Five tips for handling difficult conversations

Let’s be honest, most of us dread difficult conversations. Whether it’s delivering bad news to an employee, discussing a sensitive topic with a friend, addressing your manager about a necessary change, or facing other challenges, you are not alone. According to research from Bravely, 70% of employees avoid difficult conversations at work, and 53% handle “toxic” situations by ignoring them.

Just the thought of having a difficult conversation can be stressful. You worry about it, lose sleep over it, and it looms over you like a shadow until the conversation is had. You know it needs to be done but try to postpone it, making it hard to truly relax. Fortunately, there are tools to make these conversations more comfortable, leaving you feeling relieved afterward.

Tip 1: Address your fear

Many of us try to avoid the things we fear, and if fear is the root cause of avoiding difficult conversations, it’s understandable why you would want to avoid them. You are not alone, and more leaders probably experience this than you might imagine. Leaders we work with have identified three main fears:

1. Fear of rejection: What will the other person think of me? So you deliver your message to vaguely or with a joke. 
2. Fear of the impact on the other person: I don’t want to hurt my colleague. For some, upsetting someone makes them feel guilty, like they are a bad person.
3. Fear for the relationship: We have to work together every day. Will this create tension between us?

How do you convey your message clearly while maintaining or even improving the relationship?

Instead of avoiding difficult conversations, express your fears openly. We call this a ‘concern statement’. 

For example, if an employee’s project didn’t go well and they blame others, you, as a leader, see that they also had a part in it. The concern statement: “I don’t want to strain our collaboration. The way you’re explaining this to me shows that you also had a part in the project going wrong. 

“I feel nervous bringing this up because I don’t want to hurt your feelings, however it’s important to discuss the impact of the recent policy changes on our team.”

Tip 2: Prepare using the 3-2-1 method

Delivering a difficult message without knowing how can be challenging. Start well-prepared so you know what you want the other person to hear and take away from the conversation. Avoid having your feedback perceived as an attack by preparing it in three steps:

1. Imagine the person sitting in front of you: Say everything you want to say unfiltered.
2. Sit opposite them in your mind: Now, speak to the person. The message will already be more nuanced. Try to feel some resonance with the other.
3. Take the person’s perspective: Imagine being the other person, taking their viewpoint, and receiving what you just said.

Communicate from yourself. Use phrases like "Here’s what I’m struggling with" instead of "You must not..."

Tip 3: Embrace defensive behavior

Even if you phrase your message well, criticism triggers our underlying vulnerability. This is due to the dominance of our limbic system, the most primitive part of our brain. It reacts to perceived danger or threat by producing stress hormones, which can either cloud our processing of information or make us defensive. This can evoke thoughts like: “I’m not good enough.” “I did something wrong.”his triggers classic defensive responses: “Yes, but…” or “That’s just how I am.”

Expect resistance: embrace it! Be aware of the aspects you will activate in the other person. You’re not only talking to a colleague but also to their inner vulnerability or inner critic. Anticipate a reaction from that standpoint.

Defensive Behavior isn’t resistant to interest Defensive behavior only resists attack.

When your colleague explains why they did something a certain way, acknowledge their good intentions. State that their good intentions are not in question. You want to look at the impact of their behavior. Also, make yourself vulnerable by asking how you contributed to the situation.

Tip 4: Clear is kind, unclear is unkind

A difficult conversation is actually a gift. It shows you value the relationship with the other person. You have the courage to face uncomfortable feelings and aim for a better outcome. Be clear about what you want to say, preferably in four short, clear sentences.

Using too many words often masks insecurity, and your message risks getting lost in a flood of words. According to Brené Brown, “Clear is kind, unclear is unkind.” When what you say and do aligns with what you think and feel, others know where they stand with you. This gives your team the sense that they can trust and rely on you. As a leader, you are empowered when you can clearly state where you stand.

Tip 5: Speak your mind with vulnerability and sensitivity

Say what you want to say, but in a way that remains connected to your vulnerability and sensitivity. Be mindful of your own and the other’s vulnerabilities. At the same time, make your boundaries clear and check the boundaries of the other person.

Only have the conversation when you can do it with an open heart. No matter how tense you feel, approach the other person with an open and generous mindset, assuming their good intentions.

“Sarah, I’d like to talk about something that’s been on my mind. I feel a bit anxious bringing this up because I value our working relationship and your contributions to the team. 

I deeply respect your leadership and feel a bit vulnerable bringing this up, however I think it's important to discuss how the recent policy changes are affecting team morale and productivity.

Ready to transform your leadership skills?

Handling difficult conversations with grace and confidence is a crucial skill for any leader. If you’re ready to take your leadership to the next level, visit our website and explore our comprehensive leadership program.

Our program is designed specifically for women leaders and solopreneurs, providing the tools and strategies to navigate challenging situations while maintaining strong, positive relationships. Join a community of like-minded women dedicated to personal and professional growth.

Take the next step in your leadership journey today. Click here to learn more and sign up for our leadership program. Embrace your potential and become the magnetic leader you were meant to be!