Managing in the Age of Uncertainty

What Great Managers Do When They Don't Have All the Answers

This much we know about managing today: we don’t know what we don’t know.

How do you manage a team of people with so much uncertainty? I write this newsletter to try to be helpful to managers in this moment in time, especially as a new generation of millennial and gen-z managers come on board with AI literally reimagining work.

But I’m keenly aware that I don’t know what I don’t know, and so I’ve decided to create a “guest expert” series to expand the knowledge and learnings for the readers of Managing in the Age of Uncertainty.

In this issue of this newsletter, my guest expert is friend and former Cisco colleague Leslie Rubin. She’s spent the past 25 years advising senior executives on communication strategies. She’s also the author of Filling the Leadership Gap, and a former communication advisor directly to John Chambers when he was CEO at Cisco.

Why “Filling the Gap” Matters

As I wrote last week, communication is one of the top skills necessary to be a great manager in this era — especially as teams develop into hybrid “biological” and “digital” people. The pace of change seems to be accelerating; it’s virtually impossible to know what’s next in the evolution of how a team executes.

To borrow Leslie’s idea, I know managers are being challenged right now to “fill the gap” with specific answers to all the questions they’re being asked about the future — which is exactly why I contacted Leslie to see what I could learn from her and share it with readers of this newsletter.

“Ambiguity kills team trust,” Leslie says in the first 30 seconds of our discussion.

Amen is all I can think.

I ask Leslie what she means. “Dig deep, be thoughtful,” she tells me. “What do my people need in this era of change? What words do I use?”

Now she had me at “hello.”

My research into the future of managing found that millennials and gen-z look for managers who are consistent, including six specific drivers of consistency. It makes sense when you think about it: the more uncertain things are, the more people value the certainty of consistency.

One of the six drivers of consistency is being authentic to yourself and sharing your mindset as a manager.

It’s squarely on this point of how to share “your thinking” that brought me to Leslie. How do successful leaders and managers express their mindset to teams? How can managers bring more clarity about the future when you don’t know all the answers?

What Great Managers do to fill the gap between ambiguity and certainty

“You can give your team purpose by sharing your thought processes and help them anticipate future direction,” Leslie shares.

She says successful leaders focus on three specific areas to “fill the gap” between what we know and what we don’t know — all anchored in how you think.

Each of these three areas helps your people know what kind of manager you’ll be as the world transitions to the future.

1. Own your point of view: what do you believe in?

2. Reflect on your values: what do you stand for?

3. Understand how you handle pressure says a lot about how you think: what are you going to be like inside the pressure cooker when it hits?

Manager Homework

“Choose your words intentionally,” Leslie advises. I agree. When you look at each of these three areas, it’s easy to go off-script — which only exacerbates the confusion.

Here are some practical tips for today’s managers:

1. Own Your Point of View: What Do You Believe In?

Great managers don’t wait for certainty before sharing where they stand. They tell their team things like: “Here’s what I believe is happening, and here’s why I think it matters for us.”

Practically, this means:

• Sharing your interpretation of ambiguous situations, not just forwarding the company memo

• Being willing to say “I think this change is actually good for us, and here’s my reasoning” — even when others are complaining

• Distinguishing between what’s decided (facts) and what’s your read on the situation (your POV) — your team needs to know which is which

Remember: Waiting for perfect information leaves a vacuum — and vacuums get filled by rumors and worse.

2. Reflect on Your Values: What Do You Stand For?

Your values are your anchor when the situation is shifting beneath your feet. But they only work if your team knows what they are — not from a poster on the wall, but from watching you make decisions.

Practically, this means:

• Being explicit when a decision you made was driven by a value (”I chose to protect the team’s time here because I believe focus matters more than optics”)

• Acknowledging when circumstances pushed against your values and how you navigated it

• Returning to the same 2-3 principles consistently, so your team can start to predict how you’ll behave — that predictability is what trust is built on

3. Understand How You Handle Pressure: What Are You Like in the Pressure Cooker?

This is the one most managers underestimate. Your team is watching you — carefully — the moment things get hard. How you show up in those moments tells them everything about what it’s safe to do, say, and feel.

As John Chambers told both Leslie and me: “You learn the most about people when they’re under pressure.”

Practically, this means:

• Naming your stress before it leaks out sideways (”I want you to know this deadline has me under pressure — I’m going to work hard not to pass that stress onto you”)

• Having a self-awareness practice — journaling, a trusted colleague, a coach — so you know your patterns before they catch you off guard

• Debriefing after pressure moments: “How did I show up last week? What do I want to do differently?”

In the end, your team doesn't need you to have all the answers. They need to know who you are. At its essence, that is Leslie’s call to action. Get to work managers.

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.