Shaan flies solo to share nine unorthodox leadership frameworks he’s developed or borrowed from sources like Dr. House, Elon Musk’s Tesla Master Plan, and his wife’s consulting toolkit. The frameworks span team motivation, risk identification, calendar auditing, and project kickoffs — all practical, none from a business school textbook.
Speakers: Shaan Puri (host)
Intro: Nine Unorthodox Leadership Frameworks [00:00:00]
Shaan: What’s up, y’all. Shaan here. Sam is in Europe traveling around with the fam, so I’m on my own today and I wanted to do something cool. I think I got a great idea.
Shaan: Here’s my guess — I think this pod is going to be one that people really, really like, because I know I would have wanted to hear this at some point in time. The reason why is because most of the people who listen to this podcast are some form of leadership, right? You might have started your own company or your own business, you might be kind of an exec somewhere or a manager somewhere, or you want to be a leader. Most people who don’t want to be leaders are not listening to a podcast like this.
Shaan: So the problem is me and everybody else sucks. You know, everybody sucks the first time they are managing people. And this isn’t like “how to manage people 101” — there are a lot of books written about this, there are some best practices, there’s common sense. But I wanted to share some of the unorthodox, some of the weird things that I do that I have found work for me. They might not work for everybody, but they work for me. And not all of these will work for you, but again, they all work for me. I couldn’t find any of this stuff in a book. I heard about these either from somebody or I just kind of made it up on my own.
Shaan: So I think I have five, maybe six different things that I do that are unorthodox but work. Okay, let me start with number one.
Framework 1: The Dr. House Screenshot Technique [00:02:30]
Shaan: Number one is called the Dr. House technique — it’s inspired by Dr. House. If anybody watches the TV show House, he always does this thing. The show is: there’s this genius doctor, but he’s kind of like a curmudgeon. All the other doctors really respect him because he’s amazing, but he’s kind of hard to work with.
Shaan: One of the things he does that’s amazing — but hard to work with — is he has these three junior doctors who work under him. When a patient comes in and they run a test to try to figure out what’s wrong with the person, he doesn’t just look at it and say “here’s what’s wrong with the person.” First of all, it’s usually not that straightforward. Second of all, even if he kind of has an idea, he doesn’t spoon-feed it to his team.
Shaan: Instead, he will usually slap the scan, or the data, or the x-ray, or whatever, up on a screen and he’ll say “what do you see here?” Or he’ll say “what’s weird about this?” Or “what’s interesting about this?” And then the team has to start thinking and getting curious and looking at the thing — what do I see?
Shaan: This is really effective. I do this all the time. I will take, let’s say, some data I’m looking at, something that makes me go “hmm.” What I used to do is just share that with the team: “Hey guys, here’s what I found. Look at this data — this data shows that A is B and C.” I would give them a conclusion. I’m basically spoon-feeding them an answer. They’d read it, they’d say “yeah, that makes sense,” and then they would go on with their day — because they didn’t have to struggle to understand it, they didn’t have to be curious enough to go find it. They just got spoon-fed an answer and they say “yeah, I’m not surprised by that,” and move on.
Shaan: So I do it the other way now, which does three things.
Shaan: One, it trains the team to be curious and clever — because you’re not just giving them the answer. I’m not telling you to go do ten more analyses. I’m saying there’s something in this, what is it? It’s a little bit of a riddle.
Shaan: Two, it’s not a gotcha. I’m genuinely asking, because they will see things that you don’t see. So even if you saw one interesting thing, they might find two others that you didn’t really appreciate.
Shaan: And the last thing is it trains everybody, because maybe one person out of the group will see the interesting thing, but the other four will say “why didn’t I see that?” And that trial and error, that guess-and-check, is how people get better at stuff. So you’ll train a team of curious, clever people who get good at finding insights in data.
Shaan: That’s the Dr. House technique. I recommend you try it rather than spoon-feeding your team answers.
Framework 2: The Holiday Party Exercise [00:07:00]
Shaan: Number two I learned from my wife. My wife was a consultant, and she used to go into companies — it was always like “getting alignment.” She would go into a board meeting of, like, Yahoo’s board meeting. You’d have ten executives at Yahoo and they cannot — they all think they’re on the same page, and then only when you ask them certain questions do you realize that everybody has a different game plan, a different vision of what we’re trying to do.
Shaan: So she got good at sussing that out. But people are a little bit limited when you just ask them very literal, logical questions that tap into only the analytical part of their brain. If you say “what are our three key objectives for the year?” it sort of feels like they’re taking a math test.
Shaan: So she does this thing called the Holiday Party. The holiday party tactic: she had me go to a whiteboard and she goes, “all right, let’s fast forward — it’s Christmas Eve of this year and we’re at the company holiday party. I want you to start drawing what’s at the company holiday party.” I’m like, “what do you mean?” She’s like, “just draw things that would make it an awesome company holiday party.”
Shaan: So all of a sudden I’m having kind of fun, I’m being creative, I’m drawing, I’m just thinking of cool things that could be at a party. My guard is down. I’ll draw a DJ booth — we kind of laugh because my drawing is bad — and I’ll draw the next thing. And then she’ll say, “okay, what’s on the screen? What are you celebrating?” And that question — “what are we celebrating?” — is like “what are we trying to do this year?” What’s the milestone that we hit?
Shaan: And instead of saying “what are we trying to do,” it’s assuming it’s already done — that we’re already celebrating, we’re popping bottles because we hit one million users or ten million downloads or a hundred million in revenue, whatever it is. That screen can only have one big thing on it that we’re all cheering our glass to. So what is that north star metric?
Shaan: Then she would say, “cool, let’s walk around — who’s at this party?” And as she unfolded this party, first it got me in the mood for winning, because I’m already working backwards from the assumption that we’ve won. Then I identify the north star goal. And then after we do that little game — it only takes two minutes — we would say, “all right, so how are we going to get there? What would be the things we would need to do now so that that party happens?” And all of a sudden we’re talking and brainstorming from a place of certainty and confidence rather than fear and doubt about not being able to pull it off.
Shaan: When you’re in fight-or-flight, your brain only works in a very limited capacity compared to when you are at ease, relaxed. That’s why great ideas come to you in the shower — you’re relaxed, you have warm water pouring on your head, and your brain kind of melts away and can start to put together different data points that aren’t there when you’re tense.
Shaan: So I love this tactic — the holiday party drawing game. It really loosens people up, it gets them thinking, it focuses them on the north star goal. And then when you make a plan after that, they go into that plan from a state of mind of “we already won.”
Framework 3: The Beer Post-Mortem [00:13:00]
Shaan: Okay, here’s the opposite. This is called the Misery Loves Company tactic.
Shaan: Whenever you’re making a plan, at the beginning everything seems achievable, everyone’s optimistic, and it’s hard to identify the risks. It’s one thing to ask somebody “what are the key risks in this?” — but people get a little defensive, they use only the logical part of their brain.
Shaan: So a better question is this: let’s say you go do this, I go do my thing, we get busy, and six months or twelve months from now we catch back up. We’re getting a beer at the local pub, it’s four in the afternoon. And we say, “man, that idea was so cool. Let’s assume it went wrong.” Man, that idea was so cool, I can’t believe it didn’t work out — now what happened? What is the most likely reason we would give that things went south?
Shaan: This is a way to identify the core risk, the chief assumption, the riskiest proposition in your plan — to sort of work backwards from: we’re getting a beer, it’s already failed, and we say “man, that thing had so much potential. What went wrong? What do you think is the number one reason it might go wrong?”
Shaan: And then because you’re identifying that up front, you can now game-plan around that.
Framework 4: F, Marry, Kill for Your Team and Projects [00:17:00]
Shaan: Here’s another one. I find that people get very defensive about the status quo — especially leaders, because as a leader you’re responsible for the way the company works. If I said “did you hire too many people?” most people don’t want to say yes. And the reality is, I don’t know, 20-30-40 percent of the time the answer truly is yes — you’ve hired too many people. But if you ask CEOs, they’ll rarely ever say yes.
Shaan: In the same way, if you say “are you working on a bunch of useless stuff?” they’d say, “no, I mean, these are all important, they’re all valuable.” So people get defensive about their current plan.
Shaan: So how do you get people to identify the fat in their plan — to trim the fat — without the pressure and stress of them feeling like they’re wrong, or they’re being blamed, or they’re going to have to make some tough decisions? Because of that pressure, they just want to avoid it.
Shaan: So here’s what I do. We play a game. It’s sort of like that F, Marry, Kill game, right? Where you decide — out of these three choices — who would you marry, who would you kill? Let’s just focus on the kill part.
Shaan: I could sit down with any manager in my company and say, “In your team — I know you love your team, and I know they’re all great in their own ways — but if you had to do it, who would be the three people that you would cut? If you had to cut three, who would they be?” Similarly: out of all the projects and initiatives you’re doing, what are the three that you would cut if you had to cut three? Which ones would go?
Shaan: You could do this with anything. Customers — of all your clients on the roster, who are the three that you would cut, where the juice is not worth the squeeze?
Shaan: And if you can create a safe space where somebody can freely identify what they would cut — “don’t worry, we’re not asking you to cut anything right now” — and you do it yourself, you’re not just asking others. You do it yourself and think aloud. Maybe do it as a group: what projects would we cut? Which team members are at the bottom? There certainly is a top and a bottom — who is that? Which customers are in the top and the bottom?
Shaan: If you can identify those, it plants a seed. Once people have said it out loud, they’ve heard a truth. It’s very hard to unsee a truth. And it might be a month later, or two months later, or three months later — but eventually they will decide to trim some of the fat, either on their team, their projects, or their client list. And that will help the team grow.
Shaan: So that’s the F, Marry, Kill tactic.
Framework 5: The Superpower Presentation [00:24:00]
Shaan: Okay, I think I’ve done four tactics. Let’s do another one. This is the Superpower one — this is a way to build people up.
Shaan: I did this at my last startup and people really resonated with it. I made a presentation about each person on the team. I did this on a Friday afternoon — I said, “hey guys, let’s go do a little happy hour, I got a presentation for you.”
Shaan: I said, “you know, I’ve learned that in any team you can look for two types of people. You can look for people who lack weaknesses — meaning they’re pretty well-rounded, they have no fatal flaws, but they may not be great at anything. They’re at least good at everything. Or you can have people who are amazing at some things and kind of weak in other areas. And I’ve learned that the best performing teams are filled with people who are amazing in at least one area. So you’re hiring for an extreme strength, not a lack of weakness.”
Shaan: That’s an Andreessen Horowitz framework that I really loved.
Shaan: And I said, “the funny thing is, for most people, they’re not even aware of what their extreme strength is — because you’re too close to it. It’s so normal for you to be great at it, you don’t even realize you’re great at it. At some point, it’s other people who point it out. So I’d like to point out the superpower that I’ve seen each of you have.”
Shaan: Then I put each person’s face on a slide. So for example: “Hey, this is Derek. Derek’s our designer. Derek, what I’ve noticed is your superpower — and I don’t know if you’re aware of this — is that most designers I’ve worked with are creative types, they’re kind of messy desk, procrastinator types. They pull all-nighters when they get creative inspiration and they do amazing work sometimes, and other times they get stuck with sort of a creative writer’s block. Derek, your superpower is that you’re a great designer, but you’re like the mailman. You deliver every day at the same time. I give you the brief, I scribble a poorly written address of where I’m trying to get this package, and you’re able to interpret it like a mailman and say, ‘oh, I know where this is trying to go.’ And then you deliver it every day at five PM before you leave. You don’t work on the weekends — I know you’re not the type of guy I should be hitting up for that crazy weekend project. So you’re like the mailman. You deliver every day of the week except Sundays.”
Shaan: So I gave him basically a superpower — you have this amazing ability to consistently take a loose set of instructions and deliver on it — and I gave him a nickname that goes with it. That’s why I call you the Mailman. Then I moved to the next person.
Shaan: “Oh, this is Furkan. Furkan is not going to win any awards for being the most eloquent speaker or the most politically polished guy. But man, when you talk to Furkan, it’s almost like he’s allergic to BS. You know how someone who’s allergic to peanuts — you can’t even have a peanut dish near them, you feel uncomfortable taking peanuts around them because you might kill them? That’s what it’s like when I bring a half-baked plan around you. I don’t even feel comfortable saying it around you, because you’re so good at seeing through it — you’ll say ‘that doesn’t make sense’ or ‘wait, I thought you said this other thing, so how could both of those be true?’ That’s your superpower. You’re allergic to BS, you just can’t stand it. And because of that, it makes the rest of us up our game. We don’t bring half-baked or incongruent, illogical plans to you, because you’ll sniff it out in a second.”
Shaan: The beautiful thing is these things are both true and aspirational — they are this way already, but by giving it a superpower label, they then want to live up to that identity you’ve given them. So you can kind of architect the type of team you want by calling out areas they’re good in. They may not be doing it all the time, but by giving them their superpower, they will start to do it more often.
Shaan: So that’s the Superpower technique.
Framework 6: The Tesla Master Plan [00:33:00]
Shaan: Okay, I’m going to give you three quick ones.
Shaan: Number six is the Tesla Master Plan. If you’ve never read it — Elon Musk wrote a master plan for Tesla back when it started. He wrote Master Plan v1 like ten years ago, and then he wrote v2. I’ve handwritten his master plan many times, and then wrote my own plan for my own business after writing his.
Shaan: His plan basically says: Tesla’s job is to accelerate society’s move off of fossil fuels onto sustainable energy. To do that, we need to create a car that’s high performance and high efficiency. So we’re going to start with the Roadster — the expensive car — then we’re going to make the next car, then we’re going to make the mass-market Model 3. In summary, here’s the master plan: build an expensive car to build the brand, build a less expensive car to get more people on it, then use the economies of scale and learnings from production to build a mass-market car that gets to everybody.
Shaan: It is very powerful if you can write the master plan for your company. It doesn’t have to be right — it’s you putting it out there. What are we here to do? How do we plan to do it? And if you look at his writing style, it’s a very empowering style.
Shaan: I like to take his master plan and then write my own.
Framework 7: The Calendar Audit [00:36:00]
Shaan: Number seven comes from a CEO coach — Matt Mochary, or something like that. He has this technique called the Calendar Audit, which is very simple.
Shaan: Imagine you print out your calendar from the last week and you look at every meeting that was scheduled, every block of time that you used. You take three highlighters. Green means: that was something I enjoyed, that gave me energy. Red means: these are the soul-crushing, energy-draining things that I dread — parts of my day I don’t look forward to. And yellow is neutral.
Shaan: You look at that, and then you say: “Okay, this is an audit. I now need to take these red things and figure out, over time, how I’m going to get more green than red. How am I going to phase all the red away and get to only green?” That might be hiring somebody who likes doing that thing — because what’s red for you might be green for them. Or just getting rid of it, or minimizing the time you do it: “Do we really need three meetings for this? Could we not just do it in one? Could this meeting be an email?”
Shaan: So a calendar audit is a very valuable technique.
Framework 8: Peer Groups [00:39:30]
Shaan: Okay, so far we’ve had: number one, the Dr. House screenshot technique. Number two, my wife’s holiday party — work backwards from the celebration. Number three, the beer post-mortem — “man it’s a bummer that thing failed, why did it fail?” Number four, creating a safe space for the F, Marry, Kill game — who would you double down on, who would you cut? Three is just a magic number — it might be 3,000 for you, the number doesn’t really matter, same idea. What’s the bottom 20 percent of things, what’s the top 20 percent? Number five, tell each person their superpower and give it to your team as a presentation — they will live up to that reputation. Number six, the Tesla Master Plan. Number seven, the Calendar Audit.
Shaan: Okay, I’m going to do two more.
Shaan: Number eight is peer groups. Anytime I have an objective — let’s say I want to become a great poker player, or I want to get to 100,000 Twitter followers, or I want to build a DTC brand that does 50 million dollars a year — I will create a text chat group of five other people who are in the same kind of ballpark as me in terms of where they’re at now, and have that same ambition as their top ambition.
Shaan: Mentors and advisors: overrated. Peer group: underrated.
Shaan: So that’s what I would do. I would start by texting them, and then I would do like a once-a-month call where we could spend three hours on the phone or in person hanging out, sharing tactics and strategies, what’s working for them, and trying to achieve our mutually shared goal.
Framework 9: The Kickoff Document [00:43:00]
Shaan: Okay, last one is the kickoff document — this is number nine.
Shaan: A kickoff document is a template that I use before I start any project, because I believe that clarity is power. Too often people go into doing something without actually being clear on: what are we trying to do here, why are we trying to do it, how will we measure success, and what’s the first thing we should really do? That’s what a kickoff document does.
Shaan: The kickoff doc has three sections.
Shaan: The first is: what are we trying to do? One-liner.
Shaan: The next is: what does a win look like? And I define a win in two ways. What’s the floor of this win — meaning what is the minimum I would consider a successful, good outcome? Something achievable. And then what’s the “f*** yeah” win — the result that would make me say “f*** yeah, that really worked.” So now I get a range: a floor goal and a stretch goal.
Shaan: Then I also do an anti-goal — meaning what are some traps I could fall into along the way that would make me feel bad at the end of it, even if I hit my goals? Like, you know, I would love to be successful but I don’t want to screw over people along the way and carry that guilt with me. Being successful financially is the goal — but your anti-goal would be: I don’t want to do this in a way that makes me feel unethical or ashamed of what I did. I’d like to feel proud of it. Or: I’d like to be successful but I want to make sure I’m home with my kids every day at five — so my anti-goal would be never getting home before that.
Shaan: It’s important to identify your anti-goals. They’re very clarifying.
Shaan: And then the kickoff doc ends with your power hour. Basically: what’s something I could do in the next hour that would create momentum and get me to a win? This is not like “do some research” or “make a list.” It’s: get momentum toward the actual outcome. If I want to increase sales, that’s like — make a sale. Make one sale. Or if I want to grow my email list, that’s like: post a thread on Twitter in the next hour that will get some subscribers to my list. Just something to get the ball rolling that’s action-oriented so you’re not always in planning mode.
Wrap-Up [00:49:00]
Shaan: So those are nine different little tips and tricks that really work for me, that I don’t think you’ll learn in business school or at your job. Even when people try to do management training, it’s usually not things like this. These are my kind of unorthodox pet tricks that I like to do that help me with my companies.
Shaan: I hope that’s helpful for you. If it is, let me know — you can tweet at me at ShaaanVP. If it’s not helpful, tweet at me saying “hey, that wasn’t helpful” — honest feedback, I love honest feedback. Either way works for me. I’m at ShaaanVP — S-H-A-A-N-V-P — on Twitter. All right.