How to Have a Difficult Conversation at Work

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Difficult conversations and constructive feedback in the workplace is essential.

When you choose to have a tough conversation, it almost always means you care enough about the topic or work, the people and the relationship to face discomfort.

The short-term discomfort of having a difficult conversation almost always far surpasses the benefits of stronger relationships, greater trust and higher productivity. But, knowing how to have a difficult conversation at work, and how to receive constructive feedback are important parts of your shared success.

Before I share seven practical steps to handle tough talks at work, I want to share one important suggestion I make when facilitating difficult conversations training. Ask for permission long before you need to have them. For example, imagine on your first day at work your boss said something like:

  • “We respect differences of opinion, shared feedback, and accountability. I want you to feel comfortable knowing that at times I will share constructive feedback with you. And I want you to know that my intention is to always deliver feedback with respect and to help you and/or a project be better. I also want you to know that I am asking you to do the same with me - for me. How do you feel about this?”

This is the second of a three-part blog series focusing on the importance of difficult conversations, constructive feedback and crucial conversations. I invite you to use these seven practical steps to handle tough talks at work with empathy, clarity, and confidence—without losing trust.

1. Start With Purpose and Clarity

Before you speak, define why this conversation matters. If your goal isn’t constructive, pause. Ask yourself:

  • Is it my place to speak up? Does this really need to be said and to be said by me?

  • Have I seen or experienced the challenge personally? Hear-say and rumour will undermine your success.

  • If I do choose to speak up, what outcome do I hope for?

  • How will this conversation make things better?

  • Am I acting from care or frustration? If it is frustration, take a moment to manage that frustration before you begin.

Being clear on your purpose and desired impact will reduce the likeliness of anyone becoming defensive and will build your credibility.

2. Choose the Right Time and Place

A safe physical environment will help strengthen emotional safety.

Avoid public settings. If you’re remote, have the conversation with video camera turned on, not over email or chat. Tone and empathy are critical for constructive feedback.

3. Begin With Respect

A safe emotional environment will help strengthen overall success. As I mentioned in the introduction for this article, begin setting expectations and tone with care and in advance.

Your first sentence will set the tone for the whole discussion. It will put people at ease or make them defensive. Consider starting with something like:

  • “I want to discuss something important because I care about our working relationship and think we can make things better.”

Acknowledge the importance and your shared values will help reduce tension and improve shared purpose.

4. Focus on Behaviour and Impact, Not Character

Address specific behaviours and results, not personal traits:

  • Don’t say “You don’t care about deadlines.”

  • Instead say “When the report was late, the client meeting had to be rescheduled, which added pressure for the team.”

Clarity without making assumptions and without being unkind or abrupt builds shared trust, respect and understanding.

5. Invite Their Perspective

Invite them to be part of the discussion. Every situation has at least two points of view. So, ask questions and listen to learn without judging or interrupting. Curiosity opens understanding; assumptions close it. Consider asking:

  • “How do you see it?

  • “What do you think led to that outcome?” 

6. Co-Create a Path Forward

Invite them to be part of the solution. Do not come with all the answers and force them upon the other person. Instead, ask them to help define next steps.

  • “What could we do differently next time?”

  • “What support would help make that easier?”

Shared ownership increases accountability.

7. Stay Calm, Stay Kind

Your tone sets the tone.

If emotions rise, pause. Taking a short break to go get everyone a glass of water (and think through what happened), is better than reacting in the moment.

Key Takeaway

A difficult conversation isn’t about blame—it’s about clarity, care, and progress. When done right, it strengthens trust rather than damaging it.

Giving constructive feedback is important because it should always help us all improve, build stronger relationships and more resilient teams, companies and products/services by helping to ensure everyone is aligned and working toward common goals and sharing the same values. 

Thank you for reading Part 2, “How to Have Difficult Conversations”. I look forward to hearing from you if you have any questions. You can click this link to read Part 1, “Why Difficult Conversations Matter.”

Bruce

About Bruce and Bruce Mayhew Consulting

Bruce is Corporate Trainer, Keynote Speaker, Author and Executive Coach.

Bruce Mayhew Consulting specializes in customized Difficult Conversations, Crucial Conversations or Conflict Management Training, Email Etiquette Training, Leadership & New Leadership Development, Generational Differences, Time Management Training and other soft skills training solutions in Toronto and across Canada. Bruce is also an Executive Coach to a few select clients.

Bruce is an experienced motivational speaker in Toronto and has inspired audiences across Canada and within the USA and the UK. Bruce works hard to always make sure your training event, conference, retreat, or annual general meeting is a success.