In this episode of the Proteus Leader Show, host Erika Andersen interviews Mahesh Guruswamy, CTO of Kickstarter and author of How to Deliver Bad News and Get Away with It. Mahesh shares practical guidance for leaders on recognizing when bad news must be communicated—highlighting repeated performance misses and multiple project delays as key signals. He explains the hidden costs of avoiding tough conversations, such as mounting pressure, loss of team trust, and credibility damage. To counter this, Mahesh recommends building a personal framework: creating a "README" that outlines his work style, setting clear mental models for when to intervene, and communicating expectations transparently. He stresses the importance of personal resilience—mindfulness, physical fitness, and developing a thick skin—to both give and receive difficult feedback. By modeling vulnerability and openly sharing his own quirks, Mahesh shows how leaders can foster a culture where team members feel safe to surface problems early. The conversation concludes with three actionable steps for managers: (1) develop a detection framework for warning signs, (2) cultivate personal resilience, and (3) practice delivering and receiving tough news regularly. Listeners are directed to Mahesh’s book and the Proteus International website for further resources.
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Hi everyone, and welcome back to the Proteus Leader Show. My guest today is Mahesh Guruswamy, the Chief Technology Officer at Kickstarter. Before joining Kickstarter, Mahesh led development teams at Mosaic, Kajabi, and Smartsheet. Mahesh says he caught the writing bug from Stephen King, his favorite author. And today we're going to be talking about Mahesh's newly published first book, How to Deliver Bad News and Get Away with It. So welcome to the show, Mahesh.
Oh, happy to be here.
I'm so glad to have you. And by the way, I really love that title. It's funny, but it's so true. I found over the years that delivering bad news is probably the hardest part of managing and leading for most people.
It sure is.
Yeah. So I think this conversation will be really useful to our listeners. So let's dig in. So what are the key signs that you need to deliver bad news? That is, that a problem needs to be addressed.
I think it depends on the situation, but I'll talk about 2 specific situations that are very common. One is performance issues. So my rule of thumb is if somebody is behind on their tasks like 3 times in a row, even after you give them feedback that, hey, this is not working out, you have to like become better at what you're doing. That's a sign that you have to increase the temperature there and have a conversation with them about, hey, you know, things are not going well. This is what you need to do to improve, et cetera. The second most common issue, at least in tech, is delayed projects.
Right.
So my rule of thumb is your project gets delayed once, it's usually okay because software development is, even though technically it should be a science, but it's not.
Yeah.
But if it's delayed twice, then you do have to reset expectations with stakeholders or customers or maybe your boss. And that is also where you have to like deliver some tough news to your stakeholders. So those are the 2 most common ones that I have seen in my career. And in general, what I tell my team is the little voice in your head, when it starts to tell you that something is going wrong, pay attention to it, please. And a lot of leaders tend to ignore that voice because it's easy to ignore it, hoping that the issue will go away.
Yes.
It won't.
What you just said is so great. Rules of thumb are great. This has happened 3 times. That's great. And that— completely agree with you about the voice in your head, because one of the things I found is that Often, and I'd love to get your perspective on this, leaders get held hostage to people who have good excuses and who seem well-intentioned, and that voice in your head is going, eh, right?
Yeah. What I firmly believe in is 99% of the professional working population are just great. They are skilled. They know what to do. A lot of times when I part ways with people, It's because it's not a good fit for the team or not a good fit for the company, or sometimes not a good fit for me working with this person. It could be like any of these combinations. Inherently, I like to believe that they are good, which is why these discussions are even harder.
Yes.
Because they could be nice. Personally, they're great. They're easy to get along with. You can go have like lunch or dinner with them and you'll have a good time, but they've left behind on their tasks. It even makes it even harder to tell them, hey person, this is not working out.
Yeah.
But the thing I remind my team and the readers of my book is ignoring that is going to be a huge disservice to your rest of your team who is pulling hard to get stuff done. So you do have to, like, pay attention.
Oh, I love that. I feel like mindset is so important. So that mindset that it's a disservice to the rest of the team, and also it's a disservice to that person.
That's right.
If they don't have a clear sense of, OK, this is non-negotiable, then they're just going to keep wandering around. I often feel like leaders do that disservice to their people by not making it clear for them what's really important.
That's right. And I've started using this technique just for myself when I join a new company. During peacetimes, I will often tell my boss, hey, at any point in time, if you feel like I'm not working out here, just tell me. Because I understand that businesses come and go. I understand teams come and go. So don't hesitate to tell me if I'm not needed here.
Yes.
And we'll figure out a way to like part ways amicably. When I was early in my career, I imagined working at the same company for like 30, 40 years. Oh, I'm just gonna retire here. But the more time I spend in the industry, the more I come to realize that tying your self-worth to a company is a very bad idea.
Yeah.
So, I always separate the two of them so that I wanna believe that I'm in control of my own destiny. So, even if I get let go tomorrow, I'll be able to find my way because I have faith in what I can do and my skills.
Wow, that's great. And that approach as an employee, I think, is also helpful for the leader because it gives them a clear signal that you're open to hearing the truth.
That's right. That's right. Yeah.
Pussyfoot around and walk on eggs when they have to tell you something tough.
100%. 100%.
Let's talk about the bad news. So what happens in your experience? What are the downsides? What are the bad things that happen when managers either avoid giving bad news or do it poorly?
We touched upon this briefly. When managers hesitate to talk the truth and sort of give the bad news as is, it's almost like pressure is building up somewhere else that they are not paying attention to. And at one point it's going to explode. So, I'll give you an example.
Yeah.
When I was early in my career, one of the first teams I managed, I wanted to be everybody's friend. I still like to be friendly with everybody. I still like to be personable. But I understand that teams are not families. They're completely different.
Yeah.
So one of the employees on my team, he was having trouble. He was like delayed on his tasks and I delayed it, delayed it, delayed it, hoping for 2 things. One, it'll go away on its own, or 2, eventually they'll get better, but they didn't. And I delayed it for so long. When I actually broke the news to them, he was not happy. He was like, hey, why didn't you like tell me this before? I would have like fixed it because I went from 0 to 100. So I didn't tell him anything. And when I talked to him, I said, we might have to like put you on a performance improvement plan. And he was completely caught off guard.
Oh yeah.
And same goes for project delays too. I mean, the managers always want to deliver good news, especially if you're the owner of a critical project. You want to look good in front of the executives and your boss and your CEO. So you keep saying everything is good, but then The next meeting, if it's the project is red, then everybody's first question will be, why didn't you like tell us last week when we talked about this? So oftentimes it's hard to say those words, but it's better to say it than not.
That's a great example. And people are smart. They know that things don't go great, great, great, great, terrible.
That's right. That's right.
In between, they could have been sad.
That's right. That's right.
So we always promise practical takeaways.
So what can managers start doing today, right now, to be One is start creating a framework for detecting when to start raising the temperature. And I have a lot of techniques in the book which covers performance management issues, project delays, critical conversations with your boss, receiving tough conversation— receiving tough feedback. So, form like a mental model. When do you want to intervene, and when do you want to take a different step? And then tell your team, this is what you're going to do when these things happen. So I started doing this in the last few jobs. I write like a README doc is how to work with me. And I encourage everyone to do it because it kind of highlights what I pay attention to, what I don't pay attention to, what are my quirks, what are things that I'm good at, what are things I'm not good at and how I'll react when I see these things happen.
Mm-hmm.
So, start forming a point of view on when do you want to intervene. So, that's number one. 2, develop a thick skin because you can dish it only if you can take it. This is not in the book, but I highly recommend techniques like meditation, mindfulness. Always remember that work will be work, your family's more important. So, figure out like how to pay attention to them. And then staying like physically fit as much as possible because all those things will strengthen your mind and body. And it'll help you like navigate these tough conversations. And number 3, practice. Like, don't ignore the little voice in your head when it goes, ah, you know what? You should like confront this situation right now before it gets worse. But the most important thing I would say is number 1, start forming a framework for how you're gonna react and when you're gonna react to these situations.
I love all those suggestions, and especially that first one, 'cause I feel like, because it's a difficult thing, I mean, that's what we've always done in coaching is, help people have the skills and a path. And I also love what you said about making it transparent. I think that really lowers the kind of risk factor for everybody. It's like, okay, this is how I'm gonna do this.
Yeah, yeah, exactly.
It starts happening, you know what's going on, you know?
Exactly, exactly. And I think if you're comfortable sharing your own foibles and quirks with your team, the more comfortable they'll be in being open with you when things go wrong, right? Because I tell my team I'm slightly disorganized, which I am. So they'll know if I ask them something twice, they're like, oh, he's just like forgotten that we talked about this, as opposed to why is he asking about it twice.
Precisely. And something that's implied in that, I think— tell me if I'm inferring the wrong thing— is that when you as the leader make yourself open to and vulnerable to feedback, it makes it much easier. It feels much fairer for then you to give feedback to?
Oh, 100%. I believe that teams will reflect back your emotions and the way you show up.
Yeah.
So when you are open with, you know what, I messed up, this is my fault, and you say those words, then your team will be much open to saying, oh, you know what, this was my fault, we messed up, let's go fix this.
Oh, I love this. It would be hard for me to agree more with what you're saying. So thank you so much, Mahesh. I think what you've shared is just enormously useful in Heart of difficulty for managers. So thank you so much. This is great.
Yeah, absolutely.
And listeners, you can find out more about Mahesh and buy How to Deliver Bad News and Get Away with It at maheshguruswamy.com or at Amazon. And to find out how Proteus supports leaders to do the hard work of people management with clarity and heart, just go to proteus-international.com. So thank you for listening, and until next time, here's to creating the life you truly want.
We hope you're feeling better equipped to create the career, the business, and the life you want. To find out more about how we support our clients in leadership, learning, and change, visit us at proteus-international.com. Have an excellent day, and thanks for listening.
