







Perceiving the layers of context in problems will unlock another stage of career progression as a Staff-plus engineer, but there’s at least one essential skill to develop afterwards: navigating ambiguity. In my experience, navigating deeply ambiguous problems is the rarest skill in engineers, and doing it well is a rarity. It’s sufficiently rare that many executives can’t do it well either, although I do believe that all long-term successful executives find at least one toolkit for these kinds of problems.
The Architect of Constraints: Why Context Engineering Is the Human Skill That Matters
“If I had an hour to solve a problem, I’d spend 55 minutes defining the problem and 5 minutes solving it.” — Albert Einstein

Ambiguity, legibility, and working in the open – ambiguiti.es
The Biggest Mistake I See Engineers Make
Throughout my career, the biggest mistake I see engineers make is doing too much work on their own before looping in others. I’ve experienced this mistake as both an IC and a manager. As an IC, it’s a mistake I made many, many times early in my ow...
Layers of context.
Recently I was chatting with a Staff-plus engineer who was struggling to influence his peers. Each time he suggested an approach, his team agreed with him, but his peers in the organization disagreed and pushed back. He wanted advice on why his peers kept undermining his approach. After our chat, I followed up by talking with his peers about some recent disagreements, and they kept highlighting missing context from the engineer’s proposals. As I spoke with more peers, the engineer’s problem became clearer: the engineer struggled to reason about a problem across its multiple layers of context.

People Spend Too Much Time On Decisions with Equally Satisfying Outcomes
The pitfalls of analysis paralysis

Troubleshooting: The Skill That Never Goes Obsolete
Much of what I do, in multiple fields, could be reduced to one skill: troubleshooting. I’ll define troubleshooting as systematically determining the cause of unwanted behaviour in a system, and fixing it. Troubleshooting is often learned tacitly, in the process of explicitly learning “the skill”. Troubleshooting is rarely discussed

Don't Feed the Thought Leaders
In this article, the author shares their experience as an engineering manager and the challenges they faced when trying to reach alignment and prev...

How I stopped worrying and learned to love the easy fix
On the balance between perfect solutions and pragmatic fixes in software engineering
Engineering managers have a new job description
Why engineering managers are expected to be hands-on again and how AI tools are making it possible to stay technically sharp while still leading.

3 Mental Shifts Highly Successful People Make Right Before Their Careers Take Off
Prioritize "clarity over cleverness."

You don't have to be smart if you can think clearly
When you’re on fire, problems are transparent: they’re solved simply by the act of looking at them. Even complicated layers of multiple problems can simply be glanced through like stacked panes of glass. But nobody can work that way all the time.

Programmer as wizard, programmer as engineer
Context matters. Sometimes we need to get things done, sometimes we need to build things to last.

Stuck? Diagrams help. - Abby Covert, Information Architect
Stuck? Diagrams help. When was the last time you felt stuck? Maybe it was because of a decision you were struggling to make, a complex topic you were

VUCA Revisited: Acting Skillfully in Uncertain Times
A framework for skillful decision-making under turbulent conditions.

"the crucial step in crisis engineering is to re-establish a common view which corresponds to reality – to restore sense-making. Once that step has been taken, actually solving the problem becomes a tractable task, and without it nothing is going to work" -- @dsquareddigest.bsky.social
a failure of sense making
backofmind.substack.com