I spend the majority of my day delivering good news. As a recruiting coordinator, saying things like “We’d like move you forward in the process,” “We’d like to bring you in to meet the team,” “You did a great job on your call, role play or presentation” is the best part of my job. It’s easy to send someone an email or get on the phone with them and say things that I know will make their day. It’s a lot harder to deliver bad news to candidates.

Difficult workplace conversations, however, span much more than just being rejected for a position or receiving constructive criticism from higher-ups. Making a big ask, pushing back on a manager, or realizing that the timing of an internal move might not align with your expectations are also difficult conversations to have, with yourself and with others.
When we don’t know how to approach a conversation that’s potentially disappointing, confrontational, or full of hard truths, we often take the easy way out. We stick our heads in the sand rather than facing the situation head-on. Other times, anticipating an awkward or uncomfortable situation, we have the conversation but deliver the message quickly (read: bluntly) without fully considering the other person’s feelings.

I believe there is a better way to communicate in these situations, and it involves being compassionate, clear, and committed. Over the past year at HubSpot, I’ve learned a lot about how to approach the tough stuff; here are my top takeaways for facing difficult conversations:

Communicate With Compassion

First and foremost, be a human. It sounds simple, but it’s easy to forget that there’s always another person on the other end of a conversation. We tend to lead with our own ideas, needs, and biases, but playing devil’s advocate against ourselves can help. In order to understand where someone else is coming from, you need to picture how they’ll experience what you have to say. What position are they in? What might they be fighting for? How difficult is this conversation on their end? And perhaps most importantly, how will what you say affect how they feel and how you work together in the future?

Looking at things from this perspective helps prevent us from framing conversations as a “me vs. you” or “us vs. them” situation. Broaching a difficult topic doesn’t have to mean that you’re sitting on different sides of a line or table. It’s hard not to feel divided but it’s important and much more effective to remind yourself that the universe (and likely, the person you’re sitting across from) is not out to get you. By choosing to believe this, you’ll approach conversations from the perspective of finding common ground.

Use Clear and Consistent Messaging  

In addition to being compassionate in your communication, it’s equally as important to be clear, whether you’re making an ask or delivering bad news. When making an ask, being clear about what you want helps the other person want to give it to you.  If you need someone to make time for you, you need to acknowledge how busy they are and the fact that you’re asking them to prioritize you above something else. If you want to be included in something, you need to lay out for someone why involving you has benefit - and then you need to do the work of making your presence known and helpful.

If you have a difficult message to deliver, that message should come directly from you - not from another team member, not overheard in a bathroom, and not read between the lines of an email. We’re all capable of letting our minds run wild, making assumptions, and twisting someone else’s words. Being clear and consistent prevents all of the above, and underscores the essential element of trust in a relationship. In other words: I should be able to trust that you’re going to tell me the truth, that I’m not going to hear it any other way, and that the way you tell me this truth is consistent with what I know about how you operate and how we work together.

Commit to Being Uncomfortable

As you’ve likely heard before, most things in life aren’t black and white. Accepting that fact can be uncomfortable because it forces us to reckon with the idea that right and wrong don’t cover everything. Sometimes, a conversation won’t be simple, a good explanation won’t exist, and you won’t have all (or any of) the answers. Learning to operate in this gray area requires you to commit to being uncomfortable.

In these moments, our instinct may be to talk about anything other than the topic at hand. It’s important to remind yourself to prioritize what you need to say, rather than what you want to say. For example, I’m a chronic over-apologizer. Saying ‘sorry’ is a crutch for me in situations where I’m uncomfortable. There are plenty of tough conversations where I want to apologize to soften a blow or make the other person feel better, but in doing so, I cloud the actual message. Others sit down to deliver feedback and make small talk about their weekends or their latest TV binge - anything to avoid the conversation ahead. What are your own conversational crutches? What’s the message you need someone to walk away with? It’s your responsibility to make sure they understand and receive it.

Even when you’re uncertain, challenge yourself to show up to the conversation. Bring your best self without an agenda or distractions and truly engage with the person sitting across from you. It’s likely that they are just as eager as you are to be doing anything else. Be there with them (and without email), even when it’s uncomfortable.

Leave People in Better Shape

Every time you have a tough conversation, you have a chance to make a positive impact. Whether you give someone necessary clarity, helpful information, or take the time to deliver your message in a distinctly human way, aim to leave people in better shape than you found them. We can’t control circumstances and we can’t control people, but we can control how we react to both, and how we leave others feeling after interacting with us.

In this way, we can all strive to be daymakers. A movement started and led by David Wagner defines a daymaker as “a person who performs acts of kindness with the intention of making the world a better place.” I’m intrigued by the idea that we can fulfill this ideal even in difficult moments. By challenging ourselves to be compassionate in all of our interactions, even the ones that we’d rather avoid, we can make others feel seen and known.

Although we all have tough conversations ahead of us, if we frame them differently, we can experience them differently. You can walk out of a room without feeling that you clammed up and didn’t express how you truly feel. You don’t have to regret treating someone with less warmth than you’d like because you weren’t sure how to approach a difficult topic with them. In the end, you can do hard things and you can say hard things, and you can do so with compassion, clarity, and commitment.

Originally published Aug 1, 2017 8:00:00 AM, updated January 18 2023