There’s a conversation you know you need to have. Maybe it’s with an employee who didn’t get the promotion they expected. Maybe a teammate missed an important client deliverable deadline that impacted everyone. Or maybe it is with a family member.
The million-dollar question is, are you putting it off and avoiding it or do you address these quickly. If your answer is you’ve been avoiding it, know that you are in good company. 83% of employees report avoiding at least once crucial conversation at work.
Avoidance Is a Leadership Decision
Lets stay with talking about work – but personal follows much the same path. Most leaders don’t avoid difficult conversations because they don’t care. They avoid them because they care a lot. In fact, you have likely lost sleep over the idea of having to have a difficult conversation. You’ve replayed it in your head and in some cases, you’ve even justified waiting.
You may have told yourself, “I’ll deal with it next week.” And you have good reason to hold back. There is an important project and you don’t want to discourage the employee. Or, you don’t want to say the wrong thing. Or you are worried they are going to over-react.
Unfortunately, next week comes and the challenge is still there… unaddressed… and because time has gone by it is even more difficult and awkward to discuss. Maybe worse, (often worse). And often avoiding the conversation has done damage to your reputation as a leader with other members of your team… and may even have erroded your confidence in yourself.
Let’s hope you haven’t avoided the conversation for too long.
Set Expectations Far in Advance
I love this first step, but it isn’t going to help you in this case. But you can implement it tomorrow and it will help you for any future difficult conversations you will need to have.
Your first, future step is to ask for permission long before you need to have a difficult or crucial conversation.
Imagine I am a new member of your team starting tomorrow. And imagine that as part of my first day and your onboarding meetings you say something like. “I hope you are getting the sense that we are a team that values trust and respect. Part of that means we respect differences of opinion, shared construction feedback, and accountability… as part of our individual and collective growth. So, Bruce, I want you to feel comfortable knowing that at times I will share constructive feedback with you. 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 sets the stage so that when a difficult conversation has to happen that neither of us needs to worry – or at least worry less. Because we know we are both safe it should mean we will both be able to stay present, learn from, and resolve the challenge quickly without becoming hyper-nervous or defensive.
Know Your Goal Before You Speak
Before you speak, define why this conversation matters. If your goal isn’t constructive, pause. You have to be invested in solving a real and important challenge. Remember, your reputation is on the line.
When a necessary conversations goes sideways it’s often because the leader isn’t clear with what happened, why it matters, and when. So, before you meet with someone, take a few minutes and answer four questions:
- Is it your responsibly to say something? (Intention)
If it’s not your place to speak up or the other person doesn’t trust your opinion, then don’t - What actually happened? (Facts)
Strip away assumptions and emotion. What observable facts did you experience first-hand - Why does it matter? (Impact)
What was the effect on them, the team, the client, the business? - What needs to change? (Expectation)
Have a solution in mind, but invite them to suggest a solution.
If I do choose to speak up, it’s critical you have an idea of what outcome you hope for? How will this conversation make things better? But still be flexible. If you are going to ask them for suggestions into a solution, you have to be open to listening to them and implementing any good / appropriate ones. This will help them buy-into the solution.
Being clear on your purpose and desired impact will reduce the likeliness of anyone becoming defensive and will build your credibility.
If you are going to approach a difficult conversation, be sure you stay with facts that you experienced. Hear-say is a dangerous thing. You also want to be very careful of bias. Yours, theirs and anyone else involved.
Also, don’t assign blame or decide in advance why they did XYZ. Far too often honest or naïve mistakes are just that. But there is this weird thing humans do, we assign intention to “why” someone did XYZ. For example, “They are lazy.” Or “They wanted the new process to fail”.
Reframe the Conversation Before You Have It
Am I acting from care or frustration? If it is frustration, take a moment to manage that frustration before you begin.
When you do have to have a difficult conversation, go into it with a frame of mind that this is your shared opportunity to build trust, clarity, and accountability. And, when speaking with an employee or co-worker, I believe it is critically important, at least in your own intention, that you are doing this to help that individual learn and support their career for their future.
This should be a natural step if you had asked for permission in advance of ever needing the difficult conversation.
I can assure you that if you start with a positive intention, your conversation has a much higher chance of staying positive and productive – even if it has a bump or two along the way. But, if you go into the conversation feeling and acting guarded, tense and with a long list of policies, “I told you’s” and “you did’s” then you should expect the other person or people to match you tense defensive posture.
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.
Start the Conversation Without Making It Worse
How you open the conversation sets the tone. Your first sentence matters. If you lead with accusation, you’ll immediately get defensiveness. If you lead with curiosity, you’ll get engagement. Even saying something like, “Hi Bruce, let’s go into my office to discuss what happened with the XYZ report, why it was late and how to move forward. This is important and I want to make sure we are both doing better at setting and meeting expectations next time.”
Next, focus on behaviour and impact, not character. You can even share if you were disappointed if it is a valid feeling. For example, “I’m disappointed you didn’t feel you could come to me when you first felt the client installation date was in jeopardy. But for now, let’s work together to resolve this and decide what to do if you find yourself in a similar situation in the future.”
Here’s what that looks like in real situations:
- Missed Promotion
“I know this outcome may be disappointing. Let’s meet to explore what opportunities you see for yourself so I can help you.” - Missed Deadline
“I want to talk about the timeline on the last project and understand what got in the way.” - Client Deliverable Went Wrong
“Let’s explore what happened so we can learn from it and prevent it going forward.”
Co-Create the Path Forward
This isn’t about telling someone what to do and walking away. It’s about building ownership. Ask:
- “What would you do differently next time?”
- “What support would help you succeed here?”
When people are part of the solution, they’re far more committed to it. You move from compliance to accountability.
Close with Alignment and Confidence
Before you end the conversation, make sure there’s no ambiguity.
- Summarize what was discussed
- Confirm expectations
- Reinforce your belief in them
Something as simple as: “I’m happy we’re aligned on how to move forward and have clearer checkpoints. I’m confident next time the project will go very well.”
That last sentence matters more than most leaders realize. People don’t just remember what you said — they remember how they felt after the meeting. Being ‘too nice’ as a leader doesn’t make people respect you. Employees respect, trust, and follow leaders who are tough on them and also fair.