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How to talk so people will talk: ask indirect questions

Deploy Empathy
Deploy Empathy
This was written as part of the rough draft for Deploy Empathy, a practical guide to interviewing customers.
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When you’re talking to customers, you want to find out what their problems are. You want to find their needs. You want to find out where they’re struggling.
So you know which features to build and what to write on landing pages and how to structure your product so they’ll use it. They get to do something faster/cheaper/better, and you get to have customers. Everyone wins!
The problem is…
You can’t use any of those words.
Not literally, at least.
(You’ll need to bear with me for a moment.)
I’ve noticed some commonalities among people who’ve genuinely given customer interviewing a go but didn’t feel like they got much out of it.
One of them is asking a question that is the direct inverse of the answer they want.
“I need to know what customers need. So I will ask them ‘What do you need?’!”
If you’ve ever asked anyone those questions, I’ll bet you can tell me how you didn’t really get anything useful back.
It’s cognitively difficult to answer a big, vague question like “what do you need?” and a question like “How are you struggling?” can be a bit offensive, especially when people aren’t in a situation where they feel comfortable being vulnerable.
Dave Ceddia replied to the Screenshare Test Script with a great example of this:
“I liked the bit about avoiding implying they’re "confused.” I’ve had a similar reaction to “struggle” where I’d ask “What are you struggling with?” in a welcome email, and I’d get some replies like “Well I’m not STRUGGLING but I’ve just been stuck on this thing for 3 days.”
You can see that they’re clearly struggling if they’ve spent 3 days on something…but the word also kind of offends them.
So… what do you do instead?
You listen for other things, like time and money spent.
What to say instead of “How are you struggling?”
The key is to ask about things that are the symptoms of struggle.
If they’re spending a lot of time, using multiple tools, spending a lot of money, those are all signs of struggle, and allow you to uncover struggle in a way that’s mentally and emotionally easier for them to answer.
Here’s how you ask about things that imply struggle:
  • How long does it take to do [X]?
  • What was like to get started with [X]?
  • How many people do you need to work with to get [X] done?
  • Did it take longer than you expected to [get started/integrate it/etc]?
  • How many different tools do you use to do [X]?
  • Of this process you’ve told me about, what takes the most time?
Time and money spent are particularly good proxies for asking about struggle. Ask about what they are already doing to do this.
If they aren’t spending money and it doesn’t take them a long time, that’s a bad sign. But if you keep digging into the adjacent steps, I bet you’ll find something.
Alternatives to “What are your problems?”
When it comes to “What are your problems?”, this is another question that’s the literal inverse of the answer we’re trying to get. Problems can mean different things to different people and different contexts, and we don’t really want to hear all of their problems… we want to hear the relevant problems.
Like with “struggle,” we need to ask indirectly about “problems.” What you want to try to do is discover the overall process and find where they are spending a lot of time, money, or frustration (such as manual steps).
Picture your favorite childhood board game for a moment.
Imagine your customer is on board game board, and they’re moving through steps of a process. Your goal is to figure out which step of their overall journey your product is solving and the steps next to it to help them move through the whole board faster/easier/cheaper.
I’ll never forget a Switch interview I did years ago.
They were telling me about how they used our Census income data appends to target marketing mailers. I asked them what they used before us, and they told me how they used to use a competitor. With that competitor, they would have to talk to several different sales reps in different departments (each with their own pricing and data formats)…to do something that took two extra clicks with us.
They didn’t articulate having to jump through all of these hoops as “a problem” or as “struggle,” but it was clear it was time-consuming and frustrating.
Yet they trudged through because they didn’t realize there could any alternatives to it. But once they found something that eliminated those struggles (time spent talking to sales reps, time spent normalizing data, all of it for a higher cost), they switched quickly.
The indirect questions to use to ask about problems
If you are in the discovery phase, some of the questions you might ask to find problems without saying “problems” are:
  • What’s your overall process to [do X thing your product would be part of solving]?
  • How long does each step take you?
  • What tools do you use for that? How much do you pay for them? What do you think of them?
You want to pay particular attention to:
  • What kind of tool they’re using for something (note: I’m using ‘tool’ in an anthropological sense here; a manual process or way of thinking/approaching something can be a tool as much as a piece of software)
  • Whether they pay for it with money or time, and how much
  • What they think of that other tool and how they’d change it they could
If you already have a product and want to find adjacent problems, you might ask:
  • What do you have to do before [and after] you do [thing with our product]?
  • How long does that take you?
  • Do you use another tool for that? [how much do you pay for it?]
  • Do you like it?
  • If you had a magic wand and you could change anything about the [whole process/that particular step], what would it be?
“What do you need?”
When people ask customers what they “need,” they’re asking the customer to design the features and systems for them. That’s a huge mental overhead for them, and they also don’t have the context behind what’s feasible or viable for us to create.
In order for a product to be successful, it needs to be valuable for the customer, usable by them, viable for you to support commercially, and feasible for you to build. (I’m referencing product management great Marty Cagan here.)
But you may have noticed a problem with those lenses: Customers only know the first two, and only we know the last two. I think this is why people can be skeptical of customer ideas.
Since customers can’t possibly know what’s viable or feasible from our perspective, it makes sense that asking them what you should build doesn’t lead to good results.
They don’t have the full picture!
But if you don’t ask them about what they’re trying to do, you won’t either.
I feel like this is a good time to dispel a myth about customer research and listening to customers more broadly:
Being a customer-driven company does not mean you take “marching orders” from customers.
You always need to filter what people say through those lenses of viability and feasibility. The customer can’t possibly know what your full capabilities, resources, incentives, and constraints are. So it’s better to just save everyone the time and not ask directly what they need, and instead ask about their process, what they’ve already tried, what they’re currently doing, and where they’re still spending a lot of time or money.
Your fundamental job as an entrepreneur is to turn people’s problems into solutions that solve their needs.
You aren’t on your own for how to figure that out.
All of the scripts and tools in this newsletter are designed to help you do just that.
It’s counter-intuitive, but I promise asking indirect questions will have better results.

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Deploy Empathy
Deploy Empathy @mjwhansen

A practical guide to interviewing customers

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