The Introvert Leader

How to Deliver Bad News (and Get More Respect)

• Austin Hopkins

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0:00 | 11:32

Delivering bad news sucks. It's uncomfortable, you feel like crap doing it, and yet you can never avoid it. In this episode, I share how to deliver bad news and still have people like you and even respect you more.



Timestamps

1:30 – Personal Update: Headed to Lisbon, be back with a new episode on May 13th.

2:20 – Why It's So Hard To Deliver Bad News: We make it about us instead of them. 

5:10 – Bad News Mistakes: Delivering bad news gets messy when you make these common mistakes. 

7:08 – Bad News Framework: 3 steps to deliver bad news so people respect you afterward.

9:57 – Challenge for Listeners: Quit trying to feel ready before you deliver bad news. Just rip off the band-aid. 

10:39 – Announcement: Something big is coming in a few weeks, don't miss it




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Engage

The Promotion Aaron Did Not Get

SPEAKER_00

I'd rather step on a thousand Legos than give someone bad news. It makes me feel so uncomfortable, and all I want to do is hide until it's over. Aaron wanted to work for me. I was hiring a manager for a new department I was starting. This was going to be the dream job for someone like Aaron. He had been with the company for a decade, he was stuck doing the same thing year after year, he was ready for the next step. And he had spent the last six months getting close to me. He volunteered to work on projects with me, and we became friendly. Now, once the job was posted, he applied instantly and let me know he was super excited. Aaron went through the first two rounds of interviews along with all the other candidates and eventually it was time for me to make my decision. I really liked Aaron and I thought he was sharp. He sounded and dressed for the part, but he wasn't the guy for the role. I was looking for someone really specific. They needed authenticity and a willingness to learn. These are two things I knew Aaron was going to struggle with. Now, because I was close with Aaron, I knew I owed him the respect of telling him the bad news in person. So I sent him a message and invited him to swing by my office. Later that day, he knocks on the door and I open it. I'm filled with nerves and anxiety at this point. Sits down at the desk and I tell him, hey man, I got some bad news to share. Now, how the rest of the convo went will surprise you. Today I'm going to show you how I deliver bad news so that people still like me and even respect me more. Next week I'm headed to Lisbon with my family to celebrate my parents' 50th wedding anniversary. My parents have been married for half a freaking century. Kind of crazy to think about it that way. I feel like staying together for that long is pretty rare, and liking each other for that long is even rare. So if you want me to ask them some questions about the key to successful relationships, leave it in the comments. I'd be happy to ask. And I will be back May 13th with an all-new episode and a very subtle Portuguese accent. If you haven't subscribed to the show, what's up? I drop new career and leadership content every other week. So click the follow button for me. With that, settle in. It's time to learn something. I hate delivering bad news. It may be the worst thing I had to do as a leader. I tried anything I could to avoid it or get somebody else to do it, or maybe even hope that they could read my mind. It didn't work. So instead, I came up with a simple framework. I use any time I'm going to share bad news with someone. Now, before I share it, I want to chat about why it's so hard to deliver bad news. It's hard to give bad news because we make it about us. You aren't alone, we all do it. Here are the three reasons why I think it's so hard to give bad news to someone. We assume the worst. It feels safer if we prepare for the worst outcome. If I think through the worst case scenario, then I'm going to be more prepared for when they blow up on me. If I assume I might get fired when I tell my boss I missed my quota this quarter, then it won't hurt as badly when he lets me go. This is an illusion. Instead of feeling more prepared for the situation, we psych ourselves up, making it feel way more emotionally charged than it would be otherwise. The truth is, we don't know how the person is going to take the bad news. We can prepare, sure, but we can't spend time focusing on every worst-case scenario. What if I told myself this was going to go fine and they'd still like me after? We're so worried about how we're going to feel. Delivering bad news is going to feel so effing bad. It's going to make me feel like a bad person. I'm literally letting someone down in real time. They're going to hate me. I felt this more times than I can count. Telling employees they were getting a smaller raise than they expected, or telling a coworker we didn't get funding for our project doesn't feel good. But we're so worried about how we're going to feel that we forget what the most important thing is. It's not about us. It's about them. It's about how they feel, how they are going to take the news. We're overly focused on what they're going to think about us or our reputation. It's funny, but the first thing I think about when I'm delivering bad news is myself. Why is that? I'm worried about looking perfect. Why is delivering bad news about something we messed up on so scary? The best leaders, smartest employees, and the greatest visionaries all mess up. It's just part of being human, and yet we still respect them. If your reputation is built on perfection, then it's only a matter of time before it all falls down. Well-rounded reputations are made up of the good, the bad, and the ugly. Nobody trusts someone who's perfect all the time. And once you take off the mask of perfection, life becomes so much less exhausting. I want to give you a quick example to show you what I mean. So I wanted to hire one of my all-time favorite employees to lead one of my teams. She was incredibly qualified, everybody loved her, and she had one of the best styles of anyone I had ever met. There was only one problem. She lived clear across the other side of the country and could move to where the team was located. Now I knew she could lead the team from anywhere because she was that good. I remember going back and forth with our executive team to get approval for her to manage the team remotely. I spent hours creating business justifications and making the case for why she was the right person for the role. She nailed all the interviews, and I was actually at the stage where I was ready to make her an offer for the role. At the 11th hour, I heard back from HR that she was not approved for remote work. I was so gutted. I had to tell her, but how? How could I tell Emily that she wasn't getting the role, even though she had done everything I had asked of her? She was probably going to be so mad at me. She probably was never going to respect me again. I spent days stressing about how I was going to share the bad news with Emily. I was popping Peptobism like they were candy. And I completely forgot about what she was going to go through. Now, apart from making all about me, I've made some other big mistakes when I'm giving bad news. Here are my top three biggest mistakes. Let me help you avoid them. Delivering bad news goes from uncomfortable to straight up bad when we make stupid mistakes. Here are the biggest ones I've struggled with. So the first one, putting it off. My brain loves to avoid the hard stuff. I love making any excuse to not deliver bad news. I have a sore throat, I better wait till I feel better next week. They just came back from vacation, so they probably need a few days before they're ready to talk about important stuff. My boss was kind of annoyed with me this week, so I'm gonna wait a couple of weeks to tell them what actually happened. I'm a master at making excuses to avoid hard conversations, but every time I put off the bad news, I'm thinking about myself and I'm keeping myself in a space of anxiety and worry. The times when I just rip off the band-aid are the times where I felt the best. Getting the hard stuff out of the way always feels better than saving it for later. Second one that I've struggled with was making a mountain out of a molehill. People are resilient. They can take bad news better than you think. So when you put it off, when we obsess and overthink about the conversation, we make it something way bigger than it needs to be. Yeah, it might suck to tell your boss you forgot to follow up with the client, but if you're to look back a year from now, is it gonna be the end of the world or just a minor speed bump you had to get over? I found it's usually never as bad as we think. And as Seneca famously said, we suffer more in imagination than in reality. The last mistake you gotta avoid is not showing a path forward. Bad news has a funny way of feeling final, and that's the worst part. If your boss tells you you're not getting approved for your new project and doesn't say anything else, it kind of feels final, right? It feels like there's nowhere to go from there. You feel helpless, you feel hopeless. But if instead he says, hey, you're not approved in 2026, but I'm gonna push for approval in 2027, this thing isn't as bad, right? People can handle the darkness as long as there's light at the end of the tunnel. If you have to deliver bad news, follow it up quickly with some positivity, some learnings for the next time, or a path to success. People just want to know how to get to the other side of the bad vibes. Tackling tough conversations head-on, keeping a healthy perspective and staying collaborative are key, but they don't make delivering bad news easy. A repeatable framework makes tough conversations suck a whole lot less. So I've had to share bad news hundreds of times in my career. As a leader, I felt like it was almost half my job, which sucks. You know, whether it was telling Tori she had to redo the proposal that she sent me because it wasn't detailed enough, or letting John know that a client shared some negative feedback about his experience with him, or maybe telling Kelsey I'm gonna have to let her go. But what I did was develop a framework that worked for me. So I'm gonna cover each part and then I'm gonna tell you how it ended with Aaron from the beginning. So part one, tell him what happened. Don't beat around the bush, get right to it in the beginning. The more direct and honest you are from the start, the better this will go. Chris Voss, the famous FBI negotiator, always says that people are much better at handling bad news when they're braced for it beforehand. This helps them brace and prime for the bad news, and they can handle it. Part two, why it happened. Give concrete info about the situation. Don't make excuses, be as clear and concise as you can, even if it's uncomfortable. And remember, it's not about you in this moment, it's about them. And part three is the wrap-up. This is where you share the learnings, what they can do next, or the next steps. So after you share the bad news, it's time to soften the blow and offer a path forward. Don't just drop the bad news and bounce. You don't want them to feel like shit. You want them to see a path to success. Okay, so here's how it ended with Aaron. He sat down at my office and I said something like this: Hey man, I know you've been wanting to hear my decision for the role, but I got some bad news. Unfortunately, I hired someone else for the job. I know you really wanted the role, but I want to share with you why I chose Chelsea over you. The reality is this team is really new and they needed something really specific. I was looking for someone who could come in and be a sponge. I needed someone that could come in and instantly get the respect of this A-team. And honestly, I thought this was going to be a struggle for you. During our interactions, while I was impressed with how you interviewed, I never could get a sense of the real you. It always felt like you were holding back or showing me a version of yourself that you thought I wanted to see instead of the real you. Now I know this isn't easy to hear, man, but I want to pause and see if you had any questions for me. So I gave him a chance to ask me some questions. He didn't really have any. And then I wrapped up by basically saying, I thought you were super talented. And while you didn't get this role, I don't want this to be the end of our interactions. I want to help you prepare for the next one. So I offered to meet with him one-on-one or give him feedback on projects. And, you know, I could tell he was visibly hurt, right? But at the end, he stood up, he shook my hand, and he thanked me for the opportunity and honesty. Now, the good news is Aaron and I stayed in contact and we even worked on a few other projects a few months later. And it wasn't awkward because I was honest with Aaron and I showed him that I cared. And I'll never forget, a year later, Aaron called me up out of the blue to tell me he had just accepted a big promotion at another company. I was so excited for him and this new season. He wrapped up the call by asking if we could stay in touch. So bad news was delivered and the relationship was maintained. And I gotta tell you, this framework works whether you're delivering bad news to an employee, a cowork, or even your boss. The direction doesn't matter, the framework does. So I want to wrap up by giving you a challenge. My challenge for you this week is simple. Stop trying to feel ready or perfectly prepared to share bad news. It's supposed to feel bad for you. There's never going to be a perfect time or a perfect way to say it. Just rip off the band-aid and schedule the chat. Okay, quick plug. You probably don't need full-time coaching right now. You're most likely doing pretty good at work, and the sky isn't falling, but I would bet that you're facing something kind of uncomfortable in the next couple of months or weeks. If so, I know I can help you figure it out with a one-time session. This is quickly becoming our most popular service. No monthly commitment, just a one-time video call to help you figure out the most pressing situation you're facing. So if you need some one-time help this month, click the link in the description. Okay, I want to give you a quick heads up about something I've been working on behind the scenes. Over the last several months, I've been developing something I'm really proud of and I know is gonna add a ton of value to your leadership journey. I'm not ready to share all the details yet, but I will be in the next couple of weeks. So if you aren't already following the show, make sure you do, or you're gonna miss it. I think you're really gonna love it, to be honest. So, delivering bad news never gets easy, but it does get a little less scary when you have a framework. As you go into these convos, I want you to remember it's about them, it's not about you. It's okay to feel uncomfortable, but it's not okay to make them feel like crap. You can't avoid giving bad news in your life, just embrace it for what it is. And I want to say thank you so much for listening. Make it a great day. Subscribe for new episodes every other Wednesday.

Contributor

Austin Hopkins

Host