How to have difficult conversations at work

How to Have Difficult Conversations at Work

I recently attended a fantastic training course on how to have difficult conversations. And I wanted to share some of my key takeaways with you.

I joined this training course with one goal in mind: I wanted to learn how to have difficult conversations without burning any bridges.

Most of the time, I have no problem with confrontations. Because I’m so passionate about helping people around me to improve themselves, I’ve always been one of those individuals who are more than happy to point out all your flaws and let you know what you could do to improve yourself.

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Despite my good intentions, I’ve been accused of coming across too forceful, blunt, or even rude by those people around me. I had accidentally made people feel worse about themselves, instead of helping them to become more self-reflective and learn from my feedback. So, I was keen to know how I could provide constructive criticism without being a d***.

Everyone needs to know how to handle difficult conversations

‘Only managers need to learn how to have difficult conversations,’ you might be thinking. Not quite!

As sad as it sounds, there are many instances at work where you’ll need to practice your difficult conversation skills, no matter what your role is. There are many reasons why you may need to have crucial conversations at work.

If you are a manager, you might have:

  • A staff member whose performance has dramatically decreased recently
  • A staff member whose performance has dramatically decreased recently
  • A staff member who is always disrupting other people in the team
  • Other people from the business have filing complaints about a particular staff member of yours
  • Bad news that you have to announce to the team.

As a team member, you might have:

  • A coworker who has said or did something offensive to you
  • A coworker whose behavior has been hindering your performance and productivity
  • A team member with a bad attitude that’s bringing down the team culture
  • Witnessed a coworker doing something that seriously violates your company’s values or policies.

Don’t avoid the problem

Any person or situation could spark a need to have difficult conversations, and it’s handy to know how to be ready for them. Most of us hope that the issue will go away by itself so that they can avoid the awkward confrontation. And sometimes they might.

But most of the time, the issue won’t go away on its own. Every time you avoid confronting a problem with your coworker, staff member, or even your manager, you’re actually rewarding them for their bad behavior. If you don’t have the difficult conversation with them to highlight the problem, they will continue to act in a way that you don’t want them to. And that’s not what we want.

Timing is everything for your difficult conversation

You don’t want to wait too long for your conversation that you don’t feel like you’re bringing up ‘what’s in the past.’ But you don’t want to address the issue in the heat of the moment so that you say something you’d regret. The best time to have your difficult conversations is as soon as possible when both you and the other person is feeling calm.

Go somewhere quiet to talk

The last thing that you want to do is have your crucial conversation in a busy office hallway. The ideal place for you to have your tough talk is a quiet, soundproof meeting room. Try and create an environment where both you and the other person can talk honestly and freely without having to look over your shoulder because you’re worried about who’s listening. You also want to avoid getting your conversation disrupted by other people who are chasing you up about an urgent report or awkwardly trying to join in your conversation.

Forget the shit sandwich

In my training course, I learned that the shit sandwich was not an effective way of giving feedback. If you don’t know what a shit sandwich is, Walter Chen explains it nicely in his post about giving performance feedback. When you’re trying to start your conversation, the best thing to do is cut out the sugar-coating and get straight to the point. Why did we think to start a conversation with a praise and then shooting the other person down with a negative feedback was ever a good idea?

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Always a plan a follow-up

To ensure that the other person doesn’t fall back into bad habits, they need to take accountability for their actions. And the easiest way to create accountability is to plan a follow-up. You need to let the other person know that if they continue with their bad behavior and nothing changes, there’ll be consequences. You don’t necessarily have to threaten them with getting the HR team involved at this point. Just let them know that you’ll have another chat with them in a week’s time if you notice that the situation hasn’t improved.

Use the power of silence

The mistake that a lot of people make during difficult conversations is that they talk too much. You might be tempted to fill in those awkward gaps with more and more words. And by the end of your conversation, the other person hardly managed to get a word in! To have an effective conversation, ask more questions and talk less. Don’t be afraid to sit in silence until the other person starts talking. They might just need that gentle push to open up and start conversing with you properly.

Let the other person provide the solution

Another common mistake that a lot of people make is to tell the other person what to do. To encourage the other person to take accountability and be engaged in your conversation, it’s much better to let the other person come to their own solution. This is where practicing silence also comes in handy. Just state the facts of the problem to the other person, fall silent, and then wait for the other person to come up with the best solution.

Have I missed anything?

What are your tips on having difficult conversations at work?

Share by leaving a comment below!

6 thoughts on “How to Have Difficult Conversations at Work”

  1. Wow what a great post!

    I can completely relate to you! I’m a pretty nice and genuine person, so when people see me giving constructive feedback, I instantly get slammed in the face and the issue goes to my “new attitude/ being mean/ having an off day” AND the main issue gets ignored or unsolved.

    I don’t see this with me too often but it does happen on occasion. It’s the worst when you see it with other people too.

    I’m going to try some of these tips and see if they help. (I feel our generation is scared of confrontation because they don’t want to feel that they are bad at a skill or a task. Though people are never bad at anything. I believe it’s either a lack of skill or effort. I feel like it’s everyone’s jobs to encourage and correct inappropriate behaviour or lack of knowledge ).



    1. Hi Jenn, thanks for your feedback! Yes, I know exactly what you mean – when my confrontations get heated, I sometimes get accused of having a “moment” and end up having to apologize for my behavior. Unfortunately, this generally happens more often with women than men.

      You should definitely try out the tips and let me know how you get on! I think the key is practice, and practicing how to control your conversation. Hardly anyone is born being naturally good at having difficult conversations. Ever since I started using these techniques, my difficult conversations have turned out way better with much less tension. Good luck! 🙂


      1. Welcome 🙂

        Yup I get that exact same thing. I always always ALWAYS apologize when I shouldn’t have to.

        I feel like dealing with confrontation has not been practiced enough in our generation. It’s obviously talked about but also kind of ignored.

        I will def keep you posted. I need to try them 🙂



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