In today's fast-moving landscape, leaders face a recurring dilemma: stay the course or change direction. With markets evolving at an unprecedented pace and customer expectations continuously shifting, the ability to make timely, confident decisions has become a differentiator.
The art lies in knowing when to commit further — to double down — and when to pivot. Both paths carry risk. But delay or indecision often costs more than the wrong choice. What distinguishes effective leadership is not just clarity of vision, but responsiveness to real-world signals.
AI won’t make the decision for you. But it can sharpen your judgment — surfacing trends, detecting anomalies, and revealing opportunities or threats that may otherwise remain hidden until it's too late.
Defining the Strategic Fork
To double down means to deepen investment in a strategy, product, or market — allocating more capital, talent, and focus to accelerate traction. It signals conviction and bets on growth.
To pivot, by contrast, is to acknowledge that the current path may no longer serve its intended purpose. It involves changing direction — whether in customer focus, product design, business model, or go-to-market strategy.
Neither is inherently right or wrong. The danger lies in the gray zone: overcommitting to a faltering approach or hesitating too long to change. Indecision bleeds resources. Overcommitment locks you into diminishing returns. Discernment is key.
I’ve counseled hundreds of first time founders and CEOs and the truth is that you need a good criteria for both. What does doubling down mean and what does pivoting mean. To do this you need:
- A kill criteria that allows you to know when to pivot.
- A method for understanding when to double down. This usually comes back to companies that understand their value.
For instance at Loupe & Blade we believe in our speed as our super power. So if we can create solutions quickly, enter into tools and processes and opportunities that allow us to move quickly and at scale then it’s a win for us. However, in doing so we have to know when a business model or a method of action isn’t working. This means knowing what that looks like and when to cut bait. Not just for ourselves but for our clients themselves.
AI as a Decision Support Tool
Modern AI tools can offer unprecedented visibility into weak signals before they become strong problems — or opportunities.
These signals include:
- Customer behavior trends: drop-offs, friction points, conversion anomalies.
- Market sentiment: tone shifts in reviews, news, and social media.
- Operational patterns: inefficiencies, delays, or quality issues.
Where AI shines is in surfacing leading indicators — patterns humans may miss until they become obvious in lagging metrics like revenue or churn.
Example: An AI model analyzing user engagement and retention surfaces that new customers are disengaging after the first use. Traditional dashboards show growth, but AI spots a misalignment early — prompting a conversation: double down on acquisition or pivot toward solving activation?
As we here have embraced a lot more of our AI tools we’re using them to help us double down into research around our own data and figuring out what we don’t know. As perceptive as I think our agency is it’s surprising how much we need to learn.
Criteria for Doubling Down
There are moments when the right move is to lean in harder. AI can help identify those inflection points by revealing:
- Traction signals: increasing user engagement, repeat usage, word-of-mouth.
- Predictive demand: models showing rising interest or market need.
- Improving unit economics: lowering CAC, higher LTV, better margins.
Importantly, doubling down should align with core strengths and the long-term mission. AI insights are most powerful when paired with strategic alignment and internal conviction. Noise is everywhere — but signal clarity increases when indicators converge.
A pretty simple example: most of my early career was working with and for publishers. Many times I’d watch them chase topics that got them traffic but didn’t help them attract advertisers. Maybe they chased pop culture trends or Buzzfeed style articles that were good to bring engagement and traffic but were hard to turn into a product they could show advertisers to get dollars. At the end of the day doubling down on something that doesn’t serve your mission spins you in a lot of directions and ultimately wastes your time.
Criteria for Pivoting
On the other hand, persistent weak signals — even if subtle — deserve scrutiny. AI can detect:
- Stalled engagement: flatlining growth, shortening session times, rising churn.
- Market shifts: emerging competitor momentum, changing industry patterns.
- Negative sentiment: declines in public perception, investor skepticism.
When AI forecasts continued underperformance or mounting inefficiencies, it’s often a cue to reevaluate direction. Letting go can feel like failure, but ignoring poor signals out of sunk cost bias often leads to deeper losses.
The key is to pivot with purpose — not reactively, but with a new hypothesis backed by data and conviction. This is why kill criteria is important.
I counsel clients all the time when we’re doing paid ads: do yourself a favor and know how much you can spend and what kind of return you expect to help you know whether or not to keep going. If you hit those metrics and you cannot figure it out then you’re ready to shut it down.
Balancing Intuition and Intelligence
AI augments leadership, but does not replace it. Human judgment remains essential — particularly in ambiguous contexts.
Leaders must be aware of cognitive traps:
- Confirmation bias: seeking data that supports existing beliefs.
- Recency bias: over-weighting the latest events instead of long-term patterns.
It’s critical to create room for "red team" voices — internal dissent or alternate AI-driven scenarios that challenge groupthink. Diversity of thought, structured debate, and data triangulation make decisions more resilient.
This is so important because groupthink is one of the most difficult elements to overcome. Sometimes people go along because being the dissenting voice feels risky. Sometimes they go along with it because they are frankly exhausted by debate after a while. You need fresh eyes and a strong perspective. There are ways to do this without AI but depending on the size of the team or the dynamics it’s easier to do this with AI. At least to start.
Building an AI-Informed Decision Loop
Strategic decisions shouldn't rely on one-off analysis. They should be part of a continuous loop, where signals are monitored and assessed in real-time.
Key elements:
- Continuous data feeds: customer feedback, ops metrics, market signals.
- Regular review cadence: monthly or quarterly "pivot vs. persevere" reviews.
- Cross-functional input: product, finance, customer success — all must have a seat at the table.
Accountability is crucial. Who owns the decision? Who owns the signal interpretation? These roles need clarity to ensure action, not just insight.
In a world that rewards speed and punishes indecision, the ability to discern whether to double down or pivot is a core leadership skill.
AI offers clarity — not certainty. It’s a compass, not the captain. Leaders must still interpret the terrain, trust their instincts, and lead with both data and wisdom.
Final takeaway: Trust your informed instincts. Use AI not as a crutch, but as a catalyst. The best decisions are those made with clear eyes, steady hands, and the courage to choose.









