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Make Questioning your Superpower


Guy Brunsdon

26 August 2022

Asking the right questions is a fundamental requirement in discovering the needs of your target market. So how do you make it your superpower?

"The most serious mistakes are not being made as a result of wrong answers.
The true dangerous thing is asking the wrong question."
Peter Drucker in Men, Ideas, & Politics (1971)

A successful product hinges upon understanding the needs of your market. You don't discover those needs through osmosis; you must ask questions. But, as Peter Drucker, the famous management guru, points out, you don't want to ask the wrong questions.

So, what do you need to ask? Customers are typically poor at relating their frustrations, struggles, and desired outcomes—you need a discovery framework. This process will help you uncover met and unmet customer needs, find segments of opportunity, help define your value proposition, and identify and prioritise development.

Preparation Guidelines

1. If you can swing it, always choose face-to-face interviews versus teleconference. It just works better.

2. If you must use Zoom or Teams (video), ensure the audio and video quality is up to snuff. I've made the mistake of persisting through an interview with a lousy room echo. The result was a net negative for both sides. Rookie mistake—I should have postponed.

3. Avoid having the sales team present. Sales have a different motivation (retiring their quarterly quota).

4. Find the right people to interview. Keep it small. I like 1:1 best. There are other job roles requiring different people at the customer. How do they define their job? What's the subordinate or associated job you're looking at? For every job and market, there is a "job executor" who performs the "core functional job" and a "job map" of the discrete steps job steps (and needs) required to complete the "job". There are also other associated jobs:

a. Consumption chain jobs associated with the product lifecycle (purchase, install, set up, maintain, etc.)

b. The financial job associated with the buyer or purchase decision maker

c. Emotional jobs are related to status or feelings. Emotional needs can trump functional. Bain & Co use an "Elements of Value" pyramid model (resembling Maslow's hierarchy of needs) to express how humans evaluate products. It progresses from functional to emotional to life-changing to social impact.

5. "Jobs" remain stable over time and do not dictate a technology. For example, think about how you've (if you're old enough) accomplished the "listen to music" job over the years (LP > cassette > CD > MP3 download > streaming).

6. Each job step will have a set of desired outcomes (needs). These are the metrics by which customers judge the product's suitability for the job. i.e., how well you solve the problem. Each desired outcome should be structured as follows:
Direction of improvement + Performance metric + Object of control + Context

Discovery Interview Question Guidelines

When you get to the interviews, you'll want to follow a process to avoid annoying or wasting your interviewee's time. Aim to cap it at 30mins, but if they want to keep going and unload their frustrations, go for it.

When you're conducting discovery interviews, bear in mind the following:

1. You're exploring the "problem space" to discover qualitative information about them performing their "job."

2. You're not selling (at this point) but instead trying to understand what wastes time, annoys them, etc. These will feed the needs/outcomes that they will then quantitatively assess for importance (problem space) and satisfaction (solution space)

3. Use open-ended questions (not yes/no)

4. If you need to dig deeper on any point, say, "can you tell me more about that?" or use the "five whys" technique (a series of "why" type questions to discover the underlying reason for something … often used in "Root Cause Analysis")

5. Remember, it's a "discovery" exercise, so there are unknown unknowns. We are trying to find unmet needs—things that annoy and are not currently addressed by anyone. So, follow your nose. We can add what you discover to the body of knowledge around desired outcomes/needs (for later quantification).


A suggested sequence is as follows:

1. Start with validation of "the job to be done." Then, have them sketch out their job and responsibility hierarchy.

2. How important are these job(s)?

3. What is the impact of a failure?

4. Pick something from the job, and ask

a. What's the sequence/process from start to finish?

b. How often do you do <x>? (use the "5 whys" to discover why they do it with this frequency)

c. What annoys you about <x>? (use "5 whys" again to dig)

5. What are your biggest challenges and frustrations?

6. What activities consume the most time? How much time?

7. What three activities did you spend time on last week?

8. What worries you the most? Why?

9. What are your most important activities? Why?

10. Ask them to walk through some actual (bad and good) experiences (this is *very* important as there is a tendency to generalise and smooth out the all-important wrinkles that we wish to discover)

a. Note each of the steps and ask questions along the way

b. What triggered the situation? Is this common?

c. What were the successful exit criteria from this situation?

11. Who are the other stakeholders?

a. Financial (the buyer and/or approver). What are their needs?

b. Product lifecycle: who conducts the receive, install, set up, train, maintain, repair, upgrade, and disposal tasks? What are the desired outcomes for each of these steps?

12. Do you have a picture/vision of Nirvana (wrt to this job)? (you want to ask this at the end as it may head into solution space.

Improving your Questioning Superpowers

Several online resources and product management books cover product discovery questions. I'll leave the reader to do the googling!

But I must highlight one book above all others. One of the best, if not the best, book I read during the COVID-19 lockdowns was "Questions are the Answer" by Hal Gregerson (MIT Sloan School of Management) and Ed Catmull (President of Pixar/Disney Animation) ( I have recommended this book to several friends. It's on my "reread" list. This book goes beyond what you might use in a customer discovery session—it's something you can apply in your everyday life.

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