How to Have Difficult Conversations at Work
How can managers and employees navigate difficult conversations with confidence?
One thing that follows us in every job and interaction at work is definitely difficult conversations. It can be so challenging that you might even leave a workplace because of them. However, it's important to understand that these tough conversations will arise again in your next role, especially as you settle in and grow within the position. Surprise: you can run, but you can’t hide!
Why Difficult Conversations Matter
‘‘The Job is Easy, People are Not’’ - Prof. Loredana Padurean
While it looks easier to ignore difficult conversations and think everything will go away, let me break it to you: it won't happen. These issues will turn into "small issues turned deep problems." When we don’t address them, they just pile up, and something that seems small to one person becomes unresolvable in the eyes of others.
It’s no surprise that this leads to lower productivity. You don’t need a Gallup study to realize that—just look inside your teams. How easy is it to get things done? Where do things fall apart, and most importantly, why do they fall apart?
Another side effect of not addressing difficult conversations at work is frustrated and unhappy employees. They feel unheard, misunderstood, burnt out, and disrespected. I’ve interviewed many candidates who started rage-applying to jobs after a situation where a difficult conversation didn't take place.
You should know that the first instinct for employees is to apply to other jobs. While I met many who withdrew from the interview process because the next week at work was much better, some left workplaces because they or their managers were afraid of tough conversations.
Tips for Managers to Handle Difficult Conversations
I know it might sound like a "duh!" moment, but managers should prepare in advance and get answers to these questions:
What do I want to achieve from this conversation?
Have I gathered all relevant information related to the issue?
If I were the other person, what concerns would I have if this information was presented to me?
Once you have your answers, it’s time to book that meeting. Here are some tips to help you rock it:
Find a Neutral Location: Choose a place where both parties feel comfortable (if you are conducting this in person).
State the Issue Clearly: Be specific about what the problem is and provide examples. Don’t beat around the bush. Employees can sense BS from miles away. You owe them transparency and honesty.
Avoid Overusing "I" Statements: This conversation is not about you, so avoid using "I" too much, as it will definitely sound accusatory.
Learn to Listen: Really listen—let the other person speak without interrupting. If you need to add your comments, do so at the end, addressing each point mentioned.
Show Empathy: Empathy doesn’t cost a penny. If you haven't experienced what the other person is going through, it doesn’t mean their feelings and emotions aren’t valid. Acknowledge their feelings.
Ask Questions: Clarify any points you don’t understand. You have to be on the same page.
Oh, great! The conversation becomes heated. NOW WHAT?
If the conversation is getting out of control, stay calm and composed. It’s perfectly okay to suggest taking a short break to cool down before continuing. This is not a wrestling match where someone has to take home a trophy.
You might not be entirely right after all. SAY WHAT?
Make it a team effort to brainstorm solutions. You might need to adjust your stance on some issues if it leads to a better outcome for both parties. Just because you went into the meeting thinking this is how it will turn out and be solved, you don’t have to stick to it!
At the end of the discussion, summarize what happened and what the action plan is: set it down on a piece of paper step by step.
Send an email—or it didn’t happen!
Following the conversation, send an email with the summary, action plan, and follow-up dates. This will avoid confusion about who said what and who agreed to what.
Tips for Employees to Handle Difficult Conversations at Work
I get it—you even hate the idea of saying it out loud to your manager. What if you lose your job? What if nothing changes? What about that promotion?
Just take a chance on you!
Your prep time starts by asking yourself these questions:
How does this issue affect me? Have specific examples (affecting your productivity, your mental and emotional well-being, your work quality, etc.).
What do I want to achieve from this conversation, and what outcome would make me feel satisfied?
What is my approach? Write down the key points you want to cover.
Here are your tips to nail the difficult conversation meeting:
Start with Gratitude: Show appreciation to the other person for their willingness to address the issue.
Stay Focused on YOUR Actions: Avoid bringing up past events that are not related to you, such as, “John did it but there was no issue when that happened with him.”
Be Specific and Avoid General Statements: Bring in numbers, dates, conversations, KPIs, etc., depending on what the conversation is about.
Your Ego is Not Your Friend: Own your part. Take responsibility, acknowledge your role, and express willingness to improve if any of your actions contributed to the issue. Don’t look for a scapegoat; this will definitely not solve your issue.
Language Matters: Avoid trigger words like “I never…” or “I always…”. Stick to the facts.
Ask Questions: You are in this meeting to facilitate a discussion. Ask open-ended questions.
Process Before Responding: Difficult conversations can be emotionally charged. Take a few seconds to process the information you received before responding.
Consider a Mediator: Some conversations might require a mediator. Do not hesitate to reach out to HR to join the conversation so both parties feel supported and heard.
Difficult conversations are not about finding someone to blame and moving on. It’s not a guilt game; it’s a sensitive space where each party is vulnerable but might feel like they are at war.
Teaching your managers and employees how to have difficult conversations at work will improve retention and problem-solving, allowing the team to focus on what they do best rather than on trivial things.
Lean on HR to organize some training sessions or hire a trainer who can come in every six months to support your team with classes, empowering them to have great conversations during difficult times.
If you enjoyed this article, feel free to connect with me on LinkedIn so we can continue the discussion there.
If you know an employee or a manager who doesn’t know where to start with having difficult conversations, share this!