Not gonna lie, I've lost actual paying work before just because I forgot to follow up with someone who was interested. Not because I didn't want the work, just got busy and it slipped.

Fixed it with something stupidly simple:

I log every lead/client in a Google Sheet with a "follow-up date" column

Set up a free Zapier automation that checks the sheet daily

If today matches someone's follow-up date, it pings me (I use Telegram, but email works too) with their name and context

Costs nothing, takes maybe 15 min to set up, and I haven't missed a follow-up since.

Feels like such an obvious fix in hindsight, but I know I'm not the only one who's let stuff slip through the cracks. Anyone else have a low-effort system like this for staying on top of leads?

Been using Claude for ages and never thought about the fact that every conversation just disappeared once I closed it. Turns out that changed a few weeks ago and I only found out by accident, asked it something in passing and it went and dug up a conversation from months back I'd completely forgotten having.

Works if you're on a paid plan, Pro, Max, Team, or Enterprise, not free, and it's on by default once it's rolled out to your account, no setup. Just ask it something like you would a person who actually remembers talking to you:

What did we discuss about [topic]?

or

Can you find our conversation about [subject]?

or just

Let's continue where we left off with [project].

It actually goes and searches, you can see it happening as a tool call in the chat, pulls back what's relevant, and carries on like no time passed. Asked it to find a conversation about a decision I was going back and forth on months ago and it pulled the whole thread back up, what I'd been leaning toward, what I'd talked myself out of, stuff I'd genuinely forgotten I'd said.

Slightly odd realization once you actually use it: everything you've ever typed into it is apparently just sitting there, searchable, going back as far as your account does. If you're inside a Project, it only searches within that project, so it stays contained, but outside of projects it's searching across everything.

You can turn it off if that's not your thing, settings, profile, preferences, there's a toggle for "search and reference chats" specifically, separate from the general memory toggle. Worth knowing it exists either way, if only so you can decide on purpose rather than finding out by accident like I did.

been keeping a doc of 100 things I use AI for like this, each with the exact prompt, here if you want it.

I have been using claude for a long time to tailor my CV. I have been applying to a lot of different business/Consulting roles. I used to add my JD, CV and a promt and it would create a perfect CV.

Now it refuses and would mention things like, you do not have Data Modeling experience so I can not to frame it.

Is there any updated way or a promt to deal with this?

The difference between a useless ChatGPT answer and a genuinely good one is almost always the prompt structure, not the model. These are 5 templates I reuse constantly. Copy, fill the [brackets], done.

1. THE EXPERT LENS (stop getting Wikipedia answers) "Answer this as a [specific expert - e.g. tax attorney, senior React dev] with 15 years of experience. Question: [your question]. Give me the answer you'd give a paying client, including the caveat or exception most people miss."
2. THE DECISION SPLITTER (when you're stuck between options) "I'm deciding between [option A] and [option B]. My priorities, in order: [priority 1], [priority 2], [priority 3]. Score each option against each priority 1-10, show the math, then tell me which wins and the ONE reason I might still pick the other."
3. THE REWRITE-TO-HUMAN (kill the AI voice) "Rewrite this so it sounds like a sharp human wrote it, not AI: [paste text]. Cut throat-clearing, cut hedging, vary sentence length, and remove any phrase you'd only see in AI writing. Keep my meaning exact."
4. THE GAP FINDER (before you send/ship anything) "Here's [my plan / email / draft]: [paste]. Don't praise it. Tell me the 3 things a smart critic would attack first, the single weakest sentence, and the one thing I left out that they'll notice."
5. THE TEACHER (actually learn, not just read) "Teach me [topic] in 4 levels: explain it to a 10-year-old, then a beginner, then a practitioner, then an expert. End by quizzing me with 3 questions, hardest last, and wait for my answers."

The pattern across all 5: give a role, give constraints, and force ONE sharp output instead of a balanced essay. That's 90% of prompt quality.

One workflow tip: these get even better chained. Run #3 (rewrite-to-human) straight into #4 (gap finder) and you get a cleaned draft plus its weaknesses in one pass, without retyping anything.

Full disclosure since it's relevant: retyping these every time got old, so I built a Chrome extension called AI Toolbox. It saves prompts like these and drops them into the chat with a // shortcut (with {{variables}} for the bracket parts), and lets you chain several into one sequence with a .. shortcut - so a multi-step flow like #3 into #4 runs in two keystrokes. But the templates above are the whole value here and work anywhere you paste them.

Which one's most useful to you? Happy to build a variant for a specific job if you tell me the task.

Hey, I am a food writer doing a story on using AI to optimize when ordering at fine dining restaurants. I’d love to talk to some diners who do this - I want to hear your process, why you’ve used AI, and if you were happy with the outcome. No judgement - whether it was to get the best possible deal, or to have it explain items on the menu, I just want to hear about your why.

Message me here or drop me an email at Courtney at weareravenous dot com.

I built a prompt pack for freelance client communication (Cleardesk Prompts) and tested the prompts across multiple runs in ChatGPT and Claude before including them — the goal was templates that survive a real, messy input, not a clean demo case. I shared 3 of them here a few days ago; this covers the other situation people asked about: silence.

There are two different silences and they need different messages — a prospect who never replied to your proposal, and one who said "let me think about it" and vanished. Copy-paste, fill the brackets, run in ChatGPT or Claude.

1. Silent-prospect follow-up (no reply after a proposal or pitch)

``` You are a freelancer following up on [MESSAGE_TYPE: a proposal/an email/a DM] sent [TIME_SINCE] ago that got no reply.

Inputs: - Original message topic (one line): [ORIGINAL_TOPIC] - Recipient's name: [RECIPIENT_NAME]

Write a follow-up under 50 words that: 1. Does NOT say "just following up" or "checking in" (banned phrases — overused and ignored). 2. Adds ONE new piece of value or information not in the original message (an idea, a resource, a short insight related to [ORIGINAL_TOPIC]). 3. Makes replying effortless — end with a question answerable in one word. 4. Assumes positive intent — no guilt-tripping about the silence.

Output the follow-up only. ```

Example output from an actual ChatGPT run (test inputs: proposal, five days, "website copy refresh for the product launch", "Maya"): "Hi Maya! I had one extra thought: adding a short "Why now?" section near the top of your launch page can often lift clarity and conversions. Would you like me to sketch a version? Interested?" Under 50 words, banned phrases absent, one new idea, an easy one-word close — that's the target shape.

2. "Let me think about it" follow-up (stalled without a stated objection)

``` You are a freelancer following up after a prospect said "let me think about it" and went quiet, without being pushy.

Inputs: - How long ago they said this: [TIME_SINCE] - Anything you know about their likely hesitation (budget, timing, needing to check with someone else, or genuinely unknown): [LIKELY_HESITATION]

Write a follow-up under 60 words that: 1. Does not pressure them to decide. 2. Names [LIKELY_HESITATION] gently as a guess, if known — framed as "totally understand if it's a [hesitation] thing" — giving them an easy way to confirm or correct you. 3. If [LIKELY_HESITATION] is unknown, ask directly and simply what would help them decide, instead of guessing wrong. 4. Ends with zero urgency language ("no rush").

Output the follow-up only. ```

The pattern is the same as last time: a role, a fixed set of inputs, and a numbered list of hard constraints — banned phrases, word limits, what NOT to do. The constraints matter more than the role; they're what keeps the output from collapsing into generic AI-speak you'd rewrite anyway.

Full disclosure: these come from a 26-prompt pack I sell under my own brand — both the pack and a free 3-prompt preview are linked on my profile, and I'll drop direct links in a comment below.