Free resource · Toolkit
Difficult Conversations Toolkit
A practical guide for managers and owners who need to raise a concern with an employee. Use it to prepare, hold a fair and focused conversation, and follow through on what you agree.
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1. Prepare: separate what you saw from what you think
Most difficult conversations go wrong before they start, when a manager walks in with a conclusion instead of an observation. An observation is something you could point to: a date, a piece of work, words someone said. An assumption is your explanation for it. Assumptions may turn out to be right, but they belong in the conversation as questions, not as facts.
| What I observed Specific, dated, factual | What I'm assuming My interpretation or guess at the reason | How I could check A question I can ask |
|---|---|---|
| The March invoice summary was due Friday and was sent Tuesday. | They don't treat finance deadlines as a priority. | “What got in the way of the Friday deadline?” |
Before you meet, answer these
- What outcome do I want from this conversation, in one sentence?
- What is the impact of the issue, on the team, the client or the work?
- What might I not know about their situation?
- Have I been clear about this expectation before? Where and when?
- What support or change could I offer?
- What am I prepared to be flexible on, and what isn't negotiable?
2. A structure for the conversation
This order keeps the conversation focused and fair. It moves from your view, to theirs, to a shared plan.
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State the purpose
Name the topic plainly in the first minute. Small talk followed by a sudden turn feels like an ambush.
Avoid: softening it so much that the point gets lost.
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Describe what you observed
Share one or two specific examples from your worksheet. Keep to facts.
Avoid: words like “always”, “never” and “attitude”.
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Explain the impact
Say why it matters: who it affects and how. This connects the issue to the work, not to the person.
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Ask for their perspective, and listen
Ask an open question, then stop talking. Check the assumptions you wrote down. You may learn something that changes the conversation.
Avoid: planning your reply while they speak.
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Agree on what happens next
Work out specific actions together: what will change, who will do what, and by when. Be clear about the expectation going forward.
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Close and confirm follow-up
Summarize what you agreed, set a date to check in and thank them for the conversation. Send a short written recap afterwards.
3. Example openings
Adapt these to your own words and situation. Each one names the topic, stays specific and opens the door for the employee's view.
Missed deadlines
“I'd like to talk about the supplier report. It was due Monday and arrived Wednesday, and it's the second late report this month. I'm not here to assign blame. I want to understand what's getting in the way and work out a plan that holds.”
“The schedule for next week went out after the team had already made plans, and two people had to swap shifts at short notice. Can we look at what happened and how we can get it out by Thursday?”
Unclear expectations
“I think I wasn't clear enough about what I needed on the client proposal, and that's partly on me. Could you walk me through what you understood the goal to be? Then I'll share what I had in mind, and we can agree on it together.”
“You've been doing a lot of the customer follow-up yourself, and some of it overlaps with Priya's role. I want to make sure we're both clear on who owns what. Can we go through it?”
Everyday team friction
“I've noticed some tension in recent team meetings, especially around how work is handed off between you and Daniel. Before I talk with anyone else, I'd like to hear how it's been from your side.”
“A few comments in the team chat this week came across as sharper than I think you intended. I'd like to talk about how we keep disagreements about the work from becoming personal.”
4. Questions that invite their perspective
Open questions show that you want to understand, not just be heard. Choose two or three that fit.
- How do you see the situation?
- What's been getting in the way?
- Is there anything about this I might not be aware of?
- What would help you meet this expectation?
- What could I do differently to support you?
- What do you think a good solution looks like?
- Which part of this feels most difficult to change?
- How would you like us to check in on progress?
5. Agreed actions and follow-up
Fill this in together at the end of the conversation, or straight afterwards, and share a copy with the employee.
- Employee
- Manager
- Date of conversation
- Topic
| Action | Who | By when | How we'll know it's done |
|---|---|---|---|
- Support offered
- Follow-up date
- Notes from follow-up
6. When to get qualified HR support
A guide like this works for everyday concerns about performance, expectations and working relationships. Some situations need more than a good script. Pause and get qualified HR or legal advice before going further if:
- The concern involves possible harassment, discrimination, bullying or violence.
- The employee mentions a health condition, disability, family situation or another personal circumstance that may affect their work.
- You're considering discipline, a formal warning or ending employment.
- The same issue continues after earlier conversations and agreed actions.
- The employee raises a complaint about you, or about someone senior.
- There's a union, an employment contract term or a legal dispute involved.
- Anyone's safety may be at risk. Deal with safety first.
Rules on accommodation, discipline and termination differ between provinces, states and countries. Getting advice early usually makes the situation easier to resolve fairly.
