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14 questions to ask as a Product Manager

There are no technical requirements to be a product manager. You don’t need a fancy degree, or to pass a certification exam that tests for deep domain knowledge. People become PMs from many different backgrounds, often because they enjoy working with people and solving problems.

Yet product management can be tough at the start because it often feels so messy. You need to make hard decisions with imperfect information. You have limited time to gather and communicate complex requirements. You must create structure so that other people can actually get the work done, and if things don’t fit together, that’s on you.

Luckily there’s this one weird trick which will make your life so much easier — asking questions!

The right question can bring clarity to any situation and help you progress in the right direction. In this article we’ll encounter a fictional product problem, and ask 14 questions, from gathering requirements to proposing a solution, and ending with execution and followup.

I use these exact questions on a daily basis as a PM; hopefully you’ll find them useful too!

Let’s set the scene. You’re a new PM at a hip tech startup that delivers on-demand cat food (that has to be a thing, right?). It’s a Monday morning and you’ve got some banging lo-fi beats playing. You hear the ‘ding’ of a new Slack notification and open it up to a question from someone in Operations.

Sure, you think. I’ve got time.

[Side note: while we start with an initial conversation, these questions are directed at different people over time. The exact wording can also be adapted for whomever you’re talking to.]

It’s helpful to start off with an open-ended question that encourages people to give you as much information as possible in their own words. Ideally you want to be taking notes (notebook or laptop both work) while they are speaking. Let’s see how it goes:

Me: Hey, tell me what the problem is?

Operations: We had this guy crash on his bike last night and he said it was because his phone was too bright. He was switching from Google Maps (which is dark) to look at his order details and lost focus. He’s fine now, but this has happened a few times. Also riders complain a lot about our app and they say they can’t see where they need to go.

You’ll get a lot of info with the previous question, and the next task is to untangle and simplify it. One useful way to do it is to establish a baseline for how things work right now, and what change somebody is requesting. Later on, you’ll want to describe this as a user flow, i.e. a sequence of actions.

Me: So how do our riders use the app at night, and what do you think we should change?

Ops: It seems that when it gets dark our riders usually turn the brightness of their screens way down, but then they can’t see their order details. What they’d like is a ‘dark mode’ where they can still see the important stuff but not be blinded.

After listening to someone explain a complex problem, it’s helpful to repeat back what you understood. This lets you check your assumptions and make sure you’re not missing anything, and also gives you practice in explaining the problem in your own words (hot tip: this works great in relationships too!). Later on you’ll be presenting this issue and a potential solution to a lot of other people so you’ll want to start getting a handle on how to communicate it.

Me: Can I check if I understand you correctly? You’re saying that drivers find it hard to use our app at night because the screen is too bright, and this is leading to accidents. What you’d like is some kind of dark mode where they can see their order details when they are on the go.

Operations: Pretty much, and it also needs to work well when they switch between our app and a navigation app.

With this question you want to understand if this is an isolated incident or a recurring pattern. Ideally you also want to quantify the seriousness of the problem in terms of lost users, revenue or some other north star metric.

Me: What evidence do we have of the problem, like is it losing us riders or costing us?

Operations: Well, we pay our drivers’ insurance and hospital bills and it can get quite expensive. Also, we did a survey of driver habits and 30% of them said they switch to another app in the evenings. When we followed up, they said it was because they felt our app was unsafe.

[Side note: you’ll want to validate all this info later on with some data analysis.]

Once you’ve understood the problem, you need to prioritize it against everything else you’re doing. Bonus points if it has a clear and serious impact, and ties into a broader company objective. You’ll also have to pitch this to your stakeholders and the rest of the company, and be prepared to justify the tradeoffs. This is a good question to ask yourself first.

Me: Is this the most important problem we could be solving right now?

Mirror-me: Good question, me. We need to finish this quarter’s projects first. After that though, our backlog is mostly tech debt and I’d say this takes priority especially since it fits right in with next quarter’s OKR of increasing online hours of riders. Let’s use the next 4 weeks to scope out a solution and then start development after that.

Once you have a good understanding of the problem (ideally supplemented by data analysis, surveys and/or UX testing), it’s time to work on a solution. As you start crafting a pitch, you’ll want to answer some critical questions with the help of your team.

Use some blue-sky thinking here and put yourself in the shoes of your users to imagine the best possible experience for them. Don’t think about technical constraints or cost yet — there’s plenty of time to scope it down later on.

At this stage it might be helpful to start writing a PR/FAQ (Press Release & Frequently Asked Questions). This is a format popularized by Amazon where you write an imaginary press release describing your feature to your end user.

Me: What is the ideal user experience we could create?

Designer: Imagine the rider’s phone sensed when it was getting dark and automatically switched to dark mode, like in a car. That could be the default, but the rider would also be able to choose a manual mode, or following the system default. We’d probably want to allow riders to set their choice when they sign up and also highlight this feature on our website.

Next, you’ll need to pick a single, currently measurable metric that correlates with the problem you’re trying to solve and can’t be easily gamed. Later on you’ll use this to determine whether the feature was successful or not.

Me: How will we know we’ve solved the problem? How will we track success?

Analyst: Our main goal should be to increase online hours in the evenings, since if drivers feel more safe using the app they are less likely to switch to competitors. We’ll also keep an eye on what percentage of riders enable this feature, and monthly satisfaction survey scores. We should probably run this as an A/B test to be sure of the result.

This is a conversation to have with the whole team, especially your designers and engineering managers. Use the MECE principle (mutually exclusive, collectively exhaustive) to generate a full list of options, and spend the time to discuss pros and cons. Often it’ll become pretty clear which one (or two) to focus on.

Me: What options do we have to implement this feature?

Tech lead: I think there are several ways to do it:
1. We could just change our whole app’s colour scheme to dark mode and not allow users to switch — this would be quickest but isn’t the best UX.

2. We could use some automated library that automatically inverts our colours.

3. We could define two colour schemes and use the system settings to determine if we use the light mode or dark mode.

4. [etc etc]

[Side note: these are just examples, I haven’t actually researched how you would implement dark mode]

This is a good question to ask, if you have the time and resources. Once you have decided on an initial approach, together a prototype on Figma or another design tool, let users click around and see where they get confused. Or run it by other people in the company, especially those who have close contact with your users.

Me: What do users think of our potential solution?

UX Researcher: We found that they really liked having dark mode in the main navigation menu, but not on the profile page because they want to see all their badges nicely displayed. Most users are fine with the app automatically switching to dark mode when it gets dark.

Now that you’ve decided on an overall approach and drafted the product spec, it’s time to check the price. Ask your engineering manager for a high-level estimate of how long it will take. You don’t need granular task-by-task estimates, just an answer on the order of weeks/months.

Me: How long will our solution take, and are there ways to implement it more cheaply?

Tech lead: If we did the full thing, it would take about 6–8 weeks with regression testing and app store release. If we didn’t implement automatic nighttime detection, that would probably cut it down to 3–4 weeks.

Once you have a project nicely designed and scoped out, it’s time to start building!

It’s helpful to have a quick kickoff meeting with your team at the start of development for a new feature where you present the spec and discuss outstanding questions. It’s really important here to check for understanding, and can also be helpful to appoint a feature owner, usually the dev with the most tasks for the feature.

Me: Does everyone understand what they need to do?

Mobile dev: Actually there’s an edge case we need to consider — what if the user receives a system alert in light mode?

Some user-facing changes will require you to communicate this change to your users — that PR/FAQ you wrote for Question 6 might come in handy. It could be as simple as a paragraph in a monthly email, or a full-on website rebuild. You should also let internal teams who will be affected by your release know well in advance.

Me: How will we let people know about this feature?

Marketing: It would be cool to put some of these screenshots on our rider landing page, and we can also add it to our monthly product update email.

After you’ve finished development and (hopefully) released the feature without too much pain, check the stats right away. Often there won’t be any because you’ve forgotten to add some crucial event, or encounter a weird bug. Once you’re sure it’s working correctly, ease off until you have a meaningful volume of data (If you’re running an A/B test, this will be once you’ve reached statistical significance).

Me: What does the initial data say?

Analyst: Uptake on iOS has been super positive, half our drivers are using it! Android is about 10% lower, seems we might have missed something in our design?

This is the easy part! With the answer to the previous question, you’ve usually got a pretty clear idea of how to improve things.

Me: Good job everyone! Let’s think about the next version now, how do want to make it better?

Designer: I want to change the highlight colour.

Analyst: We need to fix a bug with Android.

Engineer: There are some tech debt tasks we should finish.

Aaaaaaaaand Cut!

In this article we’ve seen how these 14 questions and the answers they elicited have brought structure to a messy problem and helped to define a working solution.

As we’ve seen, it’s more important to ask the right question than to have the right answer. You’ll often discover hidden assumptions or gaps in your knowledge that are way more significant than you initially thought, and this learning can itself be a joy.

Asking a question is also a crucial tool for collaboration — by admitting you don’t know something, you’re inviting others to help you work together towards a solution. It helps people feel that you’re not micromanaging them and that their expertise is valued.

So, what did you learn from this piece?

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