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🤖 why your AI prompt isn’t working

Subscribe here | Unsubscribe here | OG Tuesday May 27, 2025
A motivational quote on lined notebook paper reads,

✅ Today's Checklist: 
  • What AI prompting really comes down to
  • When "having it all" feels like losing yourself
  • PA desk break PSA you'll wish you heard sooner
🗓️ Free upcoming events: 🤔 Riddle me this: When is the top of a mountain similar to a savings account? (Find the answer on the bottom).

QUICK LINKS

 
👯‍♀️ Start a women's initiative and stop waiting for permission.
 
🪄 First drafts, but make it on-brand (and done in seconds).
 
⚖️ Managers, this one's for you: a 20-min crash course on what those new EO updates really mean.
 
⏳ One job offer on the table and waiting on another? Play it smart.

PRODUCTIVITY

 
 A robot holding a magnifying glass examines a rising arrow while a human with a tablet stands beside it, set in front of a digital search interface.
 

What AI Prompting Really Comes Down To


If you've ever typed a prompt into ChatGPT and thought, "Ugh, why is this so off?"

Let me gently say what I learned the hard way: It's not the bot. It's your prompt.

After spending two days in a deep-dive bot building workshop, I learned that most prompts aren't "wrong", they're just underdeveloped. Once you add the right layers, the quality of the output jumps way up.

Here's the 6-part formula that will change how you prompt forever (especially if you're building bots to do real work, not just party tricks):

1. 🧠 Identity: Give your AI a role to play

Start strong. Tell the model who it is. The clearer the identity, the more aligned the voice and behavior.

You are an elite productivity strategist who helps overwhelmed professionals organize their day with warmth, clarity, and systems thinking.

You can get playful or specific here:
  • A blunt-but-brilliant copywriter
  • A career mentor who channels BrenĂŠ Brown with a side of Mel Robbins
  • An emotionally intelligent team lead with Gen Z meme awareness
2. 🎯 Purpose: Define what it's here to accomplish

Be clear about the desired outcome.

Your job is to deliver daily planning prompts that energize the user, reduce overwhelm, and drive meaningful action without sounding robotic.

You can also include success metrics, what not to do, and whether the tone should persuade, coach, or simplify.

3. 🧩 Examples: Train it with your best work

AI learns from patterns. Feed it at least 7 to 10 strong examples. Use past emails, CTAs, intros, or frameworks. Don't just tell it. Show it.

4. 📚 Domain Knowledge: Give it the context it needs

Embed the tone, tools, and audience insight it should use.

You understand time-blocking, the Eisenhower Matrix, and the energy cycles of high-achieving professionals.

You know what keeps them stuck and how they like to be spoken to.

5. 🛠️ Modules: Teach it how to think, not just what to say

Walk it through processes or mental models.

Here's how to write a subject line: keep it short, use curiosity or benefit, avoid clickbait.

Other examples: how to reframe a limiting belief, write a soft CTA, or lead with a strong newsletter hook.

6. 🚫 Guidelines: Set rules and guardrails

Avoid overused phrases like "In today's world." Skip vague advice. Keep responses concise.

Define tone expectations like: warm but not fluffy, motivating but not pushy, clever but not cheesy.

✨ Additional Tips
  • Use ### to break sections (helps AI follow structure)
  • Build in a QA checklist like "Check tone, clarity, and CTA strength before responding"
  • Assign a persona for stronger tone and consistency
  • Ask how to improve the prompt (the AI will often help)
  • Keep one ask per prompt to avoid confusion
  • Tell it to slow down with "You get one shot. Think carefully."
  • Ask for its opinion with "What would make this clearer or stronger?"
Think of prompting as a system, not just a sentence.

When you structure it like a creative brief with voice, purpose, logic, and guardrails, you stop getting generic AI content and start getting real support.

Smart prompts = scary-good results. Play around and find out.

circle image of Joanna, Co-Founder of TA Joanna (TA Co-Founder)

MARKETING

 
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Marketing Like A Pro (Without Losing Your Mind)

 
We love a good shortcut—especially when it helps you look like you've got a whole marketing team… even when it's just you.

If you're DIY-ing your brand, business, or side hustle, these tools keep your digital game tight without the burnout.

🧠 Moz

SEO can feel like decoding a secret language. Moz hands you the translation guide. It helps you find the right keywords, fix what's slowing your site down, and see how you stack up against competitors. It's not magic—it just feels like it.

📅 Hootsuite

Still posting in real-time from your phone? Hootsuite lets you plan, schedule, and manage content across all your platforms in one sleek place. Bonus: you can sip that 4 pm matcha without worrying about forgetting your 5 pm post.

📬 GetResponse

This one's for the email girlies. Whether you're sending newsletters, launching products, or automating follow-ups like a boss, GetResponse makes it easy (and pretty). Email flows, landing pages, webinars? One tool. Zero panic.

✨ Together, these tools are your marketing cheat codes.

They save time, keep you consistent, and help you show up like a pro—without the all-nighters, guesswork, or spreadsheet-induced stress dreams.

BIGGEST CHALLENGE

 
A cartoon woman stands with arms out, looking torn between family on one side and work on the other, symbolizing the struggle to balance career and personal life.
 

When "Having It All" Feels Like Losing Yourself


A reader recently wrote to us:

"My biggest challenge is now being a mom. How do I juggle a career that used to be 80 hours a week with an infant?"

It's the kind of question that's less about time and more about identity. Because when your whole world shifts overnight, the challenge isn't just how to fit it all in—it's figuring out who you are now.

For so many, the return to work isn't just a logistical puzzle. It's a quiet, daily negotiation between two full-time roles. You're still ambitious, still capable, but now your drive is sharing space with something (and someone) entirely new.

This is the version of working parenthood that doesn't make it onto the company intranet. The one that happens between midnight feedings and morning meetings, in the push and pull between who you were and who you're becoming.

Here's what might help:

💡 Redefine what "doing it all" actually means

You used to thrive on 80-hour weeks. Now, if you get 80 uninterrupted minutes, it's a win. Trade volume for intention. Laura Vanderkam's "cave time" method is great for protecting small windows of deep focus.

🛠️ Systems = sanity

Parents on r/NewParents say it best: "Watching a baby is a full-time job. So is working. Doing both? Nearly impossible."

Create a shared family calendar (try Cozi) so you're not juggling logistics in your head. Automate where you can, template everything you repeat, and simplify your meals, meetings, and mornings.

👯‍♀️ Find your village (even virtually)

Isolation is ambition's worst enemy. These are real-deal resources worth checking out: 🧠 Just because you can doesn't mean you should

Someone asked career expert Alison Green if she could quietly care for her baby during the workday since she only works ~10 hours a week. Her job rarely notices—but her baby always does.

It's a tempting workaround, but as Alison puts it: "You can stop your baseboard-scrubbing […]. You can't pause a baby."

Even if your job is quiet now, it could shift overnight. And emotionally, splitting your attention might leave you feeling like you're short-changing everything (including yourself).

🧭 This is a season, not a step back

You're not less ambitious. You're just building a new model for success. It may not look like the one you had pre-baby, but it's no less valuable.

You're not falling behind. You're rebuilding. And that takes strength and strategy.

💬 Been here? Got a tip, tool, or mantra that got you through? Hit reply. We'd love to share your wisdom with other readers in an upcoming issue.

EMPLOYEE RECOGNITION

 
A group of four cartoon-style coworkers enthusiastically high-five each other, celebrating teamwork on a light purple background.
 

🎉 Your Team Deserves More Than a "Nice Job" in Slack

 
You're doing the best you can.

Team morale is...fine-ish. You shout people out in Slack when you remember. Maybe there's a quarterly gift card thing. You mean to do more, but the days fly by and recognition gets lost somewhere between "fire drill" and "Zoom fatigue."

Here's the thing: employees don't just want more recognition, they need it. Especially now.

And Nectar makes it effortless.

It's the recognition and rewards platform that helps teams build real culture—without the spreadsheets, clunky software, or forced "Yay team!" vibes.

💡 Imagine this:
  • A teammate finishes a big project → you send them a shoutout tied to a core value
  • Their manager adds points they can redeem for real rewards (gift cards, lunch, days off, you name it)
  • Another teammate joins in—then another. And suddenly? Culture starts compounding.
It's not just about celebrating the big wins. Nectar makes everyday appreciation part of your workflow, helping people feel seen, valued, and motivated—all inside tools you already use like Slack, Teams, or Gusto.

Recognition shouldn't be reserved for performance reviews or Employee of the Month. With Nectar, it's baked into your day-to-day—and it actually sticks.

SUBSCRIBER SPOTLIGHT

 

PSA: Step Away from Your Desk


"On my first full-time professional job, my boss said to be sure that I took my 30-minute break AWAY FROM MY DESK. Eat in the employee lunchroom and get to know folks from other parts of the organization, eat outside, or go for a short walk. Take the time. It really does improve your afternoon." 

— Ellen (Management Consultant)

⭐️ Share your best career advice here so we can feature it in a future newsletter.

STAFF PICKS


Stuff We're Loving This Week

 
☕️ Peak productivity without the crash: This coffee is designed for real, busy lives.

📬 Stay sharp without doomscrolling: The Hustle serves up biz + tech news you'll actually want to read.

🚀 Your shortcut to smoother, smarter onboarding.

🎙️ Even The Royals makes history fun, juicy, and totally bingeable.

JUST FOR FUN

 
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JOB LEADS


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Your Next Gig = One Click Away

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SPILL THE TEA


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