TODAY’S THOUGHTS ☠️
Hey friend 👋,
There is no school or qualification that teaches you how to operate as a L&D pro.
Nearly everything is focused on learning design, but that alone will not enable your success or the ability to make real change in your work. I’m sorry to be the old man waving his stick in the air, yet you need much more than a good learning experience.
And AI is not gonna save you here either.
Most of my success inside organisations has had very little to do with building learning experiences. It’s had everything to do with understanding the conditions for success in that environment.
So, today, we’re exploring how to be a truly strategic L&D operator by matching your work with your organisation’s conditions for success.
Get your tea or beverage of choice ready 🍵.
We've got lots to discuss!
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IN THIS DROP 📔
Why designing good learning experiences isn’t enough
How to uncover your conditions for success
Building AI agents to roleplay difficult conversations

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THE BIG THOUGHT 👀
How To Be A Truly Strategic L&D Operator

The energy I want you to bring
There’s like a bazillion frameworks, models and systems kicking around the L&D industry promising the holy grail of “learning that transforms behaviours and drives performance”.
That’s led to many well-intentioned practitioners I’ve worked with believing that being a good L&D operator & leader is only about building great learning experiences and products with those tools.
❌ They’re wrong.
It’s about knowing how to navigate your business to deliver the outcomes it wants.
Not all organisations are created equal.
What the courses, accreditations and all the ‘experts’ can’t tell you are your organisations:
Culture
Constraints
Context
Knowing these are instrumental to any success you will have.
I learned this the hard way.
I once naively thought my output was all based on how good my learning experiences were. I was wrong.
No one really cared about that.
What they did care about was performance and building useful skills. To do that, and do it well, you need to understand the conditions for success (the list above) of your organisation.

What it means to be Strategic
Before we get into the meat of everything, let me define what I mean by “Strategic” because a lot of people throw that word around, and without context, it can be utterly confusing.
I don’t class being ‘strategic’ as a skill, it's more a capability. In the context of this article, we can say ‘being strategic’ means accurately reading your organisation's culture, constraints, and context, then using that to influence outcomes.
It’s a lot of the stuff we’ve discussed before in performance consulting.
Like connecting what you do to business outcomes (yes, you really need to do that), reading the politics across the organisation and knowing what to prioritise for the business. What we add is a shift in what you optimise for. So that’s definitely not just "did I produce something good," but "did I understand what the business actually needs, and did I move it closer to that."
Now we’ve cleared that up, let’s get to our conditions for success.
We’ll start with culture as this feels like the domino that influences the other two.
1/ Culture
I find culture to be such a strange thing.
Companies believe it’s something they control. They spend millions trying to shape it by rolling out EVPs, values, ping-pong tables etc. You name it, they’ll do it.
For you, culture plays an important part in what you can deliver as a L&D team or operator.
For this context, I’m going to frame culture for L&D as the understanding of ‘what is learning in the modern age’. This is a fickle topic. Everyone has their own take.
I learnt early in my career that if I was building amazing digital solutions but my company culture viewed learning as the traditional education model of classrooms. Then I wasn’t going to succeed.
You know, I can bring the Mona Lisa of L&D experiences, but my audience is like “Why aren’t we together in the same room so we can have fun, and where’s the free lunch?” 🥴
In any large organisation, you have to appreciate the culture towards L&D.
That means unpacking their understanding of workplace learning today. For most organisations, it's the education model. They look at the school model, and that's the model that continues to be repeated in corporate organisations because you know, why not?
They know no other alternative.
It's cheap, people know it and they'll go with it, but half the time, that doesn't work for performance. You know this but they don’t. This is an important distinction.
Going in all guns blazing to change this overnight is not going to happen.
90% of stakeholders want to tell you the solution to their problem
This has been constant across the nearly two decades I’ve spent in the industry.
Typically, stakeholders fall into two camps:
I think I have a training problem and want you L&D person to facilitate a classroom workshop.
I still think I have a training problem. I want you L&D person to create a point-and-click e-learning experience because I want something interactive.
Before you pull your hair out, let’s explore why this thinking occurs:
Our education system has brainwashed us to believe that ‘learning’ anything must be a designated event.
Naturally, this pours over to the working world. If it’s the only system you know, why would you do anything else? The problem is the world of work is not school.
Organisations don’t see L&D as performance based. They label it as education. Which leads many to believe it is nice to have.
It’s difficult to introduce new ways of thinking with such an established attitude towards L&D.
You’re not going to walk into a company and change the strategy from ‘here’s our list of courses’ to 'how can we design the best solution to x problem for this audience’.
You’ve got to play the long game.
So, as hard as it might seem, you gotta roll with it for a while. This is your first lesson in navigating the corporate game.
→ Know the culture of your company deeply.
This will enable you to build solutions that fit its maturity level and help you on the journey to evolve that level. It's going to be a journey, not an overnight makeover.
2/ Constraints

Stuck in a glass cage of constraints
This section nicely carries on from culture.
Now we understand the culture of the organisation, you can unearth its constraints.
Constraints come in many forms, including:
Debunking traditional knowledge
Negotiating delivery methods
Order-taking vs performance conversations
Budget
Resource
L&D teams often have ludicrous demands put on them.
We’re branded as some kind of chameleon-like knowledge centre that needs to be experts on Performance, Wellbeing, Diversity, Talent Management, why x sucks at doing x and so forth. It’s like being the local information point for the organisation.
You’re never going to escape this entirely.
Sadly, you’re going to be faced with doing and building products and experiences that you don’t agree with. This is part of the corporate game we all play. This doesn’t mean you can’t change this over time.
But don’t be a bull in a China Shop.
You're not going to stop this gigantic system. Although we love to say let's disrupt L&D and break the wheel, which I think it's good in some aspects, but to do that in an environment as a professional in the context of your organisation and the constraints that you've got is incredibly difficult.
It’s very aspirational. It’s generally a marketing tagline from consultants or vendors who’ve never done the actual job.
I know this sounds very doom and gloom.
Let’s shift gears and explore how you can challenge these constraints by taking people on a journey.

Help is coming
When in doubt, build a Trojan horse 🐴
Back in the 5th century (a long time ago) the Greeks and Trojans were at war.
It was not going well for the Greeks. They’d been attempting to break down the city of Troy for 10 years. The siege felt like it would never end. The Greek king Odysseus had an idea that would change the tide of this war.
Odysseus created a new tactic that has echoed throughout the pages of history.
He built a wooden horse. I know, very revolutionary. Odysseus hadn’t lost his mind, he was seeing more clearly than ever.
Winning the war by brute force wasn’t going to work. The Greeks have been doing this for 10 years with nothing to show.
Instead, they created a trick.
One day, the Greeks pretended to sail away from Troy.
The Trojans believed they had given up. Outside the city walls, the Greeks left a wooden horse as a parting victory trophy for their enemies. The Trojans accepted and brought the horse into the city.
Little did they know, not all the Greeks had left.
Odysseus and a group of his men secretly hid within this wooden horse to gain access to the city.
When darkness fell, the troops jumped out of the horse to open the city gates for the rest of the Greek army who had sailed back after their fake departure.
Within hours, the Greeks destroyed the city, concluding the fall of Troy.
The Trojans played the smart move.
What does this have to do with transforming your company's L&D strategy? A lot.
You can either choose to pursue a fruitless multi-year siege in telling stakeholders they’re wrong and you’re right. Which will 100% end up with them shutting down on you like the unbreakable gates of Troy.
Or, you can deploy the long game and switch to a smarter tactic.
How to deploy your Trojan horse
When a stakeholder wants a particular solution and you know you have no leverage in the matter, don’t fight it.
The battle will be pointless and you’ll likely end up in the same place.
Instead, build the solution(s) they want but drop in 10% of the stuff you know works better.
The play here is to neither give up nor try to start a war.
You find opportunities to weave in new ways of thinking and approaches into existing experiences. You’ll then compound this play over time.
What I've found is stakeholders typically get excited about that 10% bit and want more of that. It's not a 100% win rate of course.
And, it has to be something that delivers a clear impact. You can’t do something different to have it fall flat and kill your play.
The idea is to be strategic in your order-taking.
You can't expect people to change because you tell them to. It takes months, even years to win hearts and minds.
It's worth the effort.
3/ Context

Context is a huge unlock in any work you do.
Building your credibility can be supercharged by truly understanding people's problems.
That’s our role in L&D after all - problem solvers.
And who doesn’t want to be best friends with a problem solver? Exactly.
I’ve never seen better examples of this than when building a learning strategy and grappling with the local finance team over budget to deliver it. Organisational context on what it needs to hit its business goals vs what leaders want from you as an L&D leader is crucial here.
You’ll find a middle ground, no doubt.
But the point is the more context you have on what the organisation cares about, the better advice you can share as a strategic leader.
I’ve been in rooms where cookie-cutter L&D strategies and solutions are recommended every year to the same people. They all end in the same way - nothing.
That’s all down to not understanding the context of the organisation today.
When I say context, this specifically means:
Current business maturity
Business goals
Budget, resources and capabilities
Our previous two points of culture and constraints
Employee's attitudes and motivations for performance
It’s not cringey to say that context is life.
Don’t worry, I said that, not some weird LLM pretending to be me.

Final Thoughts
Deeply understanding these elements sets you apart as not only a good L&D operator but also a great strategic thinker.
Your big challenges are:
Understanding these 3 conditions for success
Explore how to influence these as an L&D team, operator and leader. If you try to fight against those, it's like when you go to Vegas to try and bet against the house, the house always wins.
That theme has been woven through all organisations that I've worked with.
This isn’t a magic bullet. I know you want me to say, do these 10 things and then you'll be able to do everything. But, it's not really how it works. It requires a great deal of patience and exploratory work on your end.
Change takes decades, not days
TL;DR (Too Long, Didn’t Read)
You need to navigate the specific culture, context and constraints of your company to have a high-performing L&D team. L&D skills on their own are not enough and not useful unless these 3 are understood deeply.
Industry advice means nothing if it doesn’t work for your organisation's current maturity level.
For real success, the change that the industry seems to crave. You have to become strategic. You need to understand how to play the game of your organisation and understand its conditions for success.
Learn the rules so you can evolve them. Just as we preach understanding our end user, we must understand how the organisation lives and breathes.
Doing this provides results. It’s about the long game and an infinite mindset. Disruption is overrated, smart innovation is better. Recognise the game you’re playing and the 3 elements I share to become a strategic L&D operator who will:
Drive impact and results
Build their credibility with the internal fabric of the organisation
Build a foundation for long-term success and performance improvement
You don’t need that mythical seat at the table to deliver impact. You just need to get savvy.
See you next time, human.
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👀 ICYMI (In case you missed it!)
Shape my latest research study on the skills L&D teams need to deliver impact today. I want to find out what skills you think a modern L&D team needs to thrive and survive in this era. Do that by answering my one question only survey and you’ll get the results in this very newsletter in late August.
Build your personal L&D research analyst with me using NotebookLM. Come work with me for 30 minutes on August 26th and I’ll show you how to build a high-performing L&D research analyst powered by AI that will keep you sharp in relevant insights to improve your learning experiences.
What I’ve learnt from high-performing organisations on the importance of making AI fluency part of the organisational culture. In only 15 minutes on August 27th, I’ll be sharing some of the biggest lessons I’ve learned from CLO’s, L&D teams and many more on what it really takes to make AI fluency a success.
A MESSAGE FROM THE AI-NATIVE L&D PRO
The doors are open for my next half-day workshop.
Join me and ten L&D pros on 20th August to connect, learn, and get a complete operating system for working with AI in your L&D role.
I don't believe you need to spend days or weeks getting to grips with the fundamentals of AI today. You should also know that this isn't a tool demo or a prompting workshop.
It's a structured, hands-on session designed to give you a complete operating system for working, thinking, and building with AI in your L&D role.
VIDEO THOUGHTS 💾
Let’s Build an AI Voice Agent To Practice Difficult Conversations
We spend a lot of time teaching people what to say in difficult conversations.
Yet we spend almost no time letting them practice how to say it. You're never going to learn tone, timing, or emotional regulation from a slide deck.
In this video, I'll show you how I built a fully working voice agent in ElevenLabs to practice a difficult performance conversation in a private space.
This is another way to transform learning (not do the same old thing) with AI.
Enjoy 😊.
Till next time, you stay classy, learning friend!
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