Managing in the Age of Uncertainty
Why strategic planning is the "new black" in the age of AI
By now we all know the future of any team will be part human, part agent — and that's just the beginning of a never-ending cycle of evolution in the way work gets done.
It is literally the opposite of the corporate ladder that boomers experienced — where everything was so predictable. It was easy to plan in the boomer era; a time of incremental growth and incremental change.
Managers today are faced with planning for the present and future at the same time: on the one hand, evolve the team as agent technology gets better; on the other hand, operate and run a team to get results.
In my last job at Cisco in sales operations, my team never missed a quarter — spending nearly a $100 million of Cisco’s money every fiscal year delivering more than 2 million product demonstrations for it.
I was lucky at the time to have a right-hand person named Mimi deGrandpre as my business partner. I was used to a financial analyst as a partner, but Mimi taught me about planning — because I couldn’t miss a quarter or all hell would break loose.
I recently reached out to Mimi — because she’s still teaching teams to plan.
I wanted to get her thoughts on managing today, and how managers can navigate — by planning better — the age of AI.
WHY: The Numbers Tell You Everything You Need to Know
I spent the last year interviewing a lot of people for this newsletter. In each interview, I don’t really have a position about what I’m trying to write about. It sort of reveals itself by the wisdom of the person I’m listening to.
That’s what happened when I sat down with Mimi.
I wanted to talk to her about all the change happening inside of organizations today — and specifically what first-time and early-career managers are supposed to do about it. How do you plan when everything is moving? How do you lead a team when the rules keep changing?
Mimi opened with three numbers that I think every manager needs to tape to their laptop about the “quality” of planning today:
20. The percentage of all projects so badly misaligned to strategy they should never be done at all.
40. How much better proactive prioritization outperforms “fair” allocation of capital, according to McKinsey’s research over 15 years.
60. The percentage of strategic goals that are actually successfully delivered.
Those are awful numbers. On some level, it must reflect the lack of training and development managers get — which is why I called Mimi.
WHAT: The 4M Method
Mimi said something in our conversation that I haven’t been able to stop thinking about:
“Without a strong vision and purpose of some kind, you’re always going to struggle. Your team is going to struggle to understand what they’re marching toward and what their reason for getting up in the morning is.”
This deeply resonates with my experience as a manager. When so much in the present is changing, a compelling vision of the future keeps the team believing in the work it’s doing. I learned this from John Chambers when he was CEO of Cisco. As I recently told my friend Ash Seddeek, John would tell me, “Belief is worth 1-3 points of growth.”
Mimi uses a framework she calls the “4M Method.” As readers of this newsletter know, I’m frustrated by the lack of training first-time managers get for the job. That’s why I love frameworks that solve specific problems. So managers, here’s your “planning in a box” - the 4M’s:
Mission. Use your organization’s mission, purpose, and vision as the filter. If an initiative doesn’t tie directly to your purpose or your long-term vision, it shouldn’t make the cut. Ask yourself: does this move us closer to our core purpose? If the answer is no, it might be interesting — but it’s not strategic.
Money. Strategy without financial context is just wishful thinking. Every project or idea must connect to one of three things: generating revenue, saving costs, or laying the groundwork for future financial gain — investment in people, process, or tools. Think of this as the business case lens for every strategic decision.
RoadMAP. When everything is a priority, nothing is. Stack-rank every initiative, without emotion. Your roadmap should reflect the mix of foundational work that keeps the lights on, growth work that builds the future, and transformational projects that disrupt the status quo. Lay them out across an 18-month timeline. Move from reacting to planning. Prioritization isn’t about saying no forever — it’s about saying “not yet.”
Measure. This is where most plans fall apart. Metrics are often too vague or disconnected from what the team actually controls. SMART metrics force you to be clear. What exactly will success look like? How will you know you’re making progress?
“Metrics aren't just for reporting — they're for motivation, clarity, and alignment,” Mimi emphasizes. “When your whole team understands what success looks like, they're more likely to achieve it.”
HOW: Start Here This Week
Before you build a plan, Mimi says you need to know if your approach to prioritization is or isn’t working.
Here are her “five signs” you have a prioritization problem:
There’s no list of projects and no criteria to assess them
There are resource allocation issues — overload or burnout
There are frequent changes in direction
Everything is considered a priority
There are “side” or “pet” projects
If you recognize yourself in any of those, here’s Mimi’s five-step process to fix it:
Step 1. List ALL projects, no matter the size or budget.
Step 2. Choose five criteria to assess all projects against — strategic alignment, customer impact, ROI, resource availability, risk.
Step 3. Stack-rank the projects using the criteria.
Step 4. Assign resources — financial and human — to ensure success.
Step 5. Say “no” or “not yet” to anything that falls below the budget line.
Process is one of the Six Drivers of Consistency
What Mimi is describing with the 4M Method is exactly what I mean by consistent process — one of the Six Drivers of Consistency I identified in my research with millennials and gen-z.
The best people know every manager has their own operating model. The team can only follow your lead if you share your process. Take a hard look at Mimi’s 4M Method and learn from it.
SEE WHERE YOU STAND
How consistent are you? Take the Self-assessment.
ManagerMentor • All Rights Reserved • The Culture Platform, Inc. • 2026
This is an absolutely fantastic installment, Ron. I'll be sharing on LinkedIn, have emailed it to several, and will implement this planning framework for myself (personally and professionally). Thank you!