How to draft check-in emails for customer success managers in 2026

Q: Does QuickDictate run on Mac or Linux?

QuickDictate runs only on 64-bit Windows 10 and 11. It is delivered as an .exe file on GitHub, with a built-in updater that works silently; it can also be built from source. Check the computer requirements before choosing it for a customer success workflow.

A plain guide for customer success managers to draft check-in emails, with steps, tools to consider and common mistakes to avoid.

By XP Daily · 2026-10-21

XP Daily is published by the makers of DaysAid, QuickDictate and YTSort, which are compared here alongside other tools.

Gather the customer's recent activity, pick a reason for the check-in, write the email in one pass, and read it back before sending. You can draft it in an email app, a notes app or a document, or use a dictation tool to type it while you talk.

Option	How it helps you draft
Email app compose window	You type the email directly where it will be sent
Notes app or document	You draft elsewhere and paste into the compose window
QuickDictate	Types what you say into whichever window has focus, such as an editor, chat box, terminal or web form. ^[1]

What you need before you start

Drafting a check-in email takes only a few things.

The customer's recent activity. What they used, what they asked, what they closed. You need it to make the email about them, not about you.
A reason for the check-in. It might be a scheduled touch, a new feature, or a question you want answered. Know which, because it decides what you ask.
The customer's name and how they like to be addressed. A wrong name or a wrong form of address reads as careless.
A place to keep the draft. An email app's compose window, a notes app, or a document all work. What matters is that the draft lives in one place.
A way to get words onto the page. A keyboard is enough. If talking is faster than typing, a dictation tool can type what you say into the compose window.

Set aside a short block before you start a batch of check-ins. Drafting while you are already on a call tends to break your flow.

Step by step

These steps work with any tool, including a keyboard and an email app.

Open the customer's record. Make sure you can see their recent activity before choosing what to say.
Pick one reason for the check-in. One email, one reason. If you have two, send two emails.
Write the subject line first. It should name the customer and the reason, so they know why you are writing before they open it.
Open with their name and the reason. One or two sentences. No preamble about how busy you are.
Add one thing you noticed. A feature they used, a question they asked, or a goal they set. This is what makes it a check-in and not a broadcast.
Ask one question. One question is easy to answer. Several questions read like a survey.
Close with a next step. A time you will follow up, or a link to a resource, not an open offer to answer questions.
Read it back once. Look for a wrong name, a wrong product name, or a sentence that says more than you meant.
Send it. Do not keep editing after you have read it back once.
Log the check-in. Note what you said and what they answered, so the next check-in does not repeat the same question.

Tools that can do it

You do not need special software for this. Here are options to consider.

Your email app. You type the email in the compose window. Check the current details of the email service for limits and cost.

A notes app or document. You draft the email somewhere else and paste it into the compose window. Useful if you want to keep a version history. Check the specific app's current details for limits and cost.

QuickDictate. QuickDictate is made by the team that publishes this site. QuickDictate is a Windows program that types what you say into whichever window you are using. ^[1] You hold a key while you talk, or press it once to start and once to stop, and you can change both keys. ^[1] What you say is typed into whichever window has focus, such as an editor, chat box, terminal or web form. ^[1]

You can use ElevenLabs, Deepgram, OpenAI, AssemblyAI, DashScope or Google, and that provider bills you directly. ^[1] Choose Local in Settings and install a speech model such as Whisper Large v3 Turbo; dictation then needs no internet connection or API key. ^[1] With five of the cloud providers, words appear while you are still talking. ^[1]

You can list words and phrases that are sent to the provider to help it recognise them, and a replacement table fixes spellings such as "Chat GPT" to "ChatGPT". ^[1] Profiles can change the provider, language, vocabulary and formatting depending on which app is in focus. ^[1]

QuickDictate is free for personal and other noncommercial use, with no subscription or account. Cloud providers bill you separately for their service. ^[1] From v0.9.0 on, it is source-available under PolyForm Noncommercial 1.0.0: free for personal and other noncommercial use, and commercial use needs a separate licence. Releases up to v0.8.0 were MIT. ^[1] It runs only on 64-bit Windows 10 and 11. ^[1] It is delivered as an .exe file on GitHub, with a built-in updater that works silently; it can also be built from source. ^[1]

Common mistakes to avoid

Writing a check-in with no reason. If the email does not say why you are writing, the customer has to guess. Pick one reason before you start.

Asking more than one question. One question is easy to answer. Several questions read like a survey and can make the reply harder to write.

Using the wrong name or the wrong product name. Read the email back once before you send it. A wrong name reads as careless.

Repeating the last check-in. If you asked the same question before, the customer may notice. Log what you asked so the next check-in moves forward.

Drafting while on a call. A check-in email written between two calls tends to be short and vague. Set aside a short block.

Sending without a next step. An open offer to answer questions is not a next step. Give a time you will follow up, or a link to a resource.

Frequently asked questions

How to draft check-in emails for customer success managers?

Open the customer's record, pick one reason for the check-in, write the subject line, open with their name and the reason, add one thing you noticed, ask one question, close with a next step, read it back once, send it, and log the check-in. These steps work with any tool, including a keyboard and an email app.

Can QuickDictate type into an email compose window?

Yes. QuickDictate types what you say into whichever window has focus, such as an editor, chat box, terminal or web form. ^[1] You hold a key while you talk, or press it once to start and once to stop, and you can change both keys. ^[1]

Is QuickDictate free for customer success managers?

QuickDictate is free for personal and other noncommercial use, with no subscription or account. ^[1] Cloud providers bill you separately for their service. ^[1] From v0.9.0 on, commercial use needs a separate licence under PolyForm Noncommercial 1.0.0. ^[1] Check that licence before using QuickDictate for customer success work.

Which cloud providers does QuickDictate support?

You can use ElevenLabs, Deepgram, OpenAI, AssemblyAI, DashScope or Google, and that provider bills you directly. ^[1] With five of the cloud providers, words appear while you are still talking. ^[1] You can also choose Local in Settings and install a speech model such as Whisper Large v3 Turbo; dictation then needs no internet connection or API key. ^[1]

Does QuickDictate run on Mac or Linux?

QuickDictate runs only on 64-bit Windows 10 and 11. ^[1] It is delivered as an .exe file on GitHub, with a built-in updater that works silently; it can also be built from source. ^[1] Check the computer requirements before choosing it for a customer success workflow.

QuickDictate is free for personal and other noncommercial use, with no subscription or account. Cloud providers bill you separately for their service. ^[1]

Try QuickDictate

Sources

QuickDictate's own description of itself (the product of this site's publisher)