The Most Difficult Job of a Manager: Difficult Conversations
I did many things well as a manager, but I struggled with “difficult conversations.” So I brought in some experts to give me and readers of this newsletter some advice.
Undoubtedly, any conversation considered “difficult” — including performance issues, behavioral problems, compensation and promotions, upcoming organizational changes or layoffs, etc. — is going to be emotional.
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You, as the manager, will be likely managing your own emotions, especially if you are conflict averse, but the person across the table or zoom call will have their own emotions.
Emotional conversations are where human relationships break down: it becomes harder to help someone, communicate effectively, and resolve differences.
It’s no wonder that hard conversations are often the “conversation of last resort.” Amazingly, 70 percent of employees do their best to avoid hard conversations. At the same time, of all the things a manager does, a difficult conversation is regarded as the “most difficult” aspect of managing.
For first-time managers, difficult discussions are where the rubber meets the road. It’s your first real test as a manager. It’s easy to give good news. It’s a whole new game to discuss a challenging scenario.
And because so much is changing in the workforce today because of AI — the reason I call this newsletter Managing in the Age of Uncertainty — it is inevitable that every manager in 2026 will have some kind of difficult, and potentially emotional, conversation with people in their organizations.
Are you ready for difficult conversations? Do you know how to handle your emotions and the emotions of the people you’re talking with? Do you have a plan?
Keep in mind that 50+ percent of all managers receive no formal training — so I’m devoting this entire newsletter sharing best practices from of the best coaches out there.
I just want to say I don’t include myself as having any special skills in this area of managing. Having said that, I’ve experienced all of them: layoffs, terminations, confrontations, disappointment, passive-aggressiveness.
Here’s what I learned in all these experiences: get the to point; don’t have any wind up whatsoever; try to finish in under 60 seconds no matter what the situation; practice; and practice again; try as hard as possible to be in tune with how you’re feeling in real-time; don’t let your emotions get the best of you.
So thanks to cassie, Michelle M. Bowman, Loretta Stagnitto and Amy Haworth for their insights. Each one offers big picture thoughts and some key tactics to make the conversations as productivity as possible:
Cassie: “Generally I try and not wait and let issues compound (makes it much harder).”
For conversations themselves, I probably always focus on these areas:
- Anchor the conversation in care (e.g. shared goals, the person’s success or success of partnership, etc.)
- Describe specifics of behavior and impact ensuring it doesn’t feel like an attack on the person (e.g. you missed this deadline vs. you aren’t committed).
- Keep it simple (e.g. just say it without a lot of extra content, use plain language, etc).
Bonus - I love making it a walk and talk where possible/appropriate. Lots of data behind why walks are good to be side-by-side vs face to face and how that emphasizes collaboration, as well as just being calming for both.
Loretta: If you feel a fight-or-flight response, check your mindset; take a pause and breathe deeply.
- Be mentally and physically present.
- Use active listening.
- Acknowledge and paraphrase the message: “I want to make sure I understand your view on…”
- Acknowledge the other’s feelings: “I can see this has been frustrating for you.”
- Check your perceptions and interpretations by remaining curious and asking open-ended questions.
- Acknowledge your limitations and actions: “I recognize that I…”
- Use open body language; avoid crossing arms and legs, and maintain eye contact.
Bonus: Don’t react; remember, between trigger and reaction, there is a space. Use that space to pause, diagnose, and then respond.
Michelle: Getting started is often the hardest part. “I wanted to get your take on this…” is a good way to start, especially if you are asking in an email for a face-to-face meeting about a difficult situation. I’ve had Post-its left on my desk that say, “See me”, or in an email, “I’d like to talk to you about something…” Both are vague and anxiety-producing!
- Clarify the goal of the conversation, state whether it is project feedback, a behavior, or a company decision. You might say, “I care about you and want to tell you what’s going on with the company”, or “I want to share what I observed in the meeting today...”
- If it’s a general concern conversation, don’t start with, “you seem frustrated…” that will likely put them on the defensive to explain. Better to say, “I wanted to check in on how you are feeling about/dealing with X…”
- Be specific about your observation of their behavior. You might say, “When we discussed our approach in the meeting, you agreed to it and said fine, but later I heard you raised concerns and issues with a coworker.”
- Use “and” not “but”… especially with sandwich feedback. “I value your work and want to work well together…” instead of, “I value your input, but you need to raise issues directly with me, not others.” Saying ‘and’ keeps them interested and listening; “but” is waiting for the next shoe to drop.
- If they act defensively. Don’t just say, “I want to get your perspective,” show it by listening, asking questions (seeking to understand), and most importantly, reflecting back on what you heard. If they are giving some solutions, take note of them. You may also follow up the conversation with a summary of the discussion and any agreed-upon actions.
Bonus: If you are laying someone off, don’t bury the lead. Start with admitting that “this may be a difficult conversation…” and be clear, direct and respectful from the beginning.
Amy: Having a successful difficult conversation requires authentic care for the individual.
- The most useful framing is to share feedback by addressing the impact that a behavior, a decision, or a mindset is having.
- Surfacing observation of the impact allows the issue to be viewed as an item to be examined rather than an affront to the personhood of the individual receiving the conversation.
- And, most of all - realizing that the difficulty is constructed in relationship with each other. So, therefore, we ourselves might be part of the problem.
Bonus: The energy we bring is essential. Energy cannot be seen, but it can be felt. Are we judgmental or curious? That orientation alone can be the difference between a conversation going well or poorly. In the words of the renowned Crucial Conversations work: “Start with Heart”.
Homework: Learn, Be Ready
Some form a difficult conversation in the life of a manager is inevitable. Your homework as a manager is to learn from these experts. Everyone is different and has their own approach to things. But no one can predict how a hard conversation is going to go.
What I can predict is that you can’t “wing it.” I learned something critically important from all four coaches: I have spent of a lot of my energy in difficult conversations thinking about my feelings — what I learned from Cassie, Loretta, Michelle and Amy is this: I need to put a lot more emphasis on acknowledging the feelings of the person I’m talking to.
What did you learn? How ready are you?
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In Summary: Principles of Managing in the Age of Uncertainty
- I left Cisco to answer this question with research and evidence: What does the manager of the future look like? What are millennials and gen-z seeking in a manager? Which behaviors, tactics, skills or processes matter? What’s it going to take to attract and keep the best people over the next decade? In short, how to be a great manager.
- Based on this research, the core philosophy of this newsletter is rooted in one idea: successful managers in this moment in time, for this generation of talent, need to be “career dot-connectors.” The next-gen doesn’t expect to spend their entire career on your team — that’s an idea boomers grew up with. A job on your team is like a chapter in a career story to the current generation. If you want the best people on your team, you have to connect the dots between roles on the team and the career opportunities of the people working on the team.
- What is the“Age of Uncertainty”? If the industrial age was about taking predictable steps up the ladder, the age of uncertainty is about finding or discovering the path of a career without any predictable steps, without an obvious ladder — it’s why being a career dot-connector will differentiate you as a manager.
- How to be a Great Manager in the Age of Uncertainty: Be a Career Dot Connector is available on Amazon.
- What kind of manager are you? Take my free self-assessment and learn about yourself.
