Why 'Learn-it-alls' Beat 'Know-it-alls'

Welcome to Love Mondays More! This is where the ideas from Love Mondays , (my weekly email newsletter), get a bit more room to stretch—diving into deeper stories, strategies, and tools to help you lead with intention and impact.

If you’re enjoying Love Mondays More, you won’t want to miss Love Mondays. It’s your Monday morning jumpstart — packed with personal insights, exclusive content, and a mini activation challenge to push you into action each week. Not to mention private community events!

Think of it as the little kick in the pants we all need sometimes. Because real change starts on a Monday. Join me and let’s make your Mondays (and your week) count.

In my work, I have the privilege of engaging with some of the most brilliant minds across industries, and every conversation leaves me with the same humbling realisation: the more I know, the more I see how much I don’t.?

And honestly, I love it. I love being able to meet masters of their craft, deep experts in technical subject matters and leaders at the top of their game and learn from their wealth of knowledge and expertise. I see one of the great privileges (and challenges) of my role in this regard in serving as a bridge between my guests’ worlds and the leadership contexts of my audience.?

Not knowing is a humbling, sometimes uncomfortable experience. But in a world where information changes faster than your news feed refreshes, professing to have all the answers or clinging to certainty are part of a playbook that produces a poor outcome. What was the right course of action or an innovative idea yesterday might be obsolete tomorrow.?

The real superpower isn't knowing all the answers; it's knowing how to learn, unlearn, and relearn – on repeat. And equally, how to build a culture amongst your team where those ideas are embraced by most, not just a handful of outliers.?

What we’re talking about is practising intellectual humility : the recognition that you don't have all the answers (here’s the world’s worst kept secret: no one does!); the openness to new evidence, information and ideas, even if/when they challenge your pre-existing views; and the willingness to approach every conversation as an opportunity to learn something new.

Leaders who embrace intellectual humility don't just build better teams – they build learning ecosystems. They create spaces where ideas flow freely, where saying "I don't know" is the start of a process of enquiry or discovery, not a confession of weakness or a ‘CLM’ (career-limiting move). Their teams innovate faster, adapt smarter, and solve problems more creatively.

Why? Because when you're not busy being the smartest person in the room, you create space for everyone's brilliance to shine.?

Why Saying “I Don’t Know” is the Boldest Move You Can Make

What sets exceptional leaders apart isn’t certainty—it’s adaptability. And adaptability begins with admitting the gaps in your knowledge—those “I don’t know” zones that are ripe for exploration.

That’s why it’s crucial to seek out intellectually humbling situations—the kind that push you past your comfort zone and force you to stretch your thinking. Because if you’re not willing to get uncomfortable, you’re probably not growing.

“Don’t be a know-it-all, be a learn-it-all.” - Satya Nadella, CEO of Microsoft.

How to Put Yourself in Intellectually Humbling Situations

The good news is that intellectual humility isn't some innate trait you're either born with or without. It's a skill, a muscle you can strengthen with consistent practice. Here's your training regimen:

1. Build a brain trust (and actually listen to them)

Think of your personal brain trust like a crew of experts and challengers who make you smarter by pushing your thinking. These people should be those who know more than you in specific areas, whether they're industry veterans, colleagues with different specialties, or even team members with fresh perspectives (from a different generation perhaps?).

But you have to actually listen to them. Too often we invite smart people into the room but don’t make space for them to truly be heard. Let them push back—and don’t just tolerate it, encourage it.

I had a great conversation with a mentee of mine last week, who’s ten years my junior, about psychological safety in the workplace and I was really challenged by some of the Gen Z viewpoints of the topic. I have a richer, more nuanced view on this idea-in-action in multi-generational teams now because of that conversation.

Seek it out, embrace the heat and discomfort.?

2. Ask better questions (even if it feels awkward)

Curiosity is your superpower—so use it boldly. Ask open-ended questions, even if doing so makes you feel vulnerable. The goal isn’t to show off what you know, but to uncover what you don’t. Some of the most inspiring leaders I’ve met are masters of the thoughtful question. They’re not afraid to probe deeper or explore new perspectives. Here are a few of my favourites:

• "What are the potential downsides of this approach?"
• "How would someone with a different perspective see this?"
• "What assumptions are we making that might not be true?"

Some of my best business insights have come from questions I was almost too embarrassed to ask. Ask them anyway.?

Another way you can take your first step into this is to use AI to challenge you, as a precursor to inviting more challenge in the room. Upload your idea or proposal and ask? “What are three limitations or potential blind spots in what I’ve presented?”, “What would it take for me to be wrong about the conclusions or assumptions that have underpinned my argument?” etc. This is a fast and easy way to start challenging yourself.

3. Turn your team into truth-tellers

Create a team culture where disagreement is welcome. Leaders who ask, “What would someone who disagrees with me say?” foster better conversations and avoid groupthink. But it’s not enough to just invite challenges; without structure, those objections often never surface.

This is where the 12th man concept comes in. In sports, the 12th man’s job is to bring outside perspective and push the team further. In your meetings, make it someone’s responsibility to challenge assumptions and ask the tough questions. When challenging ideas is a job—not just a suggestion—you unlock insights and innovations you might never have seen coming.

So, show up, ask the weird questions, get things wrong, laugh about it, learn from it, and try again. Because at the end of the day, the future belongs to learn-it-alls.

What’s one thing you can do this week to get more comfortable with “I don’t know”?