The Real Mindset Behind Promotions in Product Roles | Ibrahim Bashir

The reality is in an operating role, there's so much operating overhead that even if you said, look, my goal is just to mentor, coach and elevate people, you're not going to get to do that 100% of the time. Every time you distract product leader from respond to this, show up to that, help me sell this, blah blah blah, there is less time for them to just sit and think and marinade. And so my advice really to everybody working with heads of product is you are Ibrahim Bashir is a cross functional leader in the technology domain with extensive product management experience, scale scaling, user focused, outcome oriented product and engineering organization. He's on the product team at Applied Intuition.

I feel like if I'm a manager I will have more control or I will be able to do more things.

A lot of people want to get into product management because they're like, then I'll make the decision. And I would just take a pause and say, why is it so important for you to decide? So one is just my productivity stack is out of control in terms of how I'm organized. I'm constantly inbox zero. The other thing I would do is you have to get very good at saying no and letting things drop. Which I think for a lot of people in tech, in product, in management, they don't want anything to burn.

Hello, welcome to the Priyanka Shinde Podcast where we dive into the art and science of strategy, execution and leadership. I'm your host, Priyanka Shinde, author of the Art of Strategic Execution and a consultant for tech leaders. In this podcast, I bring you candid conversations with top executives, startup founders and industry experts who are driving innovation, delivering results and staying ahead. In today's competitive landscape, we will break down what it takes to tap into founder mode and turn vision into action. If you are serious about elevating your leadership and execution skills, make sure to subscribe on your favorite podcast platform or YouTube. It helps the podcast and ensures you never miss an episode. Hi everyone. Welcome to the Priyanka Shinde Podcast. Today I have a very special guest, someone who I've been following for a long time, Ibrahim Bashir. Ibrahim has been creating software for nearly 25 years. He was most recently an executive at Amplitude where he served as the VP of Product. Before that, he scaled new products at Box Service, Infrastructure at Twitter and the Kindle business at Amazon. He's passionate about building teams, shipping products and repeating outcomes, frequently speaking about these topics at industry events and writing about them on his substack newsletter, Run the Business. Welcome. Ibrahim really Excited for our conversation today.

Yeah. Thank you for having me, Priyanka.

Yeah. So tell us a little bit more about what you do currently and your journey.

Yeah, well, I mean, you did a great job of keying it up. You know, I've been in software development for a quarter of a century. Sounds like a very long time when you say that. You know, have worked on everything from E commerce to hardware to social media to, you know, most of the last decade, B2B SaaS, both horizontal and vertical SaaS. I would say what I do currently. You know, around Thanksgiving last year, I left my full time operating role and have been trying to make a go of it as a creator, coach, advisor, consultant. So that's what I'm currently working on and I had given myself six months and six months is coming up. So we're going to do a little bit of like state of the business and figure out if we, if we continue for another couple of months or if it's time to go back to operating.

What was like a moment or pivotal moment where you made that decision to shift from working at companies to doing something on your own?

Yeah, I mean, first I would say it's, I wouldn't treat it as a one way door. I think, you know, there are periods in your time in your life when you're really learning exponentially and operating to get that learning and then there's moments to share that learning and disseminate it. Right. And in an ideal world you can go back and forth between operating and sharing, operating and sharing. I think historically what tends to happen is our industry is people kind of work themselves to death and then they take a hard retirement and they're like, now I just talk about what I used to do and I don't think it has to be that binary. So part of it was just this realization for me that it's okay to have a bit of a portfolio career. Right. Always be learning, always be operating. And you can sort of dial it up and dial it down was number one. Number two is, I would say, you know, I've gone on a journey in terms of my professional North Star over the last couple of decades. You know, in my first job out of college, my North Star was my income should be more than my expenses. Like I had this survivor mindset and so that's kind of what drove me for a while. And eventually you make more than you're spending and then you say, now I can make some choices for myself. So then my North Star became working on projects and products that I was interested and excited by. So it was almost like an excitement meter. Right. How high is your excitement meter? And you know, I worked on some pretty cool stuff at Amazon and at Twitter, and I would say that excitement meter got pretty high. Right. But eventually you kind of keep chasing that high, and I don't think that's a scalable or sustainable way to operate. And so when I eventually got into people management, I would say, you know, you sometimes get some bad advice where you start thinking about the number of people or the size of org as your North Star. But, you know, you could manage thousands of people and not know their names, not have any impact on their careers. And so I would say about a decade ago, I settled on a North Star that I've been pretty consistently pursuing, which is the number of people for whom I have changed the arc of their career, for whom whenever they have any kind of career situation, they're having a kid, they're thinking about quitting, they're starting a company, they don't get along with their boss, I'm the first person that they call. That's the number I've been trying to optimize. And you know, when I think about operating roles, you're optimizing that role by your org. Right. Sometimes you can have cross functional or peer mentorships, but really you're limited by the size of the company. And so then I started saying, well, why should I be limited by the size of the company? I started coaching and mentoring and advising people outside my day job. And I think in this last few months, you know, as I've been trying to make a go of it as a solopreneur with run the business, the world is my oyster. I can advise, coach, consult with anybody. Right. And so I would say in terms of the moment, that really led me to that belief, I would say I just started getting more and more messages from readers and viewers and just random people I had helped out saying what you helped me understand, sort of figured out our product strategy, it helped me in annual planning, it made me look good in front of a CEO. And I realized the cohort of people that I could help shape and influence as leaders is not limited to the company I'm at and I should really give it a try.

Yeah, I think you make a very important point is like your, your influence, your scope of influence is, goes beyond your company. And I feel like there's a lot of reward in that. That is not, you know, captured by any performance review cycle or anything like that.

Yeah, I mean, if you Think about it, you know, within the confines of a company. And I'm not saying anything negative about any company, but the reality is in an operating role, there's so much operating overhead that even if you said, look, my goal is just to mentor, coach and elevate people, you're not going to get to do that 100% of the time. And I think in a lot of organizations you don't even get to do that 50% of the time. It becomes 10% of the time because you're like, I'm running to this meeting, I have to respond to this email. And you know, I find a lot of people are really not even able to focus on the craft. They're just focused on the gymnastics of what are we shipping, why are we shipping it, having the same conversation again and again. And so I think, you know, you can get burned out from operating. It's good to recharge and purely focus on teaching and educating. But then in order to keep it fresh, you always have to go back and learn again what is new and cool and operating.

Yeah, I feel like there is a lot we can touch upon the, on the people management aspect of it and like what people think is and then what you kind of touched upon a little bit. So we'll get to it as well. But I really wanted to kind of share, like emphasize on the one way door thing that you mentioned about this, you know, switch that you made and that our careers can don't have to be like a very specific linear structure or in only one way or the other. There is so much variety that can happen there and I feel like that really shapes who you are as a professional.

Yeah, I mean this is really feedback for the LinkedIn profile page team. The layout of the profile necessitates, it's like a linear read. Right. But the reality is there are branches and loops in your career. And so right now, you know, what looks like a linear progression is really me kind of like doing a little bit of a circular thing, which is fine. You know, if anybody from LinkedIn is listening, please make that possible.

Yeah, I hope so too. I mean, there is, yeah, there's something about LinkedIn profiles nowadays. I've heard a lot of people say, like they cause a little bit of anxiety because people are, you know, reading all these things that are being posted or, you know, the title inflations and things like that.

Yeah, it's not good because people really see a finished product that's been really polished and it's, that's not really the reality. Of how it got there.

Right.

Yeah.

I'm sure you have had even challenges like over the last six months as you, you know, go out on your own and do things. Any, any specific challenges that you can share and, you know, advice around it.

Yeah. You know, one of the trickier things I learned is being good at your craft and having a network of people who understand that and respect that is not really enough to go find clients who want your coaching and advice. In fact, I think a lot of times the algorithm and sort of the decision makers really focus on who's famous. And so it kind of creates this weird incentive structure where you're spending a lot of time trying to be known for being known rather than being known for being good at your job. And so I really had to sort of publicize myself in some circles to say, this is what I'm trying to do. This is why I think I'm good at it. But I think, you know, the flywheel doesn't really start turning until you start to have one or two successful clients. So there, there was a minute there where I was like, oh, I think I've made a huge mistake. I don't think anybody really wants my advice. And then slowly one came along and I was able to broadcast it. And that led to two and then three. And know some people don't want me to talk about it publicly. So I have more than is publicly made available, but that's fine with me. Right.

So, yeah, yeah, I think that it's one of those things again, that I feel like LinkedIn needs to listen to. Is. Is there's, you can always game the system. So like, when we, when we start thinking about, oh, now I have to post in a certain cadence or like, you know, I, I have to sub, I'm submissive to the algorithm cards over here. You start focusing on something different than what you really intended to do. And I found the same for myself as well.

Yeah. I'll mention two things and I think, you know, this goes to like, when you're in an operating role, you're so metrics oriented that you almost get trained. Whatever the metric is, you're like, let me optimize it. And I think it's good every once in a while to stop and say, is this metric connected to the business value that I'm trying to operate? So I'll give you two examples. One was, I recently did a webinar for a company that was like, look, we think you're, you're going to draw the right audience. So we Want you to do this webinar. And there was like a dozen people on the call. And I felt really bad. I was like, oh man, only a dozen people showed up. And you know, it's almost embarrassing. I was like, I thought there would be hundreds. And they said, oh no, don't worry about it. They said, those 12 people represent our top 20 account based marketing list. So even though the number is small, it is dead eye in the bullseye in terms of the audience we're trying to capture. And it was kind of a reminder to me that like, number of attendees is not a good metric. It's a simple metric. It's an easy to understand metric. Right. And if you're sort of uneducated about field marketing or webinars, you might say, well, the webinar that attracts more people is maybe the more successful one. But if I can connect people with, you know, audience to service provider, I think that's a more interesting path to value.

Yeah, I agree. And you know, sometimes you get all of these advice of like, do it this way or do it that way in order to kind of, I don't know, put yourself out there or become known. And not everything works out or not everything might align with your vision or values. Right. Speaking of advice, you've had a long career. I'm sure you have received a lot of advice. So what is one best piece of advice you've received and one worst piece of advice you've received?

Yeah, no, it's a good question. You know, I would say earlier in my career, you know, we all have imposter syndrome on some axis, right? Do I know the domain? Am I a good enough speaker? Am I a good enough writer? Do I understand people? I would say I was always very confident in my technical abilities and a lot of the hard skills. And I would say for whatever reason, I was not as confident in my ability to read with and interact with and engage with people. Although over time I realized I'm a very emotionally intelligent person. And I would say so I actually got and accepted lots of bad advice when it came to navigating people. So one of the first pieces of advice, the first time I became a manager, I was a senior IC programmer and I took over the engineering team. And the advice I got was, we want every programmer on this team to be like you. So whether you need to hire or up level them or send them to training, whatever you need to do, they should all have the same throughput as you. So I went on this journey of like cloning myself and you know, the reality is it's nobody wants to work for themselves, be managed by themselves, and have a group, peer group of themselves. You know, I listened to podcast with Brene Brown once where she said, you know, they tried to breed like the ultimate rooster and they just started like pecking at each other and trying to kill each other. You can't have too much of the same thing. Like, diversity matters from cohesion and collaboration perspective. So that was some really bad advice I got, which was clone yourself. And I was like, no, I should absolutely not clone myself. I should compliment, right? What do I bring to the table? What do others bring to the table? And it took me a while to sort of like let that bad advice pass through my system, have some bad managerial experiences and then try again.

And.

And then I would say the best advice was also around people, which is if you're a manager, because you're the manager, you're not a good manager. If you're the manager, even if you didn't have the title, then you're the right leader. And so I really. It was a former boss who kind of gave me this advice where we were in a situation where the team had grown, we were all peers, and there was a push from me and from others to say, well, he should manage this team. And my boss kind of made me wait for a couple of months and he said, I want them to follow you even if you're not their manager. That's how I want this team to operate. They should say, this is the leader of the team, irrespective of title. And so I thought that was great advice and great coaching because it forced me to operate with a sense of humility and empathy and pure mindedness that maybe I wouldn't have had if you had that manager title.

Right, yeah, that's really great advice. I mean, it's not something that happens or you hear about every day where you are grooming somebody to become the manager, but you're helping them understand how to become a leader first. And that's something I'm also very passionate about, is your leadership doesn't come from a specific title. Your leadership comes from the traits or the behaviors that you exhibit. And absolutely, I think I agree that becoming that leader that people are willing to follow is so important than becoming a manager at the same time, I mean, you have had a lot of experience on the people management side, and there are a lot of misconceptions also about becoming a people manager. Management in general. What are some of like the top two or Three things that you can think about that you know, important for others to know who might be stepping into this people management or want to get into it.

Yeah, I would say a few different things. One is sometimes people get into people management because they think they're the senior most. I see. And really that's touching on a different kind of dysfunction, which is we don't have a career path for really senior ICs, especially in product. Right. So if you're really good at strategy, you're really good at delivery, and you want to make bigger and bigger size bets, you shouldn't have to get into the management ladder to do that. So I would say that's sort of an anti pattern in a lot of organizations is number one is, you know, you shouldn't be like, okay, my IC career is at an end, I need to transition to the management of ladder. That's a, that's a, a lack of ladder sophistication more than anything else. That's number one. Number two is I think people don't approach management with the same degree of rigor and craft that they do with the hard skills. So for example, we're living in the age of AI. Everybody's taking a boot camp and playing with tools and reading all the latest blogs and I'm like, why don't you do the same about human psychology and organizational design and what makes people tick? Right. And I would say, and I'm not saying there's, I don't have any books off the top of my head, but I would say I did a lot of reading and studying the craft of people leadership in order to get better at it. And I think one of the misnomers people have is, you know, some people are just natural born leaders. Some people are just loud voices. And I'm like, that's not actually how it works. A good people leader actually has empathy, has emotional intelligence, has the ability to connect the dots for people who are struggling, has the ability to motivate people and it actually requires quite a bit of energy. I would also say I'm not a fan of how much disdain there is for management. People talk about management like it's a necessary evil. Oh, we had a layer of management, we had to remove it. Oh, the managers are in. A really good manager is worth their weight in gold. A really good manager will take a team of 10 and have them performing like a team of hundred. And so I really believe in management and I believe in structure and I believe in one plus one equals ten. I think what's what's an issue is there's too many people in management who got into it for comp. Reasons, for career ladder reasons, and now they're stuck because really they missed the craft, but they didn't see any way to progress and do the craft other than that.

Yeah, I've seen. Similar to what you're saying is a lot of times people get into people management for the wrong reasons. Sometimes I've heard about, like, I'm sure you have gotten this too, is like, I feel like if I'm a manager, I will have more control or I will be able to do more things because I don't have the time to do it.

Now that, you know, that's another issue is. And it applies both to management and product management, which is a lot of people want to get into product management because they're like, then I'll make the decisions. And a lot of people get into management because they're like, now I get to decide. And I would just take a pause and say, why is it so important for you to decide? Why is it so important for you to decide? And I think when people really reflect on that, they say, you know, because I feel like I don't know what my workload is going to be. I feel like I don't agree with the strategy. I feel like I. And there's a lot of. I feel, I feel, I feel, and I think at some point solving those issues versus putting people in management who maybe don't have the heart for it or the stomach for it. You're. It's really quite a dangerous and unhealthy thing to put somebody in charge of 2, 5, 7, 10, 50 people who really couldn't care less. Right. It's a very careless thing to do. So I treat management very sacredly and I think it should be treated that way in all organizations.

Yeah, you really touch upon a very important thing here, which is like, yeah, if you put somebody in charge, it's now that radius of impact is not that one person or two people. It's like five, 10, 50 people. And that's a lot. Yeah, it's kind of goes back to this motto that I follow, which is with great power comes great responsibility. Not my own, of course.

You know, I liken it back to sort of almost like family dynamics where growing up, if your parents were around and they said, you're in charge, that was everything. It was like, I'm trusting you. Be respectful, be kind, feed people, don't burn the house down. And so I treat it that way. Which is somebody says manage my people, that's a sacred duty.

Yeah, yeah. I agree with your experience being a people manager and helping, you know, product teams build successful products. Like what's your secret to like turning all of like, you know, the creative chaos that might be there within the team into a repeatable success pattern?

Yeah, look, I would say, you know, the number one thing a product person should do is create the sense of clarity for the cross functional team around what is the problem, who has the problem, how do I repeatedly find that problem in the market and what is a good solution that we should build that's differentiated. And I'll just make a point about AI, even though you didn't ask. I think you can put all the AI tools out there. It's not going to be a substitute for that judgment making. Right. I think it's a great asset to have if you were drowning in ticket management and reviewing zoom recordings and generating slide deck upon slide deck. So I think AI copilots as an assistant for a lot of the overhead of product development and release management I think is amazing. But it's not a substitute for I really listen to this customer and I have a perspective on what they're saying and I think it's universal in our user base or in the market. Right. So I would say, to answer your question, what I really look for and what I try to do is deep, deep customer empathy and understanding. And there's a bunch of ways you can do that. You can directly spend time with customers or you can spend time with proxies of customers or you can do both and you can look at data and you can look at qual. And I think the real job of product management is to take all the inputs. And that's why I'm so excited about AI, because AI can say give me all the inputs and then I'll try to make sense of it and, and then you decide how you want to weight it. You decide whether what the sales team is saying this quarter versus what the support team has been saying for five years versus what your power users are saying versus what the gardener analysts told you, how much to weight each thing. Because I, I really love this quote and I use a lot of quotes in my, in my day to day from Rumi, which is, you know, the truth is a mirror that shattered and fell on the earth and everybody picked up a piece of glass and said I have the truth. And I feel like product management is a little bit like that where you can talk to a team and they'll say, this is what's happening. This is. I can tell you because I have a ticket, I have a customer, I have an anecdote, I have a story, and it is true, but it's not the truth. The truth is fragmented and your job is to stitch it together fast enough such that you can solve the problem and get commercial success. And so that is what I try to do with most product teams is take all that chaos, which is all these inputs and all these ideas, and say, let's arbitrate the truth and how it will be revealed to the market. Because if you come up with something that is partial truth, the market will reject it and say, this solution doesn't solve all my problems. If you come up with something that is so far ahead of its time, is so forward thinking, the market will also reject it because they don't have the maturity to actually utilize it. Right. So you need something which sort of meets the maturity and solves the problem, but is forward thinking enough that it grows as user literacy and maturity grows.

I really like that what you shared, the quote about truth and it is true. Like everybody has, like, this is. This is the truth that I have and, or, you know, sometimes it is like, because so and so said so and bringing all of that together is, is a challenge for a product leader. But that's what you know, you're there for. And at the same time, all of this balancing act that I'm sure you also have to do, in addition to sort of reigning in the chaos, especially between strategic planning and, you know, execution, or if you think about innovation versus consistency, how do you think about those aspects and balancing them?

Yeah. So look, if you can first agree that fundamentally we're playing a game of judgment calls, there's no precision here. Then you can start to say, okay, then if I'm tackling these problems, really the best thing I can do is sequence them in the right order. You know, in a long enough horizon, everything that customers are asking for will be built and solved. It's just a question of what do we want to do now next and later. So I try to bring time as an asset to sequence it out because, you know, I'm sure your listeners have this problem a lot. They're like, I have my plans, I have my roadmap, and now there's a big deal that's disrupting the roadmap. Right. And I'm like, yeah, that's fine. We just need to talk about whether we believe in that more now next or later. Oh, we were on our way and everything was fine. And then the CEO had a brilliant idea and now what do we do? It's disrupting us. And I think people get so rigid about their plans and I think it's okay to say, I'm learning new things, let me shuffle things around. So I'm a big believer in fungibility, in shuffling the decks. And, you know, I used to work with a guy who had a very interesting job. He was basically chief escalation officer for customers. And he used to tell me, you know, now next, later is great. I would love a bucket called Never Never. We will never do this because we just don't believe in it. Right? So, for example, we're mobile first. We will never build this desktop application. We are cloud native. We're never going to do this on prem thing because the customer will show up and say, you know, I've heard good things. I just, I need you to take what is a core differentiator of your value prop and just bend that for me and I'll give you a million dollars and sales will go after it. And the CEO will get, you know, excited about it. And your job is to say from a judgment call, I'm saying this is now, next, later or never. I also really love. I know somebody who works at Asana and one of the things they do on their roadmap is they put notably not. And I think notably not is a great category to say we heard you, but not right now. But we just want to acknowledge that. And I think a lot of times customers just want to be acknowledged because they feel like they're not being heard. Heard. Right. And so, yeah, I'm actually forgetting what your original question was, but hopefully I. There's somewhere in there. I answered it.

Yeah, we were talking about balancing between strategic planning and execution or innovation and consistency. And I think the point you're bringing up is you have to prioritize. Sometimes you b. Sometimes you prioritize planning, sometimes you prioritize execution, sometimes you prioritize innovation. And it reminded me also, like, you're no, no now, next, later or never reminded me of this concept of like, no for now as well. For sometimes when you're thinking about prioritization, it's very difficult for us as humans, be it in the professional, like, work setting or even in our own priorities, where we feel like really overwhelmed because we feel like we have to do everything now or we are going to be. It's going to be a failure or we might deem ourselves as failed. And this whole no, for now concept that I heard a lot through my coaching training as well really helps because then it kind of puts that time piece in perspective that you mentioned. I just got reminded of that because I've talked to so many people and said, what if you say no to this for now, it doesn't mean it ends or this feature, you know, for now, maybe later. Right. So I, yeah, I really resonate with that.

I, you know, one of my practices that I do when I'm in a head of product capacity is anytime there's a good idea, it doesn't matter where it's from. One of my PMs, the CEO sales, I always do them the courtesy of take the idea and flesh it out a little bit. I'll write like a one pager on it. I'll be like, this is my understanding of the idea. This is what would have to be true about our technical capability, our workforce, our customer base before we did this idea. And I always tell people there's no bad ideas. And so I just kind of, I flesh out the idea and I put it in a Google Drive folder and I'm like, every good idea, the time will come. And eventually it comes along and it's like, we've thought about this before, is now the time? And I got the idea from this concept called a spark file, which is every time you have an idea you go and you write it down, but the next time you have a similar idea, you go put a hash mark saying, okay, second time this has come up, right? Third time, fifth time. And so I have an idea file going back a decade where I'm like, I've thought about this now 10 times, right? Something is telling me now is the moment to go do this. So that's number one, is it shouldn't be an arbitrary, are we building it or are we not? You can do more than build and not build. You can do. We did some prototyping, we did some ideation, we did some customer calls and then we parking lotted it, right? So that's number one. Number two, to go back to your point about, like how do you balance innovation and all that stuff? It really depends on where your product is in its journey. If you're a single product company that has yet to find product market fit, all horses should be running towards finding product market fit. If you have a single product and you're trying to establish a new flywheel to connect to it, then that traditional product should really be harvesting what you've built and maximizing the playbook while the next Product is finding product, market fit. Right. And I would say so it's really a question of assessing the market and saying how much are we in capitalizing on the solution we've built versus the need to build new distribution and new techniques that will pay off down the road. And I always say product's job is to lay out the trade offs. So to go to your sales team, marketing team, CS team, finance team, and your CEO and say, this is my opinion on how we should phase this stuff. If you have a different opinion, if you know things I don't know, let's talk about it. Where I push back is when people say, I want all of it. Now, that's basically a failure to make a choice. It's actually a failure to even have a discussion. It's a failure to even have a framework on how to have the discussion. And you know, I advise a lot of people and whenever they're in that situation where they're like, I understand everything you're saying. I have a framework, I have a mental model, I know how to manage the discussion. Nobody wants to have it, they just want everything. Yesterday, I would say it's time to look for a job. That's not an environment where people understand the realities of making choice.

Yeah, I think it's very important. And I really like the idea of the. What is it, the idea file or the spark file? I feel like I'm gonna seal that and use it as well.

I have one idea on there that I keep coming back to. It's a smart refrigerator that actually just looks at everything in your fridge and tells you what your next meal should be. Because it's, it's partly like, what caloric needs do you have? It's partly like what's about to expire. It's, it's a use case of one right now. I really want this because I'm like, oh, no, this went bad. I didn't cook it. So I would love a smart refrigerator.

Yeah, there you go. I mean, there's so many things like that. You, you kind of sometimes have these like fleeting thoughts in some sense. It's like, oh, this kind of a product would be so good. And then you kind of just, you probably noted it down. But most of us would like just let it pass and not think about it again.

Well, selfishly, I, I play that role manually right now. So my wife will be like, what should we have for dinner? And I'm like, oh, that broccoli is about to go bad. We should cook it. And I'm Like, I would love to get out of that business and automate it.

Yeah, there's so many great tips you had in there. Can you share, like a conventional, unconventional tactic or hack that you have used or implemented that has, you know, dramatically like boosted a product outcome or maybe even a team perform. Team's performance?

Maybe I'll choose team performance because I would say, you know, Most individual productivity hacks, 8, 1, there's a lot of literature about, you know, biohacking time hacking, productivity hacking, etc. So I don't want to bore your listeners, but I would say getting more out of a team because you're playing with a larger population, it's really a big end. And so there's a lot more you could do. Right. So I would say one hack I kind of stumbled into, I stole it from one of my directs. That's really been a great unlock is actually separating one on one meetings from career coaching. Physically separated, where a lot of times people will say, oh, you know, in our next one on one, can we talk about career? But then something comes up and then you give it five minutes, right? And so one of the things I started doing was having a monthly one hour, you know, in person, walk and talk, dinner, whatever you want to do. That's all career. And the reason it's such a huge unlock is, let's say, I'm oversimplifying. You have two types of employees, probably three types. One is like under non performers that probably need to be managed out. Two is the squishy middle that's like, you know, doing decent work, but kind of needs a lot of tlc. And then the third is top performers. Any and all of those segments will benefit from that dedicated one on one. Because if you're in the middle of the pack, where you drift is you're like, is what I'm doing, Is it a priority? Does it matter? How does my work connect? They lose the plot a lot. And having that career conversation can really get a lot of more mileage because they're like, oh, yes, now I remember why this matters, who this matters to, what it matters for. Right? It's like almost like a cheerleading session, one on one for your top performers. It's almost a reminder, like your top performer, you could be doing this anywhere. But this is why you should do it here. This is why this is the best environment for you to be doing this here. Right? And so I would say this idea of having dedicated career time and a lot of times when I propose it to people, they're like I don't know that I need that. You know, I don't think I'm up for promotion and you know, I'm doing good. But something always comes up where they're like, I'm really glad I have uninterrupted one on one time to just talk about my career, my ambitions, my frustrations, my perceptions, what's going on with my skip level, whatever the case. And so that's been a huge team unlock. Obviously it requires time. A lot of my solutions require time and people don't want to give time. But. But yeah, that's why.

Yeah, so you're recommending like this is scheduled separately from your say weekly one on one and ideally you're doing it in a different setting. So like a physical either walk or coffee or whatever that might be to get you out of that setting. Say you're on a zoom call or something like that. It feels very like I have to talk about projects and products and things like that.

Whereas, you know, whenever I hire somebody or inherit somebody, I always tell them, hey, our one on ones don't need to be status update. But it doesn't matter how many times you tell them. Every other manager they've had has trained them to do that. I'll give you the reverse of this trick as well. You can use it to manage up as well. So I used to have a boss, brilliant guy, huge scope and you know, our one on ones, he was always 10 minutes late and then he was always distracted and it was like we never got anything done right. I'd be like, I have some really important stuff to talk to you. And you know, one day I was just sitting there and he's like, what's on the agenda? I was like, nothing is on the agenda because you're 10 minutes late and you're looking at your phone and we're not really going to have a structured conversation, so what's the point? And he's like, well, I just don't have time in the day, I just don't have time. What do you want me to do? Right? And I was like, when do you have time, time? And he was like, honestly, it's not until dinner that I can sit down and have break. So I said, I'll make you a deal. We can Skip our weekly one on one which is 30 minutes and you give me a two hour dinner once a month. So I will literally, you're my boss and I won't have a weekly one on one with you, but I get a two hour dinner once a Month. And we just started being way more productive then. And so I would say, just like you can give this as a gift to your team to say you have dedicated time with me to manage your career, offer it as a gift to your boss or skip level to say, I need access to you. You tell me when and where and how. And it doesn't have to be dinner. It can be, you know what, I play golf, or you know what, I go work out at this time, come with me, I go for a long walk. And so find people when they're at their best and most professionally productive and meet them where they are. I'll give you one more, because now I'm on a roll. I have this mental model around people. It's not, I don't think it's meant to be around people management. I read a neuroscience white paper once called scarf, and it says basically, people are motivated by one of five. SCARF is an acronym. Status, Certainty, Autonomy, Relatedness, and Fairness. And, you know, I'm a little bit like the Terminator. Once you see this model and you look at people, it becomes obvious who they are. Status people are like, well, this is my title. What's your title? Certainty people are like, are we going to have a job tomorrow? It's really important to me to know that I have a job, right? Autonomy people are like, give me the project and get out of my way. Relatedness people are like, who am I collaborating with? Who do I eat lunch with? Are we friends? And then fairness people are like, I just want to know that there's equity here. Like, whatever bar I'm held to is who the other person helped to. And once you can sort of figure out what makes people tick, you can really get ahead of a lot of individual problems and a lot of team dynamics problems, because you understand you have to do this translation as a manager between what motivates certain people. And by the way, people are not one size fits all. So you can be certainty driven at work and be status, status driven socially and, you know, something else in another walk of life. But it's a little hack that I've started using.

That's a great way to think about people at the individual level rather than your team as a whole of entity. Because your team is made up of such diverse people. Everybody's, like you said, ticked by something different. And so managing a group of diverse people isn't always easy. I mean, there's so many different things you might want to do, right? You want to create a culture of creativity or accountability or ownership and you might have to approach each individual differently based on what motivates them.

So I'll share two more things. One is, you know, there's a lot of managers and leaders who believe this is my playbook. I was hired to run the playbook, and the playbook runs a certain way, and I have a certain style. So it's my way or the highway. And I'm not saying that's a bad model. It's a functional model. It can even work in the right place at the right time. But it's not a good model to get the best work out of people. My philosophy, and I think this is the essence of servant leadership, is to say, how can I be the best manager for this person and that person? And really, that requires you to be a different manager for two different people. That's what is required. It's a lot of work as a manager, but you're going to get the best out of people. So one is, I believe in fungibility as a manager is you're actually treating people differently. The bars are not different, but your approach is different. That's number one. Right. The other thing I would say is, you know, a big part of navigating that I'm managing a team of individuals, but they're also a group is creating psychological safety. One hack that I've been using for probably 15 years is I read a study once that said if in a meeting, a person talks at the beginning of the meeting, they are more likely to talk throughout the meeting. So, meaning if you get everybody together and say, we need to make a decision and you ask one person's opinion, that person feels comfortable talking now, but everybody else is quiet. And that's how bad decisions get made. That's how problems aren't highlighted. That's how issues don't get surfaced. So I try to make a point anytime we have a group discussion to break the ice in some way such that everybody is forced to talk and they get over that mental hurdle of, like, I haven't talked yet. Right. So at this point, I probably have a thousand icebreakers that I do in my team meeting. And it's just a ritual to get everybody comfortable.

Yeah. Is there a list somewhere?

No, Honestly, it's. It's very topical in that whatever is happening that day, I'll just kind of manufacture and I'll be honest. Sometimes they're wild successes and sometimes they're terrible. People are like, this is so terrible, this icebreaker.

Yeah. I just read your post about the rock paper scissor thing. So we have one over there. I wanted to ask you, based on what you said, managers need to have a lot of time to do everything, especially when thinking about the team at an individual level, at a group level.

And.

And yet sometimes managers are squeezed, right? Like they're getting squeezed from the top and they're getting squeezed from the bottom. So what do you think needs to be done so that managers can truly do a good job of being the manager that the team deserves and at the same time have a meaningful impact for the company?

Yeah, a few different things. And I can share a little bit of my own experience and I don't, I'm not pretending that everybody can, can do it. Number one is I think there needs to be like a reckoning around the purpose of management. The purpose of management is to unlock the output and throughput and quality of a group of people. I think if you look at it from that lens, there probably needs to be a lot less managers and more span of control. Right. So that's number one is I think a lot of companies need to rethink their hierarchy and a lot of companies tend to go off ratios and I'm like, I don't understand. It's not, it's not a spreadsheet where they're human beings, right. And so it might look different in your company, in your organization, it might look different between product versus design versus eng. But I think one is you need to figure out the right ratios of managers to actually have. Right, that's number one. Number two is management needs to be treated as a full time job. You cannot be an IC and a manager. And I know a lot of places have that and I'm not opposed to it as a transitory step. But if it's a permanent balancing act, you're either doing a disservice to the individual contributor work or you're doing a disservice service to the management work. Right. So that's number two. Number three is one of the ways I've survived because you know, every job I've had I've had significant individual contributor responsibility even as a manager is to become hyper efficient. So one is just my productivity stack is out of control in terms of how I'm organized, how I follow through on things, what I let dwindle, I'm constantly inbox zero. I don't recommend it because you need to be like operating at a, at a scale that maybe a lot of people don't want to operate at. The other thing I would do is you have to get Very good at saying no and letting things drop. Which I think for a lot of people in tech, in product, in management, they don't want anything to burn. And you know, I coach a lot of heads of product and a lot of first time heads of product. And I always tell them, you know, they're like, These are the 14 things I have to do. And I'm like, which of these fires are you going to let burn? And their answer is usually none, nothing can burn. And I'm like, no, but that's. You are going to be put in impossible situation after impossible situation. So you have to decide to let these fires burn. And your job essentially as a header product is to make the right calls on which fires to let burn. And one day eventually you're going to make the wrong call and that's the end of your head of product at that company. That's the nature of the role. It's a very lonely role and it's a firefighter role. And eventually you're like, okay, I let a fire burn for too long. I made a bad judgment call and now I have to look for a new blight. So I would say, yeah, those are some of my ideas. But I do think, you know, with the emergence of AI, I do think in a post Covid world where we're operating all on video half the time, there really needs to be some thought and care put into what does it mean to be a people leader in this day and age and who is cut out for it and how do we know they're doing a good job? Right. It can't be as simple as hey, I pulled your directs and they were all thumbs up. And it's like, I mean, they're afraid for their jobs. What else are they going to say? Right. And so I think some thought needs to be put into what does it mean to be a manager and how do we evaluate good managers?

Definitely, I think feel like, and there's so much happening in the last year, two years also with respect to like, oh, we're gonna get rid of manager layer or more, more people reporting into one. But then you don't have the right structure, the right setup in order to Support either the ICs or the managers themselves.

Yeah. You know, I think those hard cuts are throwing the baby out with the bathwater. You're probably eliminating some really good people leaders and let's be honest, you're adding a ridiculous load on the remaining ICs. So I think, you know, but that's the reality of a lot of Businesses is how can we sort of overload for the time being. And there's not a lot of thought into, well, how do we actually come up with a sustainable thing? Because everybody's worried. Falling behind.

You mentioned, like, coaching a lot of product leaders and executives. And as you've been coaching so many people, what is like a surprising insight that you have gotten while mentoring and coaching these folks?

I'll share a couple of things. One is nobody is really doing product thinking or product craft. They are drowning in stakeholder management. They are drowning in status updates. Even at the head of product level. They are constantly responding to the latest fire drill from a partner, from a stakeholder, from a customer, from their executive team, from the board. And I think, you know, if I, you know, look, product gets a lot of slack. Products had a really good run and, you know, product in, in some ways is less accountable for some things that sales is really accountable for. Engineering is really accountable for, CS is really accountable for. I always tell people every function. If you said, I need Ted headcount, you're signing up for something, right? Sales says, I need 10 more account reps. It's like, how much more quota are you signing up for? Marketing says, I need two more PMMs. It's like, how much more pipeline you're going to sign up for? Or the support team Sundays, I need 50 people. In this geography, you'd say, how much is the SLA going to improve versus product says I need three people. It's like, well, what are you signing up? You're signing up for more leverage, right? So product I think, is in a privileged position. Let me first say that. But on the flip side, I'm starting to feel bad for product because everybody's piling onto product. And the reality is I'm like, every time you distract product leader from, respond to this, show up to that, help me sell this, blah, blah, blah. There's less time for them to just sit, sit and think and marinade on the market and the customer and the Persona and the problem and the solution. And I always used to tell people if I ever had an hour and a half to myself, I was going to do some really good product thinking. It would probably elevate my team for a whole quarter to be like, he got to sit and just like think and write and get clarity for a time. And then he created Clarity for 10, 15, 20 people who then created Clarity for 100 engineers. I mean, think of the mileage you get out of that. And so my advice really to everybody working with heads of product is you are constantly thrashing and distracting them and they cannot do the job, which is to steer the product in the right direction. Really. They've just become glorified roadmap managers and release updaters and status providers. And I don't think that's healthy. There's also something unsurprising, which is a lot of product leaders are dealing with very impatient people. And I was really thinking about this. You know, I think we've really elevated impatience into an asset from executives and leaders, and I think it's a vice. I was reading somewhere that people who've really struggled in their lives and their careers, when they arrive at a particular place, they have a lot of patience for other people who are trying to figure it out. And so I always think about leaders who are impatient. People are like, that's a great leader. You know, they're just, they're frustrated that the world isn't moving fast enough. And I'm like, actually, you took a shortcut to leadership. You're in a leadership position without ever having had to struggle and become resilient. Because if you did, you would be more patient with people, with process, with technology. I'm not saying be less ambitious. I'm saying be kind and be more patient. So that's not surprising at all. But it is a stark reminder how much impatience there is. And it tells you a lot of people get into leadership positions by signing up for ridiculous goals that aren't achievable and then they put that stress on the team.

Yeah, I feel like when you talk about impatience is like there's this sense of urgency, which was supposed to be a good thing, is then turning into impatience, which is not such a good thing. And it's. Yeah, somewhere along the way, like there's a lot of like cultural things that have, are happening. And I don't know if you observe this more intact tech or is tech more like that, where you have, you know, a lot of just like constant firefighting and things coming through and people don't get time for strategic thinking. Like you're saying where the leaders are firefighting all the time. And it's so important for us to have like alone time just thinking about something.

I, you know, I, I was coaching, I had a product once who was at a larger company and he told me, you know, I, I do all my work in night, like after 10 o'. Clock. And I was like, why? He's like, well, you know, in the day I'm in all these meetings, you know, meetings, meetings, meetings. And people always talk about meetings like it's this invisible force that they can't control. And I was like, aren't you the head of product? And he was like, well, yeah. So I was like, so all these meetings, how many? If you told me your CEO wants to talk to you 20 hours a day, that would be one thing, But I was like, how many of these meetings come from your calendar? So.