On Giving Advice

I. The Eagerness to Help

Very often, I find myself in situations where people seek my advice. I must confess that earlier in life, I was far more eager to offer it. Looking back, I now believe much of that advice was misguided — not necessarily because it was wrong, but because I had not yet grasped the weight of influencing another person’s decisions.

I remember a young colleague, early in his career, who came to me uncertain about whether to leave a stable job and join a startup. I gave him a confident, detailed answer — essentially the choice I would have made, mapped onto his life. He followed my advice. The startup did not work out. Whether it was the right decision for him, I will never know. But I remember that conversation with some discomfort, because I had answered his question as if it were mine to answer.

That discomfort has been useful. It taught me that confidence in giving advice and wisdom in giving advice are not the same thing.

II. The Danger of Projection

Over time, I have come to see that advice can be quietly dangerous. When we counsel someone, we risk projecting our own fears, assumptions, and mental models onto them. What we mistake for wisdom may simply be personal bias dressed in the language of truth.

The daughter who wanted literature. I once knew a parent who had built a successful career in medicine. When his daughter showed a strong aptitude for mathematics, he steered her firmly toward the sciences — medicine specifically. She was talented enough to succeed, and for a while everyone assumed the story would end well. Years later, she confided that she had always wanted to study literature. She had the grades, the drive, the private notebooks full of essays no one had read. She had simply never been given permission to want what she wanted. Her father’s advice was not malicious. It was, in its own way, loving. But it was shaped entirely by his map of the world — a map she had not drawn and did not share.

This is the subtler risk: that our advice is autobiography. We speak from our own experiences, our own disappointments, our own definitions of a life well-lived. The person in front of us may be a different kind of person, in a different context, reaching for something we have never even imagined wanting.

Good advice requires intellectual humility — the recognition that what worked for us, or what we wished we had done, may be entirely the wrong medicine for someone else.

III. The Trap of Dependency

Even more troubling is that excessive advice can erode a person’s capacity to think for themselves. Instead of learning to find their own footing, they begin looking outward for answers — outsourcing their judgment, then their confidence, and eventually their sense of self-direction.

The protégé who couldn’t choose. I once worked with a student who was exceptionally bright — curious, hardworking, and full of potential. But she had spent years in an environment where she was always told what to do: which courses to take, which career to pursue, how to spend her summers. When she finally reached a point where she had to make a decision independently, she was paralyzed. Not because she lacked intelligence — she had plenty — but because no one had ever let her practise the act of choosing. The muscle had never been exercised. She would come to me with the smallest of decisions, waiting for me to sanction them. My role, I eventually realized, was not to make those decisions easier but to gradually withdraw from the process — to make her comfortable with the discomfort of deciding.

There is a version of mentorship that feels generous but is actually self-serving: the mentor who is always available, always prescriptive, always the one with the answer. It feels like care. It functions like control. And it leaves the person, in the end, less capable than when they arrived.

IV. Four Kinds of Mentors

What, then, qualifies as good advice?

Consider four kinds of mentors:

1. One who gives a person a fish.
2. One who teaches a person how to fish.
3. One who teaches a person how to learn, discover, and solve problems independently.
4. The meta-mentor — one who helps a person become the kind of individual described in (3): someone capable of continuously learning, adapting, and discovering things for themselves, and in turn capable of mentoring others the same way.

Most advice lives in category one. Some good teaching lives in category two. Category three is rarer and requires real skill. The meta-mentor — the one I aspire to be — requires something more: it requires caring less about being the source of the answer and more about what happens to the person long after they have left the room. A meta-mentor does not just create capable individuals. They create the next generation of mentors.

The professor who refused to answer. I think of a professor I had early in my education who was legendary for his refusals. When students came to him stuck on a problem, he would almost never give them the solution. He would ask them a question instead. Sometimes one question, sometimes three. And then he would wait. The waiting was deliberate — a silence that said: I believe you can find this. Students found it frustrating at first. Some found it maddening. But years later, when those same students sat with problems that no professor could solve for them, they had something no textbook had given them: a way of thinking. A method for entering the unknown without panic. They had internalized the questions he used to ask, and could now ask them of themselves — and some of them now ask those same questions of their own students. That, I think, is the meta-mentor.

V. Understand Before You Speak

Before giving any advice, the first obligation is to truly understand the person. What are they trying to achieve? What motivates them? What are their strengths, their fears, their constraints, their aspirations? Only after understanding them well should we gently nudge — and only when they are genuinely unable to move forward on their own.

A few years ago, someone came to me wanting advice on whether to leave a company where he had worked for nearly a decade. He described the situation in practical terms: the pay, the commute, the new management. I nearly responded in practical terms. But I paused, and instead of answering, I asked him what he had loved most about the job when he first started. His whole manner changed. He described it with quiet intensity — the early days, a team that felt like a family, work that felt meaningful. It became clear quickly that what he was grieving was not the job as it existed now, but the version of it that had once mattered to him. The real question was not whether to leave. It was whether anything could restore what had made it worth staying. If I had answered the surface question, I would have answered the wrong one entirely.

Listening is not a prelude to advice. It is the advice — or at least the better part of it.

Most people, when they feel genuinely heard, begin to find their own clarity. The answers were inside them all along; they just needed a patient interlocutor to help surface them.

VI. Trust Is Built Through Understanding

There is another dimension to mentorship that I have come to prize: trust. And trust, I have learned, is not built by demonstrating superiority. It is built by demonstrating understanding.

People trust those who truly see them.

The mentor nobody trusted. I once watched a senior leader attempt to mentor a younger member of his team. He was brilliant — genuinely so — and every piece of advice he offered was technically correct. But the meetings never quite landed. The younger man would leave looking vaguely deflated rather than energized. I sat in on one of these conversations and noticed what was happening: the senior leader spoke entirely in terms of what the younger man needed to improve. He was right about all of it. But he had never once acknowledged what the younger man was already doing well, never named what was already working, never signaled that he saw the person and not only the gaps. The relationship eventually dissolved quietly. The younger man started seeking guidance elsewhere — from someone who knew less, perhaps, but who made him feel seen.

Competence earns respect. Understanding earns trust. And in mentorship, trust is the lever. Without it, even correct advice fails to move anything.

VII. Strengths Before Weaknesses

A good mentor attends to strengths before weaknesses. They identify what is already working and help people recognize their own capabilities. Constantly pointing out flaws may be accurate, but it rarely inspires growth. More often, it diminishes confidence and breeds resistance.

The world is already generous with reminders of what we lack. Failure reminds us. Rejection reminds us. Comparison reminds us. A mentor’s rarer gift is to name what is already there — to point at a strength the person has stopped noticing because it has become too familiar, too close, too easy to dismiss as ordinary.

The communicator who doubted herself. I worked with someone who was a natural communicator — one of the most gifted explainers of complex ideas I have encountered. But she had internalized a story about herself as “not technical enough” and spent enormous energy trying to fix that perceived deficit, often at the cost of the thing she was genuinely exceptional at. In one of our conversations, I reflected back what I had observed: that the moments when she was most effective were precisely the moments when she was translating complexity into clarity for others. Not despite her style of thinking, but because of it. She had been trying to become someone else when the better strategy was to become more fully herself. Naming that — simply and specifically — shifted something. She stopped apologizing for the way her mind worked and started using it deliberately.

A Final Thought

Good advice is not about having answers. It is about caring enough to understand before you speak, to build trust before you lead, and to want less credit for the outcome than you secretly believe you deserve.

And if you are patient enough — if you resist the temptation to make yourself indispensable — you may arrive at something rarer still.

Perhaps the highest form of advice is not telling someone what to do.

It is helping them become the kind of person who no longer needs your advice.