Ever downplay your success to sheer luck? Or feel intimidated by the opportunities in front of you? Maybe you’re considering turning them down or opting out, convinced they’re expecting a version of you that doesn’t really exist. You’re not alone. Many entrepreneurs are held back by imposter syndrome.
Jade Bonacolta leads a marketing team at Google, and is an award-winning creator in the productivity niche. In 7 months, she grew her LinkedIn audience from 1k to 180k followers, and launched a brand called The Quiet Rich, with a newsletter that is rapidly growing at 3-4k subscribers every week. As a result of her growth, she has become a respected executive coach, enabling startup founders, CEOs, authors, and aspiring creators to grow their brands and businesses. She frequently advises on how they can leverage artificial intelligence. Within her roles, Bonacolta is often the odd-one-out, as well as the youngest by several years. She has frequently overcome imposter syndrome and helped her clients do the same.
“Imposter syndrome affects nearly everyone, regardless of how successful they are. It’s because of The Dunning-Kruger effect, a mental model that says the more expertise you build in a field, the more aware you are of what you don’t know or haven’t yet achieved,” explained Bonacolta. “Paradoxically, experts might underestimate their abilities more than novices do.” AI tools (such as ChatGPT, Bard or Claude) can be used as a valuable personal AI mentor with your best interests at heart.
Prove to yourself that you deserve to be in any room and silence those nagging doubts. Train ChatGPT to become your highly-capable executive coach with these 7 prompts.
How to use ChatGPT to overcome imposter syndrome
Get good at self-promotion
Ever been tasked with selling yourself, only to struggle with putting words on the page? Clients, investors and event attendees want to know about you, so an “about me” section of proposals, pitches or presentations is crucial. But, explained Bonacolta, “we’re so accustomed to downplaying our achievements or fixating on failures, that it often feels like bragging to write this yourself.” Here’s where an outsider’s perspective is valuable, to summarize your credentials without making you blush. Paste her prompt into your LLM of choice and share your unique value proposition with the world.
“Review my resumé and the product/service I offer. Give me 6 compelling reasons why I’m the best option that my target audience of [explain your target audience] could choose. Craft a short pitch explaining my unique value proposition, specifically what sets me apart from my competitors. My resumé is [insert your experience] and my offer is [insert product, service or business description]. My target audience is [insert demographics, firmographics] with the following pain points [insert challenges.]”
Become a better negotiator
If you struggle with self-doubt, you might be holding back from making audacious requests. Instead, you’re believing you’re not as good as you are and accepting the first offer you hear. One of Bonacolta’s favorite business quotes is “You don’t get what you deserve. You get what you negotiate.” She said that, “without a predetermined plan for negotiation, fueled by self-worth, it’s easy to discount your value and lose the upper hand to a more practiced negotiator, even if you objectively have more leverage.” Avoid that happening with this exact prompt.
“I’m negotiating with [describe the other party, for example a client] on [insert topic or proposal] where I want the outcome to be [describe your dream outcome]. Generate a list of 10 questions I should ask in order for me to better understand their non-negotiables. Then make a list of the possible BATNAs (best alternatives to a non-agreement) that I should consider. And finally, help me decide [key decision you want to make, for example your walkaway price].”
Speak better in public
First impressions matter, and you don’t have long to make a good one. “The opening 15 seconds of a presentation or pitch is when your audience will make 90% of their assessment of you,” said Bonacolta. “The best public speakers begin with compelling stories that build both connection and establish credibility, setting the stage to win the room with anything they say next.” Especially if you’re not quite sure how you ended up on the stage, leverage AI to cement your position with a strong opening line.
“Review my experience and background from my resumé. Write a compelling, 2-minute founder story that immediately grips the audience’s attention. [Copy and paste your resumé along with any interesting information about your founder story and audience].”
Address uncomfortable conversations
Imposter syndrome is not conducive to having difficult conversations. You’ll often put them off, leaving problems to escalate. “The best entrepreneurs don’t avoid uncomfortable conversations such as giving tough feedback, letting a client go, or firing a team member,” explained Bonacolta. “AI tools are surprisingly effective in this context. Use them to provide you with exact scripts, timing, and best practices to address the problem.” She recommends this prompt to deal with those conversations before it’s irreversible.
“I need to deliver feedback to [person’s name and their relationship to you] about [nature of the feedback including details]. Provide me with a specific script to share that feedback and inform this person that it’s coming. My goal is to [desired outcome, for example make them feel safe and understood], while clearly communicating my boundaries and expectations. Draft 10 questions [person’s name] will likely ask in response to my feedback and suggest how I should respond to each one.”
Say no with conviction
If you don’t believe your success is deserved, you’ll accept invitations below your potential. You’ll keep yourself playing small by saying yes to things your professional capabilities have outgrown. Bonacolta suggested that, “as your business grows, you should say no to better and better opportunities.” She explained, “if you say yes to every decent opportunity that comes your way, you’ll quickly burn out. The most successful entrepreneurs make “no” their default. They decline most opportunities, but they do it in an elegant way that earns them respect.” Make the no easy with this prompt.
“The following five opportunities have come up, but I can only say yes to one of them. [List the opportunities]. Help me prioritize which one to accept based on my goal of [describe your one business goal]. Then write four extremely elegant notes to decline the other opportunities. The decline emails should be respectful and preserve those relationships for the future.”
Network like a pro
“It’s common to feel imposter syndrome when you’re in a room with your hero or someone whose work you admire,” said Bonacolta. But fangirling shouldn’t be your vibe. Rather than being too shy to initiate conversation, or giving gushing praise that positions you below them, become their equal by being genuinely interested. “Prepare an arsenal of good questions based on recent news articles and interviews” said Bonacolta. Even if you don’t know the guestlist, she suggests you “keep a list of go-to questions that can spark an interesting conversation with anyone.” Use this prompt to get your starters.
“I’m about to meet [outline person and their role] who is [describe their position or interests] and I want to build rapport. Generate a list of 15 unique questions tailored to that person that will help me stand out and demonstrate my curiosity in their work.”
Build mental toughness
“The best way to overcome self-doubt is to keep a stack of evidence of the challenging things you’ve accomplished,” explained Bonacolta, who knows mental toughness and resilience is key for every founder. Bonacolta’s method for building this is to regularly attempt a misogi: “an epic challenge, in which your chance of failure must be 50%, without being fatally dangerous.” Once you complete a misogi, which might be “running a marathon with a 20kg pack, staying in a cold plunge for six minutes, or climbing Mount Kilimanjaro,” you will know for sure that you are capable of hard things. You can apply this mindset to your business success to overcome your imposter syndrome. Try this prompt for ideas of your challenge.
“Give me 10 ideas for a misogi that I could attempt within the next two weeks in the following location [insert the location of your challenge], for example [include misogi examples appropriate for you]. Then create a rational plan of how I can complete that misogi.”
Overcome imposter syndrome and grow your business
Don’t let imposter syndrome hold you back. Level up your game and believe you belong in any room. Get good at self promotion and negotiation, open your talks with complete confidence, and say no to opportunities below your potential. Equip yourself to hold tough conversations, network with your role models and set goals that others think are impossible.
Use these 7 prompts to overcome imposter syndrome for the benefit of your life and business. Remember that even the most accomplished people in your field have experienced self-doubt. If you haven’t, it likely means that you haven’t pushed yourself hard enough to reach your potential. Step out of your shadow self and into the spotlight.
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