loader from loading.io

EP 269 - Why One-Off AI Training Fails (and What to Do Instead)

AI Literacy for Entrepreneurs

Release Date: 12/23/2025

EP 274 The Human OS - AI Adoption With Curiosity, Safety, and Monday Ease ft. Melissa Penton show art EP 274 The Human OS - AI Adoption With Curiosity, Safety, and Monday Ease ft. Melissa Penton

AI Literacy for Entrepreneurs

In the final episode of the Podcast-to-Book series, host sits down with change leader and AI education lead (Sun Life) for a human-first conversation about what actually makes AI adoption work. They talk productivity vs room-for-life, why one-prompt culture is snake oil, the shift from prompt engineering to context engineering, and the simplest enterprise question that changes everything: “What would make Monday easier for employees?” Episode summary Susan closes out the Podcast-to-Book sprint with a conversation that feels like the point of the whole series: AI isn’t a tool problem....

info_outline
273 - Future-proofing your organization through continuing AI literacy show art 273 - Future-proofing your organization through continuing AI literacy

AI Literacy for Entrepreneurs

Most companies do a few AI trainings, run some pilots, and then stall. In this episode, host argues the only real future-proofing strategy is continuous AI literacy. She breaks down what “continuous literacy” actually includes (skill, judgment, workflow, norms), the predictable failure modes of the AI literacy divide, and a simple flywheel you can run monthly so capability keeps compounding. Episode summary Susan opens with a familiar pattern: a burst of AI excitement, a deck called “AI Strategy 2025” a few clever workflows… and then reality hits. Tools change. Policies shift....

info_outline
EP 272 - Mindset, Sales, and AI That Actually Helps with Gazzy Amin show art EP 272 - Mindset, Sales, and AI That Actually Helps with Gazzy Amin

AI Literacy for Entrepreneurs

Host sits down with sales strategist , founder of Sales Beyond Scripts, to talk about the real ways AI is changing revenue, planning, and scale. They cover AI as a thinking partner, how to use it across departments in a small business, why audits matter more than hype, and how mindset quietly determines whether you treat AI as a threat or an advantage. Episode summary This episode is part of Susan’s 30-episodes-in-30-days “podcast to book” sprint for Swan Dive Backwards. Susan and Gazzy zoom in on the selling process first. Then they zoom out to the whole business. They talk about three...

info_outline
EP 271 - How to Quantify AI ROI Beyond ‘Time Saved’ show art EP 271 - How to Quantify AI ROI Beyond ‘Time Saved’

AI Literacy for Entrepreneurs

If you’re measuring AI success by “hours saved” you’re playing the easiest game in the room. In this episode, Host explains why time saved is weak and sometimes harmful, then shares a better “AI ROI stack” with five metrics that map to real business value and help you build dashboards that actually persuade leadership.   Episode summary Time saved is fine. It’s also table stakes. Susan breaks down why “we saved 200 hours” is the least persuasive AI metric, and why it can backfire by punishing your early adopters with more work. She then introduces a smarter approach: a...

info_outline
EP 270 - From AI Awareness → AI Readiness → AI Adoption with Jennifer Hufnagel show art EP 270 - From AI Awareness → AI Readiness → AI Adoption with Jennifer Hufnagel

AI Literacy for Entrepreneurs

Host sits down with (Hufnagel Consulting), an AI educator and AI readiness consultant who’s trained 4K+ people. They break down what “AI readiness” actually means (spoiler: it’s not buying Copilot), why AI doesn’t fix broken processes or dirty data, and how leaders can build real capability through training programs, communities of practice, and properly resourced AI champions. Episode summary and met in “the most elite way possible”: both were quoted in The Globe and Mail about women and AI. Jennifer shares her background as a business analyst and digital adoption / L&D...

info_outline
EP 269 - Why One-Off AI Training Fails (and What to Do Instead) show art EP 269 - Why One-Off AI Training Fails (and What to Do Instead)

AI Literacy for Entrepreneurs

If your organization ran an “AI 101” lunch-and-learn… and nothing changed after, this episode is for you. Host explains why one-off workshops create false confidence, how AI literacy is more like learning a language than learning software buttons, and shares a practical roadmap to build sustainable AI capability. Episode summary This episode is for two groups: teams who did a single AI training and still feel behind, and leaders realizing one workshop won’t build organizational capability. The core idea is simple: AI adoption isn’t a “feature learning” problem. It’s a...

info_outline
EP 268 Women, AI, and ‘Hold the Door’ Leadership with Chris McMartin show art EP 268 Women, AI, and ‘Hold the Door’ Leadership with Chris McMartin

AI Literacy for Entrepreneurs

Host is joined by , National Lead for the Scotiabank Women Initiative (Business Banking), for a real-world conversation about how women are approaching AI. They talk about time poverty, fear of asking “dumb” questions, the shame myth of “AI is cheating”, and why the most powerful move right now is women holding the door open for each other - learning in community and sharing what works. Episode summary This episode is a candid, energetic conversation with Chris McMartin - aka “Hype Boss” online and a long-time hype woman for women entrepreneurs. They explore what’s different...

info_outline
EP 267 Does AI Make you More or Less Creative? (Paintbrush vs Photocopier) show art EP 267 Does AI Make you More or Less Creative? (Paintbrush vs Photocopier)

AI Literacy for Entrepreneurs

AI can feel like a creativity cheat code… or like the death of originality. In this short, punchy solo episode, Susan argues the truth is simpler: AI doesn’t create creativity. It creates options. Creativity still belongs to the driver—your taste, courage, and point of view. Episode summary Susan tackles a question she hears constantly: does AI expand creativity or flatten it? Her answer: it depends on how you’re using it. If you use AI like a photocopier—generate a first draft and ship it unchanged—you’re not becoming more creative. You’re becoming more efficient at being...

info_outline
EP 266 - Literacy, Leadership, and the ‘AI for the Sake of AI’ Trap with Shona Boyd show art EP 266 - Literacy, Leadership, and the ‘AI for the Sake of AI’ Trap with Shona Boyd

AI Literacy for Entrepreneurs

Host is joined by , a product manager at Mitratech, a SaaS company, and a proudly AI-curious early adopter, for a grounded conversation about what AI literacy actually means now. They talk about representation, critical thinking, everyday meet-you-where-you-are workflows, shadow AI, enterprise guardrails, and why leaders must stop chasing AI features that don’t solve real user problems. Episode summary Susan introduces Shona Boyd - AI-curious early adopter and SaaS product manager—whose mission is to make AI feel less scary and more accessible. Shona shares how her approachable AI...

info_outline
265 Buying AI vs Building AI - A Leader’s Decision Guide show art 265 Buying AI vs Building AI - A Leader’s Decision Guide

AI Literacy for Entrepreneurs

Most teams are stuck in tool obsession: “Should we build agents?” “Should we buy this AI platform?” In this solo, workshop-style episode, host pulls you back to reality with a simple decision guide: buy vs bolt-on vs build, four leadership filters, and a practical workflow exercise to help you choose the right approach - without falling for agentic fantasies. Episode summary Susan opens with a pattern she’s seeing everywhere: 75% of AI conversations revolve around tools - agents, platforms, add-ons - and they’re often framed as all-or-nothing decisions. She reframes it: AI is best...

info_outline
 
More Episodes

If your organization ran an “AI 101” lunch-and-learn… and nothing changed after, this episode is for you. Host Susan Diaz explains why one-off workshops create false confidence, how AI literacy is more like learning a language than learning software buttons, and shares a practical roadmap to build sustainable AI capability.

Episode summary

This episode is for two groups:

  1. teams who did a single AI training and still feel behind, and

  2. leaders realizing one workshop won’t build organizational capability.

The core idea is simple: AI adoption isn’t a “feature learning” problem. It’s a behaviour change problem. Behaviour only sticks when there’s a container - cadence, guardrails, and a community of practice that turns curiosity into repeatable habits.

Susan breaks down why one-off training fails, what good training looks like (a floor, not a ceiling), and gives a step-by-step plan you can use to design an internal program - even if your rollout already happened and it was messy.

Key takeaways

One-off AI training creates false confidence.
People leave either overconfident (shipping low-quality output) or intimidated (deciding “AI isn’t for me”). Neither leads to real adoption.

AI literacy is a language, not a feature.
Traditional software training teaches buttons and steps. AI requires reps, practice, play, and continuous learning because the tech and use cases evolve constantly.

Access is not enablement.
Buying licences and calling everyone “AI-enabled” skips the hard part: safe use, permissions, and real workflow practice. Handing out tools with no written guardrails is a risk, not a training plan.

Cadence beats intensity.
Without rituals and follow-up, people drift back to business as usual. AI adoption backslides unless you design ongoing reinforcement.

Good training builds a floor, not a ceiling.
A floor means everyone can participate safely, speak shared language, and contribute use cases—without AI becoming a hero-only skill.

The four layers of training that sticks:

  1. Safety + policy (permission, guardrails, what data is allowed)

  2. Shared language (vocabulary, mental models)

  3. Workflow practice (AI on real work, not toy demos)

  4. Reinforcement loop (office hours, champions, consistent rituals)

The 5-step “training that works” roadmap

Step 1: Define a 60-day outcome.
“In 60 days, AI will help our team ____.”
Choose one: reduce cycle time, improve quality, reduce risk, improve customer response, improve decision-making.
Then: “We’ll know it worked when ____.”

Step 2: Set guardrails and permissions.
List:

  • data never allowed

  • data allowed with caution

  • data safe by default

Step 3: Pick 3 high-repetition workflows.
Weekly tasks like proposals, client summaries, internal comms, research briefs.
Circle one that’s frequent + annoying + low risk.
That becomes your practice lane.

Step 4: Build the loop (reps > theory).
Bring one real task.
Prompt once for an ugly first draft.
Critique like an editor.
Re-prompt to improve.
Share a before/after with the team.

Step 5: Create a community of practice.
Office hours.
An internal channel for AI wins + FAQs.
Two champions per team (curious catalysts, not “experts”).
Only rule: bring a real use case and a real question.

What “bad training” looks like

  • one workshop with no follow-up

  • generic prompt packs bought off the internet

  • tools handed out with no written guardrails

  • hype-based demos instead of workflow practice

  • no time allocated for learning (so it becomes 10pm homework)

Timestamps

00:00 — Why this episode: “We did AI training… and nothing changed.”
01:20 — One-off training creates two bad outcomes: overconfident or intimidated
03:05 — AI literacy is a language, not a software feature
05:10 — Access isn’t enablement: licences without guardrails = risk
07:00 — Cadence beats intensity: why adoption backslides
08:40 — Training should build a floor, not a ceiling
10:05 — The 4 layers: policy, shared language, workflow practice, reinforcement
12:10 — The 5-step roadmap: define a 60-day outcome
13:40 — Guardrails and permissions (what data is never allowed)
15:10 — Pick 3 workflows and choose a low-risk practice lane
16:30 — The loop: prompt → critique → re-prompt → share
18:10 — Communities of practice: office hours + champions
20:05 — What to do this week: pick one workflow and run one loop

If your organization did an AI 101 and nothing changed, don’t panic.

Pick one workflow this week.
Run the prompt → critique → re-prompt → share loop once.
Then schedule an office hour to do it again.

That’s how you move from “we did a training” to “we’re building capability”.

Connect with Susan Diaz on LinkedIn to get a conversation started.

 

Agile teams move fast. Grab our 10 AI Deep Research Prompts to see how proven frameworks can unlock clarity in hours, not months. Find the prompt pack here.