Unlocking Valuable Insights: Mastering the Art of Questioning in Product Management

In today's rapidly evolving business landscape, product managers often face the challenge of extracting accurate requirements from stakeholders.

As a product manager working on a shipping software product and responsible for the tracking squad, my major stakeholders are our internal operation team.?

I faced difficulties eliciting requirements from experienced operations professionals due to I was a fresh joiner to the logistics complex industry and needed to deal with that.

This challenge attracted me because the logistics industry is still adopting new technology. Naturally, there needed to be more clarity between the vision of professionals in this industry and the vision of technology. I'm responsible for reducing this gap, and also, for the first time, I'm working in a team with a different work culture than my previous experiences.

In this article, I will explain my research and learning the art of questioning as a powerful tool to gain deep insights and shape the product roadmap. Drawing from my experiences in shadowing and pair-working with the operation team, we will delve into practical methods and strategies to master the art of questioning in product management.

First, I'd like to explain the practical tactics for framing questions from my point of view that I gained from researching, learning, and using.

• Contextual Understanding: Before you ask any questions, please take the time to understand the context in which your stakeholders operate deeply. Familiarize yourself with their workflow, challenges, and goals. This knowledge will enable you to ask more relevant and insightful questions that resonate with their experiences.
• Preparing Thoughtful Probing Questions: When engaging with stakeholders, prepare a set of probing questions in advance. These questions should build upon the information shared and delve deeper into specific areas of interest. You can uncover underlying motivations and comprehensively understand their needs by asking thoughtful, probing questions.
• Empathetic Approach: Show empathy towards your stakeholders’ perspectives and challenges. Frame your questions in a way that acknowledges their expertise and invites them to share their insights. This empathetic approach fosters a collaborative environment and encourages stakeholders to open up and provide valuable information.
• Visualizing Scenarios: Use visual aids like diagrams or prototypes to stimulate discussion and encourage stakeholders to provide feedback. Presenting scenarios or visual representations of potential solutions can prompt stakeholders to consider various aspects and articulate their preferences more effectively.
• Avoiding Leading Questions: Be mindful of avoiding leading questions that steer stakeholders towards a particular answer. Instead, focus on open-ended and neutral questions that allow stakeholders to express their opinions freely. This approach ensures unbiased feedback and fosters a more constructive dialogue.
• Active Listening: Practice active listening during conversations with stakeholders. (I think I’m not good at it yet!) Pay attention to their responses, non-verbal cues, and underlying concerns. This active listening will enable you to follow up with relevant follow-up questions and gain deeper insights into their perspectives.
• Iterative Refinement: Embrace an iterative approach to questioning. As you receive feedback and gain more insights, refine your questions accordingly. Continuously adjust your line of inquiry to explore new areas or clarify any uncertainties. This iterative refinement ensures that your questions remain relevant and aligned with the evolving needs of your stakeholders.

Also, I would like to mention a few tips about questioning techniques that I learned and found helpful.

• Open-Ended Questions: Use open-ended questions that encourage stakeholders to provide detailed responses. These questions often start with "what," "how," or "why." For example, instead of asking, "Do you like this feature?" ask, "How does this feature align with your workflow?”.
• Problem-Centric Questions: Frame questions around the challenges and pain points stakeholders face. This helps uncover their underlying needs and requirements. For instance, ask, "What are the biggest obstacles you face when managing logistics operations?" or "How does the current software solution fall short in addressing your specific pain points?"
• Goal-Oriented Questions: Probe stakeholders about their desired outcomes and goals. This helps prioritize features and align the roadmap with their requirements. Ask questions like, "What specific goals do you have for improving efficiency in your workflow?" or "How can our software solution contribute to doing your job faster?"
• Prioritization Questions: When discussing features or enhancements, ask stakeholders to prioritize their needs. This helps in understanding their preferences and ensures the roadmap reflects their priorities. For example, ask, "Which areas of your workflow would you like us to focus on first?" or "What features would have the most significant impact on your day-to-day processes?"
• Hypothetical Questions: Use hypothetical scenarios to stimulate stakeholders' thinking and gather insights. For instance, ask, "If you had an ideal software solution, what additional features or capabilities would you expect?" or "How would your workflow change if certain manual tasks were automated?"
• Iterative Questions: Emphasize the iterative nature of product development by asking stakeholders for ongoing feedback. This ensures continuous improvement and adaptation. Ask questions like, "How can we further refine the current features to meet your needs better?" or "What additional functionalities would you like to see in future updates?"

Remember, effective questioning involves active listening, creating a safe space for stakeholders to share their perspectives, and adapting your questions based on the context and the individuals you're engaging with. By employing these practical methods, you can extract valuable insights and shape your roadmap to deliver a successful product that meets the needs of your stakeholders.

In the end, I searched and used various resources to deal with my challenge and also wrote this article (even my previous and colleagues' experiences), but I highly recommend reading or even skimming these two resources if you are interested in this topic:

• "The Art of Powerful Questions" by Eric Vogt, Juanita Brown, and David Isaacs: This book provides a comprehensive guide to formulating and asking powerful questions in various contexts, including product management.
• "Questioning Skills for Leaders" by Andrew J. Bargerstock: This resource explores questioning techniques that leaders can use to enhance decision-making and problem-solving, which can be applied to product management scenarios as well.