Solving the Case: The Power of Asking the Right Questions

“There is nothing more deceptive than an obvious fact.”
― Arthur Conan Doyle, The Boscombe Valley Mystery

Sir Arthur Conan Doyle, through the infamous character of Sherlock Holmes, taught me something important at an early age.

That the obvious answers are rarely the most accurate. And that it’s worth examining things a little closer before even attempting to propose a solution.

These lessons have followed me into my career as a brand strategist and a facilitator.

One of the greatest misconceptions in communication is that the person doing most of the talking is in control of the conversation. But have you ever tried carrying a whole conversation by only asking genuinely curious questions?

Pose those intentional, genuinely curious questions and you’ve truly got a hold of the steering wheel.

You’ll become the trusted guide through the tangled rainforest of human interactions and you’ll often find that the more adept you get at this role the smarter you are perceived to be.

It’s ridiculously simple to affect that perception, but yet it can take hundreds of hours to truly perfect.

However, it’s not as simple as JUST asking questions, you need to be asking the right questions and in the right order to help funnel your conversation partner in a constructive direction.

Let’s see if we can break this down.

1. Cultivate a healthy and genuine sense of curiosity

Have you ever seen someone’s eyes glaze over as you’re providing an answer to a question they just asked?

What is happening?

It seems logical that question = interest in the answer you are more than happy to provide. But, unfortunately, that is not always the case, especially if you were too quick to provide one.

Small talk is chock full of these kinds of interactions: benign questions, canned answers and “here’s my business card.”

The problem is that curiosity takes energy and engaging in the moment and most of us are too stressed, busy, nervous or disinterested to bother.

But just like anything, the more you exercise curiosity the easier it becomes.

Similar to when you first get a gym membership; at first you feel awkward but with consistency comes proficiency.

Gym rats get depressed when they miss a day with the dumbells, and you’ll feel weird if you fail to truly engage your curiosity in a conversation.

2. Listen to understand, NOT to respond

Employ “active listening”, this isn’t a race, stop formulating a response in your mind while the other person is speaking.

When you do this the voice in your head gets louder and your mind is no longer engaging with what the other person is saying. Instead, it’s listening for them to pause for breath so you can jump in with your clever input.

It’s also not enough to just to hear their words and even repeat them back, that means you heard, sure, but did you understand?

Did you understand what they were trying to communicate enough to be able to follow up with an insightful, clarifying or curious question? Consider that your measuring stick.

3. Ask the right questions

How wonderfully vague.

“What are the right questions?! Give me a formula, a recipe, a cheat code, something!”

I’m sorry, there’s no “one size fits all” formula.

Of course, there ARE formulas for communication, but no single one will be applicable in every situation. So, what I am going to share with you are strategies that can be applied in almost any conversation vs. a single use cheat code.

With that being said, the right questions are less about specifics and more about context, and that’s why the previous two points are so important.

If you’re really listening to someone, and genuinely curious about their answers, the right questions will be obvious.

The next step is going to dive into this a little deeper into a specific strategy and two very different ways to use it.

4. Build a funnel

There is a questioning technique referred to as funneling. The simplest way to describe the method is starting with closed questions and funneling towards open-ended questions, or reverse it and funnel towards more closed and specific questions.

To make sure we’re on the same page here:

Closed questions have a single answer, i.e. yes, no, blue.

Open-ended questions invite expanded answers, stories, and context, i.e. what did you do this summer?

Closed questions are not very good conversation starters, but open-ended questions usually require more trust to answer.

On the other hand, closed questions are great for acquiring specific information, whereas open-ended questions are great for acquiring context and sniffing out the bigger picture.

Let’s examine two different examples, which way you would funnel and why.

Situation A — Meeting someone new

Funnel from general and closed (small talk style) questions to more and more open-ended questions using curiosity and active listening to encourage them to tell you more.

When I meet someone new at the co-working office, I will begin with a comfortable “Hello, I don’t think we’ve met…” followed by some predictable and closed questions, “How long have you been here?” then a slightly more open question, “What is it that you do?”.

This is usually the point where I can ask more open and curious questions as they describe their occupation, I can ask “What got you into that?”
“Oh, so you moved here recently then? Where from?”
“What brought you here?”

Often, people are more than delighted to talk about themselves to a genuinely interested party. And in the rare case where someone isn’t so keen, leave them alone, they’re an undercover agent and you’re blowing their stakeout.

Situation B — Conversation over lunch

These are my favorite conversations.

I often begin with what I know about what’s been happening recently or what they told me they were working on last time we spoke and then ask, “So, how’s that been going?”

The conversation starts right off the ground with them feeling seen, heard and listened to because I showed them I’ve been paying attention.

I love to follow up those very open and exploratory questions with something just slightly more closed, “So, what’s your goal with that?” or “When are you aiming to have that done by?” (always with a friendly smile).

Because they’re feeling comfortable with me they will usually admit where things are hazy or undecided and I’ll ask, “Why do you feel uncertain about that?”
“What do you think will help you feel confident about that decision?”

This is approximately the point where I might transition to closed questions, helping them provide more and more specific answers. And if they haven’t answered their own dilemma themselves by now, I will ask if I can offer a thought.

I will have these conversations over lunch, in a strategic meeting, in a coaching or consulting session. The frame can be different but the funnel remains the same.

Start these conversations with the open questions, slowly funneling and guiding to more closed questions that require them to give specific answers. This technique is masterful for helping someone reach clarity and identify goals, tactics and action steps.

With practice, you can become so good at this that someone is completely unaware that you have intentionally guided them to their aha moment, let alone how you did it. They will be amazed, grateful and may even ask you why you’re not a business coach.

This technique works best when you are able to inspire trust in the other party. How you phrase your questions, genuine smiles, comfortable eye contact and empathy go a long way in making this approach successful.

Whether you're funneling from closed to open or vice versa, if the other person feels even the slightest bit interrogated, both will fail in a mushroom cloud of disappointment.

5. Listen for what they’re sort of saying

Here is where the lesson from Sir Arthur directly applies.

As humans, subject to social expectations, personal baggage, denial, and distractions we often ask questions or provide answers that are shallow or barely scratch the surface.

And sometimes we simply don’t know what we should ask to accomplish our objectives, period.

It is safest to assume that someone is not saying everything, either consciously or subconsciously. Or if they are asking you for advice, returning their question with a few questions of your own can inject a dose of clarity and help you give more targeted and beneficial solutions.

We can all practice asking better questions and therefore receive better answers, but in the meantime, it doesn’t take much to examine and sniff out if someone is asking you a well thought out question.

Over time, you’ll begin to spot murky questions from up to a few miles away. The slight hesitations, the re-directs, the skating and other avoidance tactics will invite you to dig in. Add just a dash of empathy and discover what is really motivating them beneath the surface.

To rephrase what Sir Arthur so deftly explained, there is nothing more deceptive than the obvious answer.