Trudy Graham

Trudy Graham School leadership is heavy. Host of the Trailblazing Schools podcast | Coach | Speaker

I help principals and middle leaders carry it better with smarter systems, stronger support, and AI that actually fits how schools work.

How much would you pay for a virtual assistant who never sleeps, never complains, and gives you your Sundays back?That's...
03/09/2026

How much would you pay for a virtual assistant who never sleeps, never complains, and gives you your Sundays back?

That's the question I put to school leaders who ask me whether it's worth paying for an AI subscription. Most of them have spent years outlaying money for classroom resources without blinking, textbooks, commercial products, printables, stationery. Nobody questions that spend. The second it's a monthly AI subscription, suddenly it needs to justify itself.

The free versions aren't actually free. You're not saving money, you're wasting time working around the paywall a subscription would remove, usually right at the moment you need the tool most.

My advice: trial the paid version for a month or two. It's billed month-to-month, so you can cancel any time if it's not earning its keep. And if you're in Australia and using it for your role, it's worth talking to your accountant about claiming it as a deduction.

Sometimes we make a decision based purely on a dollar figure, when the real cost we should be weighing is time. What's an extra afternoon a week actually worth to you?

I get into this, plus the two other questions I'm asked more than any others about AI in education, on this week's Trailblazing Schools Podcast episode. https://trailblazingschools.riverside.com/e/common-questions-about-ai-for-educators

01/09/2026

You're a principal, drafting a tough message to a parent. Before you hit send, you ask your AI: does this response seem fair?

It says yes.

But what is it really saying ‘yes' to? AI models are trained to be helpful, and helpful gets confused with agreeable. Ask it to confirm your read on a situation, and it will very often find you reasons you're right, not because it's true, but because of how you framed the question.

The fix is in the prompt. Instead of asking it to confirm what you already think, ask it to argue the opposite case. Instead of "does this seem fair?", try "what would the parent's strongest objection to this be?" That one shift catches blind spots before you hit send.

This matters more in leadership than almost anywhere else. You already have positional power. The people below you are less likely to challenge your thinking. If your AI is just nodding along too, you've built an entire feedback loop with nobody in it willing to say: have you considered you might be wrong here?

A few other prompts worth keeping on hand:
❓ What assumptions have I made?
❓ What perspectives have I overlooked?
❓ Give me five counterintuitive ideas.
❓ What would critics point out?

Full episode is on this week's Trailblazing Schools Podcast, including the two other questions I get asked more than any others. https://trailblazingschools.riverside.com/e/common-questions-about-ai-for-educators

Last year I needed to know every organisation in my local area, government, not-for-profit, and business, that employs a...
27/08/2026

Last year I needed to know every organisation in my local area, government, not-for-profit, and business, that employs a high number of STEM professionals.

Before AI, that task would have taken weeks or months. Honestly, I probably wouldn't have pulled it together myself at all - I wouldn't have had the time.

With AI, I had it in under ten minutes.

That's deep research mode, one of the options sitting in the prompt bar of most large language models, doing in minutes what would take a person days or weeks of digging. Prompt it with your niche topic and let it do the searching you'd never have time or resources for. Brilliant for researching teaching topics, school priority areas, demographic information about your community, or a specific challenge you need to get across quickly.

Most school leaders I work with only use AI as an editor, to draft emails, tidy up a newsletter, tighten a parent letter. That's the smallest part of what it can do.

I've also used it as a trainer to build and launch this podcast in a month, a data analyst to find patterns in survey feedback, a coach that asks me one question at a time, and a consultant that tells me exactly what information it needs from me to do the job properly.

Which of those are you not using yet? Full breakdown, with the exact prompts, is on this week's Trailblazing School Podcast episode: https://trailblazingschools.riverside.com/e/5-ways-to-use-ai-as-a-school-leader-beyond-writing-and-editing

On New Year's Day this year, I decided I wanted to start this podcast. I'd built one before, but that was five years ago...
25/08/2026

On New Year's Day this year, I decided I wanted to start this podcast. I'd built one before, but that was five years ago, and I didn't have time for a course or trial and error.

So instead of Googling "how to start a podcast" and drowning in generic advice, I gave ChatGPT a high-profile expert in podcasting and pointed it to their publicly available material. Then I asked it to build me a 30-day action plan based on what that expert had put out into the world.

What came back was specific episodes to listen to, blogs to read, activities mapped out day by day, built around what I already had and what I was missing. It felt like a mini course, tailored to exactly what I was trying to build. What would have taken weeks of trial and error compressed into a structured month.

We launched in February.

That's AI acting as a trainer, not an editor. Hand it a skill you need to build, point it at a real expert's material, and let it build you a personalised plan. Thirty days might not suit your reality in a school. Ten weeks, one task a week, might.

Most leaders only ever use AI to write and edit things. It can do so much more than that.

I share four other roles your AI tool can play, data analyst, researcher, coach, and consultant, on this week's episode of the Trailblazing School Podcast: https://trailblazingschools.riverside.com/e/5-ways-to-use-ai-as-a-school-leader-beyond-writing-and-editing

I built a business that, from the outside, looks like it's entirely about AI. I run workshops on it. I record podcast ep...
20/08/2026

I built a business that, from the outside, looks like it's entirely about AI. I run workshops on it. I record podcast episodes and write newsletters about it, most weeks.

But that's not the thing that truly makes the impact.

A few months ago, I went back through everything I've built over the last three years. Every case study. Every testimonial. Every piece of feedback from the principals and middle leaders I've worked with. I was looking for the moment AI showed up as the thing that changed them.

It wasn't there. Not once.

What they talked about instead was getting out of the weeds and into the work that actually matters. Leadership teams stuck in meetings that were just information sharing, everyone reporting on their own silo, nobody actually thinking together. Small school principals carrying everything because there's no one else to hand it to. Not a personal failing, the research has been calling this a structural problem in school leadership for fifteen years.

AI didn't fix that for any of them. What fixed it was candour, structure, and a leader willing to let go of the busyness that felt urgent so there was room for the busyness that actually mattered.

It was a strange thing to discover about my own business. I thought I was selling a tool, but what I've actually been building, apparently, is space for people to think.

I get into what that looks like in practice on this week's episode: https://trailblazingschools.riverside.com/e/getting-out-of-the-weeds-and-into-the-work-that-actually-matters

Lisa reconnected with me in 2024. She had a newly shaped leadership team at her growing school in Walloon, and she told ...
18/08/2026

Lisa reconnected with me in 2024. She had a newly shaped leadership team at her growing school in Walloon, and she told me straight: "I'm bogged down in operational, and that's not where I like to sit. I'm a big picture person."

Her team wasn't short on effort. They were, by her own account, amazing people who worked hard. What they were short on was candour. Their leadership meetings had become what she called "operational regurgitation": everyone reporting what they'd done, nobody challenging anybody else's thinking, everyone staying in their lane and calling it collaboration.

The first shift wasn't a tool. It was a distinction, the difference between teamwork and what I call "teamship". We rebuilt the meetings around tools that gamified challenge, and a framework to keep the team deliberate about which part of the work they were actually in.

A year later, Lisa calls it her most successful year in school improvement. She told her team directly: "I'm not interested in mini-me's. I need my thinking challenged." When she asked them afterwards whether they felt safe pushing back on her, they said yes, because she'd made it clear that was the job.

Yes, AI was part of Lisa's year. She uses it constantly now. But when I asked what actually changed her as a leader, she started with the team, not the tool.

Full story is on this week's episode: https://trailblazingschools.riverside.com/e/getting-out-of-the-weeds-and-into-the-work-that-actually-matters

Last year I found out something uncomfortable about my own leadership. Not from a colleague, but from ChatGPT.I'd been u...
13/08/2026

Last year I found out something uncomfortable about my own leadership. Not from a colleague, but from ChatGPT.

I'd been using it for months to draft emails, find themes in sessions, work through tricky feedback. One day I asked it something different: to analyse all our conversations and tell me my strengths, my progress, and the gaps I might not be aware of.

The strengths section felt like an affirmation. Clarity of vision. Strategic intent. Audience sensitivity. Nice to read, but what I expected, really

The gaps section is what made me start to feel a bit uncomfortable. Over-layering. Hidden perfectionism in iteration. Emotional load management. Three things I recognised instantly and would never have said out loud, because nobody else has been close enough to my daily decisions to see the pattern.

A colleague softens things. A supervisor picks their moments. AI has no stake in managing my feelings. It just reports what's there, which is exactly why the gaps section was the most honest feedback I've had in years.

We've mostly used AI to move faster. This is different. It's not making me more efficient at who I already am. It's making me more aware of who I'm becoming.

If fifteen minutes with a prompt can show you a leadership gap nobody else was positioned to see, what else might it show you if you started asking better questions?

I share the exact prompt, and what I did with what it told me, on this week's episode. https://trailblazingschools.riverside.com/e/the-leadership-coach-you-already-have

Most leaders I work with are drowning in feedback about their school and starving for feedback about themselves.Parent s...
11/08/2026

Most leaders I work with are drowning in feedback about their school and starving for feedback about themselves.

Parent surveys. Staff wellbeing data. Review panel notes. Mountains of information about how the school is going. Almost none of it is about how *you* are going.

What you do get arrives twice a year, filtered through a supervisor managing thirty other leaders, softened enough that the real pattern gets lost.

So I've got a trick for you to try. If you've been talking to AI regularly, it's been paying attention. You've just never asked it what it noticed.

I ran an experiment on myself for six months. I asked ChatGPT to analyse all my engagements with it over the last 30 days: my strengths, my progress, and the gaps I might not be aware of.

The strengths section was affirming. The progress section was a list of small wins I'd taken for granted. The gaps section was honest, and it stung. (Over-layering. Hidden perfectionism in iteration. Emotional load management.) All of it true in a way nobody else has the vantage point to tell me.

This isn't AI telling you who you are. It's AI showing you your own paper trail, which you wrote.

➡️ Try it this week.
Open whatever AI tool you already use and paste in this exact prompt:
"Analysing all my engagements with you over the last thirty days, what have been my strengths? Where have I made progress? And what are the gaps I may not be aware of?"

Read the whole thing before you react to any one line. Reply in the comments if you try it, I'd love to know what it tells you.

School leader friends who are passionate about helping kids learn to read, consider completing this survey, share it in ...
10/08/2026

School leader friends who are passionate about helping kids learn to read, consider completing this survey, share it in your network, and generally work your magic. Thanks, T.
______________________

Calling All Queensland School Leaders! – Share Your Insights on the Provision of Reading Interventions at Your School

QUT Ethics Approval Number: 7688

If you are a Principal, Deputy Principal, Head of Curriculum or other learning support leader currently working in a Queensland Primary School and have insights into how your school supports students with persistent reading difficulties, you are warmly invited to participate in this study.

This research is being conducted by Cheryl Hooper, a doctoral candidate in education, as part of her studies toward the completion of the degree of Doctor of Education.

The purpose of this research project is to explore how schools are implementing interventions for students with persistent reading difficulties.

The survey takes around 30 minutes to complete and includes choosing from set responses with opportunities for extended responses. Responses are confidential and you will be deidentified in any reports or journal articles.

Click here to complete the survey: https://qsurvey.qut.edu.au/jfe/form/SV_b8ip47LLjVnvrH8

To all my colleagues, thank you for the amazing work you do, the difference you make and the impact you lead.
07/08/2026

To all my colleagues, thank you for the amazing work you do, the difference you make and the impact you lead.

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