Chad Silverstein argues that leaders who avoid hard conversations with people they care about cause more damage by waiting. He recommends confronting problems early and compassionately, building enough trust that teams can resolve things privately, and staying open to being wrong.
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One of the hardest things about being an entrepreneur is having to have really hard conversations, especially with people that you really like. It's just hard. You pour yourself into people you care so much. You become close with them, and you build relationships. And you work day in and day out, sometimes with them more than you are with people in your family or, you know, close friends. And then when you have to hold them accountable or you have to call them out because they did something that either rubbed you the wrong way or broke a company policy, or you have to fire them, whatever the case may be, most leaders, they delay. They delay that conversation. And the reason is because it's easier. And most people have a worldview about conflict, and it just revolves around fear. And it's either because of baggage from your past or because you're just scared, flat out. And we tend to catastrophize things, make it worse than it actually is. And a lot of times, these are just conversations to be had. And it takes a strong core leader to be able to sit down with someone and just hit them with the truth. You may want to, you know, not go in and make it so hard that you're going to hurt someone's feelings. But a lot of times when you tell people the truth about something that is your truth, it's going to hurt their feelings. And I think it's important to be clear with people about what you expect from them so that when you tell them the truth, there's no surprises. But dealing with conflict should be a mindset as a leader, that you need to have these conversations early and often because sweeping them under the rug does nobody any good. And what happens is, if you have conflict with people and you don't address it, then you're going to be in meetings with people, and when that person says something, there is going to be this undertone, this bit of sabotage, of you just want to kind of get them, you're upset with them for whatever the case may be, and it's important that you get that out there. One of the amazing things my team used to do is we used to what we call clear. And before we started our meeting, we'd have to look at everybody in the room, and we were very close, and we'd say, I'm clear with you, I'm clear with you, I'm clear with you. And if you weren't, you stepped outside and we talked about it because we didn't want to address issues in our company when there was this undertone of conflict, and we didn't want to open it up and put everybody's baggage on the table. So everybody took care of it privately. But what happened was people trained themselves over time to. To address this stuff early and often on their own so that they didn't have to do it in our meetings. It takes time to build that kind of trust with your team, to be able to hit them with the truth. But if you're a leader, then you need to lead with this philosophy so that you can set the tone in your office with your team, that you're gonna tell people the truth even when it hurts. And a lot of times, most people, as hard as it is to hear, will come back and circle back maybe a month from now, maybe six, six months from now, and they'll thank you for it. And I think it's important for every leader to be open to the fact that you could be wrong and that it's your truth, and that just because it's your truth or you think it's a fact doesn't make it so. Sometimes it does, sometimes it doesn't. And that's the paradox of being a leader, is that, you know, there's no black or white. It's just a tough situation. No matter who you're talking to, no matter what the context is, every situation has to be dealt individually, and at the end of the day, it just has to be dealt with. And the leaders who pen that stuff off for a day down the road, it's an inevitable way of kind of just asking yourself for more pain and suffering. So if you like to experience pain and suffering, don't address conflict. And if you want to build trust and build a culture of high performers who can hit people with the truth and have some thick skin so they can hear it and listen to it and respond to it, then set the tone up front and. And don't shy away from our conversations.
