Another Training Request
You weren’t asked to be the leadership program development team. But here it is. It landed in your inbox with a deadline and a one-line description: “Something on resilience, needs to be ready by Q3.”
No conversation about why. Just the standard training request.
You don’t know what’s actually going on with the team it’s for. You weren’t in the meeting where someone decided this was the answer. You were the lucky one who got the homework.
In Part 1, we talked about the five chess pieces and the strategic thinking you already have. But what if that’s not where you are right now? What if most days feel less like chess and more like checkers? There are moves you can see and moves you can make, but nothing that feels like you are in a position to actually be strategic.
You are not alone in this feeling. In fact, there MANY L&D professionals sitting in the same space you are right now. (I’d love to hear
The Problem With “Be More Strategic” Advice
Open LinkedIn on any given day and you’ll find the consultant who’s never worked your job (or any meaningful L&D role) telling you to “learn more about the business,” “build relationships with the C-suite,” or “stop waiting for permission.” All true. However, none of it tells you how. How do you do this when the VP doesn’t even know your name, and your manager would raise an eyebrow if you started “asking strategic questions” about a project you were just told to execute?
And underneath all that advice is an assumption that, if you’re not doing those things, it’s because you’re not trying hard enough. That you just need to be bolder. Puleeze.
(Full disclosure. I’ve written some of that advice myself, just hopefully, in a more helpful manner.)
A while back, I wrote that getting a seat at the table isn’t the point. This is still true. And while I provided 5 action steps and a 30-60-90-day plan to help you better understand what is happening around you, there are many articles offering advice written only for people who already have deep relationships already built. People who already have a relationship to leverage, a meeting to walk into, a track record that buys them the benefit of the doubt. When these advisors say “just ask,” they’re not living in your current reality.
(Curiosity Calls: In the comments, share the advice that’s technically true but completely useless from where you sit?)
L&D Strategy: Playing Chess Without an Invitation
So what does “playing chess” actually look like when you’re not the one moving the big pieces?
Here’s something that gets left out of most every “level up your strategy” article: nobody starts a chess game by sitting down across from a grandmaster and making moves. They start by watching. Studying other people’s games. Noticing why a move worked three turns later, even though they couldn’t have made that move themselves yet.
That’s not a lesser way to learn chess. It’s the way. Every strong chess player spent time watching boards they weren’t playing on.
Checkers, by contrast, doesn’t ask for that kind of attention. Checkers asks “what’s my best move right now?” Chess asks “what does this move set up three turns from now?” Same board, same pieces, but a completely different question running in the background. There’s nothing wrong with that game, it’s literally how most L&D roles are built.
And I know, the gap between “playing checkers” and “playing chess” looks like the Grand Canyon from where you’re standing. Trust me, it’s not. It’s simply a practice period, and you’re ready to jump the gap, whether you realize it or not.
The reality is that every request that lands on your desk is a move someone else made. The choice you have is either to move directly to execution or to start reading it. What does this request tell you about what’s happening upstream? Why this, why now, why you? You don’t get to make the next move yet. But you can start seeing it coming.
That’s not “stuck.” That’s study. And it’s exactly where the next moves begin.
Move 1: Read Beneath the Request, Strategic Thinking Starts Here
Before you can anticipate what’s coming, you have to get good at reading the move in front of you, the one that just happened. Really reading it, not just executing against it. When a request lands, ask one question that helps you see what’s behind it.
Pick whichever fits the situation:
- “Is there a date or event this training is tied to?” If the answer is “the all-hands is in six weeks” or “this came out of the engagement survey,” you’ve just picked up a piece of the story you didn’t have before, and that changes how you read the board before any piece has been moved.
- “Has something like this been tried before?” If yes, ask one follow-up: “Do you know how the training was received?” That’s often where the real story comes out. What’s been tried, what worked, what didn’t, and why this is happening again.
- “Who else should I loop in?” The name that comes back is often the player who actually has a stake in the game. Worth remembering, because you’ll need it for Move 4.
None of these sound like strategy. That’s the point. They sound like someone doing their job carefully, and the answers will give you information that can drive some of your design decisions.
Move 2: Build the Thing, Then Set Up Your Next Move
In chess, even early moves aren’t isolated. A pawn pushed in turn three can open a path for a bishop five turns later. You can build that habit now, even from an execution-only seat.
Build the thing you were asked for, on time, and to spec. Then add one small piece that sets up something later.
Pick whichever fits the situation:
- A one-page “manager’s guide” covering points on what to reinforce in 1:1s over the next month.
- A short “tip of the week” for managers to send their teams two weeks after rollout. Something that reinforces one idea from the training without anyone having to remember to write it.
- A short “if this comes up again” note for your debrief log. What worked, what you’d change. This is to study for your next game.
Pick one that won’t take a long time to create. Nobody has to approve it, and nobody’s going to tell you not to include it. But it’s a move that sets something up for the next time this exact thing lands on your desk.
Move 3: Track Patterns, This Is How L&D Strategy Skills Develop
Serious chess players review past games, their own and others’, looking for patterns they missed in the moment. You can do the same with training requests.
Keep a log. Open a doc or spreadsheet every time something lands on your desk, note four things:
- What was asked for
- Who asked
- What reason was given (if any)
- What was actually going on with that team or department at the time (even if you only learn that part later)
Review it every few months. You’re checking for repeats: the same department asking for “communication training” every 9 months. You may notice the same type of request showing up right after a round of engagement surveys or a “leadership program” request that turns out to be connected to three managers quitting. Data tells a story.
You’re not building this for a presentation, and you don’t need to share it with anyone. You’re building your own study material, because once you can say “this is the third time this exact request has shown up after this exact situation,” you’re no longer reacting to moves. You’re starting to recognize them before they’re made.
Move 4: Influence Without Authority Starts With One Person
Even players who aren’t ready to compete benefit from someone to study with, someone to say “wait, why did they do that?” out loud to.
Find the manager, team lead, or peer who actually has to live with the outcome of what you’re building. Not the stakeholder. Look for the person whose team will sit through it or whose problem it’s supposed to solve.
Loop them in early, even informally: “Hey, I’m working on the thing for your team, anything specific you’re hoping it addresses?”
Here’s what happens next, and it’s one of two things. Either they tell you something nobody else mentioned, and now you’ve got information that changes what you build. Or they shrug, say “not really, just whatever’s standard,” and go back to their day.
The second outcome isn’t a dead end. It’s data.
It tells you this manager doesn’t see training as something that affects their team’s actual problems, which is a pattern worth tracking in its own right (see Move 3). And it costs you nothing. You asked a normal-sounding question, got a normal-sounding non-answer, and moved on exactly as planned.
But when it works, and often enough, it does; you’ve found someone who now knows you’re paying attention to their team specifically, not just shipping them random programs. The best thing is that the relationship doesn’t disappear after this project. Next time something for their team lands on your desk, you already have a name to loop in. That’s not networking. That’s remembering who said something useful and may do so again.
You’re Already Playing the L&D Strategy game. You’re Just Learning to See the Board.
Look back at those four moves for a second. None of them require permission. None of them require a title change, a new manager, or someone finally noticing you. They’re things you can start doing this week, in the job you already have, without announcing it to anyone.
The gap between “stuck in checkers” and “playing chess” was never about access. It was about using your skills differently, and how you use your skills is something you’ve had control over the whole time.
So picture that leadership program request again. The one that landed in your inbox with a deadline and not much else.
This time, you build it. On time, to spec, same as always.
But this time, you asked one question, and the answer told you this request came in right after a round of exit interviews flagged burnout on one specific team. Because of this, you added a one-page manager’s guide about “Observing for Burn-Out”, something nobody asked for, and nobody told you not to include. You wrote the request down in your log. And you mentioned the project to that team’s manager, who said, “Oh…that’s exactly what’s been happening.”
From the outside, nothing looks different. Same request, same deadline, same deliverable.
But you read that board before you built anything. And the next request that lands on your desk…you’ll read that one too.
If this post hit a nerve and you want to think through what playing chess looks like in your specific situation, let’s talk. A 20-minute conversation costs you nothing and might reframe everything.
