10 AI Prompts You Should Be Using Every Week

The practical prompt guide for Canadian solopreneurs, coaches, creators, service providers, and small business owners who are tired of staring at blank pages and want to reclaim their week.

She had ChatGPT open every single day.But she was asking it the same three things on repeat. A caption here. An email there. The occasional brainstorm when she was stuck. She thought she was using AI. She was barely touching it.

When I walked her through what else was possible — not theory, just ten specific prompts tied to the ten tasks that were quietly draining her week — she went quiet for a moment and then said: “I have been leaving hours on the table every single week.”

She had been. Most people are.

This guide is about closing that gap. Not with more tools. Not with complicated systems. Just ten prompts — one for each of the recurring tasks that take longer than they should and drain more energy than they deserve.

Before You Start: The One Thing That Makes Prompts Work

A prompt is only as good as the context you give it.

The single most common reason AI output is generic, unhelpful, or sounds nothing like you is not the tool. It is the input. Vague in, vague out. Specific in, specific out.

Every prompt in this guide follows the same structure:

• Task — what you need done
• Context — the specific situation, not a general description
• Tone — how you normally communicate
• Constraint — length, format, or specific requirements

When you give AI all four, the output is almost always usable on the first pass. When you skip context, you spend twenty minutes editing something that still does not sound right.

With that said — here are the ten.

Prompt #1: The Monday Brain Dump

The problem it solves: You start the week with everything in your head and no clarity on what actually matters. You end up reactive — handling whatever shows up first instead of moving your business forward.

The prompt:

Here is everything on my plate this week:
[list every task, project, commitment, and worry — unfiltered]

I run a [type of business]. My biggest current priority is [one sentence].

Help me:
1. Identify the three tasks that will move my business forward most this week
2. Suggest what I can deprioritize, delegate, or drop entirely
3. Flag anything that looks like it should not be on my plate at all

What good output looks like: A ranked list of three priorities with a brief reason for each, plus a short list of tasks to reconsider — with honest observations like “this appears to be urgent but not important” or “this has been on the list three weeks running — is it actually getting done?”

Real example: A Calgary-based life coach used this every Monday for six weeks. Her observation: “It kept flagging that I was spending three hours a week on admin that had nothing to do with client work or getting new clients. I hired a virtual assistant for four hours a week. Best $200 I spend every month.”

• Pro tip: Save your brain dump from the previous week and paste it in alongside the current one. Ask AI to identify patterns. What keeps showing up that never gets done? That is your real bottleneck.

Prompt #2: The Email You Keep Avoiding

The problem it solves: There is always an email sitting in your drafts — or worse, sitting in your head — that you cannot quite bring yourself to write. The awkward ask. The difficult update. The boundary-setting message you have been putting off for two weeks.

The prompt:

I need to write an email to [person or role — e.g. "a client who 
hasn't paid their invoice in 45 days"].

Context: [2-3 sentences explaining the situation — what happened, 
what you need, any relevant history]

My tone is usually [warm and direct / professional but friendly / 
firm but fair].

I need them to [specific action — pay by Friday / schedule a call / 
acknowledge the issue].

Please draft this so it sounds like a real person wrote it, not a 
template. Keep it under 200 words.

What good output looks like: A message that gets to the point without being cold, addresses the situation specifically, and makes the next step clear — without sounding like it came from a collections agency or a passive-aggressive HR department.

Real example: A freelance web designer had three unpaid invoices from the same client. She had been avoiding the follow-up for two weeks because she wanted to preserve the relationship. She used this prompt, reviewed the draft, added one personal sentence, and sent it within five minutes. Invoice paid within 48 hours. Relationship intact.

• Pro tip: For especially sensitive emails, run the draft back through AI with this follow-up: “Read this email as the recipient. What is their likely emotional reaction? What might they misinterpret? What would make them more likely to respond positively?” One extra step that saves a lot of backtracking.

Prompt #3: The Follow-Up That Never Gets Sent

The problem it solves: Most sales, most client relationships, and most opportunities are lost not in the first conversation but in the silence after. The follow-up you meant to send but did not because you were not sure what to say, how long to wait, or how to bring it up without sounding desperate.

The prompt:

I had a [call / meeting / conversation] with [name or role] 
about [topic] on [approximate date].

How it went: [one sentence — e.g. "They seemed interested but 
said they needed to think about budget" or "It ended 
inconclusively and they said they'd be in touch"]

It has been [number] days/weeks since I heard from them.

Draft a follow-up message that:
- Checks in genuinely without sounding desperate
- Adds a small piece of value or a relevant observation
- Makes it easy for them to respond either way
- Stays under 100 words

What good output looks like: A message that feels like it came from someone confident, not someone chasing. Short, specific, low-pressure — that gives the person an easy way to re-engage or politely close the loop.

When to use it: Three to five days after a proposal call that went quiet. One week after sending a quote with no response. Two weeks after any conversation that ended with “I will be in touch.”

• Pro tip: Ask AI for three versions — one warm, one direct, one that adds a specific piece of value relevant to their business. Pick the one that fits the relationship.

Prompt #4: The Caption You Have Explained a Hundred Times

The problem it solves: You have a service or product you have described so many times that you are on autopilot — and the autopilot version is flat, generic, and doing nothing for your visibility.

The prompt:

Write three caption options for [platform — Instagram / LinkedIn / 
Facebook] for my [product / service / offer]:

[Name of offer]: [one sentence description]
Price: [if relevant]
Who it is for: [specific audience]
The main benefit: [what changes for them]
My tone: [warm / direct / casual / professional]

Requirements:
- Each option under [150 / 200] words
- Different angles (one emotional, one practical, one story-driven)
- End each with a soft call to action
- No hashtag spam
- Sound like a real person, not a marketing brochure

What good output looks like: Three genuinely different options — not the same caption with synonyms swapped in. One that leads with emotion, one that leads with the practical outcome, one that opens with a story or observation. You pick the one that fits the moment or test all three over three weeks.

• Pro tip: Save the caption that performs best. Next time you promote the same offer, paste it in with this instruction: “Here is a caption I wrote previously that performed well: [paste it]. Write three new options inspired by this one but with fresh angles.”

Prompt #5: The Weekly Reflection

The problem it solves: Most business owners spend all their time doing and almost no time reviewing. Which means the same problems recur every week, the same opportunities get missed, and six months pass before you notice a pattern that was obvious from week three.

The prompt:

Here is a summary of my week in business:

What I worked on: [list]
What went well: [honest answer]
What did not go as planned: [honest answer]
What I avoided: [the thing you kept pushing to tomorrow]
Current energy level: [1-10 and why]

Questions I want you to answer:
1. What patterns do you notice across these areas?
2. What should I pay more attention to next week?
3. What am I avoiding and what might that be costing me?
4. What is one thing I could do differently next week that would 
   have the biggest impact?

What good output looks like: Observations that feel slightly uncomfortable — the kind you know are true but have been too busy to sit with. Not cheerleading. Not generic advice. Specific reflections based on what you actually shared.

When to do it: Friday afternoon or Sunday evening. Ten minutes. The ROI on this prompt compounds over time — the longer you do it, the more useful it becomes because patterns become visible across weeks.

Prompt #6: The Proposal Outline

The problem it solves: Every new inquiry requires a proposal. Every proposal starts from a blank page. Every blank page costs 60 to 90 minutes you do not have.

The prompt:

I need to write a proposal for a new client. Here are the details:

Client type: [e.g. small retail business, solopreneur coach, 
restaurant owner]
What they need: [specific project or service]
Their main concern: [price / timeline / quality / trust / 
past bad experience]
My approach: [how I would handle this — 2-3 sentences]
Investment: [your range or fixed price]
Timeline: [how long it takes]
What makes me different: [one honest sentence]

Please draft a proposal outline with:
- An opening that directly addresses their main concern
- A description of my approach and what they can expect
- Clear investment and timeline section
- A specific, low-pressure next step
- Professional but not stiff. Under 400 words.

What good output looks like: A proposal that leads with the client’s concern, not your credentials. Most proposals open with “About Us” when the client only cares about “Will this work for me?” This prompt flips that structure.

• Pro tip: After the first draft, follow up with: “Read this proposal as a skeptical client. What objections might they still have? What is missing? What feels unclear?” Address those before you send.

Prompt #7: The Client Update

The problem it solves: Clients who feel uninformed get anxious. Anxious clients micromanage, lose confidence, or quietly start looking elsewhere. A short, confident weekly update is one of the highest-ROI habits a service business can build — and it almost never gets done because it feels time-consuming.

The prompt:

I need to send a weekly update to [client name or type] 
about [project or ongoing service].

What happened this week: [your rough notes — point form is fine]
What is happening next week: [what you plan to do]
Any decisions they need to make: [yes/no — if yes, what]
Overall status: [on track / slight delay / ahead of schedule]

Write this as a professional but warm update. Clear, confident, 
no jargon. Under 200 words. End with one sentence that makes 
them feel like the project is in good hands.

What good output looks like: A message that takes thirty seconds to read and leaves the client feeling informed and reassured — not overwhelmed with detail or left with unanswered questions.

• Pro tip: Create a template for each ongoing client and save it. Update only the “what happened this week” section. Over time this becomes a two-minute task instead of a twenty-minute one.

Prompt #8: The Negative Review Response

The problem it solves: A negative review left unanswered does more damage than the review itself. A poorly written response — defensive, dismissive, or over-apologetic — makes it worse. A calm, specific, professional response can actually turn a negative into a trust signal for everyone else reading.

The prompt:

A customer left this review of my business:
[paste the review exactly as written]

My business type: [what you do]
What actually happened (my side): [honest, brief — 2 sentences]

Please draft a response that:
- Acknowledges their experience without being defensive
- Shows I take feedback seriously
- Corrects any factual errors calmly, if applicable
- Invites them to continue the conversation offline
- Stays under 100 words
- Does not sound like a legal department wrote it

Important: Always review this output carefully before posting. Add one specific detail that shows you actually remember the situation. Generic review responses are easy to spot and make things worse.

What to never do: Do not respond to a negative review when you are angry. Write the angry version in a document, close it, use this prompt, then decide which response you actually want to send.

Prompt #9: The Content Repurpose

The problem it solves: You write a newsletter, a blog post, or a LinkedIn article. It gets read once and disappears. Meanwhile you are starting from scratch every time you need a caption, a post, or a social update — when the raw material was already there.

The prompt:

Here is a piece of content I wrote this week:
[paste your full newsletter, blog section, or article]

Please create:
1. One LinkedIn post (150-200 words, punchy, first-person, 
   conversational, ends with a question or insight)
2. One Facebook post (same content, warmer tone, 
   slightly longer, links are fine)
3. Three short captions (under 80 words each, 
   different angles from the original)
4. Five one-liner insights I could post as standalone 
   thoughts this week
5. One email subject line that would make someone 
   want to open this article

Keep everything sounding like the original — same voice, 
same specific details, no generic statements.

What good output looks like: Five different pieces of content that all feel connected to the original but work independently on their respective platforms. Not the same paragraph reformatted — genuinely different angles on the same core idea.

• Pro tip: Run this every Monday after sending your newsletter. In fifteen minutes you have a week of social content. Schedule it. Show up consistently without spending your week writing from scratch.

Prompt #10: The Decision Unsticker

The problem it solves: Every founder has a decision they are circling. Should I raise my prices? Should I drop this service line? Should I hire help or stay lean? Should I pivot or push through? These decisions sit in the background consuming mental energy for weeks — sometimes months — because there is no clean framework to resolve them.

The prompt:

I am trying to decide between [Option A] and [Option B].

My situation:
- Business type: [what you do]
- Current stage: [just starting / growing / plateauing / 
  pivoting]
- Main constraint: [time / money / energy / confidence]
- What I know for certain: [what the data or experience tells you]
- What I am unsure about: [the honest uncertainty]
- What I am afraid of: [yes, say it — it matters]

Please help me think through this by:
1. Identifying what I actually need to know to make this decision 
   (not more research — the one key factor)
2. Playing devil's advocate for the option I seem to be leaning away from
3. Asking me the one question I am probably avoiding
4. Giving me a clear recommendation based on what I have shared — 
   not a "it depends" answer

What good output looks like: Not permission to do what you already wanted to do. A genuine challenge to your assumptions, a question you had not considered, and a specific recommendation — even if uncomfortable.

Important note: AI does not know your full situation. Its recommendation is a thinking tool, not a verdict. But asking it to make a call forces the analysis to be concrete — and concrete is more useful than “here are the pros and cons of each.”

How to Build These Into Your Week

Here is a simple weekly rhythm using these ten prompts:

• Monday (15 minutes) Prompt #1: Brain Dump — set your week with intention
• Tuesday/Wednesday (as needed) Prompt #2: Email You Keep Avoiding Prompt #3: Follow-Up That Never Gets Sent Prompt #6: Proposal Outline (when a new inquiry comes in)
• Thursday (20 minutes) Prompt #9: Content Repurpose — turn this week’s content into next week’s social posts Prompt #4: Caption — for anything you need to post this week
• Friday (10 minutes) Prompt #5: Weekly Reflection — five minutes that compound over time Prompt #7: Client Updates — send before end of day
• Ongoing (when needed) Prompt #8: Negative Review Response — never sit on these Prompt #10: Decision Unsticker — when you notice you are circling

Total time: roughly 45-60 minutes a week. The return on that investment compounds every week you do it consistently.

The Prompt Upgrade: Make Them Sound Like You Every Time

Every prompt above works better with one addition — a voice instruction.

Before you run any prompt, add this line:

"My writing style: [two or three sentences describing how you communicate. E.g. 'I write in short paragraphs, use direct language, occasionally say my friend, avoid corporate jargon, and always address the reader as a peer not a customer.']"

Save this voice description somewhere accessible. Paste it into any prompt. Your output will sound like you wrote it — because you told AI exactly what that means.

This is the single upgrade that makes the biggest difference. People stop asking “does this sound like me?” and start asking “how do I publish this faster?”

What These Prompts Will Not Do

With all hosnesty, here me out.

These prompts will not replace your judgment. They will not maintain a relationship for you. They will not know the history you have with a specific client, the nuance of a local market situation, or the instinct built from years of running your business.

What they will do is handle the mechanical, repetitive, stare-at-a-blank-page parts of your week so you have more energy left for the parts that actually require you.

That is the exchange. It is worth it.

The Next Step

Pick two prompts from this list. The one that solves your biggest current frustration and the one that saves you the most time.

Use them consistently for two weeks. Adjust the prompt when the output is not quite right — one added sentence of context usually fixes it. Save the version that produces the best results.

After two weeks, add one more.

That is how a list becomes a system. And a system is what actually changes how your week feels.

Download: 10 Weekly AI Prompts (One Page)

All ten prompts formatted, labeled, and ready to copy — in a single branded PDF you can keep on your desk or save to your phone.

Drop PROMPTS in the comments on LinkedIn and I will send it directly.

Go Deeper With WilGlobo Tools

• AI Task Filter (Free) Before you use any prompt, know which tasks in your business are worth automating and which ones should stay human. Start here.

• SME AI Playbook 30+ more prompts built specifically for Canadian small business owners — across client communication, content creation, operations, and planning. Every use case has a ready-to-use prompt and a real example.
• AI Growth Advisor (Free) Talk through which prompts fit your specific situation before you start building anything.
• Founder Decision OS For founders who need a structured system for the big decisions — not just the day-to-day tasks.
• Digital Equity Hub Hands-on digital services for small business owners who need help beyond prompts.
• Book a Discovery Call 30 minutes. No pitch. Just a real conversation about what would actually help your business right now.

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Wilton Otto is the founder of WilGlobo Digital Solutions, helping Canadian small business owners, solopreneurs, coaches, and newcomer entrepreneurs use AI practically without the hype. He publishes Digital Equity Notes every Monday.

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