7 Strategies for asking effective questions

This post originally appeared on Medium

Flashback to Mrs. Eckhart’s sixth grade classroom in small-town Iowa. The lesson for the day: Where do storms come from? The teacher opened the floor for questions and a small, pale boy with brown hair raised his hand: “Why does the sky look green when a storm is coming? And what makes the hail? Is that the same thing that causes wall clouds?”

“Paul, why don’t we give someone else a chance to ask questions,” Mrs. E replied with a slight bite in her voice. I must have driven her crazy.

I’ve always loved asking questions. Maybe that’s why I gravitated towards the field of evaluation and impact analytics. But, I was never really trained in asking questions effectively. And you probably weren’t either.

A few weeks ago, I published a post about how to ask better data analysis questions. Now, I’d like to share a few tips for asking better questions of your coworkers and clients to solve problems and understand impact.

1. Choose the Right Time and Place. 
If your question would take five minutes or less to answer, give someone a call or stop by their desk. For longer discussions, set up an appointment. For executives, ask their assistant or direct reports about their communication preferences, so you can choose the best time and place to get your question answered.

2. Prepare.
 Don’t hold a conversation with a client or colleague until you’re crystal clear about your intended outcome. Then, create a discussion guide that you can follow when talking about the problem you’re trying to solve or question you’re trying to understand. The questions in your guide should start general and then become more specific. You may want to mark the three most critical questions to be sure you cover them if the conversation wanders.

3. Provide Context
 You will naturally want to dive right into the nitty-gritty details. For example, your real question may be, “Why is it that 5% of the case notes we record indicate the client “attended” a session, but the session length was only 1 minute?” Don’t lead with this. Make sure the person you’re talking to understands the purpose of the conversation before asking detailed questions.

One tip I learned the hard way is to respect power dynamics when setting context at the start of a meeting. If you’re not the most senior person in a group discussion, give that person the opportunity to kick things off. Once everyone at the table knows the purpose of the meeting and why you’re asking questions, then you can dive into the detail.

4. Balance Macro and Micro Questions. 
 Chances are you’ve been aggregating questions about a particular subject. When presenting these questions to clients or colleagues, start high level. I find a basic opening question along the lines of:

  • “Walk me through how you do…?”
  • “Tell me about your experience with…?”; or
  • “What do you want to see happen when…?”

…often gets me 80% of what I need to know. And sometimes these broad, open-ended questions have led me to learn things I didn’t even know to ask!

5. Ask Follow-up Questions.
 Surely there was something interesting or unexpected in your interviewee’s answer to the initial broad questions. Trust your gut and follow up on it, especially if you suspect there might be more to the story than they’re letting on. Don’t just take my word on this — author and consultant Peter Blockprovides some great tips on how to behave authentically in critical conversations.

6. Acknowledge Feelings.
 Some of the most useful follow-up questions I ask are around exploring others’ motivations and reactions to their circumstances. Presumably, this challenge or question has existed quite a while. Consider the following questions:

  • Why is now is the right time to tackle this question or problem?
  • How does not knowing the answer make other staff and clients feel?
  • What are other people in the organization (or even your interviewees) doing to perpetuate the problem?
  • Despite the problems, what’s been working well?

7. Manage Cadence.
 Pay attention to the cadence of the interview. Some people ask and answer questions aggressively, talking over others like they’re placing a trade on Wall Street. Others treat an conversation like a therapy session, requiring a lot of silence before opening up. Learn to read the cadence of an interview quickly and match your style to your interviewees to maximize the amount and quality of information you get.

Finally, remember that it’s up to you to engineer a good ending to conversations exploring important questions or problems. Regardless of what happened, give genuine thanks to those who shared their knowledge and experiences. Acknowledge the fact they had other priorities, and share with them what to expect from you or others next.

For me, asking good questions is a critical skill for those trying to build data-literate and impact-literate teams. Do you have other questions about how to promote data literacy in your organization? I’ll respond directly to any comments and also include your thoughts in my next post.