Diane Unravels AI

Diane Sadowski-Joseph is the co-founder of ApplyAI and has been in leadership, learning, and organizational development for 20 years. Her repertoire of roles includes time at LifeLabs Learning, Pearson, Sailthru, and many more!?

In her current role as co-founder, Diane helps people enhance human and organizational performance through strategic AI integration. Her mission is to empower humans to thrive with AI. Diane is also a parent of two who loves spicy food and taking a pun too far. Diane and I met about 10 years ago through the wonderful world of tech startups!

About Diane

Name: Diane Sadowski-Joseph

Pronouns: She/Her

Occupation: Co-Founder and Head of Product

Industry: Organizational Development and AI?

Location: San Francisco Bay Area

AI Tools:?

• Large Language Models – ChatGPT(which I call ChattyG, Claude, and Perplexity, Fathom note taker, Notion, Canva AI features, Dall-E - (the kooky wildcard)

How would you rate your AI knowledge?

I’d rate myself a 7.5. Over the past year, I've immersed myself in learning AI—experimenting with it at work, interviewing super-users, and studying AI strategy at UC Berkeley. I try to stay on the cutting edge while focusing on creating value for organizations today. There’s always more to learn, so I’ll likely stay at a 7.5 for a while.

What sparked your interest in AI??

Initially AI scared me. Living in the Bay Area, I was surrounded by billboards and heard much talk of AI replacing jobs. I also saw people I admired getting excited about it. I wanted to decide for myself, so I tried ChatGPT and immediately saw its potential to change the workplace. That flipped the switch from fear to curiosity.?

What are you most excited about when it comes to AI?

I’m excited about AI’s potential to enhance strategic decision-making and efficiency for people in organizations. AI helps humans streamline workloads, reduce cognitive load, and boost performance without sacrificing quality. With the constant pressure to do more with less, AI feels like a critical tool to help people thrive. Personally, it saves me 20 hours or so a week and lightens my own cognitive load so that I can be a better, more strategic leader.

Diane's 24 Hours With AI

MORNING:

Help at home: How I show up at work starts at home, so I use AI to save time there. This morning, I asked ChattyG for help packing my son’s lunch. One habit I’ve developed is problem precision—the clearer you are about the problem, the more useful AI is.

• Prompt: I have 5 minutes and need to pack a cold lunch for my kindergarten child. I have these five things in the fridge. It needs to be nut-free and quick to eat. If other ingredients are needed, just ask.
• Result: A mashed edamame, string cheese, and tahini wrap. My son loved it.

Meeting efficiency: I had a meeting with my ApplyAI co-founder to discuss product strategy with Fathom Notetaker enabled. Mid-meeting, it alerts us? when we start “monologuing,” which helps us regulate turn-taking. After the meeting, it summarized key points and created action items that I quickly copied into our Notion Dashboard. Soon, I'll integrate Fathom to upload to Notion automatically.

Product interview preparation: For a product interview with a board member, I ran an experiment where I used Claude to pre-generate responses and had us talk through them. This let us dive deeper into details faster. Note: I don’t recommend this method all the time since it can create bias, but it was a great way to change up the conversation with someone I know well.

• Prompt: You are <NAME>, an experienced founder and current CEO of X company. Answer questions about product-market fit for a company focused on strategic AI training. Use this LinkedIn profile, these podcasts/articles, and these meeting transcripts to draft your responses.?
• Result: We got into details faster, explored some ideas they loved hadn’t thought of.?

AFTERNOON:

Content brainstorming and feedback: I used AI to outline a workshop on how executives can boost performance with AI. I’ve found AI is a great thought partner to accelerate creation and integrate perspectives I may not have immediate access to between human feedback cycles. Using ChatGPT and Canva, I can build something high quality in about half the time it used to take, which gives me more time to gather real human input. Bonus: since AI is not actually human, you don’t have emotions to navigate when you don't take its suggestions.?

• Prompt: Since this task used a variety of very task-specific prompts, instead here are two habits that have leveled up my prompt engineering game:
• I always specify who I need it to be, e.g., “a leader in a rapidly growing ed-tech startup struggling to scale their culture” or “an AI researcher and DEIB expert from outside the US.”
• I end each prompt with “Please optimize this prompt by asking me questions.” This encourages me to think through missing details and strengthens my strategic thinking and delegation muscles by reminding me of all of the components that go into each ask.

Relationship building: I use AI to edit follow-up emails and texts. My go-to prompt is: “My reader is X, the goal of the email is Y; make what I wrote shorter and more useful to them.” I also use Dall-E to create custom images related to conversations. For example, after a client joked about stand-ups on a stand-up paddle board, I created an image of it. It provided a shared moment of delight.

Data analysis and strategy: As a small leadership team, we are always trying to make data-driven decisions faster. Today we used it to analyze sector data and market research we'd gathered so we could make a decision about strategy. We used ChatGPT live during the meeting as well as for further analysis. However, we never let AI make strategic decisions alone; the best results come from combining AI with expert judgment. I’d estimate this approach has made us 50% faster both in efficiency of conversations and time saved by avoiding wrong turns.

• Pro-tip: Share the ChatGPT analysis including the prompt thread in advance of the meeting so people can read through both your thoughts and how you got there. You can also go back and edit prompts in a thread and re-run them for collaborators to build on each other’s work.
• Prompt: You’re an expert with 30 years of experience helping startups find product-market fit in the services, leadership, and consulting sectors. Help the head of product at a company enhance capabilities through AI. Create a table with target sectors using the criteria below, include two suggestions not in the data with rationale, and provide a bulleted prioritization list. Tell me what I haven’t thought of that I should, including different perspectives. Please ask me questions to optimize my prompt.?

EVENING:?

Expert in your pocket. I listened to a podcast and wished I could ask the guests my own questions so I created a quick GPT. It wasn’t perfect, but it was much more fun than Googling and reading through a million articles. How I did it:

• Download public transcripts of the podcast. Copy/paste into a single document. Upload that doc to ChatGPT.
• My Prompt: You have the knowledge of all the experts in this podcast. Use these transcripts and anything else these authors have written on this or related topics to answer my questions.
• Start asking questions! Again, ask it to ask you questions to optimize your prompts if you don’t feel like thinking through all the details at first.?

Coordinate volunteer sign up. Helped my partner create a sign-up sheet for parent volunteers from a printed handout of the dates and tasks the teacher gave him.?

• Prompt: Please create a sign-up sheet you can copy and paste into Google Docs that includes Date, Day, Time, Activity, Number of Volunteers needed, and five blank columns for volunteers. Please populate this table with the dates and activities listed on the attached photo and add a row for every Friday between Sept 3rd, 2024 and May 29, 2025 with the activity “help with Friday folder”. Then please draft a short, friendly email encouraging parents to volunteer.?
• Result: An email including an editable signup sheet for volunteer opportunity for the whole school year in 5 minutes.?

Avoiding screens. I try to avoid screens before bed, but sometimes my mind is still full of ideas. I wrote a bunch of product thoughts on the back of a drawing my son gave me (sorry) and took a picture. I’ll upload the image to ChatGPT in the morning and convert it into editable text.?

Looking ahead, I’m excited about a future where AI is seamlessly integrated into organizational cultures, enhancing both efficiency and human potential. I’m excited to guide leaders in navigating this journey, ensuring AI adoption is thoughtful, strategic, and impactful.

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I'm Amanda Halle , author of Unraveling AI. You can call me Amanda, Mands, or AJ (my middle name is Jane). I've been in and around the HR/people space my entire career and started my solopreneur journey 3 years ago. I focus on fractional people support, advisory in HR and AI, and project-based work primarily in the L&D niche from my years in leadership consulting and change management.