Am I Asking the Right Questions?

Lupe Poblano

We’re excited to welcome our newest practice member Lupe Poblano to the CompassPoint fold – and we’re equally excited to share his first blog for us on the topic of inquiry and its importance as a leadership tool. Lupe joined our practice in early July, though the guidance in this post align with CompassPoint's leadership approach like he’s been on staff for years. He’s clearly at the right place. 


“Human systems grow in the direction of what they persistently ask questions about.” – David L. Cooperrider

I spent the past nine years working for a wonderful organization: Habitat for Humanity Greater San Francisco. At various times during my tenure I was responsible for organizational budgets, delivery of programs, helping to lead a merger, spearheading a social entrepreneurship venture, and managing experienced teams and individuals. The stakes often seemed high, the challenges complex, the demands urgent, and time scarce. And while I had the privilege of partnering with incredibly talented and gifted individuals, people whose contributions on the above projects often dwarfed mine, I always felt a lot of pressure. From a place of positional leadership, I put a tremendous amount of pressure on myself to always do the “right” thing, or have the “right” answer, or make the “right” decision. As I saw it, it was my job to come up with the correct solutions whenever barriers, problems, or challenges crept in.

Since then, I’ve transitioned to another great organization, CompassPoint, and I’ve been thinking a lot about the importance and power of asking questions. Now that I work with leaders in a different capacity (more from a training, consulting, and coaching lens), I can see that they often put a similar pressure on themselves to always be correct, and to always make the right decision.

The Value of Inquiry for Leaders

As I reflect back on my Habitat experience, I realize that the times I was the most disappointed in my own performance were not when I made a bad decision or didn’t have the “right” answer—but rather when I didn’t ask the right questions. Without asking the right questions, of either myself or others, sometimes I moved into solution space before I became totally clear on what the problem actually was. Or maybe I just focused on the presenting symptoms instead of asking about root causes. When I did ask questions, they were not always the right ones. Too often I would ask tactical or checklist-type questions without using the power of inquiry to drill down deeper.

I wish I had asked more insightful questions such as: How is my leadership showing in this instance? What is the problem we are really solving for here? Is this an adaptive challenge or a technical one? What am I doing as a leader that is inadvertently contributing to the problem? How has this team been successful in the past and can we translate that experience into this challenge? Are we leveraging our collective strengths as a team? What organizational conversations are not happening that should be happening, and what can I do to facilitate them? 

These were the questions I wish I had asked more often. The times that I was self-aware enough to take a step back, exercise patience, and ask these challenging yet necessary questions, I knew that I was moving our collective thinking forward—orienting us in the right direction. With the perspective of time and distance, I realize I was often at my most powerful and effective as a leader when I was asking the right questions, and not necessarily when I was the most knowledgeable or decisive.

Inquiry-based Frameworks

Asking the right questions is key to making sure you have the information you need in your decision-making role. Additionally, there are many ways that we as leaders can ask the right questions and create a culture of inquiry and curiosity within our organizations to move us forward. Here are three examples that leverage the power of asking the right questions.

Appreciative Inquiry (AI). AI is a great way to use the power of inquiry to discover the bright spots of an organization. By determining what is working (instead of focusing on what is not working), AI can ignite organizational strengths to unleash change. The father of Appreciative Inquiry, David Cooperrider, writes “AI involves […] the art and practice of asking questions that strengthen a system’s capacity to apprehend, anticipate, and heighten positive potential” (Cooperrider, David and Whitney, Diana. Collaborating for Change: Appreciative Inquiry. Berrett-Koehler Publishers. 2000). In other words, positively framed questions can lead to positive results.

Coaching. Coaching can be used as a tool to unlock the decision-making potential of others within your team and organization. Again, the key is in asking the right questions. By utilizing open-ended questions instead of one-way directives, “managers who use the coaching approach with their staff help them to develop their thinking, find new possibilities, and grow their abilities” (Gislason, Michelle and Wilson, Judith. Coaching Skills for Nonprofit Managers and Leaders. Jossey-Bass. 2009).

Evaluation. We often think that evaluation only means collecting the right information about the impact of our programs, but it, too, starts with asking the right questions. As Steve Patty articulates in his book, Getting to What Matters, a great question to start from when thinking about programmatic evaluation is: “If you could know something—anything—to help you be better at what you do and cause greater impact in the people that you serve, what would you want to know? If something could be known more fully, more deeply, more insightfully—even if it couldn’t be known absolutely or completely—what would you want that to be?”

I’ve been guilty of internalizing the burdens and expectations of positional leadership to mean that I had to have all the answers. I suspect that I am not alone in this type of thinking. However, I realize now that while I cannot always control the outcomes of decisions, I can control the types of questions that I ask. The power, therefore, is in the question, not the answer. 

What do you think?


Lupe Poblano, MS, is a Project Director at CompassPoint. Most recently Lupe served as the Director of Evaluation, Learning, and Strategy at Habitat for Humanity Greater San Francisco. You can reach him by email. Follow him on twitter at @LupePoblano. 

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