Questionable Leadership

~ by Randy Wagner

Why the Ability to Ask Penetrating Questions Matters

As we move from newbie to experienced in our careers, we’ve all been in a meeting where we are busy explaining something to management, only to have them ask some incisive question that completely alters the discussion and outcome. While there is obviously a need for knowledge and experience to get to successively higher management roles, it turns out the ability to ask penetrating questions has a huge impact on timelines and deliverable quality, and therefore, on a career.

The Five Ws in the Context of the Customer

One of the things I love about working at CastleBay is that management often asks questions that drive either at the core “W” questions (who, what, when, where, and why) or that provide a customer-centric focus. When I think about the best managers I’ve had in my career, I find it is those who ask great questions that cause me to re-evaluate the work and fine-tune deliverables.

The “W” questions often dig at our ability to deliver. Do we have resources available with that skill set? What are we really delivering? Can we even deliver what they want in this timeframe, or do we need to reset customer expectations? Where is one of those questions that’s subtle but brutal. Where does this functionality belong? Which environments will be impacted?

The Most Important W is Why

Most important though, is the why. Is the juice worth the squeeze? Who does this benefit? Sometimes it’s as simple as asking what is the cost of doing this versus not doing it? Is this an edge case that isn’t worth the cost of chasing?

The ability to peel back the work to understand what we’re really trying to achieve with the customer means understanding why they want something in the first place. The why can often drive the rest of the answers. Why? Oh, it’s a regulatory change, which comes with a due date, specific requirements to hit, and where those are applicable.

Are You Asking Yourself the Right Questions?

Perhaps most important of all, is developing the question skill within ourselves. If we can step back and genuinely ask these questions before we ever walk in that meeting with management, we can better tailor the pitch and address our own work on a day-to-day basis. Am I working on a problem that will take me five times longer to resolve than a quick work-around might handle? It’s easy to get too close and forget to manage ourselves. If you were your own manager, what questions would you be asking? That’s efficiency and that’s customer response.

The Art and Skill of Asking Questions is Valuable at Work and in Life

Asking questions helps us re-orient our work or the team’s work toward a path that makes the client successful and saves time. Management, especially senior management, can’t always get the visibility desired at every level of the organization. Great questions help keep the team on track. They often let you know in a single sentence the direction, importance, and context of the work. That’s good management. Technical skills come and go but the ability to ask great questions is valuable everywhere you go.

Randy Wagner is Director of Quality Assurance for CastleBay Companies. He has 20 years of consulting experience across private and public sectors, Guidewire InsuranceSuite, InsuranceNow, and Duck Creek, with specializations in quality assurance, project management, configuration management, and automation.