Leading Through Questions
In many strategic decisions, the choices made depend less on past experience and more on how well the decision maker understands the problem. Experience matters, but it does not guarantee clarity. Even when alternatives seem straightforward, leaders may lack the perspective needed to make the best long-term choice. That’s why the burden of understanding falls on the decision maker to ask the right questions.
A leader with a strong engineering background may hesitate to make financial risk decisions that a financial analyst would welcome. A leader comfortable with people issues may struggle when the challenge becomes technical or data-driven. In uncertainty, the questions you ask become your most valuable tool.
Types of Questions
Different backgrounds lend themselves to different ways of thinking, processing, and reasoning.
Historians will think in terms of historical precedent and comparisons. Where have I seen this before in time?
Mathematicians often reason in terms of objective truth. What does the data tell and how does it inform our understanding?
Artists leverage their imagination to create new things. How might we reimagine this in a new way?
Broad, Open-ended, and Purposeful Questions
Powerful questions often begin broadly, are open-ended, and have a purpose. When approaching an unfamiliar topic, broad questions help sort information. Broad questions are often nonbinary and leave room for introspection.
Try these or improve upon them:
Why does this matter?
What is important about this?
What does success look like with this?
What is this like?
What is the desired outcome?
Powerful questions are also open-ended. Open-ended questions leave room for thinking by providing answers that go beyond a tactical response. These questions enable reflection and deeper thinking. The person asking the question remains curious, looking for one more response to wash the fog of uncertainty. The person answering the question can define the terms in their voice while being forced to provide understanding beyond their immediate perspective.
Consider these as well:
What can we learn from this?
How might we apply this in the future?
What are we not seeing?
What else could be true?
What other perspectives matter here?
Lastly, powerful questions often begin with “what” and “how.” These questions force the conversation partners to explore the purpose behind the question, which enables systems, choices, and meaning. Additionally, “what” and “how” questions naturally move the conversation forward by connecting the mechanisms behind the answer to the question being posed. The response naturally offers a description of the process behind the unknown. For the person asking the question, this may set the conditions for new and original ways of seeking understanding through more questions.
Consequently, to ask the most beneficial questions, it is important to recognize how you learn and take in information. Do you learn by repetition, doing, or observing? Used with the right goal in mind, questions can create a new road map for understanding based on your learning style. But asking random questions without a desired outcome risks further confusion. That said, there is an exhaustive list of questions one might ask. But I consider the approach listed above as foundational to bridging the gap between confusion and clarity.
From Doer to Generalist
Kendra Brooks juggled many requirements as she settled into her new role as the Sr Director of Operations for her firm. She was an experienced project manager who now found herself in the C-Suite, given her drive and business acumen over the last fifteen years with the firm. Her role was no longer the expert of her modernization portfolio. She would now serve as a generalist providing leadership and oversight across several divisions that she had only worked tangentially with before.
Kendra began a careful review of her schedule. Her first meeting was an overview of the Artificial Intelligence initiatives for the next three years with the AI division lead. Unfortunately, Kendra was not familiar with large language models or their applications beyond her personal use. Kendra felt uncomfortable and out of her league initially.
What she did know this:
She didn’t need to become the expert.
She needed to seek understanding.
She needed to guide the AI lead toward the board’s strategic vision.
The AI division lead walks in and said,
“Our generative AI technologies have the opportunity to explode into mainstream consciousness with this new approach to user interface…”
Leadership Reflection
What is one powerful question you can ask this week to gain clarity on a decision that matters?
