Not surprisingly, difficult conversations are, well… difficult. They’re also a necessary part of leadership, and it’s essential that new managers learn how to have them as quickly and effectively as possible.

Most of us dread having difficult conversations

Yep. I sure do. Even after managing teams for several years. Thankfully, there are ways to have difficult conversations that make them more manageable. As is often the case, if something makes your fight or flight response kick in, or in my case, "avoid-at-all-costs" instinct, a system to turn to may help.

A few key points before we focus on strategies. Don't procrastinate having them. In the same way timing is critical to giving feedback that is effective, putting difficult conversations off makes them harder to have the longer you wait to have them. I'm not advocating having “fly by” conversations, where it’s more likely one person will feel attacked or triggered. Rather, practice having them in a reasonable timeframe–one where the issue or topic is still fresh in both of your minds. It will help avoid confusion, frustration, and insecurity — all emotions that get in the way of a productive conversation.

Also key is to plan. Carefully craft your conversations beforehand. Reflect on how you’d like the conversation to go and how the other person might feel. Here are seven key strategies to help:

1. Frame it

Attitude isn’t everything, but it sure sets the tone and tenor. If you’re expecting a conversation to be difficult, adversarial, or challenging, chances are it will be. Take a few moments before you start the conversation to change your mindset from “I have to have this conversation,” to “I get to have this conversation”. It can make all the difference. 

2. Focus on the goal

Make sure you’re clear on what your goal is — and that the goal merits a conversation in the first place. Are you hoping to change a behavior, or just process something? If it’s the latter, ask yourself, "Do I really need to have this conversation?". Sometimes the answer will be yes, sometimes, no. If the answer is yes, identifying the ideal outcome can A., help you get to the root issue and B., help you anticipate anything that could be confusing or cause barriers to you really hearing each other.

3. Be honest

Clarify your intentions and then be super honest about them with yourself. Any pretense, intentional (or unintentional) ambiguity, and especially dishonesty, will make what you say ring inauthentic. Anything said is meaningless without trust. Lying or withholding information during your conversation will leave the issue unresolved and create new issues. 

4. Check your emotions

Will you be able to show up as your best self? If you’ll likely be anxious, frustrated, or at the mercy of your amygdala, hold off. Have the conversation soon, but take the time you need to have your emotions in check before you do. Write a letter to the person (don't send it!), go for a walk or run, pet your furry friend, or wait for the time of day you’re at your best. Both you and your counterpart will be better for it.

5. Embrace caring

One of the pillars of Kim Scott’s Radical Candor is to demonstrate care, and at Lead Belay, we agree it’s an essential part of any difficult conversation that goes smoothly. Difficult conversations are better when each feels heard, acknowledged, and cared for. Be intentional about thinking about how you will listen. What will your body language convey? (Don’t forget your facial expressions!) 

6. Make your expectations reasonable

Consider the chances that you’ll achieve your goal — and how you’ll react if you don’t. Conversation is two-way communication, and no matter how much planning you do, they’re likely to be somewhat different than you imagine. Consider if there are deal-breakers, if some of your goals might conflict with each other, or if there are smaller steps or ways you can work towards your ideal outcome if it can’t be reached immediately. 

7. End it with clear agreement

No conversation is successful if there are different interpretations of the outcome. It bears repeating: no conversation is successful if there are different interpretations of the outcome. When a conversation is finished, it’s critical to make certain you've made clear requests, and received clear acceptance of them. Summarize both verbally. Putting it in writing can also help serve as a reference for both of you. Without clarity, you’ll probably have the same conversation all over again soon.


Finally, think through these steps in the shoes of the other person. Keeping the other person in mind, imagine how they might react, and what their goals might be will help you prepare, and help you remember the cardinal rule of difficult conversations: this is not just about you. It’s about the immediate and long-term success of your team, your organization, and you.


Let's chat!

We'd love to hear from you!


Like it? Share it:

You may also like

Great Resignation woes? The cure is probably in plain sight.
Great Resignation woes? The cure is probably in plain sight.
1 December, 2021

If you’re in the people business you know all about the “Great Resignation.” They call it “great” for a reason. This yea...

5 common pitfalls of HiPo manager development (and how to avoid them)
5 common pitfalls of HiPo manager development (and how to avoid them)
28 September, 2021

This is a three-part series about high-potential managers. It's intended for organizational leaders and learning & d...

Avoiding Common Pitfalls for New Managers
Avoiding Common Pitfalls for New Managers
9 May, 2024

The transition from individual contributor to manager can be one of the most exciting times in anyone’s career. It can a...