As I have shared, one of the most intriguing parts of my job is interviewing leaders to gain their insights into the key issues they are embracing and wrestling with in their real-world environments so
that I can build them award-winning business simulations that enable organizations to learn by doing.
For example, I recently interviewed 30 leaders from around the world across a range of functions to gather their insights into better, more practical coaching best practices so I can build a portfolio of Praction AI role-playing exercises.
As I reviewed the customized summary of my interviews and an analysis of what I heard with our clients, one of them asked me a provocative question, “Did you get any insights or the sense that our message of creating and coaching to a much more aggressive, proactive, breakthrough innovation culture is getting through?”
I answered transparently that I did not, and shared that maybe I wasn’t asking the right questions, to which they assured me I was, since they had helped me write the questions and approved them.
We then had a deep discussion about the takeaway learnings from the interviews, which were all very traditional, like “I need to spend more time preparing for coaching conversations.”
I was then given the directive to make the simulation experience compel leaders to coach differently. “Now is the time for bold leaders to move fast and break things,” was the mantra, and my job is to build a simulation that creates the environment and coaching environment to do that. And obviously, AI is the catalyst behind this.
However, this is a content area that seems relatively new because of the AI aspect that is simply changing everything and integrating it into the approach. I decided to come up with a list of the five things leaders must do to coach toward a culture of move fast and break things:
1. Redefine What “Good” Looks Like (Speed + Learning, Not Perfection)
Most leaders are still coaching to an outdated definition of success: thorough, polished, low-risk execution.
That doesn’t work anymore.
In a “move fast and break things” environment, good decisions are not perfect decisions; they are fast, informed, and reversible decisions. Coaching needs to shift from “Did you get it right?” to “How quickly did you learn?”
If your coaching still rewards perfection over progress, you are quietly killing innovation.
2. Coach to Decision Velocity, Not Just Decision Quality
Business acumen has always emphasized making good decisions. Now it must emphasize making timely decisions.
In an AI-enabled world, the cost of waiting is often greater than the cost of being wrong.
Great coaches now ask:
- “What decision can you make today with 70% confidence?”
- “What happens if you wait another week?”
- “What is the cost of inaction?”
You are no longer just building smart leaders. You are building decisive leaders under pressure.
3. Normalize Intelligent Failure (and Make It Visible)
Every organization says they are okay with failure.
Very few actually are.
If leaders are going to “break things,” they need to know the difference between:
- Careless mistakes (unacceptable)
- Intelligent experiments (required)
Coaching must explicitly separate the two.
Even more importantly, leaders must publicly reinforce intelligent failure, not just tolerate it quietly. If failure feels safe only in hindsight, your culture will default to risk avoidance.
4. Shift Coaching from “Answers” to “Experiment Design”
Traditional coaching sounds like this:
- “Here’s what I would do.”
- “Let me give you the answer.”
That model collapses in a fast-moving environment.
Modern coaching sounds like this:
- “What are the 2–3 experiments you could run this week?”
- “What would success or failure look like?”
- “How quickly can you test and learn?”
You are no longer coaching for the right answer. You are coaching for the right learning loop.
5. Align Incentives with Speed, Not Just Outcomes
Here is where most organizations fail.
They talk about speed, innovation, and bold thinking…
But they still reward:
- Hitting the number
- Avoiding mistakes
- Delivering predictable outcomes
That is a direct contradiction.
If you want leaders to move fast and break things, then your coaching—and your performance systems—must reward:
- Speed of execution
- Volume of intelligent experiments
- Learning velocity
- Cross-functional action
Otherwise, your leaders will smile, nod, and continue playing it safe.
Things to Think About
“Move fast and break things” is easy to say and incredibly difficult to operationalize.
Because at its core, this is not an innovation initiative, it is a coaching transformation.
You are asking leaders to:
- Let go of control
- Embrace ambiguity
- Reward speed over certainty
- And redefine what success looks like in real time
That doesn’t happen through an email. It happens one coaching conversation at a time.
And if you get that right, you don’t just build faster organizations, you build organizations that learn faster than the competition, which in today’s world may be the only advantage that actually lasts.
