How We Filed Our Taxes Over Slack

How We Filed Our Taxes Over Slack

Taxes are a necessary evil for every business, and working with an accounting service is equally necessary and potentially more evil if you make the wrong choice. While the most important aspect in choosing a firm is accuracy in your filing, the next best thing is the experience and relationship that you have with the firm.

We're sharing our experience with two different firms in how they managed communication with us throughout the filing process.

The Old Way: Endless Email Threads

When we filed our taxes for 2021, we contracted a top-recommended firm and hopped on a few intro calls to determine what information we needed. They recommended that we set up a shared Google Drive folder and that we communicate primarily over Gmail with the 3 reps handling the account.

We created the Drive folder, shared with the right folks, and then were again asked for the details in the email thread itself. There were necessary questions, follow-ups, and clarifications, and before we knew it, we had a gmail chain of 67 messages spanning 6 months. The thread became so long that my Chrome browser can't render it in less than 10 seconds.

Problem #1: File History 🗃

This email thread was so long that it crashed my Gmail tab on a laptop.

There's no way to get an aggregate view of all attachments uploaded throughout this thread, meaning we had to scroll through each email in the chain and download attachments individually if you want to double-check a document.

Problem #2: Threading 🧵

Ah yes, easy to find exactly what I'm looking for.

Gmail generally does a great job at handling threads in the UI, but replies can get messy depending on the email client of the other party you're communicating with. The default behavior to include previous email content in a reply meaning you end up with a total number of messages as: (n^2 + n) / 2.

Fun fact: this is sometimes called a Triangular Number!

Problem #3: Politeness 🤭

This is a solvable one, but there are still social norms around using greetings and closing messages in email rather than getting to the point. Look below to see the visual space and reading time wasted by parsing through polite greetings:

A very polite but long exchange

The New Way: Instant Replies on Slack

For 2022, we switched our accounting service to Fondo (this is not paid promotion) to consolidate our bookkeeping, taxes, and R&D credits. Fondo uses shared Slack channels to handle communication with their customers in addition to a web dashboard to submit necessary documents.

With Fondo, we were set up with a dedicated shared channel to talk directly with our accountant. Through this channel we could also share collaborative documents like Google Docs and can easily upload new things to share and discuss.

Replies are speedy, informal, and right to the point. When we need to upload files, they're aggregated into a single view that both of us can see. And as an added bonus, the UX of Slack is cleaner and snappier than Gmail threads. Rather than 6 months of back and forth, we got everything in order and ready to file in a matter of weeks.

We also ended up with about a 50% reduction in our total cost to file, though YMMV based on company size and annual expenses.

What Other Services Can Move to Slack?

Doing taxes over Slack is something that seemed impossible only a year ago, so we're excited to see what's next. We still use slow email back-and-forth with our legal teams, payroll services, insurance companies, and other key functions that can benefit from real-time collaboration.

We now look as Slack collaboration as a key decision point when choosing a service – knowing that we'll have instant access to their team and aren't subject to the problems mentioned above.

What is Email's Future in this New World?

We're still heavy email users. It works best for communication with any company for which we aren't yet a customer or a vendor. Once a contract is signed and we've reached that level of corporate intimacy, instant Slack messaging becomes the more efficient way for to communicate, and we're seeing more and more partners adopting this with us.

If you building something new and moving your workflows to Slack, reach out to us to see if we can help to more easily track conversations and get things done faster.