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February 7, 2019

Do You Dare to Have Tough Conversations?

Faye Bradshaw

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The person is standing right in front of you. The words are in your throat, but they won’t come out. “It might make things worse.” “What if I say the wrong thing?” “I might shoot myself in the foot.” Then, once again, the moment is gone. Your chance to have a tough conversation has passed. “Next time, next time, I’ll say something.” But will you?

Have you ever buried your head in the sand and avoided a conversation? Perhaps you were afraid of the response. At times like this you keep putting it off, and you're flooded with dread and anxiety every time the issue rears its head.

When I was a junior executive, I spent weeks mustering the courage to approach my director, Lisa. Things were tense. We all knew she was going through a stressful house move, and all she seemed to do was field personal calls, then leave work early. I was handling some huge accounts and I felt alone, out of my depth, and increasingly frustrated at the lack of support and constant ball-dropping on Lisa’s side.

But the thought of asking for help – and criticizing her – was terrifying.

Step Out of Your Comfort Zone

Whether the tough conversation is with an employee, a colleague, a boss, a partner, or a friend, it’s not a comfortable thing to do. Especially for people-pleasing conflict-haters like me!

Maybe you tried to tackle an issue before, and it did make things worse. But tough conversations are sometimes necessary. For example, you could be asking for a raise, challenging someone on their frequent lateness, or confronting a colleague or boss about micromanagement or unfair criticism.

If you’re a manager, it’s your responsibility to tackle difficult issues. You might be expressing your disagreement with a strategy, or telling someone that they didn’t get the promotion they wanted, or that they’re being let go.

Don't Suffer in Silence

But, if there’s one thing worse than having the conversation, it’s not having it, and carrying on in tortured silence.

When you avoid the issue, your personal performance, team dynamics and business operations can all suffer. You may lose out on professional opportunities. And you could even find yourself snapping at loved ones at home. Whispered complaints to colleagues won’t solve the problem: the only reliable solution is to confront it.

When I finally spoke to Lisa, and she understood my view, I felt like a physical weight slid off of my shoulders. I slept so well that night, knowing that we’d taken a step forward, solved a problem, and built trust.

How to Handle Tough Conversations

There’s no magic formula for making difficult conversations easy. But there are steps that you can take to ensure that they go as smoothly as possible:

1. Plan It Out

Don’t try to "wing" a difficult conversation – you risk becoming flustered or overemotional. First, think about why you’re having it, and your desired outcome. Focus on helping the person to improve their behavior, or on expressing your own needs.

Next, plan for their possible reactions and responses. You could even try some roleplay. David Rock’s SCARF model can help you to frame your tough conversations in a way that avoids triggering negative reactions to a perceived threat.

Choose an appropriate time and place to chat. Don't ambush someone when they are clearly stressed, or when they're rushing home, for example. And don’t schedule a conversation too far into the future. You risk making the other person anxious if they have to wait too long to hear what you have to say.

It’s best to pick a neutral location; perhaps the coffee shop down the road, or a quiet meeting room. Aim to keep everyone at the same eye level, as this helps people to feel safe, engaged and comfortable. And consider whether you’ll need a witness or mediator.

2. Be Direct, But Choose Your Words Carefully

Address issues quickly, as they arise. Don’t let them pile up. Open with nonthreatening statements like, “I’d like to talk with you about…” “I think we have different ideas about…” or “I need your help with….”

Also, remember that tough conversations are about resolution, not stepping into the ring to “have it out.” Be honest, thorough, and illustrate your points with clear examples. If you’re delivering negative feedback, for example, be descriptive and factual: “When you do X, it has Y effect on me, and causes me to think and feel Z.”

Don’t swear or make threats, and avoid generalizations like “never,” “always,” “everything,” and “nothing.” This can make the listener feel attacked, and they might shut down or become aggressive in response. Continually asking “why?” can make people feel defensive, too, so stick to open questions.

3. Show Empathy, But Don’t Get Overemotional

Emotional intelligence is hugely important when you're having tough conversations. Try adopting a "Savvy Conversation" approach to avoid conflict, and, if you feel ignored, hurt, embarrassed, or intimidated, recognize that this may not have been the other person’s intention.

Try not to let personal feelings steer the conversation. Drop your assumptions and go in with an open mind. Breathe, stay calm, keep an even, professional tone at all times, and be respectful, even if you don’t agree with someone.

I’ve seen what happens when you don’t! My former colleague, Anna, was consistently rude to customers and other employees. Our manager relayed this feedback very aggressively, even pointing a literal finger. Anna swore, screamed, and stormed out of the office. It was a horrible day.

Call a “time out” if things become heated. Taking a step back gets heart rates down, and helps to prevent people saying things they'll later regret. And don’t ignore tears if they start to roll. They're a sign that someone is struggling. Instead, acknowledge the person's emotions, and give them some time to collect their thoughts.

You can also disarm negative behavior by calling it out. For example, if someone won’t speak or make eye contact after receiving criticism, ask them to help you understand their silence. If you’re an extrovert who gets anxious during silences, be wary of conversational steamrolling. Introverts need time to think and reflect before they speak.

4. Focus on Listening

Your priority during tough conversations is to listen and observe. Pay attention to body language as well as verbal cues, and respond appropriately. Allow the other person to tell their side of the story. Ask for feedback, and encourage them to ask questions, too. This will help them to process everything you’ve said, and you can clarify any misunderstandings on the spot.

But don’t interrupt, like my old manager, Chris. He would cut you off halfway through every single sentence. It became an office joke, but one that was more infuriating and upsetting than funny. I left every conversation feeling annoyed and completely unheard.

And thinking about what you’re going to say next doesn’t count as listening, either – people can usually tell.

5. Plan a Solution

The purpose of tough conversations is to take a positive step toward building a stronger relationship. It’s not about proving who’s right or wrong. Focus on ending the conversation in a positive, productive way, with clear action points that will help everyone to reach the desired outcome.

Acknowledge any awkwardness, and identify potential obstacles. Discuss how you’ll overcome them, and how you’ll provide support and evaluate the actions you've agreed. If there are deeper issues at play, such as mental health struggles, seek HR support.

Stay Positive!

You can never know what someone’s reaction will be during a tough conversation. But, by planning ahead, you can prepare yourself to handle the conversation in a compassionate and considered way.

It’s important to be honest, direct and respectful, and to ask for feedback, despite any potential embarrassment, disagreement or strong emotions. When you have those tough conversations in a positive way, you can nip all sorts of problems in the bud. Everyone will feel better for it!


Have you ever avoided a tough conversation because you were scared of the outcome? What happened when you finally plucked up the courage? Share your experiences in the Comments box, below.

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