Pedro Silva's Blog

I keep hearing people ask AI questions they have not tried to answer themselves. A difficult email arrives, and before deciding what they think, they ask the machine how to respond. A choice appears, and the first instinct is to prompt it rather than think it through.

The tool is useful, but the order matters. When AI becomes the first step, it removes the part where a view begins to form.

For years, I thought I was building trust by letting my team know which decisions I disagreed with. Reading Serve Up, Coach Down, I realised that what felt like transparency was quietly undermining the very decisions I expected my team to support.

Nathan Jamail makes a distinction that I will always remember. Before a decision, my job is to contribute honestly, challenge assumptions and bring my best thinking. Once the decision is made, my job changes. My team no longer needs to know how hard I argued. They need someone who will help them succeed within the chosen direction.

Not everything that got you here deserves to be trusted. Some of it just survived.

Marshall Goldsmith calls it the success delusion. Once something has worked, we confuse the behaviours that produced the result with the behaviours that survived it.

The people he coaches are not failing. They are already successful. Their problem is smaller and harder to see: the higher you go, the more a suggestion sounds like an order. Nobody tells you.

I read an old article this week. “Let’s Hear It for B Players,” Harvard Business Review, June 2003. The argument is that companies chase stars and neglect the steady performers who keep the place running, and that this is a costly mistake. 23 years later it still circulates, which is either a compliment to the writing or a sign nothing changed.

What caught me was the label, more than the argument itself. B player. We took the grade from school, where a B means good but not top, and we now apply it to adults as if a whole working life could sit on one scale. The scale measures something. I am less sure it measures what we think it does.

I was again in another meeting where AI appeared before the agenda come up. Not because we were there to discuss it. It has simply become the slide every strategy deck seems to need, somewhere between growth and efficiency.

What I can’t tell, sitting in those rooms, is whether we keep raising it because it matters that much or because everyone else is raising it. Either way, I am less convinced than I was that AI itself will be the advantage.

I used to think minimalism was about owning fewer things, the white walls and bare shelves that fill every minimalist photograph. Over time I started to doubt that. What gets removed in those photographs is visible. What is actually being reduced, I think, is something else: the number of decisions a life demands.

Every possession asks for something. It has to be stored and maintained, and eventually repaired or replaced. Every commitment keeps a piece of your attention long after you agreed to it, and information behaves the same way: an article saved for later, a podcast still in the queue, a browser tab that insists you revisit it. None of this feels heavy by itself. Together it adds up to a day full of small obligations nobody decided on purpose.

For 603 weeks I have kept my thinking in the same place. Workflowy holds 11000 bullets now. Ideas, half-formed arguments, todos, plans, the shape of projects I have not started. When I want to know what I think, I open it and look.

It has been there the whole time. While everything around it changed, the place stayed the same. This is the tool that keeps my life in order.

A job posting I came across last week was for a fractional executive assistant. Not a fractional executive, an assistant to one, split across however many people needed a slice of her calendar. I found myself wondering how much of any of those calendars she actually holds in her head.

Fractional work has spread well past the C-suite by now. Executives sell their time in slices. Owners hold stakes instead of companies. Even the people who support those executives get sliced the same way. Friendships get described this way too, half present, already checking the time on the way out.

Success: The predictable result of hard work, patience, sacrifice, and learning put into practice every day.

One bag, two jobs done well. And an observation about why I like it so much.

I recently bought the Knack Pack Small 2 and I’ve been using it consistently for commuting (when I have to commute, that is, because I work a lot from home). And as it expands for short one or two day trips, it’s a perfect bag doing two jobs. That is the practical reason I bought it, and the practical reason holds. It is genuinely good at both.