21 Comments

I'd love to see you explore a JTBD interview with a more complex purchase, such as Enterprise software (like a CRM replacement or similar).

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I like the CRM idea and I've head a few other requests for an enterprise purchase. I'll put a recruit together and get something scheduled.

In the short term, I have an interview scheduled next week for a product management / roadmapping tool (ProductBoard, ProdPad, Aha!, etc). It'll be fun to see how much enterprise level complexity is involved in that story as well.

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Have you got any specific tips for more complex interviews? I've found that it's hard to shake a habit of going down rabbit holes about what's caused the overall transformation in the enterprise (as often they've hired new people, restructured, or had/plan some major corporate event like an IPO or merger).

The "first thought" was often dissatisfaction over 10 or more years that they couldn't ever get a budget or team hired to fix, until the restructure happens and all of a sudden there's a budget to buy a tool that has to be spent yesterday.

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It’s definitely a balancing act when it comes to how to focus your attention and your questions during an interview. When I spoke to Sennie about her online course purchase we immediately jumped four years back in time to talk about how her career as a nurse didn’t start out as she expected it to. It was worth spending time on because it was fundamentally causal. It was the first domino to tip, so to speak, and without it, she wouldn’t take any other action.

The balancing act is deciding how much time to spend asking questions about that firs thought, and how much time to spend on deciding and buying (why this? why now and not later? etc).

When it comes to the transformation in the enterprise, I want to know if it’s indeed the first domino to tip (similar to Sennie’s story), with new definitions of progress, new struggles, and new problems to solve and purchases to make. If it is and that’s the pattern to emerge over a few interviews, we need to get good at positioning ourselves to detect and react to those kinds of changes.

If it wasn’t the first domino to tip that means that something else started the struggle for the person I’m interviewing and they just waited for the organizational transformation and used it as their opening to make progress. If this is the case I want to understand how they managed to make progress along the way before the transformation. Were they truly just running in place (no progress)? Were they able to pull off some small wins? Is it possible for me to build and sell something that helps people in similar situations between their first thought and the big organizational transformation?

The other thing that I’m constantly reminding myself of is that people have Jobs. Companies don’t have Jobs. With an enterprise purchase someone is putting their neck on the line - spending money, using company resources, betting that it’s going to pay off. If I feel like the interview is falling into something abstract like, “We just finally got the budget so we signed the contract,” I try hard to push into the social and emotional side of things. Who did you have to convince to make this happen? Did it take political capital? How did you decide that it was worth it? What were the biggest risks to you? If it worked out well, what would it mean to you? If it didn’t? Who pushed back the hardest against the project? What were they pushing for instead?

I also want to push into the budget topic. You got budget, but why spend it on this? Why is it at the top of your list? Why did you think it would have the biggest impact?

Hopefully some of this helps. I’m hoping that when I’m able to do some enterprise purchase interviews I can start sharing tips like this over so that the tips are really grounded in concreteness.

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I presume a lot of this is also in the screener questions - getting the right people. What I've found is that the people who come up with requirements (assuming there are any) are often 2-3 layers under those that come up with the budget.

As such I'm unsure whether the struggle they've lived with for years is causal to the purchase (they couldn't persuade anyone to solve it before and may well just have given up), or whether the focus is on some event that caused the Board of Directors to funnel money down.

At what point do these two chains of dominos need to meet to push over something large enough to trigger a company spending a few million bucks on a solution?

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The screener is critical. I started recruiting for a CRM purchase interview, hopefully I can schedule and publish one soon so we can dive deeper into a real story. One of the questions that I included in the screener is, "Often when it comes to a large purchase and integration, someone at the company is staking political capital to get it done and negotiating for budget and resources to make it happen. If the project pays off for the company it reflects positively on that person. How did it work with this purchase?" and providing options for the person to say that they were taking the risk themselves, someone else was taking the risk, or that the purchase didn't have this kind of aspect to it. I'm really trying to target the person who was driving this forward inside the org. The board can be a gate keeper or bless the project, but I think in most cases it's not their struggle and it's not their progress.

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Thanks for this. In my screener I tried using 2 questions, as often people try to make themselves sound more important than they were in the selection process, so after a few interviews where I was talking to the wrong person I had to edit the screener to ask the same thing in a different way to eliminate people that had less influence.

Do you think you can learn anything useful from those who did NOT stake political capital in the process? I'm busy analysing 15 interviews I've run so far, but I might scratch it and start again to see whether I get the same results if I only target people that "owned" the struggle.

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I watched this again, and one thing I'd love to hear you explore on future episodes is how to segregate the Pushes and Pulls from the overall travel/holiday/vacation vs the specific ones for the AirBnB booking.

How much did the stress of not travelling during Covid or the setup of the school impact the decision to stay in an AirBnB? Where do the forces pushing or pulling her to Budapest in the first place end and the ones pushing or pulling her into an AirBnB begin?

I think a lot of my interviews might be "too broad" - where I'm learning about the whole story of "how we got to now" and maybe not focusing specifically on the final nudges that made choosing A more appropriate than choosing B in the final decision.

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This is great. I think you’ve identified a few pushes that I missed in the post.

- When I love to travel but the pandemic has kept me from traveling.

- When I just wrapped up a long and challenging project at work a need a break.

It’s somewhat of a complex story because there are actually a few different switches taking place. Her conversation at the wedding definitely creates pull for Budapest. You can tell that the person she’s talking to is describing his experience, and the lightbulb is starting to form in Roxana’s head: “I want to go there!”

There’s also the switch from other types of places that she’s stayed to Airbnb. So was able to form an idea around, “So I can feel like I’m living in the city that I’m visiting.”

> “I think a lot of my interviews might be ‘too broad’ - where I'm learning about the whole story of "how we got to now" and maybe not focusing specifically on the final nudges that made choosing A more appropriate than choosing B in the final decision.”

The check that I try to use to solve this, “If someone else working on this project acts me why she switched to Airbnb, and away from the alternatives, do I have enough details in the pushes and pulls to confidently answer?”

I try to narrow into the deciding portion of the timeline. It’s down to two or three alternatives. Can I confidently answer why she chose the one that she chose? Can I answer why she switched now instead of just putting off the decision?

I try to ask myself those questions during the interview, and if I’m not happy with the answers I’ll try to keep digging.

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Chris - Thanks for sharing! Really cool to be able to observe the interview, as well as to see your notes and get your post-interview thoughts.

A couple of thoughts of my own:

(1) Interesting that even though she likes to travel and tries to leave the country at least twice a year, this was the first international trip she'd taken since before the pandemic -- and she was traveling alone. I wonder how many solo trips she'd taken internationally before this one. And I wonder how many Airbnbs she'd stayed in internationally before this trip (she mentioned that she had stayed in Airbnbs before, but she had never booked one herself / never stayed in one by herself). And so if she had traveled internationally by herself before this trip, I wonder where she'd stayed (hostels, hotels, etc.).

(2) In addition to not wanting to spend a lot of time in her place in Budapest trying to find an Airbnb (plus the possible points transfer delay issue), I wonder how much of her decisions to go with hotels in Vienna and Prague were driven by the challenges she ran into getting into the Airbnb -- i.e., flight delay in Paris pushing her arrival in Budapest to late at night, then the struggle in the dark alleyway to figure out how to get into the Airbnb.

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Oh man. As I read through your second point I started to imagine my team having an intense post-interview debate over that question. It's such a great thing to call out. Were the hotel stays at the second part of the trip more about a lack of push, and the fact that the adventure box had been checked, or was it more about the fact that just a few days ago she was stuck in a dark alley and she wasn't eager to do that again tomorrow?

In either case, if our product is putting people in a situation where they're feeling unsafe there's an opportunity for improvement. It's just a matter or prioritization.

I'm glad you found the interview valuable, and thanks for sharing your thoughts!

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As a relatively newbie, it feels great to read this.

I feel the need to become perfect at interviewing. Watching your interview, it became clear that there are so many hints where we can choose to dig deeper—more than we have time for. (Dig deeper into the difference between past travels and the choice to stay at hotels in Vienna and Prague, ...)

Simply, covering everything in the interview is impossible, even for a seasoned interviewer like you.

There will always be a question afterward we would have wished to ask.

This takes a lot of pressure out of the interviews for me.

My immediate reaction was: OK, then I must define what I must learn in the interview up front, so I ensure this is covered.

You didn't do it.

Instead, you mentioned which question one might ask (competition, improvement, etc.). Is it because you are comfortable with the ambiguity, and as you are used to doing JTBD interviews, you know there will be relevant information for all use cases? Or is it that you want to make sure your readers see that they can apply this in their use case?

Or rephrased: How much preparation do you recommend regarding what we are trying to learn with this interview?

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"Simply, covering everything in the interview is impossible." This is spot-on. If we're investigating a topic we're probably going to do at least ten or twelve interviews. We get what we can from each one, and at the end of each one we think: "ooo maybe in the next interview we should dig into ____ if it comes up."

My interview preparation is really informal. I think it's mostly to get my head into the space that I'm about to talk about, and to calm my nerves so that I'm not panicking when the person gets on the call and the conversation starts. I'll usually just pace around and think about the topic for a few minutes (I'm a pacer, lol). For this interview it would be something like:

- People take last-minute trips, and they plan far in advance. I wonder which one this was?

- I didn't ask in the screener whether this was for business or pleasure. I can ask about this as I'm laying the groundwork.

- I wonder if she was traveling with friends or family? Did that make it harder to pick a place? Did she have a lot of conversations or debates about it?

- What could Airbnb compete with? Hotels? Other sites (VRBO)? Did she even consider these alternatives?

- Will there be anything tricky about trying to get to the first thought? I'll probably just do my normal thing and ask when the trip took place, then move up the timeline and ask when she first started thinking about planning the trip, and see what unfolds.

To your point, it's less about defining what I want to learn, and more about whether or not my head is in the space and I'm comfortable and ready to start the conversation and dive in.

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Thanks, Chris!

I didn't expect that, but it makes sense to come into the right state of mind.

What I was getting at, so maybe you can explain why this might be a bad idea:

If I'm interested in marketing our product better, I might make sure I get into the details of the trigger, the motivations and how she went from passive to active looking.

If I'm a competing hotel and start researching, I might focus more on the needs and actual job performance and less on the passive-looking phase.

I think you should always establish a basic timeline and understand the consideration set and the trade offs on a foundational level.

Does it make sense? I mean you could easily talk 60 min about the tradeoffs in the consideration set alone. And maybe you should when you are positioning your product.

It's all interconnected, you should never force the interviewee too much, but depending on the business challenge you must be more curious in different aspects, don't you?

Curious what you think about my current understanding

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I agree and I think that it’s a balance. I’ve been in many situations where I feel like I’m conducting interviews because I’m trying to address a specific challenge:

- I’m not sure we’ve built the right thing. What do I build instead? What features do I add? What do I take away?

- I’m not sure our marketing or message is resonating with the people who should be buying this? What about their struggle can I connect with?’

Those kinds of questions will push my to listen for certain things during the interview, but your point about forcing the interviewee too much is incredibly valid. In the case of this interview, I ended up uncovering quite a bit about how hostels and hotels compete with Airbnb, but if I was managing a competing product and my goal was to uncover more details about the competitive set, I’m not sure how much further I could have pushed Roxana in terms of sharing more details. The answer would probably just be more interviews on the subject.

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So interesting to hear that searching & booking late in the evenings long before the trip is such a different context that booking "while you're in it". I would argue the circumstances are so different that you'll have a very different struggle and also candidates - although it is still the same trip. This can lead to a huge opportunity for airbnb assuming that the booking-on-the-trip-context is underserved.

When originally planning she wanted to celebrate after this stressful job-thing (and reward herself with an adventure) but I assume the whole booking process, looking on bigger maps etc is part of the value. Maybe she accompanied herself with planning an adventure while having a stressful time at work?

While "you're in it it" is more about: "what is possible for me on this very trip in a few days"? Quite a constraint.

She just booked the flight, the 1st appartement and the return flight.

I am wondering:

Why is she not starting with a hotel for the first nights?

Why is she not planning the whole trip upfront?

Thx for sharing this great interview!

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Oh that's really interesting. I wonder how cathartic/relaxing it was for her to plan the trip in the evenings as the stressful project was winding down. You've definitely highlighted something that I could have gone deeper on during the interview - that would have been fun to dig into.

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We always can go deeper, right? In the end this aspect became clearer - how mean, after talking for almost an hour :-) Luckily in a real research other interviews would reveal missing parts. The different kind of booking during the trip reminds me on my last camping-van tour. Last summer we were on the road and made several decisions of that kind. Friends on the other hand did plan their whole camping trip upfront.

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Hey Chris - would you be able to record an interview and info on the recruit for a ‘little hire’ project?

I’ve tried these myself and it would be good to get tips on how to be more effective and who to target.

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For sure. Working on getting some more interviews lined up right now. I'll see if I can figure out a "little hire" interview to do.

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