The difference between questionable and question-able

I’m a career Creative. I love it. My first gig out of college was a copywriting job, but I’ve also dabbled in design. The combo has given me a holistic POV. And for most of my career, I’ve led teams that were charged with solving business problems in some form of marketing communications.

Each one is a fun puzzle to crack. Some can leverage past work, some require a bespoke solution. But regardless, the critical thinking that leads to success can be applied every time.

From omnichannel, audienced ad campaigns to sales enablement decks for reps in the field, literally every project I’ve ever worked on has started with Discovery.

Whether it’s a well-crafted brief from the Account team, a thoughtful convo with the client, or both – to loosely paraphrase Lao Tzu – a journey of a thousand miles begins with the Discovery step.

What’s your single most powerful tool in Discovery?

Questions.

What's a topic that can be more polarizing than cilantro?

Questions.

The critical thinking that leads to success can be applied to virtually any type of creative project. And questions are the primary tool in the critical thinking toolkit.

Asking questions takes guts.

To be effective, the question-asker must bring curiosity and openness paired with laser-focused intention. It requires confidence to put yourself out there in a world where lots of folks attend meetings, but very few engage.

But when done well, the process itself is a joy for folks:

• “He took the time upfront to really understand the business need.”
• “Out of everyone I talked to, his questions made me stop and think the most.”
• “He ‘gets it’ and asks the kind of questions that give him the understanding necessary to best speak to his audience.”
• “After asking the right questions and listening carefully, he developed a professional brand identity for my business, and captured the essence of my business and industry.”
• “His questions and direction consistently make the work better.”

You establish yourself from square one as a partner. It sets their mind at ease. It builds immediate camaraderie. Why? Because it shows you care, and you have skin in the game when it comes to their success.

It requires confidence to put yourself out there in a world where lots of folks attend meetings, but very few engage.

“There’s no such thing as a dumb question.”

Oh yes, there is. There’s a whole category for it called, “stuff you could have easily answered for yourself.”

If you peruse any DIY forum, you’ll quickly see a divide between “that’s a really good question, here’s some advice” vs. “there’s a thing called Google – this has been asked a thousand times.” The latter tends to escalate quickly.

One example in Creative is asking the client something fundamental about their business that’s clearly conveyed on their website. Why is that a bad question? Because it shows you didn’t come prepared. You’ve already sent the message that they will have to work harder because you probably won’t.

Questions only work if they're really good questions. And every question should be asked in the spirit of informing a uniquely effective solution to a real and clearly defined problem.

Questions only work if they're really good questions.

What’s the antidote? Prep.

Do some thoughtful pre-work before you get valuable face time.

For example:

1. Connect with the rest of your team to learn what may have already been discussed (new-biz/account folks, etc.). Ask for meeting notes. Read them, make your own notes, capture initial questions (and see how many you can answer BEFORE the convo). The last thing you want is for the client to feel like they're in a CS loop, re-answering the same questions each time they're connected to someone new.
2. Do your own research to get a sense of who the client is, what they stand for, and what they’re trying to accomplish. What is your impression of their website? Is it clear what they do, and why it matters? Are they in the news? Is there a Wikipedia page about them?
3. Start looking for opportunities, gaps, patterns – anything that can inform your initial (pending input) POV.

Every meeting is an expensive room. Show you get that, and you’re going to facilitate getting max value out of every precious minute.

The last thing you want is for the client to feel like they're in a CS loop, re-answering the same questions each time they're connected to someone new.

You should already have a unique POV going into your first convo.

Then, the conversation becomes a quick validation of your POV and/or it becomes a fruitful launching point for getting to meaningful insights that will serve as the bedrock of that project’s (and client’s) success.

Bring a smart combo of being prepared + flexible. This is a two-way exchange. Foster that. Ride the convo where it goes. Be prepared to leverage happy accidents or drill down on something interesting. See where the conversation leads you.

You want your Discovery meeting time to be a thoughtful exchange that hits the ground running and immediately demonstrates the value you offer.

Bring a smart combo of being prepared + flexible. This is a two-way exchange. Foster that. Ride the convo where it goes.

When used effectively, questions drive amazing outcomes.

But here’s the rub…

Some people hate questions.

We’ve created a culture of urgency. People feel rushed to action. The only problem is that sometimes the action is only an illusion of progress.

Doing something really fast doesn't necessarily mean it accomplished anything. For example, putting a bunch of meetings on the calendar without first getting clear on the role meetings will play – or if they're even advisable for the task at hand. The irony is, that kind of mindset often gets in the way of actual, intentional progress.

Suffice it to say that not everyone you collaborate with is going to be excited to think about things they don’t deem necessary for day-to-day existence. Questions force us to pause and think on a deeper level than hurriedly checking items off our daily to-do list.

I get that. Also, too bad. This is about ensuring that the project is successful. Questions are a tool for understanding. So get engaged – or, at a minimum, don't stand in the way of the folks who are willing to put themselves out there and champion success.

Determine your true collaborators.

I think the trick is quickly figuring out who’s who: your curious fellow explorers-of-greatness, and your unengaged list-checkers. Embrace the former, and don’t waste your time on the latter. Here's a quick and easy litmus test:

1. Ask a thought-provoking question during a meeting.
2. Look at their faces.

Your intuition will likely be spot on. Roll with it.

Not everyone gets it – and that’s OK.

Be prepared for that. As much as you can, anyway.

I was once on a Zoom meeting with new clients, using a semi-Socratic series of prompts to help clarify the clients’ needs. At a point in the convo, one of the clients blurted out something brilliant. It was quick and complex, but I could tell there was gold there. So I asked her to repeat it.

That's when the otherwise-silent Account person immediately chimed in with, “We’re recording this call, you can go back and watch it again later.”

I about fell out of my chair.

What could have become a really productive convo ended up being fairly awkward. In the end, we finished the meeting and I guess everything was fine. But I'll always wonder where that convo might have gone had the first insight-spark not been immediately extinguished.

Some people hate questions. I get that. Also, too bad. This is about ensuring that the project is successful.

Want to ask really great questions?

Here are three influences I keep front-of-mind in virtually every engagement:

1. People who look spontaneously brilliant are really just people who have prepared to be ready in that moment. It’s the whole premise of The Accidental Creative by Todd Henry.
2. Stay curious, flexible and open to little gifts as they present themselves. Rick Rubin talks about this in The Creative Act: A Way of Being.
3. Continually re-evaluate your paradigms about people. There’s actually training for it. An organization that does an amazing job is UNLRN.

What's your favorite go-to question?

I find myself asking "What does success look like for X?" a lot. Setting your North Star from jump is always advisable. I also love "What's the dream?" for convos where it makes sense.

What about you? What are some of your favorite questions that help drive greatness?

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Jeff Thomas is a professional Creative in Cincinnati, OH. He's been a writer ever since he started writing.