Throw The Box Away

Reimagining how we work in the age of AI

I’ve been having a lot of conversations lately about how roles will change because of AI—and how we re-skill workers to perform them as a result.

(I know what you’re thinking—I must be really fun at parties. 🙄)

There’s general agreement that AI will change the nature of work. Accountants and lawyers, marketers and salespeople, product managers and software developers, school administrators and professors … these roles and so many more will change.

But how? Who the eff knows. There are a lot of theories—and a lot of LinkedIn posts—but no matter how confidently they tell you, no one knows for sure.

Slap some AI on that

We’re in the very early days of a new technology and like so many new technologies before it, we’re mostly just slapping AI on top of existing processes and models.

Remember the early days of the Internet? Company websites were primarily marketing brochures, sans that freshly printed smell. IYKYK.

As a CIO I saw this all the time. We added computers to classrooms but the process remained the same. PowerPoint slides replaced overhead transparencies but nothing else really changed—except the cost to equip and maintain classrooms went up exponentially.

Or my own personal favorite (and by favorite I mean nightmare): we brought in new enterprise systems with amazing capabilities and then spent millions of dollars and years of time making the shiny new system behave exactly like the old one, which had processes designed solely based on system limitations—not actual need. 🤦🏼‍♀️

It’s not new. It’s not unexpected. And it’s totally okay that this is the stage we’re in. We just have to stop pretending that we’re not.

The challenge is moving beyond this stage.

The skills we actually need

Humans are remarkably resistant to change. Organizations even more so. Knowing this, how do we:

• Build more adaptable and resilient companies?

• Create cultures oriented around continuous learning and improvement?

• Enable students and employees to be builders and innovators—creators, not consumers?

This is the upskilling we actually need.

We can’t train someone for an AI-enabled role right now. There are no real models for how those roles will work—and the technology is changing so quickly that anything we teach today could be obsolete within a month.

We need to help our teams imagine a whole new way of working.

Not the current processes and deliverables augmented with AI (this is mainly what I wrote about in Leveling Up With AI). Not a “thinking outside the box” type of exercise. We need to start from a blank slate—asking ourselves, “if this job didn’t exist, how would we design it today?”

That’s extremely hard to do. If it is even possible, it requires at least two things:

• The ability to step outside the role and work backwards from the outcomes it’s meant to drive

• Consistent time and space to experiment with new technologies—and figure out how they help achieve those outcomes

This isn’t a one-time activity. It requires continual reinvention of our work. Who’s got time for that?

I don’t know about you, but I rarely have time to get everything done on my ever-growing list of things to do, much less play with AI to reimagine my role from the ground up. And I work for an AI company.

Our challenge as leaders

As I was writing this blog, I came across a friend’s LinkedIn post talking about an AI conference they’re planning to attend. The conference agenda included this note:

“the real value lives in how work is redesigned, not the technology deployed”

Exactly. As leaders, we must rise to this challenge.

If we want to lead in the age of AI, we need to tackle the very nature of work itself. Our company cultures. How we structure time and measure productivity. The value we place on experimentation and change.

We need to set the expectation that our team members’ roles and work will continually evolve, and we need to provide the tools and space to enable it.

The problem isn’t AI. It never was. It’s getting ourselves—and our teams—comfortable with constant change.

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Bonus: I’ve been talking about “thinking outside the box” for a long time, it seems. Here’s a 2013 video where I talk about throwing the box away:

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