How To Handle Difficult Conversations
Part of your job as a manager is having tough conversations.
It took me a while to understand this quote:
“Leadership is the art of disappointing people at a rate they can stand”
Most leaders are well-intentioned, good people who fall into the trap of trying to please everyone. They try to balance doing what’s right for individuals, the team, their management, and the business.
You want everyone to get along and perform at their best. You want to give everyone exciting projects, more pay, and a promotion. But you operate in the real world. There are limited budgets, people are complex, the important work that needs to be done isn’t always exciting, and some decisions are not under your control.
Here’s the truth: You can’t make everyone happy.
Tough Conversations
"When we avoid difficult conversations, we trade short-term discomfort for long-term dysfunction." Peter Bromberg
As an engineering manager, tough conversations are part of the job. Whether you're giving difficult feedback, discussing a project that's fallen behind, or resolving a conflict between team members, these conversations will feel uncomfortable.
There are a few common types of difficult conversations you may face as a manager:
Compensation discussions
Promotions (or lack thereof)
Performance
Interpersonal and team conflicts
Even though they’re not easy, these conversations are crucial. They help you address problems, support the interests of the wider team, and help your organisation succeed. As an engineering manager, learning to handle these conversations confidently can make a big difference in your team's performance over time.
Simply put - having tough conversations is a part of your job. If you’re avoiding them, you’re not doing your job.
Note that this is harder for some people than others. I’m a natural introvert. I dislike conflict. But, like most things in life, handling tough conversations is a skill you can learn.
The following is advice from my own experiences.
How To Handle Difficult Conversations
1. Be Prepared
Preparation is key when it comes to difficult conversations. Know precisely what you need to discuss, anticipate how the other person might respond, and back up your points with data.
2. Stick to the Facts (Use SBI)
The SBI model (Situation, Behaviour, Impact) is a good way to structure your feedback. It helps keep the conversation grounded in facts, not opinions.
Situation: What happened?
Behaviour: What did the person do?
Impact: What was the result of that behaviour?
Example:
S: “I’d like to talk about this morning’s meeting about the project status.”
B: “When asked about the deadline, you avoided the question and ended the meeting early.”
I: “Now the leadership team is unclear on progress, and other teams are being held up.”
3. Be Clear, Direct, And Transparent
The more complex the issue, the more direct you should be. Don’t sugarcoat things or dance around the subject. Say what you need to say, and stick to the facts.
Be authentic, honest, and transparent.
Don’t give positive and negative feedback at the same time. It’s confusing.
4. Avoid Blame
Pointing fingers only makes people defensive. Instead, focus on the behaviour and its impact using the SBI model. Stick to observations, not accusations.
Use “I” statements to keep the tone less accusatory. For example:
Bad: “You never attend standups.”
Better: “I noticed you didn’t attend standups for the past few days. Why is that?”
5. Active Listening And Empathy
In difficult conversations, most people are busy thinking about how “they” feel. But to make progress, you need to listen. Focus on understanding their perspective, not just on making your point.
Ask clarifying questions like, “How do you see it?” to get their side of the story.
Listen with empathy.
6. Stay Calm
Difficult conversations can get emotional. Stay calm, and keep things productive. If emotions run high, it’s okay to suggest taking a break. Staying composed helps prevent the conversation from derailing.
7. Find a Win-Win
The goal isn’t to “win” the conversation—it’s to find a solution that works for both sides. Collaborate on finding a way forward rather than telling people what to do.
Ask for their suggestions, work together on the next steps, and ensure they take ownership of the plan.
8. Follow Up
Don’t leave the conversation hanging. Follow up afterwards to check progress, answer any lingering questions, or offer support. This shows that you care about resolving the issue and value the relationship.
Summary
Tough conversations are essential to leadership, but that doesn’t make them any easier.
With practice and preparation, you can turn these moments into opportunities for growth—for you, your team, and the organisation.
Get In Touch
I’d love to connect on LinkedIn.