Avoiding Hard Conversations

Paulo Moncores

Senior Engineering Manager at Shopify



People often wait for too long to have hard conversations. Whether your employee is underperforming or their behavior is not as expected and desired, there is no need to avoid or further delay hard conversations.

Culture plays a critical role in how people approach hard conversations. I currently live in Canada but have been living in Germany where I led a department with people of 32 different nationalities. My impression is that Europeans are much more straightforward when having to deal with hard conversations, unlike people from Canada and Latin America who prefer a more polite and considerate approach. Here in Canada, I find it much challenging to initiate these conversations as people usually tend to avoid any type of confrontation.

Actions taken

I was inspired by a radical candor framework, a framework developed by an author and ex-tech executive Kim Scott. Her approach encouraged me to practice radical candor and develop caring and trustful relationships with my reports while providing feedback directly.

Before talking to someone, I like to write down things I intend to say. It helps me disconnect emotionally and focus on actual problems. I would dissect the problem and describe how I feel about it. I would never tell anyone, “You are not reliable” because that is merely my perception of a person/situation. However, I can state how I was feeling, “I felt excluded when I heard you saying in the meeting that you implemented the project single-handedly”. No one can challenge or tell you that you are right or wrong about your own feelings and perceptions. Then, I would typically explain the impact a certain situation had on me, the team, etc. For example, “Your behavior impacted the team and they become more reluctant to share their ideas”. Finally, I would sketch a hypothetical situation that could solve the problem, “In my opinion, this is the best thing to do it”. Be clear about proposed actions because people who want to change their behavior don’t always know how to do that.

Don’t wait for too long to deliver feedback. Feedback should follow immediately after you have experienced or witness a certain situation. Take a brief moment to reflect on, subdue your emotions, and then arrange to talk with the person in question. Though we are all now stuck in the remote realm, avoid Slack as much as possible, and find a way to communicate that would include the ability to observe someone’s facial expression.

Through the conversation, be open to listen and always assume another person’s positive intent. I doubt that anyone wakes up in the morning and thinks about how to intentionally make the life of their colleagues miserable.

Culture plays a decisive role in how people are approaching hard conversations. Instead of treating people the way you want to be treated, treat them like they would want to be treated. People from different cultures would certainly prefer to be treated differently, and you will learn how to best approach them through one-on-ones. For example, when you already know that a person comes from a culture that typically avoids confrontation, approach them with carefully chosen words, “I have noticed something during the meeting, I would like to hear your perspective on this”, and then after hearing what they have to say, ask if you can share your opinion on the same matter. On the other hand, with people who are open and keen on taking feedback, be straightforward and to the point.

Lessons learned

  • Don’t delay feedback. Things can only get worse if you delay it. Imagine having to let go of a person and they are not aware of that possibility. No one is beyond redemption. Sometimes we fail to provide feedback and help a person change their behavior or adjust their expectations.
  • Don’t put permanent labels on people. For example, this person is hard to talk to. By doing so, you are not allowing them to change and grow. The most effective way for people to change and grow is to provide them with critical feedback.
  • Make a balance between criticizing people and giving them praise. Our praise is often abridged into a “great job”. “Great job” should be followed by an explanation of why it is great.

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Paulo Moncores

Senior Engineering Manager at Shopify

Leadership DevelopmentCommunicationCulture DevelopmentFeedback Techniques

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