How to Transform Good Questions into Great Ones

How do you improve a fair or even a good question—possibly turning it into a great one?

It takes hard work to come up with really strong questions. In this newsletter I’d like to give you a set of criteria and a process that will make it a lot easier for you.

Here’s how it can work for you.

First, imagine this scenario: You’re meeting with a senior executive, Deborah, who has just been hired from the outside to take over as the SVP in charge of a major function. You’ve asked for a meeting with her to introduce yourself, establish a relationship, and create the basis for some possible future work together (her position is almost irrelevant—it could be CFO, CMO, CEO, CHRO, CIO, General Counsel, etc.).

So what do you ask her in your meeting?

Below, I’ve set out a list of the key characteristics of a power question. Not every power question has to have all of these, but they should all have some of them.

For each criterion, I’ve provided ideas to help you sharpen your questions, with this scenario in mind: You’re going to meet with a new top executive who was hired from the outside.

Here goes. Keep in mind that my alternative questions are just illustrative—you’ll have to adapt them/the approach to your particular clients and their issues.

Criterion One: Power Questions are open-ended. For example:

Instead of: “Have you enjoyed your first few weeks with the company?” (To which the client can simply answer “Yes” or “No”!) or “How long have you been on board?”

Try asking: “What have you learned in these first few weeks since you started?” or even simply, “What attracted you to the company?”

Your strategy: Always work to create an open-ended version of a closed-ended question. Minimize informational questions when meeting with a senior client executive.

Criterion Two: Power Questions are fresh and interesting—even surprising. For example:

Instead of: “So, what will success look like?” (Which is, honestly, overused and clichéd”)

Ask: “What process are you using to set your short- and long-term priorities?”

Your strategy: Don’t simply use the first question that comes to mind. Think about a question no one else is asking, or rephrase a common question in a new, fresh way.

Criterion Three: Power Questions help you get “under the skin” of your client and draw out their most important issues and concerns. For example:

Instead of: “What are your top priorities for the next six months?” (It’s an overused question, and in any event some senior clients won’t reveal this to you unless they already know you pretty well)

Ask: “I’m curious, how is your new push into emerging markets going to impact your investment priorities in the coming year?” (That is, draw their issues out by asking a series of implication questions). Or, “What are the key performance objectives that your leadership has established for you and your role this year?”

Your strategy: Consider multiple approaches to drawing out the other person’s real agenda. You can do this by asking implication questions (e.g., “How are you reacting to…”), and also by asking a more specific question (e.g., “In which areas would you give yourself an ‘A’ grade today, and where do you wish you were making faster progress?”). Another one I like is, “Among all your various priorities, which ones are you personally most engaged in?”

Criterion Four: Power Questions show thoughtful preparation on your part. For example:

Instead of: “Can you tell us about your strategy?” (Yes, a CEO once told me this was the exact question two partners from a major consulting firm opened up with after having cold-called him…)

Ask: “I noticed in your 10K that you’ve taken a somewhat unorthodox approach to the long-term compensation of your top officers. Can you share your thinking behind it?” Or, “I’m familiar with the broad outlines of your CEO’s new, four-point strategy that was announced on the recent analyst call. How will this impact your own programs going forward?”

Your strategy: Prepare, but prepare selectively. You don’t need to create a 30-page briefing deck that reviews every aspect of your client’s operations. Instead, scan the background information and pick two or three areas you may want to probe. Remember, all you need are one or two really good questions to fuel a high-impact conversation. If you have to spend hours preparing for every single meeting, you’ll never make the connections you need to build a strong, diverse client base.

Criterion Five: Power Questions make the other person think and reflect deeply about their issue and the solutions they are considering. For example:

Instead of: “This sounds like a very interesting program…when would you like to launch it?” (Don’t accept the client’s problem or solution definition without some additional probing!)

Ask: “I’m curious, why did you decide to launch this particular program, now?” or “What business goals is this program going to help support?”

Your strategy: Ask questions that help you understand higher-level goals and strategies. Often, this is a “Why?” question. Keep in mind Sakichi Toyoda’s exhortation to his engineers at Toyota to ask “Why?” five times about any quality or manufacturing problem! Remember, a particular program or initiative is just one way of accomplishing a higher-level goal—there might be other, better ways.

Criterion Six: Power Questions tap into emotions and personal implications as well as ration/analytical dimensions of the issue. For example:

Instead of: “What do you think about this approach?”

Ask: “How do you feel about this approach?”

Instead of: “Who are the key stakeholders for this program?”

Ask: “How will this program impact your own roles and responsibilities?”

Your strategy: Come up with “Dreams” and “Fears” questions for your clients. “Dreams” questions focus on dreams, aspirations, personal legacy, etc. “Fears” questions touch on fears, risks, pitfalls, concerns, and so on.

Criterion Seven: Power Questions build your credibility by showcasing your implicit experience and knowledge. For example:

Instead of: “How are you spending your time?”

Ask: “When some other clients of mine have taken a new role like yours, they’ve often spent their first few months in three areas: building their internal network, developing their strategic priorities, and assessing their team. I’m curious, what have you been focused on?”

Your strategy: Ask “Credibility-Building” questions that implicitly build your credibility by stating an observation and then asking a question.

In summary: When you prepare your questions for an upcoming meeting, use this process:

  • Review your question against each of these criteria. Does it meet two or three of them? What changes in would make it better align with the qualities of Power Questions?
  • Think about ways to sharpen each question using the strategies I’ve outlined.
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