The small business guide to managing difficult conversations with your team

Published on October 23, 2024 by Michelle Martin

Michelle sits behind a wooden desk and has her laptop open. She is facing the computer and speaking to someone virtually.

If you’re avoiding having a difficult conversation with an employee, these tips will help you talk to them with confidence so that you can resolve the issue.

In your role as a leader, managing conflict at work is an unpleasant but unavoidable part of owning a company. At some point, you’ll need to have a difficult conversation to fix a problem and get things in your business to run smoothly again.

Maybe an employee keeps missing deadlines or a team member is giving major attitude. Perhaps a new hire repeatedly turns in sloppy work or a manager blames everyone else for their team’s shortcomings.

Often, it’s obvious when you need to sit down with an employee for a one-to-one chat; but sometimes you may not realize it or be unwilling to admit to yourself that an intervention is needed.

You’ll know it’s time to have a tough conversation when:

  • You’re not getting the results you want.
  • The same problems keep coming up.
  • You find yourself doing the work your team is responsible for.
  • You keep on being frustrated with your team. If you find yourself thinking things like, “We already covered it in the policy, why aren’t they just doing it?” or “They’ve seen me do this a thousand times; they should know how it works” — that’s a sure sign.

But knowing you have to have a discussion is the easiest part — navigating through conflict is where things get tough. You worry about saying the right thing in the right way, and just thinking about the conversation triggers physical symptoms like a racing heart and sweaty palms. 

And because you anticipate the difficulty, you avoid talking to the person. You put it off or try to find ways around it. But eventually you’ll have to deal with the situation because nothing will change if you don’t make changes. And the sooner, the better, or you risk things getting worse.

Missed deadlines or sloppy work could mean lost business. Attitude problems or an unaccountable manager can create a toxic work environment. Every issue you walk past, you enable. be an effective leader is to practice effective communication in the workplace — you need to deal with problems as they come up so that your business can function properly.

But how do you get yourself ready for a difficult conversation so that you don’t freeze in the moment, get nauseous or make things worse? With the right preparation and using the following techniques for managing challenging conversations, you’ll be able to resolve conflicts and provide employee feedback with more confidence and increase the odds of getting effective results. Here’s how.

Three questions to get yourself ready for a difficult conversation 

You wouldn’t pitch a new client or make a presentation to the board without preparing first. By planning ahead, you equip yourself to face a stressful situation with grace and competence. Likewise, getting ready for a tough conversation with an employee will improve your ability to manage your emotions in the moment and clearly communicate the issues and find a solution.

Before you approach the problem employee, ask yourself these three questions.

Question 1: What story are you telling yourself about the conflict?

It’s easy to jump to conclusions and vilify others, but are you letting your emotions or personal bias dictate the narrative? Making assumptions about the situation or other people’s intentions will block you from making real progress.

For example, is Mike blowing his deadlines because he’s irresponsible and unorganized, or is he overburdened with assignments? Does Emily not care about the quality of her work, or did she not get the proper training?

To counteract false conclusions, approach the conflict with curiosity. Ask yourself: “Why would a reasonable, rational person do this? If I trusted and respected this person, what thoughts would I have?”

In asking yourself this, you might find your thoughts about someone who misses work all the time go from “this person is so lazy” to “I hope they’re ok, I’d better check,” for example.

By acknowledging the story you’re telling yourself about the conflict, you’ll be better equipped to properly address the situation.

Question 2: What’s the true goal of having the conversation?

Once you’ve mastered the story you’ve been telling yourself about the conflict, you’re ready to determine the true objective of having the conversation.

To figure this out, start by asking, “What is the real problem and why is it such a tension point?” For example, you might have identified the problem as “Mike doesn’t do his job,” but the real issue is that Mike keeps missing his deadlines, which puts everyone else behind or forces them to work into the evenings and weekends.

To quote inventor Charles Kettering, “A problem well stated is half solved.” Specificity is clarity.

From there, you can distill the goal of the conversation. In this example, the true goal is to figure out how to help Mike meet his deadlines so that his colleagues aren’t negatively impacted.

As you work to identify the goal of the conversation (as well as later, when you talk to your employee), be sure to monitor the intent in your heart. Being the compassionate leader you are, you shouldn’t be looking for a “gotcha” moment. Instead you want to take this opportunity to help your team.

This True Goal will be the North Star for the conversation. How do you honour the company, yourself and the other person? What do you need for all three in order to come up with a productive resolution?

Question 3: What’s your role in the conflict?

This final question requires some deep internal soul searching. Ask yourself, “What am I pretending not to notice about my role in the situation?”

Could you have addressed the issue sooner? Do your employees have inadequate resources? Are you clearly communicating your expectations?

There’s always a role you play in the conflict, even if you’ve just been ignoring it. This isn’t about laying fault or blame, but about taking responsibility. It may feel uncomfortable at first, but be honest with yourself and you’ll find answering this question is empowering. It helps you gain perspective on what you can control and enables strong leadership.

By looking at how you might be contributing to the situation, you move from being the judge, jury and executioner to being able to constructively find a solution. 

4 steps to navigating difficult conversations

After you’ve asked yourself the three self-probing questions, you’re ready to prepare for and have the difficult conversation with your employee.

Step 1: Plan out the discussion

Have you already run through the conversation in your head, imagining what you’re going to say? That’s where most people stop. 

The key to success is to write out your plan. This will help dissipate your feelings about the conflict so that you can be less emotionally triggered in the moment, when you’re actually having the conversation.

Write out your answers to the above questions as well as details on how you plan to start the conversation and what the solution might look like.

For a full conversation-planning guide, download my “From Conflict to Connection” worksheet".

To truly get comfortable with providing effective feedback, role play — either in front of a mirror or with someone else. The more you plan and practice, the less likely you’ll get flustered during the actual conversation and forget what you were going to say. You may be stressed, but you’ll feel confident that you have a plan.

Step 2: Ask for permission to talk

The kindest thing you can do as a leader is to give your employee a chance to emotionally prepare for the conversation. Surprising them will only escalate the conflict.

This means you don’t attack them with an accusation in the hallway or call them to your office and immediately launch into the conversation.

Think carefully about how and when you’re going to ask. For example, “Do you have a moment later today when we can discuss project deadlines?” is much better than scheduling a mystery meeting for first-thing Monday morning, late on a Friday afternoon. Do that and your employee will be stressing out all weekend that they’re going to get fired.

Step 3: Acknowledge them, advocate for yourself

When you have the conversation with your employee, embrace the power of curiosity. This is your opportunity to find out how they view the situation and to discover if you’re missing key information.

For example, by approaching the conversation with curiosity, you’ve discovered that Mike always misses deadlines because he receives requests from two departments, but neither is aware that he’s helping out the other team. No one knew the extent of his workload and he hasn’t felt empowered enough to push back on deadlines when there are competing priorities.

As management consultant and author of The Five Dysfunctions of a Team Patrick Lencioni would say, you’ve now given Mike the opportunity to feel seen, heard and understood. This builds trust and enables you to support Mike with specificity so that a successful change is more likely.

Once you’ve heard your employee’s perspective, you can clarify your viewpoint — without minimizing theirs — then start looking for a solution to the problem.

Step 4: Solve the problem and commit to action

Using your answers to the three questions above and your written plan, discuss the issue with your employee and work together on solving the problem. Remember: You have a role to play here as an impactful leader. It’s not just about your employee changing their behaviour on their own.

As you’ve discovered, the solution to Mike missing his deadlines will require help — and buy-in — from two departments, better communication from Mike, and possibly facilitation from you.

Once you’ve landed on a solution, be sure to get commitment — who's doing what by when, and who's following up when? There needs to be accountability in order to see change.

Get better at having difficult conversations with employees

Conflict resolution is rarely easy, but download the worksheet “From Conflict to Connection” and follow the tips above, and you’ll be well on your way to being more comfortable having difficult conversations with your employees. With time and practice, you’ll become more confident and feel more capable. 

The key is to approach every difficult conversation the same way you would want an ER doctor to treat you: Be compassionate and support the person you’re talking to — make them feel seen, heard and understood — and then manage the problem.

Michelle Nicole Martin
Leadership Coach & Consultant
Top Small Business Voice on LinkedIn
linkedin facebook pinterest youtube rss twitter instagram facebook-blank rss-blank linkedin-blank pinterest youtube twitter instagram