First Contact // 
Product Management  

 
  

Disclaimer
This is all based on our past experience, the story here is fictional, and any resemblances are
purely coincidental. You, your mileage and your career will vary, but we can confidently say that
the concepts and experiences below have enabled us as PMs to succeed in high growth
companies building awesome stuff. This represents our individual views and in no way reflects
the views of our employers.

Logo credits - ​LogoJoy

 
  

Praise for First Contact - Product Management

"While relayed in a tongue-in-cheek, light hearted manner, this quick read gives new product
managers insight into common situations that PMs face. PMs can learn from Julian's missteps,
but his story ultimately tells us that it's ok to make some mistakes and find your path."

Lauren Chan Lee​, Senior Director of Product Management at Care.com

“The tale of the new PM. Humorous from the start, in First Impact, experienced PMs will enjoy
relating with Julian's early struggles and growth as a PM while aspiring and new product
managers get a glimpse of what’s in store for them and some important gems of advice I wish I
had as a new PM! Definitely an easy add to your product management reading list.”

Ana Sheila Victorino​, Co-founder and Director of Product for Bask

 
  

Table of contents
The chapters roughly follow the story of Julian, and the principles which will make Julian
successful as a PM. To all our readers, to all the Julians out there, hope you enjoy the read and
learn a little something for your jobs.

Preface - About the authors

Chapter 1​ - Starting your time as a PM (this is pre-day 1 at the new job)

- Get Hyped! New job is about to start. Funemployment is at an end
- What do you expect from your new job?
- What will make you stay / What will make you leave?

Chapter 2​ - Getting a lay of the land

- You are hired, now what?
- How do you navigate your surroundings
- What questions should you ask?

Chapter 3​ - What does Success look like

- All problems stem from mis-set expectations. Don’t fall into that trap
- What are some heuristics of success?
- If you are not sure of success, ask the right questions

Chapter 3​ - Execution as a PM
- PM as an operational model
- Core expectations from execution
- Successes in execution

Chapter 4​ - Your day to day as a PM - Tactics

- Getting into the tactics of PM-ing
- Tactics - Execution, Team alignment, Data driven decision making
- Great resources to look at for tactics

Chapter 5​ - Your day to day as a PM - Strategy

- Getting into the strategy of the business and the product - what is your north star?
- Strategy - Product Performance, Culture of improvement, user focused problem solving
- Great resources to look at for strategy reads

 
  

 
Chapter 6​ - What does career progression look like?
- What are predefined career paths? (hint: there is none)
- What do you know now that you didn’t before?
- How do you take control of your own career?

Chapter 7​ - Intellectual honesty and retrospectives

- Are you happy?
- What appeals to you and how has it changed?
- Building bridges and setting up walls

 
  

About the authors

Clement Kao

Clement Kao is a Product Manager at ​Blend​, a San Francisco-based startup that partners with
banks, lenders, and independent originators to reimagine the mortgage borrowing experience.

Clement is also the Product Manager-in-Residence at ​Product Manager HQ​ (PMHQ), where he
has published 50+ product management best practice articles, provides advice within the ​PMHQ
Slack community​ (6,300+ members), and curates the weekly PMHQ newsletter (22,000+
subscribers).

Drop Clement a note on ​LinkedIn​, he loves to help!

 
  

Megh Gautam

A seasoned Enterprise Product Manager with software engineering experience before

transitioning to Product full time. Based out of SF, he’s worked at ​Hearsay Systems​ for the past
4 years. Prior experiences include managing financial technology products at ​Bancbox (nee
Finxera)​ and massively distributed data systems at ​Pivotal (Greenplum)​. Software experience
comes from Microsoft. Foundational PM skills were inculcated at Stanford in their Management
Science & Engineering program.

Megh’s areas of expertise center are in regulated markets, distribution of net new products and
operationalizing data in building products. He loves leading a diverse cross functional team
including but not limited to engineers, designers, data folk and other PMs.

Say hi on ​LinkedIn​!

 
  

Ch 1 - Starting your time as a PM

Julian is starting his PM career in a new company. An ace student that volunteered for all things
entrepreneurial in college, he was a hard charging student, sharp as a tack. He took an interest
in talks, seminars that were at least a year or so more advanced than his workload. He could be
counted on in a group project even though the slackers would get chewed out by him at a later
date.

Like everyone from the age of 12 and up, he wanted to be an entrepreneur. He had big dreams
and spent most of his time listening to other storied entrepreneurs. He took a gap semester,
tried to get a company off the ground. He hoped it would be as glamorous as the folks described
to him. “Be the CEO,” they said. “Have control over strategy,” they said. Turns out that the
reality is different from the ground level than it is from on stage with a microphone attached to
you.

“Watch me do Strategy” // Credits to Bird box @ Netflix

Julian realized that without actually understanding what sales and marketing does, he couldn’t
run sales and marketing. Soon enough, those realizations drifted into product, engineering, biz
dev, finance, ops, recruiting. Fortunately HR didn’t need to be part of this whole equation
because by the time he realized he wasn’t cut out for a startup gig, his startup was… how do I
put it mildly....dead. The T-shirts that he printed for career fair still languish in his dorm. He once
debated getting a tattoo to commemorate his failed startup, but decided that an Amazon Prime
box of T-shirts was memory enough.

He was now fully focused on being a Product Manager. He would put his entrepreneurial
journey on hold to take the time and be yelled at by both engineering teams and sales teams.

 
  

 
He felt that the cross-functional, interdisciplinary goodness of PM-ing would set him up for a
great run as a founder someday. He would actually understand how functions like sales,
marketing, and others worked. He could build a great product that he was proud of. It all made
sense. Product Manager Life chooses us, we don’t choose to become a PM.

Product Managers are a unique blend. As far as individual contributors, they are often the
hardest roles to fill. Your recruiters will agree. PMs are all different and depending on what
companies already have, their needs are constantly evolving.

Right before he started, Julian was understandably nervous. First days and all that. He had
some idea what he wanted to do and some idea of his new coworkers. It was mostly made up in
his head with a grand total of one hour of interview interaction. People on their best behaviors
are rarely what they are like all the time.

So Julian did the responsible thing. He went back to his time as an interviewee and looked
through why he was interested in the first place. He read through the job description and slowly
but surely got hyped! He got the role he wanted, at a place where he felt he’d learn quickly.
Julian went to sleep hyped and he decided that he was going to be enthusiastic about his first
day, no matter what.

WOOOOOO // Credits - ​SBNation

 
  

 
Pro tip - be like Julian. Enthusiasm matters, and a little enthusiasm goes a long way. Of course,
don’t be an over-caffeinated Ric Flair type because you don’t want to go around going
“whooooooo!” in your new office.

Visualizing a great first day in your new role is a good starting point. ​Perception is reality​, so if
you start with enthusiasm, then you will come off as an enthusiastic member of the new
workforce. And everyone loves enthusiasm, it makes up for a lot of shortcomings.

The next day, at his first day of work, here are things that Julian did which you should consider
doing as well -

1. He was fully present in his meetings, he didn’t check his phone compulsively
2. He was prompt and on time for all his meetings
3. He introduced himself to his neighbors, and was open and approachable
4. He didn’t pretend that he would single handedly solve all problems at the company by
diving into the technical nuances. He considered the big picture and talked to people.

Julian got back from his first day and he was tired. That’s totes normal. The new information you
absorb (including having to remember the last names of 4 different Adams who work at your
new gig) is time consuming and exhausting, especially if you’re an introvert.

But all in all, he had a good Day 1. Now it was over to making sure that he didn’t overdose on
the Kool-Aid. Sure, his new place wanted to change the world, and surely all companies that
want to change the world end up changing it right? Yeah, right. So Julian summoned his ​rational
system 2​ amidst the dopamine hit of making new friends via his new system 1. In other words,
he decided to consciously reflect on his first day and on his path ahead, rather than relying on
emotion and intuition alone.

Consider that every place may not be your terminal place. It is easy to get distracted and
comfortable. That is not a recipe for success. Remember what you came to learn and
aggressively spend time learning it.

Julian filled out his wishlist of skills that he wanted to acquire out of working at his new place. He
wrote down each specific skill that he thinks his new work will equip him for. And even if it is
100% wrong, it’s so important to reflect back in 6 months and get a check on what your own
expectations were. It’s a fascinating whirlwind and a great way to journal your own
development. Try it!

As you reflect, remember why you are joining in the first place. Places will usually fall into 2
categories: 1) ​stepping stones​ or 2) ​destinations​.

 
  

 
Some of us are lucky to count our destinations as our dream destinations. But before you get
ahead of yourself - don’t sabotage yourself! If you explicitly consider your destination as a
dream destination, you’ll put way too much expectation in your new job and things only go
downhill from there. You don’t need that kind of pressure. Julian didn’t do that at all. He views
most places he joins as stepping stones.

An intro email is less prep than this // Credits - Pexels

If a firm that you are joining is a stepping stone, then make sure that you proactively learn all
that you came to learn and build out your list of experiences. If you are on a timer from the day
you start, it will also help get a hustle on. If it is indeed a destination, remember to capitalize on
all the reasons why you liked it in the first place. This is the sweet spot for Julian.

Another word of wisdom - just because a place is a stepping stone doesn’t mean that you
should treat your colleagues poorly, or to take your responsibilities lightly. You’re still there to
fully own your job. Don’t be flaky, because your reputation will follow you!

Anyway, we digress. So, on a more tactical level - wherever you end up, you need to have an
intro email ready to roll. Everyone will ask for it and having it handy makes you some sort of
prophetic ninja of the occult. So, in this section, we’ll get you writing an intro. Here is a basic
template to follow:

Hi!

I am <Insert your name here>. I am excited to join in my role as <Whatever you are joining for>.
I have a passion for <something vaguely work related> so <Company name> is an ideal fit.

 
  

 
Outside of work I love <Something sane that is not arson related> and am a huge fan of <Sports
/ Arts / Theater>. Love to meet you all. I am sitting by <Insert unwitting landmark>. Come say hi!

Thanks!
<Insert name here>

----

Feel free to add your own twists and turns to it. You are trying to give enough away to sound
relatable. You are also trying to come off as business cat.

​ now your meme

Business Cat for reference // Credits - K

Skew too much to one side and people will think that they have inherited a frat house, too much
on another side and you come off like a robot.

In a Nutshell
● Be present, there isn’t a distraction that is worth it in your first few days
● Be enthusiastic, a little enthusiasm goes a long way
● Be prepared, its your work so understand your strengths and weaknesses

 
  

Ch 2 - Getting a lay of the land

After his first day on the job, Julian is now focused on getting a lay of the land. Julian’s unique
viewpoint is what really matters in his first week. After all, he has rich experiences as a student,
as a project leader in school, and as an entrepreneur. But, now he’s in the big leagues. People
actually depended on him from everything related to sales and servicing of the product.

Julian reflects in the bathroom. He struck his shoulders open and ​power posed​. He needed to
get done with it before he heard a new entrant or got interrupted by the flush. He needed all the
confidence he can get. Julian need not be afraid. He has a base, a foundation - things that
make him inherently valuable. The worst thing that Julian can do is to let the surroundings
intimidate him.

​ izmodo
In 3..2..1 // Credits - G

The Men In Black memory eraser acts quick in a new environment and you tend to forget what
you learnt before. That is a bad idea. The trick is to balance - remember what you learnt
passively and put them in active use in your new surroundings.

Don’t forget all the learnings that you went through to be a PM, it could be classes, could be
your prior job. In the case of Julian, it was that group project which he crushed but everyone

 
  

 
else was too hungover to notice. It was also his attempt at getting a V0 product off the ground
that miserably crashed and burnt but the power pose vanquishes such memories.

When Julian makes first contact with the organization, he had a goal to preserve his unique
viewpoint. Be it in cultural things like all hands or technical things like getting a handle on what
software he was supposed to use. This works to his advantage in almost all his future dealings.
He is now not just a new guy, he is also a guy with perspective and a unique viewpoint.

When you get into the first contact with the product, you will have insights and ideas that will
seem foreign to the organization. It is because a lot of the folk will have tunnel vision and it is up
to you to work against that tunnel vision and bring in a new perspective. In fact, your first contact
with the product is your white whale moment. The frustrations you have with your product is
your ​Moby Dick​ and you are Ahab. You will bury something so deep in your psyche that it will
take years of therapy to fully extract. And all the while that you work at that firm, you will want to
get rid of those frustrations that you encountered when you onboarded. Let that drive you. Let
that reality make you realize what you have become.

Or, you know, be like Julian and take great notes. It makes for a fun anniversary story. And,
most of all, Julian comes off as someone with a good product eye.

Julian got all his new hire stuff out of the way as quickly as he could. He wanted to make an
impact and he wanted to be valued. Getting bogged down in new hire proceedings is a surefire
way to not do that. All Julian wanted to make sure was that he was getting paid and his
insurance covered. No one really retains any more than that.

As a reminder, you are now entering the beginning stages of when you can pull out your “I am a
new hire” card. This is the beginning of a beautiful journey. You can basically pull this out to
figure out which open source version of Django your engineers are running to what the margins
were on that last deal. Use this well, figure out once and for all what the difference is between
ACV and ARR. Understand what your billable hour philosophy is. Poke around and see what
security standards are implemented in the org. The world is your oyster and because you are
new, all questions are good questions. The halo effect lasts for only a couple of months, so
don’t be shy in using it.

It’s key to attend every meeting you have been invited to for at least 2 weeks. If nothing else, it
familiarizes people which is key. People should see you as part of their team and not some
foreign pathogen type that will take an eternity to onboard. Ask at least one question per
meeting but don’t be an annoying oxygen suck because that's how your peers eyes will roll to
the back of their heads.

 
  

 
In a Nutshell
● Don’t be scared. You have every reason to be there, you belong there!
● Ask questions, there are no dumb questions but there are smart ones, err on the side of
smart ones
● Take notes, be analog and don’t get distracted by your computer / phone / laptop

 
  

Ch 3 - Execution as a Product Manager

Julian started tackling his day-to-day work with lots of gusto at first, in his quest to find success.

As a newly minted product manager, he spent hours and hours in writing user stories and
tickets. At first, he paid lots of attention in crafting them perfectly. After all, Julian is a competitive
person - he wants to look like a rockstar compared to the other product managers in his
organization.

But after about 6 weeks of writing user stories, Julian got bored. Even worse, not only was he
bored, he also never got any praise for writing awesome user stories.

So, Julian decided to stop putting so much detail into his tickets. Why bother? He figured that
since he talks to his team every day at stand up, there’s no need to be so detailed.

What he was really excited about strategy. After all, excellent strategy changes the world, right?

​ nsplash
Every good strategy looks like this, right? // Credits - U

 
  

So, Julian set aside 12 hours a day conducting competitive analysis. After all, Julian is a hustler.
He wants to know exactly what the competitive landscape is like, and how he can pull together a
strategy to crush all of his competition. Heck, he even spends his weekends doing competitive
analysis.

After 2 weeks of hustling, Julian has pulled together a gigantic dossier with screenshots,
diagrams, taglines, financials, and all sorts of other good stuff. So far so good, right?

Well… turns out, his development team noticed almost immediately.

His engineers can’t figure out what the cryptic ticket called “New Header” is, for example, since
Julian never added a description of what it’s supposed to do.

His designers can’t figure out what “Make it flashy” means… what element was supposed to be
flashy? And what defines flashy?

And his testers can’t figure out for the life of them whether “Fix double-click weirdness” was
actually fixed, because there were no acceptance criteria in the ticket.

At sprint retrospective, the entire team brings up that Julian’s lack of detail has caused them to
slow down.

Julian rolls his eyes and notes it down. “They’re just being overdramatic,” he thinks. “They don’t
understand - I’m not their janitor. I’m figuring out an amazing strategy, so I can 10x the company
and make my equity worth something. It’s their fault that they’re not paying attention when I give
directions at stand up.”

At the next sprint retrospective, the team brings up the same issue, this time with more anger.

Julian ignores them. He says, “I heard you last time. I have priorities. I’ll do it eventually.”

The very next week, Julian receives an email from his manager, Alana.

“We need to talk about your performance and attitude. I’ve scheduled a 30-minute walk on your
calendar.”

Julian is shocked. He’s always been the A+ student, and now it feels like he has detention. He
grimaces, and clicks “Accept” on the calendar invite.

 
  

 
Fast forward to their chat. On their walk, Alana asks Julian what’s going on. He started off so
well - so why are all of the tickets so poorly defined now?

Julian shrugs. “Meh. It’s just busywork. I already told the team about the tickets during stand up.
They should be taking notes, I don’t see why I need to spend time repeating myself. I’d much
rather spend time thinking about the strategy. By the way, I have a fantastic initiative that I want
to start tackling! We should change our distribution - ”

Alana cuts him off. “Stop. Product management isn’t fun and games - you need to be reliable
and you need to deliver. You don’t get to pick what you’d like to do. The team relies on you to
lead them, and that means being a servant leader.”

Julian stiffens. “What the hell is a servant leader? Leaders don’t serve. They disrupt and they
delegate. That’s how I made sure my final projects for my classes all got finished in time!”

Alana sighs. “You’re still young, and it’s clear you haven’t developed empathy for your
teammates yet. Imagine that you’re designer. Someone tells you to ‘fix the header’ without any
details. Then you craft a design based on your notes from your conversation together - you’ve
spent dozens of hours on the design. Then, they reject your design and tell you to do it again.
Then you try again, and they reject you again. How would you feel?”

Julian snorts. “If I were in that situation, I’d feel fine. It would be my fault for being a bad
designer.”

Alana shakes her head. “No. You’d be mad. In any case, let’s just make this brutally clear. By
next sprint, if I hear another complaint from the team about your lack of attention to tickets, I’m
firing you. I’m being especially hard on you because I’ve seen evidence that you’re good at this,
and I won’t hesitate to terminate a teammate who’s become toxic. Fix it.”

Julian burns with anger. Why does he have to do something as stupid as writing down ticket
details? Once he gets back to his desk, he pulls up all of his tickets and vents his anger against
his keyboard by typing as loud as humanly possible.

 
  

What his face looked like after his walk with Alana. // Credits - ​Unsplash

Over the next 3 days, his tickets become flawless again - filled with screenshots, detailed
instructions, user stories, and acceptance criteria.

At the next sprint retrospective, his team is noticeably silent about his tickets. No one raises a
complaint this time. Julian still fumes in the corner. Tickets are so boring…

But even though user stories felt painfully obvious to Julian, the fact is that his development
team didn’t have the opportunity or privilege of knowing the context of the user. Those user
stories mattered a lot.

Execution is table stakes for a product manager. When product managers have tasks, they are
expected to execute on them 100% of the time. Product managers need to deliver what they
commit to, and only commit to what they can deliver.

By making the sacrifice, Julian enabled his development team to be aligned, productive, and
empowered.

And, going back to strategy… strategy doesn’t matter without execution.

 
  

You can have the best strategy in the world, but if you can’t guide your team to pull off the
strategy, that strategy is worthless.

Even if Julian had successfully pitched his new distribution play - what then? Would his team
have been able to execute? No, because he himself did not execute on his commitments.

Product managers must execute. Otherwise, why not just hire external strategy consultants to
replace the role of the product manager?

Back to Julian. Once he finally got back on top of his user stories, he started noticing that his
team was really struggling with staying on top of what tickets they should be tackling. During
stand up, each person would list out fifteen tickets at a time. It got to the point where literally
everyone was bringing a notebook and would monologue for 5 minutes each to talk about all of
the work they were responsible for doing.

And the worst part? Just about everyone said something to the effect of “I’m working on all of
these items simultaneously”, and the list of items never changed from stand up to stand up.
Things weren’t getting done. And of course, every time the team didn’t complete the sprint,
Julian looked bad in front of his peers.

​ nsplash
Every stand up sounded like this picture. Welp. // Credits - U

 
  

 
What was the root cause of the problem? Sprint planning! In every single sprint planning, the
team regularly overcommitted to work. People tried to grab as much as they could so that they’d
look productive.

Julian decided to join one of Alana’s sprint planning sessions, to see what he could do better in
his own sprint plannings - and so he could finally stop being roasted during the weekly Product
Scrum of Scrums status update meetings.

So what was it that Alana and her team were doing differently? Well, first, Alana ensured that
she loaded the sprint in absolute priority order. That is, every single ticket was prioritized - the
first one was the most important, and the last one was the least important. No exceptions. The
order of the tickets in her sprints was exactly the order that her team executed against.

Alana and her team were also incredibly honest, transparent, and disciplined in not overloading
the sprint. The team refused to pick up any tickets that weren’t sized with story points, and the
team regularly called out their expected bandwidth for the sprint.

After all, stuff happens - people have weddings to go to, or get sick, or need to take care of their
kids. Alana’s team knew that overcommitting won them no points (pun intended) - rather, being
defensive and realistic with their time enabled them to report back to stakeholders with
reasonable timelines.

Julian brought back these insights to his team, and decided to give it a go. They “declared
bankruptcy” and started over, this time with story points on every ticket and with a sprint
bandwidth estimate for every teammate. At this point, Julian finally understood why he had to
write out user stories in such excruciating detail - because that’s what enabled everyone to size
the tickets correctly.

 
  

Size your tickets with points, please and thank you! // Credits - ​Unsplash

On top of that, Julian decided to spice up sprint planning a bit more. Whoever overcommitted
the most would have to personally pay for team lunch in the next sprint. Suddenly, people got
way more disciplined in a hurry!

And of course, others in the company started noticing that Julian had turned his team around.
When you take ownership of problems and execute thoughtfully, you get noticed!

But Julian wasn’t done yet. He also noticed that while his team had gotten way better with ticket
load, he was still struggling to hit the deadlines. And this was because part of Julian’s
development team was offshore in China, where the teammates there were noticeably less
productive.

His local teammates would always curse under their breath at the Chinese team. Of course,
during retrospectives everyone played polite while the video was still on, but as soon as the
video was off, Julian could hear his team swearing like sailors. And really, the retrospectives
were totally useless - his team only ever filled out the “What went wrong” section, without filling
in the others. It was truly a toxic environment.

He decided to put matters into his own hands. First, he needed to fix the offshore team’s
performance. Then, he needed to reunite his fractured team, fix their toxic culture, and really get
them to run real retrospectives.

 
  

Was it part of his job description? No. But was it crucial that he overhaul his team’s culture?
Absolutely - or else he would never be able to execute and deliver.

First, Julian set up time with each of his remote teammates to chat each week, and try to get to
the bottom of the problem with their performance. For each of these calls, he turned on his
webcam and talked through each person’s questions, needs, and career aspirations. He asked
them about their communication preferences and about their families, their areas of interest at
work and their hobbies.

By doing so, Julian ensured that he could meaningfully tailor work to each teammate, and
encourage them to step up. Basically, Julian wanted them to feel personally connected to the
work.

Then, he started holding office hours a couple of times each week for his offshore team. He
noticed that they didn’t really understand the U.S. market, so he took this time to bring them up
to speed with industry trends and dynamics.

Quickly, his offshore team started to gain in speed and quality. Success!

… except, not quite. His local team still spoke derisively of the offshore team.

So, Julian started a new team ritual. For each sprint kickoff, he had one of the local teammates
talk about U.S. culture, and he had one of the the offshore teammates talk about Chinese
culture. The goal was to rehumanize them team with one another.

Were the first few kickoffs brutally awkward? Of course. But did it work in the long run? You bet
it did!

People actually started looking forward to sprint kickoffs, because they would get to hear crazy
stories from each other. The Chinese team loved scaring the local team with ​their food choices​,
and the American team enjoyed talking about the neverending celebrity gossip in the US.
Retrospectives stopped becoming whining sessions or blame games, and the teams had real
praise for one another. They started trusting one another and encouraging one another.

 
  

​ nsplash
Team fistbumps! // Credits - U

Instead of retrospectives being full of only complaints, they were now meaningfully filling out the
4 core sections of retrospectives:
● What went well this sprint?
● What didn’t go well this sprint?
● How could we improve for next sprint?
● Which suggestions from last retro did we implement, and how did those go?

Alana was highly impressed with Julian’s growth. He had really gone above and beyond, and
his team was now operating smoothly. At their next walk, Alana offered this praise to Julian:

“You’ve grown immensely! You went from being a toxic teammate to being a responsible
servant leader, and you’ve even stamped out toxicity within your own team. That takes guts.
Well done.”

He beamed with pride - but gave the credit to his team for stepping up and being willing to
change. After all, that’s what product managers do, they give all the credit away!

In a Nutshell

 
  

 
● Execution is your foundation - you need to execute before you get the chance to craft
vision and strategy.
● Be empathetic, you work with a team to get things done! Understand what others need
from you, and why they need it from you.
● When you become a product manager, you’re a leader. If the team runs into challenges,
it’s your responsibility to resolve them.

Ch 4 - Tactics as a Product Manager

Julian had finally regained the trust of his team by executing with relentless efficiency.

After a few more months, he started getting restless, and booked time on Alana’s calendar to
talk about how to level up.

On their next walk together, Julian asks what’s next for him. He doesn’t feel like he’s learning
anymore.

Alana responds that success in product management is a moving target. As soon as you master
one thing, you have two more things to master. She recommends that Julian focus on product
performance.

His eyes light up. That sounds way more fun than writing user stories and running sprint rituals!

 
  

But he catches himself. Execution is still important. He reassures Alana, “I’ll still stay on top of
my current work. But just watch, I’m going to show you the best product performance you’ve
ever seen!”

Alana chuckles. “Okay, you’re on. You know that Kathy and Bridget also report to me, and that
they’ve been here way longer than you have. If you can outperform them, I’ll give you a
performance bonus.”

Julian decides that before he can improve product performance, he needs to understand
product performance first. And to do that, he needs metrics.

Look at those juicy metrics! // Credits - ​Unsplash

He reflects on his current set of metrics, and notices that there are a couple of gaps. He reads
metrics and data analytics blogs on the weekends to try to close the gap. Over the next 4
weeks, Julian becomes a pilgrim of sorts - he dives into textbooks, blogs, podcasts, and
webinars to figure out how to create and instrument metrics.

 
  

 
At some point, his team starts joking that Julian is now the metrics master, the guru of graphs.
Julian is visibly excited and is constantly muttering about North Star metrics, countermetrics,
and key failure indicators.

At the next quarterly executive readout, Julian volunteers to present his metrics to the execs.
Alana doesn’t see why not, and both Kathy and Bridget are cool with having him take some of
their time to present.

At the meeting, Julian pulls out graph after graph after graph, and talks through alpha, p-values,
and more.

...you can hear snoring in the room. Julian goes way over his allotted time, and Alana has to
intervene to transition to the next topic.

​ nsplash
Julian finally cured his CEO’s insomnia… whoops. // Credits - U

After the meeting, Alana pulls him aside to give him a dose of radical candor.

“Julian, I really appreciate that you put in all of this time and effort, but you completely forgot
about having empathy for your audience. The executive team is not interested in your analysis -
they just want the answers and the proposed next steps. Your graphs had no summaries or
takeaways, and you had no call to action. It felt like you were showing off, not driving towards a

 
  

 
decision. Next time, let’s have you practice with me - we have plenty more opportunities to turn
you into a meeting rockstar, don’t worry.”

Julian nods, embarrassed. He really did forget that the executive team doesn’t have a statistics
background.

Over time, Julian continues to polish his presentation skills, to the point where the team is
comfortable with sending him off to conferences to represent the company.

Julian continues to mature as a product manager. Of course, there are just some key traits that
don’t change - and Julian is an impatient go-getter. One of the things he absolutely hates about
his day-to-day work is the sheer number of meetings that he’s in.

“Meeting this, meeting that. Gah! There are so many meetings, why are there always so many
meetings?!”

Don’t take your frustration out on that pencil! // Credits - ​Unsplash

He checks his calendar and notes down that he spends over 80% of his week in meetings. He
really wants this to change.

 
  

He sits down in one of the empty conference rooms and reflects for a bit. So far, what he’s
learned from Alana is that he needs to have more empathy, and that he needs to be proactive
rather than reactive.

As he follows that train of thought further, he notices that most of the meetings he’s in are
fundamentally reactive. They’re all status update meetings or meetings to go over stuff that he’s
already sent out before.

He realized that the root cause of having so many meetings is that his company is culturally bad
at meetings. That is, most meetings are scheduled due to lack of communication, lack of
planning, and lack of alignment.

“Okay. Let’s say I have empathy. What problems can I proactively solve for people, so that they
don’t need to meet with me? Hmm...”

Julian decides to take the driver’s wheel. He notices that if he sets up a monthly 1 hour meeting
with a particular set of stakeholders, it would eliminate over 8 hours per month in status report
meetings.

So he does that. He puts together meetings with clear agendas, with clear assignees, and with
clearly documented next steps.

 
  

​ nsplash
Clear agendas = happy people. // Credits - U

Over the course of the next three months, Julian’s calendar magically frees up, since he’s
eliminated so many poorly defined meetings. In fact, Julian leads most meetings now, and he
sets them proactively. He rarely needs to be pulled into other meetings, because his
communications are so crisp and well-defined.

Alana notices that Julian has been totally crushing it on efficiency and effectiveness - although,
no, he didn’t win his bet with her. After all, he’s currently in charge of a legacy product, and it’s
hard to improve product performance on legacy products.

In their next development conversation, Alana mentions to Julian that the executives have
noticed Julian’s outstanding performance.

She smirks as she brings up the next topic: “Also, I haven’t forgotten that you’re all about
strategy. We’ve got a new product we want to launch, and I think you’re the perfect candidate
for the job. You in?”

“Hell yes I’m in!”

In a Nutshell

 
  

 
● Ask yourself: how can you maximize the team’s impact? Go above and beyond what
people ask of you.
● For your tactics to work, you have to really understand your stakeholders. What do they
care about? Why should they care about what you care about?
● Time is your most precious resource, and your team’s most precious resource. Spend
some time upfront to unlock more bandwidth for the long run.

Ch 5 - Strategy as a Product Manager

“Oh boy, what a headache,” thought Julian proudly. “I’m so outstanding that I’m going to do two
jobs at once. Look out, world, they don’t make geniuses like me anymore!”

Julian dove right into the new product area with gusto. He set up calls with external experts,
devoured research reports, crafted hundreds of pricing models, led dozens of brainstorming
sessions - you know, all the good stuff.

And of course, Julian learned from his past mistakes. He continued to execute on his legacy
product while pushing forward on his new product initiative.

 
  

 
Six months passed by in a flash.

At the next product review, Julian walked his team through the value proposition for his new
product area.

​ nsplash
Big meeting, high expectations! // Credits - U

“It’s a freemium networking feature that we’ll distribute through social media marketing.
Influencers on YouTube and Instagram will be our core distributors, and we’ll set up booths on
college campuses and music festivals to spread the word.”

His entire product team looked at him as though he had gone insane.

“Julian… we’re a B2B CRM company. We’ve never done freemium before, and our smallest
contracts start at $2 million a year. This strategy doesn’t make sense in the least.”

Julian pushed back passionately. “No, hear me out! There are millions of potential B2C users,
and we can hook early adopters quickly by targeting millennials, especially college students and
high school students!”

“Julian. Why would a high school student need a CRM? You’ll never be able to upsell them into
our core product.”

 
  

 
What happened here?

Julian didn’t take the time to understand the company strategy, and embarked on his own
strategy without aligning himself.

His company is enterprise - that is, they sell to businesses. That being said, B2C wasn’t
necessarily incorrect. After all, Slack’s freemium model is B2C, even though they make their
revenues off of enterprise B2B.

What really killed off Julian’s idea was that he didn’t understand the fundamentals of his
business.

Know your fundamentals! // Credits - ​Unsplash

What are the unit economics? How are the contracts structured, what’s profitable, and what’s
not profitable?

Where is the product portfolio strong? Where is it weak? Where are the churn risks, and where
is the potential for upsell?

 
  

 
What are the strengths of the product team? What are the gaps of the team?

His company’s head of product chatted with Julian in the hallway shortly afterwards.

“Hey man, it’s actually not the worst product idea in the world, but I’m pretty sure it’s not going to
work as a standalone. Why don’t you pair up with Kris and think about how a networking feature
fits in with his product? After all, he owns the help center product, you might see some
surprising synergies there.”

Julian was mystified - that didn’t seem all that natural. Still, he nodded and said that he’d hit up
Kris in the next couple of days.

Over coffee, Kris debriefed Julian on the history of the help center product, and on the roadmap
and trajectory.

Kris then mentioned: “What’s been a pain is that when most people hit a problem, they don’t
ever go to the help center. Most folks don’t like reading, and don’t know how to navigate those
articles. I like your idea of networking, because users trust other users more. Here’s a crazy
thought - what if we had a Stack Overflow-like forum, but for our own product? You could use all
of your existing networking ideas - badges, profiles, interests, notifications, all that jazz!”

Julian’s mind was blown. Actually, that wasn’t a bad idea at all!

By bundling products together, he could unlock totally new kinds of interactions and use cases
for his company and for his customers.

Within the next year, Julian launched his networking product within the broader company CRM
product portfolio, with a heavy focus on bundling with the help center product. His sales team
was able to upsell to all of their key accounts, unlocking tens of millions of dollars in annual
recurring revenue.

 
  

A solid launch. // Credits - ​Unsplash

While Julian was ecstatic, he was also frustrated. His legacy product really wasn’t moving the
needle - in fact, it had lost ground to competitors. His teammates were all quitting or transferring
to other product initiatives that were more interesting.

One of the key questions in product management is prioritization - what are you going to let
burn? After all, you only have 24 hours in the day, and only 7 days in the week.

In Julian’s particular case, it wasn’t okay to burn his old product since it kept out potential new
entrants from attacking his category.

So, Julian went back to his team to rally the troops and show them why it’s important to keep
the old product alive and kicking.

Based on what he learned with creating effective meetings, he started also to empower his team
to come up with new ideas. He taught them how to run experiments and A/B tests with his
guidance. Over the next three quarters, the legacy product started to hold its own again - and
without much of Julian’s time.

 
  

 
His exec team was impressed - most PMs can’t handle both new and old products, but Julian
was crushing it on both fronts. At his next career performance review, Julian received a
unanimous recommendation for a raise and for additional stock to be awarded to him.

In a Nutshell
● Products don’t operate in a vacuum. Know the context of your product: industry,
company, competitors, and product portfolio.
● Experienced product managers have a strong grasp of the business side, because that
context enables them to make better decisions.
● New products and legacy products are fundamentally different. Know which one you’re
working with, and understand how that might change your high-level objectives.

 
  

Ch 6 - What does career progression look like?

Of course, Julian was happy with the raise!

...well, except for one thing. His title hadn’t changed at all. He was still a Product Manager in
title.

“My raise doesn’t get me any higher up the ranks. Also, this doesn’t seem to be getting me any
closer to launching another startup on my own.”

Julian felt lost. Yes, he was happy about the raise, but he wasn’t quite sure how this fit in with
his future.

He interviewed his network, inside and outside the company. What are the career paths for
product management?

​ nsplash
Share your wisdom with me! // Credits - U

 
  

 
At the end of six weeks of interviews, Julian had interviewed 26 people, to no avail. He found
out that there isn’t a standard career path for product managers.

Rather, product managers need to create their own careers.

So, it’s up to Julian to drive his own career.

He realized that for his career to make any sense, he needed to first decide what he wanted.

Does he want prestige? Power? Stability? Excitement? Empowerment?

Does he want to mentor people or be his own individual contributor?

After a couple of weekends of reflection, Julian acknowledged that he loves to incubate new
ideas. While he demonstrated that he’s good at scaling an existing product, that’s not what he’s
passionate about.

He also figured out that he really doesn’t like to mentor other people. And that’s okay - some
people simply don’t want to be people managers, and that’s an entirely acceptable career path
too.

So, Julian started identifying more and more product initiatives that he could launch, in tandem
with other PMs or on his own.

He turned down opportunities to scale existing products, and kept his focus on incubating new
ones. He turned down opportunities to formally manage more junior PMs, though he was always
open to getting coffee to share what worked for him in his career trajectory.

 
  

Coffee chats - because caffeine makes everything better! // Credits - ​Unsplash

Was it different from what the other PMs in his organization were doing? Sure. But being
different is what got Julian here, and being different will continue to carry him forward.

Keep the following quotes in mind:

● ​ eter
“Today’s ‘best practices’ lead to dead ends; the best paths are new and untried.” P
Thiel
● “Do not go where the path may lead, go instead where there is no path and leave a trail.”
Ralph Waldo Emerson
● “If the path before you is clear, you’re probably on someone else’s.” J​ oseph Campbell
● “We have to continually be jumping off cliffs and developing our wings on the way down.”
Kurt Vonnegut

In a Nutshell
● You were fearless to break into product management - so you have to maintain that
fearlessness to keep pushing forward!

 
  

 
● Only you know what’s right for you. Ask others for guidance, but experiment on yourself
and trust yourself.

 
  

Ch 7 - Intellectual honesty and retrospectives

Let’s step away from Julian’s journey for a moment, and focus on you, dear reader. Now that
you know how to think about your first quarter and a bit at your new gig, we think it's a great
idea for you to reflect.

All retros are about intellectual honesty and all intellectual honesty boils down to:

● What percentage of the time are you happy? Why is that the case?
● What appeals to you? Why does it appeal to you? Can you test that hypothesis?
● What would you rather do instead of what you are doing now?

Don’t be Dwight // Credits - ​Quickmeme

So let’s set the clock back, and look at the end of Julian’s first quarter on the job. He spent that
quarter learning about the industry and coming up to speed on the product that he owns. He
had a basic idea of the framework that he wanted to think about success in his new job. At the
end of his first quarter, it was time for a vacation. Unfortunately, as with most airlines, his flight
home to spend time with his family was delayed.

So now he was sitting in his magnificent open floor plan office overlooking, well no one.
Everyone else had left for vacation the day before. Turns out quiet places are really great for
work and open floor plans don’t really help noise. Anyway, we digress. He had a solid hour to go

 
  

 
burn and he did not want to do his normal spec work. He was tired of opening and closing his
spec doc and his SQL skills were well beyond the point of atrophy for a Friday afternoon.

So he decided to reflect back on his time at work. It wasn’t an Eat, Pray, Love expedition but
more of a “here’s what I think I wanted, here’s what I did”. He looked back at the job description
and decided to do an audit. Here’s his framework below:

Skill # What skill do I want? How will I get it? How long will I need?

1 Enterprise deployment Project 1 6 months

2 Platform product expertise Project 2 9 months

... ... ... ...

It’s hard to figure out Projects 1 and 2 before you join in. But it is critical to look at the Skills. The
skill sections are non negotiable. Remember, if you don’t know where you’re going, any path will
get you there. Don’t make that mistake.

Julian then compared his skill matrix from before with what he was actually doing. The
difference between what he thought he would do and what he was actually doing were pretty
staggering. He had nothing going for enterprise deployment, but he did pick up a ton of
negotiation skills that he had no idea would get honed in his role when he started.

By the way, we’ve pulled together a Skills Inventory template for you ​here​, so you can do what
Julian did. Convenient, isn’t it? You can copy it by clicking on File in the menu bar, then clicking
on “Make a copy…” (if the option is grayed out, make sure that you’re logged into your Google
account).

Julian also did a retrospective, it’s just like a sprint retro but for yourself.

What went well? What didn’t go well? What could have gone better?

Project 1 Sales - PM relationship Customer empathy

Personal development Platform story Project 2

... ... ...

These work out well because you need to be honest and introspective. Make sure that you do
them at least once a quarter. And schedule them out. Don’t be like Julian who had to get his
flight delayed to make this work.

 
  

In a Nutshell
● Be honest with yourself, it is the only way to figure out if you’re actually happy or not
● Make time for a retrospective, at least once a quarter
● Take notes about your work, they will help immensely