The Octopus Organization: Building an Advisory Firm That Senses and Adapts

As a PADI certified Master Scuba Diver and rescue diver, I've logged hundreds of dives all around the world over the years. Each dive is unique, but every now and then, you see something that completely resets how you think about and view the world.

I was 80 feet underwater off the coast of Australia, diving the Great Barrier Reef. Out of the corner of my eye I spot the largest octopus I've ever seen, moving gracefully across the reef. No urgency. No wasted motion. Just total and complete awareness.

And as it moves, the octopus repeatedly changes color. Instantly. Seamlessly. It blends into whatever it travels over. Coral. Rock. Sand. You'd almost lose sight of it if you weren't paying close attention.

It wasn't reacting after the fact. It was adapting in real time.

And I clearly remember thinking: this is intelligence at a completely different level. Not force. Not speed. Just perfect environmental awareness and adaptation.

Fast forward several years to late-2025, and I come across an article published in the Harvard Business Review entitled "Become an Octopus Organization." Needless to say, it instantly caught my attention, and truth be told, I've been unable to get that image from my reef experience out of my head ever since.

How Can Your Advisory Business Emulate the Octopus' Behavior?

The article authors make a key point that hits hard. Most organizations today are still built like machines. Predictable. Controlled. Optimized for consistency. It's a model that worked exceedingly well for a very long time. But the world those organizations were built for has drastically changed:

• Clients are far more informed;
• Expectations move considerably faster;
• Talent now wants ownership, not instructions; and
• The pace of change affords little time to sit back and plan your next move.

Most firms, however, are still trying to operate with rigid structures and layered decision making – resulting in what the authors call a 'Tin Man organization.' Slow to move. Waiting for direction. And struggling to respond when the environment inevitably shifts.

But here's the part that should really bother you.

After decades of transformation efforts, only about 12% of them actually produce sustained results. That's not a small miss. It's a systemic one. Nevertheless, three critical ideas from that article have stayed with me.

Acknowledge the Shift from Complicated to Complex

In a complicated world, you can map everything out. You can build a plan, follow the steps, and achieve a predictable result. But a complex world doesn't work that way. It behaves far more like the ocean I was diving in. Small changes ripple. Conditions shift. You don't control it. You respond to it.

These days, if you're leading a firm (especially in wealth management) you're operating in precisely that kind of environment. Your clients' lives are complex. Their decisions are emotional. Their expectations evolve.

You can't script your way through that. You need people who can think, interpret, and respond in the moment.

Consider Where Intelligence Actually Sits Inside Your Organization

In a lot of firms, decision-making still climbs a ladder. Information moves up. Decisions come back down. But that lag is where opportunities die.

What the article describes is something very different. The people closest to the client (and therefore closest to the problem) have the ability to act. Not recklessly, but with context, clarity, and trust.

When that happens, something shifts. Team members stop feeling like they're executing tasks and start acting like owners. They listen differently. They care more. And they identify opportunities and potential challenges earlier. That's where innovation actually comes from – not from a strategy meeting, but from the front lines.

There's a data point in the article that has stuck with me: organizations that are deeply focused on creating value for customers are more than three times as likely to lead in revenue growth and generate meaningfully higher profitability.

That doesn't come from a better org chart. It comes from how people think and behave day-to-day.

Accept That Your Role Needs to Change

You are no longer the person with all the answers. Rather, you're the person responsible for the environment. This is the one idea that most often challenges advisory leaders.

The authors describe the need for leaders to step back from directing work and instead focus on shaping the system by removing friction, creating clarity, and making ownership visible.

For a lot of firm founders, this is an extremely uncomfortable undertaking because it requires a significant degree of letting go. But if you forego this step, everything in the organization will still run through you – a bottleneck constraint that threatens the future of your enterprise.

Don't get me wrong. In no way am I trying to make a case for adding another initiative. Rather, I'm urging you to face a simple reality. The environment has changed. And it's the firms that learn how to adapt inside this new environment, in real time, who will be the ones that grow, scale, and ultimately endure. The rest will keep trying to push harder on systems that were built for a different world. And that's a strategy which rarely ends well.

Time and again I keep coming back to that incredible moment underwater. That octopus didn't stop and ask what it should do next. It didn't wait for direction. It didn't freeze-up when the environment changed.

It sensed. It adapted. It moved. And every part did so working in tandem and harmony; even though each arm was more than capable of operating independently.

That's the model you should be striving to emulate. Not control, but coordination. Not rigidity but fluidity.

This article draws on ideas discussed in the upcoming book The Octopus Organization written by Jana Werner and Phil Le Brun, both of whom are executives in residence of enterprise strategy at Amazon Web Services in London where they advise Fortune 500 executive teams on designing adaptive, customer-centric organizations.

It's well worth a read – especially if you're leading a growing firm and feeling the strain between how your business is built and what the market is demanding.

Questions Financial Advisors Often Ask

What is the Octopus Organization model and how does it apply to financial advisory firms?

The Octopus Organization is a concept discussed in a Harvard Business Review article that contrasts adaptive, sensing organizations with rigid, machine-like ones. Most organizations today are still built like machines—predictable, controlled, and optimized for consistency. The Octopus Organization model describes firms that can sense, adapt, and move in real time, where every part works in tandem and harmony even though each arm is more than capable of operating independently. For financial advisory firms, this means shifting from rigid structures and layered decision making to an environment where people closest to the client have the ability to act with context, clarity, and trust.

What is a Tin Man organization and why is it a problem for advisory firms?

A Tin Man organization is a term used in the Harvard Business Review's Octopus Organization article to describe firms with rigid structures and layered decision making. These organizations are slow to move, waiting for direction, and struggling to respond when the environment inevitably shifts. Most firms are still trying to operate this way, even though clients are far more informed, expectations move considerably faster, talent now wants ownership not instructions, and the pace of change affords little time to sit back and plan your next move.

What is the difference between a complicated and a complex environment for financial advisors?

In a complicated world, you can map everything out, build a plan, follow the steps, and achieve a predictable result. But a complex world doesn't work that way. It behaves far more like the ocean—small changes ripple, conditions shift, and you don't control it, you respond to it. Financial advisory leaders are operating in precisely that kind of complex environment. Clients' lives are complex, their decisions are emotional, and their expectations evolve. You can't script your way through that. You need people who can think, interpret, and respond in the moment.

Why do most organizational transformation efforts fail?

After decades of transformation efforts, only about 12% of them actually produce sustained results. That's not a small miss—it's a systemic one. Most firms are still trying to operate with rigid structures and layered decision making, resulting in organizations that are slow to move, waiting for direction, and struggling to respond when the environment inevitably shifts.

Where should decision-making sit inside a financial advisory firm?

In a lot of firms, decision-making still climbs a ladder—information moves up and decisions come back down. But that lag is where opportunities die. The people closest to the client, and therefore closest to the problem, should have the ability to act—not recklessly, but with context, clarity, and trust. When that happens, team members stop feeling like they're executing tasks and start acting like owners. They listen differently, they care more, and they identify opportunities and potential challenges earlier. That's where innovation actually comes from—not from a strategy meeting, but from the front lines.

What does research say about organizations focused on creating value for customers?

According to a data point in the Harvard Business Review's Octopus Organization article, organizations that are deeply focused on creating value for customers are more than three times as likely to lead in revenue growth and generate meaningfully higher profitability. That doesn't come from a better org chart—it comes from how people think and behave day-to-day.

How does the role of an advisory firm leader need to change in an adaptive organization?

You are no longer the person with all the answers—rather, you're the person responsible for the environment. The authors describe the need for leaders to step back from directing work and instead focus on shaping the system by removing friction, creating clarity, and making ownership visible. For a lot of firm founders, this is an extremely uncomfortable undertaking because it requires a significant degree of letting go. But if you forego this step, everything in the organization will still run through you—a bottleneck constraint that threatens the future of your enterprise.

What is the core leadership lesson of the Octopus Organization for financial advisors?

The octopus didn't stop and ask what it should do next. It didn't wait for direction. It didn't freeze up when the environment changed. It sensed, it adapted, it moved—and every part did so working in tandem and harmony, even though each arm was more than capable of operating independently. That's the model advisory firms should be striving to emulate. Not control, but coordination. Not rigidity, but fluidity. It's the firms that learn how to adapt inside this new environment, in real time, who will be the ones that grow, scale, and ultimately endure.