Published Date:
August 21, 2025

The Five Shifts to Confidently Lead with AI

AI is changing quickly. These five important shifts will help you move from being AI-curious to becoming a confident AI leader.
By
Daan van Rossum
Founder & CEO, FlexOS

Continuing with our theme of getting 10x more out of AI, I hosted a webinar on Tuesday for AI-curious leaders.

In it, I shared how to become the kind of confident AI leaders our ​Executive Boot Camp​ graduates transform into over the 3 weeks they spend with us.

Because while other ‘gurus’ are making AI difficult and unapproachable, I want to emphasize how AI is a new, friendly team member, just one that continues to become more and more capable over time.

If you couldn’t attend, here are the five simple steps to take so you too can be an AI leader.

The Five Shifts to Confidently Lead with AI

I agree: the acceleration of AI is the biggest we will see in our lifetimes.

We’ve moved quickly from AI as a simple chat interface (type in, get text back) to multimodal systems (voice, images, video) and are now in the agentic era where AI autonomously plans and acts.

That escalation raises a leadership question: how do we manage a hybrid team of people and AIs?

Two framing points set the stage:

With that context, I shared five shifts people make to move from AI-Curious to Confident AI Leaders, from mindset to supervision.

1: Treat AI as a colleague and brief it like one

Stop thinking of ChatGPT as a “tool.” Treat it as a capable colleague you need to manage, by setting its role, intent, and standards so it can produce work you would sign off on.

As I’ve repeated, good prompting is simply good delegation.

The ​CODO-Superprompt framework​ gives you a structure to get 10x more out of your prompts (see our free ​prompt generator​ to get started):

  • Character: Who should the AI be for this task? (e.g., experienced copywriter, board‑level advisor).
  • Objective: The outcome to enable, not the artifact (“convince my board to invest in …,” not “write a summary”).
  • Do’s & Don’ts: What good work looks like; frameworks, rules, and known traps to avoid based on your unique experience.
  • Output: The exact deliverable (one‑slide summary, risk–reward table, 500‑word memo) and an example if you have one.

Good prompts have become even more important with the introduction of ChatGPT-5.

​Prompting ChatGPT-5​ is different because the model is more steerable and more of a rule‑follower.

It also operates behind a router that chooses between two sub‑modes unless you instruct it otherwise, as ​I shared last week​:

  • Fast (chat) for quick responses.
  • Thorough (thinking) for deeper, more deliberate work.

Because the router decides, vague instructions can be sent to the wrong sub‑mode. The fix is explicit management within your prompt:

  • Mode: “Use thorough reasoning.” (Or, if speed matters, say so.)
  • Tools: State tool use allowances/limits (“Web search allowed; stop after first 5 sources for review.”)
  • Autonomy & checkpoints: Require a brief plan, interim summaries, and “pause for approval” gates.
  • Depth vs. brevity: You can ask for short outputs but deep internal reasoning.
  • Scope control: Limit the context you provide; the model is precise and can be tripped by conflicting signals.

2: Start from the work, not the tools

​Tasks, not tools​.

​Tasks, not tools​.

​Tasks, not tools​.

I sometimes feel the urge to let people write this on a chalkboard 100 times over, as many leaders start by shopping for platforms or signing up for tools recommended to them.

The much more reliable path is to inventory your actual work and prioritize where AI is natively strong. I use a simple filter: look for tasks that are General, Error‑friendly, and Digital. That’s where AI compounds quickly.

High‑leverage categories that came up repeatedly:

  • Research & analysis: Competitor scans, policy landscapes, pre‑read briefings.
  • Writing: Board updates, customer proposals, investor notes.
  • Preparation & rehearsal: Interview practice in voice mode, objection‑handling drills, and difficult conversations.

The discipline is to select a few workflows, introduce AI, and get excellent at them, rather than spreading your effort thinly across many tools.

Example: ​Boot Camp​ graduate ​Christine Kasoulis​, a senior UK-based retail executive (ex‑Sainsbury’s) mapped her calendar, identified research and interview preparation as the most impactful use cases, and paired core ChatGPT workflows with NotebookLM for deep research.

3: Use AI to expand capability, not only efficiency

I know it’s tempting to use AI as a productivity booster. And we should, especially in the context of those G.E.D. workflows where AI can be so helpful.

But eventually, capability expansion is the real destination, the place where we become those real AI Leaders managing a team of AIs.

Some low-hanging fruit in this realm are Deep research, commissioning multi‑source, citation‑rich briefings of up to tens of pages, and Presentation design, outsourcing formatting and layout to AI, while keeping your human judgment on message and narrative.

These new capabilities change the quality of your work, decisions, and communication, not just the speed.

Example: ​Kristen Cuneo​, former L&D lead at X, The Moonshot Factory (Alphabet’s innovation arm), refused to accept generic visuals for her new “​Speaking Spanishish​” blog.

She A/B‑tested multiple image generators on an intentionally quirky brief (“chinchillas learning about dust baths”) to pick a style that matched her brand.

Then she built a custom GPT tuned to that style so future images arrive on‑brand by default—an example of moving beyond speed to distinctiveness.

4: Move from off‑the‑shelf use to tailored assistants

Generic assistants create generic outcomes.

Superprompting is a first step, but Confident AI Leaders quickly run into the challenge that they spend a lot of time prompting.

This is where they tap into Custom GPTs and other AI Assistants, like the one from Kristen Cuneo above, to have ‘shortcuts’ to pre-prompted AI assistants tailored to their specific workflows and needs.

In our ​PRO Community​, we recently spoke to Moderna’s Head of AI, ​Brice Challamel​, who guided their team to create over 3,000 of these AI assistants:

One thing that came up during the session was when to use GPTs (​instructions here​), and when to use Projects. Here’s what I advise:

  • Projects (ChatGPT): Best for ongoing workstreams. You get custom instructions plus specialized memory across all chats in the project. New conversations start “warm” with context across previous ones.
  • Custom GPTs: Best when you want to share your assistant beyond your account (team, company, external). You can keep them private by default, but in that case, a Project may be the better option.

5: Graduate to agentic execution

A step above AI assistants are Agents, and they are becoming more helpful by the day.

Agents can now take goals, plan, browse, click, and deliver outputs, like comparing resumes and building a comparison sheet.

We took a look at ​ChatGPT Agent​ alongside specialist tools like Loveable for ‘vibe coding’ your own websites or apps.

Example: ​Anushka Arellano​ graduated from our ​Certification Program​ last week with a stellar example of taking charge.

An HR consultant in med‑tech, she used Lovable to prototype a lightweight HRIS from a single prompt. As a result, she now has a tailored platform for org chart and other core HR workflows.

The Bottom Line: Becoming a Confident AI Leader

As I said, AI does NOT have to be difficult. Anyone can turn their curiosity into confident AI leadership without any overwhelm.

The only must is diligence and restraint. Not every AI tool needs to be explored, and often learning to prompt your core AI (ChatGPT, Gemini, Copilot) gives you 10x the ROI of adopting yet another platform.

Adopt the colleague mindset, master delegation-quality prompting, layer in ChatGPT‑5 steering, ground adoption in real work, tailor assistants, and then supervise agents.

That’s how leaders move from “experimenting with AI” to running an AI‑powered operating system.

What’s missing? Reply and we’ll discuss.

Until next week,

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Last Chance to Join Lead with AI for $899. Price Increases to $1,098 at EOD Friday

The newly launched ChatGPT-5 will change the way leaders work with AI significantly, so upskilling has never been more important. This is your chance to skill up and turn GPT-5 + Agents into real outcomes.

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The Hidden Cost of GenAI-Powered Coding, The ‘Learning Gap’ Stalling 95% of GenAI Pilots, AI Agent Hype Check

I read dozens of AI newsletters weekly, so you don’t have to. Here are the top 3 insights worth your attention:

#1 The Hidden Cost of GenAI-Powered Coding

​A new MIT Sloan report​ warns that while generative AI can boost coding productivity by up to 55% (per GitHub and McKinsey data), it’s quietly piling up technical debt - duplicated code, brittle integrations, and mounting instability when applied to complex legacy (called “brownfield”) systems.

"Greenfield" projects benefit more safely from AI acceleration, but brownfield environments need discipline.

If you’re scaling AI-assisted coding, build clear usage guidelines, track technical debt proactively, and train developers to audit and refactor AI-generated code early.

​>> Read the full report here.​

#2 The ‘Learning Gap’ that Stalls 95% of GenAI Pilots

​A new report ​from MIT’s NANDA initiative finds that just 5% of enterprise GenAI pilots are driving real revenue gains, despite massive investment and hype.

Researchers point to a “learning gap” of tools and integrations. Tools aren’t being integrated deeply enough into workflows to create measurable impacts.

​In an interview with Fortune, lead researcher Aditya Challapally noted that startups win by focusing on a single pain point and executing quickly, while many enterprises spread efforts too thin, build in-house tools that underperform, and overinvest in flashy sales and marketing pilots instead of proven, higher-ROI areas like back-office automation.

​>> Read more insights here.​

#3 AI Agent Hype Check

​In his Forbes article​, Jotform CEO Aytekin Tank called out the trend of “agent washing.” Many are slapping the “AI agent” label on tools that are really just automations.

True agents are autonomous, adaptive, and improve over time; most tools today aren’t there yet.

The point isn’t to obsess over labels. It’s to set realistic expectations so you can adopt AI steadily and effectively. Hype burns out fast. Habits - testing, iterating, and finding where AI truly adds value - build staying power.

​>> Read the article here.

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Prompt of the Week

A good prompt makes all the difference, even when you're just using a core LLM.

Struggle with ideas for your next post? Try this prompt from Ruben Hassid's team.

What’s smart is how they prompt AI to dig for three angles with clear guidelines: one timely, one evergreen, one audience-led, so you don’t fall back on the same old takes.

Let AI Research Content Ideas

Think very deeply. I need you to search the web. Act like a social media expert who needs to find 3x different angles for a new article.

My niche is "[INSERT YOUR NICHE]".

A good article is:

- A recent news story (which means in the last 3 days or so) that went viral and impacted my niche. Be creative. Sometimes, the right news is not exactly following the keywords of my niche.

- An evergreen educational content that people need on my niche. Beware, it has to be extremely specific. For example, “How to use AI” isn’t specific but “How to prompt Midjourney to get a realistic fashion show photoshoot” is right for the niche “AI tools for designers.”

- Recent Reddit frustrations concerning my niche that went viral. Recent means in the last 7 days. You can also check in different languages.

👉 Try it, tweak it, and save it for your future use. If this prompt is helpful (or if you made it better), share with us here!

P/S: In ​our 3-week Boot Camp​, we help leaders master crafting ‘SuperPrompts’ and 10x their AI usage through practical exercises, even with just a core AI platform. We can help you do the same. ​Explore the program here and claim our promotion​.
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Exclusive for PRO Members only: Zapier's AI Revolution: Leadership Insights from Brandon Sammut

Lead with AI PRO is thrilled to host an exclusive Fireside Chat with Brandon Sammut, Chief People Officer at Zapier, on August 21 at 4 PM London / 5 PM Amsterdam / 8 AM Pacific / 11 AM Eastern.

Zapier is one of the most-discussed case studies in our community, having transformed into an AI-first organization with:

  • 90% of employees using AI daily
  • AI-integrated workflows across 8,000+ apps
  • A 750-person, fully remote team across 40+ countries

Brandon will share how Zapier is scaling human-centered AI adoption and how leadership can enable it. You’ll walk away with:

  • Proven strategies to embed AI across complex, global teams
  • Leadership practices that encourage adoption without fear
  • Practical insights you can bring directly into your own organization

🚨 Important: This conversation will not be recorded or distributed. It’s a rare chance to engage live, ask your questions, and gain unfiltered insights directly from Zapier’s leadership.

Want to join this exclusive event for PRO members?

Then it's time to upgrade - now two weeks for free:

2-WEEK FREE TRIAL

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If you made it this far, reply and tell me what you'd love AI to take over in your daily workflow.

Also, please forward this newsletter to a colleague and ask them to subscribe.

If you have any other questions or feedback, just reply here or inbox me.

See you next week,

Daan van Rossum - Lead with AI

Daan van Rossum​

Host, Lead with AI

Daan van Rossum

Founder & CEO, FlexOS

Continuing with our theme of getting 10x more out of AI, I hosted a webinar on Tuesday for AI-curious leaders.

In it, I shared how to become the kind of confident AI leaders our ​Executive Boot Camp​ graduates transform into over the 3 weeks they spend with us.

Because while other ‘gurus’ are making AI difficult and unapproachable, I want to emphasize how AI is a new, friendly team member, just one that continues to become more and more capable over time.

If you couldn’t attend, here are the five simple steps to take so you too can be an AI leader.

The Five Shifts to Confidently Lead with AI

I agree: the acceleration of AI is the biggest we will see in our lifetimes.

We’ve moved quickly from AI as a simple chat interface (type in, get text back) to multimodal systems (voice, images, video) and are now in the agentic era where AI autonomously plans and acts.

That escalation raises a leadership question: how do we manage a hybrid team of people and AIs?

Two framing points set the stage:

With that context, I shared five shifts people make to move from AI-Curious to Confident AI Leaders, from mindset to supervision.

1: Treat AI as a colleague and brief it like one

Stop thinking of ChatGPT as a “tool.” Treat it as a capable colleague you need to manage, by setting its role, intent, and standards so it can produce work you would sign off on.

As I’ve repeated, good prompting is simply good delegation.

The ​CODO-Superprompt framework​ gives you a structure to get 10x more out of your prompts (see our free ​prompt generator​ to get started):

  • Character: Who should the AI be for this task? (e.g., experienced copywriter, board‑level advisor).
  • Objective: The outcome to enable, not the artifact (“convince my board to invest in …,” not “write a summary”).
  • Do’s & Don’ts: What good work looks like; frameworks, rules, and known traps to avoid based on your unique experience.
  • Output: The exact deliverable (one‑slide summary, risk–reward table, 500‑word memo) and an example if you have one.

Good prompts have become even more important with the introduction of ChatGPT-5.

​Prompting ChatGPT-5​ is different because the model is more steerable and more of a rule‑follower.

It also operates behind a router that chooses between two sub‑modes unless you instruct it otherwise, as ​I shared last week​:

  • Fast (chat) for quick responses.
  • Thorough (thinking) for deeper, more deliberate work.

Because the router decides, vague instructions can be sent to the wrong sub‑mode. The fix is explicit management within your prompt:

  • Mode: “Use thorough reasoning.” (Or, if speed matters, say so.)
  • Tools: State tool use allowances/limits (“Web search allowed; stop after first 5 sources for review.”)
  • Autonomy & checkpoints: Require a brief plan, interim summaries, and “pause for approval” gates.
  • Depth vs. brevity: You can ask for short outputs but deep internal reasoning.
  • Scope control: Limit the context you provide; the model is precise and can be tripped by conflicting signals.