Todd Whittington: The power of asking why … Asking one ‘why’ question a day — and answering honestly — leads to greater understanding

The vast majority of my time these days is spent with young technology startup companies. These companies face overwhelming challenges with a multitude of uncertainties in all aspects of their operations model.

I help them remain focused on the simple truths that drive their business model, so as to not get buried with the complexities. The human mind has a limited capacity for conscious focus. In small teams, it is vitally important to reduce the work activity to a subset of the important activities — right action, right time.

Despite my manta of simplification, I was taken back when one of the founders of a company sent me a link to a TED talk by Simon Sinek that reminded me of the most fundamental of truths: The power of asking why. 

Breaking through assumptions

I’m not quite sure when I forgot to ask why. Twenty years ago, when I was working in the quality field on business process improvement, 5 Whys was a major component of the tool kit for Lean and the Toyota production system. The 5 Whys is a question-asking technique used to explore the cause and effect relationships underlying a particular problem. It also can systematically break through falsely held assumptions around legacy business practices.

Getting down to the nuts and bolts

Asking why is not just relegated to production processes, however; it encompasses the entire spectrum of business activity from the top down:

  • High-level strategy — Why are we in business? Why is our product/service important? Why are we changing/growing/shrinking?
  • Employees and partners — Why do you want to work with us? Why do we have these polices? Keep in mind that their reason may be different than yours. Understanding the differences in each person’s why is a key to successfully managing people. A lesson I learned many years ago when managing a call center was that my assumed motivations of my staff were completely different than theirs.
  • Marketing — Why are my customers buying? Why do they want to go to my site/store? Why are they willing to pay money? Why us and not our competitors?
  • Operations — Why are we doing this process? Why is this authorization needed?
  • Tactical  — Why is this key performance metric important? Why are we tracking these numbers, or not tracking them?
  • Founder/CEO motivation — Why is the work I’m doing valid?

Why is about getting to the underlying components. But more importantly, it’s about providing meaning and context to what we do. Obviously, what and how also are key in running a successful business, but the why should be central to our working life.

Underused, never overvalued

Do I sound obsessive with asking why? Maybe a little, but paradoxically for being one of the highest value activities, it is almost never systematically implemented — outside of Lean Six Sigma. I think the difficulty of asking why is that it is a little like introspection; with so much of our perspective outwardly focused, it takes extra effort to look inward.

As a practice for the upcoming year, I challenge you to ask yourself one why question a day, and seek an honest answer. I’m confident you’ll soon find a greater understanding of your business, your customers, your employees and, just maybe, yourself.


Todd Whittington has had a winding career path focusing around innovation processes, user acquisition marketing and operations improvement with a strong bent towards measurement and analytics. Whittington serves as the executive director for 10xelerator, the technology startup accelerator in Central Ohio. For more information, visit