Why Knowing Everything Isn’t Everything

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Throughout my career, I’ve encountered plenty of seasoned executives who radiated confidence, swept in with answers, and all but demanded we trust them because they’ve “done this for 20+ years.” 

These executives are so used to getting it “right” that they’re not used to ever being wrong.

And the most dangerous thing for an executive is to think they have it all figured out.

Why “Not Knowing” Might Be an Executive's Greatest Asset

Expertise is a double-edged sword: While it provides a foundation for intuition and insights, it can also create blind spots. When executives rely too heavily on their expertise and refuse to seek fresh perspectives, they stifle their own growth and that of their teams.

Meanwhile, I’ve noticed that newer execs carry far fewer preconceived notions and aren’t held back by how things “should work.” They are more likely to learn by ideating, testing, and iterating. They try lots of things and see what sticks.

They’re also not afraid to ask questions and enlist the help of others—which is a hugely overlooked area for leaders. As highlighted in Jeff Wetzler’s book, Ask, the answers to our biggest problems are often sitting in the heads of our teams, customers, or investors. Too often these folks aren’t sharing their crucial insights with us because we’re not trying to learn from them. 

Changing Your Story: Fixing a Fixed Mindset

Kids are constantly forced into learning mode, and as mine have been taking on new skills, I have been learning alongside them—bicycling, piano, and Chinese, for starters. 

OK, I still bike mainly in empty parking lots, piano is getting super tricky with two hands, and my Chinese is at a 2-year-old’s level, but I’m counting it! It is humbling—and a reminder of just how challenging it can be. 

Bicycling as a kid, I never quite got past training wheels. I was too afraid of falling. Now, I find myself shifting my internal narrative: I’m not someone who could not learn, I was someone who hadn’t tried. And our family mantra now is, “Just try it” (a la Nike) when endeavoring a new task. 

With my own clients, the importance of providing psychological safety to be willing to explore is front and center. I’ve even cribbed a framework from my kid’s elementary school that universally works:

The “Good / Better / Best” Approach

Imagine learning to ride a bike. Starting with training wheels is the "good" phase—you're safe and gaining balance. Removing the training wheels is the "better" phase—it's challenging but you're improving. Mastering riding without falling is the "best" phase. The key is to celebrate each phase and to recognize that improvement is a journey, not a destination. 

Don’t start out the first try as your best try, but a good try—one that intentionally allows room for errors and first-attempt snafus. With my perfectionist kid, we start with “not so good” attempts before our good attempts, where we intentionally try to do it terribly!  

Embracing a Growth Mindset: Committing to Constant Learning

Learning to learn is the most important skill we as humans need to survive, but it’s one we often forget we still need as we rise up the ranks. Learning is the fundamental building block—at every level—to handle all the challenges being thrown our way: pandemic? AI? More unprecedented times? It never ends, and learning can’t either.

So, how do we as executives develop the muscle and mindset of continuous learning?

Try these tactics:

• Mindset matters: To truly have a beginner mindset, throw out your assumptions and come with an open mindset. Leverage the power of a growth mindset (“I haven’t learned it … yet”), and prepare yourself for things that scare you through self compassion and positive self-talk.

• Mix it up: Try a variety of approaches to figure out how (and where) you best learn. In addition to new workplace skills, also consider less directly applicable skills too. Ethena CEO Roxanne Petraeus writes about learning to fall with her kid. And equine leadership programs are one example of bridging outdoor lessons with workplace learnings.

• Give it space: . Spaced repetition, with time for brain breaks, helps concepts stick.

• Break it down: We aren’t wired to receive too much information at once. Breaking things down into small, digestible, bite-sized chunks ensures we actually retain the content better in the longer-term.

• Focus on how, not what: The journey is more important than the destination, right? Instead of focusing on the achievement or outcome, prioritize how you’ll get there. Is it building muscles though repetition, ever increasingly difficult challenges, or something else? Famous designer Vera Wang reinforces this: “Success isn’t about the end result, it’s about what you learn along the way. 

• Reflect: After you’ve learned, be intentional to consider how this new information influences your existing thoughts, beliefs, and approaches. 

You Can Learn Anything (30 sec)

(Here’s a 30-second clip from Khan Academy, back when I was chief of staff, that still inspires me to this day. Doesn’t it make you feel better about not knowing everything?!)

More info

Want to learn more about learning? Add these to your TBR pile:

• Mindset by Carol Dweck

• The ASK strategy by Jeff Wetzler

• Teaching Smart People How to Learn by Chris Argyris

Ready to unlock your leadership potential and accelerate your learning? Schedule a free discovery session today.

Keep reading, keep leading,

Jess

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For more, follow me on LinkedIn or check out my website.

I’m Jess Yuen, a trusted advisor and executive coach for fast-changing companies. Interested in finding out how I can support you in your journey? Contact me here to find out more.  

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