Phasing Out an Employee Struggling to Assimilate into the Culture of the Company

Shubhada Hebbar

Director of Product Management at Roku



I hired somebody a while ago; initially, their resume looked great. We interviewed this person and pulled them in. At first, I was very happy. It was a difficult role to hire for, involving a lot of cross-functional work that required interpersonal skills, a devoted work ethic, and a sense of being proactively communicative.

This person was very smart. They had the background and knew how to handle their work, so that part was good. The part that was lacking was a certain dynamic aspect. They tended to work in a silo style.

Working in silo as a Product Manager is very challenging. Product Management is all about going to everybody and understanding how what they all do comes together. You need to make sure that you’re putting yourself there, talking about what you’re doing, yourself, and making sure that their roadmaps are all in alignment with what the company needs overall.

That part was really not happening. A lot of the Engineers were having trouble working with them. These peers expressed dissatisfaction in the fact that the employee was really not aware of any part of the Product pipeline aside from their own work involving it. The employee was setting requirements that concerned only what they saw, not even checking to see if the work had already been done. Something was off.

Actions taken

This person was on the neat and orderly end of the personality spectrum. They were genuinely nice, but these challenges with others became undeniable. I made an effort to try to mentor this person and to see if I would be able to do anything about their predicament. I really did not want to let this person go before they had been with us for an entire year at least; doing so would make finding their next role much more difficult. How could I make sure that a hasty move would not destroy this person’s career?

I put in a lot of time and effort. I sat down in the meetings that this person was having. I advised them to meet people every single day, to make lunch plans with a member of their team in order to get to know that person. The problem was that they were not doing their part to establish these relationships with their teammates and reports, which was what put distance between this person and others within the organization. I assured this person that they were more than capable of making this effort.

They still maintained this habit of staying cloistered at their desk, not extending themselves to others. They were not taking the initiative to talk to people, refusing to step outside of that comfort zone. Their natural tendency was to shy away from this type of social effort. It put me in a very tough position.

Every week, I would ask this person who they were meeting with on the team and what they talked about while sharing that time together. What did they get out of the meeting? My goal was to understand whether or not they were participating in this exercise actively. I resorted to training within the company; while they were attending the sessions, little was coming out of them.

Meanwhile, my work was piling up as a result of the time that this interest took away from my own responsibilities; my boss was getting frustrated with me. It had been a year, and, even after HR got involved, nothing was being done about it. There got to be a point where I had to give them an ultimatum: if they were not able to acclimate themselves to the culture of the company, there was no way that I would be able to keep them here with us. I had to let them go.

Lessons learned

  • While it is good to be an empathetic leader, I pushed it too much in this case. I wanted to see if I could help this person out, but I could not. In some sense, my own reputation suffered due to my association with this person. You should always try to mentor somebody on your team who is struggling, but if they are not receptive to the opportunities to learn and to grow that you are affording them, you cannot stretch it too long.
  • It is very important to make sure that you are hiring the right person right from the start.
  • You should not get overly emotional when dealing with an employee that does not respond to feedback. One individual should not be prioritized at the expense of everything else. When it is a lost cause, you need to let go.

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Shubhada Hebbar

Director of Product Management at Roku

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