Here are the 10 most clarifying questions a PM should ask (often)

pranav khanna
Product Coalition
Published in
5 min readOct 20, 2020

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Photo by Emily Morter on Unsplash

I recently came across this article on “Eigenquestions” which speaks about the idea of identifying the most important question when looking to make a decision or taking on an initiative (“the question where, if answered, it likely answers the subsequent questions as well”). This got me thinking about ways to frame questions that can help busy PMs quickly get to the root of the matter. What are the questions that help cut through the chaff and quickly get to the essence of the topic at hand?

To get started, I thought back to recent product reviews or other senior meeting and started to list these questions by topic — sharing them here in case they are helpful to others. Would love to add to this list — so please share others if you have them

Finding the binding constraint or the most important issue

Question: What’s stopping us from doing X or achieving X outcome (e.g. what’s stopping us from shipping feature X)?

Why I love this question: Often — people ask the inverse of this question i.e. “what are all the things we need to do for X outcome” which often results in a long litany of tasks, most of which are just a matter of doing work but are not critical to the success or failure of the initiative. Framing the question as “what’s stopping us…” allows the questioner to quickly get to the most important considerations that drives the initiative or choice. For example — I’ve found that this question helps to tease apart considerations like prioritization and focus from real technological or other constraints that prevent an initiative.

Question: What is the riskiest assumption for this initiative or decision?

Why I love this question: Along similar lines as above — this question allows the questioner to cut through a bunch of assumptions / hypotheses to get to the one assumption that will make or break the initiative. I’ve written about riskiest assumptions here.

Decision making

Question: What’s the worst that can happen, and how will I mitigate against that risk?

What I love this question: Before making any decision (or shipping a product or feature) it is important to consider worst case scenarios and do some up front planning on actions you would take if those downside outcomes do manifest. These downside scenarios could be situations where the technology breaks, or the customer adoption is not meeting expectations or as is increasingly becoming the focus of product development— the product has some unintended consequences,

Question: What are the reasons to not do X thing?

Why I love this question: Sometimes people get carried away with the momentum of a particular initiative and suffer from confirmation bias. To guard against that — it is helpful to take a “devil’s advocate” stance to make sure you have considered all sides of a argument. This practice from Israeli intelligence is fascinating

Question: Is this a one way door or two way door (i.e. is this decision reversible)?

Why I love this question: Popularized by Jeff Bezos, this questions helps you understand the impact of the decision you are about to make. If it is an easily reversible decision — then often making the decision quickly is the right thing to do. However, if the decision is irreversible — or closes other doors — then it is important to be considered and thoughtful in making the decision (even if it takes longer)

Question: what are (all) the options?

Why I love this question: sometimes we feel like we are backed into a binary choice e.g. whether to do something or not. It is helpful to consider all the options — then consider pros / cons before picking a specific direction.

Strategy development

Question: where is the world going?

Why I love this question: This is a question we often ask at Capital One — which is code for forgetting about our own position on a particular topic — and start from learning about the external environment: what are the trends, who are the leading companies, what are they doing and what does that tell us about where the world is going? Only then do we think about positioning ourself to win

Question: where is the leverage?

Why I love this question: When building a product — there are typically many different paths you could follow, many different ideas for new features to build etc. It is important to be focussed on the path or the choice that has the most return for every unit of effort put in.

(Note — there are a whole host of product strategy questions one should probably ask often as well — e.g. what’s our right to win, what’s our moat, why now etc. — more on those questions in a separate post)

Talent development

Question: If this person (someone on my team) tells me that they want to leave— how hard would I fight to keep them?

Why I love* this question: This is a question from the famous Netflix culture deck and is called the “keeper test”. According to Netflix — “those who do not pass the keeper test (i.e. their manager would not fight to keep them) are promptly and respectfully given a generous severance package..”. While some think of this question as too cut-throat or harsh, it can often serve to clarify how much you value someone on your team (and where people need additional coaching etc.)

Question: If I were drafting a new team right now, would I pick this person?

Why I love this question: Similar to the Netflix test, but different context — but also can be clarifying on how much you value the fungibility of the person on the team.

Bonus question: When all else fails (and maybe you’re stalling for time) — what’s the problem we are looking to solve?

Why I love this question: As a product person — it is always helpful to true back to the fundamental problem you are looking to solve; helps to validate any idea or solution.

What are some other questions you find yourself asking often?

All views, opinions and statements are my own.

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