Hi there,

This week I'm continuing my Leadership and AI series, focusing on one of the trickiest parts of being a manager – influencing stakeholders and managing up.

You know that moment when you're about to walk into a meeting with a senior stakeholder, and there's that little voice in your head saying, "I really hope this lands." You've done your preparation, you've got your presentation sorted, but somehow you're still not sure if they'll actually connect with what you're saying.

Well, I've been exploring how AI can help you figure out exactly what to do to make sure you connect every time.

Most managers I work with bump into this challenge regularly. Despite all the preparation and good looking slides, your message just doesn't seem to hit the mark. And when that happens with the people who really matter, especially when you're trying to influence people outside your immediate team, it's incredibly frustrating.

But what if there was a way to decode how different people prefer to receive information, and then tailor your approach accordingly? That's exactly what I'm exploring this week.

Here’s the thing. It's usually not your content that’s the problem. It’s your delivery.

You’re speaking your language, not theirs.

But here's the good news. You don’t need a psychology degree or hours of prep to get better at this. In fact, with a bit of help from AI, you can do it in five minutes.

Here are two things you can try straight away:

1. Ask AI to help you spot your blind spots.

Pop this into ChatGPT or Claude:

"Ask me 8 questions about how I typically communicate at work. Based on my answers, give me a simple summary of my style and what I might miss when talking to others."

This gives you a snapshot of how you show up and where your message might not be landing.

2. Scan your stakeholder’s last few emails or meeting moments.

Ask yourself, do they start with small talk or jump straight into business? Do they want big-picture thinking or bullet points and deadlines? Noticing their patterns gives you insight into how to shape your message so they hear it. Even quicker copy a few of their emails into your AI tool and ask it see what it patterns it spots that might reflect the communication style of the writer.

These aren’t just theory.

I use these techniques myself and teach them to clients. And when you combine them with a little AI support, you get sharper insight and better results, fast.

In this week’s video, I walk through a practical way to get help from AI to:

• Understand your own communication style
• Decode the subtle signs in how your stakeholder thinks and talks
• Help you tailor your message so it really hits home

This is the kind of work that can shift how you're seen. It builds trust, gets faster buy-in, and helps you avoid those “why didn’t that land” moments.

If you’re someone who wants to feel more confident, especially when it matters most, I think this will really help.

If you have any comments or questions on this just hit reply, I'm here!

Have a great week.

Take care, Helen

​ Want to work together? ​Manager OS Course - Reclaim Your Time & Accelerate Your Career with Manager OS - A Proven System to Help Managers Lead with Confidence & Ease Work with me 1:1 - Book a coaching session​ ​The Leadership Vault: Your private access to every issue of my Newsletter. Every strategy, tip, and lesson shared in past newsletters—now available in one place. Stay ahead, stay informed, and lead smarter. ​Visit my website to find out more. ​

​