Tough Conversations Aren’t So Tough When You Know How to Have Them
If you’ve ever avoided a tough conversation because you didn’t know how to start it, this is for you. Today I’m releasing two new resources exclusively for paid subscribers, built around one of the most avoided moments in leadership: the tough conversation.
As a paid subscriber, what you’ll get:
The Confident Conversation Guide — the exact framework, script, and what to do when the conversation doesn’t go as planned. What to say when Taylor cries. What to say when she gets angry. What to say when she shuts down completely. You’ll walk in prepared for all of it.
The Confident Conversation Prep Sheet — a fillable worksheet that walks you through every step before you enter the room. The facts, the outcome, the script starter and a pre-conversation checklist so nothing gets missed.
Both are attached in the Leadership Toolkit. Download them, save them, and use them the next time you find yourself putting off a conversation you know you need to have or share them with a leader who struggles with the tough conversations.
Most leaders avoid tough conversations because they don’t know how to have them. They don’t know how to start it without it feeling like an ambush. They don’t know how to address a behavior. They don’t want tears. They don’t want emotion. It all sounds like a really undesirable situation, why would they run towards the fire?
But the impact of not having those conversations is astronomical and it doesn’t stay contained to one person. It starts with your team. They’re watching. They see you accept behavior you shouldn’t, and they draw their own conclusions. If you don’t care, why should they? That’s when people start checking out: they show up late, do the bare minimum and look for the exit. Absenteeism goes up. Quality goes down. And productivity suffers.
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And it doesn’t stop at your team. When the leader next to you sees you letting it slide, that message spreads. Why should they hold their people accountable if you aren’t holding yours? One unaddressed behavior and avoided conversation, that ripple goes further than you think.
The reason why leaders hold off on having these conversations is because they are approaching it as a correction. And that just sounds uncomfortable. But that’s not what it is, “The end goal should be to walk out of the room, linked arm and arm (figuratively speaking, don’t touch your colleagues, please) with a plan to move forward.
How you start the conversation is what determines the outcome. Approaching it from a connecting and seeking to understand perspective, lowers both of your guards a bit. Finding something in common to connect on, maybe something at work like a big project you both just finished or something outside of work or even what you had for lunch that day…. connection first is everything.
You’re not coming into the meeting to immediately correct the behavior. Your desired outcome for this conversation is to connect with the employee, understand what’s going on and to leave the conversation united on the way forward. That doesn’t sound like a negative experience for anyone, if you ask me. And let’s look at the results outside of the room, after that conversation is had. You’re creating a much more pleasant environment for all of your employees. You’re showing that behavior matters, and that bad behavior will not be tolerated. You’re showing that you care. You’re setting expectations. You’re holding people accountable, including yourself because you’re being courageous and having that tough conversation. The benefits of this single conversation go a long way to preserve your team and organization’s culture.
The simple shift from “You did this” to “Help me understand what’s going on…” leads the conversation to becoming a point to connect. You’re seeing the person, you’re seeking to understand the person and their behavior. As humans, isn’t that all we want? People to want to understand us?
So, let’s look at how we have this conversation, a simple step-by-step:
Connect - find some common ground with the employee. Whether that be a big project you both are working on or just finished, something going on with the kids at home (if you both have kids), maybe a recent vacation or even what you had for lunch. Connecting over our terrible lunch right after lunch was always something we could agree on and laugh about because the cafeteria food was so bad. It truly made me realize I ate for sustenance and not enjoyment.
Approach the topic - Once the connection is complete, you can approach the topic “The reason I wanted to get some time with you is…” and this could go a couple of ways depending on if you witnessed the behavior yourself or you have been told about it. Regardless, lead with facts. Perceptions are ok to share, as it’s important for the employee to understand what the team is perceiving, but always share that it’s a perception and never mention any names. Never make assumptions, it’s important to enter the conversation with a lens of seeking to understand and improve, not with the approach that they are already guilty before you even speak with them.
If you witnessed the behavior, it’s a much easier conversation, you can just say when, where and what you witnessed. “I wanted to chat about something I saw in the meeting on Tuesday. I noticed when Jamie asked a question, you shut it down pretty quickly. I wanted to understand what was going on there. Can you tell me about it?” This leaves the statement open-ended so the employee can speak about what happened, what they were thinking and feeling in that moment and why the behavior occurred. Maybe Jamie and the employee have been having conflict, but you weren’t aware of it, this allows that topic to surface. This works because it’s not accusatory, it’s not an immediate correction, it’s a seeking to understand from a place of care.
If you didn’t witness the bad behavior, but have received consistent feedback from colleagues, it’s still valid — but you’ll need to frame it differently. Your goal here is to share the complaints without naming names or starting a he said/she said battle. We want to make sure we can maintain the relationships between the team members outside of this room. This is when you say “I’ve been hearing from multiple people on the team that they’re feeling some tension. I haven’t seen it myself, but I wanted to talk to you to understand what’s going on from your perspective. Is there anything going on that I should be aware of?”
Ask open ended questions to gain as much information as you can and not limit the employee to what they can share. Allow them plenty of time to talk, but ensure you focus on the situation at hand and not “well, David did this 6 months ago…” Let them share their own perspective, what they believe happened, what’s leading to the bad attitude, etc. Let them fill the silence. Don’t be uncomfortable when there is silence…it’s important for you to take a breath and let Taylor talk.
3. Gather the facts. Not feelings. What truly happened? Exact situations that were witnessed can take the person back to that event so they can share what was going on that day. Behavior is observable. Stick to what you saw or what has been specifically reported.
If others have complained, but you haven’t seen anything yourself, just stating that “some colleagues have shared that there’s a tension with you.” helps to open the dialog to understand what is going on. The more details you can give, the better, but if you are getting multiple complaints from the team, you should still seek to understand what you can. If you witnessed it yourself, you can say something like “In our team meeting on Monday, when David asked for clarification, you told him to figure it out himself.” This is specific and a great example for you both to reflect back on. Ask “What was going on there?”
4. Connect Again. This provides another opportunity for connection. If Taylor explains that there is something going on at home, you can help support her with sharing resources, maybe the EAP where there are free therapy sessions or if it’s something that occurred at work that frustrated her, seek to understand what that was and if you need to address it with others. Opening this dialog is the purpose for this conversation.
You’re the leader and your job is to create a safe, productive environment for everyone. Even if she’s the one that’s been getting the complaints, getting to the bottom of it helps everyone. For example, if David is harassing colleagues and that’s why Taylor is behaving this way, you’re uncovering a bigger situation that needs to go to HR. If Taylor is just having a bad time, ask how you can support her in easing her attitude or behavior. And she may not know today, but letting her know that you want to help could lead to her coming back a week from now to share something she thought of that could be helpful. Or she may never come back with anything, but the behavior improves.
The conversation doesn’t end with you delivering expectations and walking out. It ends with both of you in the room, figuring out the path forward, together. You set the expectation. Taylor owns the behavior. Together you build the plan to make sure it doesn’t happen again.
5. How do we move forward from here? This is a mentor having a conversation with someone they believe in — not a manager issuing a warning. The tone you bring into the room and the approach you take will determine whether Taylor opens up or shuts down. Approaching it from a space of concern such as “I noticed this and I want to understand it” lands very differently than “you’re doing this and it needs to stop.”
There could very well be a place for “this needs to stop.” But this first conversation isn’t it.
I think we put too much emphasis on the thought of having the tough conversation and not enough emphasis on how to actually have it in a way that isn’t accusatory, but supportive. Leaders who avoid these conversations do so because they were never taught how to actually have them. These conversations are just another workplace meeting that needs to happen to move forward in the right way. And some can say these are the most important workplace meetings.