Asking Great Questions — Pt.1

Any leader worth their salt understands the true power of asking questions. It’s how you collect information. It’s how you define what work gets done. It’s also how you motivate people. With every question you ask you are setting objectives, identifying hurdles, and with the placement of each “?” you’re inviting others to join. It’s a craft we should all strive to perfect. Those who excel benefit not only themselves, but create opportunities for those around them to advance. In an effort to improve our craft we, at Uni, are breaking down the many aspects of what it means to ask great questions.

Tone-of-Voice

The words we choose matter. What you stand to gain from your question is tied directly to how approachable it is. Responses come voluntarily. Anything you can do to make it easier, faster, and more fun will help give you a better outcome. Farnam Street broke down Dale Carnegie’s 1936 classic How to Win Friends and Influence People into a 2 minute read. It’s the perfect refresher course on civility & etiquette for anyone who uses the internet. [spoiler alert] “Ask questions instead of giving direct orders” made the list!

In perfecting your tone-of-voice ask yourself…

• Is the tone of my question friendly and approachable?
• Have I used confusing jargon, shorthand, or abbreviations?
• Is my question short enough to keep someone’s attention?

Open v.s. Closed

Open questions are just better (generally speaking). They allow for the ideas that you haven’t anticipated. The phrase “How might we…” has become a popular default to ensure your question is indeed open, however any question can be phrased openly. Don Norman and Jakob Nielsen of NN/g put together a beautiful side-by-side list of open questions and their closed counterparts that their team uses when conducting research.

That’s not to say closed questions don’t have their time and place. By limiting the options to either “yes, no” or “a, b, c” you can dramatically speed up the process. The risk you face is not exploring your options fully and converging on a solution too early, which in the long run may cost you time. In addition, it’s extremely easy for closed questions to spontaneously deteriorate into their less-than-desirable cousin, the leading question. The very nature of defining a shortlist of options to choose from requires some amount of bias.

While shaping your questions ask yourself…

• Is the way my question is phrased open or closed?
• Should I be optimizing for speed or deliberation?
• How would I rewrite this question in the opposing format?
• Have I biased my audience by asking a leading question?

Broad v.s. Narrow

The trade-offs are simple. Broader questions take more time. Narrow questions may leave some opportunities unexplored. Deciding the scope of your question is often more reflective of your scenario than any overarching stragety. Still there’s a couple things you’ll want to keep in mind. First, be honest about your objectives. Think about what you are truly trying to accomplish and how you’ll measure your success. Have this top of mind while you’re word-smithing your questions. Second, clearly list all the constraints, but make addressing them optional. Your goal is to amass a large volume of ideas, some of which will inevitably be incomplete and imperfect. Steven Johnson, author of Farsighted: How We Make the Decisions That Matter the Most, agrees that the volume of ideas strongly correlates with making successful decisions. So unless you are truly in a time crunch, start with the broadest form of your question.

When defining the scope of your question ask yourself…

• What is my true objective in asking this question?
• What constraints are unavoidable?
• Have I made any unnecessary assumptions?
• How much time do I have before I need a decision?

Creative Constraints

Dry spells happen to the best of us. One way past them is by taking our questions and reframing them with new constraints. Rei Inamoto of I&CO does this with what he calls his Rule of 3’s. When presented with a challenge he simply asks “How would you solve this challenge if you were given 3 days? What about 3 weeks? Or 3 months?”. By adopting these imaginary constraints he and his team are able to open up questions in ways that would have never occurred otherwise. Taking on artificial timelines is just one of the many ways you can alter your approach to a question. The list of variables you can modify is endless. Consider a different budget,

During your next dry spell ask yourself…

• How would I solve this problem if given different resources?
• How would I solve this problem in a different culture?
• How would I solve this problem from the POV of a historical figure?

Sequencing Questions

The Socratic Method has shown us the power of sequential questioning. With it, we’re able to find clarification, challenge assumptions, uncover evidence, play devil’s advocate, explore implications, and probe why the question was even asked in the first place. While this method is unique in that it’s actually the students directing questions towards their teacher and not the other way around, it underscores the importance of breaking down complex questions into a set of individual challenges.

Once these smaller challenges have been identified, putting an order to them is then the next challenge. You have the opportunity to engage people in a narrative, choosing when to reveal new information or additional constraints. It’s an opportunity to build trust with those who are responding. Moving from broad to narrow, comfortable to difficult, or stable to risky. The important thing is that you’re conscious of the progression and use it to appeal to those who will be responding.

When thinking about the order of your questions ask yourself…

• What is the narrative I want to portray?
• What spectrum do these questions fall on?
• How do I want a participant to feel while answering?

Asking great questions is the job of great leaders, at Uni we’re dedicated to providing the best possible environment for these questions to be heard. With a better collective understanding of the dynamics & principals involved, we hope to establish stronger decision-making within organizations, and in turn promote a culture that is happier, healthier, with a better bottom-line. Start by asking great questions in your own future.