Tough conversations, to be or not to be?

Anna Fiofilova
6 min readSep 26, 2018

For many years I have wondered why we are not good at having tough conversations in our company, at least according to our engagement surveys for the last six years. My random thought on this topic had lead me to nowhere so far.

Recently, I decided to change the question to a more personal one: “Are you good at having tough conversations at work and why?”. To that question, I can provide many more concrete ideas and examples. Today I am going to share some of my personal experiences with crucial conversations in the workplace.

There are few types of tough conversations that occur in the workplace for me. Among the most common are: crucial conversation, constructive feedback and criticism. According to a helpful definition from the internet, crucial conversations are discussions between two or more people where stakes are high, opinions vary, and emotions run strong.

I am quite good in giving constructive feedback when hiring external candidates. I do not find it difficult at all to give my honest opinion during code review in GIT, or in person to my colleagues during retro. This may be because the stakes are not too high for me, and do not have strong emotions towards people I do not know.

One time after very bad interview a candidate asked me straight after his technical interview to give him feedback. I said: “That is not how we do things here. All people who were involved in your interviews will get together and share their feedback. Then our HR will get in touch with you and deliver the feedback.” In my mind I also added “I already spent whole hour of my time on you, I don’t want to spend any more”.

By contrast, internal hiring process is way trickier. Here the stakes are way higher and there might be some strong emotions involved. A few times I have been asked to give feedback on candidates who had applied for roles in my tribe and I was very honest with my feedback. While I would never deliver it to those people directly, if I had any negative interactions with them in the past, I would openly say: “No way, we should never hire this person in our tribe! I am surprised that we hired him/her in the first place!”

Aside from hiring, I also struggle with crucial conversation with my peers. As a developer I have few opportunities for those in my day to day job. Therefore when I comment on someone’s pull request in GIT, I try to be as polite as possible. More often I phrase my feedback in a form of question like: ”Do think it would be better to do this?” or “Maybe it is a good idea to write some tests for this function?”. In rare cases when I know that my comment may trigger emotional discussion I will just approve PR and then maybe fix it later.

Additionally, I am often involved in architectural discussion, in which we try to pick the best solution for a specific technical problem or task. Here I only contribute when I know and trust people who are involved. I see that often the person with the best communication skills and the most authoritative title wins, so I do not fight too hard for my ideas. I do get upset when I believe that solution that was agreed on is not the best one, but I will not be vocal about it. I fear that if I continue to argue, I may spoil good relationships. The stakes are not ridiculously high for me, most likely I won’t be involved in supporting those systems when they built anyway, because restructures will inevitably happen.

At one point, my team decided to not invite our tech lead to few conversations because we knew that he/she would be against our solution. In the old days, I could win few arguments by suggesting that we invite some people to the discussion, knowing that my team members will agree with anything to avoid conversation with certain people. Sometimes I feel that our work discussions are becoming a form of bullying, where people with stronger debating skills can inflict their opinions on others. Once a graduate developer told me that her opinion in those discussions got often ignored maybe because she is a graduate. I told her that she may have been wrong, that she was getting ignored because she is a woman. Maybe my experience is not universal and majority of people do not feel the way I do.

Similarly, when it comes to delivering constructive feedback to my peers, I am the worst. I like to receive constructive feedback to grow, but I never deliver it. We don’t have a culture of asking each other for feedback, so why should I upset my team members with my personal opinion? I might be wrong in the first place! Also I rely on the knowledge that, that if situation becomes especially bad, someone else will say something to that person’s manager. Just not me.

Even when managers gather feedback from me on my team members, I give only positive thoughts. I know that it is very easy to know where the feedback is coming from. Likewise, when my manager delivers constructive feedback from my peers to me, I know who said what. So if I do it same way, my teammates can easily identify me as well. I would rather have a good positive relationship in my team. In the worst case scenario, I can just ignore the person I don’t like and wait for the next restructure to happen.

In the same way, when I am not happy with my manager and have some constructive feedback for him or her, I will never deliver it. The stakes are too high! I’ve seen people forced to leave companies because they disagreed with or challenged their managers. It is too risky! Giving constructive feedback in this situation will put a giant red mark on my career, therefore my strategy has become avoiding my manager as often as I can and, as you probably guessed by now, waiting for another restructure.

Likewise, I am bad when I happen to be on the receiving end of the crucial conversation or constructive feedback. I do not stand my ground. When people give me their constructive feedback or ask me to do something that I don’t think is right, I just smile and agree with everything that they say. I will still try to do the things my way if possible afterwards, then pretend that it was my understanding of their request in the first place, but I will never challenge them directly.

The only situation when I felt I was good at crucial conversations was when I was a manager myself. It was my job to deliver constructive feedback and answer tricky questions and I did it. I knew I had no choice, it was my duty. Some conversation were hard, but I could not just avoid them or be very polite. I need to make sure the person I manage knows when he or she is not doing well.

Nevertheless, once in a blue moon due to stress or workload, my guard is down and I do initiate a crucial conversation or openly express my criticism. When that happens, emotions are strong and my comments can come across as bullying or harassment. There have been a few times when I failed to restrained myself from voicing my opinions about poor architecture or system performance, and my words were taken personally. In one case, I quickly received feedback to calm down, take a day off, and was given a number to call. I did ask for forgiveness the next day, even when I did not mean it, but it was the only way out for me. I do feel bad for upsetting people though. I know that I had constructive facts and data to offer, but I expressed myself in a very destructive way. My behavior did not help to solve the problems, and it made it harder to talk about them in the future.

The obvious answer to a lot of these challenges seems like it would be “training”. I have done lots of internal and external training on feedback and crucial conversations, and I am really good at it in the classroom! I know so many different techniques and I’ve read so many good books, but I fail in practice. I prefer to wait until the next restructure to avoid the issue, or rely on people leaving the company. On the other hand, why should I worry about it? Isn’t it better to have a good harmonious relationship within the company without upsetting each other? Yes, we might have to pay a small price in productivity, revenue or losing a few good employees, but really is that such a big price to pay for a friendly, trusting environment?

By writing this article I am admitting that I do have a problem with tough conversations, a big one! They say, the first step is admitting you have a problem.

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