Priya R.Director of Development · Portland nonprofit
Prepared by
Lantern PlanSample plan
01 — A note to start
Thank you for trusting us with the honest version.
You shared where things get stuck. We read everything carefully. What follows is a plan written for you — not a template — and yours to keep whether you decide to continue or not.
We don't sell software, and we don't make anything on the side from any of the tools we recommend. That means we only suggest things we'd use ourselves, and only when the math clearly works for you. If a recommendation below doesn't feel right, say so — we'll happily rework it.
Everything here is a suggestion, not a commitment. You can do all of it, some of it, or none of it.
02 — Your world today
Here's what we understood from your answers.
Not problems — just observations. If we got anything wrong, tell us and we'll fix it before going further.
You're the director of development at a Portland arts nonprofit with a team of three. Fundraising, events, the board, donor stewardship — it all flows through you. Your husband jokes that you work two full-time jobs and call it one.
Your inbox is the boss. On a good morning there are 180 unread; on a bad one, over 400. You triage by guilt. Important donor replies sit next to calendar invites next to vendor quotes.
Board decks get built the night before. The annual report took forty hours of evenings last spring. Thank-you letters to donors are personal — which is why they keep falling behind.
You're on Google Workspace (nonprofit discount), pay for ChatGPT but “don't really use it,” keep files in Dropbox, and sign everything in DocuSign. Calendar is a scheduling nightmare — you spend a meaningful chunk of each week arranging donor meetings.
You're good at this job. The donors love you. The board trusts you. The question isn't whether you can keep doing it — it's whether there's a version where the job stops bleeding into your evenings.
03 — How we picked these tools
Only tools we'd use ourselves. No affiliate deals.
Everything below passed three tests: the company is well-funded and unlikely to disappear in the next year; the security posture is enterprise-grade (SOC 2, encryption, clear data handling); and the capability genuinely fits what you told us — not a generic “AI for work” pitch.
We looked at twenty-plus products in your space. What's here is the short list that survived. The next section lists a few well-known names we considered and decided against, and why.
04 — What we think could help
A short list of tools worth your attention.
Two groups. Foundation tools are the plumbing — email, calendar, files. AI tools are where the biggest time savings come from. Each has a plain-English explanation of what it is and why we're suggesting it for you specifically.
Foundation 3 items
Superhuman
~$30 / mo · sits on top of your Gmail
What it is: A faster email app that uses your existing Gmail underneath. It writes replies in your voice, summarizes long threads in one line, and sorts your inbox so the ten things that matter rise to the top and the rest goes quiet.
Why it helps you: You said the inbox is the boss, that you triage by guilt, that 400 unread by Friday is normal. Superhuman replaces that grind with a 15-minute morning pass. It drafts responses in your tone so the donor thank-yous and board follow-ups stop sitting in “I'll write that tomorrow.” SOC II compliant — safe for donor communications.
It won't organize your Dropbox or help with long-form writing like board decks. It's email only — but email is eating the most hours right now.
Getting started — step by step
Request access. On your Mac, open Chrome and go to superhuman.com. Click Get Superhuman. Enter your work email (the Google Workspace one you use for donor communications). There may be a short waitlist — most people get access within a day or two. You'll get an email when you're in.
Install the desktop app. Once approved, the welcome email has a download link. Click it, download the installer, and drag the Superhuman icon into your Applications folder. Open it. It will ask you to sign in with your Google account — choose the work Gmail account. A permissions screen will appear asking Superhuman to read and send email on your behalf. This is normal and necessary — it's how the app sits on top of Gmail. Click Allow.
Complete the onboarding. Superhuman walks you through a short tutorial the first time you open it. Pay attention to three shortcuts — these are the ones you'll use constantly:
E — archive and move to the next message (this is how you clear the inbox)
H — set a reminder to come back to this email later (so you can clear it now without forgetting)
Cmd + K (on Mac) — the command palette, which lets you do anything by typing what you want
Train it on your voice. After the tutorial, go to Settings (click the gear icon in the bottom-left) → AI → Write in my voice. Turn this on. Superhuman will analyze your sent emails to learn how you write. Give it about an hour to process. After that, when you hit Reply, it will draft a response that sounds like you — not like a robot.
Set up VIP senders. In Settings → Priority, add the email addresses of your top ten donors, your board chair, and your ED. These people's emails will always appear at the top of your inbox, even on a 400-message morning.
Install on your iPhone. Open the App Store. Search Superhuman. Tap Get. Sign in with the same Google account. Your inbox, VIPs, and reminders all sync automatically.
Test it right now. Open Superhuman on your Mac. Find a donor email that needs a reply. Hit R to reply. Look at the draft it wrote for you. If it sounds close to your voice, edit the parts that need adjusting and send. If it sounds off, give it a few more days — the voice matching improves with every email you send.
Don't try to learn every shortcut. E, H, and Cmd+K are the only three that matter for the first week. Everything else you can pick up as you go.
Reclaim.ai
Free tier, or ~$10 / mo for Starter
What it is: A calendar assistant that shares a booking link with donors (they pick a time, the meeting appears on both calendars), defends your focus blocks for writing, and reshuffles your week when a board chair reschedules.
Why it helps you: The 5–8 emails per donor coffee collapse to one link. And those hour-and-a-half writing blocks for the annual report? Reclaim puts them on the calendar on purpose, so they stop getting eaten by drop-in meetings. We'd set up two booking links: one for donors (flexible), one for vendors (15-minute slots only).
It won't schedule meetings with people outside your Google Workspace unless they click the link. For internal meetings with your team of three, just keep using Google Calendar directly.
Getting started — step by step
Sign up. On your Mac, open Chrome and go to reclaim.ai. Click Get Started Free. Sign in with your Google Workspace account (the same one connected to your work calendar). Reclaim will ask permission to read and write calendar events — click Allow. This is how it can protect your focus blocks and create meetings from booking links.
Create your donor booking link. Once you're in the dashboard, click Scheduling Links in the left sidebar → Create Link. Name it something like “Coffee with Priya.” Set the meeting length to 30 minutes. Under availability, choose the times you're generally free for donor meetings (e.g., Tuesday through Thursday, 10 a.m. to 3 p.m.). Click Save. Copy the link — this is what you'll paste into emails instead of the back-and-forth.
Create your vendor booking link. Same process: Scheduling Links → Create Link. Name it “Vendor call — 15 min.” Set the meeting length to 15 minutes. Restrict availability to one or two afternoons per week. This keeps vendor calls from scattering across your calendar.
Set up your focus-time blocks. In the left sidebar, click Habits → Create Habit. Name it “Writing time — annual report / board deck.” Set it to 1.5 hours, 3 times per week. Choose your preferred time window (mornings tend to work best for writing). Reclaim will automatically find open slots in your week and place the blocks there. If someone reschedules a meeting into that time, Reclaim moves the writing block to the next available window instead of deleting it.
Test the donor link. Send your donor booking link to yourself in a separate email. Click it. You should see a clean calendar view showing your available times. Pick one. Confirm that the meeting appears on your Google Calendar. If it does, the link is ready to send to donors.
The free tier is generous and covers everything above. If you find yourself wanting priority scheduling (where Reclaim automatically ranks which meetings get the best time slots), that's when the $10/month Starter plan becomes worth it.
Dropbox, cleaned up
Already paid · no new cost
What it is: The file storage you already use — but reorganized so finding a past grant narrative or donor profile takes seconds, not minutes.
Why it helps you: The content is all there. It's the structure that's working against you. Sort by program, donor, and year. Add saved searches for the questions you ask every quarter. No new software — just an afternoon of housekeeping that pays back every week.
This won't add new features to Dropbox. It's the same tool, but with a folder structure that matches how you actually look for things.
Getting started — step by step
Create three top-level folders. Open Dropbox on your Mac (or go to dropbox.com in Chrome). In the root of your work folder, create three new folders:
1 — By Program (one subfolder per program your nonprofit runs)
2 — By Donor (one subfolder per major donor or foundation)
3 — By Year (2024, 2025, 2026 — for annual reports, audits, board decks)
Move, don't copy. Spend one afternoon dragging existing files into the right folders. Don't worry about getting every file — start with the ones you look for most often: last year's annual report, the current board deck, the three grant narratives you're reusing, and the donor profiles for your top twenty donors.
Set up saved searches. In Dropbox, click the search bar at the top. Type a search you run regularly — for example, “annual report 2025” or “grant narrative arts education.” When the results appear, look for the option to save this search (it appears as a bookmark icon or “Save search” link). Do this for three or four searches you run every month.
Star the ten files you open most. For each of the files you open constantly — the donor tracking spreadsheet, the current board deck, the events calendar — right-click the file and choose Star (or click the star icon next to the file name). Starred files appear in a dedicated section at the top of your Dropbox, so you never have to dig for them.
This should take about two hours. Do it on a Friday afternoon when the inbox is quiet. Once the structure is in place, new files go into the right folder as you create them — no maintenance required.
AI 2 essential · 1 conditional
Claude Pro
~$20 / mo · cancel your ChatGPT subscription
What it is: A writing partner (from Anthropic) that you talk to in plain English. Drop in a donor's last five years of giving history plus the new ask and it drafts a thank-you that sounds like you. Drop in three pages of scribbled board notes and get a clean one-page summary in 30 seconds.
Why it helps you: The forty evenings on the annual report were mostly staring at the cursor. Claude drafts section one from last year's version plus this year's numbers — you edit, not write from scratch. It's also meaningfully better than ChatGPT for long-form writing in a consistent voice, which is why we're moving you over and canceling the ChatGPT sub you said you don't use.
It doesn't have access to your email or calendar — you have to paste or upload the material you want it to work with. And it will occasionally get tone wrong on the first try. Think of it as a smart first draft, not a finished product.
Getting started — step by step
Sign up on your Mac. Open Chrome and go to claude.ai. Click Sign Up. Use your personal email (not the work Google Workspace one — keeping this separate from your org's accounts is cleaner). Create a password. You'll get a verification email — click the link in it to confirm.
Upgrade to Pro. Once signed in, click your name in the bottom-left corner → Settings → Subscription → Upgrade to Pro. Choose the $20/month plan. Enter your payment information. The Pro plan gives you significantly more usage and access to the most capable model, which matters for the long-form writing you'll be doing (board decks, annual report sections, grant narratives).
Turn on the Projects feature. On the left sidebar, you'll see Projects. Click the + to create a new one. Name it “Donor Communications.” This is where you'll store context that Claude can reference across conversations — like your organization's mission statement, your voice and tone preferences, and donor background information. Upload a few key documents: your nonprofit's one-page mission summary, a donor thank-you letter you wrote that you're happy with (so Claude can learn your voice), and this year's giving summary.
Install on your iPhone. Open the App Store. Search Claude — the correct one is by “Anthropic” with a brown/tan circular logo. Tap Get. Sign in with the same account. Your projects and conversations sync across devices.
Try it with a real task right now. Open your “Donor Communications” project. Start a new conversation. Try one of the prompts below — use a real donor name and real numbers. Read the draft it produces. Edit it in your voice. The first one might take ten minutes; by the third, it takes three.
Try this — copy and paste into Claude (replace the bracketed parts)
I need to write a thank-you letter to [donor name], who just gave $[amount] to our [program name] fund. This is their [first / third / tenth] gift. They care most about [what they care about — e.g., arts education for underserved kids]. Write a warm, personal thank-you letter in my voice — not formal, not gushing, just genuine. Two paragraphs. Mention specifically what their gift will fund this quarter.
Replace the bracketed parts with real information. The more specific you are about the donor, the less editing the draft will need. If you uploaded a sample thank-you letter to the project, Claude will match that tone.
For board deck prep
I'm preparing the development section of our quarterly board deck. Here are my raw notes from the past three months: [paste your notes]. Last quarter's slide said we raised $[amount] against a goal of $[goal]. This quarter we raised $[amount]. Draft a one-page narrative summary for the board — lead with the headline number, then three bullets on what's working, one bullet on what needs attention, and a short note on next quarter's pipeline. Keep the tone confident but honest.
Paste in your actual scribbled notes — they don't have to be clean. Claude is good at pulling structure out of rough material.
For annual report sections
I'm writing the [program name] section of our annual report. Here's last year's version: [paste it]. Here are this year's numbers and highlights: [paste your notes]. Rewrite this section for the current year. Keep the same tone and structure as last year's version, but update all the numbers and add the new highlights. About 400 words. Don't use words like "transformative" or "impactful" — our voice is warmer than that.
Giving Claude last year's version as a reference is the trick that saves the most time. It matches the structure and tone instead of starting from a blank page.
Otter.ai Pro
~$8 / mo (annual) · $17 / mo monthly
What it is: A meeting transcription app. Hit record on your phone or laptop — during a donor coffee, a board call, a strategy session — and afterwards you get a clean transcript, a one-paragraph summary, and a list of who said they'd do what.
Why it helps you: Instead of scribbling notes while trying to have a real conversation with a donor, you listen properly. Afterwards Otter hands you the followup-ready summary, which you paste into Claude to draft the thank-you email in your voice. SOC 2, GDPR, and EU AI Act compliant — the only transcription tool we recommend for donor content. (Always ask for consent before recording.)
It won't record phone calls automatically — you have to start the recording. And it needs a decent microphone to work well in a noisy coffee shop. For in-person meetings, set your phone on the table between you.
Getting started — step by step
Install on your iPhone. Open the App Store. Search Otter — the correct one is “Otter: Transcribe Meeting Notes” by “Otter.ai, Inc.” with a blue logo. Tap Get.
Create an account and upgrade. Open the app. Tap Sign Up. Use your work email. Once signed in, tap the profile icon (top-left) → Plans → choose Pro ($8.33/month billed annually). The Pro plan gives you 1,200 minutes of transcription per month and longer recording limits, which matters for board meetings that run over an hour.
Install the desktop app. On your Mac, go to otter.ai in Chrome and click Download. Install the app. Sign in with the same account. For Zoom and Google Meet calls, Otter can join the meeting automatically as a participant (called “OtterPilot”). To turn this on: open Otter on your Mac → click your profile icon → Settings → OtterPilot for meetings → turn on Auto-join Google Meet. When you join a Google Meet from your calendar, Otter will ask to join too.
Practice with a real meeting. At your next donor coffee or board call, open the Otter app on your iPhone and tap the big Record button at the bottom. Place your phone on the table, screen-up, between you and the other person. Before you start: say something like “I'm going to record this so I can focus on our conversation instead of taking notes — is that okay with you?” Always get consent.
Review and use the summary. After the meeting, open Otter. Your recording will appear in the list. Tap it. You'll see a full transcript and, at the top, a Summary section with key points and action items. Copy the summary, open Claude, and paste it in with a prompt like: “Here are my notes from a donor meeting with [name]. Draft a follow-up thank-you email in my voice.”
For in-person meetings in noisy environments, you'll get better results with the iPhone sitting on the table rather than in your pocket. Otter handles background noise reasonably well, but closer is better.
Grantable Conditional
~$25 / mo (nonprofit pricing, orgs under $500K budget)
What it is: AI grant-writing software. You load it up with your nonprofit's past applications and org voice. When a new grant comes up, it drafts the answers from your organization's own language — not a generic template.
Why it helps you: Only worth it if you're writing four or more grants a year. At that volume, it pays for itself in the first application. If you write one or two, skip this and lean harder on Claude. We'd ask about your grant pipeline before recommending a yes or no.
It won't find grants for you or manage the submission process. It's a drafting tool only. And if your org's voice hasn't been captured in past applications yet, the first few drafts will need heavy editing.
Getting started — step by step
Sign up. On your Mac, open Chrome and go to grantable.co. Click Start Free Trial. Use your work email. Grantable offers nonprofit pricing for organizations with budgets under $500K — if your org qualifies, you'll see the discounted rate ($25/month) during checkout. The free trial gives you two weeks to test it before any charge.
Upload three past applications. Once you're in, click Knowledge Base (or “Organization Profile” depending on the version). This is where Grantable learns your voice. Upload three of your strongest past grant applications — choose ones where you felt the writing genuinely represented your organization. Also upload your mission statement and your most recent annual report. The more context you give it, the closer its drafts will be to your actual voice.
Start a new grant. Click New Grant. Enter the funder name and paste in the application questions (or upload the RFP if it's a PDF). Grantable will draft answers pulling from your uploaded materials. The first draft will need editing — that's normal. The time savings come from not staring at a blank page.
Decide at the end of the trial. After two weeks and at least one real application, ask yourself: did this save me a meaningful number of hours? If yes, keep it. If the drafts needed so much editing that you spent nearly as much time as writing from scratch, cancel and lean on Claude for grant writing instead.
If you write fewer than four grants a year, skip Grantable entirely. Claude can handle occasional grant drafting if you paste in the RFP questions and your past responses. Grantable's value is in volume.
04B — What we considered and ruled out
A short list of tools we looked at and didn't pick.
A few well-marketed options we considered and decided against. Each of these is a tool a knowledgeable friend might reasonably suggest; we don't think any of them is the right fit for you specifically.
Notion AI
A popular all-in-one workspace with built-in AI writing features. The problem is that you already have Dropbox, Google Docs, and Google Calendar — Notion would be a fourth system to maintain, not a replacement for any of them. The AI writing is decent but not as strong as Claude for the kind of long-form, voice-specific work you need (donor thank-yous, board narratives). Adding Notion would create more complexity, not less.
Grammarly Business
Good at catching typos and tightening sentences, but your writing isn't the problem — the blank page is. Claude handles the blank-page problem (drafting from notes and context) in a way that Grammarly doesn't. And Grammarly's AI rewriting features tend to flatten exactly the personal warmth that makes your donor letters effective.
Microsoft Copilot
Microsoft's AI assistant works best inside the Microsoft 365 suite — Word, Outlook, Excel. Your organization runs on Google Workspace, which means Copilot would be working in a second-class environment for you. The integration gaps would create more frustration than the AI features would save. If you ever move to Microsoft 365, revisit this.
Fireflies.ai (instead of Otter)
A capable meeting transcription tool with slightly better integrations for CRMs. We chose Otter over Fireflies for two reasons: Otter's SOC 2 and GDPR compliance documentation is more transparent (important when you're recording donor conversations), and its mobile app is meaningfully better for in-person meetings at coffee shops, which is where a lot of your donor relationship-building happens.
05 — Something only yours
Your donor thank-you letter assistant.
You already have Claude Pro from the section above. This takes it further -- a dedicated space inside Claude that knows your nonprofit, your voice, and your donor relationships, so every thank-you letter starts 80% done instead of blank.
The idea: a Claude Project pre-loaded with everything it needs to draft thank-you letters that sound like you wrote them on your best day. Your organization's mission, your tone, the way you reference a donor's specific gift and what it funded, the personal callbacks that make your letters the ones donors actually keep. You paste in the basics -- who gave, how much, what it supports, any personal detail -- and get back a draft you can send with minor edits.
This is not a template. Templates are why donor thank-yous feel like form letters. This is a writing partner that has read your best work and matches it, every time, even on the Friday afternoons when you're running on caffeine and guilt.
Claude Project: "Donor Thank-You Letters"
No extra cost -- uses your Claude Pro subscription
What it is: A dedicated project inside Claude with a custom system prompt and your reference documents. Think of it as a Claude that already knows who you are, where you work, and how you write -- so you skip the explaining and go straight to drafting.
Why it helps you: Those thank-you letters that keep falling behind? The ones you care about too much to rush but don't have time to write properly? This gets you from "I owe Linda a letter" to "here's a draft that sounds like me" in about two minutes. The personal, specific tone that donors love -- the one that references their daughter's painting classes or the conversation you had over coffee -- that's exactly what this is built to preserve.
Getting started -- step by step
Open Claude and find Projects. On your Mac, open Chrome and go to claude.ai. Sign in with the account you created in Section 04. In the left sidebar, look for Projects. If you already created a "Donor Communications" project during the Claude Pro setup, you can either rename it or create a new one specifically for thank-you letters. Click the + button next to Projects to create a new one. Name it "Donor Thank-You Letters".
Open the project settings. Click into your new project. You'll see a settings area at the top (or a gear icon). Look for the field labeled "Custom Instructions" or "System Prompt" -- this is where you tell Claude how to behave inside this project. Everything you put here applies to every conversation you start within this project, so you only set it up once.
Paste the system prompt. Copy the entire block below (under "System prompt -- ready to paste") and paste it into the Custom Instructions field. This prompt tells Claude who you are, how you write, and what to avoid. Read through it first -- if anything doesn't match your actual voice or preferences, edit it before saving. Click Save.
Upload your best thank-you letters. In the project, look for an option to add knowledge or upload files (it may say "Project Knowledge" or have a paperclip/upload icon). Upload 3 to 5 of your best past thank-you letters -- the ones where you felt the tone was exactly right. These don't have to be perfect; they just need to sound like you. Claude will use them as voice references. Good formats: PDF, Word doc, or just paste the text into a .txt file and upload that.
Upload your organization one-pager. Also upload a short document about your nonprofit -- your mission statement, a list of current programs, and the names of any major initiatives or events. This gives Claude the context to mention specific programs accurately instead of guessing. If you don't have a one-pager, a copy of the "About" page from your website works fine.
Test it with a real donor. Start a new conversation inside the project. Try the first test prompt below -- use a real donor name, a real gift amount, and a real program. Read the draft Claude produces. It should sound like your voice from the uploaded letters, reference the specific gift and its impact, and feel warm without being gushing. If the tone is off, tell Claude what to adjust ("warmer," "less formal," "more like the letter I wrote to the Garcias") -- it learns within the conversation.
Try a second test with a personal detail. Use the second test prompt below, which includes a personal callback. This is where the project really earns its keep -- the ability to weave in "your daughter took painting classes here" or "you mentioned at coffee that..." is what separates a good thank-you from a great one. Check that Claude includes the personal detail naturally, not as a forced insert.
System prompt -- ready to paste into your project's Custom Instructions
You are a writing assistant for Priya, the Director of Development at a Portland-based arts nonprofit. Your only job is drafting donor thank-you letters in Priya's voice.
Her voice is warm, personal, and specific. She always references the donor's specific gift and names the program or event it supports. She never uses generic fundraising language like "your generous contribution makes a difference" or "we are so grateful for your support." Every letter should feel like it was written by someone who knows the donor personally.
When Priya provides a personal detail or callback to a previous interaction, weave it in naturally -- it should feel like a genuine aside, not a forced insert.
Format every letter as: a greeting using the donor's first name, 2 to 3 short paragraphs, and a warm close signed with Priya's name.
Do not invent details Priya hasn't provided. If you don't know something, leave a bracket like [specific detail] for her to fill in. Keep the tone confident and genuine -- never fawning, never corporate.
Test it -- donor thank-you with specific gift details
Draft a thank-you to Robert and Maria Garcia who gave $2,500 to our youth mural program. This is their third year giving. The gift will fund supplies and teaching-artist stipends for the summer session, which serves about 40 kids from the neighborhood.
Replace with a real donor if you'd prefer. The more specific the details, the less editing the draft needs.
Test it -- with a personal callback
Draft a thank-you to Linda Chen who gave $5,000 to the youth arts program last week. I had coffee with her in March and she mentioned her daughter took painting classes here as a kid. She said watching the kids in the studio reminded her of those Saturday mornings. This is her second gift -- she gave $1,000 last year to the general fund.
This is the kind of letter that used to take 20 minutes to write from scratch. With the project set up, it should take about two minutes of editing.
06 — What this looks like in practice
Conservative time savings, honestly estimated.
Some of these are big weekly chunks. Some are small daily savings that compound. We'd rather understate than overpromise.
Task
Today
With the plan
Weekly saved
Email triage & drafting
Constant background tax; 400 unread by Friday
15-minute morning pass; Superhuman drafts replies in your tone
~3 hrs
Scheduling donor coffees
5–8 emails per meeting
One Reclaim booking link
~2 hrs
Thank-you letters
Drafted from scratch, always behind
Claude drafts from donor history; you edit and send
~1.5 hrs
Board deck prep
Night before, from scratch
Claude drafts from notes + last deck; you refine
~1.5 hrs
Donor-coffee follow-ups
Scribbled notes, remembered partially
Otter records; Claude turns it into a draft email
~1 hr
Estimated weekly savings
8–10 hrs
The hours are real, but the bigger shift most people describe a month in is different: “evenings back.” The annual report no longer eats March. Sunday-night email dread stops. That's harder to put on a spreadsheet.
07 — A suggested rollout
Two weeks. At your own pace.
Each tool above has its own “Getting started” walkthrough. This section tells you what order to do them in, and how to know when each one is working. Everything is designed so you can work through it at your desk — no outside help required, though we're here if you want it.
Week 1 — Foundation
About 4 hours, spread over a few evenings
No AI yet. Just the plumbing — email, calendar, files. Do these in order.
Evening 1 (~1.5 hrs): Superhuman. Follow the “Getting started” steps above. Sign up, install on Mac and iPhone, complete the onboarding, train it on your voice, and set up your VIP senders. You'll know it's working when: you open Superhuman the next morning and your top donors' emails are at the top of the inbox, and hitting Reply produces a draft that sounds roughly like you.
Evening 2 (~45 min): Reclaim.ai. Follow the steps above. Connect your Google Calendar, create two booking links (donors and vendors), and set up your writing-time focus blocks. You'll know it's working when: you send the donor booking link to yourself, pick a time, and it appears on your calendar automatically.
Evening 3 (~2 hrs): Dropbox cleanup. Follow the steps above. Create the three top-level folders, move your most-used files, set up saved searches, and star your ten most-opened files. You'll know it's working when: you search for “annual report 2025” and it appears in two seconds instead of five minutes of clicking through folders.
End of Week 1: One quick pass on Gmail filters. In Gmail (not Superhuman), go to Settings (gear icon) → See all settings → Filters and Blocked Addresses. Create filters to auto-archive the newsletters and internal CC-everyone threads that add noise. This takes fifteen minutes and immediately makes Superhuman's inbox cleaner.
Week 2 — AI tools
About 3 hours
With the foundation working, you layer in AI. Start with real tasks, not demos.
Session 1 (~1 hr): Claude Pro. Follow the “Getting started” steps above. Sign up, upgrade to Pro, create your “Donor Communications” project, and upload your reference documents. Then try all three prompts above with real donor names and real numbers. You'll know it's working when: the first draft of a thank-you letter needs editing but not rewriting — you're fixing ten words instead of writing two hundred.
Session 2 (~30 min): Cancel ChatGPT. Open the ChatGPT app on your iPhone → tap your profile icon → Settings → Subscription → Cancel Plan. Claude is now doing that job better. (See the cancellation section below for the exact steps.)
Session 3 (~1 hr): Otter.ai. Follow the steps above. Install on iPhone and Mac, upgrade to Pro, and turn on OtterPilot for Google Meet. You'll know it's working when: you record your next donor coffee, and the summary it produces afterwards is accurate enough to hand to Claude for a follow-up email draft.
If applicable (~1 hr): Grantable. Only if you write four or more grants a year. Follow the steps above. Upload three past applications. Start one real grant draft. Decide at the end of the free trial whether it saved meaningful time.
Check back in 30 days
—
Give it thirty days and look back honestly: what stuck, what didn't, what feels awkward. The real test of Superhuman is whether Friday afternoon looks different than it used to. The real test of Claude is whether board-deck Sunday disappeared. If anything isn't working, write down specifically what feels wrong — we'll adjust.
08 — Guardrails
What never goes into these tools. And how to get out if you want to.
You work with donors who trust you with their generosity, and a board that trusts you with their organization. That trust has boundaries, and the tools should too. Here are the lines, plainly — what's safe, what's not, and how to walk away from any of this if it doesn't feel right.
Things never to type or photograph into any AI tool
This applies to Claude, Otter, Grantable, and anything else that takes text or voice input. The discipline is the same everywhere, even for tools with strong privacy postures.
Never
Donor Social Security numbers, credit card numbers, bank account details, or EIN numbers from their tax documents. If you're looking at a donor's tax receipt or financial form and want to ask Claude what it means, crop or cover these numbers before photographing or pasting.
Never
Confidential donor conversations that were shared in trust. If a donor told you something private about their family, health, or financial situation during a coffee meeting — even if Otter recorded it — that portion of the transcript should not be pasted into Claude or any other tool. Delete sensitive sections from the Otter transcript before using the rest.
Never
Board executive session content. Anything discussed in executive session (personnel matters, legal issues, compensation discussions) is confidential by nature. Do not transcribe executive sessions with Otter, and do not paste executive session notes into Claude. If Otter was running during a regular board meeting that transitions into executive session, stop the recording immediately.
Be careful with
Donor names combined with specific giving amounts. Saying “draft a thank-you for a donor who gave $50,000 to arts education” is fine. Saying “draft a thank-you for Margaret Chen who gave $50,000” is riskier — you've now connected a real name to a real number in a third-party system. Use first names or initials when the full name combined with the amount would be sensitive.
Be careful with
Internal personnel discussions. If you're asking Claude to help draft a performance review or think through a staffing concern, keep the language general. “A team member who is struggling with event logistics” instead of “Sarah, who keeps missing deadlines on the gala.” This protects your staff and keeps HR-sensitive information out of external systems.
Generally fine
Public program descriptions, draft thank-you letters, event logistics, board deck narratives, annual report sections, and grant application language. These are the intended use case. Anything that would appear in a published annual report or a mailed donor letter is fine to draft with AI assistance.
How to know when AI is wrong
It will be wrong sometimes. Here's how to spot it:
Watch for
Numbers that don't match your records. If you ask Claude to summarize your fundraising quarter and it says you raised $1.2M when the real number is $850K, it's not lying — it's confusing context from different parts of what you pasted in. Always verify dollar amounts and statistics against your own records before they go into a board deck or donor communication.
Watch for
Donor history that sounds specific but isn't sourced. If Claude says “this donor has given for six consecutive years” and you didn't provide that information, it may be guessing from context clues. If a claim about a donor's history matters (and in a thank-you letter, it always matters), check it against your CRM or Dropbox records before sending.
Watch for
Tone that's too polished or too generic. Claude's first drafts sometimes sound like a professional fundraising consultant instead of you. If a donor who has known you for five years received that letter, would it sound like it came from you or from a stranger? When in doubt, read it out loud. If it doesn't sound like something you'd say across the table, edit until it does.
How to cancel everything
If any of this doesn't feel right after 30 days, here's exactly how to walk away from each one. No penalties, no retention tricks.
Superhuman
Open Superhuman on your Mac → click the gear icon (bottom-left) → Account → Billing → Cancel Subscription. Your email stays in Gmail exactly as it was — Superhuman is a layer on top, so canceling it just means you go back to regular Gmail. Nothing is lost.
Reclaim.ai
Go to app.reclaim.ai → click your profile icon (top-right) → Settings → Billing → Cancel Plan. If you're on the free tier, there's nothing to cancel — just stop using it. Your Google Calendar events remain exactly as they are; Reclaim just stops creating new focus blocks and booking links.
Claude Pro
Go to claude.ai → sign in → click your name (bottom-left) → Settings → Subscription → Cancel Plan. You'll drop to the free tier, which still works but with lower usage limits. Your past conversations and projects are preserved.
Otter.ai Pro
Open Otter on your Mac or go to otter.ai in Chrome → click your profile icon → Settings → Subscription → Cancel Subscription. Your existing transcripts remain accessible on the free tier. If you signed up through the App Store on your iPhone, cancel there instead: iPhone Settings → your name → Subscriptions → Otter → Cancel.
Grantable
Go to grantable.co → sign in → click your profile icon → Settings → Billing → Cancel Subscription. Your uploaded documents and past grant drafts remain accessible in read-only mode. You can export them as Word documents before canceling if you want local copies.
09 — The numbers
Software, and (optionally) help setting it up.
The plan you're reading is free. The only costs are the software subscriptions below. If you'd like us to set things up alongside you instead of going DIY, the implementation package is optional.
Software — monthly, ongoing
Superhuman~$30/mo
Reclaim.ai$0–10/mo
Claude Pro~$20/mo
Otter.ai Pro~$8/mo
Grantable (if 4+ grants/yr)~$25/mo
Google Workspace / DropboxAlready paid
Canceled: ChatGPT− $20/mo
Net new monthly~$48–73/mo
Implementation help — optional, one-time
Week 1 setup (alongside you)$1,400
Week 2 setup + training$1,400
30-day tune-up callIncluded
Full package$2,800
If you DIY, net new is about $48/month
Against 8–10 hours a week back, that pays for itself the first week of March when the annual report used to start eating your evenings. If you'd like help with the setup, the one-time implementation fee is optional — most people can do it themselves from this plan.
10 — If you want your own
This is a sample. Yours would be different.
Every plan starts with your actual answers — seven short sections of plain-English questions, around 20 to 25 minutes at your own pace. You can skip anything that doesn't feel right.
You'll get back something written for your situation.
Not a template. We read every answer and recommend the tools that actually fit your work, your budget, and what's driving you up the wall. The plan is yours to keep, whether you do it yourself or decide to have us help set things up.
LanternPLAN