Welcome to Work Tip Wednesday, where every Wednesday I get ready and talk about career, leadership and a piece of advice I've learned working for some of the world's biggest brands.
One of the fastest ways to elevate how you are perceived at work is to start preparing like the person who already operates at the next level. And these days, AI tools make it dramatically easier to anticipate what your boss, your CFO, or the most opinionated person in the room will actually care about before you walk in.
Earlier in my career I had to learn this through a lot of trial and error. There were meetings where I walked in with a strong idea and got flattened by an angle I had not considered. Each one taught me something. The prompt I am about to share would have saved me half of those situations.
The Real Challenge
Most professionals prepare for meetings by rehearsing their content. They polish the deck, refine the talking points, and run through the narrative one more time. That is preparation for a presentation.
Senior leaders prepare for the conversation. They walk in already knowing what the room will challenge, where finance will get nervous, and which slide their boss will interrupt on. That is a learnable skill, and it used to take five to ten years of trial and error to build. AI tools now compress that learning curve into ten minutes of prep before any meeting. Here is how to use them.
1. Run the Stakeholder Prompt
The prompt I use before almost every big meeting is short, and I have refined it over hundreds of reps:
"Act like you are [my boss, head of finance, or the key stakeholder who always has a point of view]. What would you care about? Where would you push back? What questions would you ask?"
That single instruction forces you to step outside your own lens and anticipate what actually matters in the room. The output is rarely perfect on the first pass. It does not need to be. What you are looking for is a list of angles you would not have come up with on your own, sorted by how likely they are to come up.
The point of this prompt is to pressure-test your thinking, not to replace it. Perception is shaped in small moments. How you frame a decision. How you handle a question. How prepared you feel when the senior person in the room says, "Hold on, I want to push on this."
Run the prompt, read the output, and write down the three angles you find most uncomfortable. Those are the ones you need a clear answer for.
2. Use a Simple Prep Structure
Once you have your stakeholder lens, structure your prep in this exact order. The order matters more than the polish.
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Your recommendation. Start here. What do you want to happen? One sentence.
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Your two to three supporting points. Why should this be the direction? Keep each one to a single line.
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Your anticipated pushback. Write out the top three questions you expect. Make them specific.
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Your responses. Concise, clear, confident. No softeners.
Here is what this looks like in practice. Say you are walking into a meeting to pitch a new marketing budget.
Most people walk in thinking, "I need to walk them through what we want to do." The thinking at the next level shifts:
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What is the decision I am actually asking for?
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Where is this idea vulnerable?
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What will finance question?
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What will my boss challenge?
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Where could this fall apart?
When I run the prompt, I am listening for three things:
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Where is my logic not tight enough?
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What risks am I not addressing upfront?
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What is unclear or too long-winded?
Then I adjust. I tighten the narrative. I bring the recommendation forward. I address the risk before it gets raised. Done well, this single prep loop changes how the room experiences you. You stop sounding like someone presenting and start sounding like someone deciding.
3. Anchor the Recommendation With a Short Story
Once your logic is tight and your pushback is prepared, the move that takes any pitch from competent to memorable is anchoring your recommendation in one specific, 30-second story.
Humans are wired for narrative. We forget bullet points within hours. We carry stories for years. The recommendations that travel out of the room and into the next conversation are almost always the ones paired with a concrete moment: a customer who said a specific thing, a team member who ran into a specific wall, a single data point with a name behind it.
When I bring a strategic recommendation to my CEO, I almost always pair it with one short story before the data. "Last month a mom in San Diego told our retail partner she switched to us because she could not figure out the competitor's fold in the parking lot." That one sentence does more work than three slides of research. It is concrete, repeatable, and human. By the time my CEO walks into his next meeting, the story is what travels with him, and the recommendation rides along.
Strong communicators do not use stories to entertain. They use them strategically. One tight story is what makes the headline stick.
The Bottom Line
The professionals who get promoted faster are the ones who walk into rooms already three steps ahead of the conversation. AI tools make that level of preparation accessible to anyone willing to do ten minutes of prep before the meeting starts.
Run the stakeholder prompt. Use the four-step prep structure. Anchor the recommendation in one short, specific story. Do this for the next three meetings on your calendar and watch how differently senior leaders respond to you.
