The Power of Self-Awareness and Effective Communication: Lessons from D'Arcy Coolican and ChatGPT

Gina Martinez

Gina Martinez

Dec 11, 20234 min read


The Power of Self-Awareness and Effective Communication: Lessons from D'Arcy Coolican and ChatGPT


In the realm of business and artificial intelligence, self-awareness and effective communication play pivotal roles in achieving success. Whether it's navigating through fundraising challenges or interacting with AI models like ChatGPT, understanding the importance of these two factors can help us overcome obstacles and unlock our full potential. In this article, we will explore the insights shared by D'Arcy Coolican on self-awareness in fundraising and delve into the prompt strategies that can lead to better output when engaging with ChatGPT.

Self-Awareness in Fundraising:

When faced with skepticism and the statement, "I've seen this before, it didn't work," cultivating self-awareness becomes crucial. D'Arcy Coolican emphasizes the need to be super self-aware in such situations. By weaving a compelling narrative that connects all the pieces, we can address doubts effectively. This requires a deep understanding of our strengths, weaknesses, and past experiences, allowing us to present a well-packaged story that wins over potential investors. Superhuman self-awareness becomes a tool to manage skepticism and turn it into an opportunity for growth.

Effective Communication with ChatGPT:

Interacting with AI models like ChatGPT offers immense possibilities, but it also requires a thoughtful approach. While there is no right or wrong way to engage with the AI, there are certain strategies that can enhance the quality of output. To make the most out of ChatGPT, it is essential to formulate the right prompts. Here are ten prompt strategies that can lead to better output:

  • 1. Be Clear and Specific: Clearly define the purpose of your interaction and provide specific instructions to ChatGPT. This helps the AI understand your intentions and generate more accurate responses.
  • 2. Use Contextual Information: Incorporate relevant context in your prompts to guide ChatGPT's responses. By providing background information, you enable the AI to generate more contextually appropriate and meaningful answers.
  • 3. Experiment with Formatting: Explore different formatting styles, such as bullet points or numbered lists, to structure your prompts effectively. This can help ChatGPT comprehend the desired output format and generate responses accordingly.
  • 4. Ask for Multiple Perspectives: Encourage ChatGPT to consider different viewpoints by asking questions like, "What are the pros and cons of X?" This prompts the AI to think critically and provide a comprehensive analysis.
  • 5. Seek Clarification: If you receive an ambiguous or incomplete response, don't hesitate to ask ChatGPT for clarification. This helps in refining the AI's understanding and generates more accurate and relevant answers.
  • 6. Provide Examples: When seeking creative suggestions or solutions from ChatGPT, offer examples or scenarios to guide its thinking process. This allows the AI to generate more imaginative and tailored responses.
  • 7. Incorporate Constraints: If you have specific limitations or constraints, communicate them clearly to ChatGPT. By setting boundaries, you can ensure that the AI generates responses within the desired parameters.
  • 8. Iterate and Refine: ChatGPT may not always provide perfect responses initially. Iterate and refine your prompts based on the AI's previous outputs to achieve better results. Experimentation and learning from previous interactions are key to improving the quality of output.
  • 9. Utilize System Messages: Pay attention to system messages provided by ChatGPT. These messages offer insights into how the AI is interpreting your prompts and can help you adjust your approach accordingly.
  • 10. Provide Feedback: When ChatGPT generates responses, offer feedback on the quality and relevance of the output. This helps in training the AI model and improving its future performance.

Actionable Advice:

  • 1. Cultivate Self-Awareness: Whether in fundraising or any other endeavor, developing self-awareness is crucial. Reflect on your strengths, weaknesses, and past experiences to craft a compelling narrative that addresses doubts and wins over stakeholders.
  • 2. Master the Art of Prompting: When interacting with AI models like ChatGPT, prioritize the formulation of prompts. Experiment with different strategies to enhance the quality of output, such as being clear and specific, using contextual information, and seeking multiple perspectives.
  • 3. Embrace Iteration and Feedback: Continuous improvement is key when engaging with AI models. Iterate, refine, and provide feedback to enhance the AI's performance and achieve better results in subsequent interactions.


Self-awareness and effective communication are essential elements in various spheres of life, from fundraising to engaging with AI models like ChatGPT. By understanding the insights shared by D'Arcy Coolican and implementing the prompt strategies discussed, we can navigate challenges more effectively, unlock our full potential, and achieve success in our endeavors. Embrace self-awareness, master the art of prompting, and embrace iteration and feedback to harness the power of these two vital factors.


  1. "For when someone says “I’ve seen this before, it didn’t work” — D'Arcy Coolican", (Glasp)
  2. "ChatGPT Guide: 10 prompt strategies for better output", (Glasp)

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