Five counter-intuitive questions you should ask your users this week

Unless you’ve been living under a rock you’ve probably been told a million times you need to be obsessed with your users. Talk to them every week, know what they’re thinking and feeling, and put yourself in their shoes when you build and execute product vision — your know, your standard soothsayer stuff. And if like every good product manager you’ve already started to do this, then you know how hard it is to get real “aha!” moments from these conversations.

I need to talk to users every day while I build fintech products for them at IDEO. These are my go-to questions for insightful conversations that open up new possibilities:

1. The “day in the life”

You are busy, your users are busy. It’s tough to pin them down for a long chat and you’ll often hear things like “I only have 15 minutes”. So it’s tempting to jump into the questions you specifically have about your product or show them how it works. But over time I’ve realized the single most important thing is understanding what sort of lives your users live. When does the day start, what rituals have they built into how they go about things, when does it end, what’s hard about their life, and what brings them joy? Asking these can often help you find those specific moments in which your product can fit into a need (think Uber) or help scratch an itch (think a shopping or gaming app).

2. The “hard thing about the hardest thing”

If you’ve started right then you’re building something that helps solve a problem or a need for users. It’s absolutely necessary to have a deep understanding of that problem. But equally importantly — where does that problem stand in comparison to all of the other problems in their life? If they were to stack rank it, would it even come up on top? And if it does, then what’s the hardest thing about it? Whether you want your user's time or money or both — how much of it you can get and how often is almost entirely driven by how deeply and frequently they experience the problem you’re trying to solve.

3. The “playback”

Ask your users how they’d describe your product to a friend they were recommending it to. At the most basic level, it’s a great gut check for whether they actually grok what you’re building. But it gets super interesting when you hear them articulate a value prop that never struck you as the big hook. Or like me this week, you might get your #$@ handed to you on a platter by a user who says: I will not tell my friends about it yet. I need more time. How do I know this is not a scam? Ouch.

4. The “nasty license”

It’s hard for users to be critical of your product to your face. Especially if you’re visiting them at home or at their place of work. They’re feeling the pressure to be good hosts (cue “chai peeyenge?” in India). And let’s be real: a five-year-old could tell how much your product means to you. Don’t ask them if they like your product. Instead, give them the license to be critical without being rude by asking questions like “When you look at/use our app, what do you feel worried about?” or my personal fave “Imagine our company has to shut down in 1 year because we don’t have a lot of users. Why do you think that has happened? What might have gone wrong?”

5. The “will the real slim shady please stand up”

I’ve looked at 400+ early-stage pitch decks this year and the majority say “we have no competition”. Fair enough, they’re building fintech in emerging markets where financial institutions are archaic and there’s no competition that looks like them. But there are definitely existing ways in which users solve their problems — through community connections, informal/grey market approaches, and just good old-fashioned jugaad. Most often these non-obvious alternates are the real competition. Ask them “how is what you do today better than our app” and you might be surprised. For instance, I asked a small business owner that question this week (with reference to a working capital app) and this is what he said — Actually for me today the money is free. I will call a friend and he will bring it to me. And when he needs the money I will give it to him. That is what friends are for. So how do you sell affordable working capital loans when the alternative looks like it is free? Watch this space for ideas next week!