AI Can’t Fix a Bad Communicator
And most leaders are bad communicators. Here’s how to actually fix that — with or without AI.
Real John here.. Hey all, happy Saturday! This week, I chat about communication, not TCP/IP, MCP, or some other network protocol, but actual human communication. It becomes the most challenging part of a job for any employee not just managers. With AI, we have changed the way we communicate and we have lost some of the nuance of human interactions. We have lost the art of communication. We have lost our kindness, empathy, and attention to who our audience is. We seek attention over understanding. We feel differently and don’t know why. We can still use AI to help us but we need to always remember we are human and the humans we are communicating with have their own filters, experiences, and we need to lead with empathy, understanding, and not just facts and succinct messages. 10 of Hearts - if you know you know. Let’s get into it.
I’ve sat in rooms with brilliant engineers who couldn’t explain what they built to save their lives. I’ve watched CTOs lose their teams not because of bad strategy, but because nobody knew what the strategy was. I’ve been that guy — confident I communicated clearly, only to find out my team heard something completely different.
Communication is the job. Not coding. Not architecting. Not roadmapping. If you’re in a leadership role, communication is your primary deliverable. And most of us are terrible at it.
Now AI is in the mix. And everyone’s excited about it — summarize this, draft that, turn my bullet points into a beautiful email. Cool. But here’s the hard truth: AI amplifies what’s already there. If your communication is unclear, vague, and politically hedged before you hit “generate,” it comes out the other end polished, verbose, and still unclear. Just with better grammar.
So before we talk about how AI can help, let’s fix the foundation.
The Actual Problems
Most leadership communication fails in one of three ways:
1. You bury the point. You spend three paragraphs on context before saying what you actually need. Reverse it. Lead with the decision, the ask, or the result. Context comes second.
2. You communicate to feel heard, not to be understood. This is the meeting problem. You talk. People nod. Nothing changes. The goal of communication is a shared understanding that leads to action — not a feeling of having said the thing.
3. You avoid the hard message. You soften, qualify, and hedge until the message is unrecognizable. “We might want to consider potentially exploring...” just means “we’re doing this.” Say that.
Where AI Actually Helps
Once you’ve got those fundamentals down, here’s where AI earns its seat at the table:
Draft the hard message first, then use AI to gut-check it. Write your message. Then paste it into Claude or ChatGPT and ask: “What will someone who disagrees with this hear?” That’s your pre-mortem. You’ll catch the landmines before they go off.
Use AI to translate between audiences. I regularly write something for an engineering team and then ask AI to reframe it for an executive audience — same message, different frame. What used to take 30 minutes of re-writing takes 5. The thinking is mine. The translation is AI’s.
Kill the fluff in your async communication. Slack messages. Status updates. Emails. Drop your draft into Claude and say: “Make this shorter and direct. Remove anything that doesn’t add information.” You will be shocked at how much nothing you were sending.
Meeting prep — for real this time. Before any significant meeting, I write a one-paragraph brief: what decision needs to be made, what information is already known, what I need from this group. AI helps me sharpen that brief so I walk in with clarity instead of vibes. Shorter meetings. Better outcomes.
Build a communication template library. Performance feedback, project status, escalation to leadership, team announcements — these are recurring communication patterns. Build a template for each, refine it with AI, and use it consistently. Your team will know what to expect, and you’ll spend less time staring at a blank page.
The One Thing That Doesn’t Change
None of this works if you don’t know what you’re trying to say. AI can sharpen your message. It cannot find your message for you. That’s still your job.
The leaders I respect most aren’t the ones with the best vocabulary or the smoothest delivery. They’re the ones who are clear about what they think, honest about what they don’t know, and consistent enough that people trust what they hear.
Thirty years in this industry taught me that the technical problems are rarely what kill a product, a team, or a company. It’s usually a communication breakdown somewhere — a decision that never got made explicit, a direction that got lost in translation, a hard conversation that never happened.
AI didn’t create that problem. But it can absolutely help you stop repeating it.
Now go communicate something clearly. And then go build something amazing.
John Mann — Startups and Code LLC | Building, leading, and occasionally ranting at startupsandcode.com