Staying Out of the Comfort Zone: Raising Your Hand for Messy Problems

Starting the conversation:

Not every industry trend is worth following. Where you spend your time is the one thing you truly can control. Mahesh Guruswamy, Technical Advisor at Luster, shares how getting out of your comfort zone by raising your hand for messy business problems builds beyond confidence to generate authority.

Use your experience to step up and take on new riskier situations. Your time is your currency and being open to failure shows yourself (and your superiors) that you are willing to risk and try new things. With the speed of technology charging forward, you benefit from stepping into situations that showcase your cross-functional curiosity and build your structural skills right alongside honing business instinct.

In this program, you will hear the importance of having two-way door communication for big decisions; that just because your competition is doing it doesn’t mean your company should; and the fact that time is your only real currency so spend it wisely. Jess Dewell talks with Mahesh Guruswamy, Technical Advisor at Luster, about being BOLD and taking the risk to raise your hand and accept messy business problems.

Host: Jess Dewell

Guest: Mahesh Guruswamy

What You Will Hear:

03:00 Writing is a tool for both work and personal processing.

• Writing serves dual purposes: professional and personal journaling.
• Handwritten notes or typing — whatever is closest works.
• The act of writing helps Mahesh exercise thoughts from his mind.

05:15 Commitment and consistency unlock creativity and growth.

• Practice writing consistently, even if not every piece is used.
• The process of repetition makes getting started easier.
• AI tools may inspire topics, but developing your own voice is crucial.

07:50 Stepping into challenging situations rewires comfort and capability.

• Push yourself to practice public speaking, even as an introvert.
• Recognize the process: initial discomfort is normal but fades as you get going.
• After the event, downtime is essential for recharging.

10:50 Time is your true currency — spend it with intention.

• Everything is exchanged for your time, so be dogmatic about where you spend it.
• Prioritize time for downtime, family, and activities that matter to you.
• Others may not understand, but knowing yourself is key to making the right choices.

16:15 Framework your decisions — one-way doors or two-way doors.

• One-way door decisions are hard to reverse — these require more thought and involvement.
• Two-way door decisions are easier to unwind; let your team experiment and learn.
• Empower teams; speak last in the room; don’t send signals that invite automatic agreement.

23:10 Creating a culture of ownership and feedback.

• Leaders must openly own mistakes and apologize.
• Doing so signals openness to feedback and builds psychological safety.
• Disagree and commit — leaders can back a decision they don’t fully agree with, but commit to see it through.

28:30 Don’t follow the herd — make decisions right for your situation.

• Avoid herd mentality, especially in leadership circles.
• If your company is financially stable, deploy people on projects versus layoffs.
• Founder CEOs and entrepreneurs are less likely to follow trends blindly compared to career CEOs.

36:20 Understand and own what truly is in your control.

• The main thing truly in your control is where you spend your time.
• Show up with the goal of helping teams and individuals move forward.
• Authority and influence are limited, but accountability for outcomes is essential in leadership.

41:30 It is BOLD to claim your business instinct and own what you can control.

• Don’t stay in your lane — understand all domains of your business deeply.
• Authority is earned by solving messy problems and being willing to step up.
• Bring thoughtful, cross-functional insight and help your company move forward by owning your instinct and decisions.

Resources

• Mahesh GuruSwamy on LinkedIn
• How to Deliver Bad News and Get Away With It
• What is actually going on in the minds of executives?
• When to intervene

Transcript

Mahesh Guruswamy 0:00
What I realized as a leader is you’ll get authority in a specific domain or a direction if you solve messy problems for that direction. The more thoughtful you are about your approach, the better it’ll resonate with your peer group and even the company.

Announcer 0:21
Every leader needs a trusted partner for the moments that matter. This bold business podcast conversation is that partnership. Your go-to resource designed to break the inertia and refresh your perspective so you can start making moves.

Here is your host, an insightful truth teller who serves as the catalyst for getting the right work done and who asks the questions that truly matter, Jess Duhl.

Jess Dewell 0:48
Mahesh Guruswamy is the chief product and technology officer at Kickstarter. He is joining me today for our bold business podcast program. And let me tell you, not only is it cool to have a conversation about business from a technology executive, it is cool to have a conversation with somebody who thinks deeply and seeks out and tries new things.

And that’s what you’re going to hear in this program, specifically in three areas. The concept of in big decisions, are they one-way doors or two-way doors? And what does that actually mean?

You’re also going to hear about just because others are doing it doesn’t mean to do it. And checking in with that business instinct to find out what’s right for you and your company in the marketplace. And the third thing is that time is the real currency, and that is what we can control.

So use it wisely. So in those three areas, we run deep into several different topics that I know you are going to enjoy. And so as you’re listening, if you think somebody that you know is working on a concept like this, or you were having a conversation about something similar recently, send this program over to them on YouTube or wherever you are listening or watching from so that they can hear it too.

And don’t forget, this is what it means to be bold in business, having the conversations and keeping them going. So add your voice, add your comments and thoughts to the discussion around in the platform that you’re listening and watching on. Remind me, when you’re not at work, what do you do?

Mahesh Guruswamy 2:26
If I’m not at work, either I’m reading, writing, working out or family time.

Jess Dewell 2:35
Is that how you prioritize them? Is that how they get prioritized?

Mahesh Guruswamy 2:38
No, I would put family time first, working out next, reading and then writing.

Jess Dewell 2:44
And who’s in your family?

Mahesh Guruswamy 2:46
Me, my wife and my 11-year-old son.

Jess Dewell 2:50
We’re entering high school this year. That was my recent past. I got you there.

Is writing for you, is writing for work?

Mahesh Guruswamy 2:58
No, writing both for work and also for personal reasons. Yeah, like I tend to process stuff by writing them down. So the minute I write something down, I’ve exercised it from my head, which is the way I think about it.

Jess Dewell 3:11
That’s a skill I can learn how to use. I’m a talk to think. Yeah. And I know it can drive my partner in life, my husband of 25 years, Brian, mostly, but in general, I know that there is some unlocked potential in my work world and just for my own self and my personal development to anchor in differently if I were to write. And so I’m not sure, but I have a block from my brain to my fingers. Do you type?

Mahesh Guruswamy 3:39
I do both. Sometimes I write, let’s see, I have like an actual pen and a book here, or I use my laptop, whatever is closest.

Jess Dewell 3:48
And you don’t care that they’re not synced or anything?

Mahesh Guruswamy 3:50
No, not really. Sometimes it’s just like doodles. Sometimes it’s just like a couple of lines.

Sometimes it’s just what’s top of mind for me. Other times it is like structure. Okay, I have to get something out for myself, stack or LinkedIn or something.

So those are definitely, they go on a laptop.

Jess Dewell 4:08
Yeah. A lot of my writing has to start in some sort of a note form. Like I draw pictures and I put all these things on and then I can see them.

And I’ve not overcome this yet. I have to see a bunch of things in order and rearrange them. And then I could write about them, I think.

But I have to get them out. I don’t visualize much in my head, or if I need to try and communicate it, like what does it actually look like out of my head? And then I do the writing about it.

I’m guessing, do you know of a product or a process that you’ve heard of that benefits people like me that start with a, what are all the pieces? And then literally moving sticky notes around?

Mahesh Guruswamy 4:44
When I was in the middle of writing the book, I was like, I have no idea how to start this chapter because my publisher or editor was, there’s a gap here. You need a chapter here that explains the two chapters in between the two on the bookends of it. And I was like, oh, maybe I buy a product that will help me get out of this funk I’m in.

But then I reread Stephen King’s nonfiction book. It’s called On Writing.

Jess Dewell 5:10
Yes. I read that in the 10th grade.

Mahesh Guruswamy 5:12
Yeah. It’s a great book. I recommend it to everybody, anybody who wants to become a writer, for career or otherwise.

He says the only way to get better at writing is write every day. Even if it’s finer words a day, aim for it. I don’t do finer words a day because I don’t have time, but when I was in my writing mode, I would write even if it didn’t make it into the book.

And the more you do it, the more you do it consistently, the more easier it would become for you to get going. These days, you can also put it in Chat GPT or whatever AI tool you have. In the beginning, I thought it was pretty cool.

It’s giving me some starters, but over time, I realized that it doesn’t match my voice exactly. So I might get inspired from the topics that it came up with, but in the end, I just write it myself. Just start writing and then it’ll flow when it has to flow.

Jess Dewell 6:07
Yeah. Yeah. And I hear you on that part.

And that’s actually, I feel like that about podcasting, by the way, about we’re in, by the time this airs, we’re going to be in season nine. So I have a lot of podcasts about, and it’s very different kind of work today than it was at the beginning, because at the beginning there was more to think about, how do you do all of these things? How do you create and show up all the time?

And then what does that system start to look like? And can you commit to it? And it sounds like for writing is the same way.

It’s the commitment to it and the recommitment to it as needed to, Oh, this is second nature.

Mahesh Guruswamy 6:46
That’s right. That’s right. And same goes for public speaking too.

I really got into it a couple of years ago and I’m an introvert by nature. So I typically, or like at least back then I never did like public events or I wouldn’t go to any conferences where I have to talk. And a couple of years ago I took a go, okay, well I’m going to push myself to do these things because if I want to market my book after it gets released, I want to be out in the circuit.

And I have no illusions on how I feel before and after that event. It was more, okay, I know it’s going to be hard for me. I’ve like made peace with that.

I also know that once I get going, it is easy. Once the first words come out of your mouth, then it’s fine. You just are in the flow.

You just keep going because you know your subject well, you’re prepared for it. And then I also know at the end of it, I’ll be like drained. So I don’t have any time or energy for socializing, or they’ll have these, you know, three-hour talks.

And then like a happy hour after I just duck out after the talk was no energy left in the tank to have a drink with anybody. And then I just go home with you. If you push yourself and you like practice it and you were like, to your point, committed to it, anybody can become a public speaker.

Anybody can become what they want to do. It’s just a commitment. Obviously, like if there’s a need for me to network, if there are customers in the event, then I go spend time with them, but I don’t, these networking events or these conferences also like long, right?

So they’ll start at six, the talk ends at eight. And then they have like happy hour and dinner that goes to 11, 12, whatever. So I’ll spend time, maybe like an hour and a half, like mixing after the talk.

Or like I just duck out if I, if there’s no value in, in like networking with the people there, because I don’t like directly benefit from them or I can’t directly help them. Then I just like duck out.

Jess Dewell 8:32
Yeah.

Mahesh Guruswamy 8:32
So I don’t really, I’ve gotten feedback from, from people who organize the event that, Hey, you should stick around more because it’s just, but I know it’s, but they, but I know me better than anybody else. Right. So I know that I won’t be tuned in after this point in time.

I’m like, I’m just going to duck out because otherwise I don’t want to come off as rude to somebody who was trying to talk to me. And I’m like zoned out thinking about whatever.

Jess Dewell 8:56
Yeah.

Mahesh Guruswamy 8:56
And the answer to your second question is I just want some downtime where I don’t have to think because it is, it is exhausting for me to put myself out there. It’s like hard for me to show up in public and give my whole self to that event. And I, what I mean by downtime is, and not thinking is I would watch like something that, that I watched before that I really enjoy, which is, we do not have to think right.

So for example, one of my go-tos is this old British sitcom called Yes Minister. I don’t know. So Yes Minister, it’s about this bumbling minister who gets elected and he comes in with all the things that he wants to do in terms of changing the British bureaucracy.

And he runs into the British bureaucracy and is unable to do things. And there’s three seasons and there’s a sequel to that called Yes Prime Minister. So the same minister gets, you know, gets elected as prime minister, but he still is unable to do most of the things he wants to do.

And I’ve seen that episode at these, those two shows so many times that I don’t have to think what comes next, but it’s just, it’s like white noise for me, right? So I just sit in front of the TV for 20 minutes or whatever, and then just have that as white noise, just calming me down. So that’s what I do.

Jess Dewell 10:11
You have mentioned you’re an introvert. I’m an extrovert and I also need downtime. Somewhere along the line, I claimed a thing that because I’m an extrovert, I should be able to be on as long as people wanted to be on.

And that is something that I’m still having a hard time letting go of, yet I recognize it is a hold back. When you said I only do, I only do work and interact and engage where I can help. That was my paraphrase of what you were saying.

I think that that is incredibly powerful because if I can’t be of help or if somebody can’t help me, it really isn’t the highest and best use of my time.

Mahesh Guruswamy 10:51
That’s right. As I get older, the thing that I was becoming like really apparent to me is time is the only currency you have. You’re exchanging time for everything else in life.

So I have become more and more methodical and even dogmatic about where I want to spend my time. And when I’ve been, people tell me, including old bosses have told me that, hey, you should have stuck around for the event or you should have stuck around for this networking thing or this mixer or whatever. And I’m not going to tell them it’s not useful, but I do value where I spend my time.

And the 20 minutes at the end of the day in front of the TV watching Yes Minister is important to me. So I try to make time for that. And same thing applies for family time too.

When we sit down to watch something together, I don’t dig into that. I don’t eat into that. This is our time.

Dinner and the show before and after, it’s our time. So we have to spend it together.

Jess Dewell 11:50
Okay. Now I got to ask, what are you watching as a family right now?

Mahesh Guruswamy 11:54
Oh, so we’re watching the new Star Trek, Star Trek Strange New Worlds. That’s on Paramount. It was harder before because my son was younger.

So you can’t see every show that you want to see with him. So now it’s becoming easier and easier to watch even like slightly mature shows with him because he understands it. So we’re watching that.

And then when my son is not with us, he’s off playing with his friends or whatever, my wife and I, we’re watching Babylon 5, which is a sci-fi from the nineties.

Jess Dewell 12:25
It’s awesome. By the way, it’s been a long time since I’ve seen Babylon 5, but that’s cool. I will actually, I’m going to take Star Trek The New World’s Home because we’ve tried to watch a few things right now.

To your point about age-appropriate and what actually is, we just started watching Cobra Kai.

Mahesh Guruswamy 12:43
Oh, that’s a great show.

Jess Dewell 12:44
It’s a little harder to get to see it with us when we still watched it the first time, when it was out, we were like, Nope, they’re high school kids. You’ve got to wait till high school.

Mahesh Guruswamy 12:51
Maybe this is a, it’s like a controversial parenting choice, but I actually don’t have a problem with my son running into explicit stuff. Unless of course it’s like completely like out there, that’s different. But if it’s like an intense fight scene or if it’s in a really messy situation emotionally or whatever, I don’t have an issue with it because I know that he’s into it in the wild or seek out based on peer pressure.

I think the tactic that my parents used is, okay, you can’t do this. And every 14-year-old, 13-year-olds, the minute you tell them you can’t do this, their mind goes, I can’t do this. So I’m like, okay, this is what it, this is what reality is.

And this is what movies and entertainment is like, this is how real relationships work, right? This is how real conflict resolution works. This is when your favorite singer sings about this stuff.

This is not real. They made it up. And this is not how the real world works.

And when, and a lot of it is theater. So, you know, I try to focus on that more than trying to, okay, you can’t see this. Obviously, if it’s like a mature show or whatever, then, you know, I’m not going to watch Game of Thrones with him, but I can watch Cobra Kai with him because, okay, I can explain all this in a way that he can understand.

Announcer 14:16
Feeling stuck? Like, what got you here won’t get you there. The pressure to grow is on, yet the path isn’t clear yet.

You don’t have to walk that path alone. This is the Bold Business Podcast. Like and subscribe wherever you listen.

Your host, Jess Dewell, is the strategic partner you’ve been looking for, asking the questions that truly matter. It’s time to break the inertia and get the perspective you need to make your next move.

Jess Dewell 14:51
If we make things a little more nonchalant, we don’t have to sweat the small stuff as the book says, right? And what is actually the small stuff when we’re thinking about time and how to spend it. And if we’re spending time focused on the things to avoid or protect or contract around, what are we actually using energy and resources that are actually exciting and curious making and creating new opportunities for not only creativity, but problem solving.

Mahesh Guruswamy 15:24
That’s right. That’s right. That’s exactly right.

That’s exactly right. Yeah.

Jess Dewell 15:27
Yeah. And so I have to check myself sometimes. And by the way, I have to do that at work.

I don’t know if you have to do that at work too, but I’m like, if I feel myself digging in some, then what? What’s the reason for the dig in? And is it in my head?

Is it in my heart? Is it a trend? Is it my business instinct somewhere?

What’s going on? I’m guessing you have really good business instincts.

Mahesh Guruswamy 15:49
Well, I think the, so in my role, I tend to make fewer decisions, but high quality decisions. If I’m managing a team of 30, 40, 50, 100, 200, whatever, you can’t tell everybody what to do. So you have to paint a picture and paint a vision for them and they can go execute on that vision.

So the data decision-making, I leave it up to them to decide whether this is right or not. So I categorize business decisions into one-way doors and two-way doors. Have you heard of that concept before?

Jess Dewell 16:23
I’m excited about this. No.

Mahesh Guruswamy 16:24
So one-way door decisions are decisions you can unwind easily or cheaply. So, for example, if you name, change the name of the company, or you decide to build a new development center in like Kirkland or whatever, right? So you can’t unwind those decisions easily because it’s an expensive decision.

So you have to be really thoughtful and sure that this decision is going to work out. Two-way door decisions, and I would argue that most decisions in business, at least in the tech land, is two-way doors. So you can walk in and walk back out.

Like you build this feature, if it works, great. If it doesn’t work, walk back out. So I tend to put decisions into these two buckets.

If it’s a one-way door, I get involved much more than if it’s a two-way door. If it’s a two-way door, then let the team make the decisions. And just like, you can share your opinions and your thoughts on it and then just say, hey, just be careful about these things, X, Y, and Z.

And as long as they’re keeping that in mind, as long as they know what success and failure looks like, it’s fine because they’ll either succeed. My hope is they’ll succeed most of the time. But if they fail, they’re like, okay, this is why we failed.

We’ll unwind this decision and then we’ll move in a different direction. I wasn’t like this when I was, I’m 43 now. When I was like 30-something, I was very much, very opinionated. I would dig in. Yeah. I was like, it’s, yeah.

My wife talks to me about it all this time. We were like way different person when we got married. And over the years, it has changed me, like becoming a father, becoming a leader in large companies, enabling people to make decisions, empowering teams.

That has all changed me. The one book that, that gave me a framework for this is called Leadership is Language. And it’s a great book about, it’s written by the same guy who wrote Turn the Ship Around.

Jess Dewell 18:07
Oh yeah.

Mahesh Guruswamy 18:07
So David Marquette, he wrote the Leadership is Language book. And it’s a great window into how words you say as a leader really matter. For example, speaking first in the room.

That is a great example. I think I knew it even before I read the book, but it heavily influences what everybody else is going to say. So I tend to go last in the room.

Another great example is finishing your suggestion with a, for example, this is how my opinion is. We should solve X this way, right? Which means you’re already sending the signal to your team to agree, to agree point of view.

Jess Dewell 18:49
Before you continue, I’m going to be like, Ooh, I used to do that. And I stopped, but I’m, and I’m really glad I did. All I was doing it, all you listeners and watchers out there, listen, tune in here because I was searching for, are you tracking with me?

Are you tracking with me? But so my goal of, are we, are we in the same space to keep going was actually sending the wrong signal of what if I don’t think it’s right? Now what do I do?

Or, Oh, I’m supposed to think this is right because it’s not my decision to make, which was the exact opposite of what I was doing. So I think intuitively I got there, Mahesh, just now here, I’m talking to think and process a little like, Oh, this is really cool. And not doing that because there was, it was actually a competing priority, what you wanted versus what you were actually getting.

Mahesh Guruswamy 19:35
Exactly. Exactly. And there’s a great case study in the book about how it’s about the, it’s about a journey that this container ship takes, which ended in tragedy, tragedy because they ran into a storm that, and they couldn’t recover or get out of it where there were all the signals were being sent to the captain.

Hey, this is coming. And if you take this route, like these are the potential pitfalls, but the way he, maybe it’s definitely not his fault, but nobody had taught him like, this is how you show up as a leader. The way he showed up with his team, didn’t give his team runway to help him.

His people from his team had the right ideas. They’re like, we run into this storm, it’s going to be bad. And, and because the language that the leader was using was not conducive for that kind of discussion, they ended up running into the storm and never coming out of it.

And the text in the business case was lifted off of the black box, off that container ship. So it is actual excerpts from the black box that shows where the communication broke down, which is why I’m like very thoughtful and careful about dismissing what my team is telling me, especially if they’re, okay, no, this is not going to work. And okay, this is going to end badly, or this is the problem here.

Then I really pay attention. Obviously, there are situations where if it’s a, if it’s a one-way door or two-way door, depending on that, sometimes I might underwrite a risk if the risk is not too much, but if the risk is too much, then you do have to pay attention to what your team is telling you.

Jess Dewell 21:12
Yeah. And so if I were to say that, paying attention to the, so the outlier information, when something, is it different than that?

Mahesh Guruswamy 21:23
It’s an outlier for a few things. Like, yes, outlier information is one of them. When somebody tells you, Hey, and like, it’s a lonely voice that says, okay, this is not going to work out.

You have to dig in and understand why. But the other piece is creating an environment where people feel that it’s okay to challenge the leader.

Jess Dewell 21:40
Yeah.

Mahesh Guruswamy 21:41
That is more important than anything else. Because even to this day, leaders have skewed views of what authority means and what responsibility means and what does it mean to be a leader? And it comes in the way like very much.

So if you create an environment where your team can give you critical feedback and say, Hey, you’re thinking about this the wrong way. And then that’s the kind of environment I want to work in. And I would argue that every leader should have created an environment like that, where they get critical feedback about their decisions and thought process.

Because you don’t have all the answers. I don’t have all the answers.

Jess Dewell 22:16
And we have to, we actually have to, not only, I hear you, and it’s more than creating the environment. It’s actually walking the talk. Yeah.

That makes the environment. So it’s almost, so I know I was thinking, what’s the picture of that look like? What’s the end goal?

And then I was thinking, and I am a feeler through it, and I’m feeling, well, how would that be? Oh, people actually have to challenge the authority in the room. Do they feel comfortable?

Are they made out to be the lonely voice in that instance, even if they’re not the lonely voice among other things? So I appreciate the, I use the word competing priorities. It sounds like it’s a little, I use that a lot, but I’m thinking, Oh, there’s some depth in here.

And this is one small facet of what that is.

Mahesh Guruswamy 23:01
It’s like an easy, this is almost like a cheat code, but it’s so interesting to observe people not utilizing this cheat code. The easiest way to get your team to give you critical feedback is learning to apologize when you mess up. As a leader, if you make the wrong decision and things go south, it’s on you to get on stage or get in front of your team and say, Hey, sorry, I messed up.

This is my fault. And the more you do that and more comfortable you are doing that, it sends a signal to everybody around you that, yeah, this person is open for feedback and we can talk to him or them or her as an, as a normal person and not have to worry about repercussions. Like Amazon popularized disagree and commit, which is, I’m sure you know about this, but very few leaders know how to actually do that.

Jess Dewell 23:50
Yeah, it’s true.

Mahesh Guruswamy 23:52
Right. Because disagreeing, I was giving this talk at a university and I give this exact example is when Jeff’s team, Bezos’ team pitched a prime video to him. He was not aligned.

He was like, this is not going to go well. The margins in video are thin. We’re not going to make any money here.

And there’s no easy paths to e-commerce, which is what he wanted to see. He said, but I disagree with your sort of direction here, but I’m going to commit to a few years of this experiment. So he greenlit the money.

And that’s what like disagreeing and committing means. You’re like disagreeing, but you’re also committing to the path forward just to see things through and see what happens. A lot of leaders want to disagree, but not even disagree, just agree, just agree and move on.

That’s what they, that’s what they want. And I’d say that’s not the recipe for building a strong forward-looking team.

Jess Dewell 24:45
In today’s climate, fast changing, both in technology, both in global matters, all of the things, right? We’re changing so fast. How?

And the need to do more with less. The recognizing that money is a little less abundant for whatever reason, right? Costs of things are going up, whether it’s debt or help or technology or all of the things, right?

So we’re always looking for that mix of the give and the take in there. And it does take money to make a commitment, even if it’s not the right one to try it out. And I’m a big believer in that.

So I’m hearing you talk about this and sharing an overview for people listening and watching who don’t know what disagreeing and commit means just because sometimes we need data. It is the best way to go get real-world data. If we can’t get it in the reports, if we can’t get it in our surveys, if we can’t get it in whatever way we’re getting our data or cues, the only way to do it, to get data is to go spend money on it, to see what happens.

Mahesh Guruswamy 25:48
That’s right. Sometimes you got to, in the words of Nipsey Hussle, right? So if you want a slice, you got to roll the dice.

So sometimes it’s a risk. You just roll the dice and see what happens. As long as you know that everybody knows there’s an experiment, there’s a start date and an end date, and then you can decide whether you want to continue investing in this experiment or not.

It’s totally fine. It’s very interesting that people tend to argue about these things so much. Even if you want to do an experiment, they just argue and complain and dig in and people’s feelings get hurt.

In my mind, I’m going, well, let’s just say if it’s an investment for a quarter, let’s just do it. Let’s just do it and see what happens. If it doesn’t work, it doesn’t work.

No harm, no foul. You just move on and do something else.

Jess Dewell 26:30
Yep. Which does a lot of things. It tests the assumptions.

It tests the resources that are actually there. It provides opportunities to work together or not. So can people get together around a common goal amidst all of the other regular stuff going on to get to something?

I will be the first person to say, I think it’s a weakness that I hold onto things too long before I let them go. However, I also think that it is an incredible strength because while sometimes it turns out to be neutral to negative, most of the time there is always an upside that got us to that next best decision that was nowhere where we thought we were going to go. That if we didn’t take that risk, we wouldn’t have had the opportunity to see.

I’m guessing you’ve seen that too in the experiments you’re talking about with your teams.

Mahesh Guruswamy 27:25
Right. There are certain things that I take strong stances on and I make it clear that I’ll live with the choice. If I make that choice because I have a strong opinion on this, but as I said before, those decisions had to be fewer in number and they have to be high-quality or overarching decisions.

You want to make the org structure different or you want to change people’s compensation or you want to right-size the organization. Those things are big decisions and in those ones, I will take a strong stance. There’s no half measures.

If you want to save the company’s finances, then yes, you do have to do a layoff and this is what it means and you make that decision. Everything else, you just learn from it and then move on.

Jess Dewell 28:08
I appreciate you bringing in that concept of contraction into this. Sometimes the experiment is that.

Mahesh Guruswamy 28:14
That’s right.

Jess Dewell 28:16
Okay, fine. Because I’m going to call this old school thinking, please feel free to disagree with me if you think it’s that, if you think it is a common measure. Oh, we are spending too much money. What are we going to do? We’re going to reduce our people.

Mahesh Guruswamy 28:29
The one additional color I would add to that is I was asked, one of the board members asked me for some interview a while back. I think if the companies, let me back up. I don’t think you should make a change like that just because everybody else is doing.

Jess Dewell 28:46
Thank you.

Mahesh Guruswamy 28:47
Say it again.

Jess Dewell 28:48
Say it again.

Mahesh Guruswamy 28:49
Because the leaders tend to follow the herd. They’re like, oh, there’s other CEO in this other vertical, other company that’s very similar to ours is doing this change. So, hence we have to make the change too.

If your company’s finances are fine and you have faith in the things you’re investing in as a company, then there is no point in doing a layoff just because. Because that’s just like Lemming’s behavior, right? So if your company is in trouble, then yes, make a change and cut some costs or reduce the size of the org.

If you know that you can win in your space and if you know you have a clear path forward, why not deploy those people into that path forward? Why not? So one thing I’ve noticed is career CEOs make that choice very easily.

It’s like everybody else is doing it. So I’m just going to do it too. Founders, CEOs, entrepreneurs, people who have risen up in different ways, they tend to not make that choice.

They’re like, okay, if this is not working financially, we’re fine. We’re going to take this team and deploy them on something else, even though that it might hurt the bottom line in the short term. And those decisions are hard to make outside of founder CEOs because they’re like, yeah, I understand this company and I understand the space.

I’m going to just make this choice here. But I absolutely don’t. Sometimes CEOs also don’t have a choice because the board is like, this is happening in our portfolio, so you have to worry about this too, which is also foolish in my opinion.

But you don’t have to follow the herd. Just make the right choice for your own situation.

Jess Dewell 30:20
And if it’s really the right choice, there’s a case to be made that doesn’t have to feel forced.

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Jess Dewell 30:58
I think you’re right about the founder CEOs willing to do things that have bigger dips in the short term. And it’s because we’re playing with more risk more often in a lot of ways. It’s about what we were talking about at the beginning.

We just do it a lot. We’re a little more comfortable with it. But at the same point, I mentioned business instinct.

And there is something to be said for what that means and being willing to go, oh, if everybody else is doing it, that means there’s got to be another way. Or they’re really not confident in where they’re at. And look, I’m really confident about this and this of what we’re doing.

So why not lean into that? And what does the view look like in that realm of perspective? I think that I really appreciate how you’re bringing that together.

And that is interesting because you’re right about boards and companies that are part of bigger portfolios. Man is all I have to, because that’s, it’s a little harder because it’s a little more of a, would you, I would say it feels like a one-way door.

Mahesh Guruswamy 31:55
I mean, it’s absolutely a one-way door. And those decisions, there has to be sound financial reasons for that. And it’s funny, when you put a smart group of people, Ivy League educated people in a room, they’ll always come up with reasons that sound very smart and real, but the reality might not be there.

I think it’s like the housing crisis, right? On paper, it’s not great until people started defaulting on their loans. And it’s funny, like the housing crisis, companies are packaging up debt as securities, which is insane.

If you think about it right now, today, how do you like packaging loans as securities, which just doesn’t make any sense, which is why there’s like recent kind of layoffs and all that. I feel like, yes, you will look, your sort of bottom line will look good in a quarter, two quarters, but have you made sort of significant progress in your company’s growth or innovation, et cetera, especially for tech companies? I’m just astounded that tech companies choose this route because tech is always ahead of the pack when it comes to innovation.

So if you have a thousand people and financially you’re fine, why not just put those thousand people on something else and make money like that? But I guess it’s the side effect of tech becoming commoditized. Everybody is, okay, tech is like the auto industry now.

So everybody’s doing it and it doesn’t take really experienced workforce or like skilled workforce to do this work anymore with the AI tools, et cetera. So we’re going to behave like any other public company, which was definitely not the case 15 years ago or even like 10 years ago.

Jess Dewell 33:33
Oh, I know. And with the speed that things are moving, I think tech used to mean a little bit of things and now tech means a lot of things and it’s becoming a commodity where cars was a certain set of things and it still is a certain set of things. So it’s an interesting, I can’t wait to see how this goes and what that actually means because tech is like Kleenex these days, right?

Everything’s called Kleenex even if it’s not your brand. The brand name became the thing, right?

Mahesh Guruswamy 34:02
That’s right.

Jess Dewell 34:03
I’m very curious and I love being in the middle of it. You and I, when we started, you and I, we’re like part of the realm where people started making businesses on the internet and having these websites with ugly colors and really hard to read, black with red text. And we all loved it.

What’s a secure website? You can put a credit card on a website. What are you talking about?

And now if you don’t have such and such, would you give me money through this phone screen across two states right now?

Mahesh Guruswamy 34:32
That’s right.

Jess Dewell 34:33
I love it. I love that we’re in this really cool place of having been on that very front side and seeing how fast it’s going because I don’t know about you, but I’m looking at my son and my nieces and my nephews and I’m looking at the generations that are younger than them, right? That are three and four years old now.

And I’m looking into their future and going, I don’t even know what the jobs are going to be. This is the coolest thing in the world. The coolest thing in the world.

Mahesh Guruswamy 35:00
I can’t even imagine because back when Silicon Valley was founded, tech was more hardware, right? So microprocessors, motherboards, et cetera. And then that evolved into software and that evolved into mobile and that is now evolving.

I think AI has this sort of growth of AI is building something new foundational. So I’m interested to see what comes out of that. Let’s see.

Jess Dewell 35:28
Oh, I know. I’m super excited to see. And I love the curiosity behind it and how it is.

So it’s interesting to see that you’re hearing and that you’re feeling your sense of your businesses. This is a commodity. What does that actually do to change the game?

And how can a commodity be innovative? Which by the way, it still is the only, they’re innovating in a lot of different ways, but technology is really the driver in every sector from bed to whatever, space travel to development, sustainability initiatives, right? How do we have all these computers have to be able to do all of the things and keep it cost, right?

It’s a super cool place to be. Okay. So I want to know, we’ve talked a lot of different areas and I want to know how you personally focus on discerning what really is and is not in your control.

Mahesh Guruswamy 36:21
I mean, I think if I really think about it, the only thing that is in my control is, as I said before, where I spend my time, everything else is out of my control. So I made peace with that fact that is none of these things I can control. I can’t control the future.

I can’t control the direction of the company. I can’t control the future of my team, which is why I think a lot about where should I spend my time on? Because that’s the thing that I can control.

And in moments where in situations where I know that I can’t control the outcomes, I try to show up as best as I can in each of these situations with the objective of helping individuals, teams, companies move forward. And I also don’t have any illusions of authority or control even in my role. Because people think that executives have a lot of control.

They do to a certain extent, but you cannot just snap your fingers and make things happen. Your teams are your teams and they’re people. You can’t just tell them to go this way.

They’re not robots. And it’s not just they’re not robots, then the people you’re selling to are not robots either. So it is such a non-deterministic world we live in, which is why I don’t have any illusions of where I have real control.

Jess Dewell 37:44
Yeah. I know I don’t have control. I know I don’t even know if I have influence of things all the time.

I don’t control it, but I influence it. I’m like, really? You really influence it?

How does this look? So I’ve been thinking with Adam. I don’t think I do that either.

I think I could try, but I really don’t think I would be successful at it.

Mahesh Guruswamy 38:06
I think the way I influence works, let’s say I’ll be influenced from this place of authority. So that only works if you’re willing to underwrite the risk. So if I go, if I tell my team that, Hey, we’re going to go in this direction, but not in this direction that you want to go and I’ll underwrite the risk.

If something goes wrong, then that’s okay. That’s the influence done in the right way, because you’re not putting the burden on them for the failure. You’re putting the burden on yourself for the failure.

And I would argue that as a leader, you have to take the burden of failure all the time and not just in risky situations. But that’s a way you can influence is, okay, let’s do this. And I’ll take the heat if things go bad.

Jess Dewell 38:48
Oh, I like that. I’ll do that any day of the week. Is that how you, okay.

So is that in some of the essays that you put together for your first book or that culminated into your first book?

Mahesh Guruswamy 38:58
Yeah, I think, I don’t know if I go deep into it, but I did say one of your jobs as a leader or a manager is to underwrite risks. You can, but you can’t put it on the team to take on the risk because they don’t have the authority and they don’t have the kind of the place in the org to be able to do that. So you, you have to underwrite the risk.

And even if you’re not actively underwriting the risk, you are implicitly underwriting the risk because people above you are going, your team made the decisions, hence you made the decision. And a lot of leaders don’t understand that. And I’ve seen people throw their people under the bus in public situations where you go, oh, this person messed this up.

And even to this day, when people ask me who made this change that caused this bug or outage or whatever, I almost always never say one person’s name because it’s never one person’s fault that your entire website went down. It’s even if a person made the change in that moment that caused the issue, the question you have to ask yourself is how was this person able to make the change? Assuming good intentions, right?

And what kind of controls were in place that enabled this person to do that? What about checks and balances? And it’s a much broader question than asking, it’s not as simple as who made the change and let’s fire that person.

Jess Dewell 40:16
You want to know something, your example about the public, the public flaying, if you will, that is unfortunately something that is what people think about and what makes them worried when there will, if there will, and they don’t step up and find, to me, that isn’t, it’s anti-innovation. We say, but we go, but it’s the exact opposite. So to hear you say this and to hear this, say this, Hey, can you claim it?

Can you understand you’ve actually said it out loud or it’s implicit? And are you willing to do what it takes? And are you willing to take the heat for something that your team is doing because you okayed it?

And if the answer is no, don’t underwrite that one.

Mahesh Guruswamy 40:59
That’s right. That’s exactly right.

Jess Dewell 41:01
Talk about saving a lot of space and grace, which means maybe that’s the voice that says, I know you’re telling us all to do this, but I’m not over here, which is also a bad news situation too.

Mahesh Guruswamy 41:14
Right.

Jess Dewell 41:14
Right. Have you ever had to do that?

Mahesh Guruswamy 41:17
Well, I think so much in general, I’m pretty tuned in to not so much.

Jess Dewell 41:21
I’m glad you’re pretty tuned in. Cause I’m like, huh. Every once in a while, right.

We stumble on those things as we learn. So not even a learning. So that’s good.

Talk to me about, I want to know, I want to know what makes it bold. What makes it bold to claim your business instinct and really own what you can control is you can stay in your lane, right?

Mahesh Guruswamy 41:42
Sure. Your expertise might be engineering or your expertise might be product development, but if you ever aspire to become an executive at a, at any company, you have to understand all parts of how the business works, which is marketing sales, go-to-market customer support, et cetera. And you can make, you’re going to push the company in the right direction.

If you understand all those aspects of how a company is run. And ultimately it comes down to, will you feel comfortable putting your hand up for a complicated, messy situation or a task or a project? I encourage like leaders to raise their hands, especially when things look like they’re on fire.

Cause then it’s kind of show it sends a signal to everybody that yeah, this person is willing to dig in, even if it is not in their direct purview. And in terms of like authority, the rules of authority are just made up, right? Cause it’s what I realized as a leader is you’ll get authority in a specific domain or a direction if you solve messy problems for that direction.

So I have people from marketing reach out to me for advice gone, okay, we have this thing. I want your opinion on this. They reach out because in the past I’ve helped them resolve like customer issues because they’re like, how will this message land with the customer?

And I can like, okay, I can give them the insight because I’ve been in that spot before. So I think it comes down to that, not staying in your lane, but not stepping on people’s toes. Not so much about, Hey, I think your decision is wrong.

It’s more about, do you understand each domain deeply? Maybe not as deep as you understand your own domain, but do you understand them enough to start forming points of views and how or where the company should go? And the more thoughtful you are about your approach, the better it’ll like resonate with your peer group and even the company.

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