The Conversation You Keep Putting Off: A Practical Guide to Difficult Conversations at Work
It is Sunday night and you are already thinking about Monday. Not the schedule. Not the sales numbers. The conversation.
Maybe it is Dave, who has been with you for eight years and has started rolling in fifteen minutes late most mornings. Maybe it is Alex, your top salesperson, who hits every target but leaves a trail of frustrated coworkers behind. Maybe it is Priya, who has always been your most reliable employee and lately seems like a different person.
You know you need to say something. You have known for weeks. And yet, every time the moment comes, you find a reason to wait. A busy week. A good day you do not want to spoil. A hope that it will sort itself out.
If that sounds familiar, you are in very good company. Most business owners and managers did not get into business because they enjoy difficult conversations. You built your company, or you were promoted, because you are good at what you do, not because someone trained you to tell a long-time employee that their work is slipping.
Here is the encouraging part: difficult conversations are a skill, not a personality trait. Skills can be learned. This quarter, our Pebbles video series broke that skill into eight quick tips. This article goes a step further, with the reasoning behind each tip, everyday scenarios, and the actual words you can use.
The people in this article are composite examples, not real clients. If one of them sounds a lot like someone on your team, that is rather the point.
Before the Conversation
Step One: Recognize When It Is Time to Talk
Not every frustration needs a sit-down meeting. Dave being late once because of a flat tire is life. Dave being late three times a week for a month is a pattern. Here are three signs it is time to talk:
It is a pattern, not a one-off. One bad day is not a performance issue. Repeated behaviour is.
It affects the team, customers, or safety. If a coworker is quietly doing Dave's opening checklist every morning, the problem is no longer just Dave's.
You have caught yourself complaining about it to someone else. If you have vented to your business partner, your spouse, or another manager more than once, that is your signal.
That last sign deserves a closer look. Dale Carnegie's very first principle is "Don't criticize, condemn, or complain." Complaining about someone feels productive, but it changes nothing, and it often leaks into how you treat them. The fix is simple to say and harder to do: talk to them, not about them.
Going a step further: the cost of waiting. Waiting is rarely neutral. Your team is watching, and silence sends its own message: the standard is optional. Employment lawyer Jonathan Segal, writing for the Society for Human Resource Management, also points out a legal reason not to delay. The longer you wait, the more any action you eventually take can look like retaliation rather than fair management, and the more time an unhappy employee has to take legal steps first. Early conversations protect everyone, including you.
Step Two: Bring Facts, Not Feelings
Before you walk into the room, take ten minutes to write down what you have actually observed. Compare these two sets of notes about Dave:
Feelings | Facts |
Dave does not care anymore. | Arrived after 8:15 on September 8, 10, 15, 17, and 22. Shift starts at 8:00. |
He is always late. | Opening checklist completed by a coworker on those five days. |
He is leaving everyone else to pick up the slack. | Two customer calls went unanswered before 8:15 on September 17. |
The notes on the left will start an argument. The notes on the right start a conversation.
A few preparation tips, drawn from Segal's guidance:
Use specific examples with dates. Vague feedback is easy to dispute and hard to act on.
Skip absolutes. Words like always and never invite the employee to find the one exception, and suddenly you are debating Tuesday instead of the pattern.
Focus on results, not intent. You do not know why Dave is late yet. You only know that he is. Leave the motive out of your notes.
Know your goal. Before you begin, finish this sentence: "By the end of this conversation, I want us to agree on…" If you cannot finish it, you are not ready yet.
Finally, pick your setting. Choose a private space and a time when neither of you is rushed. A conversation squeezed in at the end of a hectic shift rarely goes the way you planned.
During the Conversation
Step Three: Start Friendly, Then Get to the Point
Dale Carnegie advised us to "Begin in a friendly way" and to "Begin with praise and honest appreciation." The key word is honest. One sincere sentence sets the tone. Five minutes of small talk about the weekend does the opposite: the employee senses something is coming, their anxiety climbs, and your message gets blurry. Segal's advice for performance conversations is blunt: skip the chitchat. Use an approach that suits you and the situation, but I prefer the former, with a softer approach toward a team member that makes future conversations more palatable.
Here is what that sounds like with Dave:
Too vague: "Hey Dave, how is it going? Good weekend? So, uh, just wanted to touch base on a few things, nothing major…"
Too harsh: "Dave, your lateness is a problem and it needs to stop."
Just right: "Dave, you have been one of the most dependable people on this team for eight years, and I value that. I want to talk with you about something important: your start times over the past month."
The third version is respectful, clear, and done in about fifteen seconds.
Step Four: Describe the Problem With Situation, Behaviour, Impact
This is where most conversations go sideways. We reach for labels: attitude, rude, lazy, not a team player. Labels are conclusions, and people defend themselves against conclusions.
The Center for Creative Leadership's Situation-Behaviour-Impact model replaces the label with three plain facts:
Situation: when and where it happened.
Behaviour: what the person actually said or did, the kind of thing a video camera would capture.
Impact: the effect it had on people, work, or customers.
The Center reports that this approach reduces both the anxiety of giving feedback and the defensiveness of the person receiving it.
Let us try it with Alex, the top salesperson:
Label: "You need to fix your attitude with the team."
Situation, Behaviour, Impact: "In Tuesday's team meeting, when Jordan raised a concern about delivery times, you said 'That is not my problem' and turned back to your laptop. Afterward, two people told me they no longer feel comfortable raising issues in meetings."
Alex can argue with "attitude." It is much harder to argue with what happened on Tuesday.
Going a step further: ask about intent. The Center for Creative Leadership adds a fourth step: after describing the impact, ask about the intent. "What was going on for you in that moment?" Perhaps Alex was fielding a call from an angry client. That does not excuse the behaviour, but it turns a lecture into a dialogue, and dialogue is where change happens.
Step Five: Let Them Own the Solution
Once you have named the issue, resist the urge to hand over the fix. Carnegie put it this way: "Ask questions instead of giving direct orders." He also observed that people commit more readily when they "feel that the idea is his or hers."
Questions that work well:
"What do you think is getting in the way?"
"What would help you get here by 8:00?"
"What would you suggest?"
"What do you need from me?"
Then, and this is the hard part, stop talking. Let the silence do some work. The authors of Difficult Conversations, from the Harvard Negotiation Project, make the point that a conversation cannot move forward until the other person feels heard.
Back to Dave. When asked what is getting in the way, he explains that his daughter's daycare changed its drop-off time in August, and he cannot get there before 7:45. Suddenly the problem looks very different. Dave suggests starting at 8:15 and staying until 4:15. You check whether that works for the opening shift, and it does if another employee opens on Mondays.
None of that comes out if you open with, "You need to be here at 8:00, full stop."
Going a step further: know when the answer changes your obligations. In Alberta, family status is a protected ground under the Alberta Human Rights Act. When an employee's explanation connects to a protected ground, such as family status or a medical condition, you may have a duty to accommodate. The Alberta Human Rights Commission's own guidance uses a schedule adjustment for daycare drop-off as an example. It also notes that accommodation relates to caregiving obligations rather than preferences, and that employees are expected to look at their own options first. That does not mean you must say yes to every request, but it does mean you should pause, explore options, and get advice before saying no.
Step Six: Let Them Save Face
Carnegie's principle "Let the other person save face" may be the most important in this entire article. People can recover from hearing hard feedback. They struggle to recover from being embarrassed.
In practice, that means:
Always hold the conversation privately. Never in front of the team, never in a shared office with the door open, and never by group email.
Focus on the problem, not the person. "The checklist was not done" rather than "You are unreliable."
Own your part first. Carnegie advised talking "about your own mistakes before criticizing the other person." If you never clearly said the opening checklist must be finished by 8:15, say so: "I realize I have never put that expectation in writing. That is on me, and I want to fix it today."
Keep it between you. Do not debrief the team afterward. If the conversation is the talk of the lunchroom by noon, trust is gone.
Difficult Conversations describes this as shifting from blame to contribution: instead of asking "Whose fault is this?", ask "How did we each contribute to this, and what will we each do differently?" That is not letting anyone off the hook. It is making it easier for both of you to move forward.
When Something Else May Be Going On
Step Seven: Check In Before You Discipline
Priya has been with you for five years. She is the person everyone goes to with questions. Over the past two months, she has missed three deadlines, called in sick on several Mondays, and seems withdrawn in meetings. Last week she snapped at a customer, which is completely out of character.
The instinct might be to treat this like Dave's lateness: gather the dates, describe the behaviour, set expectations. But a sudden, unexplained change in a reliable employee is a different situation, and it calls for a different first conversation.
In Alberta, employment lawyers describe this as the employer's duty to inquire. When there are clear signs that a medical or mental health issue may be affecting someone's work, employers are expected to ask whether support is needed before moving to discipline. Disabilities, including mental health conditions and substance use disorders, are protected under the Alberta Human Rights Act.
What this conversation sounds like:
"Priya, I have noticed some changes lately, and I wanted to check in with you. This is not a disciplinary meeting. You have been a huge part of this team for five years, and I want to make sure you are okay. Is there anything going on at work where we could support you?"
A few guardrails:
Do not diagnose. "Are you depressed?" or "Is it a drinking problem?" is not your question to ask.
Do not demand a diagnosis. If accommodation is needed, what matters is the person's functional limitations, what they can and cannot do, not the medical label.
Do offer support, and keep checking in. Mention your Employee and Family Assistance Program if you have one. If she is not ready to talk today, schedule another check-in rather than waiting for her to come to you.
Do document the check-in. A short note of the date, what you observed, and what support you offered.
Why you go to them, rather than waiting for them to come to you. "My door is always open" sounds supportive, but it quietly places the responsibility on the employee. The person who is struggling, embarrassed, or worried about their job is often the least likely to knock on that door. Intentional management means you take the first step. When you notice the change and start the conversation, you show Priya that you are paying attention, that she matters, and that asking for help will not count against her. The open door still matters, but it is the follow-up, not the plan.
Going a step further: the check-in is a conversation, not a pass. Checking in does not mean performance expectations disappear. It means you understand what is happening before deciding what comes next. If Priya says everything is fine and the issues continue, you can move to a performance conversation using Steps Two through Six, having done your due diligence. If she does share something, our earlier Pebbles episodes on terminations and medical issues walk through the accommodation steps that follow, and this is a good moment to call in HR support.
After the Conversation
Step Eight: End With a Plan, Then Follow Through
Many difficult conversations do not fall apart because of a badly worded opening. They fall apart because of a conversation that ends with "Okay, so… let us just try to do better," and then nothing happens. Two months later, you are back where you started, now with a frustrated manager and a confused employee.
Before you leave the room, agree on three things:
The expectation. What specifically will look different? "Arrive by 8:15 and complete the opening checklist by 8:30."
The timeline. How long before you assess progress? "Let us look at how the next four weeks go."
The follow-up date. Put it in both calendars before the meeting ends. Not "we will check in sometime," but "Thursday, the 30th, at 2:00."
Then write it down. A short summary, ideally shared with the employee, should capture what was discussed, the date, and what each of you agreed to do. Keep it factual and focused on behaviour and outcomes, not opinions. If the issue resolves, the note simply shows a good conversation. If it does not, the note becomes the foundation for whatever comes next.
Going a step further: notice the improvement. This is the step almost everyone skips, and it may be the one that matters most. Carnegie advised us to "Praise the slightest improvement and praise every improvement," and to "Make the fault seem easy to correct."
Two weeks after your conversation, Dave has been in by 8:15 every day. Say so:
"Dave, I noticed the opening checklist has been done early every morning. Thank you. It has made a real difference for the team."
That ten-second comment tells Dave the conversation was about the work, not about him, and it makes the next difficult conversation, whenever it comes, much easier for both of you.
And if things do not improve? Then you have a clear, documented starting point for the next step in your disciplinary process, with a record showing that you were fair, specific, and supportive from the beginning.
Your Difficult Conversation Checklist
Save this for the next time you are dreading Monday morning:
☐ Is it a pattern, does it affect others, or have I been complaining about it?
☐ Have I written down specific facts, dates, and impact, without absolutes?
☐ Do I know what I want us to agree on by the end?
☐ Is the setting private and unrushed?
☐ Is my opening one sincere sentence, then the point?
☐ Am I describing situation, behaviour, and impact instead of using labels?
☐ Have I planned questions that let them help build the solution?
☐ Am I ready to own my part?
☐ If this is a sudden change, should I start with a check-in instead?
☐ Will we leave with an expectation, a timeline, and a follow-up date?
☐ Have I put a reminder in my calendar to notice improvement?
The Bottom Line
Difficult conversations do not get easier by waiting. They get easier with practice, preparation, and a few good habits. The goal is not to win the conversation. It is to leave the room with a clearer path forward and the relationship intact.
Dave, Alex, and Priya are not problems to be managed. They are people who need clear expectations and a manager willing to have an honest, respectful conversation. That manager can be you.
If you have a conversation you have been putting off and want a second set of eyes on your approach, Red Rock HR offers a 30-minute consultation, along with performance management guidance and conflict management assistance. Reach out at redrock@redrockhr.ca. We are here to help you get it right.
Want the quick version? Watch our Pebbles series on difficult conversations, eight tips in about 20 seconds each.
Sources
Dale Carnegie Training. Dale Carnegie Principles. https://dalecarnegie.com/en/culture
Segal, Jonathan A. 11 Tips for Talking About Poor Performance. Society for Human Resource Management, March 31, 2016. https://www.shrm.org/in/topics-tools/news/hr-magazine/11-tips-talking-poor-performance
Center for Creative Leadership. Closing the Gap Between Intent and Impact. https://www.ccl.org/articles/leading-effectively-articles/closing-the-gap-between-intent-vs-impact-sbii/
Stone, Douglas, Bruce Patton, and Sheila Heen. Difficult Conversations: How to Discuss What Matters Most. Summary by Beyond Intractability. https://www.beyondintractability.org/bksum/stone-difficult
Alberta Human Rights Commission. Family and Marital Status. https://albertahumanrights.ab.ca/media/sm3gfeba/family-and-marital-status.pdf
Duty to Inquire in Alberta. Alberta employment law firm summary. https://stlawyers.ca/labour-employment-law-employees/duty-to-inquire-alberta/
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