Moonshot Method

Let your assistant fail. Wait — what?

No, you shouldn’t go around looking for opportunities for them to do a bad job. But you should give them opportunities to own big projects that they’re unlikely to nail.

For example, if you have a board meeting coming up, ask them to put together the v1 deck.

The goal isn’t a polished deck you can run your meeting with the first time around. Instead, moonshot assignments like this will:

1. Demonstrate Excellence → They will see the difference between their work and your final version, and what improves in each iteration.
2. Push Boundaries → Challenging tasks help expand their skill set faster.
3. Motivate → Trusting them with important work shows them you believe in their potential.

When you trust your assistant with challenging tasks, you’re not just offloading work — you’re creating opportunities for growth. As your assistant develops new skills, they become capable of handling more complex responsibilities, which increases your capacity.

Here's how to implement this method:

1. Identify a high-leverage task: Choose something you usually handle yourself because of its importance or complexity. This could be preparing a board deck, drafting an investor update, or creating a strategic plan for a new initiative.
2. Briefly explain the task: Provide a high-level overview of what you need, but resist the urge to give step-by-step instructions. The goal is to see how your assistant approaches a complex challenge.
3. Let them attempt it with minimal guidance: This is the hard part. You need to step back and let your assistant work independently, even if you know they'll struggle.
4. Review their work and provide detailed feedback: Don’t point out mistakes — seek to understand their thought process and help them see the task from your perspective.
5. Guide them through multiple iterations: Each round should bring their output closer to what you need. Be patient – the learning that happens during this process is irreplaceable.

Let's see this in action with a board deck preparation example:

Round 1 (Set Expectations)

• Context: "We need to prepare our quarterly board deck. This is a critical communication tool that showcases our progress, challenges, and strategic direction to our investors."
• Task: "Please prepare the deck using last quarter's as a reference. Here's an example of an A+ board deck from a similar company in our industry. Note how it tells a compelling story about their growth trajectory."
• Expectations: "The deck should include updated metrics, a narrative of our quarterly performance, and insights into our key challenges and opportunities."
• Assistant's output: They update the numbers and create a basic slide deck, but it lacks the strategic depth and narrative flow of the example provided.
• Your feedback: "Great start on updating the numbers. Let's elevate this further. The example deck we looked at excelled in three areas: 1) It highlighted critical metrics with context, 2) It told a compelling story about the company's progress and challenges, and 3) It anticipated and addressed potential board member questions. Let's focus on incorporating these elements in our next iteration."

Round 2 (Show A+ Examples)

• Context: "Our board is particularly interested in our growth initiatives this quarter. We need to showcase how these align with our overall strategy."
• Task: "Revise the deck, focusing on our key growth initiatives and main challenges this quarter. Here's a voice memo explaining what the previous deck lacked and how we can improve it."
• Expectations: "The deck should now include more strategic content, impactful data visualizations, and a clear narrative linking our initiatives to our long-term goals."
• Assistant's output: They add more strategic content and attempt to create a narrative, but the presentation of data could be more impactful, and some key insights are missing.
• Your feedback: "I appreciate the added strategic content. To take this to the next level, let's focus on data visualization. Here are some examples of how top consulting firms present complex data. Notice how they use color, layout, and design to make key points stand out. Also, consider how we can connect our various initiatives to tell a coherent story about where the company is headed."

Round 3 (Live Feedback)

• Context: "The board has requested more information on our long-term product strategy and its financial implications. This is our chance to showcase our vision and get their buy-in."
• Task: "Finalize the deck, including a section on our 18-month product roadmap and its impact on our financial projections. Here's an example of how a unicorn startup in our space presented their product roadmap to their board."
• Expectations: "The final deck should have a strong narrative, impactful data visualization, and a roadmap section that clearly links to our overall strategy and financial goals."
• Assistant's output: They produce a much-improved deck with a strong narrative and good data visualization. The roadmap section is solid but could be more tightly linked to the company's overall strategy.
• Your feedback: "This deck is really coming together nicely. To make it truly outstanding, let's consider how the product roadmap ties into our long-term vision. Think about how we can present our ambitious plans while setting realistic expectations. The goal is to use this deck to guide a strategic conversation with the board about where we're headed and how we'll get there."

Commit to seeing the process through at least a few rounds of iteration, no matter how tempting it might be to take over yourself.

As you and your assistant work through these processes, you'll develop a shared language and understanding that makes delegation more efficient and effective over time.