A Courageous Conversation About the Past, Present, and Future of Leadership With Kyle Hermans — Founder & CEO, Be Courageous, and Gary A. Bolles — Chair for the Future of Work, Singularity University & Author of The Next Rules of Work
How many times have you shown up to work and received an email describing yet another new software, methodology, skill set, or tool that you’re asked to learn and embody immediately? We’ve all had the feeling of, “Wait, I need to learn yet another new protocol? I just got the swing of the most recent change!”
Leaders have to not only make adjustments themselves, but also motivate their teams to get on board with the “shiny new way.” And to make it more difficult, taking months to get up to speed is not an option — because by then it will change again!
Lately, we’ve noticed an increased cause of friction within teams because a leader is attached to “the old ways” of running their teams and businesses. We can also sympathize with those leaders. It’s normal to resist change: Humans are wired for comfort and stability, and it’s increasingly harder to adapt in a world of exponential change.
These “set in their ways” leaders want to continue doing what worked in the past. However, old leadership tactics, thinking, and mental models that once helped run efficient and productive factories during the industrial era are, for many reasons, no longer effective in the present and future eras.
Leaders who achieved success using older methods often find themselves stuck in a time bubble of their heyday. In Carol S. Dweck’s book, Mindset: New Psychology of Success, denying modern changes and clinging to the past would be a “fixed” mindset. There is nothing inherently wrong with a fixed mindset — except that it doesn’t prepare us for continuous change. These leaders are also often stuck in an “expert” mindset, thinking, “I’ve been through this before, I know what I’m doing, and this is going to be like all the other times.”
They would be wrong. Nothing in the future will resemble what it is today.
Changes in Leadership Needs
If you lead a team, a division, or an entire organization, a world of exponential change demands that you leave behind yesterday’s mindset.
- Today’s leaders can no longer focus on operational or creative expertise. They must be ambidextrous.
- Leaders must navigate a tech-heavy, AI-driven world. And they have to be connected to that world and their teams from a device they keep in their pockets, 24/7.
- Market disruptions used to occur once a decade; now they happen daily. It’s never been easier to start a business and knock a major player off its pedestal. At the same time, it’s never been harder to stay in business due to unexpected changes in the market, technology, and policies.
- Employees are no longer motivated by the fear of punishment. Leaders are tasked with ensuring that humans feel safe and heard, and creating the conditions for them to thrive in a tech-forward future. And they must do this while “doing well and doing good,” achieving sustainability goals (such as the SDGs), and trying to align business and profit goals with the well-being of the Earth.
And as if all that isn’t enough… - Today’s leaders must navigate significant generational shifts in the attitudes and motivations of various age groups within a single organization. There can be a big difference in how a Baby Boomer, a Millennial, or a Gen Z person thinks through problems, approaches their work, or what gives them purpose and motivates them. In fact, the mindset of today’s youth is so different that instead of thinking of them as a new generation, we might even consider them as a new human species, with vastly different experiences and motivations than their predecessors. They often have far more optionality in their work and in their lives — and they want you to support their needs.
Whether you’re a new manager of one person or a CEO of a company with 10,000+ employees, here’s how leadership mindsets, skillsets, and styles have shifted, as well as our best thinking on what’s coming next.
“The Old Rules” of Leadership
Question: What did the mindsets, skills, and styles of leadership look like in the past? And why did it work back then?
Gary: The “old rules” of work were born in the Industrial Era, when factory floors and assembly lines encouraged practices like command-and-control management, hierarchy, and measuring productivity by time and output. Those ways of working were created to ensure predictability, stability, and scalability.
Kyle: Exactly. Much of it came from military-era leadership models as well—order, discipline, chain of command. That system was great when the goal was to maximize production with minimal error and have a common enemy/competitor. But the world isn’t linear anymore. Humans aren’t machines, and we’re no longer following a single path to success. Predictability with forecasts is out the window. We live in a much more dynamic era with less control.
Authoritarian control is not what’s desired now. If you told a young person starting a job nowadays, “You really need to suffer to succeed and obey the command of a single person,” they’ll reply, “Hell, no.”
It used to be that a person would get a job somewhere and climb up the career ladder, working at the same company for decades, where they’d eventually cash in a nice pension and retire. Humans have a multitude of choices now, and they can (and do) easily switch to a new company.
Old Mindsets Looked Like:
- “Suffer to succeed”
- Command-and-control
- Authoritarianism
- Hierarchical structures (everything has to flow upward)
- Looking at the past to inspire or solve a future problem
- Management-by-walking-around (AKA management by surveillance)
- Don’t decide until you have all the information
- Know-it-all vs Learn-it-all mentality
- Lead/inspire using negative consequences
“The Now” of Leadership
Question: What’s popular in leadership today?
Kyle: Now we see leaders emphasizing purpose, psychological safety, and bold experimentation. Companies are trying to build not only cultures of trust but also creativity and play. We’re seeing companies make an effort to take care of their workforce more holistically, so they stay longer, such as by adding resources like daycare, fitness rooms, and social events. There is also a focus on encouraging people to thrive in ambiguity. Buzzwords like VUCA (volatile, uncertain, complex, ambiguous) and antifragile are everywhere. And let’s not forget the sexiest new object in the room, “AI.”
AI is like an alien ship in a movie floating above New York City. Everyone is looking up at it and saying, “Ooooh, what’s that? Is it good or bad?” I’ve attended over 20 AI workshops per year since 2018 on this topic. We are the last generation that will have seen a time when we only managed humans.
Gary: Yes! AI tools may make it easier to send more emails, summarize meetings, or define job roles, but there’s a ton of confusion on how best and how far to integrate them, by whom, and for what purpose. Leaders are being tasked with using AI without a clear strategy, so it appears they’re on the cutting edge with their bosses, shareholders, and customers. But buzzwords are empty unless they are thoughtfully implemented and role modeled. And treating the AI tsunami as just another new technology misses a generational opportunity to catalyze continuous organizational transformation.
“Now” Mindsets Look Like:
- Purpose-driven leadership
- Empowerment and trust-building
- Experimentation & innovation
- Psychological safety
- Wellness & retention programs
- AI for the sake of saying they use AI
“The Next” of Leadership
Question: What will leadership look like in the future?
Gary: What happens next with leadership is what I wrote about in my book, The Next Rules of Work: The Mindset, Skillset, and Toolset to Lead Your Organization through Uncertainty. Organizational structures will evolve into WorkNets (fluid, networked, highly-distributed organizations). Leaders will need SCALE skills: synchronizing, coordinating, accountability, learning, and evolving. Workers will need PACE skills: problem-solving, adaptability, creativity, and empathy. And these next mindsets and skillsets can all be powered by the AI toolset.
Kyle: Totally agree. And the next era will be all about courage and imagination. AI will fundamentally reshape organizations. Younger generations expect flexibility, purpose, and balance in their use of technology. Leaders must unlearn as fast as they learn.
Experimenting, imagining, and surfing the waves of disruption will be needed. Antifragile will remain a valuable practice, as will the concepts of “red ocean” and “blue ocean.”
Disruption mapping, trend spotting, and co-creation with customers will continue to be effective into the future.
Any mindset or method that allows you to think of the “now” while also preparing for the “next” will serve a leader well, like using a short-term response skill set with a long-term activation skill set.
It takes courage to swim into unknown waves, to fail, to fall, to try, to learn, to let something go, and to try something new.
So I’d say the most critical skill that will never go out of style is this: Courage.
“Next” Mindsets Will Look Like:
- Critical thinking + foresight
- Courageous conversations
- Human-AI collaboration
- Emotional & adaptability intelligence (EQ + AQ)
- Continuous unlearning & reinvention
Quick Reference: Old → Now → Next
What to Do If You’re Stuck in “Old Ways”
Gary: The first step of changing any behavior is always to acknowledge you have a problem. Is your team moving as quickly and independently as you want? If not, look at the list of “old rules” practices, and see how many you’re still using, how they may or may not be serving you anymore — and pick the first one to jettison from your own practices.
Kyle: If you’re still using “the old ways,” it means you’re stuck in an outdated mental model and system within your company. Your outdated language and methods are keeping it stuck.
Instead, try solving for the present from the future. The way to do something different is to start thinking differently. What’s the next version of you? Think about the language, behaviors, mindsets, toolsets, and skillsets necessary to get there. Then you’ll start catching yourself and begin to think of doing things in a new way.
One of the best ways to start is to follow the Transforming Performance model.
Final Advice from Kyle & Gary
Gary: The hard truth is, everything you’re doing now will be outdated at some point, and it’ll probably happen faster than you think. The key skill for anticipating the need for change is foresight—looking out 5–10 years ahead—while remaining adaptable in the moment.
As someone who leads a team or an organization, look to others to transform their mindsets and skillsets. But it starts with you. Suppose you treat this unique moment in human history as an opportunity for your own continuous transformation in leading. In that case, you will inspire those who work with you to transform continually as well.
Kyle: I like to help people realize that any disruption that catches you off guard is a failure of imagination. You didn’t expect it because you didn’t imagine it could happen. Preparation is everything. Make your approach as evergreen as possible.
Train your team to recognize and interpret signals and trends. A great example is a company we’ve worked with that has teams assigned to the future, even if they don’t know what that future is. Once a team member completes a 2025 launch, they join a 2027 team to start building what’s next. And so on. Brilliant!
And get ready for the next round of generation to hit the workforce. I have four kids, and I see how differently they engage with and what they expect from the world around them. The line between the physical and metaphysical worlds is becoming increasingly blurred every day.
Build courageous leadership practices into your daily work. That way, you’re not just reacting to change — you’re imagining and creating what’s next.
Ready to Take the Next Step?
This is a watershed moment for leadership. Old rules won’t carry us forward, and today’s methods won’t last forever. Will you lead with courage into the future?
- Learn more about WorkNets, SCALE, and PACE in Gary’s book, The Next Rules of Work.
- Explore Be Courageous frameworks and free tools here.
- Bring Gary and Kyle into your organization to facilitate mindblowing workshops!
Co-written/edited: Shannon Geher
Research & Image: FIN
