"I should have asked you this"

Dear adventurer,

The stereotype of the hard-hitting journalist has always rubbed me the wrong way.

The reporters I know bear little in common with the tabloid-esque characters you see in the movies, shoving their mics and notepads in people's faces and shouting invasive questions.

Real-life press people do ask tough questions — but with finesse. And they also do a lot of listening and caring.

The best way to get at the heart of an issue is by asking hard questions with confidence and kindness.

This kind of inquisitive spirit is a hallmark of all great product builders. You know that directly engaging with end users gives you a window into their pain points, preferences, and behaviors. And customer interviews are critical to developing successful products that truly meet user needs.

But there are two challenges that hold folks back from gaining real insights.

The first challenge is related to skill. Product discovery is something we all know is critically important, yet few organizations train people how to do it and effectively integrate it into their product planning.

(Our challenges led us to recently launch Aha! Discovery, which helps you manage customer interviews, uncover key product insights with AI, and link them to your roadmap.)

The second challenge is driven by fear. Even when we have a mandate to talk with more customers, we are not always eager to do so.

I personally know how hard it is. It took me years to get comfortable continuing to ask "Why?" until I really understood the motivation behind someone's answer.

Some even dread having to ask others probing questions that we think might make them feel vulnerable and, in turn, make us feel uncomfortable. A lot of folks are just not enthusiastic about what they perceive as pumping someone for information.

Your job is to uncover your customers' challenges, needs, and hopes. And to do that, you need to act like a curious journalist searching for the truth.

It is normal to feel a bit stiff when you are speaking with someone you do not know. And it is even more normal to feel embarrassed asking them to tell you what they do not like about your product or where they struggle. Even if you are going through a somewhat simple usability review, getting past the surface level takes intention.

It helps to document best practices for product discovery so anyone on the team can approach customer interviews with confidence. A good script helps too.

Beyond that, these are the tips I usually share with new folks who join the Aha! product team:

Know your purpose

Establish some basic goals for the session. This way, you can tie each question in your script back to your objectives. And do some research ahead of time. Go through your list of customers to check out their LinkedIn profiles and look at their account information (if possible).

Even a basic Google search will help. Having some background will make it easier for you to establish rapport and ask follow-up questions on the fly.

Establish rapport

Be empathetic. One misconception is that you have to hammer people to get them to open up. Lean on your research instead. People are usually flattered when you can tick off their accomplishments or experience, which shows you value their expertise.

Do not be shy about sharing behind-the-scenes anecdotes that showcase some of your own vulnerabilities too. This creates an environment that is centered on bi-directional information-sharing and learning.

Stray from the script

Write down how you want the conversation to flow and your key questions. Definitely avoid any question that can be answered with a "yes" or a "no." A good way to do this is to start with "why," "how," or even "Tell me about ..."

It can be tempting to treat your script like a checklist, especially if you are a little nervous or feel awkward interviewing people. But moving from one question to the next never delivers deep insights. Asking those probing questions and continuing to ask more does.

Echo what people say

Never be satisfied with the initial answer. One way to encourage folks to share more is to repeat the last thing they say as a new question. If a customer tells you they spend a lot of time doing a certain task, parrot back, "You spend a lot of time doing that task?"

This simple technique often leads to deeper explanations. Follow that up if you need to with, "And I am curious about ... ," which will make it easy for the person to tell you more.

Get comfortable with silence

Sometimes it is best not to say anything at all. Allow a few moments of silence — most people will want to fill it and continue talking. This does not need to be an uncomfortable silence either.

You have already established rapport. So continue that sense of friendliness and openness in these quiet moments too. Smile and nod thoughtfully, absorbing what they just said so they feel safe to keep sharing.

Let them correct you

Intentionally get it wrong. For example, when we were researching the Aha! Discovery product, we would often state: "Your team has a mandate for talking with customers during your roadmap planning — right?"

You have to use this technique judiciously, as you do not want to inspire doubt about your ability to solve their problem. But having a few questions in your script (or follow-ups) that are slightly off can be powerful. In their rush to correct you, customers will often share real insights.

Keep going until the story fits together and gives you clarity about your customers' underlying pain points and motivations.

Delivering something of value takes wonder and guts. You have to care about what you do not know and care about the person with whom you are speaking. This starts with the strategy you set and the direction you go with your product — including the way you approach customer research.

You do not want to leave a conversation thinking to yourself, "I should have asked about this," or, "I do not understand what they meant by that."

Be confident and ask the hard questions. Because hard questions yield real insights.

And if you are not going to ask them, no one else will.

Inquisitively yours,

Brian