guest blogger product management

Ask the Right Product Questions

Guest Post by: Gregory Rakovsky (Mentee, Session 10, The Product Mentor) [Paired with Mentor, Nis Frome]

Finding the right product management job can be tough, as product management is a multi-faceted discipline that doesn’t lend itself well to classification. Regardless of title, be it Product Owner, Product Manager, or some other fanciful title, what a product person does in one organization may not be the same thing he or she does in another. Some organizations lean toward execution, with a focus on product artifacts like PRDs, user stories, and roadmaps. Others focus on UX, emphasizing wireframes and user flows. While still others may focus on data analysis, customer research, project management, or even engineering.

When deciding to pursue a new opportunity, it’s important to understand the product organization within your potential employer, and then look deep inside yourself to understand if your interests and strengths fit those needs. That means taking the time during the interview process not only to answer hard questions, but also ask some!

What is the employer looking for?

A company that practices aspirational product management is one that values experimentation and customer research, and continuously integrates those learnings into the product development process to create a valuable product. Alternatively, some companies are execution driven and hire product managers to push an idea through the development life cycle without worrying too much if there is inherent user value. This is indicative of a company that really should be looking for project managers who can at times do some customer discovery, rather than product managers who can at times do project management.

Below is a list of questions you can ask the hiring manager and existing product team members throughout the interview process. Their answers will inform you about their current processes, how mature their product management process is, and what type of product manager (if even one at all) they’re looking for:

Where do new ideas come from?
An answer like “from management” or high level stakeholder may mean that ideas are decided ahead of time. As a PM there, you will most likely be ironing out the details and executing on the small stuff without having much input into larger strategic decisions. Look for a response like “From any part of the organization and customer discovery”. Don’t be afraid to follow up asking for concrete examples of a feature that backs up the response.

Do you experiment with new ideas and how?
Many companies conduct NO experimentation at all. They release to production to see for the first time how customers react. This is obviously a red flag as there is no opportunity to de-risk product decisions. A company that does it right will have lots of experimentation built into the development process. Examples include: speaking with users and internal stakeholders early, showing rough wireframes, creating prototypes before any code is written, having functionality demos after every sprint, and A/B testing various versions of a given feature.

How far ahead is your roadmap determined?
A roadmap determined too far ahead of time infers a rigid product organization, with little opportunity to incorporate learning and experimentation. Look for a defined roadmap that allows for modification and pivots along the way.

How often do you speak to users?
An organization that constantly keeps in touch with it’s users is one that can act quickly and adapt to changing wants and needs. As a strategic decision maker, having continuous conversations with users is your competitive advantage.

What is the user lifecycle?
How long do users stick around? The average retention of a user is important because it determines how long you will have to dig deep and understand problems. If users are constantly churning, you have less time to create relationships and dive into their needs and wants. Sometimes it takes a while to get into a user’s head to create value.

How engaged is the user?
How critical is this product to the client’s day to day? Do they use it daily and rely it on it to get their work done? Is it a “nice to have” that they use sparingly? If a product is rarely used you will have a hard time connecting with users and getting deep into their needs. If a product is critical to the user’s day to day, they will be more heavily invested in making sure it continues to become more valuable over time and be more likely to partner with Product in that process.

How often do you speak with engineering and design?
Ideally, the answer is “anytime you want”. An answer that alludes to a staged approach implies a waterfall methodology which is not ideal for building great products that are validated and de-risked.

How is the performance of a PM measured?
Does the organization set company, department, and personal OKRs? A good OKR is one that holds someone accountable while also giving them room to pivot. The nature of good product development is fluid, so goals must have some wiggle room. Also, good OKRs should be stakeholder focused (internal or external) on metrics like engagement, ease of use, and overall satisfaction which in turn drive top line numbers like revenue and retention. A vanity OKR is one that is output driven –  “How many PRDs” did a PM complete in a given time.

Know Thyself

As a candidate, you can already tell which activities motivate and inspire you, which activities are just ok, and what you dread doing. So it’s important to understand how your interests, strengths, and weaknesses align with an employer’s expectations. While no job will allow you to do only the things you want, you can make sure that the majority of your time is spent on energizing work.

So what do you gravitate to?  

Do you enjoy communicating a product vision, and the whys behind your product decisions?
Make sure the company allows for lots of user interaction via presentations, feedback calls, user groups, and webinars. Beware if the company has a rigid multi-department process to get access to users.

Do you enjoy working on long term strategy?
Make sure there’s a research component involved and time to boil down findings into recommendations. Access to key decision makers is critical.

Do you enjoy detective work and figuring out how to integrate a solution into an existing product?
Make sure the organization supports spending a lot of time speaking with clients, engineering, design, customer service, sales, and other departments to get the big picture.

Is product design your angle?
Does the organization have a dedicated design team that you can spend time with? Or a spread thin internal resource? To get a sense of this, ask how PM interacts with design. If design expects a fully fleshed out end to end wireframe before you can speak to them, then they have no time to explore an ideate on fresh ideas.

Do you love learning about technical challenges?
Do you want to get into the weeds with engineering? In this case, make sure you are the one writing the user stories and participating in the scrum calls, there’s no better way to get the pulse of the engineering organization.


At the end of the day, finding the right opportunity is all about asking the right questions. Remember, every interview is an opportunity to discover if there is a fit. Don’t be afraid to ask!

About Gregory Rakovsky


Greg is Product Manager with experience in B2B SaaS, and consumer facing products. Focused on the customer experience and building stakeholder alignment. Currently on a mission to help get people in shape @ Blink Fitness.




More About The Product Mentor

TPM-Short3-Logo4The Product Mentor is a program designed to pair Product Management Mentors and Mentees around the World, across all industries, from start-up to enterprise, guided by the fundamental goals…

Better Decisions. Better Products. Better Product People.

Each Session of the program runs for 6 months with paired individuals…

  • Conducting regular 1-on-1 mentor-mentee chats
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  • Participating in live-streamed product management lessons and Q&A
  • Mentors and Mentees sharing their product management knowledge with the broader community

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Jeremy Horn
The Product Guy

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