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May 2024
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How to Have Those Awkward Conversations

You really can say anything to anyone when you’re prepared.

By Shari Harley


We’ve all been there. Someone does something irritating, off-putting, or upsetting, and we must decide to speak up or say nothing. We ask ourselves—is it worth it? Will the conversation make a difference? Will the behavior change? Do I even have the right to say anything? If I speak up, will I damage the relationship or make the situation worse?

If someone’s behavior is negatively impacting them, your organization, or you, it’s okay to say something. I regularly give speeches on the subject and even wrote a book on the topic, How to Say Anything to Anyone: Setting Expectations for Powerful Working Relationships. That said, there are a few things to consider before having an awkward conversation.

Who Are You Talking To?

First, ask yourself if you have the kind of relationship to give this person feedback. People are more receptive to negative feedback when they trust the person providing it. If you don’t have a trusting relationship, it’s very difficult to give feedback without damaging the relationship.

Second, evaluate whether the person is open to hearing the feedback. If they aren’t, it’s better to say nothing. When there is a lack of receptivity, you’ll be faced with resistance and won’t see behavior change. You can give feedback to a senior person at work, a fellow Toastmaster, a family member, or a friend, provided you have a trusting relationship with that person, and they are open to your feedback.

Let’s say the criteria for giving feedback are met—there is a significant impact on the person, on the organization, or on you; the person trusts you and your reasons for speaking up; and the person is open to your feedback. When all these things are true, how do you say what you want to say, and where and when do you have the conversation?

Preparation Is Key

If a conversation is going to be particularly difficult, write out what you want to say. Then save those notes as a draft and come back to them the next day. Your message might be different a day later when you’re feeling less emotional. Never give feedback when you’re upset.

Next, practice what you’re going to say out loud. Speaking words out loud and “saying” them in your head are not the same thing. Use your notes to guide you. Typed, bulleted notes, double spaced, with large font will help if the conversation becomes emotional or tense. Your handwritten notes will not help you during times of stress.

If you aren’t sure what to say, ask for help. Everyone but you will do a better job planning a hard conversation because other people aren’t emotionally involved. It’s our emotions that make feedback conversations difficult. If the situation is work related, ask for help from people outside your organization. Change the name of the person involved. Don’t increase the gossip that is pervasive in most organizations.

Time to Talk

Once you’ve typed out talking points, reviewed your notes when you’re not upset, practiced out loud, and possibly received some help planning the conversation, you’re ready to ask for time to talk. The location and timing of awkward conversations are essential to being heard, strengthening relationships, and seeing behavior change. Ask the person for time to talk. Always give negative feedback privately. Make sure the person can focus on the conversation and isn’t distracted by looming deadlines, an upcoming meeting, a vacation, or a sick family member. If the recipient is distracted, you’re talking for yourself and won’t see the receptivity or change you’re looking for.

You can give feedback in person, over the phone, or via video. Any of these mediums will work. Pick the medium that will allow you to provide feedback within a week or two of the event you want to address.

If the timing is right, you are both in a private place, and you’ve planned your conversation, it’s time to deliver the feedback. I always start difficult conversations by telling the person the reason I’m speaking up. It could sound something like, “I care about you and your career. I’m seeing something impact you negatively and I want to tell you.” Or “I care about you and our relationship. Something is impacting our relationship and I want to tell you about it.” Or “I need to talk with you. This might be awkward for both of us, but I’d rather you hear this from me than from someone else.” A phrase like this explains why you’re talking. You’re planting little seeds of trust. Because when people trust your motives, you can say anything. When people don’t trust your motives, nothing you say will get through.

Say This, Not That

Now it’s time to give examples. When you give feedback, provide one to three specific examples of the behaviors you saw the person exhibit. If you can’t give an example, you’re not ready to give feedback. Saying, “You hurt my feelings,” without telling the person what they said or did that hurt your feelings, only creates paranoia and defensiveness. Vague statements violate the purpose of giving feedback—which is to be helpful to another person.

If someone’s behavior is negatively impacting them,
your organization, or you, it’s okay to say something.

Instead of saying, “You’re sleeping on the job,” say, “You volunteered to run this year’s team builder. Our retreat is in 10 days, and I haven’t seen a plan yet. Is there something going on?” Instead of saying, “You’re taking advantage of our hospitality,” tell your house guest, “We love having you here. We’re happy to host you for the week. After that it would be best to find a hotel.” Instead of telling someone they’re a gossip, say, “I heard that you were talking about me to others in the club. This makes me feel like I can’t trust you. What’s happening?” Helpful feedback provides just the facts. Skip the subjective judgments, which increase defensiveness. Instead, focus on observable behaviors.

In my book, I call vague feedback Cap ’n Crunch. Vague feedback is just like the children’s breakfast cereal. It contains no nutritional value and leaves you feeling hungry 10 minutes after eating. Vague feedback leaves people confused, defensive, and wanting to know more. If you really want to help a person or alter a behavior or situation, you’ll be specific.

On the Defense

Now, let’s talk about defensiveness. Most people say they avoid giving feedback because they don’t want to hurt another person’s feelings, or they’re afraid the person will quit a volunteer or paid role. But what if we, the feedback provider, just don’t want to deal with the person yelling, crying, being angry, or giving us the six-months-long silent treatment?

Human beings get defensive when they receive feedback. Defensiveness is a normal, natural, and even healthy response to feedback. Human beings want to be seen as competent. Negative feedback calls our competence into question and the brain reacts, defending itself. When you give feedback, your job is to tell it how you see it. The listener’s job is to defend themselves. Defensiveness is a normal and predictable part of the feedback process. Instead of avoiding the person’s defensiveness, plan for it. Use your notes to bring the conversation back on track when the listener takes the conversation offtrack.

You really can say anything to anyone when people trust your motives and are open to your feedback. Prepare. Make typewritten notes, practice out loud, get help when you need it, and gather your courage. You can say more than you think you can.


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