A difficult conversation is less likely to damage trust when you address the issue early, focus on particular actions rather than someone's personality, listen to what the other person has to say, and agree on next steps. The conversation may still be uncomfortable. That's okay. Uncomfortable situations are part of life, but they don’t have to get ugly or end in broken trust.
Privacy matters more than many managers realize. If your small business doesn't have an appropriate place for a confidential employee or client discussion, a private office space in Spokane(opens in new tab) gives you somewhere to talk without coworkers or customers overhearing.
Don't Wait Until You're Angry to Have the Conversation
Imagine a Spokane business with five employees. One employee has arrived 15 to 20 minutes late several mornings over the past two weeks, leaving someone else to cover the phones. The owner notices. So does everyone else.
The owner likes the employee and knows he has been having some difficulties at home, so she decides to give it another day. Then another week. By the time she finally brings up the problem, she's no longer talking about three late arrivals. She's carrying several weeks of irritation into the room. Confronting a problem earlier gives both people a better chance of discussing what actually happened.
Get Specific about the Difficult Issue before the Meeting
Preparation doesn't require writing a script. It means being able to explain the concern without reaching for vague descriptions such as "bad attitude," "unreliable," or "not committed."
For our business owner, the relevant facts are straightforward: the employee arrived after 9:15 three times in two weeks, and another employee had to cover the front desk. Those details give her a reasonable way to begin:
"You've arrived after 9:15 three times in the past two weeks, and other people have been covering the front desk until you get here. I wanted to find out what's happening."
Now the employee knows exactly what the conversation is about.
Choose the Right Place for the Tough Conversation
A manager may spend time thinking about what to say and almost no time considering where to say it. For a sensitive discussion, the setting deserves some thought.
A coffee shop(opens in new tab) isn't private. Neither is the corner of an open office where everyone can hear voices even if they can't make out every word. Sitting at someone's desk can leave coworkers wondering what happened before the conversation is even over.
Give the Conversation Enough Time and Privacy
Choose a private spot and allow enough time that neither person has to keep checking the clock. A Spokane(opens in new tab) meeting room can be useful for small businesses, remote teams, and professionals without a private conference room.
The surroundings don't need to be elaborate. A closed door, a quiet room, and enough uninterrupted time to finish the discussion can make a substantial difference.
Avoid Subjective Wording & Accusations
Compare "You've been really unreliable lately" with the specific explanation about arriving after 9:15 three times. The first statement invites an argument about whether the employee is unreliable. The second gives them three actual events to discuss.
This advice can apply to difficult conversations beyond employee management. A business partner who repeatedly misses deadlines, a freelancer(opens in new tab) whose work isn't meeting expectations, or a client who keeps adding work outside the agreed scope all require conversations based on something concrete. Dates, examples, agreed-upon responsibilities, and observable actions keep the discussion connected to the issue that brought everyone into the room.
Be Prepared to Learn Something You Didn't Know
Back to our late employee. The owner explains what she's noticed and then asks what's going on. The employee explains that a childcare arrangement changed two weeks ago. The person who used to handle the morning school drop-off is temporarily unavailable, and the employee has been trying unsuccessfully to make the old schedule work.
Obviously, that information doesn't solve the problem. Someone is still covering the phones. It does, however, give the owner information she didn't have when the conversation began. They can now discuss whether a temporary schedule adjustment is possible or whether the employee needs to find another solution.
Listening Doesn't Require You to Change the Expectation
Sometimes you'll hear an explanation and still need to say, "I understand, but this needs to change." Listening gives you enough information to make that decision fairly. It doesn't require you to agree with every explanation or abandon a reasonable workplace expectation.
Ask questions when something isn't clear. Then give the other person enough room to answer without immediately preparing your rebuttal.
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Watch for Phrases That Make Things Worse
Certain phrases can turn a discussion about one problem into an argument about everything that happened over the past year, and once the conversation gets off track, a positive resolution becomes much harder.
Three Phrases to Watch Out For
- "You always..." One missed deadline can suddenly become an argument about every deadline the person has ever missed.
- "Everyone thinks..." Now the employee may wonder which coworkers have been talking about them instead of focusing on the issue.
- "Don't take this personally..." Telling someone how they're supposed to feel rarely makes difficult feedback easier to hear.
Say what you personally observed and explain why it needs attention. If you have several examples, have them ready instead of using words like "always" or "never."
What If the Conversation Gets Emotional?
Someone may become defensive, angry, embarrassed, or quiet. A difficult subject can produce a difficult reaction even when you handle it carefully. You don't have to fill each quiet moment. Give the person a moment to think if they need it.
If the discussion becomes too heated to be productive, it may make sense to stop and agree on a time to continue. That's different from abandoning the issue. Set a specific time to reconvene so the conversation doesn't quietly disappear from the calendar.
Finish With Next Steps
A surprisingly easy mistake is having a long conversation and leaving without deciding what either person will do afterward. Our business owner and employee might agree that the employee will begin work 30 minutes later for the next two weeks and adjust the end of the workday accordingly. They could also set a date to check in before returning to the normal schedule. Another situation might require a deadline, a behavior change, additional training, or a second meeting.
Write Down Important Agreements
For workplace performance issues, managers ought to follow company policies and applicable employment requirements for documentation. For less formal workplace discussions, a short follow-up note can still be useful. A few sentences confirming what you agreed on can prevent two people from walking away with different impressions of the same conversation.
Questions About Handling Difficult Conversations
Should I rehearse a difficult conversation?
It can help to think through your opening and identify two or three facts you need to discuss. Trying to memorize an entire conversation is less useful because you don't know what the other person will say. Know the issue, the examples, and what you hope will change. Leave room for an actual conversation after that.
What if the other person completely disagrees?
Ask them to explain what they see differently. You may have information they don't, or you may disagree about what happened. Keep returning to the specific issue instead of collecting old grievances along the way. If a decision still has to be made after you've heard their perspective, explain that decision clearly.
Does a successful conversation mean everyone leaves happy?
No. An employee can be unhappy about receiving feedback and still recognize that their supervisor handled the situation fairly. A better measure is whether both people understand the issue, had an opportunity to speak, and know what happens next.
Make Room for Better Business Conversations in Spokane
In our five-person business, the late-arrival issue doesn't have to result in an angry manager or an embarrassed employee. The owner raises the issue, learns something she didn't know, and leaves the conversation with a plan she can follow through on.
Small business owners have these conversations with employees, partners, contractors, and clients every day. Burbity Workspaces provides coworking(opens in new tab), private offices, and meeting spaces, giving local professionals places to work, meet, and handle the conversations that need a little more privacy. Explore Burbity Workspaces in Spokane, Washington(opens in new tab), to find a workspace that fits your business.
