We’re currently using SharePoint and Box for client document uploads. Both platforms work well for us, SharePoint integrates seamlessly with our internal workflows and permissions, while Box is great for secure file sharing, external collaboration, and ease of use for clients.

I can feel the frustration in this, and you're hitting on something real that a lot of firms struggle with. The core issue you're naming is this: workflows are designed to move work through steps in sequence, but the narrative of why something is happening gets fragmented across multiple places. Notes capture the story. Workflows track the execution. And somewhere between the two, you lose the connective thread. Here's how I think about it. Workflows should document the process, the repeatable checklist of what happens and when. Notes should document the narrative, the context, the reasoning, the history of the decision. These aren't redundant if you think of them as serving different purposes. A workflow says "here's how we mail a check." A note says "client called on March 10 requesting a check mailed to their new address because they're funding their 529 and need it before the school year." The problem you're running into is that Wealthbox (like most CRMs) doesn't surface workflow comments in reports, and the client feed gets cluttered by every subtask you create. That's a system limitation, not a design failure on your part. You can't fix that by rethinking the structure. What you can do is be intentional about where you put what: Use step notes inside the workflow itself. This is where I'd capture the "why", the recommendation date, the type of transaction, any nuance about why this particular process is happening for this particular client. Step notes don't clutter the feed, and they live right there in the workflow where someone executing the tasks can see the context they need. Keep the client-facing note separate. If you need a record of client contact (receipt confirmation, deposit confirmation), that's a note on the contact record. That's for compliance and narrative continuity. It's not part of the workflow machinery. Design the workflow as a pure checklist. Receive check > Confirm receipt > Document receipt in check log > Mail check > Confirm deposit > Send confirmation. Each of those is a task. The workflow enforces the sequence. It doesn't try to be the keeper of the story.

@Jayce Nall Great question. In my experience the friction starts almost immediately. It is just easier to absorb when the team is small. As staff and clients are added those small gaps compound and become more visible. Growth tends to amplify whatever systems are already in place.

Yes, best practice is to document the QCD in Redtail (amount, date sent, charity, and which IRA it came from). Then, when 1099-Rs are issued, it is helpful to send a courtesy reminder to the client letting them know what portion of the total distribution was a QCD, since the 1099-R generally shows the full gross distribution and does not clearly identify it as a QCD (often it just looks like a normal distribution/code). It is helpful to have a Keyword of "QCD" on all client's who took a QCD so you can easily run a report to know who to send emails to. This helps ensure the client and/or CPA reports it correctly on the tax return. You are not providing tax advice, just confirming the transaction details for their records.