The Art of Asking Questions

By Renae Oswald Anderson, Partner

I read with great anticipation the recent Harvard Business Review (HBR) cover story, “Ask Better Questions- the key to better strategic decision making.” SCC facilitates strategic planning for both large and small organizations and more than ever, our clients are thinking about their community impact post-pandemic: How do they create or sustain workplace culture while continuing to navigate a hybrid or remote workplace.

The SCC strategic planning team is trained in the ToP methodology from the Institute of Cultural Affairs. The ToP methodology allows for an inclusive and participatory process to gather the  wisdom and collective energy of the group in order to come to a consensus about  future strategic priorities or goals. Embedded in this model (and part of the HBR article) is the importance of creating and designing central questions—what the organization wants to know determines the important and central questions. 

The HBR article (read the article here with our compliments: https://hbr.org/2024/05/the-art-of-asking-smarter-questions) organizes the art and science of asking questions in five categories:

Investigative questions: What do we know? Probing deep enough to get beyond the obvious helps you identify and analyze the challenges or problems.

I for one have to work really hard at being patient with the process as boards and staff alike wrestle with digging into the heart of the issue. I am grateful for colleagues Cheryl Jensen and Imogen Davis who help me stay with the deep discovery process. HBR says, “Investigative questions dig even deeper to generate non-obvious information. The most common mistake is failing to go deep enough.”

Speculative questions: Ask “What if we did things differently?” “What else might work?” These questions start a future orientation that may often lead to change. Many of us embrace change if the change does not involve us or something we know or hold dear which is why the subjective questions are so important to round out the mix.

Productive questions: These help us answer, “Now what?” Does the organization have the capacity including time, talent, and infrastructure to do things differently?

Interpretive questions: These are the sense-making questions, “What did we learn?” “What are we trying to achieve?”

Subjective questions: These help us as facilitators to listen to what is being said or not said. Questions like, “How do you feel about where we have landed?” “Are there aspects of this plan that concern you?” I am fond of saying that “culture eats strategy for lunch.” These are the questions that get at organizational culture and can help identify the internal champions needed to accomplish the goal. Realistic yet aspirational strategic plans serve as the organization’s guard rails, inform the budget process and priorities, and provide accountability to staff and board leadership. Happy planning!!!

SCC would be honored to partner with your organization on your next strategic planning process. We are happy to have an exploratory conversation with leadership to discuss your needs, budget, and timeline.