Month 3: Pilot

Run a series of pilots—small, low-risk experiments to test your new direction. Pilots help gather real-time data and feedback, allowing you to adjust incrementally as you go, instead of relying on blind leaps.


Week 1

Get Scrappy. During my time at Google we loved “being scrappy.” We knew the conditions or output of our work would not be perfect, but it was important to release anyway, to “launch and iterate.” Just get something out, then test it, get feedback, revise, and do it over again.

Holding a mindset of launch and iterate encouraged us to get minimum viable products out to the company then have our peers test the programs, letting their feedback guide future versions. Getting a program out, even a scrappy, imperfect, 70-percent version, was better than waiting for 100-percent perfection. That ideal state may never happen, and by that point users’ needs would likely have shifted.

Discussion prompts:

  • What small experiments can you run?

  • What real-world data can you collect?

  • What's one next step you can take?

Suggested template for post-call homework:

  • Pilot Risk Map — Evaluation Spreadsheet: Full of ideas but not sure which one to pursue next? This spreadsheet will help you map opportunities across four categories, ranging from high risk, high reward to low risk, low reward.
  • 30-Day Decision Tracker: Without the proper perspective on a situation, it’s all-too-easy to get mired in the weeds of emotion, hope, future worry and past regret. Choose one area you’d like more clarity on and rate how you feel about it each day. This template will certainly encourage you to take a more objective stance on a big question you’re grappling with and see how you feel over time, not just in the heat of the moment.

Week 2

Pause, Review, Repeat. Just like the TV pilot, a career pilot is an experiment that is meant to be evaluated, and quickly. Drop your attachment to the outcome and stay curious: What can I learn here? How might this inform my next move? How can I expand my original vision?

Once you have completed a pilot, or even several concurrently, the next step is to evaluate what worked and what didn’t. What would you do differently? What has potential for greater opportunity? After that, you will identify another round of experiments and repeat the Pilot process.

Piloting is not a one-and-done proposition. It is likely that you will run several pilots until you figure out what sticks. What smaller bets might you want to expand upon? Each time you go through this process, you will learn about yourself and refine ideas about who you want to work with and what you want to work on.

Discussion prompts:

  • What worked?

  • What didn't?

  • What could you do differently?

  • Run through the Pivot process on your pilot: what can you double-down on next time? What new resources might you need to scan for, whether people, skills or projects?

Suggested template for post-call homework:

  • Decision-Making Template: Weighing a big decision? Pro/con list not doing the trick? This template will help you break down fears/concerns and brainstorm next steps to move you forward.

  • Bottleneck Buster Template: You might feel a vague sense of where you’re operating inefficiently, but if you already knew exactly what was clogging up the works, you probably would have fixed it by now! As with many habit changes, awareness is the first step. This template will help you pinpoint bottlenecks and brainstorm ways to improve your systems.

Week 3

Transitioning to Launch. While piloting involves a series of continual, small experiments that provide information about your next move, the Launch stage is when you make the big decision that completes your pivot. These decisions do not have a guaranteed successful outcome, though you will have reduced risk throughout the Pilot stage.

Your group will likely be at different stages of a pivot at this point—some still piloting, some recalibrating, and others ready to launch. Take this week to lightly discuss the transition from pilot to launch. 

Discussion prompts:

  • When will you make your big move?

  • What are your linchpin decision criteria?

Suggested template for post-call homework:

  • Launch Timing Criteria Checklist: You have reduced risk by cycling through the first three stage of the Pivot Method (Plant, Scan, Pilot), but how do you know when it is time to go all in? This template, excerpted from the book, will help you identify and prioritize your most important launch criteria.

Quarterly Review. That's a wrap! Time to check-in with your mastermind crew, celebrate how far you've come, and set goals for the following quarter.

Discussion prompts:

  • What have you accomplished this quarter?

  • Beyond the accomplishments themselves, what are you most proud of?

  • What were your biggest challenges? How did you overcome them?

  • Your new Guiding Principles: mindsets / mantras / approaches to life?

  • What are one or two key focus areas for next quarter

  • What additional systems/support do you want to build for yourself moving forward?

Suggested template for post-call homework:

Week 4