The Hardest Leadership Decision: Knowing When to Pivot in Business & Product Marketing
Most leaders fail not due to a lack of effort, but because they don’t know when to stop. This guide will help you master the art of pivoting, make data-driven decisions, and avoid the sunk cost trap.
Three years ago, a product manager I knew sat in a high-stakes product review meeting. The company had poured millions into a groundbreaking , expecting it to dominate the market.
The launch? A disaster.
Sales weren’t just low; they were nonexistent.
The thin line between commitment and waste
The room was tense. The leadership team debated: Should we keep pushing forward? Should we tweak our messaging? Or should we cut our losses and move on?
Then, the CEO asked the hardest question:
“Are we still investing because we believe in this, or because we’re afraid to admit we were wrong?”
Silence.
He remembered the tension in the room when leadership finally made the call: They scrapped the project. It felt like admitting failure but in hindsight, it was the smartest decision they ever made.
Have you ever been in a situation where you kept investing in something that wasn’t working, hoping it would turn around?
That was the moment I realized knowing when to stop is as important as knowing when to start.
If you've ever struggled to walk away from a failing strategy, product, or campaign, this article is for you.
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Why this matters more than you think
As product marketing and business leaders, we take pride in our work. We invest not just money, but time, effort, and reputation into what we build.
But here’s the uncomfortable truth:
Not every investment is meant to succeed.
Yet, we often refuse to pivot because:
We’ve already financially invested too much (sunk cost fallacy).
We fear admitting failure will damage our credibility.
We assume more effort = better results, even when the market says otherwise.
We’re emotionally invested and convince ourselves we’re “almost there,” even if there’s no data to back it up.
Sound familiar?
We’ve seen multi-million-dollar companies go bankrupt because they refused to change course. We’ve also seen scrappy startups become industry leaders because they pivoted at the right time.
So how do you know when to push forward and when to pivot?
The art of knowing when to pivot
A. Defining the Problem: Are You in a "Dip" or a Dead End?
Seth Godin, in The Dip, makes a critical distinction:
A Dip is a temporary setback on the way to success. (Think Amazon struggling in its early days.)
A Dead End is when no amount of effort will change the outcome. (Think Kodak ignoring digital photography.)
How to tell the difference:
Are you improving? Even small, consistent growth means you're in a Dip. If every metric is stagnant or declining despite effort, you’re in a Dead End.
Is the market still interested? If customers are disengaged, disinterested, or actively avoiding your product, you might be heading for a Dead End. (Competing Against Luck, Clayton Christensen)
Is the problem execution or strategy? If tweaking the strategy improves results, it's a Dip. If nothing works, you might need a bigger shift. (The Lean Startup, Eric Ries)
B. The Emotional Struggle: Why Pivoting Feels Like Failure
Mr.X, a product marketing manager, launched a big-budget campaign for his company's new product. It flopped.
The response?
Double down. More ads, more outreach, bigger discounts.
Still, nothing changed.
The biggest fear? Admitting the strategy wasn’t working.
Mr.X felt like changing course would make him look incompetent.
This is the emotional weight of pivoting:
It feels like betraying the work your team has done.
It feels like wasting resources instead of recovering them.
It feels like a personal failure, even when it’s just a strategic shift.
But here’s what Mr.X didn’t realize yet:
Great leaders pivot not because they’re failing, but because they’re focused on winning.
(Thinking in Bets, Annie Duke)
C. The Transformation: When Smart Companies Choose to Pivot
Mr.X finally took a step back.
Instead of forcing a failing strategy, he analyzed why customers weren’t engaging.
He found the positioning was off, customers didn’t understand the product’s real value. (Obviously Awesome, April Dunford)
He tested new messaging, focusing on customer needs, not features.
He reallocated the marketing budget to channels that showed real engagement. (Hacking Growth, Sean Ellis)
Within six months, engagement skyrocketed, sales picked up, and they hit their targets.
What changed? He shifted from desperation mode (“we have to make this work”) to strategy mode (“let’s find what actually works”).
This is the power of pivoting.
How to Assess Whether to Pivot or Persist: Practical Steps
If you're facing a major strategic decision, use this four-step framework from Inspired: How to Create Products Customers Love:
1. Evaluate Customer Feedback
Are your customers getting real value from your product or service?
Is there a mismatch between what you offer and what customers need?
2. Measure Performance Against Key Metrics
Are conversion rates, retention, and engagement improving?
Are acquisition costs sustainable?
3. Assess Market Trends
Are competitors outpacing you in innovation or adoption?
Has market demand shifted?
4. Consider Opportunity Cost
Could those resources be better spent elsewhere?
Is the current investment blocking better strategic moves?
If the data suggests misalignment, it’s time to pivot.
If not, refinement and persistence might be the right approach.
What About You?
If you’re reading this, chances are you’re facing a tough decision right now.
Maybe it’s a marketing strategy that isn’t delivering.
Maybe it’s a product that isn’t gaining traction.
Maybe it’s a business model that worked before—but the market has changed.
What’s your next move?
Are you in a Dip, or a Dead End?
Drop a comment—I’d love to hear your story. Let’s figure it out together.
The Courage to Walk Away
Netflix abandoned DVD rentals and pivoted to streaming. Now they lead an entire industry. (Blue Ocean Strategy)
Slack was a gaming company that pivoted into workplace messaging. Now it’s worth billions. (The Lean Product Playbook)
Adobe ditched boxed software and moved to the cloud. Now it dominates the market.
What do these companies have in common?
Data-driven decision-making: leaders recognized the shift through user behavior and market trends.
No emotional attachment: They let go of old business models despite previous investments.
Clear customer understanding: They used insights from Jobs-to-be-Done (Competing Against Luck) to offer a better product fit.
Above all, “They knew when to let go.”
How to Know When It’s Time to Pivot: The 3-Step Framework
When faced with a tough decision, ask these three questions:
1. Are You Getting Meaningful Signals from the Market?
YES? Keep refining.
NO? You might be forcing something that isn’t there.
Check real data, not assumptions. (Competing Against Luck)
2. Is the Problem Fixable with a Tactical Adjustment?
YES? Try small, iterative improvements.
NO? A bigger strategic shift may be needed.
If small tweaks don’t work, stop burning resources. (The Lean Startup)
3. Are You Holding On Because of Pride or Fear?
YES? Time to step back and reassess.
NO? Keep pushing forward.
Pivoting isn’t failure, it’s a leadership skill. (The Dip)
Final Thought:
One of the hardest decisions leaders face is knowing when to walk away.
Yet, the most successful companies are those that embrace change as a strategy, not a failure.
Great product marketers know when their positioning isn’t working (Obviously Awesome).
Great business leaders recognize when the market has moved (Blue Ocean Strategy).
Great strategic marketers measure results and adapt accordingly (Hacking Growth).
Not every investment leads to success, but every investment should lead to learning.
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