Re:Work | How AI is reshaping the way we work | Part 2

Re:Work #7: How expertise gets created

Between AI agents, faster development cycles, and the growing pressure to do more with leaner teams, one thing feels increasingly clear: the next challenge of knowledge work is not just how work gets done faster, but how people still become great at it.

The shift

Everyone wants senior engineers, senior lawyers, senior consultants, and senior operators.

But that skips over a harder question: How does someone become senior in the first place?

A lot of early-career work has historically been where people built judgment.

You learned by doing the messy parts. You saw patterns. You made mistakes. You watched someone more experienced make tradeoffs in real time.

That work was not always efficient. But it was formative.

If AI automates, accelerates, or abstracts away more of that work, organizations have to be much more intentional about how experience gets created.

What I’m seeing

• Organizations get very focused on which tasks AI can optimize, but less focused on which tasks quietly teach people how the work really works.
• Leaders ask how to scale expert output, but not always how to scale expert judgment.
• A growing gap between access to answers and access to the pattern recognition behind those answers.

Moving forward

Organizations need to stop treating AI adoption as only a productivity challenge.

It is also a learning design challenge.

That means:

• Preserving the messy parts of work that build judgment, even when they look inefficient.
• Making expert reasoning more visible, not just expert output more reusable.
• Creating new apprenticeship models that combine human coaching, AI support, and deliberate exposure to real tradeoffs.

AI may make some work faster. But speed alone does not create expertise.

The companies that win the next era of work will not be the ones that simply replace junior tasks with agents.

They will be the ones that redesign how people learn, how judgment is transferred, and how expertise compounds across the organization.

Less “how do we automate the work?”

More “how do we preserve and scale the path to mastery?”

Question

As AI takes on more entry-level work, what experiences do you think we need to protect, redesign, or create so people can still build real judgment?

Re:Work #8: The shift to capability

Between leaner teams, more powerful tools, and rising expectations, one thing feels increasingly clear: team size is becoming a poor proxy for impact.

The shift

For a long time, growth meant adding more engineers, more PMs, more resources.

But as leverage increases through tooling and AI, the equation is changing. It’s now about what your team can actually do.

What I’m seeing

• Smaller teams deliver outsized results.
• Leaders rethink how they measure productivity and output.

Moving forward

There is a need to shift and start thinking in terms of capability.

That means:

• Focusing on leverage, not just capacity.
• Designing teams around outcomes
• Investing in tools and systems that amplify what individuals can do.

Question

How are you measuring team effectiveness?

Re:Work #9: The rise of the full-stack builder

Between better tools, AI-assisted development, and faster cycles, one thing feels increasingly clear: the lines between roles are starting to blur.

The shift

Historically, our industry has been specialized: PMs defined, engineers built, designers designed.

That model worked when building was slower, and coordination was the main challenge.

Now, the constraint is often speed and iteration, not just coordination.

What I’m seeing

• Broader scopes, moving from idea to execution more independently.
• Less rigid handoffs and more end-to-end ownership.
• Role boundaries start to break down.

Moving forward

Rethinking how the roles are defined and where organizations expect ownership.

That means:

• Encouraging builders to develop adjacent skills.
• Valuing end-to-end thinking, not just functional excellence.
• Redesigning teams to reduce friction between idea and execution.

This doesn’t mean specialization disappears. It means it’s no longer enough on its own.

Question

How are roles evolving on your team, and where are old boundaries slowing you down?

Re:Work #10: The importance of adaptability

Lately, I’ve been thinking about adaptability and AQ (Adaptability Quotient). Natalie Fratto's TedX talk from nearly 7 years ago feels more relevant than ever: adaptability is becoming a defining advantage, not just a nice-to-have.

The shift

For a long time, the industry optimized for IQ and EQ, what you know and how you work with others.

But in a world where roles, tools, and expectations are constantly evolving, those are no longer enough on their own.

The differentiator is AQ: adaptability quotient. Your ability to navigate change, unlearn quickly, and operate effectively in the unknown.

What I’m seeing

• High performers struggle not because they lack skill, but because the environment around them has changed.
• People with less experience ramp faster because they’re more willing to experiment and adjust.
• The individuals and teams who thrive are the ones who lean into change rather than resist it.

Moving forward

There is a need to start valuing and building adaptability as a core capability.

That means:

• Rewarding learning and iteration, not just outcomes.
• Creating environments where it’s safe to change your mind.
• Hiring and developing people based not just on what they’ve done, but how they respond when things shift.

Adaptability isn’t a soft skill. It’s a competitive advantage.

Question

How are you building your adaptability muscle?