Handling Difficult Conversations

Feb 1, 2021 | Human Resources

If you have employees, at some point you’ll end up having a conversation that’s necessary but uncomfortable. If you’re pushing yourself to meet your potential and be the leader you should be, you’ll probably have many of them.

You want to know a secret? Everyone hates them at first, but skillfully managing difficult conversations is something you can learn.


3 Keys to Success


1. Practice Makes Perfect

Conducting a difficult conversation is like a muscle you have to exercise. It’s painful at first, but the more you do it — the more you go to the gym and lift that weight of having a difficult conversation — the easier it gets.

I used to feel sick to my stomach before talking to an employee about something they were doing wrong. And I found that the more I did it, the easier it became. I developed skills I know work. Let’s look at them, so you can put them into practice.


 2. Don’t Stockpile Issues

It’s common for a manager to avoid having difficult conversations by stockpiling little issues. What happens, though, is you get to the point where you’ve had enough and you’re ready to simply terminate the employee — which isn’t good for either of you. The kind thing to do is let your employee know of an issue right away, so they can correct it.

In fact, I would be mortified if I were doing something wrong every day, but my manager never told me. I think most people feel the same way.


 3. Assume Positive Intent

Some of us operate this way naturally. Some of us have to train ourselves to use this perspective. Before a tough conversation with an employee, remember — most people want to do good work. Approach the conversation as if they simply need your help and leadership to understand and meet expectations.

For example, you notice a member of your front-office staff wearing tennis shoes, which is not in line with your dress code. What does assuming positive intent look like? Perhaps, because their feet are under the desk, they feel like their shoes don’t matter. You do care, however, because it doesn’t represent your brand.

Begin the conversation with the benefit of the doubt. In the case of a dress code, ask yourself the hard question, “Did I communicate my expectations?” If you haven’t, the conversation is easy: “Hey, Julie, I might not have mentioned our dress code. Here it is in our handbook. Would you give it a read and let me know if you have any questions?”

If it becomes clear that they do know what to do, and they just aren’t doing it, the situation becomes more complicated. Let’s look at ways to handle this.

Need help navigating difficult conversations with employees?

4 Common Conversation-Starter Pitfalls

You have to continue working closely with this person, so you probably don’t want to come off as mean or overbearing. Here are four starters that typically result in unsatisfactory results.


1. Being too vague

When you begin the conversation with, “How’s it going? Is there something wrong today, Julie?” you’re not identifying the problem. You want them to know you care, but now is not the time to hammer that home. Now is the time to get to the root of a behavior issue.


2. Using the compliment sandwich

This popular tactic, per conventional wisdom, assures the recipient they’re doing a great job, they just need to change this one thing. For example, “Julie, I love the way you walk around the counter and greet our patients. I don’t like that you’re wearing tennis shoes when you do it, but you do such a great job. You’re so warm.”

The compliment sandwich does two things: It negates the compliments and downplays the desired behavior change. It leaves your employee confused — “Am I good, or am I bad?”


3. Being too soft

Trying to soften the blow muddies the waters. Avoid constructions like, “Well, it really would be nice, Julie, if you could wear dress shoes to work.” Would it be nice, or is it your expectation? Julie will probably assume you’d really like it but aren’t requiring it.


4. Over-scripting

This is also a popular tactic. While I’m counseling a practice owner, they’ll say, “I’m going to write down everything you say, so I can say it exactly the same way.” Doing this takes you out of the moment with the employee — you end up listening to respond, rather than listening to understand. That’s never a good way to have an interaction with somebody.


What Success Looks Like


A Proven Strategy

The way I approach difficult conversations has proven fruitful time and again. It’s built around three statements — what, how, and why — and a follow-up question.


Simple example

What does this look like in our straightforward tennis shoe scenario?

  • What: “Julie, I notice that you’re wearing tennis shoes on a regular basis to work.”
  • How: “I would like you to wear closed-toed flats that are black or blue going forward.”
  • Why: “We offer a professional service, and our appearance is our brand, so it’s important that everybody dresses professionally in the office.”
  • Question: “I’m here to support you in this moving forward — do you have any questions or concerns about the dress code?”

The question invites a dialogue so you can learn about any obstacles to meeting your expectations. Your job, as a leader, is to help them surmount obstacles.


More complicated example

What if the performance issue is not so straightforward? Suppose one of your employees isn’t doing a very good job working a referral request into patient conversations.

  • What: “Julie, I noticed something yesterday. When I walked a patient up to the front, you checked them out but didn’t ask them if they knew anybody that could be helped by our services.”
  • How: “Next time, please ask if they had a great experience with Dr. Julie. If they say yes, ask them, ‘Is there anybody else who you know who would benefit from Dr. Julie’s services? If so, can I give you a card to pass along to them?’”
  • Why: “Some of our best patients come from referrals. It’s a very easy and effective way to drive patient flow, which helps us all succeed. Plus, it might help you hit your comp goal.”
  • Question: “What questions do you have about asking for referrals?”

Notice that along with my Why statement, I managed to make it relevant to their own goals. This is a more nuanced performance issue, so they’ll probably have a question or two for you.

  • Employee follow-up: “I don’t know what kind of patient I should ask for referrals. Should I ask every single one? Or have you already asked them? I just wasn’t quite sure.”
  • Your response: “Let’s assume that I won’t ask. You’ll ask every patient. My commitment to you is if it comes up in conversation during the consultation, I’ll signal you. When I walk the patient up to get checked out, I’ll say some kind of code word, like ‘Conversation’s been had.’ Something simple that clearly tells you that you don’t need to ask the question.”

You’ll notice I assumed good intent. I approached her as though she’d only neglected that one opportunity, and I was simply reminding her what I expect and why. But what if she’s someone I know is going to be defensive or contrary?

Approach every conversation with curiosity. I like to use a strategy I got from Brené Brown’s book Dare to Lead Sit next to your employee — not across from them — and have the issue on a piece of paper or in a guidebook. Place it physically between you on the desk or counter and say, “Hey, here is what I’ve noticed. How can we solve this problem together?”


Disciplinary Steps

Despite your best attempts, it could devolve into defensiveness, deflection, or feigning ignorance. It’s time to be the manager. Sometimes, you simply have to say, “This is my expectation. I’m happy to help you in any way you need. But this is the expectation going forward. If you can’t improve it, there will be further action.” It’s OK to be clear and decisive. And that brings us to discipline.


1. Verbal warning

This first conversation is considered a verbal warning. You don’t have to label it as such during the conversation — “Julie, you’re getting a verbal warning right now” — but you should jot a note down in your file that you discussed the issue. You could email the employee with a recap of your conversation to make sure you’re on the same page moving forward.


2. Written warning

If it continues happening, move to a written warning, or a corrective action. Before meeting with your employee, document the behavior and what needs to change, just like when you had the initial conversation. Also include what the consequences will be if further improvement isn’t made. Bring the written warning with you to the meeting, remind the employee that you already discussed this, then review what’s in the document. You both need to sign the document, but if the employee refuses to, that’s OK. Tell them that they don’t have to sign, but you’re going to notate the refusal, and your expectations will not change.


3. A potential final written warning

Under some circumstances, it’s warranted to issue a final warning. Be very clear that further behavior of this sort will result in termination. Document beforehand and get a signature. And then, of course, the last step is termination.


A Final Thought

I can’t stress this enough — document, document, document. Member practices will contact me with questions about moving right to termination, but they don’t have much documentation to show they clearly set expectations. If you have those conversations, document them so you have a record.


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