#421 – March 8, 2026

Making Your Next Move

Hello, fellow strategists! 

Strategy often comes down to making better judgments when the path ahead is unclear:  deciding when to persist and when to pivot, discerning which signals matter, and tweaking how everyday choices shape outcomes.

In this edition, we explore filters for deciding whether to stop or keep going, how a single anomaly may prompt a strategic shift, practical levers that reduce frontline churn, and using stories to sharpen communication. We also borrow a few decision-making lessons from the chessboard. It’s about judgment, connecting the dots, and making better moves. Enjoy!

 

Quick Takes

Knowing Whether to Pivot or Persist

Bringing a strategy to success often depends on grit. We’re frequently told that “winners never quit.” But blind persistence in an unwinnable situation can be just as dangerous as taking an off-ramp too early.

Nir Eyal take up this dilemma in How to Know If You Should Quit, Or If You’re One Step from a Breakthrough.

When we struggle, our minds naturally search for relief — not necessarily because the strategy is failing but because discomfort looks for an exit. The real challenge when strategy implementation stalls is to discern whether we face a plateau, where pushing hard will achieve a breakthrough, or a ceiling with a structural limit where more effort won’t move the needle.

Three filters can help clarify whether to stay the course or not:

• Set a Stop-or-Persist Decision Point in Advance:
  Our brains are experts at generating “rational” reasons for quitting the moment discomfort sets in. Counter this by deciding in advance when you will reassess the results of an initiative. Commit to reaching that next checkpoint regardless of how heavy the work feels. When the moment for assessment arrives, ask: “Knowing what I know now, would I start this again today?”
• Understand the Constraints Yet to be Overcome
  Some obstacles yield to persistence. Others don’t. You may have little influence over a legal or regulatory hurdle, a hyper-competitive market or an internal culture stuck on “the way we’ve always done it”. When the barrier is structural and outside your control, persistence doesn’t build a tunnel — it only digs a deeper hole. It may be time to pivot.
• Consider the Lessons When You Can’t See Results
  Progress can remain invisible during an incubation period, long before it produces a tangible outcome. If your efforts are still providing new information —about what works, what doesn’t, and what variables matter— you’re likely still moving forward. When the learning stops, the strategy may have as well.

We all face moments when we must choose whether to “hold or fold”. Don’t let exhaustion become the default for your most important decisions. Use these three filters to decide deliberately whether to persist or cut your losses.

 

Solving the Frontline Churn Puzzle

High turnover among frontline staff quietly drains organizations, forcing managers into a constant cycle of hiring, onboarding, and retraining while service quality slips.

Research on the retail sector reported in Harvard Business Review suggests the problem often isn’t pay or purpose alone. More often, it’s the everyday mechanics of work —especially scheduling and management practices— that determine whether people stay or leave.

To stabilize your workforce, consider these four levers:

• Predictable Schedules: Workers stay longer when shifts are posted earlier, change less often, and avoid punishing patterns (such as retail shifts that require closing late and opening early).
• Managerial Flexibility: Retention improves when supervisors can accommodate reasonable requests for shift swaps, time-off approvals, or adjustments for childcare and commuting realities.
• Perceived Fairness: Employees judge their schedules against those of their peers. When preferences are ignored and scheduling feels arbitrary, last-minute or unevenly distributed, a sense of being treated unfairly pushes people out the door faster than workload alone.
• Site-specific Drivers: One-size-fits-all policies often miss the mark. The same practice may work at one site but fail at another depending on commute times, labour supply, or competition from other employers.

Frontline churn isn’t just an HR problem. It’s an operational design problem where these data-based levers can replace guesswork.

 

The Potential Powers of a Single Data Point

We are taught to distrust “anecdotal evidence” and wait for a statistically significant sample before drawing conclusions. Usually, this is wise. But in strategic foresight, waiting on data collection can mean missing a window of opportunity.

As Spencer Greenberg notes on Clearer Thinking, there are specific conditions where a single data point isn’t an outlier — it’s a revelation. Think of a single observation not as a trend, but as a key. Sometimes, one data point is all you need to:

• Prove the Possible: A single black swan disproves the theory that all swans are white. One verified “impossible” event (like Roentgen discovering X-rays) immediately expands the boundaries of your perspective.
• Reveal the Mechanism: You don’t need to take apart a thousand clocks to understand how a gear works. One deep look at a “causal” example may allow you to build a mental model you can apply elsewhere.
• Find the Signal in the Noise: Sometimes, one new fact acts like a secret code, making a mountain of previously confusing or “noisy” data suddenly snap into a clear, coherent pattern.
• Shift the Strategy: If an outcome is nearly impossible under your current context but highly likely under a different one, a single occurrence may provide enough evidence to warrant an immediate pivot in focus.

In your work, don’t just count the data; listen to what a single, well-vetted anomaly might be trying to tell you. Excellence is found in knowing when to wait for the graph, and when to act on the spark.

 

8020Info Drill-Down:

Use Stories to Engage Wandering Minds

Although all human beings are storytellers, we can struggle to make our presentations compelling for audiences prone to boredom and wandering attention. In a recent AI Business Lab newsletter, Michael Hyatt shared a step-by-step framework with nine storytelling tips to make your message more engaging:

• Start with Your Audience, Not Your Story:  Before you choose a story, ask what your audience needs most right now. Shape your story around their challenges, their values, and the outcome you want to inspire.
• Establish a Clear Goal:  Every story needs a point, and that point should be clear to you before you start telling it. Hyatt suggests asking yourself: What do I want people to think, feel, or do after hearing this?
• Create Tension Through Conflict:  Your audience needs to feel that something is at stake — a problem to solve, an obstacle to overcome, a tension to resolve.
• Raise the Stakes:  The greater the tension, the more compelling the story. A missed deadline, a failed product launch, a team on the verge of quitting — name the stakes out loud.
• Show Vulnerability:  Nothing builds trust faster than honesty about your own failures and struggles. When your story lets people see your imperfections, they stop seeing you as a speaker and start seeing you as an authentic human being.
• Use Cause and Effect:  Strong stories show how one thing leads to another, how every decision triggers a consequence. Every consequence should set up the next scene.
• Apply the Power of Surprise:  The brain pays attention to the unexpected. If your story unfolds exactly as predicted, people tune out. A well-placed twist (already foreshadowed in the story) will jolt them back to attention and makes the story more memorable.  But use surprise deliberately.
• Use Sensory Details:  Facts inform the mind. Sensory details transport your audience into the scene. To use Hyatt’s example, don’t just say it was a difficult meeting — describe the silence in the room, the look on someone’s face, the way the air felt before someone spoke.
• Deliver a Satisfying Resolution:  Your audience has invested emotional energy in your story. They deserve an ending that ties it together.

You can find potential stories close at hand from your own experience, whether it’s a relationship that fell apart, a hiring decision you got wrong or a strategy that didn’t work.  Use them to make your presentations and speaking engagements more compelling.

 

For Your Reading List:
Lessons Beyond the Chessboard

Chess players excel at considering multiple options, allowing them to seize an opportunity, idea, or move that others miss. Two-time US chess champion Jennifer Shahade calls this “thinking sideways”, the title of her new book, Thinking Sideways: How to Think Like a Chess Player, coming out in April.

Her widely applicable advice includes a warning to avoid over-calculating when it relies on too many assumptions about how others will behave. Thinking too far ahead may also distract you from a great move right in front of you. And she reminds us you can play a perfect game and still lose, so focus on the quality of your decisions, not the outcomes. My favourite: When you first see a good move, take a moment to look for a better one before you act.

(If you enjoy podcasts, The Economist recently featured an engaging interview with Shahade on how chess thinking sharpens everyday judgment.)

 

Closing Thought:
It Won’t Make Sense Til Later

“You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future.”
— Steve Jobs  (Stanford University 2005 commencement address)