Why? The Most Powerful Question You Can Ask

Tim O’Connor
13 min readMar 9, 2020

ANSWERS, NOT DATA. Why some marketers succeed with analytics and others don’t. (A Medium book). Chapter 3.

“If you don’t know where you’re going, any road will take you there.”

The Cheshire Cat (paraphrased), Alice’s Adventures in Wonderland by Lewis Carroll

Let’s return to Chuck, the person in chapter 2 who almost scuttled the $9M pricing project. It was a given his sales were down, but we figured out it wasn’t due to the pricing project. So what was the root cause of the decline and what was needed to reverse it?

Chuck and his team never did figure it out. Therefore whatever they threw at the sales decline problem never worked because they kept trying to solve the wrong things. Just like Alice, in their situation, since they didn’t know the real root cause of the problem, the Cheshire Cat would tell them that any answer will do. If only Chuck had probed and asked, “Why?”

In cases like Chuck’s no matter how much data you have won’t help because you don’t know what you truly need to get answers for. It doesn’t have to be that way. All Chuck and his team needed to do was probe and ask the most powerful question you can ask to uncover the root problem, especially with analytics. That is, why? Don’t ask it, and you’re likely to identify only the surface effect that we too often mislabel as the problem. And that leads to failure.

Yet asking why is more than just saying why. There’s a specific process, especially with analytics, that we’ll cover in this chapter. Let’s start by unpacking a significant barrier to proper problem definition and lack of probing. In other words, why people don’t want to ask why.

Why people struggle with probing and avoid Why

In my experience, people who fail at the probing and problem definition process, and don’t want to ask why, fall into two groups. One group simply wants to get to build a solution as that is the fun stuff. Working on producing something is filled with creative expression, and in that space, our bodies will produce dopamine, serotonin, oxytocin, and endorphins, the quartet of chemicals responsible for our happiness. Asking why delays you getting on with the fun.

The other group wants to avoid the effort of probing and defining the problem since critical thinking and asking why, is hard. It involves being skeptical and challenging assumptions, rather than merely memorizing facts or blindly accepting what you hear or read. That can wear a person down. Who among us hasn’t had the feeling of mental exhaustion following a deep cognitive exercise such as a test or a similarly grueling mental marathon?

But without the rigor to define the problem, then time and money can all be lost, chasing the wrong thing. Have you ever seen an analytics project go down one road and later on realize it told you nothing? Have you seen an innovative approach to deliver a breakthrough product only to find out that customers didn’t so much care about solving that problem?

I’ve been in many meetings where the business is having a downturn, and without even thinking through the problem, a senior executive will shoot from the hip, saying something like “Let’s do such and such.” When in truth, if they had taken even just a few breaths and assessed what was going on by probing the surface problem and asking why, they might have found out that the issue was something entirely different, and their idea wouldn’t then make sense. I’ve seen this a lot, and I bet you have too. In truth sometimes I’ve been that executive and it bites me in the butt.

There’s an often-cited quote attributed to Einstein that no one knows for sure if he said it, but it captures well the importance of properly defining the problem.

“If I were given one hour to save the planet, I would spend 59 minutes defining the problem and one minute resolving it.”

Albert Einstein? Maybe, maybe not.

Spending time defining the precise issue is, therefore, essential for success with analytics, marketing, business, and life. It doesn’t always take a big investment of time to define the problem either. Sometimes it just takes a bit of thinking and asking a few simple but powerful probing questions.

Why do you say it’s too cold

When I worked for Siemens, I was an adjunct faculty member in their world-renowned sales development program. A few times a year, I taught a 3-day class on selling to healthcare facilities, which included a module on problem identification. In class, I used this scenario.

Imagine your office maintains the heating and air conditioning at a local ambulatory care facility. An influential Doctor is complaining that her/his office is too cold ever since Siemens put in new temperature controls. S/he contacted the Facilities Director at the central hospital, who in turn, called you to check it out since you have a maintenance contract on the building.

I’d then begin to question the class about the problem, and what to do about it. Many students usually and quickly offer up solutions such as increasing the heat or airflow in the room. But is lack of heat the real problem? Well, maybe, and maybe not.

The next step in the class is I’d share that they, the local Siemens manager, met with the Doctor. You saw that the room thermostat is working correctly. The room temperature is 68 degrees, as is the design.

I’d then ask the class what else can you do? At that point, I’d usually hear more solution ideas as if it is a creative thinking session. This behavior will generally go on for a while until a student finally says something like, “How about asking the Doctor, ‘Why do you say it’s too cold?’”

Bulls-eye! When why is asked, it starts to unlock the truth. Why is a probing question, and can surface the root cause of a problem, or unarticulated needs when doing market research.

I’d then help the class by saying the Doctor responds as follows. “Well, because when I put my hand over the heating unit, the air flowing out feels cold.”

At that point, the light goes on for the students as they know, being in the HVAC business, that hot air flowing over your hand will feel colder than the actual air temperature. The issue was two-fold.

First, the Doctor believed, but not knowing, that the room was cold because of what s/he perceived as cold air coming out of the air register, and because of that, s/he thought the room thermostat was wrong. I remind the class a mechanic will usually put a thermometer in the air register and show the Doctor the temperate is fine.

The second issue is the students jumped into premature solution mode looking to be the hero with the best technical solution without spending time asking probing questions to tease out what the problem might really be. All they had to do is first ask: why?

Like everyone, I sometimes short-change probing and the problem-framing step, especially when I’m tired, rushed, have too much on my plate, am not self-aware, or when my ego gets full of itself as I think I’m right and I allow it to rule. When those things happen, and I get into fixer mode too fast, I often later regret it. When I miss the problem framing step and go into Bob The Builder mode, it usually leads to less than ideal outcomes.

But when one properly inquires about the problem and probes a bit, magic might happen. The more you do an in-depth evaluation and probe, the more you’ll identify different aspects of the problem. That, in turn, can sometimes deliver radical improvements; and even spark solutions to dilemmas that have seemed intractable for a long time.

Asking why is the easiest and most powerful way to probe and uncover the truth, especially when you ask it at least five times.

The Five Whys

Kiichiro Toyoda considered Japan’s Thomas Edison, was a Japanese businessman born in 1894, and the son of Toyoda Loom Works founder Sakichi Toyoda. Kiichiro’s bold rebellious decision to change Toyoda’s focus (and name spelling) from a leading automatic loom manufacturer into automobile manufacturing created what would eventually become the global powerhouse of modern fame today, Toyota Motor Corporation.

Kiichiro liked the idea of asking why so much that he led the creation of Toyota’s Five Whys process, its world-renowned scientific approach to uncovering the right problem by repeating why five times. With almost a century of use, this approach has become a vital tool within market research, product development, Lean Startup, Lean Manufacturing, Six Sigma, and all types of business operations evaluation. It also helped propel Toyota’s legendary quality.

Kiichiro Toyoda

Don’t be misled. Five Whys isn’t just casually asking why five times. It is an iterative examination technique used to uncover the cause-and-effect relationships underlying a particular problem. The primary goal of Five Whys is to determine the root cause of a defect or issue by repeating the question: why? The key is that each answer forms the basis of the next question. Therefore, the asker has to carefully listen to the responses to build on to the next why. For example:

Here’s a surface problem: The online conversion rate from paid search is off from last year. So what’s the root cause?

1. Why? The share of traffic from lower converting mobile devices is up.

2. Why? We’ve spent a much greater share of Google PPC and PLA spend on mobile than planned.

3. Why? We haven’t been tracking this as carefully as we ought to.

4. Why? We are not using a disciplined repeatable approach and checklist in looking at weekly results from our online ad agency who is managing our account. I’ll come back to checklists in a future chapter.

5. Why? The person who is leading paid media is more so a brand person and isn’t a strong quant person with the numerical skills needed with managing online advertising.

We’ve now found a possible root cause, and closer to, if not likely the real problem to solve. The questioning for this example could be taken further to a higher level. Still, five iterations of thoughtful asking why, are generally sufficient to get to a root cause or the real problem that needs solving.

You could certainly apply a solution to whys #1 to #4, and that might help short term. But there is still the underlining root cause of #5 that needs to be addressed to assure long-term success.

A fundamental rule in Five Whys is for the trouble-shooter to avoid opinions and logic traps and instead trace the connection of causality in straight increments from the effect through any layers of notion to a root cause that still has some relationship to the initial problem. That sometimes takes a little time as you may get stymied when you ask why. You might need to dive into a particular why and explore it before you can articulate the next why. Therefore don’t expect you’ll have results as clean and fast as the online ad example above. But using this technique will ultimately help you get to the root issue to work on.

In those situations, when the next why isn’t apparent, you can augment your probing using the word why, with a few other probing words. Let me share a personal example.

What to do when you’re stymied with asking Why

A friend is the CEO of a $90 million private equity-owned building supplies business. A few years ago, he asked me if I could speak with his head of merchandising, Zoey (not her real name). Zoey was advocating a significant price reduction as she thought pricing was the cause of sales being down. My CEO friend wanted my opinion.

As I recall, when I spoke with Zoey, the gist of the conversation went something like the following.

Tim: (1st why) “I heard you want to do a price reduction. Why is that?”

Zoey: “Our sales are down about 3%.”

Tim: (2nd why) “Let’s put to the side whether or not a price reduction would stimulate enough demand to offset the lost margin. Let me ask you, why are sales down?”

Zoey: “It’s not clear to me. Everyone has different opinions. I’m not sure but I think it is pricing related.”

Tim: (3rd why) “Why do you want to implement a price reduction if you don’t know what the real issue is?”

Zoey: “That’s a good point. When we promote a sale though, we normally get a bump. What do you think we should do?”

Tim: (I got stymied on my last why, so I try “Are”) “I have no idea. But let me ask you some more questions. I believe you have four main product categories. Are they all down?”

Zoey: “Pretty much.”

Tim: (Still stymied so I try “How”) “How else can you cut your business? How about vendors. How are they doing? Are they all down equally?”

Zoey: “We have a bunch of smaller vendors that are down a lot.”

Tim: (Got back into why flow. 4th why) “Why do you think that is the case?”

Zoey: “We did an SKU rationalization project, and narrowed down the assortment to only two main suppliers per category, and one private brand on some categories.”

Tim: (I’m stymied by her answer so I try “How”) “How much are sales down due to that?”

Zoey: “I don’t know.”

Tim: (Back to why. 5th why). “Why haven’t you looked into that?”

There was silence on the telephone. Now we had uncovered something Zoey could look into, that candidly she ought to have done already. But she didn’t know about the Five Whys, which to some extent was the real root of the problem.

Zoey did the analysis over the next few days and found out the lost sales were close to $5 million. Based upon the company’s growth, when you took that away, the core was up about 2%. Zoey realized that overall pricing was not the real issue but rather sales were down due to discontinuing too many items and no one took the time to consider that.

Using Five Whys we had found the true reason why sales were down. Maybe a promo was still needed, as the same item sales were up only 2%, but maybe a sale wasn’t the best thing to do. Regardless it was clear the bigger problem was SKU rationalization and not base pricing.

Finding the real problem is critical because if you’re going to apply a solution to something, you better know the real problem you’re trying to solve. Otherwise, any answer will do, and that answer might be way off.

However, identifying the root problem is not always as clear as Zoey’s situation. As in Chuck’s decline in sales, sometimes uncovering the core problem takes a more thoughtful and in-depth evaluation, and application of Five Whys and probing. In these more difficult situations though, asking why may lead to a quantum leap in understanding what truly needs to be resolved.

Using Why to make a quantum leap

In 2000 the Oakland A’s baseball team won the American League West title, and in 2001 they followed it by earning a wild-card playoff spot.

The A’s did this with the second-lowest player budget in baseball at the time, of $39,722,689 per year, which was about 30% of the league-leading New York Yankees payroll of $114,457,768.

Then after the 2001 playoffs, the A’s lost three star players, Johnny Damon, Jason Isringhausen, and Jason Giambi to free agency and teams with deeper pockets; the Boston Red Sox, St. Louis Cardinals, and New York Yankees.

Jason Giambi and Johnny Damon, Oakland A’s 2001

What then is the problem to solve? Is it the A’s need to rebuild the team, or do they need to first address a more profound problem as they look for players?

On the surface, it seems like they just need to replace three of their star players during the free agency period. Just go on doing what they’ve always done. That’s easy to define, but it doesn’t explain the root cause as to why they lost the players in the first place and why it won’t happen again.

Let’s apply the Five Whys, and see if we can make a quantum leap to identify the root problem, starting with the A’s lost three key players to three wealthy teams.

1st Why. Why did the A’s lose their star players? That’s easy. Baseball players' salaries have been skyrocketing and big-market, big-money teams are offering more money.

2nd Why. Why don’t the A’s bid more? That’s pretty easy too. They don’t have the money.

3rd Why. Why don’t they have the money? And this is straight forward too. The A’s don’t have the attendance, broadcast revenue, or deep pocket ownership to compete in a bidding war.

The next why isn’t as clear. On one hand, you could easily ask “Why can’t the A’s increase revenue?” This would take you down a path related to increasing the financial means for the A’s to play the same free agency game as big money teams. As a strategy just doing what your competition does isn’t normally a winning strategy, and isn’t what they are doing an example of insanity, that is doing the same things over and over again and expecting different results?

Now the quantum leap. How about asking this?

4th Why. Why do the A’s continue to bid the way they do when they know they don’t have the financial means? The answer: it’s the approach they’ve used for years and they don’t know another way. This leads us to…

5th Why. Why don’t the scouts know any other way? No one showed the scouts a different way to think about how to find undervalued players with a limited budget; players that the big money teams wouldn’t look for since they have the money to buy the perceived best the traditional way.

Now we’ve gotten to the root of the issue and that is what Billy Beane needed to solve for. The A’s have to think differently during free agency. Said another way,

“The world that we have made, as a result of the level of thinking we have done thus far, creates problems that we cannot solve, at the same level as the level we created them at.”

Attributed to Albert Einstein, but maybe Ram Dass

Luckily for the A’s, Beane was a rebel who is a quant as he was a fan of baseball writer and statistician Bill James’ theories of scientifically analyzing and studying baseball through the use of statistical data in an attempt to find answers as to why teams win and lose.

Billy hired statistician Paul DePodesta, and together they embarked on an analytical approach to creating a winning team that, in the end, changed baseball and all professional sports forever, even Formula 1®.

At the core of their analytics were Regressions and R-square. What I call marketers’ two best analytic friends. Step into the batter’s box and let’s explore these important tools.

Stay tuned for Chapter 4.

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Tim O’Connor

Rebel who’s a quant; CEO / P&L from $0/start-up to $300M+; 6 time CMO, including two billion-dollar-plus; founding team of 3 award-winning startups.