The
Trenches.
For managers battling skepticism, politics, and inertia. Your strategy is worthless if you can't execute.
The Execution Gap
Every organization has a beautiful strategy deck. Most of them will fail in the trenches. The problem isn't vision—it's the gap between what leadership announces and what actually gets done.
This gap is where careers are made or broken. This is where you operate.
"Culture eats strategy for breakfast."
— Attributed to Peter Drucker
Your AI initiative will die in the immune response of organizational culture unless you know how to navigate it.
Before you can build the future, you must bury the past. Every organization is haunted by Zombie Projects—initiatives that consume resources but deliver nothing. They exist because nobody has the courage to kill them.
Me-Too Syndrome
Started because a competitor did it. No unique value proposition. Running on imitation, not innovation.
The Metrics Ghost
Can't define success. No clear KPIs. "We'll know it when we see it" is the actual strategy.
Silo Seclusion
One department's pet project. No stakeholder buy-in. Will die the moment its sponsor leaves.
The Art of the Safe-to-Fail Experiment
You don't need permission to transform everything. You need permission to try something small. Here's how to design experiments that generate learning without career-ending risk.
1. Define the Hypothesis
Not "Let's try AI" but "If we use AI to classify support tickets, we can reduce response time by 30% within 30 days." Specific. Measurable. Time-bound.
2. Minimize Blast Radius
Run the experiment in one team, one region, one product line. If it fails, it fails small. If it succeeds, you have proof.
3. Set Kill Criteria
Define in advance what failure looks like. "If we don't see X by date Y, we stop." This isn't pessimism—it's discipline.
4. Document Everything
A failed experiment with documented learnings is an asset. A failed experiment with no documentation is just a waste.
The 30-Day AI Experiment Template
- Problem: What specific pain point are we addressing?
- Hypothesis: If we [action], then [result] because [reason].
- Success Metric: How will we measure improvement?
- Kill Criteria: What would make us stop?
- Budget: Under $50K. Under 30 days. One team.
- Learning Goal: What do we learn even if it fails?
Psychological Safety or Nothing
Google's Project Aristotle found that psychological safety was the #1 predictor of team performance. If people are afraid to fail, they won't experiment. If they won't experiment, you won't transform.
Signs Your Team is Afraid
- × Nobody challenges ideas in meetings (they save it for the hallway)
- × Failures are hidden or rebranded as "learning opportunities" after the fact
- × Everyone waits for the boss to speak first
- × "That's not my job" is a common response
How to Build It
- ✓ Publicly celebrate failed experiments that generated learning
- ✓ Share your own failures and what you learned from them
- ✓ Ask "What did we learn?" before "Why did this happen?"
- ✓ Create "pre-mortems" before projects start: What could go wrong?
The Resistance Map
Every transformation has enemies. Know them. Name them. Navigate them.
The Skeptic
"We tried this before and it failed."
Counter: "What's different this time? Here's what we've learned..."
The Protector
"This will destroy jobs / my team / our culture."
Counter: "Let's involve you in designing the transition. What would make this work for your team?"
The Perfectionist
"We need more data / analysis / planning."
Counter: "What's the minimum we need to run a 30-day experiment? Let's learn by doing."
The Politician
Publicly supportive, privately undermining.
Counter: "I need your specific commitment by [date]. What can I count on you for?"
The Two-Pizza Rule
Keep transformation teams small enough to feed with two pizzas. Smaller teams move faster, communicate better, and have clearer ownership.
The 15% Rule
Allocate 15% of team time to experimentation—no approval required. This creates a protected space for innovation within existing structures.
Demo, Don't Debate
A working prototype wins more arguments than a slide deck. Build something ugly that works. Show it. Iterate based on feedback.
Your First 90 Days
Whether you're new to the role or just starting a transformation, here's how to build momentum without burning out.
Days 1-30
Listen & Map
- • Interview 20 people across the organization
- • Find the hidden influencers (not just the titles)
- • Map the zombie projects
- • Identify one quick win that proves you can deliver
Days 31-60
Win Small
- • Deliver the quick win publicly
- • Start one safe-to-fail AI experiment
- • Kill or pause one zombie project
- • Build your coalition of the willing
Days 61-90
Scale the Win
- • Share experiment results (success or failure)
- • Propose the next three experiments
- • Request resources based on evidence
- • Start building the factory, not just the pilot
Master the Execution Game
These frameworks come from years of frontline transformation work. Go deeper with Alan Brown's books.