An Intro to PM Interviewing

Who is this for?

Last year* I gave a talk to the Harvard Business School tech club, titled “Prepping for PM Interviews, or 16n hours of your life, where n=number of companies you interview with.”  This is a variation on that talk. I’ve started thinking about it more again as we consider how we’ll grow our product team at Lola in the future.

I hope sharing this framework is helpful from both sides of the table:

1. If you are interviewing potential PMs. If you don’t have a framework for PM interviews yet, this hopefully will give you one to build on. When I started interviewing for PM, I got “don’t get sued” lessons, but not “here’s what to look for” lessons. This is how I think about it. Here’s another list from Pivotal about 29 things they look for.

2. If you’re interviewing for PM roles,
this is one way to think about sharing your skills. You might also want to look at my previous piece on ways to screw up your interviews.  Also, lots of people have written about this before from the candidate side. I also recommend thepminterview website and Cracking the PM Interview.

What’s the point of a PM interview?

”Product Management isn’t a role or function, it’s a set of skills.” – Satya Patel.

Product Management isn’t taught formally, so the skills of each candidate tend to differ. I look for three things:

  • A basic understanding of each key PM area (business, design, technology) and desire to learn more about each.
  • A significant depth of knowledge in at least one of the three.
  • Someone who brings at least one “superpower” to the team that no one else has.

Since Product Managers interface with lots of pieces of the company, it’s also important to get a good feel for work style and behavior.  To evaluate all of these areas, the PM interview often includes some or all of these steps: resume/intro/cover letter/etc, recruiter or HR screen, phone screen(s), “homework,” in person interviews, and references.  (Here’s what I went through with Kickstarter).

General PM Questions

Since Product has become “trendy” as a career, it’s important to understand why the candidate wants to get into Product. I screen people out based on answers that show they don’t understand the role of discipline. The wrong attitude about Product can be devastating on a PM team. 

  • Why do you want to get into Product Management?
  • What did you learn in your PM internship?

For candidates who are already experienced in Product, I tend to ask them the past tense versions.

  • Why’d you decide to get into Product?
  • What’s your favorite/least favorite part of working in Product?

I also like to pull these into general Product sense or tie into the company:

  • What’s your favorite product?
  • What product is popular, but you don’t like?
  • What do you like/dislike about <our product>?
  • How’d you find out about <company>?
  • Why do you want to work at <company>?
  • (Important!) Tell me about a project you’ve done.

Business Skills & Awareness Questions

Historically, this has been one of my weaker areas both as an interviewer and interviewee. I’ve been focusing on it more recently. This is a way to assess the candidate’s quantitative skill, and get at things like 10% vs 10x products.

  • How many people use our product?
  • What do you think of <company’s> business model?
  • If we needed to grow <any business> by x% from a new feature, how would you figure out what to add? (Or what would you add?)
  • How would you estimate the LTV of a new customer who just started using <company>
  • What’s the value of adding a host vs a customer to airbnb? (or any marketplace).

Estimation is another popular area that I don’t typically ask about:

  • How many piano tuners are there in NYC?
  • What would you have projected the market size for DVD players to be in 2008?

Design Skills Questions

This is the area I rely on most. I’m looking to get a feel about how thoughtful the candidate is in their work, and how they think about building new products vs. improving old products. I’ll often add twists into these to see how candidates deal with changing constraints.

  • Tell me about something you’ve built.
  • What would you do differently if you were building it again?
  • Design a New Alarm Clock
  • Design a Parking Meter system to optimize revenue
  • What are 10 ways we could improve <X>?
  • how would you change <our product>
  • You mentioned earlier you were into <hobby> what product do you wish existed in that space?

Technical Questions

This is the area I rely on least. I’m most likely to use it when interviewing a PM who does have an engineering background. I’m mostly interested in if people are technically curious. I’m also giving the least example questions here because they’re the ones people are most likely to memorize.

  • What’s a real life example of iteration and recursion? (Since I already shared that here).
  • When you go to a URL in your browser, how does the data get back to you?
  • Logic Puzzles (can’t share these without ruining them).
  • Pseudo code questions

Asking Good Questions

Almost every interview leaves time at the end for questions.  A huge part of the PM role is asking good questions, so this is really just another interview question. I like when the candidate asks me something I haven’t thought about before. I’m not going to give away the good ones, but here are some pitfalls:

  • Close-ended questions like: Do you like it here?
  • Questions that are better for HR, or don’t relate to PM: What are the hours like? How flexible is the vacation, really?


A final note for those who are interviewing: PM interviews often end in rejection without clear feedback. Part of the reason for this is that the PM team depends so heavily on balance between team members. If you’re an awesome PM from the business side, but the company already has two of those and needs someone technical, you could be rejected. It’s not your fault, you just haven’t found the right place yet. If you’re being rejected repeatedly, it’s more likely worth re-evaluating and figuring out which skills you need to develop further.

* A note: part of why I didn’t publish this a year ago was that I was worried about sharing the questions so broadly. I decided that the questions are just starting points. I’m trying to use them to get interesting stories from the candidate that showcase their skills. If someone were to memorize all of these answers without commensurate experience, they wouldn’t perform well in an interview.  I also thought it was unfair that I was willing to give questions to HBS people, but not to others.

2015 in Review

I read my 2014 in Review as I was writing this one. I laughed at the opening. Despite my insistence that I’d prioritize more in 2015, it didn’t happen. It was another very full year, for both large and small things. I finally met someone solely because of their Olin ring! I got sicker than I’d ever been before (ugh). We got engaged. Gutenberg continued to be an excellent household member.  I’m going to newly resolve to focus better in 2016. I even rearranged my phone’s home screen to focus on that goal.


When 2015 began, I was still at HBS. I covered that pretty thoroughly as the year happened. Here’s the summary of what I learned throughout the year, and my round up of ways I think that HBS will change.

HBS wasn’t just about class. These three activities I did outside of class contained lessons that still stand out:

  1. Startup Lockdown. We went through the process of starting five companies in five days. I learned a lot about my work process that I’d never questioned before. I think the biggest thing is – no matter how long you’ve been working a certain way, that doesn’t make it right.
  2. Google ATAP Visit. Regina Dugan visited HBS from Google ATAP. I was fortunate to attend her talk and a small dinner after. She had an uncanny ability to hear what I meant, rather than what I said. It was a next-level version of “always take the most respectful interpretation” which I learned from Bill Stauber at Microsoft. Since then, I’ve been trying to cultivate that skill. Listen to what people want to be saying, not what they do say.
  3. FIELD3 Presentation.  I got the change to speak on stage to pitch our entrepreneurial project to all 900 RCs (photo!) My presentation contained an unintended joke, and I had no idea how to respond when the audience started laughing.  Living through 900 people laughing at you really kills the public speaking jitters.


Working on Lola was a huge part of my year. I started as an intern doing research for Paul in April. That research evolved into pieces of our new travel company. Now I’m leading the Product team. Though this was one of the biggest parts of my year, it’s still ongoing and thus difficult to reflect on. Maybe next year there will be more to say.

A cool side part of this is that I went to Travel Agent School and now I’m a certified travel agent.


I got to take a few cool trips this year. I started out in Jakarta, working with a cereal company on a project for HBS. After that, I headed to Cambodia and Angkor Zen to do yoga. I happened to arrive on the same flight as another solo traveler, so we explored temples together. I also had the chance to go to Iceland with my parents for my birthday, France with my entire family over the summer, and Quebec City for the second iteration of Design Play.


I wrote a little less this year. A total of 38 pieces: 32 for the blog, 2 for Medium (cross posted to Business Insider), and a few interviews. I’ve also started writing for Aha! (on feature creep) and will continue to do so next year.

My HBS summary piece was my most-read (ever). While the title is clickbait-y, I think it has a lot of substance and I am proud that people found it as useful as they did. I re-learned to never read the comments. That said, I’m most proud of the piece on how HBS will change by the time I return.

Speaking & Teaching

The most notable thing this year was the end-to-end class I taught at Olin. I also just filmed a class version of the blog post I was most proud of last year for Skillshare (that will open next week). I taught a PM Bootcamp at General Assembly throughout the year and evolved the course, but have decided to stop doing that in order to have more focus.

I gave a talk I was proud of on checklists (but haven’t shared yet!) at Industry Summit in Cleveland. I plan to attend the conference next year – join me?

Next year I’d like to do more speaking. Have an event that might be a great fit? Let me know –


I read 144 books this year. The full list is on my Goodreads (with every book I’ve read since 2009). This year was much more gender balanced – 79 by women (55%) and 65 by men (45%). Once again, the balance came out almost dead even between fiction and not – 49% fiction, 51% nonfiction.

I always have a hard time deciding what to share as highlights. This year I’m defining it as “the books I couldn’t want to go back and finish.”


  • The Signature of All Things – Elizabeth Gilbert – most people read Gilbert’s nonfiction work, Big Magic, this year. I read both, and while I wasn’t a fan of Big Magic, I loved the Signature of All Things. I was happy to see she loved it as well (which I found out by reading Big Magic). It was a wonderful adventure throughout Polynesia.
  • The Martian – Andy Weir – This was my “Ready Player One” of this year. I was always on the edge of what the next engineering challenge would be.
  • A few others I enjoyed: Aleph (Coelho), Americanah (Adichie), The Knockoff (Sykes and Piazza), Dietland (Walker) and Kitchens of the Great Midwest (Stradal).
  • A guilty pleasure was the Cheese Shop Mysteries (Aames) if you’re into the genre of mostly-single-middle-aged-woman-who-owns-a-specialty-store-in-a-small-town-and-then-turns-into-a-detective. (Yes, this is a genre, that I read regularly. So does my Aunt, and my Grandma. It’s the best.)


  • Crossing the Chasm – Geoffrey Moore – I have to echo my trend of “finally” reading classics and then loving them. This year, this was it. The book was not at all what I was expecting, but I found myself frantically reading it on a bus in Iceland.
  • The Life-Changing Magic of Tidying Up – Marie Kondo – I know everyone loved this, but I did too.
  • American Icon: Alan Mulally and the Fight to Save Ford Motor Company – Bryce Hoffman – I grew up in Detroit, and all the newspapers were about the car companies. The boom/bust oil and American auto cycle was a big part of my environment. I really enjoyed hearing a story about how an industry can go wrong (and how to fix it).
  • A couple others: Ascent of Money (Ferguson) and The Feminine Mystique (Friedan) – highly recommend pairing with watching Mad Men.


By coincidence, I read 20 memoirs this year. I just realized that I’d done this, and I’m not sure why. Since it was 13.8% of my reading, I wanted to call out a few separately.

  • The Year of Magical Thinking – Joan Didion – Again, I prefer a classic. I can’t place exactly what’s so good about the style. I’m sure someone more literary could. I loved reading this.
  • M Train and Just Kids – Patti Smith – I’m grouping these together because I like to read things in a row. I did the same with Ann Patchett and Lucy Grealy last year.
  • Between the World and Me – Ta-Nehisi Coates – Again, everyone called this out this year. I don’t think I have much to add to the dialog surrounding it, but I do recommend reading it.
  • A couple others I’d recommend: Year of Yes (Rhimes), Just Mercy (Stevenson), Girl in Glass (Fei), Her (Parravani), The Empathy Exams (Jamison). I’d recommend Wild (Strayed), too, but that technically got in under the wire in December 2014.


I also want to call out some of the things I didn’t get done this year. I mentioned last year that we were in the preliminary stages with Wallace (an app for cheese enthusiasts) – we still haven’t finished, hopefully soon. We also toyed with the idea of a cocktail blog, but we didn’t do that this year either. We’re the worst wedding planners ever. Maybe this year.

Here’s to 2016.

Merging Product & Design at Lola

If you haven’t read it before, I previously discussed this topic in the PM-Designer tension.

For both of my previous jobs, “Product” was closely tied to Engineering. At Microsoft, we were part of the Engineering triad – PM, Dev, Test. At Kickstarter, Brett managed both the Engineers and the PMs. When I started at Lola, I was the only person working on Product (and I was the most “non-technical” person, so I slid over to fill those gaps).

Recently, we merged our Product and Design teams into one team. There are three of us, with overlapping skill sets. I cannot overstate how much this has helped us as a small team. By merging the groups together, we resolved most of the tension for who is responsible for what, and can better share the workload.

For example, up until our merge, I was responsible for roadmap creation across everything we were doing.

In the last couple weeks, we’ve been pushing very hard towards launch. My priority shifted towards working on our launch event, organizing usability tests, finding good friends & family users, triaging bugs, and answering last minute questions.

One of the designers came to me to ask about the roadmap after launch. “Ha,” I thought to myself, “no way do I have time for that right  now.” I am not proud of this, but I shut down the conversation by giving a long list of reasons that the imminent launch was more important than the roadmap. (Everyone will tell you that a great PM can think about the day to day and long term. I wish I could do that. I can think about both, but sometimes one takes the front seat. For me it’s about timing and prioritizing, not about having both things in your head at the same time).

When I went home to think about it that evening, I realized the reason the designer asked was because he did have bandwidth to do the work, and was interested in doing it. Even though “roadmap” had been a PM task, he was perfectly willing and able to help out while I hunkered down on launch.

So the next day, I apologized and asked the designer to take a stab at the roadmap – giving him the previous one as a skeleton. He had time, and he made one. It wasn’t exactly what I would have done, but it gave us a much better starting place. Since he did that work, we could sit down together and have the conversation – saving me time, and him having a greater impact on the roadmap.

Meanwhile, the other designer was sat with our iOS engineers, learning how to commit his own changes for copy, and triaging the polish and copy bugs.  Another task that could easily fall to be a PM or a Designer.

Of course, there are still tasks that are specialized. I’m more likely to coordinate between teams. The designers are more likely to do visual design (which I’m lousy at).

Before this experience, I would have said it was fine to be the first PM and work on a team alone. But, when the PM & Design teams are separate it’s tempting to split things by “who does what.” By putting PM & Design together, we’re able to learn from each other and help keep the workload consistent through the project.  Also get the added bonus of making sure the company is design driven. Design is involved from the beginning, which helps us make sure the roadmap is focused on what we’ve learned from user research.

This won’t scale. Eventually the team will be large enough that we’ll have to split. If you’re hiring your first PM (and won’t have another for a while) consider putting them with design.

Hearts, Stars, Thumbsup, Fav, Like, and Love – Reactions on the Internet

Kickstarter is the place where details matter. It’s about taking a lot of pride in your words, your iconography, and your work. It’s exactly the sort of place where you can get a month to research and obsess over a feature like “✭ Remind me*.”

And that’s exactly what I did the first month I was there.

After digging into how it, there wasn’t much consistency. Some people used it when they weren’t sure if they wanted to back a project yet, but didn’t want to forget about it. Others wanted it to reminded them of the impending credit card charge. The spectrum was wide. So wide, that it would have been reasonable to change everything: the icon, the name, what it did.

I’d forgotten about the project until I got back on Twitter yesterday.  The fav star replaced with a heart. The fav star had always been like ✭ Remind me – used for a huge variety of meanings.

When I was thinking about what to do with ✭ Remind me, I looked into other similar features.  Across the board, it doesn’t seem like most of these features were built with grandiose plans. That leads to a lack of consistency between them. I’ve dropped the verb tense from these for consistency. This data is mostly as of 2012, but I made some notes about changes that have happened.

I started out looking at Products that included a Star feature: 

1) Some used the ‘star’ as away to symbolize a bookmark (Chrome, Firefox). Safari used the book to symbolize the same thing. Now,  Slack also uses the star as a way to privately flag messages and get back to them.
2) Some used no name and/or ‘star’ as Kickstarter did. This was a bookmark functionality (Google Reader, Spotify).
3) Some used Favorite (Flickr, Android Contact Manager, iOS contacts, Google hangouts now also does this, Twitter was here). Favorite also implied “frequently used” or “something I want to get back to.”

This left the Star with a neutral-positive feel. It had an undertone of being able to “get back to something” or “find it again later.” It wasn’t always practical “get back to.”  Sometimes it was a sentimental “I don’t want to forget this.”

Then I looked at Products that included a Heart:

1) Love –, Vimeo
2) Like – Pinterest, Tumblr (Twitter is now here too)
3) Favorite – Etsy

The heart had a distinctly positive feel. It also was used in companies that had a strong community-feeling. Less corporate. This might sound weird in 2015, but it was almost on the edge of too personal/familiar.

I also quickly looked at (Thumbs) Up/Down:

1) Like – Facebook, YouTube
2) ThumbsUp (and Down) / Arrows – Reddit, Digg, HackerNews etc.

This was much more based on ranking and “quality” signals. These things fed into what the overall community saw, rather than a personal sentiment/tool.

Given these loose groupings, I don’t think the Twitter switch is surprising. It set a point of view on what the action is for, and encouraging that action. It aligns with the how the majority were using the feature. It’s not for ranking  and it’s not for bookmarking. It’s a way to express a sentiment to the community. The heart is definitely a distinct group from the star.

What interests me most is how this will continue to change. I think we’ll find three buckets.

1) Products that encourage one specific action that is desirable for the platform.

2) Products that encourage a variety of constrained reactions (Slack’s new emoji reactions).

3) Products that encourage the ambiguity to live on with the people on the platform. I think that’s where the next generation of innovations in “internet interactions.” Leaving a space open-ended let’s you see what else you can add – or come up with new paradigms for a product.

At the end of my research, I was tempted to push ✭ Remind me towards a specific goal. Instead, it lives on in ambiguity with minor improvements. I’m happy every time I use it, for whatever reason. It will never surprise me if Kickstarter remains the third type of product.

* ✭ Remind me, was a small feature that emailed a user 48 hours before the project ended.  The name betrayed the original purpose. It was “remind me to back this project.” Most people used it from the project page. Then it emailed a user 48 hours before the project ended so they could back it.**  Everything ‘starred’ was accumulated in a section of the profile called the ‘starred projects page.’ ***

** It sort of did this, with a lot of caveats. It only emailed you if you hadn’t already backed the project. If you starred the project within 48 hours of it ending, it still said “remind me,” but you’d already missed the reminder. It had previously provided any project updates in your ‘activity feed’ until the project was funded, but that was removed (upsetting some users).

*** Projects remained on the starred projects page after they’d ended, but you couldn’t do anything with them.


Giving Gendered Communication Feedback

I waste a lot of hours about people being wrong on the internet. I’ve decided that when I get annoyed about a gender-tech issue and can’t figure out how to respond, I’m going to provide a helpful (actionable) lesson instead. My hope is even if I can’t respond to everything that’s “wrong” I can at least give some more right things to do.

xkcd has it right.


Recently, my friends have started to take on leadership positions (whether formal or informal) at work.

From my male friends, I’ve started to get questions about how to give feedback to (often junior) female employees. Many of these things relate to interpersonal communication issues vs. say, code quality.

I think the most common two are:

1) How do I tell a woman to stop being self-deprecating about her accomplishments or abilities?
2) How do I tell a woman I work with that she uptalks during meetings, and I’m afraid it’s undermining her ability to be taken seriously?

The general sentiment is “I feel awkward” or “I know this might be gendered so I don’t know if I should say it.” In most cases, the woman deprecates herself, but then knocks every assignment out of the park. If she’s genuinely struggling with job content, that’s a different type of feedback (admittedly many of these suggestions still apply).

I’m the first to say that some of this feedback sub-ideal. We have a workplace culture built on very masculine communication styles. As Christina Xu has pointed out, we should worry less about “impostor syndrome” and more about blowhard syndrome. I agree.

Still, as long as I’m going to be here and working in this sort of culture, I want to at least know how my coworkers are perceiving what I do. Here’s a process to help yourself share possibly awkward feedback around communication styles:

Deciding to Give Feedback

(1) How would you feel if you didn’t give the feedback, and three years down the line it led to her not getting promoted?

It might be scary / uncomfortable for a few minutes or days to consider giving feedback, but think about the long term consequences for her career. This is not about you. Keeping this in mind will help keep you motivated to figure it out.

An early reader of this piece pointed out to me that, it’s also about the long term consequences. If you can’t give constructive feedback to a woman for a short period of time – how would you ever mentor a woman? Women won’t be able to achieve at the same level without having supporters who can give tough feedback.

(2) Are you the right person to give the feedback?

Sometimes, you shouldn’t give feedback at all. If a woman that you’ve never worked with gave a presentation to your team, you probably don’t need to be giving feedback. A good in depth discussion of this is in Lara Hogan’s piece on unsolicited criticism.

If this is someone you work with regularly, it’s appropriate to give the feedback. If you wouldn’t think twice about giving the same feedback to a male peer, you should figure out how to give the feedback. If you wouldn’t give the feedback to male peer – why do you want to give it to a female one?

(3) Have you given a mix of constructive and complimentary feedback so far?

I hate the shit sandwich (good thing, bad thing, good thing). It feels insincere and confusing.

It is important to give regular feedback. If this woman is someone you have worked with before – did you tell her when something was correct? (You shipped that feature really quickly! I thought your technical design doc was really concise/clear, etc). You should be doing this along the way to build rapport, and because both types of feedback are important.

If you do have a relationship and have provided work feedback before, it’s more appropriate to breach the gap and give constructive feedback.

If you haven’t done this, you can still give the constructive feedback. Just realize this issue so you can give more comprehensive feedback going forward.

(4) Is this the right time for the feedback?

The best time to give feedback is right after something occurs. If you haven’t provided the feedback one-on-one to give her a chance to improve, it’s probably a bad idea to dump it into her annual review (or annual peer reviews) with no context.

Giving Feedback & Following Up

(1) Ask first.

This is true for everyone, but it’s always good to start with “would now be a good time to give you some feedback on <X>?”

(2) If you think that “gender” is an elephant in the room, acknowledge it.

This might not legally be the best advice. I prefer when people do this, by far. If someone told me I was abrasive, I’d feel uncomfortable. If they told me they were aware of the double-standards for the word, I’d know that they’d sincerely reflected before talking to me, and had my best interest at heart.

Compare “you were abrasive in that meeting” to: “I think you were a little too forceful in the last meeting. I know there’s research that women are judged more harshly for this, but I felt like your response to Y in particular was harsh. I know you didn’t mean it to come off that way. I think you could have improved the communication by doing A, B, or C. I don’t want you to jeopardize your relationship with Y.”

(3) If you aren’t comfortable with acknowledging gender up front, at least respond if she brings it up.

Early in my career, my manager always expected me to take notes in meetings. I wasn’t sure if this was due to my gender or my (lack of) seniority, and a senior woman that I worked with expressed the same concern.

She ended up encouraging me to ask him, so I did. We ended up having a great conversation, and he explained he’d never realized I might feel that way. It turned out he felt that being the person taking the notes helped with team status, and with gaining future responsibility. A few years later: yeah, he was right. I always try to take notes in meetings, and it’s value to me greatly outweighs any “gendered” nature of the work.

(This isn’t true for everyone – I happen to like taking notes, and have good comprehension while doing so).

(4) Figure out how you can actually help going forward.

If the woman acknowledges its an issue, or expresses a challenge, figure out how you can help in the future. Giving the feedback isn’t the end of the road.

Be sure to ask her for this – “do you want me to point it out if I see this again?” can go along way, as can “do you want to do a dry run of your presentation with me next time?”

The same sort of things you’d do for any coworker who needed help on a specific skill.

Thanks to Sharee Loeffler, Meagan Gamache and Cedric Hurst for reading an early version of this piece and providing some improvements/clarifications in my thought.

Dropping Out – A Beginner’s Guide

x-posted from Medium.

In technology, there’s always lots of buzz around “dropping out.”

After all, lots of high profile people have done so — Bill Gates, Mark Zuckerberg, Alexa von Tobel. Peter Thiel encourages people to drop out with the Thiel Fellowship. Tess Rinearson wrote a thoughtful piece on what a “dropout” is supposed to look like — and how most of us don’t fit that mold. (I do not look like that).

This is not what dropping out used to be. It’s rarely about leaving high school. It’s definitely not about your parents needing you to work and support the household. It’s not about having a child, but no childcare.

It’s a new, optional, trendy type — and only available to a few people. The media likes to glamorize it. It turns out that even this type of dropping out is not as cool as it seems, and it’s not as big of a deal as most people think.

I’ve done it twice, and went back to school once. The first time, I left Olin College after my second year of undergrad to have a startup with friends. It failed, and I went back and finished in one more year. Because my college experience was “four years” (three of college, one of dropping out) people rarely realize it even happened. This time, I’ve left HBS after one year to work at Blade Travel. I have the option to go back anytime in the next five.

No one thinks I am cooler for dropping out.

Defining User Needs for our failed startup.

If you are considering doing the same, here are five things to consider:

(1) If you are dropping out because it’s trendy, you are doing the wrong thing.

I cannot say this enough. The “dropout” status does not matter.

People think it’s important because the common belief is that education needs to be linear. It isn’t. One of the courses I got the most value out of was an information design course at UW (HCDE511). It isn’t part of a degree, a certificate, or anything else I have done. Likewise, there are engineering classes I got very little out of that count towards my degree.

Learning doesn’t happen in formal degrees — it happens in experiences. I believe overtime the world will shift to align with this idea.

In the meantime, the people who believe unconditionally in the current system think you can’t drop out. They are wrong. It’s about a calculation of risk and benefit.

The people who think it’s better to drop out believe that it’s always better to flaunt the system. Flaunting the system is not equally available to everyone, and they are also wrong.

Dropping out is not about what other people around you think you should do. It is about what is best for you. It is not a decision by committee. You should know what you’re hoping to achieve by dropping out. If you do decide to drop you, you need to make that decision alone.

(2) The best thing you can do when you drop out is “go on leave.”

People seem to think there’s a huge difference between “being on leave” and “dropping out.” In either case, you stop going to class and stop getting resources based on your educational institution.

Fuck the people who tell you it’s not really dropping out. They usually haven’t done either and have no way to know. Leave gives you option value. If what you dropped out for goes really well, that’s great, and you continue being on leave until it expires — and drop out forever. If it doesn’t, you can still go back. There’s no glory in closing a door when you don’t need to.

The number of hoops you have to go through depends on the institution — at Olin I remember it being quite a bit of work. At HBS I just emailed one PDF. If possible, I will aways recommend starting your drop out process by going on leave.

(3) Seriously, you need health insurance.

Figure out your health insurance before you commit to dropping out. I wasn’t too worried about it the first time (I was 20 and healthy), but my parents insisted. With the wisdom of more time, I’m glad they did.

If you’re taking a full-time job, you should get benefits, including insurance. Hooray!

If you’re under-26, figure out how to stay on your parent’s insurance (if they can let you). The rules were different when I did that the first time, but my parents helped me figure out a way to make it work.

If that’s not an option, and it wasn’t for some of my friends, in certain states there are specific, inexpensive plans for young people. We were in Massachusetts.

Another way, if you have one, is through a partner. For example, at many technology firms you can get “opposite-sex domestic partner insurance.” Tom has allowed me to be on his insurance twice so I could pursue the career options I wanted.

These are the things I’ve found, but I am sure there are more. It isn’t worth dealing with the hassle after you’ve committed.

4) Think about your finances.

Another big consideration is finances — both yours, and if you’ll be working and living with others — theirs.

In the winter we turned the heat down low to save money, and our dryer routinely set clothes on fire.

The first time I dropped out, there was a group of six of us. Three had relative financial support (parents, savings) and three did not. We were working on a startup, and had no income. It caused a lot of tension. We had a lot of conversations you wouldn’t expect:

Who cleans the bathroom? Is that a household contribution that helps alleviate financial burden? Does a Swiffer qualify as a necessity? When is it okay to deviate from the typical grocery list? How warm can we keep the house?

The practical tension was detrimental to us working together on what we really cared about: the company we wanted to start.

Figure out how much money you’ll need for a year and how to budget it. This sounds obvious, but if you’ve never lived on your own before (like if you’re in a dorm and on a meal plan) — you want to think carefully about it.

On top of that, look into your student loans. Will you have to start paying them back if you drop out? How will you go about doing it?

5) The “fun” part comes last.

If you don’t have the patience to deal with the logistical side of dropping out, you also won’t have the patience for the day-to-day of dropping out. There’s a lot of stuff that isn’t glamorous.

That said, once you do get the logistics right, solidify the fun part:

Brainstorming for what we wanted to start.

What do you want to work on?

How do you work best?

Where do you work best?

What are your goals for this year? Next year?

What are the different things you may try?

What can you do with this freedom that you couldn’t do while in class?

The first time I dropped out I wrote a 20 page document detailing everything I wanted to do. I probably did half of it, but was grateful I’d created a plan. This time it is a lot more like returning to my working life before HBS.

Regardless, know what your goals are. If you do decide to take the plunge…

Good luck!

Dropped out? Have a different story? Think about this differently? Please write a response!

The Three Skills of a Google Product Manager

One of the things I’ve picked up on over the course my career is just how much respect there is for Google Product Managers. I don’t disagree – some of my favorite PMs have worked there. On the other hand, many of the people I really respect haven’t. So what’s the difference between a Product Manager (PM) who worked at Google, and one who hasn’t?

I’ve been asking around. Last time I was in San Francisco, I had the chance to ask Ken Norton and he clarified it for me in a way that I wanted to share. This explanation aligns with what I’ve heard from other friends (internal and external perception) – but it was by far the best framing I’ve heard.

(0) Google helped standardize “Product Management.”

I’ve written about this before – but the origins of Product Management are nebulous. It stems from Brand Management and Program Management. Google was one of the companies in the valley who had an established discipline first. This means they set some of the standards for what we want the discipline to be. This isn’t really a difference now that it’s spread, but it is important context.

(1) Technical Respect

This has been talked about frequently, but Google is an Engineering-led culture. This means you can’t get things done if you don’t have the respect of Engineers. Having had a Google PM job for a significant chunk of time means you did figure out how to achieve this.

If you are somewhere that engineers “have” to do what you say, you haven’t achieved this.

(2) Scope

Google does not scope projects to PM-experience. Even APMs are thrown into large areas. This is different from many companies who don’t want the “risk” of having a new PM own something large. This is also different from political companies where there isn’t enough work, so there’s political infighting to “own” things.

This resonates strongly with me – at Microsoft my first project was an app where you couldn’t do anything. You just clicked a link, and it showed you PowerPoint slides.*

(3) Accountability

When you have the privilege of owning a large area, you also have to be accountable for it. That means it has to either work – or that you dealt with the consequences when it didn’t.

Some organizations will say everyone is at fault when something goes wrong. At Google it’s more likely to be specifically the PM.

I’ve seen this happen in small teams where “we’re all in this together” and people don’t want to offend each other.

I think these are three great areas to evaluate a PM on, but the only way to learn them isn’t at Google. (And while you have a great shot of learning them at Google, I do know those who haven’t).

If you’re a PM and you haven’t mastered these three skills, it’s well worth figuring out how to change your role to include them.
* To be fair, the scope of this project was originally larger. Even so, my next project had far more PMs than were necessary. Too many PMs means a lot of time in meetings with other PMs, not enough time getting things done.

You are not your culture

Over the weekend, Jodi Kantor and David Streitfelt published a piece on the culture at Amazon.

I’ve seen responses fall in three primary categories:

1) The necessity / truth in this reporting, and the need to create better conditions.
2) The idea that this isn’t true (anymore) or the story is sensationalist.
3) The idea that even if this is true, an extreme environment is necessary to do amazing work.

One of the key topics in the piece is about how forceful and direct the feedback culture is. Doing great work does require constructive feedback. Ben covered this nicely in Stratechery (paid, and highly recommended).

He particularly drew from this New Yorker article, and in particular this passage:

Jobs replied, “Why would you be vague?,” arguing that ambiguity was a form of selfishness: “You don’t care about how they feel! You’re being vain, you want them to like you.” Ive was furious, but came to agree. “It’s really demeaning to think that, in this deep desire to be liked, you’ve compromised giving clear, unambiguous feedback,” he said.

From what I can tell (article aside), Amazon does have a culture that encourages constructive and clear feedback on work. This is not surprising. That’s been true everywhere I worked. I receive and give feedback for Blade Travel every day. People who work in technology often defend the right to give clear and constructive feedback on work – preferably absent of politics.

So if we are so defensive of our right to give blunt feedback on products – why can’t we do the same with culture?

“Culture” is where we still struggle with the distinction between “critiquing my work” and “critiquing me.”

When I started my career as a PM it was hard to separate “critiquing my spec” and “critiquing me.” (You can easily substitute code/design for “spec” here). It felt like every constructive comment was something I should have seen in advance. I cried more than once after spec reviews. Like most, with more experience, I moved away from that.

Cultural critique is a more abstract version of the same concept. We have a harder time with it. It’s because we talk so much about how founders set the culture for the company. Yes, founders do help create the culture. Founders are not the culture. Jeff Bezos is not Amazon’s culture.

If the NYT published a piece talking about how the Echo was “the most useless product ever” we would not have reacted as vehemently. We would have used it as a jumping off point for the conversation about the product and how it will improve, and where it will go. It would not have been right/wrong or good/bad. It would not have felt so personal.

To build better companies, we need to get there. We need to accept that Amazon’s culture is something that can be critiqued – the same way a product can be critiqued.

It is not personal, even if it feels that way right now.

Riding the Subway

When I lived in NYC, I started suddenly seeing Tumblrs about people (mostly men) taking up too much space on the subway. Here’s one as an example.

Many of these cases show trains with plenty of space. While it’s still an expression of privilege, it has fewer practical implications if there are plenty of open seats on the train.

Unfortunately, in Boston, I frequently see this when the train is packed (even with people still waiting on the platform). In those cases an empty seat is one less person who gets on the train. Or it’s one more person crammed into the packed standing area, when there’s a seat available. For some reason, people here are too polite to sit down and force the person to make room. I assume some of the men taking up too much space don’t realize they are doing so.

I often see women look at the seat, evaluate if they think the man will move, and then walk and stand at the other side of the car – leaving that one open. Once one person has deemed it “un-sittable” no one else seems to either.

So, I’ve been sitting in all of those seats. Even when I don’t really want to sit. I don’t say anything – I just reclaim the space to make it obvious the train is full. I’ll happily offer the seat to someone elderly or pregnant after I’ve reclaimed it.

Today was one of those days. I was on a crowded train. There was a man taking up about 1.5 seats worth of space. I watched a woman walk up, look like she was going to sit down, and when he didn’t adjust to make space – walk to the back of the car to get another seat.

So I did my usual. I sat down.

The man didn’t move, or make any adjustments to provide me with more space. Instead, he left his elbow on my thigh for the entire ride. The subway is crowded – often your arm will touch another arm, your leg another leg. This wasn’t that. He left his elbow on my thigh.

I couldn’t bring myself to say anything – or figure out what to say – so I just sat there for four more stops until I got to work. This is the first time my strategy has backfired, and I’ve been doing it for about a year. I’m going to keep doing it, but I sure hope that doesn’t happen again.

“But you don’t look like…”

When I announced I was going to HBS last Spring, one of the common reactions was, “wow, the old boy’s club?” or “so.. you’re trying to find a place more sexist than tech?” I think this was particularly prevalent because of an article that came out at the time.

Transitioning to HBS was anything but easy. I was an introvert in a very social environment, and I was technical in a place where many things are high level. Many things were extremely hard for me. But at least one thing was finally easy, and that was my gender. The HBS classroom is 42% women.

Since I’m sure someone will ask: HBS has things to fix on this front, but it feels light-years ahead of tech. There was one thing in particular that stood out.

When I talk with people in technology, it’s frequently assumed that I don’t belong. People ask me “are you a recruiter?” with alarming frequency. People will ask me if I’m at a technical event because my boyfriend is. It’s not uncommon for someone to say “but you don’t look like an engineer” or give me the look that says exactly the same thing. I haven’t been mistaken for a janitor, but nearly half of black and Latina women in science have.

It was a delight that this didn’t ever happen at HBS. At HBS, a common first question is “what section are you in?” – assuming you are a student. No one ever asks me “are you a partner?”

People don’t assume what job you did before, either. You cannot, and do not, look “like a consultant” or “like a banker” or “like an engineer.” Instead, they’ll ask “what do you do?”

This was a delight, and it should not have been. It’s basic courtesy to not assume you know someone’s job based on how they look. Just as someone does not look like a banker or a consultant, they also do not look like an engineer or a recruiter.

There is nothing wrong with being a recruiter. There is something very wrong with assuming someone is a recruiter just because they’re 5’4” and have long brown hair. If you stop and think for even one minute, it’s absurd to presume to know someone’s job based on their appearance.

People try to play this down and say “it’s a compliment!”
It seems like not that big of a deal.

At points in my writings about technology, I have worried about being “too sensitive.” At points, I have wondered if micro-aggressions really matter. I have wondered if it was like this everywhere, and there was no specific problem.

But I have now been elsewhere, and this is not a compliment. It is a big deal. It doesn’t make any sense. It’s rude.

These small insinuations and questions betray huge assumptions. That the only women working in technology are non-technical. That there aren’t women in technology at all.

Each time you’re asked these small questions, you’re forced to be an ambassador: correcting the assumption, proving we belong, proving you know what you’re talking about. You no longer get to speak for yourself because you have to speak for the group.

It is exhausting to have to deal with this over and over: striking the right balance of being polite, while explaining the asker has been impolite. Trying to save the next person from the same experience. Trying to change the perception, one person at a time. Even when only one person in an event with fifty asks the question – you know that someone else is thinking the same thing. It reminds you that you’re constantly being judged in a way you didn’t sign up for, and that others see you as not “belonging.”

All because of stupid questions. Rather than having women deal with this, we should all learn:

1) Don’t be presumptuous. If you want to know what someone does, say “what do you do?”
2) For extra credit, follow up with Paul Ford’s handy primer on being polite.

At HBS my opinion still had connotations: “technical” and “startup” and “blunt” – but that’s because those things are me, and they are the things I choose to represent.

I hope that someday women in technology are granted the same relief that I had this year. I hope that some day I comment and the first things people think are “consumer product management” and “artistic process” and even “MBA.” That people will judge those categories instead of my gender.

Until then the “old boy’s club” will feel more inclusive. Watching what questions we ask will be a start.