This week on First Round Review, we hold three conventional engineering management “anti-patterns” up to the light for a closer look.

Unexpected Anti-Patterns for Engineering Leaders  — Lessons From Stripe, Uber & Carta

When Will Larson was CTO at Calm, he had to make the tough call to cancel a major product migration from the monolith to a multi-product suite. It ended up being a huge success for the company, so when he first got to Carta, also in the CTO’s seat, he had the instinct to try the exact same thing.

“I thought, if it worked at Calm, why wouldn’t it work here?” Larson says.

What he discovered later was that he was missing crucial historical context and different perspectives, things he only found out after getting obsessively close to the details on his team.

While conventional management wisdom told him, as a leader, to step away from the code, it was the dozens of conversations and days spent mining for context that clued him into all the reasons his strategy at Calm never would have worked at Carta.

“One of the biggest lessons in management over the last decade is that micromanagement is bad,” he says. “But I think this is an anti-pattern. Avoiding micromanagement creates disengaged and context-free leadership, and leadership can be so much more than that.”

Larson has always been drawn to the puzzle that is engineering strategy. His winding career has landed him in leadership roles at Stripe, Uber and Digg — and he’s scaled engineering teams from tens to hundreds of people. He’s meticulously documented the lessons he’s learned, penning widely-circulated essays on the topic on his blog, authoring three different books and even sharing some of his frameworks right here on the Review.

He returns today to drop more knowledge, this time focusing on conventional leadership practices that lead folks astray. “We have to have the openness to think through whether a different approach might make sense in a very specific case,” he says. “That’s a fundamental part of engineering.”

In this exclusive interview, Larson walks through three unexpected anti-patterns engineering leaders can use to elevate their team strategy. He lays out the case for why micromanaging can be a good thing, why execs shouldn’t bother spending too much time on metrics, and why managers shouldn’t shield their direct reports from reality.

While he speaks directly to an audience of engineering leaders, his advice goes far beyond that, and executives in any function are sure to find his advice useful.

Here’s a quick snippet of what’s inside:

• Don’t shy away from micromanagement: “New engineering managers are often advised to ‘step away from the code.’ But an extremely high-functioning exec understands the domain they are operating in at some level of detail,” he says. “As you get too far out of the details, you just become a bureaucrat. Too many well-meaning engineering managers end up as bureaucrats.”
• Measure imperfectly: “Often when people start measuring, there's always a concern that their measurement is flawed. And that's true for all functions,” he says. “But I’m a believer in measuring something imperfect, but useful, versus holding out for the perfect metric while measuring nothing in the interim.”
• Don’t be an umbrella: “In the past, I used to think I was energizing my team by sparing them the details. But now it feels like lying to them,” he says. On a tactical level, Larson adjusted this habit by buffering less information. “That means even if it’s disappointing for folks, I’d rather them process news bit by bit, rather than deal with a huge ocean of mess all in one moment.”

Thanks, as always, for reading and sharing!

-The Review Editors

P.S. If you’re hungry for more of Larson’s best leadership practices for eng teams, go deeper by listening to our podcast episode with him here.

Recommended resources:

-Will Larson’s latest blog post on making engineering strategies more readable.

-CTO and career coach Yue Zhao on what we get wrong about influence.

-This deep dive examines the growing specialization of product management.

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This week, we're marking the last day you can apply to PMF Method by sharing an extra dose of encouragement, with 20 lessons from 20 different founders on tackling the winding journey to product-market fit.

20 Lessons From 20 Different Paths to Product-Market Fit — Advice for Founders, From Founders

For more than a year and a half now, we’ve been privileged to showcase dozens of remarkable founders in our Paths to Product-Market Fit series, a wide-ranging public study into how all sorts of different companies have tackled the journey to product-market fit.

Importantly, our goal has been to skip over the glamorous, up-and-to-the-right talking points to find out what really happened behind the scenes.

That’s why we’ve told the real stories of false starts and pivots, like how Plaid started out as a consumer budgeting app, how Lattice was focused on OKRs before shifting to performance management, and how Shippo’s founders were originally building an e-commerce site. We shared vivid and detailed anecdotes, like how Vanta cycled through different company ideas, how furiously coding on a train ride convinced Ironclad to change its category, and how Webflow almost sputtered out after a splashy launch on Hacker News.

But ever hoping to be equal parts inspiring and practical, we’ve also dug into the tactical nuts and bolts — from how Gong excelled at leveraging design partners and how Material Security pressure tested different ideas, to how Retool refined its ICP and Airtable took two slow years to launch its beta.

We thought it was well worth revisiting some of the biggest lessons that have stuck with us — so we plucked out our favorite bits of advice from each story in the series so far.

The advice that follows touches on all sorts of different mile markers along the PMF journey, from coming up with the idea and validating it, to talking to customers, building the initial product, and figuring out your market and messaging.

Our goal is that you can find a dose of inspiration, the antidote to a particularly thorny 0-1 problem you’re facing, or a fresh perspective to reframe your thinking.

Thanks, from all of us at First Round, for reading and sharing.

-The Review Editors

P.S. — We’ve also included several videos of the interviews throughout, in case you prefer to hear your company building advice straight from the founder’s mouth (and plenty of the series’ popular timeline graphics, in case you prefer the continuum format).

P.P.S. — If you’re looking to dive even further into what it takes to find product-market fit, check out our new framework, The 4 Levels of Product-Market Fit. You can also apply to join PMF Method by today, May 7 at 11:59 PDT to get help uncovering what customers really need, building the right V1 product, and closing your first commercial contracts.

Recommended resources:

-Review favorites Tara Seshan and Brie Wolfson have started a new podcast, Red Queen, where they tell the stories of the invention and reinvention of the world's most innovative companies.

-Our very own Annie Duke stopped by another Review favorite podcast to chat all things decision-making with the one and only Lenny.

-What Every’s Dan Shipper learned from spending 24 with Github’s Copilot Workspaces product.

How to Know if Your Idea’s the Right One — A Founder’s Guide for Successful Early-Stage Customer Discovery

How do you go from a pie-in-the-sky idea to a fully-fledged product? Some founders start building right away, spinning up a (slightly shoddy) MVP for folks to react to, then iterating from there. Others take a deep-diving approach to research, setting up dozens (or even hundreds) of calls with folks to validate the idea before writing a line of code.

As a user research expert, you might expect Jeanette Mellinger to be in favor of the latter approach — but you’d be wrong.

Sure, she’s a big proponent of user research interviews as a form of validating your idea. But this slapdash mentality of trying to speak to as many folks as possible is where she finds that many well-meaning founders go astray.

In addition to her role as BetterUp’s Head of UXR, Mellinger also works closely with early-stage startup founders as First Round’s User Research Expert in Residence. To these folks, she preaches the mentality that less is more. You can glean more qualitative data points and patterns from five deep conversations than from 50 unfocused ones.

“We get nervous when we hear, ‘Oh gosh, I only spoke with five people.’ But that’s my user research magic number. If you bring that focus into it, you can get something that’s much deeper than you’d ever expect,” she says.

On the Review, we unpack her ultra-approachable three-step guide to bring more structure to early customer discovery and idea validation. Along the way, she shares plenty of low-lift tactics to ensure your approach is rigorous, but not onerous.

• Step 1: Make a Plan. “It’s so tempting to want to ask about 10 things at once, but that’s only going to yield shallow, inch-deep responses. This is your opportunity to go deep. What are the one or two things you must learn now?”
• Step 2: Learn without letting bias creep in. “Let’s say you start to hear something that sounds really good. That’s your alarm right there. The moment you hear, ‘Oh yeah, this product is great,’ that’s a sign to ask the counter. What is something you can push on here?”
• Step 3: Find the right patterns. “So often teams will want to jump right into solutioning and action mode. But the more you ground yourself in the data, the more conviction you’ll have in your idea.”

Thanks, as always, for reading and sharing!

-The Review Editors

Recommended resources:

-We’re looking for a go-to-market manager in SF or NYC to help founders get their first million in revenue, faster.

-Want to know how your go-to-market motion stacks up to the best? The 2023 Product-Led Sales Benchmark Report is out now!

-Shreyas Doshi is hosting a product leadership masterclass seminar on March 23rd.

-This video with books every entrepreneur should read.

-How to escalate a problem the right way.

Trending this week — Review Reads:

GOAT’s Path to Product-Market Fit — How a Fake Sneaker Sparked a $4B Idea

GOAT co-founder and CEO Eddy Lu sits down with First Round Partner Todd Jackson to tell the story of how a decade of middling entrepreneurial ideas finally culminated in the $4B idea for a sneaker marketplace.

First Round ReviewFirst Round Staff

From Flagship Back to Fledgling: Lessons on Going Multi-Product From an Early Stripe PM

In this exclusive interview, Tara Seshan shares nine lessons from her playbooks for going multi-product, drawing on examples from both Stripe and Watershed.

First Round ReviewFirst Round Staff

‘Get in the Van’ and Other Tips for Getting Meaningful Customer Feedback

Michael Sippey has been building tech products for over 20 years. His most valuable ideas, though? They came from speaking with customers. Here’s how.

First Round ReviewFirst Round Staff

The Tactical Guide to Making Better Decisions When Starting and Scaling Companies

The First Round team has been lucky to work with retired poker player and decision-making expert Annie Duke in a special capacity these past few years. Here, we open-source some of the advice she gives to help founders face down uncertainty and make better decisions.

First Round ReviewFirst Round Staff

GOAT’s Path to Product-Market Fit — How a Fake Sneaker Sparked a $4B Idea

We’ve covered lots of different founder paths here on the Review. But none may be as curious and meandering as Eddy Lu’s.

Today, he’s the co-founder and CEO of GOAT, a global platform for sneakers and luxury apparel that boasts over 350 brands, a million sellers, and 50 million members across 170 countries — valued at over $4B.

But page the calendar back, and you’ll find a decade’s worth of entrepreneurial endeavors with very little in common. After teaming up with his co-founder, Daishin Sugano, the two tried their hand at owning a cream puffs franchise, hopping aboard the early iPhone app train, and even had a YC stint trying to build a community platform for social dining.

Then, a twist of fate (coming in the form of a pair of fraudulent sneakers) sent the pair down an entirely new rabbit hole.

In the latest installment of our Paths to Product-Market Fit series, Lu shares the inside story of all the unexpected twists and turns in GOAT’s founding story — and it certainly wasn’t smooth sailing once the founders landed on their winning idea. Black Friday deals gone awry, website crashes and unpopular features are just a few of the obstacles that would come to pass.

Along the way, Lu shares his biggest pieces of PMF advice for others to lean on — and how to stay gritty and hungry amidst mounting pressure.

Thanks, as always, for reading and sharing!

-The Review Editors

Recommended resources:

High signal-to-noise interview questions.

Stripe’s former COO Claire Hughes Johnson is on the Tim Ferris Show.

Molly Graham on evaluating job fit.

Trending this week — Review Reads

From Flagship Back to Fledgling: Lessons on Going Multi-Product From an Early Stripe PM

In this exclusive interview, Tara Seshan shares nine lessons from her playbooks for going multi-product, drawing on examples from both Stripe and Watershed.

First Round ReviewFirst Round Staff

Add More Rigor to Your Reference Calls With These 25 Questions

When approached with craft and care, reference calls can be a massively influential piece of the hiring decision.

First Round ReviewFirst Round Staff

A Founder’s Guide to Assessing Strengths and Weaknesses

Psychologist and co-founder of Coa, Dr. Emily Anhalt, unpacks the five traits of high-impact founders — and how the very traits that make a founder successful can also hold them back.

First Round ReviewFirst Round Staff

Grit or Quit? Tactical Advice for Founders Facing Tough Decisions

Quitting is an underrated startup skill, says decision science expert, bestselling author, and former poker pro Annie Duke. She unpacks the psychology behind why it’s so hard to walk away, sharing tactical advice for all the forks in the road.

First Round ReviewFirst Round Staff

This week, we're diving into the how, what, when, and why of going from single product focus to multi-product strategy, a common stumbling block for startups.

🎧 Prefer to listen? Check out the audio version of today's interview here. 

From Flagship Back to Fledgling: Lessons on Going Multi-Product from an Early Stripe PM

Who is your target user?

For Tara Seshan, this is the lead-off question for her teams when she’s running product reviews, and it always makes her think of Enterprise — the car rental company.

“I’m not sure if it’s apocryphal or a real story, but I still like to tell it. Enterprise was competing with the likes of Hertz and Avis. Those guys had the airport real estate. They also had Audis and BMWs. Enterprise Rent-A-Car really had nothing. And so there was absolutely no way to compete building ‘the best service’ or ‘best product.’ What they did instead was focus on a different user — people who get into car accidents,” she says. So instead of focusing on providing fancy vehicles, Enterprise offered a unique crash pickup service.

Over time, they were able to expand. But it started by making a very, very opinionated bet on who their target user was and it allowed them to compete on dimensions that other services and tools just didn’t find relevant. It is the most important question to ask, full stop. If you cannot clearly outline to me who your target user is and, therefore, why the features follow are uniquely suited to that user, it’s dead in the water. It's got to be specific.”

In Seshan’s view, folks tend to overestimate the impact of launching specific features and building the best product, instead of focusing on building the right product for their target user. Sounds simple in theory, but tough to consistently pull off in practice, particularly as a scaling startup takes bold swings at building out its product lineup.

But she’s got an excellent track record here. Before her most recent role as Head of Product at Watershed, Seshan spent a nearly seven-year stretch at Stripe. She joined the company at the sub-200-person mark back in 2015. She was the PM on Radar, Stripe's first monetized product outside of core payments, and she helped scale Billing and Treasury from 0 to 1 as a product lead and GM.

Today on The Review, Seshan shares 9 specific lessons on going multi-product and building for your target users, drawing on examples from both Stripe and Watershed. She dives into:

• Advice on how to get the timing right and different ways to approach the problem of what to build
• The 12 questions she runs her teams through at every product review
• How to structure lean, self-sufficient teams that can navigate the uncertainties of new product development
• Tips for hiring great product thinkers and “diamonds in the rough,” including traits to look for and specific interview questions.
• What she learned from Patrick Collison and Shreyas Doshi at Stripe.

Thanks, as always, for reading and sharing!

-The Review Editors

Trending this week — Review Reads:

Add More Rigor to Your Reference Calls With These 25 Questions

When approached with craft and care, reference calls can be a massively influential piece of the hiring decision.

First Round ReviewFirst Round Staff

Vercel’s Path to Product-Market Fit — From Open-Source Project to Billion-Dollar Business

Guillermo Rauch, raised in Buenos Aires and fascinated by computers since age 7, taught himself to code and moved to San Francisco at 18. His company, Vercel — the frontend cloud service behind open-source development framework Next.js — was recently valued at $2.5 billion.

First Round ReviewFirst Round Staff

How to take bigger, bolder product bets

Seasoned product leader and Slack’s CPO Noah Desai Weiss shares the three-step framework he leans on to make quality product decisions with just the right amount of risk.

First Round ReviewFirst Round Staff

Build Products That Solve Real Problems With This Lightweight JTBD Framework

Drawing on her experiences building products at Lumosity, Oculus, and Facebook’s New Product Experimentation group, Sunita Mohanty shares a lightweight “jobs-to-be-done” framework for early-stage product teams, along with templates and go-to-market tactics.

First Round ReviewFirst Round Staff