Managing in the Age of Uncertainty
Summing it all up: AI's impact on work
I was recently interviewed by cassie as part of her “guest mentor” series on her super-interesting career<hack> Substack newsletter. I wanted to share the interview with my readers as it “sums up” AI’s impact on managing and career planning.
Introduction
AI’s biggest impact? Making the career ladder an artifact of the boomer generation. As every function and job role rethinks itself around AI, the predictable path of climbing step-by-step up a hierarchy doesn’t reflect how careers actually work anymore. Instead, we’re building what some call “portfolio careers”—a collection of chapters and experiences that tell a coherent story about who you are and what you do exceptionally well. The challenge? Most people don’t start with the right foundation: their actual strengths.
Cassie: You’ve said the corporate ladder is dead and we need to think in terms of career stories instead. What does that shift actually mean for how we think about our careers?
Ron: The age of the predictable career ladder—where you took clear steps up a hierarchy over the course of decades and often with the same manager—is over. We’re now in what I call the “Age of Uncertainty,” where there’s no obvious ladder and no predictable path because everything in every organization is being reimagined by AI.
The new path to growth and advancement is rooted in your ability to tell a career story – where each job role is a chapter in a longer story that sets you up for the next step.
This is especially true for millennials and Gen Z who are replacing boomers and Gen X in the workforce. It’s also having a major impact on the role of managers. The best managers today are what I call “career dot-connectors”— meaning they help people on a team connect the dots between their current role and their future career opportunities. In the end, top performers should be able to write a best-selling story to make themselves irresistible candidates for the next opportunity.
Cassie: You’ve developed the Career Story Builder tool, and the very first question it asks is “What do you do better than anyone else in your field?” Talk about why that’s where we should start.
Ron: Every great story is told in three acts. In a career story, the first act is about establishing yourself – who you are and what makes you special. Best-selling career stories are based on someone’s strengths, the unique talents someone brings to the table.
The other two acts of your career story focus on differentiation and relevance, both of which are grounded in your strengths. You can’t differentiate yourself or stay relevant if you’re not playing to what you genuinely do better than others. And, it’s a lot easier to show up with confidence if you’re playing to your strengths.
The role of managers today is to make sure everyone on a team is in a job role aligned with their strengths. I have a favorite phrase as a manager: “Everyone has a source of greatness.” Great managers ensure their people are self-aware enough to know theirs. As managers, it’s important to recognize that sometimes people want to be better at something than they really are. That’s why I never liked it when people would say “I want to be more strategic.” I always saw that as an indicator they weren’t in touch with their true self.
Cassie: How do you develop that self-awareness? What if you genuinely don’t know what your greatest strengths are, or how to talk about them?
Ron: Former United Airlines CEO Oscar Munoz gave me the best advice on this. He calls knowing yourself “knowledge of contribution.” And he has a test that he says has proven 100-percent effective: ask your spouse or partner if feedback you’ve received at work is accurate.
It starts with feedback. Hearing candid feedback is the foundation of growth. Talk to people you work with and talk to your manager. In fact, ask anyone in your close orbit. The main goal is to get perspective on yourself. I always say the best people “fall in love” with their strengths and embrace them instead of trying to reshape them.
Managing your career requires self-awareness. It goes beyond career trajectory—it brings peace of mind as you approach your growth. I genuinely believe playing to your strengths will make you happier, more self-assured and confident, especially in job interviews. It’s easier to be an expert in something if you know it is true.
Cassie: For women specifically, I see a pattern where they downplay their strengths or focus on areas they want to improve rather than what they’re already great at. What’s your advice for women who struggle to claim their strengths confidently?
Ron: I would say knowing your strengths sets you free to be the best of yourself. It’s liberating to know you do something special when other people know it, too. It’s not bragging or shining a light on yourself. It’s just the truth.
I’d add that self-awareness plays a big role here. Knowing that you have weaknesses is as important as knowing your strengths. The best storytellers understand how to compartmentalize their weaknesses and focus on their greatness. There’s nothing inauthentic about this because everyone has things they aren’t good at. It also helps you frame areas to improve on your terms, if asked.
If you’re in a job transition or trying to advance your career, your job is to write a best-seller – to make you an irresistible candidate for the next opportunity. Confidence is the key to making your story better than others. Don’t focus on what you think you should be good at or what sounds impressive. Showing up believing in the best of yourself will make you, frankly, the more interesting candidate.
In the era of the corporate ladder, there was a bias toward being a generalist or general manager. Not so today. If you want to differentiate yourself in the Age of Uncertainty, focus on what makes you exceptional at things you’re naturally great at and build a career story around that.
Cassie: Let’s talk about how to put this into practice. Where should our members start?
Ron: I created the Career Story Builder specifically to guide people through this process. It’s a free, AI-powered tool that helps you craft a compelling career narrative starting with your strengths.
The tool walks you through a series of thought-provoking questions and gives you recommendations you can use immediately—in your LinkedIn summary, in interviews, in conversations about your career. One of my former Cisco colleagues, Ken Carrasco, used the tool and told me it was easy to use, quick to complete, and gave him a result he could use immediately without editing.
If you’re struggling to articulate your strengths or tell your career story with confidence, try the Career Story Builder. It’s free and unlimited, and I’d love to hear your feedback on how to make it better.
Cassie: Thanks, Ron, for showing us how to build our career stories from a foundation of strengths. Now women, when you answer “What do you do better than anyone else?” I’m giving you permission to channel your inner overconfident white guy. Don’t downplay, don’t hedge, just state your greatness. :-)
Ready to build your career story? Try Ron’s free Career Story Builder tool and discover how to articulate your strengths with confidence.
Try Career Story Builder
Recently I launched an AI-powered tool called “Career Story Builder” to provide a mentor, coach and buddy to help people write best-sellers about themselves — and why they’re ready for the next skills-based role.
Give the Career Story Builder a try. It’s free and unlimited. I’d also love to hear your feedback about how to make it better. It’s new and I’m sure it can be improved. Send me a DM with any thoughts.
In Summary: Principles of Managing in the Age of Uncertainty
I left Cisco to answer this question with research and evidence: What does the manager of the future look like? What are millennials and gen-z seeking in a manager? Which behaviors, tactics, skills or processes matter? What’s it going to take to attract and keep the best people over the next decade? In short, how to be a great manager.
Based on this research, the core philosophy of this newsletter is rooted in one idea: successful managers in this moment in time, for this generation of talent, need to be “career dot-connectors.” The next-gen doesn’t expect to spend their entire career on your team — that’s an idea boomers grew up with. A job on your team is like a chapter in a career story to the current generation. If you want the best people on your team, you have to connect the dots between roles on the team and the career opportunities of the people working on the team.
What is the“Age of Uncertainty”? If the industrial age was about taking predictable steps up the ladder, the age of uncertainty is about finding or discovering the path of a career without any predictable steps, without an obvious ladder — it’s why being a career dot-connector will differentiate you as a manager.
How to be a Great Manager in the Age of Uncertainty: Be a Career Dot Connector is available on Amazon.
What kind of manager are you? Take my free self-assessment and learn about yourself.