Question behind the question

Your ability to answer questions is a competitive advantage. Here’s how to uncover the deeper underlying question.

Image: Midjourney

👋 Hey, it’s Wes. Welcome to my weekly newsletter where I share frameworks for becoming a sharper marketer, operator, and builder. If you’re not a subscriber, here’s what you missed this month:

• Strategy, not self-expression: How to decide what to say when giving feedback

• WTF does it mean to “act like an owner”?

• Rigorous thinking: No lazy thinking

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Answering questions is higher stakes than most people realize. The secret to increasing your effectiveness is to consider the "question behind the question” (QBQ). In this week’s newsletter, you’ll learn:

• Part I: How to address the question behind the question

• Part II: How to probe for more information

• Part III: If you’re asking the question, share the QBQ

I originally published a version of this essay in November 2019. Since then, I’ve expanded the post. Enjoy.

Read time: 10 minutes

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Given the number of times you are asked questions every week at work, having a framework for answering well is a highly leveraged, organic way to show your credibility.

When you consider the “the question behind the question” (QBQ), you'll answer more confidently and your audience will feel more satisfied with your reply.

Why the question behind the question matters

First, what is the question behind the question (QBQ)? When someone asks you a question, there's the surface question—but there is often a deeper layer. It's usually something the other person is trying to uncover. It could be a deeper worry, concern, or curiosity.

Until you address the question behind the question, your audience won't feel like you fully answered their question. A few signs you should address the question behind the question:

• You have to repeat yourself multiple times

• There are more follow-up questions than usual

• The person still seems skeptical or doubtful

• They’re asking questions you believe are irrelevant or you’ve already answered

These are clues that, for whatever reason, your original answer wasn't satisfactory. So what should you do?

Most of the time, the question behind the question is subconscious—the person might not even know why your answer doesn't seem good enough. They’re not intentionally being coy, and they're not asking one thing secretly wanting to know something else. Give them the benefit of the doubt and treat their questions as valid.

Part I: How to address the question behind the question

Avoid engaging in never-ending back-and-forth

When you sense that your original answer isn’t landing, don’t blindly engage in a never-ending back-and-forth because it’s a drain on both sides.

Step back and think about what their true concern might be. For example, they might be looking for reassurance, better logic from you, or a different type of evidence than what you’re sharing. If your answers aren’t landing, don’t only do more of the same—instead, consider adjusting your approach.

If you know the person

Your manager asks, “How is X project going? Is everything under control and is there anything I should be aware of?”

You could answer a question like this at face value with a short and generic reply, but that's a missed opportunity. Instead, answer with the question behind the question in mind. Your answer depends on a few factors: 

• What might feel risky for them?

• What would make them feel reassured and safe?

• What would make them confident that you've got this?

For example, let’s say your manager is a numbers person. They usually want to see qualitative and quantitative data, including numbers, trends quarter-over-quarter, data pulled and cross-checked from different sources, and logic to tie it together. Your answers should include details they care about.

Bad reply:

“Yep, everything is good. I’ve got it under control.”

This answer could work if your relationship is high trust, the project is low importance (and therefore low cost if you mess up), or your manager is already sufficiently in the loop. Otherwise, this is too generic of an answer. They will keep asking until they feel you’ve given them enough evidence to believe you.

Good reply:

“Yep, everything is good. I reviewed our numbers this morning. We’re tracking along to forecast as expected. [Insert data points] I’m monitoring the progress a couple times a week and will flag if anything changes. If there's anything else you’re curious about, let me know and I'm happy to share more.”

This works because it’s tailored to your manager’s concerns. It goes beyond their original question to answer the question behind the question (QBQ).

If you don’t know the person

When you don’t know a person, it’s not always practical to ask directly for clarification about the question behind the question. If you hint at the idea of “What are you really trying to ask?” or execute poorly when bringing it up, you risk insinuating that the person has ulterior motives.

What you can do is form a hypothesis about what the person would find valuable. For example, I use proxies like their function, our dynamic, the context in which we’re meeting, and what someone in their role is usually curious about.

• Speaking with journalists: When you’re speaking with journalists, they’re generally looking for newsworthy events or spiky points of view that are relevant to articles they’re working on. Ideally, they would like you to divulge juicy information you haven’t shared elsewhere so they have the scoop. The question behind the question might be: “What is newsworthy and quotable here? What can I use for the story I'm writing?”

• Interviewing job candidates: When you’re interviewing candidates, you might save 5-10 minutes at the end for them to ask you questions. Regardless of what they ask, they’re subconsciously asking this QBQ: “Should I hitch my wagon to this manager and this company?” They're picking up on clues about your competence, level of excitement, and conviction in what you’re saying, in addition to the actual content of your answer.

• Answering questions from prospective customers: Your prospect might ask one thing, but you want to address their underlying QBQ too. As a buyer, I might not be able to articulate what's gnawing at me. I've noticed the best salespeople answer my tactical surface question and go deeper to get at the root of the issue.

• Doing customer interviews: Customers might believe they need help with a specific solution instead of articulating their problem. As the product builder, it’s your job to dig deeper and tease out the QBQ.

https://x.com/thinking_slow/status/1704873862784065931

For all these scenarios, there’s an element of finesse involved because you’re listening to what’s said—while intuiting, asserting, and addressing what’s not said. In other words, you’ll need to read between the lines.

Part II: How to probe for more information

Acknowledge, then ask for more info

Your question-asker might not know how to articulate what they want. Take the time to figure it out together. Here are a few scripts to get you started:

• [Answers the question in 1-2 sentences] Great question. What makes you ask?

• Great question. If you could share a bit of context on what's top of mind for you, it'll help me figure out what to share that’s most relevant for you.

I phrased the above intentionally:

• Asking “why” (i.e. “why do you ask?”) is more concise, but I avoid it because some sales research shows that asking why can come across as aggressive and doesn’t generate the most useful responses. This is even more true in a remote environment because you don’t have facial expressions and tone of voice to signal warmth. On the other hand, saying what was shown to lead to better responses. For example, Why did you choose our software? vs What made you choose our software? Based on my personal experience, this tracks, so I err on phrasing with what if possible.

• I say “great question” in each response because I want to show a spirit of positivity and openness, especially if I’m not going to answer their question right away. Not answering their question right away is subverting expectations, so you need to counterbalance this by being extra positive in acknowledging their question. This creates goodwill, so they’ll feel comfortable and willing to share their QBQ.

Frame why it benefits them

Let’s say you’re speaking with a cross-functional leader you don’t work with often. You’re not familiar with what they care about, but you can guess based on their function: Product leaders, design leaders, CMOs, CFOs, and sales leaders view the world through different lenses and KPIs.

Consider what their concerns might be, then, frame your ask around why it benefits them to share context with you.

You could say:

"Hey, I'm presenting about X at Thursday’s all-hands meeting. I want to make sure to cover what's most relevant and top of mind for you. Here are a few high level ideas on what I think you'd want to know, but let me know what's missing and if there’s anything else you’d want me to include."

The script above did two things:

• You gave them ideas to build on. If you only ask what they want to know, you put the burden on them to think from scratch. It’s harder for people to think from a blank page than to push back on what’s in front of them. By sharing your thoughts, you increase the chances that you’ll get a useful answer.

• You show you’re doing your part. By sharing what you were planning to talk about without their input, you signal that you are actively thinking. You’re not only waiting for them to tell you what to do.

Part III: If you’re asking the question, share the QBQ

You might say, “Why can’t people just ask better questions?” You can only control your own behavior, and if you want to succeed, you’ll need to embrace pulling the right information out of people. If you’re the one asking a question, this is your chance to ask better questions.

Non-ideal question:

“Hey, are we still on track to launch our product announcement on x date?”

Good question:

“Hey, are we still on track to launch our product announcement on x date? I wanted to check in because last week, we added the Product Hunt campaign as a tactic, and you said there were more to-do’s for it than you originally thought. I want to avoid scope creep—we can do a pared down version of Product Hunt, or scrap it altogether if it puts other launch items at risk. There are a lot of moving parts, so I want to make sure you’re not being stretched too thin.”

This was a real question I asked my direct report when planning a high-profile launch at Maven. The first question isn’t bad, but if I had only asked that, I wouldn’t have been surprised if I got a short answer. I knew I wanted a more thorough answer, so I added context on why I was asking and what my QBQ was.

From there, my direct report shared the following, which was exactly what I was looking for:

• “Upon taking another look, the moving parts are more manageable than I thought.”

• “Here’s the launch calendar and upcoming milestones.”

• “What’s been harder than expected so far is…”

• “I’m feeling confident about the launch because…”

• “The part that might be a risk is…”

I've used the QBQ framework when answering questions from internal stakeholders (my cofounders, direct reports, team, investors) and external stakeholders (customers, partners, job candidates, journalists).

No question is wasted with a mediocre reply because I'm considering my audience’s concerns and answering strategically. It's win win. Considering the QBQ takes a few extra seconds, but it's worth it—and over time, it becomes instinctive.

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In summary:

1. Don't blindly engage in never-ending back-and-forth. Your question-asker might not know why they feel skeptical, so you're trying to hit a moving target.

2. Identify what their true concern might be. What might feel risky for them? What would make them confident that you've got this?

3. If you don't know the person, form a hypothesis about what they would find valuable. Use proxies like their function/role.

4. Probe for more information that will help you help them: "Great question. If you could share a bit of context on what's top of mind for you, it'll help me figure out what to share that’s most relevant for you."

5. Reward their inquiry with a positive attitude. Use this as an opportunity to build trust, educate them, and give visibility into the rigor of your thought process.

I’d love to get your help growing our community of thoughtful, rigorous operators. If you found this valuable, consider subscribing if you haven’t already, or take a moment to refer a friend. When you refer friends, you’ll unlock referral rewards—like my best book recommendations and recent spiky points of view. Use the link below because it’s your personal referral link.

Thanks for being here,
Wes Kao

PS See you next Wednesday at 8am ET.