The case against assertiveness and the beauty of “I don’t know”

“One of the painful things about our time is that those who feel certainty are stupid, and those with any imagination and understanding are filled with doubt and indecision.” — Bertrand Russell

I still remember the day a former boss told me that my lack of assertiveness was a major flaw. According to him, as the leader of my team, I needed to speak louder and radiate confidence. However, as an introvert, my inclination has always been to listen first and then make suggestions, rather than command with an iron fist.

I didn’t feel comfortable leading before, but now I am, as I’ve found a place that values my quiet leadership style. I’ve never been the loudest person in the room, but I do consider myself a very good listener. When you truly listen, you understand people better. You hear their objections, anxieties, and fears. You also hear solutions to problems. However, people tend to hold talkers in higher regard than listeners.

Don Draper, the epitome of assertiveness.

I’m sure you’ve been in meetings with characters like Don Draper — full of unshakable confidence. They wield authority, leaving no room for doubt. Their charm lies not in the strength of their arguments, but in the self-assurance they radiate. In many ways, they resemble politicians, defending their ideas without engaging in dialogue.

So, let me present a compelling case against the notion of assertiveness and reveal the beauty of uncertainty.

The tricky side of assertiveness

Assertiveness has been considered a vital characteristic of confidence, authority, and effectiveness. We’ve been told that having all the answers and projecting certainty is the golden ticket to success. But this fails to acknowledge the limitations and potential pitfalls of an overly assertive mindset.

While assertiveness itself is not inherently negative, it becomes problematic when taken to an extreme level. Take Thanos as a sample.

When we obsess over certainty, we build walls of closed-mindedness. We become less receptive to new information, limiting our personal growth. Imagine a world where we can’t see our own blind spots. It’s like walking around with blindfolds, pretending we’ve got it all figured out. Not exactly the recipe for progress.

By refusing to embrace the unknown, we severely limit our potential to gain new knowledge and insights.

In the rapidly evolving tech industry, change occurs at lightning speed. We need to stay open to fresh ideas. Yet, the traditional assertiveness script frowns upon admitting that we don’t know something. But guess what? By refusing to embrace the unknown, we severely limit our potential to gain new knowledge and insights.

So, what’s the solution? It’s time to hit the pause button, reassess our perspective on assertiveness, and invite a new cast of characters onto the stage: humility and curiosity.

Embracing humility and curiosity

Amélie’s curiosity drives her to explore the world around her and this leads her to discover hidden treasures in everyday life.

Intellectual humility sounds like a fancy term, but it’s basically the superpower of recognizing the limits of our knowledge. It’s acknowledging that we don’t have all the answers and being okay with it.

Curiosity, on his part, is a beacon of light, illuminating new paths and uncovering hidden treasures. By adopting a questioning mindset, we challenge our assumptions, seek alternative perspectives, and dive into the unknown.

Now, let’s be clear. I’m not saying we should completely ignore assertiveness. In high-pressure situations where quick decisions are essential, a resolute individual can often provide more assistance than someone who is hesitant. I’ve had the chance to work with some really impressive assertive people who any team would love to have

Assertiveness really shines in high-pressure activities like sports, medical emergencies, and firefighting, just to name a few.

My intention isn’t to outright dismiss assertiveness, but it’s time to invite humility and curiosity to the party. By taking this more nuanced approach — one that integrates intellectual humility and a sincere thirst for discovery — we create an environment where uncertainties are celebrated, ideas are exchanged, and new knowledge flourishes.

Think Again and The Scout Mindset

These two books are amazing, I cannot recommend them enough.

In the works of Adam Grant’s “Think Again” and Julia Galef’s “Scout Mindset,” we can find a common thread through the narrative: the transformative value of questioning our own beliefs and embracing a rational approach to uncertainty.

In “Think Again,” Adam Grant introduces us to a hierarchy of thinking styles, with The Scientist at the top and The Politician and the Cult Leader at the bottom. Imagine a world where we embody the spirit of the scientist — a champion of open-mindedness, perpetually seeking evidence and updating beliefs based on data.

Grant explains the value of embracing the scientist’s mindset for enhancing decision-making and fostering intellectual growth. Scientists thrive in uncertainty, admitting when they don’t have all the answers. On the other hand, politicians cling to pre-existing beliefs, wielding persuasion as their weapon of choice.

A hierarchy of rethinking styles by Adam Grant.

Now, let’s dive into the Scout Mindset. Picture yourself as a scout, venturing into the unknown with a burning desire for truth. Intellectual humility becomes your trusted companion, urging you to recognize the limits of your knowledge and question your own beliefs. A questioning mindset becomes your weapon of choice, a powerful tool to challenge assumptions, explore alternative perspectives, and discover new ideas.

In The Scout Mindset, Galef illustrates the contrast between an assertive mindset — represented by The Soldier — and a curious mindset — represented by The Scout — by comparing these two distinct approaches to reasoning.

⚔️ The Soldier Mindset

1. Reasoning is like defensive combat.
2. Decide what to believe by asking either “Can I believe this?” or “Must I believe this?” depending on your motives.
3. Finding out you’re wrong means suffering a defeat.
4. Seek out evidence to fortify and defend your beliefs.
5. Related concepts: Directionally motivated reasoning, rationalizing, denial, self-deception, wishful thinking

🕵️‍♀️ The Scout Mindset

1. Reasoning is like mapmaking.
2. Decide what to believe by asking, “Is this true?”
3. Finding out you’re wrong means revising your map.
4. Seek out evidence that will make your map more accurate.
5. Related concepts: Accuracy-motivated reasoning, truth-seeking, discovery, objectivity, intellectual honesty

The power of questioning and rationality ignites a cascade of personal growth, collaboration, and learning. We acknowledge the limits of our knowledge, learning from others and valuing the diverse perspectives they offer.

The beauty of “I don’t know”

While Jon Snow may be beloved by everyone, my greatest admiration goes to Sam Tarly. His scientific mindset and Scout Mindset have always captivated me.

Saying “I don’t know” is not a sign of weakness but a badge of intellectual humility. It’s a declaration that acknowledges the vast limits of our knowledge and opens the gates of curiosity and the thirst for understanding.

But let me tell you something even more exciting — admitting uncertainty is a mighty catalyst for personal and intellectual growth. It sets in motion a desire to seek out new information, to explore different perspectives, and to discover novel experiences.

Admitting uncertainty is a mighty catalyst for personal and intellectual growth.

Openly admitting what we don’t know creates an environment where collaboration flourishes. It nudges us to seek input from others, valuing the diverse perspectives they bring to the table. This openness fosters constructive dialogue — a playground of ideas and innovation.

So, the next time you find yourself in a room with a Don Draper-esque character, don’t be swayed by their confidence. Instead, think like a scientist — embrace the spirit of inquiry, follow the trail of evidence, and let your open mind be your guiding compass.