Your dangerous obsession with having answers

Hi friends,

I’m going to let you in on a little secret today.

I have built my entire career on not knowing things.

Seriously.

People look at the brands we’ve built at sydneysam.com, workspaceglobal.com and openspaceglobal.org and assume it happened because I give insightful speeches or have some master blueprint. But it’s actually the exact opposite. OPENSPACE became what it is because we created a community focused on asking incredibly deep, revealing, and sometimes uncomfortable questions.

It’s the same story with my executive coaching. Clients invest good money to leverage unique approach to solving problems. Some imagine there’s a master folder of plays and answers. I don’t have one. Instead, I focus on asking simple, piercing questions that force them to confront what they’ve been avoiding or haven’t been able to see.

Honestly, asking questions has helped me be a better husband. It took me a few years to realise that when my wife, Nana Aba, is talking about a stressful day, she doesn’t need me to put on a “fix-it” cape. Asking questions that show genuine curiosity and consideration for her perspective does wonders. Turns out, “How did that make you feel?” is infinitely more romantic than “Have you tried optimising your calendar?” (And it keeps me off the couch).

But nobody teaches us this.

We carry this heavy, invisible misconception that our value in our teams, businesses, and workplaces is tied to how many answers we have. We think if someone throws a problem at us, we have to instantly blurt out the solution to prove we deserve to be in the room.

But let’s be real for a second. We are living in 2026. Answers are the cheapest commodity on the planet.

We have Google. You have insanely powerful AI tools. If a machine can spit out a perfectly structured answer in three seconds, your value as a leader cannot just be “knowing things.”

When you rush to provide the answer, you actually close the door. You end the conversation. You signal to your team that the thinking is done and their job is just to execute.

But when you ask a great question? A lot changes.

Questions steer the ship in the right direction. They give your team permission to ponder, to inquire, and to build on top of each other’s ideas. They create space for healthy, respectful challenge. A good question doesn’t show weakness; it drives everyone toward a vastly better outcome because it forces the room to be clear, important, and inclusive.

Look at how Jesus led. He is literally the Son of God - if anyone actually had all the answers, it was him. Yet, the Gospels show him asking over 300 questions, while directly answering only a fraction of the ones thrown at him.

There is a beautiful verse in Proverbs 20:5 that sums this up perfectly:

“The purposes of a person’s heart are deep waters, but one who has insight draws them out.”

Your job as a leader isn’t to pour water into the well. It’s to draw the insight out of the people around you.

So, how do we actually do this? How do you step into your next meeting, review a team report, or sit with a client and generate better questions?

Keep it simple. Here is a 4-step framework to help you drop the “answer trap” and start leading with inquiry:

1. Kill the statement in disguise

Most people don’t ask questions; they make statements with a question mark tacked onto the end. “Don’t you think we should pivot to marketing option B?” That’s not a question - that’s your ego pushing a perspective. Drop the bias. Instead, ask: “What are the risks if we choose option A over option B?” Help everyone come to the outcome you think is best ... together.

1. Go one layer deeper

When someone hands you a report or a project update, don’t just nod and move on. Ask the follow-up question that makes them show their work. Try: “What was the biggest assumption we made when choosing this approach?” or “What surprised you most about these numbers?”

1. Ask to include

A great leader ensures that the quietest person in the room has a hand in the build. Before making a final decision, open the floor with an intentional check: “Who sees this differently?” or “What is the elephant in the room that we’re all avoiding right now?”

4. Pivot to action

Don’t let inquiry turn into an endless philosophy session. You still have a business to run. Once the room has pondered, anchor the conversation back to reality: “Given everything we’ve just discussed, what is the single most important next step?”

Write these down on a sticky note. Put them on your laptop.

Take a deep breath and put down the burden of needing to know everything. Let the tools find the data, but use your voice to find the direction.

Go into your workplace this week and try to talk 50% less, and ask 50% more. Watch how the energy in the room shifts when you stop trying to be smart and start trying to be curious.

We’re all in this together.

Stay awesome,

Sydney

P.S. I’d love to chat with you personally about how you can personally start asking better questions. Pop me an email at hello@sydneysam.com