GUEST POST from Robyn Bolton

The business press has a new obsession with courageous leadership.

Harvard Business Review dedicated their September cover story to it. Nordic Business Forum built an entire 2024 conference around it. BetterUp, McKinsey, and dozens of thought leaders and influencers can’t stop talking about it.

Here’s what they’re all telling you: If you’re playing it safe, stuck in analysis paralysis, not innovating fast enough, or not making bold moves, then you are the problem because you lack courage.

Here’s what they’re not telling you: You don’t have a courage problem. You have a systems problem.

The Real Story Behind “Courage Gaps”

The VP was anything but cowardly. She had a track record of bold moves and wasn’t afraid of hard conversations. The CEO wanted to transform the company by moving from a product-only focus to one offering holistic solutions that combined hardware, software, and services. This VP was the obvious choice.

Her team came to her with a ideas that would reposition the company for long-term growth. She loved it. They tested the ideas. Customers loved them. But not a single one ever launched.

It wasn’t because the VP or the CEO lacked courage. It was because the board measured success in annual improvements, the CEO’s compensation structure rewarded short-term performance, and the VP required sign-off from six different stakeholders who were evaluated on risk mitigation. At every level, the system was designed to kill bold ideas. And it worked.

This is the inconvenient truth the courage press ignores.

That success doesn’t just require leaders who are courageous, it requires organizational architecture that systematically rewards courage and manages risk.

What We’re Really Asking Leaders to Overcome

Consider what we’re actually asking leaders to be courageous against:

• Compensation structures tied to short-term metrics
• Risk management processes designed to say “no”
• Approval hierarchies where one skeptic can overrule ten enthusiasts
• Cultures where failed experiments end careers

The courage discourse lets broken systems off the hook.

It’s easier to sell “10 Ways to Build Leadership Courage” than to admit that organizational incentives, governance structures, and cultural norms are actively working against the bold moves we tell leaders to make.

What Actually Enables Courageous Leadership.

I’m not arguing that there isn’t a need for individual courage. There is.

But telling someone to “be braver” when their organizational architecture punishes bravery is like telling someone to swim faster in a pool filled with Jell-O.

If we want courage, we need to fix the things the systems that discourage it:

• Align incentives with the time horizon of the decisions you want made
• Create explicit permission structures for experimentation
• Build decision-making processes that don’t require unanimous consent
• Separate “learning investments” from “performance expectations” when measuring results
• Make the criteria for bold moves clear, not subject to whoever’s in the room

But doing this is a lot harder than buying books about courage.

The Bottom Line

When you fix the architecture, you don’t need to constantly remind people to be brave because the system enables. Individual courage becomes the expectation, not the exception.

The real question isn’t whether your leaders need courage.

It’s whether your organization has the architecture to let them use it.

If you can’t answer that question, that’s not a courage problem.

That’s a design problem.

And design is something that, as a leader, you can actually control.

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GUEST POST from Robyn Bolton

“Is this what the dinosaurs did before the asteroid hit?”

That was the first question I was asked at IMPACT, InnoLead’s annual gathering of innovation practitioners, experts, and service providers.

It was also the first of many that provided insight into what’s on innovators and executives’ minds as we prepare for 2026

How can you prevent failure from being weaponized?

This is both a direct quote and a distressing insight into the state of corporate life. The era of “fail fast” is long gone and we’re even nostalgic for the days when we simply feared failure. Now, failure is now a weapon to be used against colleagues.

The answer is neither simple nor quick because it comes down to leadership and culture. Jit Kee Chin, Chief Technology Officer at Suffolk Construction, explained that Suffolk is able to stop the weaponization of failure because its Chairman goes to great lengths to role model a “no fault” culture within the company. “We always ask questions and have conversations before deciding on, judging, or acting on something,” she explained

How do you work with the Core Business to get things launched?

It’s long been innovation gospel that teams focused on anything other than incremental innovation must be separated, managerially and physically, from the core business to avoid being “infected” by the core’s unquestioning adherence to the status quo.

The reality, however, is the creation of Innovation Island, where ideas are created, incubated, and de-risked but remain stuck because they need to be accepted and adopted by the core business to scale.

The answer is as simple as it is effective: get input and feedback during concept development, find a core home and champion as your prototype, and work alongside them as you test and prepare to launch.

How do you organize for innovation?

For most companies, the residents of Innovation Island are a small group of functionally aligned people expected to usher innovations from their earliest stages all the way to launch and revenue-generation.

It may be time to rethink that.

Helen Riley, COO/CFO of Google X, shared that projects start with just one person working part-time until a prototype produces real-world learning. Tom Donaldson, Senior Vice President at the LEGO Group, explained that rather than one team with a large mandate, LEGO uses teams specially created for the type and phase of innovation being worked on.

What are you doing about sustainability?

Honestly, I was surprised by how frequently this question was asked. It could be because companies are combining innovation, sustainability, and other “non-essential” teams under a single umbrella to cut costs while continuing the work. Or it could be because sustainability has become a mandate for innovation teams.

I’m not sure of the reason and the answer is equally murky. While LEGO has been transparent about its sustainability goals and efforts, other speakers were more coy in their responses, for example citing the percentage of returned items that they refurbish or recycle but failing to mention the percentage of all products returned (i.e. 80% of a small number is still a small number).

How can humans thrive in an AI world?

“We’ll double down,” was Rana el Kaliouby’s answer. The co-founder and managing partner of Blue Tulip Ventures and host of Pioneers of AI podcast, showed no hesitation in her belief that humans will continue to thrive in the age of AI.

Citing her experience listening to Radiotopia Presents: Bot Love, she encouraged companies to set guardrails for how, when, and how long different AI services can be used.  She also advocated for the need for companies to set metrics that go beyond measuring and maximizing usage time and engagement to considering the impact and value created by their AI-offerings.

What questions do you have?

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The Not So Obvious or Easy Answer

GUEST POST from Robyn Bolton

Last week, I shared that 74% of executives believe that their organizations will cease to exist in ten years. They believe that strategic transformation is required, but cite the obvious problem of organizational  inertia and the easy scapegoat of people’s resistance to change.

Great.  Now we know the problem.  What’s the solution?

The Obvious: Put the Right People in Leadership Roles

Flipping through the report, the obvious answers (especially from an executive search firm) were front and center:

• Build a top team with relevant experience, competencies, and diverse backgrounds
• Develop the team and don’t be afraid to make changes along the way
• Set a common purpose and clear objectives, then actively manage the team

The Easy: Do Your Job as a Leader

OK, these may not be easy but it’s not that hard, either:

• Relentlessly and clearly communicate the why behind the change
• Change one thing at a time
• Align incentives to desired outcomes and behaviors
• Be a role model
• Understand and manage culture (remember, it’s reflected in the worst behaviors you tolerate)

The Not-Obvious-or-Easy-But-Still-Make-or-Break:  Deputize the Next Generation

Buried amongst the obvious and easy was a rarely discussed, let alone implemented, choice – actively engaging the next generation of leaders.

But this isn’t the usual “invite a bunch of Hi-Pos (high potentials) to preview and upcoming announcement or participate in a focus group to share their opinions” performance most companies engage in.

This is something much different.

Step 1: Align on WHY an “extended leadership team” of Next Gen talent is mission critical

The C-Suite doesn’t see what happens on the front lines. It doesn’t know or understand the details of what’s working and what’s not. Instead, it receives information filtered through dozens of layers, all worried about positioning things just right.

Building a Next Gen extended leadership team puts the day-to-day realities front and center. It brings together capabilities that the C-Suite team may lack and creates the space for people to point out what looks good on paper but will be disastrous in practice.

Instead, leaders must commit to the purpose and value of engaging the next generation, not merely as “sensing mechanisms” (though that’s important, too) but as colleagues with different and equally valuable experiences and insights.

Step 2: Pick WHO is on the team without using the org chart

High-potentials are high potential because they know how to succeed in the current state. But transformation isn’t about replicating the current state. It requires creating a new state.  For that, you need new perspectives:

• Super connecters who have wide, diverse, and trusted relationships across the organization so they can tap into a range of perspectives and connect the dots that most can barely see
• Credible experts who are trusted for their knowledge and experience and are known to be genuinely supportive of the changes being made
• Influencers who can rally the troops at the beginning and keep them motivated throughout

Step 3: Give them a clear mandate (WHAT) but don’t dictate HOW to fulfill it

During times of great change, it’s normal to want to control everything possible, including a team of brilliant, creative, and committed leaders. Don’t involve them in the following steps and be open to being surprised by their approaches and insights:

• At the beginning, involve them in understanding and defining the problem and opportunity.
• Throughout, engage them as advisors and influencers in decision-making (
• During and after implementation, empower them to continue to educate and motivate others and to make adaptations in real-time when needed.

Co-creation is the key to survival

Transforming your organization to survive, even thrive, in the future is hard work. Why not increase your odds of success by inviting the people who will inherit what you create to be part of the transformation?

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According to Executives

GUEST POST from Robyn Bolton

One day, an architect visited the building site of his latest project. There he saw three people all laying bricks. He asked each what they were doing. “I’m laying bricks,” the first responded. “I’m building a wall,” said the second.  “I’m building a cathedral,” exclaimed the third.

The parable of the Three Bricklayers is a favorite amongst motivational speakers, urging their audiences to think beyond today’s tasks and this quarter’s goals to commit to a grandiose vision of eternal success and glory.

But there’s a problem.

The narrative changed

The person who had a vision of building a cathedral? They now believe they’re building ruins.

Is the C-Suite Quietly Quitting?

Recently published research found that three out of four executives believe that “without fundamental transformation* their organization will cease to exist” in ten years. That’s based on data from interviews with twenty-four “current or former CEOs who have led successful transformations” and 1,360 survey responses from C-Suite and next-generation leaders.

And, somehow, the news gets worse.

While 77% of C-suite executives report that they’re committed to their companies’ transformation efforts, but 57% believe their organization is taking the wrong approach to that transformation. But that’s still better than the 68% of Next-Gen executives who disagree with the approach.

So, it should come as no surprise that 71% of executives rate their companies’ transformation efforts as not at all to moderately successful. After all, it’s hard to lead people along a path you don’t agree with to a vision you don’t believe in.

Did they just realize that “change is hard in human systems?”

We all fall into the trap of believing that understanding something results in commitment and change.

But that’s not how humans work.

That’s definitely not how large groups of humans, known as organizations, work.

Companies’ operations are driven only loosely by the purpose, structures, and processes neatly outlined in HR documents. Instead, they are controlled by the power and influence afforded to individuals by virtue of the collective’s culture, beliefs, histories, myths, and informal ways of working.

And when these “opaque dimensions” are challenged, they don’t result in resistance,

They result in inertia.

“Organizational inertia kills transformations”

Organizations are “complex organisms” that evolve to do things better, faster, cheaper over time. They will continue doing so unless changed by an external force (yes, that’s Newton’s first law of motion).

That external force, the drive for transformation, must be strong enough to overcome:

1. Insight Inertia stops organizations from getting started because there is a lack of awareness or acceptance amongst leaders that change is needed.
2. Psychological Inertia emerges when change demands abandoning familiar success strategies. People embrace the idea of transformation but resist personal adaptation, defaulting to comfortable old behaviors.
3. Action Inertia sets in and gains power as the long and hard work of transformation drags on. Over time, people grow tired. Exhausted by continuous change, teams progressively disengage, becoming less responsive and decisive.

But is that possible when 74% of executives are simply biding their time and waiting for failure?

“There’s a crack in everything, that’s how the light gets in.”

Did you see the crack in all the doom and gloom above?

• 43% of executives believe their organizations are taking the right approach to transformation.
• 29% believe that their organizations’ transformations have been successful.
• 26% believe their company will still be around in ten years.

The majority may not believe in transformation but only 33% of bricklayers believed they were building a cathedral, and the cathedral still got built.

Next week, we’ll explore how.

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