Sending more than text in your coaching conversations
Text messages get the job done for quick check-ins, but real coaching moments often call for more. You might want to share a worksheet PDF before a session, drop a motivational image mid-week, or record a quick voice note so your client hears your tone — not just your words. Coachful's built-in client chat supports images, files, and voice notes natively, so you never have to paste a Google Drive link and hope your client clicks it.
This guide walks you through exactly how to send each media type in client chat, covers the formats and size limits you need to know, and shares a few pro tips for using rich media to boost client engagement and retention.
TL;DR — Quick answer
- Images: tap the attachment icon in any chat thread and select a photo, or drag and drop from your desktop.
- Files (PDF, DOCX, etc.): use the same attachment icon and choose any supported file from your device.
- Voice notes: tap and hold the microphone icon to record; release to send.
- All media works inside both 1:1 direct messages and Squad group chats.
Where client chat lives in Coachful
Every coaching relationship on Coachful includes a persistent, real-time messaging thread powered by Stream Chat. You'll find your conversations in two places depending on context:
- Direct messages (1:1): navigate to Messages in your coach dashboard sidebar. Each client has their own thread.
- Squad chats: open Programs → [Your Program] → Squad to access the cohort squad that is automatically created when clients enroll. Community squads live under Community → Squads.
The media-sending features described below work identically in both contexts. Whether you're dropping a PDF for one client or sharing an infographic with your entire cohort squad, the interface is the same.
How to send images in client chat
Sharing images is one of the fastest ways to add context to a coaching conversation — think progress-tracking screenshots, visual frameworks, inspirational graphics, or a quick photo of a whiteboard sketch from your last session.
From a desktop browser
- Open the chat thread (direct message or squad) where you want to share the image.
- Click the paperclip / attachment icon to the left of the message input bar.
- Select Upload image (or simply drag and drop the image file directly into the chat window).
- Choose your file from your computer. Supported formats include JPG, PNG, GIF, and WebP.
- Add an optional caption in the message field, then press Enter or click Send.
From the Coachful mobile app
- Open the Coachful app on iOS or Android and navigate to your client's chat thread.
- Tap the + (plus) icon or attachment icon beside the text input.
- Choose Photo Library to pick an existing image, or Camera to snap a new one on the spot.
- Confirm your selection and tap Send.
Images render as inline previews in the chat thread so your client can see them immediately without downloading anything. GIF files play inline, which makes them handy for a quick celebration reaction when a client hits a milestone.
How to send files in client chat
Files are where coaching content really shines. Sending a worksheet, a habit tracker PDF, a slide deck from your session, or a contract takes seconds — and it lives right inside the conversation where your client will actually look for it.
Supported file types and size limits
Coachful chat (powered by Stream) supports a broad range of file types including PDF, DOCX, XLSX, PPTX, TXT, CSV, ZIP, and MP4. The default file size limit is 100 MB per upload. For very large video files, consider hosting them inside a Program task instead, where Coachful's video player provides a better viewing experience for your clients.
Step-by-step: sending a file
- Open the relevant chat thread in your dashboard or mobile app.
- Click or tap the attachment icon.
- Select Upload file and browse to the document on your device.
- Coachful will show a file thumbnail and the file name before sending. Confirm it's the right document.
- Add a message if needed (e.g., "Here's this week's reflection worksheet — complete it before Thursday's call"), then send.
Your client will see the file as a downloadable attachment with the file name, type icon, and file size displayed. They can tap or click to download it directly to their device. Files are stored securely and remain in the chat history, so clients can scroll back and find that worksheet weeks later without asking you to resend it.
Tip: If you find yourself sending the same worksheet to every new client, consider adding it as a task attachment inside your Coachful Program instead. That way it's delivered automatically on the right day of the program — zero manual effort. See how to add resources to program tasks for details.
How to record and send voice notes
Voice notes are arguably the most underused feature in coaching chat — and the most powerful. A 45-second voice message can convey encouragement, nuance, and warmth that three paragraphs of text simply cannot. Coaches who use voice notes report that clients feel more connected between sessions, which directly improves retention.
Recording a voice note on desktop
- Open any chat thread in your Coachful dashboard.
- Locate the microphone icon to the right of the message input field.
- Click and hold the microphone icon to begin recording. You'll see a live recording indicator and a timer.
- Speak clearly. Keep voice notes under 2 minutes for best engagement — shorter messages get played more reliably than long ones.
- Release the icon to stop recording. A preview waveform appears.
- Click Send to deliver it, or click the trash icon to discard and re-record.
Recording a voice note on mobile
- Open the Coachful iOS or Android app and navigate to the chat thread.
- Tap and hold the microphone icon. Recording starts immediately.
- Slide left to cancel without sending, or release your finger to stop and preview the message.
- Tap Send to deliver.
Voice notes play inline in the chat with a waveform scrubber. Your client can play, pause, and rewind without leaving the conversation. On mobile, they can also listen on the go — perfect for a client who wants to hear your feedback during their morning commute.
Pro tip from coaches using Coachful: Send a voice note within 30 minutes of a completed session. A quick "Great work today — here's one thing I want you to focus on before we talk again…" keeps momentum alive and makes clients feel genuinely seen. It takes 60 seconds and dramatically increases the likelihood they complete their between-session tasks.
Sending media in Squad group chats
Everything above applies equally to Squad chats, which are the group messaging spaces Coachful creates for your cohorts and communities. When you share a file or image in a squad, every member of the squad receives it — making it the fastest way to distribute group resources.
A few squad-specific considerations:
- Cohort squads are automatically created when clients enroll in a Program, so your entire program cohort is already in the room. Drop the week's reading material here at the start of each week.
- Community squads are always-on group spaces. They're great for ongoing resource sharing with your wider audience — think weekly motivational images or a monthly resource pack.
- Voice notes in squads work the same as in DMs. A voice note addressed to the group ("Hey team, quick update on this week's challenge…") creates a much more personal feel than a broadcast text message.
As a coach, you can also pin important messages in a squad — including file-containing messages — so resources don't get buried in the chat history. Click the three-dot menu on any message and select Pin message.
Pro tips for using rich media effectively in coaching
Use images to celebrate wins publicly
When a client shares a milestone — finished a 5K, landed a new client, hit a revenue goal — screenshot the message or ask them to send a photo, then celebrate it in the squad chat. Social recognition inside your cohort builds community and motivates other members. It costs nothing and takes ten seconds.
Create a weekly voice note ritual
Rather than typing a generic weekly recap, record a 90-second voice note every Monday morning that previews the week's theme and what clients should focus on. It feels like a personalized message even in a group context. Coaches who do this consistently see higher program completion rates.
Keep your file names descriptive
Rename files before uploading. "Week3_MindsetWorksheet_Coachful.pdf" is infinitely more useful than "doc_final_v3.pdf" when a client searches their downloads folder three weeks later.
Combine media types for maximum impact
Send a voice note and attach the relevant worksheet in the same message. The voice note grabs attention; the file provides the actionable tool. This combination consistently outperforms either format alone.
Ready to see how Coachful's all-in-one platform keeps your client communication, programs, and billing in one place? Explore Coachful or sign in to your workspace to start using rich media in your client chats today.
Troubleshooting common issues
The attachment icon is greyed out or missing
This typically means the chat thread is read-only or you're viewing a legacy standalone squad (which is deprecated). Make sure you're in an active direct message thread or a cohort/community squad. If the issue persists, try refreshing the page or clearing your browser cache. On mobile, update the Coachful app to the latest version.
My file upload fails or gets stuck
Check the file size — anything over 100 MB will be rejected. Also verify your internet connection is stable before uploading. Large files (50–100 MB) can take 15–30 seconds on a typical broadband connection. If a specific file type is failing, it may be an unsupported format; convert it to PDF and try again.
Voice note recording doesn't start
Coachful needs microphone permission from your browser or device. On desktop, check your browser's site permissions (look for the camera/mic icon in the address bar and ensure microphone access is set to Allow). On mobile, go to Settings → Coachful → Microphone and enable access. After granting permission, reload the app.
Images appear blurry after sending
Chat image previews are displayed at a compressed size for fast loading. Your client can tap or click the image to view it at full resolution. If you need pixel-perfect image quality (e.g., a detailed infographic), attach it as a PNG file rather than pasting it inline — downloads preserve the original resolution.
My client says they can't see the file I sent
Ask them to scroll up in the chat thread — they may have missed the notification. You can also re-send the file or pin the message so it appears at the top of the chat. If they're on mobile and the download isn't working, ask them to try on desktop as a first step, then contact Coachful support if the issue continues.
Voice notes aren't playing for my client
Voice note playback requires a modern browser. Ask your client to update to the latest version of Chrome, Safari, or Firefox. On mobile, they should update the Coachful app. Inline audio doesn't play in some very old Android WebViews — if this is a recurring issue, the client may need to switch to using the native mobile app via app.coachful.co/mobile.
Ready to make your client chats richer?
Great coaching doesn't stop between sessions — and now your chat doesn't have to either. With images, files, and voice notes built directly into Coachful's client chat, you can deliver worksheets at exactly the right moment, celebrate wins with a personal voice message, and share resources with your entire cohort in seconds. No third-party apps, no broken links, no friction.
If you haven't already set up your messaging workflow, sign in to your Coachful workspace and open your first client thread. Or if you're new here, start your free trial and see how an all-in-one platform changes the way you coach. For more guides on getting the most out of Coachful chat and video, browse the full help center.