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This ONE - How trustworthy are you?

The role of fear, our dance with AI, and holding a trusted space

This ONE by Yolanda Yu

This ONE idea and its manifestations in life and career

Happy This ONE Friday!

But while writing this newsletter, I am not feeling happy. And I think that is okay. My daughter’s close friend, also a 5-year-old girl, lost her mother last night. Though unfamiliar with her mother, I have met the girl many times. In the past years, she had grown from a timid toddler to a sweet child. It pains me to think that she may not have realized how permanent this loss is to be, and how much space this loss is to occupy in her young life.

But I try to remind myself, that the world dislikes void. Love will flood into that space. (I, and a few other parents in the community, seriously pledge to love her as much as possible, with her family’s permission.) Courage will. Friendship will. Strengths will. Most importantly, time will. That is how we eventually outgrow our loss and are grounded in the life story we grow. ❤️

Well, let me get back to this issue. Today it’s about:

  • What trust means in the AI era

  • How to be more trustworthy

  • Building a trusted organization culture

This ONE Idea

“To create trust, somone needs to pay it forward.”

I. Why Trust-building is important in the AI era

Prof Ethan Molick from Wharton just published a new book on AI. At his recent book talk, he mentioned, “We are not very good at dealing with exponential change - either too early or too late. Don't be too late.”

And right now we are in the midst of an exponential change. The fear is keeping people away from learning about AI, and at the risk of “being too late.”

For now, AI works best with human help, and you want to be that helpful human. As AI gets more capable and requires less human help – you still want to be that human. So the second principle is to learn to be the human in the loop.

Co-Intelligence: living and working with AI by Ethan Molick

His book and substack to follow.

Coincidentally, in my webinar with Kevin Pereira, MD, at Blu Artificial Intelligence, he also spoke of how fear is very present. He said perhaps it has to do with the Sci-Fi movies and experts in the room warning us of an apocalypse. However, he thinks that confusion and lack of understanding play a bigger role.

My takeaway from the two of them is:

1. Learn how much we can trust AI on each particular matter

We need to keep learning and testing out the “jagged frontier” of AI.

AI famously hallucinates. It prioritizes making us happy by producing “an answer,” over producing “the right answer.” But it has limitations. It may seem to know many things, and then it surprises you by knowing so little about something. And this is called the “Jagged Frontier.”

Through engaging with AI, we get to learn about its competence and incompetence. This learning is to decide how much we can trust AI on a particular matter more wisely. Without sufficient knowledge, we risk trusting AI too much or too little (with fear).

2. Savor our strengths in empathy and trust-building

Empathy and trust are difficult for AI to learn. Let’s see what the AI confessed:

Empathy involves understanding and sharing the feelings of others, which requires an intrinsic emotional capacity and personal experience—elements that AI lacks. AI operates through algorithms and data patterns, which can simulate responses based on programmed scripts or learned behavior from vast data inputs, but it does not experience emotions itself.

…establishing a deeper sense of trust that involves emotional assurance and ethical judgment is beyond current AI capabilities. Trust also involves nuances such as intentions and sincerity, which AI cannot authentically possess or express because it does not have personal motives or consciousness.

ChatGPT 4

In summary, we can feel not only ourselves but also other humans. This is a trademark of sentient beings and social animals. But AI doesn’t experience the world the same way as we do.

Trust is a complex thing between two humans or two systems (organizations, family units, ethnicities, etc). It goes beyond the psychological domain and can activate our chemistry and physical responses. Trust is also quite like a living being. It can be nurtured, damaged, used, or even transferred.

I know what being trusted is like. When I am trusted, I feel safe. A sense of warmth spreads on my back and in my chest. I am connected with a courageous and curious self. Trust has the potential to switch on our turban mode.

When was the last time you felt trusted and what was it like?

But then trust is also expensive. The potential misusing and abusing our trust is always a big downside and leads to terrible consequences. So we get careful, calculative, or even stingy about trusting. And when we do that, the opportunity cost of missing the upside of trust becomes prominent.

Introducing “Third Entity”

Unconsciously, we focus our decisions on the person. Is this someone I can trust?

A different approach is to think of trust as a relationship and an evolving dynamic. It is what we call the “third entity” in systemic theories. When we think this way, we don’t have to make a “yes/no” decision about trust. But instead, we can make micro decisions.

Trust is earned not through heroic deeds, or even highly visible actions, but through paying attention, listening, and gestures of genuine care and connection.

Brene Brown

II. Building a trust culture

The most common challenge for executives is activating their people’s potential. How to make people take more ownership, become more proactive in thinking, and challenge me or the decision when necessary? How can I make them put forward their best intelligence and passion to solve the big problems our organization tries to solve?

And I hear a lot that leaders are reluctant to give their trust first. They demand others to “prove you are trustworthy” before they hand out their trust. Such demand creates enormous pressure to prove oneself. Under such pressure, employees don’t feel safe enough to take ownership. Taking ownership is a risky act where we may be punished for being wrong or making an irreversible mistake.

Therefore, in this request, employees prove themselves first, is that they need to trust the leader first before the leader trusts them.

And that is a snobbish request. From which place of privilege can we ask other people to trust us first? At the same time, what have we done to win other people’s trust?

III. Winning the trust of suspicious bosses

There is a phenomenon that often perplexes employees. For every "scary" senior executive, some people always manage to get into their inner circle and ply with the dragon’s whiskers. They rub elbows with the leader, walk into his/her office without making appointments, and don’t ask for permission. They challenge the leader provocatively and emerge unscathed, or even rewarded.

People tend to attribute this to favoritism. Regardless of the reason, they have won the trust of these leaders. How did they manage to win the trust of a leader with high standards and expectations, and who can retract support at any moment in an unpredictable way?

They often share some common qualities: daring, direct, and self-assured. These individuals create a sense of safety not provided by the leader. They have their own trusted space. With this greater sense of trust, they choose to "pay forward". As a result, they receive it.

Isn’t that very risky? Indeed, it is. But that’s exactly what trust does. We become more vulnerable in reality, which makes us feel safer.

An interesting paradox arises where high-trust relationships create a subjective sense of security while making individuals objectively vulnerable.

(Trust paradox)

But then, it is not only the boss’s responsibility. We also have a role to play even in a fragile trusted space. That’s where we can take agency and reshape the relationship with leadership. (Yes if you think about the definition of “leader”, it’s simply someone who leads the way.)

Question For You

How trusted do you feel? And what can you do to grow trust in your life?



I found myself reaching out to people I trust when I put together the “Futureproof Your Career series.” The chances are, the trust is mutual. They are not necessarily “friends” who I interact with frequently. Some I have not spoken with for years. They are my classmates, ex-colleagues, clients, or referrals from someone I trust.

By running this series, I am creating an opportunity to further grow our trust.

Trust is gold. It’s hard to build. It can be misplaced or easily lost. And it stands the test of time.

Until next week,

Yolanda Yu
Coach and lifelong learner

Upcoming Webinar next Tuesday

Futureproof Your Career 2: with Daniel Pieper, ex-Hoolah CIO & Co-founder

Daniel built Hoolah and successfully exited. What is next?

Watch 👇🏻

Key points from the talk

  • Is Your Career Agile Enough for AI?

  • Opportunities and chilling realities in our job security

  • The right method of learning about AI

  • Our top strengths vs. AI


Or Listen to my podcast 👇🏻

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Every Friday, I share ONE idea and its manifestations and 1 question for you to ponder. Other ingredients you can expect will be book extracts, quotes, metaphors, tools, resources, and mini-exercises to keep growing your self-awareness.