turn up at the office that day. Instead, he sent a resignation email the following day. My friend mentioned that he felt relieved seeing his resignation email as he had trouble approaching him on this subject.

I was surprised that even after six long years, my friend still finds such conversations uncomfortable.

Last week I was caught up in a similar situation. I had been working with an intern for a couple of weeks. Unfortunately, he could not deliver things on time, primarily due to his prior college commitments.

It became clear to me that this person is having a hard time juggling between his college work and my project work. The delay from his side started impacting my product launch timelines as I needed to launch my MVP (Minimum Viable Product) soon.

This is why I needed to have this difficult conversation with the intern about parting our ways. I was feeling guilty for asking him to leave as he was just a young college student who had not yet seen the cold and emotionless corporate world. Hence, I did not want him to feel bad and take this thing to his heart.

I discussed this issue with another entrepreneur friend. She tried to explain that I was doing this for my startup and not for some personal reasons.
Even after her valuable advice, I still felt reluctant to approach this subject.

But, I could not delay this conversation any further and asked him for a meeting. I explained to him the entire situation about our product deadlines and expectations.

Surprisingly, he handled this situation well. He stated that he had been facing a lot of challenges in managing his work commitment along with his studies. As a result, he was thinking of cutting down on his work commitments for some months.

This incident again proved the simple truth. Sometimes we make a mountain out of tiny things in our minds, whereas those things are much more straightforward and accessible in reality.

“Think Too Much!

And you will create a problem that was not even there in the first place.”

Ultimately, we both wanted to do the same thing, i.e., end the work contract. However, I was afraid to address this subject due to my imaginary thoughts.
Finally, we both wished each other for the future. We agreed to work together soon when the situation gets favorable for us.

I have worked in corporate for close to 20 years. The topic of terminating employees is a common thing in corporates. I have seen this situation from both sides — from an employer as well as the employee side.

Nowadays, we read many LinkedIn stories where an employer lays off their team over a Zoom call or via a mass email.

I find it very strange that some entrepreneurs can let their employees go in such a heartless and cold manner. In my case, I had to convince myself and muster enough courage to let go of even one intern itself.

I don’t want to be judgmental about what is right or wrong here.
But for me, the conversation with my employees about their separation is one of the hardest things to do.

However, unlike my other articles, I do not have any best practices or lessons learned to share this time.

My only advice to myself and other entrepreneurs would be to behave respectfully and to be compassionate with your employees during these times.

You might not need your employees’ services for one reason or another. In most cases, your employee is on the receiving end during this situation. They need to look for another job. Their personal lives might also get disturbed due to this change.

Whereas from the employer’s perspective, it is usually their decision for the separation, and most of the time, they had already put up a backup plan for the parting employee’s replacement.

So the disturbance for the company is less as compared to the transitioning employee.

“Even if a conversation is difficult, We must still be — Loving, Gentle, Decent, Moral, Honorable, Virtuous and Full of Integrity”

Also, you never know when you might cross paths with the same person in the future. So give your employees enough reasons to remember you with a good memory rather than a bitter one.

Wishing you a good week and hope you create good memories this week

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Anju Aggarwal

Founder, https://speakho.co - It helps you speak better English by catching all your mispronunciations so that you can talk confidently and be easily understood