One of the biggest lessons I’ve learned at Abby AI is that AI gets a lot more useful when you stop treating every prompt like a fresh start.

Ben, our CEO and founder, and I use AI extensively every day to help us build almost every part of the business. Go-to-market strategy. Sales messaging. Customer conversations. Design. Meeting prep. Follow-up. Branding. Positioning. Investor strategy. Content. Planning. Dev roadmap. OK- we use it for EVERYTHING. It the messy thrill of building something real.

And here is what I keep learning:

AI is only as useful as the context you give it.

If I ask, “What should we do?” with no backstory, I get something smart and polished and mostly generic.

But if I give it the actual mess. What we know, what we are trying to prove, who we are talking to, what matters to the customer, what we are assuming, what we are worried about, and what we absolutely do not want to become… the quality of the thinking and the output changes. Dramatically.

It is like inviting a really smart person into the room with no history, no agenda, no stakes, and no idea what happened before they arrived. And asking their advice. They can give it, it may even sound impressive, but it can only be superficially relevant.

Remote workers live in this problem all day.

Our context is scattered across Slack threads, Zoom calls, emails, docs, notes, voice memos, half-finished thoughts, and things we swear we will remember later.

Then we ask AI for help and wonder why the answer feels flat.

Of course it does.

We made it guess the room.

So before you ask AI to solve, decide, write, or recommend, try this simple formula:

Context first. Then clarity. Then output.

Start with a brain dump:

“Here is the situation. Here is who is involved. Here is what I know. Here is what I believe. Here is what I am assuming. Here is what I am worried about. Here is what I do not want. Here is what I still do not know.” 

Next copy and paste any relevant contextual info, meeting notes, screenshots, documents, etc. 

Then ask AI to organize this info before it gives advice:

“Separate what I gave you into facts, observations, assumptions, hypotheses, open questions, and decisions already made.”

That prompt alone can be humbling.

Sometimes the “fact” driving your decision is really just an assumption wearing a nice blazer.

Then ask:

“What context is missing that would change your recommendation?”

Now you are not just using AI to produce more work.

You are using it to build a clearer thinking environment.

For remote professionals, that is the real value. AI can help gather the fragments, sort the noise, and show you the actual problem hiding underneath all the activity.

You still make the call.

You still bring the judgment, experience, taste, values, and human read of the situation.

AI just helps you stop making decisions from the junk drawer of your brain.

And honestly?

That drawer needed help.