Automate The Why
Show Them What You See
People assume that everyone knows what they know. This is why there is often a disconnect between stakeholders and teams on a project’s fundamental purpose.
Without this information the team is a ship without a rudder. The engine is powerful, and it looks like progress is happening. But the direction is haphazard and heavily dependent on the ocean’s mood.
Ideally the stakeholders communicate the core problem to be solved widely. But chances are they’ll forget or assume that everyone already knows.
Even better is to foster a culture of safety to ask:
What are we trying to accomplish here?
Easier said than done. Asking reveals two things:
The asker doesn’t know
They can’t figure it out
The asker is risking that these are offenses. They might be.
The antidote: encouragement and gratitude.
The benefit of asking is that it gets everyone’s gears turning on how the problem could be solved. A cocktail of expertise that brews innovation.
The goal won’t change.
But there’s many paths forward.
100% Typo Guarantee - This message was written without any AI assistance. All yours imperfectly truly. Therefore, I can virtually guarantee there’s a double word or misspelling somewhere. Happy Hunting!


I appreciate the note at the bottom of your article about writing without AI assistance. I've been receiving more AI generated responses at work recently and I really don't know how to react? Yesterday a marketing person we are working with sent a 10 question survey to our team to get feedback on our product. It felt ChatGPT-y so I put it into a detector and it came out as a positive. I spent time writing each response and in the email back I mentioned that it took me about 30 minutes to write my answers so it was clear that I didn't use AI myself.
I'm fine with using AI to get through pointless hoops to save time appropriately, I do it myself. But I'm less motivated to work with people that use AI heavily because there's a mismatch in effort. Anyways, here's to an AI free newsletter! I know you'll get more out of the experience of writing yourself and your readers will too. Thanks for sharing your thoughts.
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To your topic, I tend to ask a lot of questions when starting a project. Usually that helps me figure out the story of what we are building, especially when asking someone who is receptive to the curiosity. I've found that others don't respond well to the probing and resort to shorter answers like, "that's how we do it," or "just get it done." When I work with someone like that I tend to stop asking questions. I just say I'll get the job done. If they want yes men, that's what they'll get.