How to ask better more productive questions

You’ve heard the advice, and probably followed it too: Always ask open-ended questions and never limit yourself to Yes/No answers.

It’s well-intentioned advice, but it’s wrong.

I ask questions for a living. It’s part of my job as a sports broadcaster. After thousands of interviews, I know firsthand that open-ended questions create confusion, and “yes” or “no” can be the most accurate and powerful answer. I also know that asking more intentional and strategic questions leads to better listening skills and more productive conversations.

Harvard researchers have pointed to the importance of asking questions as a way to become more likable and build relationships. What the research fails to consider is this:

1. Our standards aren’t high enough.

2. We spend too much time asking lazy questions and not enough time strategizing the best questions.

There’s no better example of this than a question we ask and answer multiple times a day, “How are you?” It’s a conversational norm and something we include as part of a standard greeting. It’s also a terrible question despite being open-ended. I bet you never stopped to consider how many ways there are to answer that question because most people offer up a single word like, “Good,” “Fine,” or “Great.” Satisfied we got a response, but with no real information, we move on, often awkwardly, to the next part of the interaction. It’s an exchange with no real communication.

It doesn’t have to be that way.

You can improve that interaction and every conversation you have at work by doing these three things.

Determine your objective

Be as specific as you can. Getting to know a candidate is different than determining if that candidate has the resiliency to manage the inevitable change they’ll experience in a startup culture. Going into a conversation and hoping the answers will reveal themselves puts a lot of stress on you and a lot of pressure on the other person. It’s how we end up asking “How are you?” and then getting stuck when we don’t get an interesting response or a response that furthers the conversation. If you don’t know what you’re trying to accomplish, you can’t expect anyone else to know either.

Ask focused questions

Here’s the real problem with “How are you?” It’s too broad. It creates confusion when what you should be creating is a comfortable conversation track. The reason most people opt for a one-word response to that question is that it’s the safest response.

Sure, they could talk about a project they’re working on, the pressure they’re under at work, their kids’ soccer tournament, or the fact that they’ve stuck to their workout routine for an entire month, but they won’t because there’s no indication that’s the answer you’re looking for. No one wants to put themselves out there, become vulnerable, and risk sharing too much without the assurance that’s what you expected to hear.

Asking focused questions gives people permission to give you the real answer. Focused questions also help you reach your objectives. Why do you want to work at this company? Could become, “What’s the skill you’ve developed in the last five years that you think can be most impactful here?” If you’re determining if a candidate has the resiliency needed for the position, “How did you handle a challenging situation?” Could be, “How did you show grit in dealing with a challenge?”

Instead of asking “How are you,” choose a specific topic, subject, or emotion.

  • What are you most excited about today?
  • How are you managing the additional workload?
  • You’re not smiling as much as usual. Are you doing okay?

It seems counterintuitive, but limiting the potential responses and asking more focused questions leads to not just better answers, but real answers. And when those questions are tied to meeting a specific objective, you’ll be a more attentive listener because you know exactly what you’re listening for.

Utilize Yes/No questions

Speaking of counterintuitive, Yes/No questions, while taboo according to conventional wisdom, are the best way to stay in the loop and get actionable feedback. Think about how many times you’ve sent an email with this closing line, “Let me know what you think.” What’s your average rate of response? Does asking the question, “What did I miss?” actually lead to pertinent information or a lengthy exchange that just wastes everyone’s time? It might sound more accommodating and conversational to keep things open-ended, but as we’ve already seen, it won’t lead to real answers.

When you need a real answer, give people fewer options. Instead of, “What did I miss?” you could ask, “Did you already discuss the new marketing rollout?” “Let me know what you think” becomes “Does the scope of the proposal fit your budget?” Instead of asking a new hire, “Did I cover everything?” try, “Do you feel confident you have enough information to get started?”

Better communication starts with asking better questions. It’s a game changer in gauging employee satisfaction, interviewing candidates, onboarding new hires, and getting to know coworkers you haven’t seen in person for nearly two years, if ever. Taking the time to think through the conversation from both sides will help you identify roadblocks in the conversation, reduce confusion, increase communication, and ask better questions.

Jen Mueller is a 20-year sports broadcasting veteran based in Seattle, Washington, and the founder of Talk Sporty to Me.