The Art (and Power) of Asking Good Questions

I’m reading the book The Innovator’s DNA. It describes 5 key attributes exhibited by disruptive innovators, one of which is a “passion for inquiry”. Innovators are skilled at asking questions. The authors also relate how Apple, Inc.’s Chairman of the Board Steve Jobs states that the “beautiful typography” introduced on the Macintosh may not have been created if he hadn’t dropped-in on a calligraphy class at Reed College ten years earlier (after having already dropped-out of Reed College). This ability to connect seemingly unrelated ideas and experiences is another key element in the DNA of innovators.

Steve Jobs tells the story himself in his 2005 address to the graduating class at Stanford University. I encourage you to take 15 minutes out of your day to watch the 3 stories Jobs tells in this video, but if you are impatient you can hear the calligraphy story in the first 5m30s.

Now, I should probably know better than to try to hold your interest after you just watched the consummate innovator dispense his wisdom. Especially when my story involves dirt, tractors, farming and making a big mistake because I didn’t ask the right questions.

I once worked from sunup to sundown plowing the wrong field. A field that belonged to somebody different than the person paying me to plow his field. A field that may or may not have needed to be plowed, or to be plowed at that particular time or in that particular way. Now to my credit, I performed high quality work. Unfortunately, as Peter Drucker observed: “There is nothing quite so useless, as doing with great efficiency, something that should not be done at all.” How did I go so far afield? (ok, let me apologize right now for that pun, but stay with me…)

Western Kansas has a reputation for being a flat expanse of nothingness stretching to the horizon in every direction. This is largely due to the fact that Western Kansas is a flat expanse of nothingness stretching to the horizon in every direction. The Great Plains stretch from the Front Range of the Rocky Mountains all the way across Kansas and is practically laid out in a perfect grid. Each 1 square mile of land (commonly called a “section”) is bordered by roads that align perfectly in a North/South or East/West direction. Some good representative photos can be found here.

Due to this perfectly aligned grid layout and an always clear view to the horizon, directions from one place to another are always given in cardinal points: drive 2 miles North then turn West for 6 miles until…

Landmarks are often thrown in for reference, to offer some reassurance that you are on the right track. Things like “you’ll cross a bridge and see a windmill on your left” or “you’ll see a row of trees on the corner”. Now, there aren’t many places where a tree can be used as a useful reference point while giving directions that might span dozens of miles or more, but if you have been to Western Kansas you know just how useful this can be. There aren’t many trees to be found out there. In fact, in the town where I grew up, probably every single one of the 1000 residents knew what you meant when you referred to “The Tree”. Arguably this had a lot to do with the fact that The Tree was precisely one-quarter mile from a specific intersection, and on Friday and Saturday nights it could be turned into an impromptu racing strip for testing the latest modifications of those lucky enough to own a (now Classic) muscle-car. That it served the same purpose for many previous and subsequent generations made it legendary. Measuring your 1/4 mile time and speed was practically a right of passage into adulthood. But I digress.

That background was needed to introduce the setting that caused me to waste valuable time and resources, all because I didn’t ask questions. In my previous post I made the case for the importance of understanding the real business requirements. This story demonstrates what can happen when the business requirements are precisely specified but the execution team doesn’t take the time to fully understand them. When neither side asks the right questions the result is wasted time, effort and resources.

Events unfolded something like this:

FARMER BROWN: “Take that Ford 5610 tractor and the 20-foot sweeps and work that quarter-section across the road from the old Jones place. No need to put down anhydrous this time, we’ll do that in a few weeks. To get there turn North out of the driveway up to the next intersection. You’ll see an old rusted-out stock tank there on the Southwest corner; turn West there and go 2 miles, and just after you cross the bridge there is a shortcut on the unmaintained road heading south. After about half a mile you’ll see a windbreak of pine trees by the house where the Smith’s used to live. Turn back West there and cut through the draw and follow it until you cross the creek. On the other side of the creek you will see the windmill on the old Jones place on the other side of the road. Sweep that quarter section on the East side of the road. OK?”

SOB: “Ummmm… Uhhhh, OK”

At this point one of us should have asked some questions. Me because I was unlikely to remember those directions, and him due to my tentative response and what I’m sure must have been a look of utter confusion on my face. I don’t really know why I didn’t ask for written directions or for him to take 10 minutes to lead me there, but I didn’t. Probably I was afraid of looking stupid (you can guess how that worked out for me at the end of the day). Instead I convinced myself that I understood the directions and could carry them out.

A hot August day in Kansas can easily exceed 100 degrees, and these are the best days for killing weeds – for “sweeping” a field. In later years I was fortunate enough to operate a 600 HP 4-wheel drive tractor with a full cab outfitted with cold air conditioning and an FM radio (not so much different than a day at the office, a 600 HP office). In this instance I wasn’t so lucky. I was operating a tractor without a cab, doing a dirty job involving real dirt. Imagine the experience from the photo below, only sitting unprotected inside the cloud of dust under the pounding hot sun.

You can imagine then that this was a hard-won lesson for me.

In spite of the dirt, the heat, days that could have 16 hours of workable daylight… there was something I loved about plowing a field (or even better, planting or harvesting). Partly it had to do with being able to visually see the result of your effort, to have a perfectly clear objective, to see the steady rate of progress you made, and to behold the final result. There is hidden beauty in Kansas, in spite of it’s well deserved reputation for being very flat.

Creating software has these same payoffs in a way (but with a much higher failure rate of plowing the wrong field as it were). Delivering a product to the market and seeing your product do something tangible, whether it is connecting an emergency call or merely tossing an unhappy bird, is the big payoff. It’s what attracts people to this business. Well, that and the clean, comfortable working conditions, and the chance to become a billionaire. Seriously though, it is a passion for creating things that motivates developers, and this is what drew me into this field. (Sorry, no apology for that pun – it’s kind of subtle).

Asking good questions – the right questions at the right time – is invaluable in both problem analysis and resolution as well as in guiding project execution efficiency. Don’t be afraid to ask questions. Better to risk appearing stupid by asking a question than to deliver the wrong result and remove all doubt.

Also be willing to ask fundamental questions like ‘why does it have to be done that way’, or, ‘what would happen if…’. Such questions will bring you to the frontier of innovation.

Wow, even after trimming some material this was a really long post. If you made it here to the end you are either a blood relative or just very persistent. In either case thanks for reading.

By the way, it was interesting to me to hear Steve Jobs describe his working-class upbringing and that he was not the product of wealth and privilege. All the more inspiring.



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