What to Ask When Interviewing for a Product Management Job

Dec 4

Background

If you are looking for a new role in product management you should be trying to organize your search and spend some time mapping out what is most important to you in your next role. Once you’ve landed an interview you should be coming in with a long shopping list of the information you need to collect to make the best decision possible about whether to join this company. Given the unique role of Product it’s critical that you get a solid understanding of how the company operates and whether it is set up for you to do great things, or if you will spend your energy overcoming organizational issues. It doesn’t matter how many companies you get interviews with - treat every interaction with a prospective employer as an equal exchange of information. You’re trying to learn as much about them as they are about you.

This is not a natural motion for most people during interviews. We are usually so excited to get an interview, especially with a company we are interested in, that we spend 100% of the prep time researching, practicing responses to possible questions and getting ready for what they will ask us. Good candidates will typically ask a few good questions during interviews, but honestly you should have more questions than you can possibly get answered across all of your interviews.

What Are You Searching For?

There are a couple of broad categories of information you are looking to collect during interviews:

From my own firsthand experience, anecdotes from friends , and interviewing people who were trying to escape a “sub-optimal” situation, the reasons for the company struggling, or the role of product manager being extra challenging, usually fall into a problem in one of these three categories. Focusing on these categories will help you a) generally learn a lot about what your day-to-day will look like in the role more effectively than asking “what’s the day-to-day look like” and b) highlight red flags that may be a reason to reconsider.

Of course you should also be looking at whether the company is financially healthy, growing, well-regarded by customers, has a strong management, team etc. This framework is designed to compliment those more generic questions you should ask about the company by filling in critical areas of information you need to know when considering a product management role.

The goal here is very much to have as complete a picture as possible before you make a decision. Everyone has to make a personal decision about what they are willing to take on based on many variables that are unique to their situation. A company that is not growing super fast but gives you an amazing opportunity to gain experience or get into an industry you are interested in may be worth it. Rocket ships can be a little messy on the inside (from all the acceleration), but maybe that’s worth it to be a part of rapidly scaling something. No company is perfect, every place you work will have things that are great and things you wish worked differently.

There are however some situations where you may spend most of your effort just overcoming organizational friction - strategic or interpersonal. That’s where the red flags come, that’s where you want to pause. I think most product managers I know would be happy working insane hours on something they are excited about with a team that is equally fired up to make something great come to life. The most soul-zapping thing in the world is feeling like you are working yourself to death to keep people aligned just long enough to deliver the first part of something. Constantly having to reset your efforts and team due to tops-down strategic or organizational changes. Being locked in endless loop conversations with coworkers when it appears everyone can disagree but no one has the authority to move forward. This framework will help you avoid these situations, or at a minimum help you see what you are getting into.

Strategic Alignment and Communications

Broadly summarizing over 50 years of literature on strategy (cough, sorry), let’s say for the sake of argument the following things are true:

Strategy is a set of choices - where to play and equally important where not to play (basically, strategy = focus)
You should be playing to win, not just to collect a participation trophy - are they taking big enough swings to get to and maintain a market leadership position?
Having one or a few extremely well defined customer segments is better than not being able to articulate who you are solving for and being aware of their most urgent problems
Strategy should be flexible and evolve over time, but should not be adjusted on a monthly or quarterly basis
There should be some business metrics or KPIs that measure progress towards the goal

While a bad strategy executed perfectly will likely still lead you into a ditch, it seems like most companies tend to have fairly good strategic direction, and fall down in execution. This comes in part from only having a high level strategy statement or vision, maybe a roadmap, and none of the connective tissue and hard conversations to link direction to execution in any structured way. Have they shown the discipline to map out a strategy and lay out some measurable objectives? Does each function know what it means for them? Is everyone in the company paddling in the same direction?

During the interview process you should be trying to figure out how true each of these statements are for the prospective employer. For this particular set of questions, I’d say you should try to ask the same questions to everyone you interview with. See how similar the answers are from person to person. Senior leaders vs ICs. Across functions. Do they have answers and are they the same? Having a solid strategy and plan is only effective if everyone knows about it. Make sure that they not only have a solid plan, but that it’s being effectively communicated to all employees at all levels.

Product management is a job that requires making a lot of decisions on a daily basis. If the strategy is clear, employees across the company understand the target customer, and everyone at the company is on the same page with the same metrics, life is WAY easier and making decisions is much simpler. As you start to see missing answers or lots of variance between individuals, that's a signal that the role may face some of the “bad friction” of constantly trying to keep people on the same page.

Product Team Fundamentals

The definition of product manager varies widely from company to company, as does the role of the Product org within the company, so it’s critical that you understand these components before making your decision. Additionally you want to do a quick “sniff test” to see if there is the appropriate best practices in place related to key aspects of doing the job.

Role and Position of the Product Function

The first question is simply where Product sits in the org and whether it’s a leading organization or support organization. In most modern product-focused companies, it’s typical to see the leader of the product organization report directly to the CEO. Sometimes that’s a CPO, sometimes a VP, sometimes “Head of Product” - the title does not matter so much as a seat at the table and the recognition that Product is important enough to a separate function with its own voice in the executive team.

Not that this is an immediate red flag, but you will sometimes see Product and Engineering report to a single combined leader who reports to the CEO. You can luck out and get an awesome human being in that role that is able to effectively lead both orgs. I’ve seen that, but it’s rare. It’s much more common for that person to be a career engineering leader with little to no experience in the role of product management who “adopts” the smaller product team. This setup will tend correlate with an “engineering led culture” - depending on the product, target market, and leaders this may or may not be a reason to reconsider the role.

Product and Engineering are different jobs and leading these organizations requires different skills. I’ve found it to be challenging for product managers to achieve the level of leadership in the business necessary to be very effective when Product does not have a separate senior leader and is tucked in under engineering. Furthermore, if you really want to move up in the function and learn from your team, you want to try to find a place with several senior product leaders with lots of years in the job who you can learn from.

What are Product Managers Doing Exactly?

Given the variability of what people with the title “product manager” do from company to company it’s really crucial to know what you are signing up for. Again, there’s not really a “wrong” answer unless PMs are doing something that is obviously not a normal part of the job. This is for you to ascertain whether the role is what you think it is, whether it lines up with your skills, and will help you to grow.

Most of the variability is around “inbound vs outbound.” Do product managers spend most or all of their time interfacing with engineering or are they working cross functionally with sales, marketing, support and others within the business? If you are just starting out, a more engineering / agile team focused role to teach you the ropes of building out features and testing is probably great. If it’s a more senior role, you’re going to want to look for something that offers more exposure and opportunities to lead across the business.

Also be on the lookout for “project manager” roles labeled as product manager. There is of course always some element of project management required to be a PM, however Project Manager titles are a different job. Sometimes a Product Management role can actually turn out to be more Program Manager or even Product Marketing Manager. The key thing is to get past the title and find out what the responsibilities, day-to-day activities, and exposure look like. If you’re frequently interacting with customers, setting development priority, and working cross-functionally to successfully hit your goals and grow the business, then you’re a product manager, regardless of the title.

Product Best Practices

I’m sure I’ll get plenty of comments about how there have been lots of companies that were successful without following “the textbook” of Product Management. There are of course examples of companies that nailed product/market fit so well that they’ve been successful almost in spite of themselves. There are many more companies that are somewhere in the middle - not growing like crazy and not obvious trying to follow or avoid best practices. If you randomly sample a selection of companies that are growing and well-regarded by their customers, I’d be willing to bet a majority of them are following many of the best practices below. The important thing here is to see whether the product team has a few core behaviors in place that will set you and the company up for long term success.

Basically, ask all of these questions…

Frequent Customer Contact - Are all of the members of the product team speaking with customers on a regular, ideally weekly, basis?
Ongoing Discovery (not Validation) - Do they engage in true discovery conversations where they are talking to users about the general problem space and getting to the root of problems.
Goals - Is the product team focused on outcomes not output and use goals and metrics to assess success?
Analytics - Are the products well instrumented and the product team has good visibility into how the current products are being used at a granular level?
User Testing & Validation - Are concepts and designs validated with customers before development starts?

If you get a “yes” to 4 or 5 of those, then it’s a pretty well run shop. If you get 3 or fewer, then you have to question the validity overall product direction and the tactical prioritization of features in any particular backlog. If you’re not continuously engaging with customers then you are not customer centric. Articulating goals and metrics is hard and can be intimidating, but it shows maturity in the organization and accountability. Analytics and data give you a baseline to understand current behaviors and trends in a quantitative way that should be the starting point for any product decision. Showing designs to real users, even not that many, and not that formally, can de-risk so many gotchas that pop up when development starts or worse, post-release. If you want to do the job of product manager close to the correct way, and have the best chance to have an impact and advance your career, you want to land in an environment that reinforces the right behaviors and ideally where you can learn the cutting edge.

Interactions with Key Functions

The last element you want to explore during your interviews is how healthy the relationship is between product management and other key functions in the business, specifically engineering. Even if it’s a more outbound role you’re still going to spend more time with engineering than any other function at the company. How big are the various engineering teams or squads? How many squads or does a PM typically work with? Most importantly, you want to see if it’s normal at this company to have a very collaborative relationship between a product manager and their engineering lead(s). In the best situations you don’t feel the need to set that many regular meetings because the two of you talk all the time about multiple projects ranging from early concepts to things that were released 3 weeks ago. You are partners that work together throughout the development lifecycle.

In terms of other functions it can vary a bit, but more than anything you’re looking for an active relationship with regular interactions. Whether it’s sales, marketing, support, operations, finance, legal, etc you want to figure out if the product team has some level of established, healthy relationship with each of these teams. If you’re lucky there are established communication channels, metrics, and meetings that already exist to ensure effective information sharing across these teams.

Summary

Treat your interviews as much as an information gathering opportunity for you as it is for your prospective employer. You of course need to do a great job answering the questions asked of you, but you are also making a big life decision and need to gather the best quality inputs possible before doing so. Do your company research, try to answer as many of these questions as you can from the outside, then prioritize your remaining list based on the size of the potential impact to your decision.

As a quick aside I’d mention that you should also be trying to do as much as possible to figure out whether your direct manager is someone you’re excited to work for and learn from. While not specific to product management, bad bosses are typically one of top if not the top reason people leave companies even when it’s an awesome company that pays well. See where else they’ve worked and try to get references on them from current and former employees and colleagues. Ask for additional time to speak with them if you feel you didn’t get enough during the interviews. You can follow everything in this article and get all positive signs in these categories, however if your potential manager is toxic that can eventually outweigh everything else.

Remember there is no right answer, only the risk of making a decision based on less than a full picture of the current state of the company. Do the personal fulfillment, financial, and career upsides outweigh some of the potential strategic, operational, and inter-team issues you might need to overcome?

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