How to have a difficult conversation
© Pete Longworth
There is no easy way to start a difficult conversation.
When we have them, there are a few routes we can take: sugarcoating (where we sandwich the difficult part between overly positive parts so that it won’t feel as bad), avoiding (where we don’t talk about it at all and hope that maybe the issue will go away on its own, even when we know it won’t), or being real (where we shoot straight, are completely transparent, and build trust).
I’ve had to have a lot of difficult conversations with my team in the last few months. First, it was the decision to close Student Maid for two months because of COVID-19, which I knew would scare our team members and cause them to worry about the security of their jobs. Then it was the discussion with my leadership team about when/if we would have to take salary cuts (thankfully we haven’t had to, but we still talked about it). Then came the meetings where we had to decide how to best reopen Student Maid in a way that made everyone feel safe. And then, of course, came the most difficult and important one to date, where we talked about our stand against racism and the ways in which we can actively fight racism in our company.
Had any of this happened in the first few years of my leadership journey, I can promise you that I would have sugarcoated or avoided all of the above conversations. As an extremely positive, glass-half-full type of person who also had a need to be liked, I didn’t know how to start a difficult dialogue, and I was afraid to. I’m still afraid to, but over time, I learned that whenever I got the courage to lean into a tough convo, I immediately saw the trust on my team grow as well as their confidence in me as a leader. It eventually taught me that no matter how hard a topic was, I just needed to be real.
From the former Queen Sugarcoater and Avoider herself, here are my best tips to navigating difficult conversations:
Understand that it will not get easier: Once I understood that the point of difficult conversations wasn’t to make them easy, my mindset changed. They are going to be hard—always—and there isn’t anything you can do about that. Once you accept the fact that difficult conversations will always be difficult, it’s freeing.
Start right off the bat with a sentence like this: “We are here today to talk about a difficult subject, and that subject is X.” Just say it. Don’t do some weird, awkward intro that causes everyone to question what the conversation is about. Lean into it from the start.
Give everyone the space to share: A conversation means more than one person is talking. It’s up to you to start it, but that doesn’t mean it’s up to you to talk the entire time. If you are discussing an issue that affects someone, give them the chance to share how they feel. I always say something similar to this: “Now that I’ve shared, I’d love to give you the chance to share. How do you feel? What’s on your mind?” The more you invite other voices in, the better you will be able to face the challenge as a team.
Meet people with empathy: When it comes to difficult topics, everyone will process them differently, and everyone has a right to feel the way they feel. We must meet people with empathy, and that doesn’t mean changing how they feel; it means understanding and acknowledging the feelings they have. The best conversations happen without judgement and without someone attempting to manipulate emotions. It’s okay if someone is sad, upset, or afraid. They are allowed to be.
Get the fears out there: When having a conversation where there might be a lot of fear, it can help to have people say their fears out loud for a few reasons. First, it helps people realize they are not alone and that everyone is afraid. Second, sometimes when you talk about fears out loud, you take away the power they hold over you. The more we talk about our fears, the more we can talk about how we might navigate those fears as a team.
When people disagree, ask for support: Not everyone will agree with you, especially when it comes to change. And there’s the magical thing: Not everyone has to agree. In fact, if you are looking for consensus 100% of the time, it might prevent you from making progress and making the choices that you know are best. When I have reached 80% consensus on something, I will move forward. And when I do move forward, I will say something like this: “It’s okay if you disagree. What I would like to ask for is your support.” People can disagree with you and still support you.
After 13 years of leading a company, here’s what I can tell you with absolute certainty: People want the truth. They may get upset at the truth, but they want it. They don’t want you to BS them, they don’t want you to lie to them, they don’t want you to beat around the bush, and when there is a difficult issue looming that they are aware of and you aren’t talking about, they aren’t proud that you are their leader. In fact, it causes them to wonder what else you might not be sharing with them.
Now is a time we need leaders with the courage to lean in. What difficult conversations can you start?
Big hugs,
