100 Lessons and Spicy Takes on Being a Software Product Manager

It’s hard for me to believe, but I’ve been working in the software tech industry for 10 years now. For the vast majority of that time, I’ve either been a product manager, or a founder with a heavy focus on product.

With the trend on Twitter of 1 like = 1 insight or spicy take, I decided to jump on board the trend and do one on product management. It appears to have resonated:

So 100,000+ impressions later, it seems that it really resonated with people.

With the ephemeral nature of Twitter, I wanted to preserve those takes for easy future reference, so this post represents them.

100 Insights + Spicy Takes on Software Product Management

There’s some great discussion around many of the tweets, so I encourage you to check out all the discussions here.

The trick to tell if there’s a reply to a tweet is to look at the speech bubble in the bottom left corner of each tweet:

look to the number of comments to see if there's a response to that tweet

If the tweet says 1 in that area (like Tweet 2/), then the only reply is my subsequent tweet in the thread. If it’s more (like  Tweet1/) then there are replies to click on and see.

Anyways, let’s get onto the takes:

1/ Being a PM is a job of influence. The best PMs are the mayor of their area of work. You need to be able to build coalitions, and get buy in from a wide group of people.
That doesn’t happen by accident. It takes work.

2/ The best PMs are autodidacts. They’re constantly curious and always learning.If you don’t like learning lots of new skills from sales, to marketing, to negotiation, to EQ, to design, don’t be a PM.

3/ PMs are also like a point guard playing basketball. Done right, they set up many others to look great.A strong collaboration makes your designers create better designs, and the engineers ship a better product faster. Those assists don’t show in the score sheet but matter.

4/ PMs also are limited by their team. If you are missing key players or have weak players at other positions, it will often look like the PM is weak, because they have to cover or fill in gaps.Two of the toughest are PMs w/o good design help or lacking a good tech lead partner

5/ There are many ways to become a PM. You cannot major in product management, so everyone gets their start different ways.If you think you want to be a PM, look into how people you follow did it. You may be surprised how varied it is.

6/ The best ways to become a PM:
A) Excel at a growing company & ask to transition (seen it work great for marketers, customer success, design, & engineers)
B) Do a side project or startup to show you can PM (this eliminates the chicken or egg problem of having never been a PM)

7/ Getting an MBA won’t help you become a good PM.It won’t make you a better PM if you already are one, either.If you want to become a GM at a company, an MBA makes sense, but it doesn’t help product managers.

8/ I’m sure the previous tweet is going to get some replies from a Sloanie, HBS grad, or Stanford MBA.As is always the case on Twitter, exceptions always get mentioned, but do not disprove the general statement. Save $200k if you love PM and don’t get an MBA.

9/ Most of the worst PMs I know or have heard about are either former engineers or MBAs.
– MBAs often bring ego + don’t want to do the real work (talking to customers, iterating, etc)
– Engineers can struggle with the interpersonal & relationship building side of PM’ing.

10/ If the sales team is at war with your product team, or people try to go straight to your engineers for pet requests, those are your fault.The #1 mistake that good PMs make is not building relationships across departments. Fix it with peer 1 on 1s: https://jasonevanish.com/2015/09/24/product-managers-peer-one-on-ones/

11/ The #1 mistake mediocre & bad PMs make is not talking to customers.It’s scary getting outside the building, and they instead choose to be master BS artists.If this is you, change your ways in 2020. I wrote how-to’s I wish I had when I started: https://jasonevanish.com/product/

12/ There are 31 flavors of product managers. An A+ PM at one company would be terrible for another company.If you’re hiring, recognize this could explain a short stint on a resume, and if you’re job hunting, don’t apply to PM jobs that don’t match your skills & strengths.

13/ PMs fit differently based on a variety of factors such as:
– The business model (Ecommerce vs. SaaS vs. Ad tech are dramatically different jobs)
– Company stage (Think public company vs. Series B vs. Seed)
– Company culture (How are decisions made? What do they value?)

14/ The interview process for product management is completely broken. 

15/ There would be no need for a whole market for products to “Master the PM Interview” if the interview process was actually good at most companies.

16/ The best interviews see if you can do the work *you’ll be hired to actually do.*Unfortunately, most PM interviews are veiled in hypotheticals that have nothing to do with the job, and are basically trick questions.Mastering trick ?s has nothing to do w/ being a good PM.

17/ Most product teams don’t check their applicant tracking system nor respond to applicants who apply cold.This is ironic given the trend of calling PMs “Mini-CEOs”, and recruiting is one of a CEO’s most important jobs… 🙄

18/ If you want to get a response on an application, get an intro into someone on the team.Don’t have a network? Search LinkedIn for lower level PMs. No one asks them for help, so they’re more likely to respond & have a call/coffee to discuss the culture, then refer you in.

19/ The first PM hire at startups is almost always a sacrificial lamb at the altar of learning for the founder.Read more why and what to do about it here: https://jasonevanish.com/2019/04/28/second-1st-pm/

20/ The best job if you love startups is to be the *2nd* first PM hire, as you get all the opportunity, equity, and influence…all thanks to the PM that came before you.They died on hills, and helped the company learn what they actually wanted.

21/ Most customers don’t report bugs or give feedback.They just quietly suffer, or churn and then maybe tell you. 

22/ I follow the “Rule of 10:” If 1 customer has an issue, there are probably 10 more that didn’t say anything. 

23/ If you have an issue, get in the habit of sending a note to those affected. It’s good service AND it helps you quantify issues.I’ve had many engineers be surprised when they see that 2-3 tickets is actually affected TONS of users. Getting a list to email helps quantify it.

24/ Customers don’t care how hard (or easy) a feature was.All they care about is if you solve their problem or make it possible for them to do what they want to do.

25/ Quick Wins (aka – simple things you can do to make the product better for your customers) is a great way to let your team recharge and build some momentum after shipping a big feature.Sometimes customers are more excited by this than your big feature.

26/ Product/Market Fit exists for both buyers and end users.You can have one and not the other, and it will cause your business to sputter.

27/ Never become a PM at a company where the founders don’t understand what a PM does. You’ll get no credit for wins + all the blame for any problems.Fateful last words include “that feature went really well, but I have no idea how you contributed” & “Why can’t you just…” 🤦‍♂️

28/ Jeff Bezos was right when he said this:

“The thing I have noticed is when the anecdotes and the data disagree, the anecdotes are usually right. There’s something wrong with the way you are measuring it.”

The problem is most PMs don’t talk to enough customers to tell this is the case.

29/ There’s nothing like doing product management in Silicon Valley. There, PMs are mostly considered vital and valuable parts of the company. This changes who does the job, and how they work.

30/ If you want to be world class at product management, you need to work a few years in Silicon Valley for this reason, and many more.Being around that many product obsessed, super smart people, will level you up rapidly.

31/ A long time product consultant in NYC told me, “NYC product is 20 years behind the Valley.” That feels directionally accurate.I think there are *many* smart, great PMs in town, but it’s structural/cultural issues that undervalue product here: https://medium.com/@Bosefina/how-to-be-a-product-driven-company-in-nyc-342fd689877e

32/ The mascot of NYC PMs would be Eeyore.The amount of self deprecation I’ve seen/heard that really feels like “haha, it’s funny, but I’m actually sad about it” has been one of my biggest surprises.Product is undervalued in many cases here!

33/ One of the hardest remote jobs is being a PM.Collaboration and innovation are where the magic happens, and that’s the greatest weakness of remote work.There are ways around some of it, but it takes a lot of conscious effort. 

34/ If you’re a remote PM, use any flights or face time you get to try to solve your biggest challenges.Nothing remote can compare to the energy of being in the room at a white board with your designer and engineer(s) working on a problem. 

35/ Also document, document, document, and share, share, share.You can’t walk by your pod and tell them about a great customer interview, so you need to find other ways to share what everyone needs to know…in a light weight way they’ll actually read/see.

36/ On the flip side, remote can help bring out some of the best work of your designers and engineers as they can more easily get into deep work and focus.Try doing that in an open office…

37/ The #1 skill to develop to be a better PM is to become a better writer.

38/ Writing touches everything you do as a PM:
– Product specs
– Updates to customers
– Updates to stakeholders
– Note taking in meetings
– Notes and takeaways from customer interviews
– Writing good survey questions
– Communicating to your team

39/ To become a better writer as a PM, write more:
– Blog posts
– Internal documents
– Tweets + Tweetstorms ;)
– Personal notes to collect and organize your thoughts.
– Emails and experiment with templates you use.

40/ The other way to become a better writer is to read more. Read regularly, and you’ll find your vocabulary gets stronger and you always learn.

41/ My favorite books to help you write #1: Tested Advertising Methods amzn.to/2sHa6OH
– Copywriting goes everywhere from the marketing site, to help docs, to inside your product
– You probably have to write some of that
– The lessons apply beyond that
H/t @LarsLofgren

42/ My fav books to help you write #2: Never Split the Difference amzn.to/2Ff5HoL
– You do a lot of negotiating as a PM. This teaches you a better approach whether working with an angry customer, negotiating with another team for resources, or deftly handling your boss.

43/ My favorite books to help you write #3: How to Win Friends & Influence People amzn.to/2ZJOLQG
– PMs are in the people business and this is the gold standard to working well with other people. This applies as much to what you write as what you say.

44/ The best way to earn respect from an engineer is to have data to back up what you tell them. Show them the customer interviews & quotes, or the analytics/data and you’ll engage them much more in what they’re building.This wins many more people over than a batle of opinions.

45/ The easiest trap to fall into as a PM is to ship things and never check the results of your work.Set a reminder for yourself 2 weeks or 2 months (depending on your company stage) later to go back and see what worked or didn’t. 

46/ Setting up analytics and measurement of a new feature is as important as making sure all the buttons are where they should before launching your feature.It should be part of your product spec. (I like @joshelman‘s approach for that https://jasonevanish.com/2014/06/03/how-to-write-a-product-thesis-to-communicate-customer-needs-to-design-and-engineering-teams/

47/ Ship early, ship often.

48/ I follow the “Estimation Rule of 2X:” Any project’s estimate is always off by 2X.
– When it’s 2 vs 1 day, or 2 instead of 1 hour, it’s not a big deal. However, the bigger the project, the more brutal this becomes (4 weeks vs 2 weeks, 4 months vs 2 months is a problem).

49/ PMs should be tool agnostic. Whatever your engineers will actually use and keep up to date is the project management tool you want to use.The tool you love for the burn down and gannt charts is not the hill to die on if all your engineers hate it.

50/ “Your startup either dies, or lives long enough to end up using Jira.”
This saying I used to hear 5 years ago still seems true. 

51/ PMs should be infinitely curious. If you see something you don’t understand you should want to investigate.
– Look into the analytics, ask the engineer to explain why, ask what motivated your designer to go that direction. You’ll learn, and it often sharpens their thinking. 

52/ If you’re a Senior PM or higher, you should be mentoring people inside and out of your company.It’s great to give back AND it will make you a better PM.

53/ Every time I help someone as a mentor, I walk away with a few new ideas and usually a reminder of a few things I know I should do that are slipping.

54/ It’s never been easier to get a mentor. A few ways people have reached me, and I’ve gained help:
– DMs on Twitter
– Well crafted Linkedin messages
– Cold emails after they read my blog and found my email address on there.
– Replies to blog post emails from subscribers.

55/ Creating a bonus structure for PMs is a very risky move*. If your company’s needs to change, you want PMs to be flexible, but that’s hard to convince them if their bonus says otherwise.* Exception = E-commerce it can work since it’s easier to have a consistent target.

56/ Being pedantic is a terrible trait for a PM.Care about the details, but in a tactful way. Know what hills to die on, and how to have both strong opinions, *and* loosely hold them.

57/ The art of knowing where and how to draw the line between high quality and shipping on time is one of the hardest skills to develop as a PM.Those that master it are worth their weight in gold.I like @Wayne‘s essay on this: https://blog.usejournal.com/want-to-build-an-incredible-product-strive-for-the-delta-of-wow-f184b716af18

58/ Being a founder, even if your startup fails, makes you a much better PM.
– You appreciate other roles more as you likely wore their hats
– You learn to ruthlessly focus on the metric that matters most
– You learn to deal with extreme constraints & the creativity that breeds

59/ A good PM is like glue & grease:
– Glue to hold things together and fill in gaps
– Grease to make things run more smoothly and adapt to changes

60/ Feature voting tools are for mediocre PMs.

61/ Show me a feature voting site for a product and I’ll show you a graveyard of unanswered customer requests and a lot of noise.

62/ Show me a product team that relies on data from feature voting, and I’ll show you a team that thinks they know their users a lot better than they actually do.Some day I’ll finally turn this into a blog post it deserves:

63/ Companies that struggle with endless debates about their products and roadmap typically are arguing opinions, which ends up creating lots of politics and the most important person in the room making calls.

64/ Companies focused on their customers settle their debates one of two ways:
1) They ask “What’s best for the customer?”
2) They plan an experiment or table the discussion until they get some data/evidence

65/ Disagree & commit is an essential skill for any PM.You need to do it sometimes, and so does everyone else on your team.The key to avoiding resentment is to measure the results of the decision. Everyone is wrong sometimes, and that’s okay as long as you fix it later.

66/ Great product leaders are unsung heroes: Their teams get all the credit if it works, and if it doesn’t, they are the ones to have to answer.

67/ Getting customers to talk to is hard and interviewing them is time consuming, which is why so many PMs rarely do it.

68/ Getting customers to talk to you is a team effort:
– Get customer success to forward you customers with issues in areas you’re fixing
– Reach out yourself (email, @intercom, etc)
– Partner with marketing on surveys & reach out to interesting answers.
– Talk to sales leads

69/ Joining a company to change their product culture is like signing up to climb Everest in shorts.It may be possible, but there’s a good chance you’ll die trying.

70/ Product managers pre-product/market fit have a 10X harder job than those post-product/market fit.

71/ The stronger the product/market fit, the easier it is for any product manager to look smart and deliver wins.A lot will be obvious, and in many cases, anything you build will work.

72/ Being hired as a PM to help a startup with a solution looking for a problem always leads to failure.The power dynamics and negative inertia are too great. Also, the founders should have been figuring it out, not a hired gun with 0.5-2% of the company.

73/ Some PM jobs are really project management jobs with a power struggle left off of the job description.

74/ Sharing wins and happy customer quotes are great ways to give your team a jolt of energy.We have a Slack channel dedicated to it at Lighthouse called #HappyManagers specifically because of this. Anyone can scroll through to read stories, quotes, and testimonials.

75/ When something is broken, the best way I’ve found to motivate a designer or engineer is to share the customer’s words directly.It’s one thing when you say it, but when they hear a customer say it, it hits their ego differently in a good way so they want to fix.
Side note: My favorite story of exactly this happening was also one of my proudest moments as the PM at KISSmetrics: web.archive.org/web/2012112303…

76/ Beautiful designs aren’t always usable or accessible designs.

77/ The #1 thing I’ve always had to remind designers I’ve work with is “Do you think a 50 year old with bifocals can read that”?

78/ McDonald’s theory is a great way to get your team unstuck:Suggest something you know will be rejected to get you back on the track of what you all do want. medium.com/@jonbell/mcdon…

79/ Harsh truth: The best products don’t always win.Sales & Marketing machines can be just as dominant, if not more so.

80/ In some markets, adding more features to demo & put on your pricing checklist is more valuable and important than any of the features being particularly good or useful.

81/ Tech debt doesn’t matter right until it might kill you.

82/ Adding another feature won’t help your company win if the ones you already have are broken.

83/ Tech debt is rarely talked about publicly, but many well known startups (both successes and failures) have faced major reckonings because of it.

For example:

84/ As a rule of thumb, once you’re onto something charging to or past P/M fit, spend 20% of your time on tech debt.This keeps it from crippling you and halting all progress (or killing you) later.A nice overview is here: https://blog.crisp.se/2013/10/11/henrikkniberg/good-and-bad-technical-debt
And the legendary Marty Cagan wrote about it here: https://svpg.com/engineering-wants-to-rewrite/

85/ My favorite way to pay down tech debt is to revisit/iterate on old features. This way you squeeze in a few quick wins (remember tweet #25?) along with fixing a troubled, decaying part of the product.It also helps keep the engineer(s) working on it thinking about customers.

86/ I knew @SlackHQ Channels could help with customer bugs and issues, but I was pleasantly surprised how well it also works to source customer development & product feedback fast.This is an amazing post on the topic from founder/CEO @stewart: https://slackhq.com/shared-channels-growth-innovation

87/ Always be iterating on your processes. What worked for a small team or company will break as you grow.Fortunately, said breaks are predictable: https://getlighthouse.com/blog/company-growth-everything-breaks-25-employees/

88/ The best way to iterate on your process is to make it a habit:
– Post Mortems (even when things go well)
– Peer 1 on 1s to get individual/private perspectives
– Ask for feedback after a ticket is closed (What can I do differently to make that easier/better next time?)

89/ The best way to scale being a customer driven company is to get everyone involved.You can’t be everywhere, but you can teach bits and pieces to others. Teach them how to ask a good followup question over email, or to do some of their own interviews.

90/ You need thick skin as a PM. You will fail and need to find another way. You will take more blame than you probably deserve.I’ve interviewed and been rejected by more companies than you’d ever guess. Lost many deals. Been flaked on by customers over and over. It happens 🤷‍♂️

91/ Focus groups are a disaster. Customer development is *one* customer at a time.You need to hear their individual stories and situations, not group think.

92/ Remember what Steve Jobs said on simplicity:“Simple can be harder than complex: You have to work hard to get your thinking clean to make it simple. But it’s worth it in the end”The best solution is usually not the first idea. Keep pushing to get it right to unlock magic.

93/ Sometimes the best move is to kill a feature, not add another.

94/ My favorite way to learn is to read based on the biggest challenge I’m currently facing.This insures you immediately apply it to your work…and I find also motivates you to finish reading faster.I’ll share some good places to start after #100

95/ The product tours industry feels universally overpriced.None of them show you how to calculate ROI for what they charge, and typically it’s a small part of successful onboarding + educating users.

96/ Onboarding is really hard.- Customers don’t read.
– They skip overviews and tours.
– They quickly get bored of videos…then complain they “don’t get it.”And it’s still your job to help them get to the AHA! moment.

97/ The best way I’ve learned to make onboarding work is to use a lot of “lead bullets” mixed with experimentation.A little bit of everything makes it so there’s something for everyone.Ideally, you’ll simplify & help them focus on 1 thing, but that can be resource intensive.

98/ @intercom is the best product category for startup PMs since the development of modern analytics changed how we measure and made data accessible to everyone.

99/ Some mistakes you can learn from others and avoid. Others end up being learned the hard way.Be nice. What’s obvious to you may be a difficult lesson for others, and vice versa.This is especially true in product given how varied all our backgrounds are.

100/ Time management is a crucial skill as a PM; know where all your hours go every day & make sure you get the important stuff done.This video is a great way to conceptualize that:

Further Reading:

Want to learn more PM skills, my reply here gives a few people to start with:

– Read lots of books. My favorites by category here: jasonevanish.com/bookshelf
– Rafael Balbi: Who are some great PMs you regard from the west coast? I’ve been interested to learn more about these differences.

A few off the top of my head (some aren’t PMs anymore or were pm minded founders but their blog posts and presentations are still gold) @cagan @joshelman @BrianNorgard @rrhoover @jmj @hnshah @Pv @seanrose @Bosefina @cindyalvarez @DesignersGeeks @wfjackson3 @ShaanVP @danolsen

Also would add @kennethn  and his great blog: kennorton.com/newsletter/ and the classic post by @bhorowitz

Search for their blogs and you’ll find gold mines.

I’d also add that part of it is company structure / culture, not a difference in skills. It sets you free to do things that in a different structure and valuing of product that wouldn’t allow or would be serious upstream swimming.

I’ve dedicated the last 5 years of my life to helping people be better managers.

If you have a big team to manage, sign up for a trial to make your 1 on 1s organized, motivating, and accountable, or tell your eng. manager to check us out: getlighthouse.com

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