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Finding the Right Fit as a Product Manager

Alignment
Product Team
Company Culture
Hiring
Strategy

11 October, 2021

Andrew Tsui
Andrew Tsui

Director of Product at K Health

Andrew Tsui, Product Leader at Sailthru, discusses his approach to searching for the right Product role, while disclosing his rubric of the top interviewee questions that help him make the best decision.

Problem

During my last job search, I talked with 45 different companies and attended 135 interviews altogether. I realized that many companies want to hire product managers partly because this is an extremely talented bunch of folks, who are likely able to perform a wide range of functions, and might be tapped in cases where an employer simply hasn't defined what they're looking for with precision.

If you're reading this, you might have experienced some of the following:

  • You might be confused with a Project Manager or a Scrum Master or Agile Coach, where you're asked a lot about execution, communications, agile techniques,

  • You might be confused with a Product Owner, which is less customer-facing and user-centric due to the nature of engaging deeply with the team,

  • You might be confused with a Business Analyst, where strategy is more of a theory, while your day-to-day might be mostly limited to requirements documentation and executing in a waterfall environment,

  • And plenty more confusions!

So, let's start with a definition: a Product Manager owns the strategy and decision authority for a product area in order to find and maintain market-product fit. They are a delegate of the company's leadership to resolve disparate points of view and grow the product's revenue and/or profit.

And, the following 11 questions will help you, the interviewee, find companies aligned with this definition.

Actions taken

I began my job search by casting a wide net and asking very pointed questions. An old colleague would say, "let's not faff about eh?" and I absolutely agree! Interviewing is a two-way street, an opportunity to ask hard questions just like your potential employer would have done up to that point.

Here's a great question to start off with for the hiring manager: speaking of [a large recent feature or product release that was press-worthy which you looked up ahead of time], did you lead the release, and how did that go? The answer reveals a lot about the company's inner dynamics. Seek out opportunities where equal weight is balanced between design, product, and engineering, where the "squad" makes decisions independently or autonomously in the service of clearly defined goals or objectives instead of getting stuck on specific names.

The rubric that I cover in the following sections is designed for individual contributors with plenty of questions on each topic to consider. There are four topics in total: technology and tech-related practices, business aptitude and dynamics, product and user experience tilt, and company culture. Find the questions you're comfortable asking about, and consider the interviewer's answers thoroughly.

Regarding technology and tech-related practices, I start with the following: how frequently do releases happen, and how do they get evaluated later? How does engineering, product, and design collaborate? How is tech debt tackled? What tools are used for instrumentation, analytics, monitoring, or the like, and how are they used in the organization? The types of answers that are good indicators ought to align with your personal style, whether you're adept with technical topics, with numbers, and your decision-making processes. In a way, you'll want to see if these answers "fit you well."

To assess the business aptitude and dynamics of a company, I would cover off: how does the business share information with the product team (i.e. sales figures, user growth metrics, churn rate, subscription or LTV measures) or any metrics related to the industry? The level of transparency is generally evident in the answer, and that's an important gauge for your ability to contribute as well as the company's culture. I also press upon how the company's Product/Design/Engineering teams tend to work: how often is the team asked to hit a date (customer escalations, urgent issues, or the like), as opposed to focusing on iteration? If the company tendency is frequently to hit a date, it is likely that the team's scope is small or perhaps too discrete, or else their team is at risk of overwork. Either way, it's not a healthy situation. If the company is focused on iteration, de-risking, and structuring learnings together to inform larger builds, that might be a better fit for you.

The third set of questions covers product aptitude. An easy question to start off with would be: how does the product team typically communicate updates and ideas to the entire company? This helps you determine the organization's style and discipline about communications and their standing in the organization. Of course, you should ask for an overview of the teams' roadmap for the next six months. The answer to this question should align with your interest in the kinds of problems you want to solve, offer room for growth regarding strategic decisions, and the kind of company direction that would guide your actions. Product managers ought to have a good deal of latitude to come into an organization and spend a very good chunk of their time with strategic opportunities (build-measure-learn), and so the six-month roadmap shouldn't sound or feel like a two-year backlog. The other product aptitude question I like to ask is about strategy and strategic decision-making. Ask about the last time that there was rigorous debate about the direction of the product: what were the choices, and pros and cons? This is a great way to suss out Horizon 1 thinking versus 2 or 3. I expect it will illuminate how you should expect to operate in the day-to-day.

Lastly, consider the company culture carefully. I like to ask for examples of challenging situations that the team had to deal with, something like: when was the last time your team had a spirited disagreement about the direction of the team or the roadmap? The emotional depth of that challenge speaks volumes about the company's culture. If they are facing tough challenges, it may be a great recipe for innovation. If they are facing highly emotional challenges, it may not be a mature company to join. One of my mentors gave me a great prompt that I'll close with: when it is OK for me to make decisions that you (the hiring manager) disagree with? A hard question to mull over and an incredible thought-starter for Product Managers at any level.

Lessons learned

  • Product Managers have a vast array of criteria to consider in the job market. Consider de-emphasizing compensation, and try to surface the mindset of the company and how they work, using these questions that product manager interviewees should ask. There are benefits to your well-being and career success that might overshadow the dollar figures.
  • If you're invested in adding to your skill set, look for situations and companies where you'll have the opportunity to develop something press-release worthy or to discover or invent something. Many of the questions and prompts above will help you with your search.
  • You ought to ask these questions if you're looking for a long-term home. A Product Manager that can work with a company for more than four years will have a huge impact on the company and on their own career. Otherwise, you'll miss out on the organic growth that will supercharge your future.

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