An executive met a networking lunch partner, who was well connected in the career field that the executive wanted to explore. His contact genuinely wanted to be helpful; yet, no real leads came out of the conversation.

As he began to dissect the conversation and figure out what he could have done differently, he realized: he hadn’t been asking the right questions. It dawned on him that he had experienced a missed opportunity, one he could have capitalized on if he knew how to ask better questions.

Whether you’re happily employed or currently seeking your next opportunity, there’s one skill you need to get better results from your efforts: the art of asking better questions. Smart, targeted, insightful questions bring you key information you need to get ahead. If you can learn the way to ask better questions, you can:

  • glean the insight you need to be more creative
  • gain buy-in from others
  • cement your professional brand as someone who thinks beyond what’s currently happening
  • find out data/information that might not otherwise be available to you
  • shift from consumption mode (taking in/being shaped by other people’s ideas) to proactive mode (using your great questions to guide what might happen next)
  • form better relationships by showing an interest in other people’s ideas
  • you help your contacts feel like they get something out of the conversation
  • gain impact on decisions that affect you

What’s wrong with the questions you’re currently asking?

In the case of this executive, he hadn’t prepared well for the conversation and went in with questions that were too broad. To his credit, he had done some work beforehand by looking up the person’s profile on LinkedIn, but otherwise he went in with an unplanned conversational approach. He asked questions like “What ideas do you have for me for companies to look into?” and “Do you have anyone in your network who might be a good contact for me?” Although his contact took the questions seriously, the inquiries didn’t open up any new possibilities for my client because they were too generic.

The anatomy of a better question

Great questions help you advocate for yourself and get better results; they help you organize information, and they help you build relationships. Great questions come from an awareness of what we don’t know, which requires first that we identify what information gaps we have and what we need to learn. One we know what we don’t know, then we need to create a strategy for how to gain that information.

Here’s how to ask better questions

First and foremost, you need to make a plan for your questions. Unlike my job seeker client, don’t assume you can wing it and get the insight you need. When planning what you’ll ask, here’s how you know you’re asking the right questions:

  • The right person: I’ve mapped out the information gaps I have, in advance, and this is best person who can help me fill in that information void
  • The right intent: I’m genuinely curious about the topic (I’m not asking it to LOOK smarter, I’m asking it to BECOME smarter)
  • The right preparation: I’ve become as informed as I can about the topic before asking the question. I’m not depending on this person for rudimentary knowledge that I could easily gain on my own
  • The right information gap: I don’t already know the answer (or I need clarification on something)
  • The right size of the question: Should it be broader (“What are the larger trends in the industry that you’re hearing about that I should make sure I can speak to”)? Should it be narrower (“I’m focusing on XYZ company, do you know anyone there”)? The best conversation has a mix of both kinds of questions.
  • The right number of questions: I have a curated list of the best questions I can ask this person so I’m taking up the right amount of the person’s time
  • The right outcome: I have a clear understanding of what outcome I want after asking this question, and my question clearly leads us to that outcome. Am I seeking broad industry information? A specific list of contacts? A particular introduction to a particular person? A recommended resource for more learning? Etc.

This executive would have gotten much better information had he come prepared with more information, had some broad and some narrow questions, and gotten more clear on exactly what help he was hoping the person could provide.

For example, if he had taken the extra step of researching his contact’s contacts on LinkedIn, he could have asked for specific introductions based on that research. He could have brought a list of the kinds of companies he’s targeting, and handed it to the person to peruse and potentially suggest contacts in those or very similar companies. He could have more specifically thought through his contact’s career history and domain expertise, and drilled down into narrow, tailored questions (“you know the healthcare space well, where might my technology integration experience fit best in that domain? Who’s doing these kinds of projects?”). And he could have shared his particular desired outcome (“I thought I’d reconnect with people I respect; out of this conversation, I’d love to get your insight on three target companies you think might be interesting for me to research next week”).

Improve your questions and you’ll improve your career

Improving your question-asking leads to a much better outcome from the conversation, but also a better future relationship with your contact, who also wants to feel that the time spent meeting you is productive.

Asking great questions is a lifelong career skill that will help you across the career lifespan, from investigating possible careers to learning whether or not a company’s a good fit for you, and then once you’re inside, becoming a better contributor and leader. If you use this framework to think through your questions ahead of key meetings, you’ll get the help you need from others to make better progress in your career.