Whenever we feel the need to address our colleagues or bosses about changing their behaviour, or doing something they ignore, it could be considered a tough conversation. However difficult these conversations might be, they are part of a workplace reality and finding the best words to make the conversation go as smoothly as possible is not always easy. The following recommendations are based on research and personal observation. Although they might not respond to every situation, I hope they can provide a starting point to a successful resolution.

Why is it important to have tough conversations in the workplace?

First, let’s look into why these tough conversations are essential. In no particular order, having these conversations and working towards a positive outcome:

  1. Creates trust. When we address someone directly, it builds mutual trust and respect, demonstrating that we are prepared to discuss the problems colleague-to-colleague before escalating the issue or discussing it with management.
  2. Strengthens relationships. People appreciate when they are trusted to be approached and find solutions to problems together.
  3. Helps resolve conflict. By bringing issues out in the open, there is an opportunity to resolve them efficiently and successfully.
  4. Opens up reciprocal feedback. Since we provide feedback, it automatically welcomes any feedback from our counterparts.

What happens when we don’t have tough conversations?

Ignoring tough conversations makes us miss opportunities to improve as an organization and as individuals, understand our colleagues better, hear their perspectives and build trust.
There is also a risk that we partake in other damaging behaviours instead, such as: excluding, being passive-aggressive, gossiping, bullying, or insulting.

When should we have tough conversations?

  • When we want our colleagues to change something that is getting in the way of having a successful working environment.
  • When it’s something important that impacts the work and company, and we think the person can improve.

Tips to prepare for tough conversations

1. When you feel emotionally charged, use the 5 whys to identify which needs aren’t being met.

For example: “I feel heat building up in my chest and head.”

  • Why? “I’m mad.”
  • Why? “I expected that John would provide me with the report yesterday at 5 pm as we discussed. If he was going to be late, at least he should have sent an email to inform me. I am distraught.”
  • Why? “Because I checked my email at around 5 pm for his report, and it not being ready frustrated me. Yes, I didn’t need it at 5 pm in the end, but what if I did? What would happen then? I am bothered by that.”
  • Why? “Because I felt like he didn’t find it important to tell me that he would be late. He most likely didn’t care about the project, and he didn’t care how I felt. That bothered me.”
  • Why? “Because I want to work with someone who values the projects and who values my time.”

2. Work on your psychological flexibility

If you are upset about something, it’s essential to accept your emotions and be open to your thoughts to keep yourself psychologically flexible. Attempting to change your thoughts, feelings and emotions paradoxically has the opposite effect.

To do this, sit with and meditate on your emotions, accepting them instead of trying to fix or change them (See Choose Your Actions, Not Your Feelings). For example, if you are having distressing thoughts which are triggering your anger, such as “John is such a jerk!” or “Why do I have to work with John and Kim gets to work with Roger?” then using thought diffusion techniques can help untangle you from these thoughts (See Accepting Distress).

These techniques will help you accept your emotions and be open to unwanted thoughts, so they won’t impact how you behave during a difficult conversation (See Defusing Exercises).

If you are still caught up with your angry emotions and negative thoughts, don’t say or do anything at that time. Wait until you have processed them before making any call.

3. Identify the main repercussions of the behaviour

In cases where the behaviour impacts the work, identify its main repercussions. For example:

  • John sent me the report late. I then didn’t have time to complete the edit, and it was delivered 2 hours late to the client.
  • The client could be dissatisfied with the delay. This could impact their willingness to work with us again and what they say to other clients.

4. Additional tips

  • Before your discussion, identify how you want your colleague to behave in the future. Having a clear vision of your desired outcome before you start your dialogue will help the conversation be productive and constructive.
  • Identify what is in it for your colleague. Looking at things in terms of their benefits rather than yours will help you go into the conversation with a mindset prepared towards a mutual agreement.
  • Be aware that you are still operating under assumptions. Keep an open mind that your colleague may bring valid reasons for their behaviour, and be prepared to change your viewpoint.
  • Enter the conversation without too many expectations of what your colleague will say. If you already think you know what they will say, you may not listen to them appropriately.
  • Set up a good foundation for having tough conversations. The little things you can do in a day-to-day work environment, like smiling when greeting your colleague, asking them how their day was and taking an interest in their work, will come a long way in creating a good setting for those tough chats (if and when you need to have them).
  • Try to cover only one thing during a difficult conversation. Address multiple things only if they are interconnected. Bringing up a laundry list of grievances can overwhelm your colleague, and it won’t be beneficial for problem-solving and resolution.
  • If possible, keep the tough conversation about something recent or actual. Bringing up stuff from the distant past won’t help to build a positive future.

Tips for during the conversations

  • Respect your colleague’s reaction, and don’t try to control it. If they sense you are trying to manipulate their reaction, it might tear down the trust and affect the outcome.
  • Remember to explain your point but leave gaps and time for your colleague to respond to you. Keep the pace slow so that everyone has time to collect and express their thoughts.
  • Keep your mindset on finding solutions that work for everyone. Try to stay away from focusing on who is right and who is wrong.

What if the conversation turns sour?

If your intentions are in the right place, and if you are mindful of your emotions, avoiding defensiveness, criticism and other harmful behaviours, the conversation should not go sour. If your colleague turns to any of these behaviours, pause and don’t react or participate. Thank your colleague and suggest taking some time to think about it and reconvene at a different time.

What to do if you are still afraid of confronting people

Talk with your supervisor or a friend and come up with a plan together on tackling the issues.
Use additional defusing techniques to help you overcome your fears (See Overcoming Fear ).

Additional resources:
(a) How to Navigate Difficult Conversations, Mindful (b) A Psychologist’s Secrets To Holding Tough Conversations, Forbes (c) How to have a difficult conversation, Psyche

Stephanie Trott

Stephanie Trott

Director, Course Development @KnowledgeOne. Lover of history/languages/culture/food. Gentle spirit. Lifelong nerd.