Communicating Effectively With Management Via ChatGPT

Dr Stuart Woolley
Published in
6 min readApr 1, 2023


Sometimes it’s nice to speak to someone in their own language.

Photo by Karolina Grabowska on Pexels

It is often said that one should continuously adapt the way in which one communicates depending upon to whom you are communicating in order to achieve maximum effect.

Unfortunately, despite the plethora of eye-wateringly expensive and attractively named management courses, journals, and weekend spar hotel based seminars that are increasingly available, they don’t seem to have cottoned on to this fact and continue trotting out the same tired overbearing doctrine of years gone by.

We however, the progressive software engineers toiling away in the Grand Game of Software Engineering, have learned to understand their occult management buzzwords and have developed a unique immunity to its torpor inducing effects.

We’ve even managed, on occasion, to distil some meaning from the banal and often obfuscated bullshit that sometimes flows steadily or other times falls out in collective lumps from the various corporate ‘channels’.

But we could of course do without this nonsense to be perfectly honest. Therefore, on occasion, in our semi passive-aggressive resistance to this it’s actually quite fun¹ to return the favour to management types and speak in their language — to see if they actually understand what’s being communicated in their mixed up tongue.

Let me illustrate my thoughts with some examples.

Recommended Conversation Approaches

A Boring Job with Terrible Technology

I’m desperately unhappy in my current role as it’s boring, the technology is cheap and nasty as the project manager won’t pay for what I need, and upper management ignores everything I say.

My first thought is to complain vociferously to the project manager, after complaining on Teams / Slack / Skype² to the rest of the development team, but I catch myself and realise that they’ll be oblivious to any technical arguments after seeing them trying to operate the company microwave.

ChatGPT to the rescue, let’s rephrase my initial thoughts “in a polite businesslike way so that a project



Dr Stuart Woolley

Worries about the future. Way too involved with software. Likes coffee, maths, and . Would prefer to be in academia. SpaceX, Twitter, and Overwatch fan.