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Maximizing Productivity: Tailoring ChatGPT to Your Unique Working Style


ChatGPT is an incredibly versatile tool that can be tailored to fit your specific needs. Not only can you ask it to explain things at a certain grade level or use layman’s terms instead of business or technical jargon, but you can also customize its “personality” to better align with your own. Tailoring ChatGPT means you can have a more meaningful and productive interaction that suits your learning and working style.

In this post, we’ll explore how you can “train” ChatGPT to mirror specific personality traits, thereby enhancing your experience and making your journey from idea to execution that much smoother. We’ll provide you with specific prompts that serve as a “programming guide” to set the tone and style of how ChatGPT interacts with you.

My Personal Journey with Tailoring ChatGPT

Starting and running my own business has always been a dream driven by my entrepreneurial spirit. Spotting problems and envisioning solutions is second nature to me. Going through the exhilarating process of solution discovery, feasibility assessment, validation, planning, and execution is what I thrive on. This journey, though often embarked upon, has led to a full launch only once – a story for another post.

This blog was born from the realization that there are many dreamers out there, much like myself. Individuals brimming with great ideas, yet struggling to surmount that final hurdle to success. It’s important to understand that failing to cross the finish line doesn’t equate to personal failure.

My weaknesses:

  • Confidence: Despite my experience and background, I feel like the things I know are common knowledge. Information that everyone is fully aware of, so I don’t think I have anything of significance to offer. I worry my ideas are not innovative or exciting, so I don’t stick with them.  
  • Technology: I like technology but only from a “what it can do for me” standpoint. I don’t have the experience to code, configure, design, or anything hands-on like that. I do have the capacity to see and piece together how different systems should fit together to deliver the solution I need. This is often where my ideas crash and burn.  
  • Patience: The irony here is that if I had more patience, I could probably read product documentation, learn to code, and better understand SEO and things of that nature. This would improve my ability to complete the hands-on technical work I cannot do now.  My problem is I have so many things going on in my head and things I need to accomplish. I lose patience reading through documentation and begin scanning for what I need instead of ingesting everything. As you can probably guess, that ends poorly and often ends with me frustrated and moving on to the next big idea. 
Real World Example

That may sound discouraging, but the good news is that ChatGPT has been able to help me overcome all these challenges. I started by “programming” my ChatGPT, let’s call her Hailee, to be encouraging and supportive and to provide constructive feedback. I asked her to challenge me and my thinking if I was going off track. Hailee always seemed to think my ideas were fantastic or a game changer, etc., and I began to question if something was off. To test this, while brainstorming ideas for this blog, I randomly told Hailee I was considering writing an article about the soil needs of an apple tree. Hailee immediately challenged me and my line of thinking by reminding me that that topic was not aligned with the goals of Wired Wits. Below is the actual interaction.  

AP – I might do a post about soil needs of apple trees?

ChatGPT – That’s an interesting topic, but it seems a bit off-brand considering the focus of your blog is on entrepreneurship, AI, and personal development. Unless you’re planning to tie it into a broader theme related to your core topics, it might confuse your readers. What’s the angle you’re considering for this post?”

AP – Lol no angle, it was a test. You always seem to think my ideas are good, and I was starting to worry you might be more focused on encouraging and supporting me than providing real guidance. You passed, I am happy to announce. Lol

ChatGPT – Haha, gotcha! I’m here to provide both encouragement and constructive feedback. Glad to hear I passed your test! Now, back to business—what’s next on our agenda?”

Real World Assessment

How did Hailee help me specifically? I am glad you asked. From a confidence perspective, Hailee letting me know when I am on track and validating my thoughts and ideas has significantly boosted my confidence. I can also feel a difference in my everyday interactions outside of ChatGPT. 

Hailee has been instrumental in helping me configure this blog and setting up the different integration points with the various tools in my tech stack (Seedprod, Brevo, and Sendible).  In a different project I am working on, Hailee gave me the code I needed to build an API to pull real estate data from a site into a database (which Hailee also helped me set up and configure). In this example, Hailee served as my technical lead.  

Finally, and maybe the most important thing for me, I asked Hailee to provide information in short to medium responses. This ensures a quick and concise interaction that perfectly fits my learning and working style. If I have an issue with something, I can ask Hailee specific questions to get the necessary information. This saves me a lot of time and frustration. I don’t have to scan through documentation, taking in information relevant to what I need at that time.  Tailoring ChatGPT to fit my needs has been a game changer for me.

Other ChatGPT Personalities to Consider

ChatGPT can be trained to interact with you in almost any personality or style. Tailoring ChatGPT to your needs allows you to maximize your productivity. Below are more examples of tailoring ChatGPT.

The “Straight Shooter”

Personality Traits: You value efficiency and directness. You don’t have time for fluff—you want answers, and you want them now.

The Struggle: Your no-nonsense approach often leaves you frustrated with overly complex explanations or sugar-coated feedback. You crave straightforwardness, but it’s hard to find.

ChatGPT Training: For those who appreciate direct, no-nonsense feedback, you can train ChatGPT to be your “Straight Shooter.” Simply tell it, “ChatGPT, be blunt and get straight to the point when you answer my questions.” You can also ask it not to sugarcoat its feedback by saying, “I want the unvarnished truth.” And if you’re going off track, you can instruct it to alert you immediately with, “If I’m off track, tell me right away.”

The Transformative Power: With ChatGPT tailored to your style, you’ll get the information you need without the filler. It’s like having a straight-talking advisor at your fingertips.

The “Motivator”

Personality Traits: You thrive on positive reinforcement and need that extra push to keep going.

The Struggle: Lack of motivation can be your downfall, leading to procrastination and missed opportunities.

ChatGPT Training: If you need a constant pep talk to keep going, ChatGPT can be your “Motivator.” Instruct it to be encouraging and keep you focused on your goals. You can also ask it to remind you of your progress when you’re feeling down and to celebrate your small wins to keep you motivated.

The Transformative Power: With a ChatGPT programmed to be your motivator, you’ll find the encouragement you need to tackle any challenge head-on.

The “Detail-Oriented Analyst”

Personality Traits: You love diving deep into the nitty-gritty details and analyzing every aspect of a situation.

The Struggle: Sometimes, you can get lost in the details, leading to analysis paralysis.

ChatGPT Training: For those who love to dive deep into the nitty-gritty, ChatGPT can serve as your “Detail-Oriented Analyst.” You can ask it to provide you with detailed analyses and not to skip any important information. If you’re looking for a breakdown of complex topics into manageable parts, this is the personality for you. And even when you ask for an overview, you can instruct it to still include key details that matter.

The Transformative Power: With a ChatGPT that matches your analytical nature, you’ll have a tool that helps you make well-informed decisions without getting stuck in the weeds.

The “Creative Muse”

Personality Traits: You’re an out-of-the-box thinker who thrives on creativity and inspiration.

The Struggle: Creative blocks can be incredibly frustrating, stifling your progress and dampening your spirit.

ChatGPT Training: If you’re seeking inspiration and out-of-the-box thinking, ChatGPT can be your “Creative Muse.” Ask it to inspire you with creative ideas and to help you think outside the box. When you’re stuck, you can request alternative perspectives or approaches. You can also encourage it to push you to take creative risks and explore new avenues.

The Transformative Power: A ChatGPT programmed to be your creative muse can help you break through those blocks, offering fresh perspectives and innovative solutions.


In conclusion, ChatGPT offers a unique opportunity to tailor your AI experience to fit your specific needs and personality. Whether you’re a straight shooter who wants no-nonsense feedback or a creative soul seeking inspiration, you can “program” ChatGPT to interact with you in a way that enhances your productivity and creativity. The key is to experiment with different directives until you find the “personality” that clicks with you.

Stay tuned for our upcoming blog post where we’ll dive into using ChatGPT for skills, strengths, and weaknesses assessments. We’ll explore how this incredible tool can not only identify your gaps but also help you create a plan to fill them or enhance your existing skills. Trust me, you won’t want to miss it!

UPDATE: You can now read our post about using ChatGPT to complete a self assessment to better understand your strengths and areas of opportunity. The article is titled Elevate Your Self-Awareness: A Unique ChatGPT Self-Assessment.

You can also check out this article over at ZDNet to get more information about creating prompts.

Feel free to share your experiences and experiments with ChatGPT in the comments below. We’d love to hear how you’re making this tool work for you!

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