Managing in the Age of Uncertainty
Meet Jan De Kesel, Master of Time
“Everyone is drowning in things to do.”
And yet, Jan De Kesel tells me that most managers are leaving more than 30 percent of their day on the table.
Jan is my first new professional contact on Substack, whose algorithm suggested Jan’s newsletter Thinking Time to me; and then I read “Killing To-Do Lists is Possible.” I’ve been a subscriber since and wanted to interview him to see what today’s managers could learn about the most precious commodity of all: time.
I write about the differences in managing boomers from millennials and gen-z. I’ve managed in both generations, and as I point out in this newsletter, there are many fundamental differences. For millennials and gen-z, the biggest change is the end of the corporate ladder as an obvious career path. For managers of millennials and gen-z — the people I write for — it is empirically true that managers today have far more time demands on them than boomer managers — with far less support.
Look at direct reports as one measure of “more to do”: the average manager of millennials and gen-z has three times — that’s 300% — more direct reports than boomer managers. It’s no wonder that the next gen are taking charge of their careers themselves and not counting on the corporate ladder. Managers don’t have enough time for anyone except perhaps their top 10 percent.
When Time Matters Most: Problem-Solving
I’m eager to learn and share the secrets of getting 30% of my time back with readers of Managing in the Age of Uncertainty — for all the obvious productivity and psychological benefits.
So I ask Jan how, but he’s thoughtful, and he starts by telling me something so interesting: “I’ve always been about the next thing before I finish the last thing.”
I realize Jan is starting with a universal truth of managing: how we spend our time problem-solving determines our success. But Jan wants readers of this newsletter to know that different time horizons have different problems to solve; each needs a different approach to how we spend our time.
“Productivity is a side benefit,” Jan points out. It’s remarkably simple advice to managers. If you want to save time, focus on how you spend your time solving problems. But it starts with this question, according to Jan: Are you solving for the present or solving for the future?
Deeper Thinking: What You Need to Know
For problems in the present, Jan suggests what he calls “deeper” thinking: what do I need to know to excel at my current job? Digging deeper into your current role is the idea. It makes so much sense to focus problem-solving within the context of your current goals and what you are accountable for.
I remember running Cisco’s pre-sales demo engineering team when the concept of deep thinking helped me understand how to successfully manage the team amidst budget cuts. Looking back, I wasn’t really thinking about the future; it was right then, right there, that lead me to to the answer. In Cisco’s era of efficiency, I came to understand that unit cost was what I needed to focus on in order to successfully manage the team. Cost-per-demo and driving it down became the secret to my team’s success.
I was a unit cost guru in my final five years at Cisco — and I know it saved me a lot of time. But far more importantly, it saved my team, which is the whole point of what Jan is saying. The productivity is a “side benefit.”
Focus on what you need to know for today is the key takeaway of deeper thinking.
When you think about your current role as a manager, how would you answer this question: what do I need to know to do my current job better, right now? Don’t assume you know the answer. Get some perspective. Ask your trusted advisors to give you a straight answer. Ask your business partners the same question.
Wider Thinking: What You Need to Learn
On the other hand, Jan encourages “wider” thinking when considering the future: what do I need to learn to prepare for the future? “When you are bridging from the past to the future, look outside your own industry,” is how Jan describes “wider” thinking.
I saw this lesson first-hand when Cisco brought someone in from the outside to lead our supply chain team. When I worked for former Cisco CEO John Chambers, I would help him organize the company’s ops meetings. So I was sitting in the room when Angel Mendez, Cisco’s new SVP for supply chain, told us we were measuring our success in supply chain as company the wrong way.
Instead of measuring ourselves against the networking industry, Angel said we should be measuring ourselves against best-in-class companies, like Walmart. When compared to Walmart’s metrics, Cisco’s supply chain had a long way to go. Welcome to the wider view.
Try dipping your toes into “wider” thinking.
As a manager, you are surely dealing with change and possible impacts to your team or business. AI is lurking somewhere. Try to find a way once a month or quarterly to reach outside your current business context. Consciously seek out learnings from someone you don’t know working in an adjacent industry or an industry that you know is doing things better than your own.
“You can get more than 30 percent of your time back,” Jan concludes and smiles at me.
It makes me think if I need wider or deeper thinking in my business right now. I know what my brain is telling me. Do you know? (I gotta go deeper.)
One More Suggestion from Jan: Take a Walk Outside
Beyond its health benefits, Jan says this about walking outside: “You can’t take notes while you are walking.” It’s a chance to absorb, re-listen or re-think.
Wow. I’m heading outside right now. I hope you will too.
Manager Thought of the Week — A Challenge
“I don’t know what I don’t know.”
I don’t know who actually said this, but I love what it says about humbleness as a manager. Take the “I don’t know what I don’t know” challenge: commit to saying it over the next week or month to your team and see how your teammates react and what you don’t know. Your team likely has many subject matter experts or functional experts — people who can help you go deep or wide when you are problem-solving. When your teammates hear you say, “I don’t know what I don’t know,” it implicitly shines a light on your people; pride in themselves and their commitment to you as their manager will only grow.
Know a Champion for Manager Excellence?
If your company has a “champion for manager excellence” (like Stefani Okamoto of ServiceNow) ! I’d love to meet and interview them.
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.


Great topic Ron and clearly managing time is key to business success at any level. Here’s another discovery about managing time as it relates to productivity. In my 32 years at the helm of Speakeasy working with thousands of executives annually from some of the most respected companies in the world, including as you know, Cisco, this is what I hear repeatedly. Most internal meeting led by managers are an absolute total waste of time! Why? Because the messages they communicate are the wrong messages and not relevant to job execution. Why? Because most managers are out of touch with the execution itself, what motivates execution, and most of all, the efficiency of successful execution that comes from optimal time management and communicating effectively. Here’s a perfect example, one of Speakeasy’s large global enterprise clients did an internal time audit and discovered across multiple positions that 20% of time was being spent on creating PowerPoint slides for internal meetings of which 80% of those slides had no value to successful execution. Essentially, a total waste of time. Instant solution, they issued a policy that slides could not be used for internal meetings. Instead, motivational communication was employed with meaningful conversations. The result, that 20% of time used on deck production was invested in client outcomes that significantly impacted revenue. Time optimization executed! Amen!
Thanks for the great conversation Ron. I am happy to read that we are very much on the same page when discussing these subjects. It's very interesting to see that big corporate and entrepreneurs can learn from each other. I will add this to my "wider" thinking.