When we are experts in the thing we do, it’s easy for us to see the benefits. 

Work in dentistry? You understand the relative ease of flossing, and yet. 

Work in internal medicine? You understand the relative ease of eating a diet rich in fruits and vegetables, and yet. 

Work in scheduling software? You understand the benefits of sending a link to book a meeting, and yet. 

Psychologists call this phenomenon the “Expert’s Paradox.” Being an expert at something - like your own product or the problem your product solves - leads experts like you to sometimes miss important details, take shortcuts, and arrive at faulty conclusions. If you’re grappling with it yourself, you might take heart in knowing that research suggests this phenomenon is not only psychological but also physiological. The brains of experts develop structurally different pathways to practice expertise than the brains of newcomers to the same skill. 

This means many experts are beginners at understanding how newcomers develop expertise. As soon as we have the skill we are teaching, as soon as we understand how our solution helps people with a problem, we no longer see it the way that a beginner would. Even acknowledging this can be a challenge.

So for someone to both express that they are an expert and acknowledge that others who don’t share their expertise may have a different POV is a rare thing. Elizabeth’s post does just that.

Here, Elizabeth acknowledges her POV (she’s an expert at scheduling link software) and acknowledges that others don’t use this technology the way she does (others use alternative means to book meetings). She then expresses her curiosity about why others don’t use the software she has observed to be so powerful. 

It sounds like a small thing, but Elizabeth’s observation shows how she overcomes the structural barriers of the expert’s paradox. She not only identifies her gap in understanding, but she also expresses curiosity about filling that gap.

This post is about what happens next, about how to turn that curiosity into actionable intelligence - by moving away from the question you pose at the beginning of your study.

The “Why” question Elizabeth poses in this post is usually the question that starts a research project.

Teams bring me into their organizations specifically to Find Out Why something is happening, why sales are plateauing or declining, why customers aren’t adopting the thing they said they would, why selling to a committee as you go upmarket is so much harder than selling to an individual.

But even though you will start with a research question that starts with “Why,” as you develop your interview and discovery questions you will want to start shifting away from questions that begin with the word why.

Why? (lol) Asking your buyers and users questions that start with the word “why” can send you off the path in these 5 ways.

1. Unintentional spread of misinformation: Sometimes we don’t know the reasons we do something. Why did you load the dishwasher that way? Maybe you had a reason, maybe not. Maybe you understand that reason, maybe you don’t. If you ask someone “Why don’t you use a scheduling link” in a survey form or even outright, you’re likely to hear invented-on-the-spot reasons.

2. Implication that personal motivation is the only answer: The phrasing “Why don’t you” or “Why do you” also implies that the reasons for doing or not doing something are contained entirely within the individual’s motivations, which may or may not be the reason they made their decision. For example, “Why did you stop using this tool?” Maybe you answer that your boss told you to use something else, with your motivation being, “Avoid making my boss mad.” But maybe the actual answer is more complex, maybe someone used the tool in a way that made the boss look bad in front of a client.

3. No room for the whole truth: The reasons for why we do something are often too vast and complex to offer a reasonable and complete answer in the timeframe of a conversation. Why do you stay in the job you say you don’t like? Sure, someone can give you an answer, but is it the real answer? The complete answer? The answer that helps you make a decision about whether to start looking for a new job? Unlikely.

4. Inadvertently accusatory: Asking questions that start with “Why” can carry an inadvertent accusatory tone that puts someone in a defensive posture rather than a collaborative one. The hostage negotiator Chris Voss writes about this in Never Split the Difference. 

5. Reliance on interviewees to filter what they think matters to you: Ask someone “Why did you” and you’ll get answers the person believes are answers to that question filtered through their lens of experience. This will happen in any question you ask, which is why we want to ask our questions in different ways.

So if you want the truth, the whole truth, and nothing but the truth, asking “why” during the interview, survey, and active research stage of a project sets you up to hear misinformation, incomplete stories, and guarded answers. You’ll learn some of the reasons why someone behaves in a certain way, but not what you need.

You are investigating why something happens or doesn't happen. But you are asking about something else entirely.

To understand why something is happening, I run “timeline interviews.” 

When I run these interviews, I imagine I’m one of the friendly quirky disarming police detectives on television like Monk or Columbo or Elsbeth Tascioni. Just as the detectives survey the scene and establish a timeline of events before they start building their case, I approach timeline interviews as if I’m only here to collect information about what happened. “Just the facts,” as it were. I want to understand the order of events leading up to someone’s decision to do or not do a thing before I start making any judgements or assessments of why those events unfolded the way they did. 

I learned to conduct these interviews as part of my training as a practitioner of the Jobs To Be Done theory of innovation. If you have not run an interview where you have identified the 4 forces or you don’t know what I mean by that expression, don’t worry about this theory for now. If you have run interviews to identify a person’s Job Story but haven’t found success, this piece will help you run your own interviews. 

Timeline interviews are like plays in 3 acts. Here are the questions to ask at each stage.

To begin, ask questions to learn about your interview subject’s world through their eyes. You want to understand the context of this person’s experience so you can orient yourself to the characters and forces that affect their day-to-day and the path they walk to a product like yours. In the case of scheduling software, is this person booking meetings for their business? Sales calls for their job? Appointments for clients? Kayak excursions?

Here’s how I start:

At the beginning of the call, your product has not entered the chat. You might mention your product’s name if it comes up in conversation, but the primary focus here is to understand your customer’s world and their world related to the problem you solve.

If you ever have the great fortune to study screenwriting, you will learn the structure of your favorite movies. Which is loosely this: we see our character, doing what they do every day (that was Act 1) until one day, something happens that they never could have expected. That’s the start of Act 2. 

Something changes that sends the hero on their quest. In our world, we call this the leadup to the “switch” moment, which is when someone stopped doing something the way they always did it and adopted a new solution, hopefully yours. 

Study the switch, know the detailed and nuanced sequence of events from when someone first started considering a solution like yours until the moment when they have fully incorporated your product or service as a habit in their business and you will know how to solve 90% of your product and marketing problems. 

This approach gets amazing actionable intelligence because your users don’t exactly know why they do or don’t do something. Their motive may not be some internal psychological moment of coming to terms with wanting to do something, it may simply be the next thing they did after doing a series of other things. Understand the sequence of events and you’ll understand where to dig in.

Your user has finally reached the point where the event you are interviewing them about has happened. The crescendo, the moment of the story when kablammo, when everything changed again and the plot resolves. 

You will want to do these interviews in a “Win Interview” scenario to understand what happens after a person has chosen your solution and found success. But when you are investigating why someone doesn't do something, your “Loss Interview” questions might look like this.

You’re inviting your interviewee to remember what happened, remember what it was like. The script I’ve chosen to focus on here is not one that explicitly delves into the emotional factors but you may find that people will still share what it feels like.

What do you learn when you study a timeline? It’s a hard question to answer in a tidy paragraph because it’s kind of like asking what do you learn when you watch a movie? You might learn what a place looks like in the early hours of dawn. You might learn what it sounds like in the evenings during a late summer sunset. You learn about people in that place, you learn what makes them laugh, what makes them cry. You learn how they argue and how they come back to each other’s arms. You learn what kept them with the person they should have left and what drove them to leave the person with whom they should have stayed. 

Kathy Sierra’s way of describing what you learn is this: The Rest of Their Life.

What is a scheduling link anyhow? It’s a step in a workflow for coordinating an event with another human. Another human. Human person. You send it and then another person clicks on it and then you both show up at that time and talk about stuff together.

You’re scheduling time together. With another person. One of many other people you’ll probably schedule time with this week. Some for work, some at home, some at school, some out in the community. Some with links, some not with links, some on the shared family calendar, some only after you check the paper calendar hanging on the back of the door. The people you schedule with are also scheduling around things. The meeting with the boss. The school play. The unexpected trip to the garden center to pick up salt to prepare for the storm that’s headed inland now.

It’s copying and pasting a link. But it’s copying and pasting a link that fits into the context of at least two entire lives. Maybe 2, 3, 4, or 10 or more people if you’re booking a call with a big group.

Run a timeline interview and you’ll learn about your users’ life and all the factors they might not have ever explicitly connected as reason to use or not use a scheduling link. All the many many many reasons why.

In our example, you might ask about the events someone books with scheduling software and learn they book consulting calls when they work from home. They need to schedule around their son’s trombone lessons. Your interviewee might mention that the trombone teacher is a childhood friend, and they might reflect out loud about how they wish they hadn’t let their musical skills fall by the wayside as they got older but such is life. They have some meetings they can book with light trombone serenades in the background (like an established relationship) but others they want to book around the 76 trombones at the big parade. They tried a link tool, but stopped because it was too hard to juggled “trombone okay” and “trombone not okay” statuses. 

You might ask what else someone has tried and hear about the assistant they hired to help them coordinate calls across 3 different email addresses in Teams and Google so they could offer a premium embedded experience to their clients. You might learn that they had a 3 way call with IT at the client companies and still couldn't make it happen. So rather than let their calendar share names of all events with everyone, they kept them un-synced and lived in constant fear of inadvertent double-booking. They tried another three tools but they were so bad that one of their clients told them how hard it was to book events and they cowered in embarrassment. 

You might ask your interviewee about their business and learn they work with clients in California and Paris so their days are long and broken up into odd increments so it’s hard to get into deep work mode. They might mention that they want to get their calls into a standard 9-5 so they can spend more time writing, but they would have to make a big ask of these two clients who are their longest running relationships and they just don’t have it in them to do it.

If you’re an expert, you’re hearing the reasons they give you.

You’re also hearing the solutions they never asked for. The things a non-expert wouldn’t know to be possible. The things you could build or communicate to bring more people back to booking links.

For example:

The parent of the young trombonist is booking calls while working from home. The parent is booking calls around a non-work schedule, the family schedule, which may or may not be synced with her calendar. It’s a teenager’s schedule, which may mean by its nature it’s unpredictable and syncing would only be a guess. Can you give this person a way to manage this unpredictable background noise? A “never book during trombone time” setting for certain email addresses maybe?

The person syncing calendars across three email addresses tried in vain to make her tech work, hired a person, the person wasn’t able to do it, and now the risk of double-booking again is too much to take another risk. Can you change how event privacy settings show up?

The person with the time zone challenges clearly needs a way to manage meetings across time zones without being so available that they lose themselves. Can you let someone adjust the meeting times based on the booker’s time zone? 

Another way to interpret your findings is that there’s a root problem, which is each calendar booking link has its own settings. If you want to change a setting for one person but not for everyone, you need to set up a new link. That new link might have your old availability which you may want to keep but you may want to change for a different time zone. And before you know it you have 7 different links and it’s easier to just say “How is 2 PM tomorrow?” 

What if instead of availability + links that use it, there was a link + availability and settings tailor-able to each person before you sent it out? Something like this would help me so much.

There’s a sixth reason why I recommend against asking why, which is that it’s not enough. It’s one angle of approach, one question, one answer. But “the factors that influence the why” are many. Asking who, what, where, when, and how gives you more information, more actionable intelligence you can use.

After all, on Elizabeth’s post, this is what I wrote:

And then I came over here and wrote an entire article on how much more is buried beneath the question of “why.”

Conversational “why” questions lack the exhaustiveness you need to get to the heart of the matter. But so many others give you data you can turn into revenue, relationships, trust, quality of life, and behavior change. 

Do you have a thorny problem your team needs help figuring out? Tired of blaming AI for lagging sales and looking for something that is in your control? Book your meet & greet to see if a Find Out Why project is a fit for you.