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How We Run A Million Dollar Agency on Slack & Trello Free Plans

In a world where AI is taking over just about everything by storm, and in which it seems nearly every tool touts some sort of AI component, talking about Trello + Slack seems a bit silly. 

They’re hardly new – they’ve both been around for years and are quite well known. 

Nor do they have any AI features that I’m aware of. 

Yet, despite the influx of fancy AI tools recently, the ones that we still use the most at Shortlist are undoubtedly Slack & Trello

Now, it may very well be the case that you’re familiar with these tools, and perhaps you don’t have all that much to learn about them. 

But maybe, just maybe, there’s a thing or two that we’re doing that might make you think about things a little differently. 

How We Use Slack At Shortlist

As previously mentioned, our team is primarily based in North Macedonia, so as the sole American I need various ways to manage the team 100% remotely. 

That’s where Slack comes in. 

One of the amazing things about Slack is that, despite the fact that we have dozens of employees in our account, that we’ve written nearly 2 million messages in the platform, and that we have a number of apps integrated with it – we don’t pay for it. 

If we did, it would cost us over $400 a month – not a small amount for a small business. 

But the pro features that are offered are not things we really value. 

Sure, it would be nice to have access to messages older than 90 days, but it’s rarely necessary. Additionally, very occasionally there are some issues with inviting someone from outside the organization into our workspace, but even for that we’ve found a workaround. 

At the end of the day, we’re just getting incredible value for free. 

(And I know it really bothers Salesforce, who recently acquired Slack, because they keep sending me emails talking about how much of an anomaly our account is)

Using it is fairly straightforward. 

  • There’s a channel for each department, such as sl-bizdev (to which we send payment notifications). 
  • Occasionally, there are channels for clients if they would like more streamlined communication, but this is definitely the exception and not the rule. 
  • Specific company events, such as the team retreat or the fitness challenge, will also have dedicated channels. 

The rest is handled through DMing and Group Chats. 

It sounds simple and it is, but I would say, without this, the whole ship would sink. It’s basically replaced 99% of internal emailing (client emailing is another story). 

How We Use Trello At Shortlist

If there is one thing Slack doesn’t do well, it’s project management. 

And honestly I respect how well they’ve stayed in their lane as opposed to trying to be the every tool for everyone. 

So for that, we need a separate tool; Trello. 

Unsurprisingly, Trello is another tool of which we’re power users and don’t pay a thing. However, unlike Slack they seem to have given up on us completely because I can’t even find a way to upgrade nor do I know what it would cost to do so.

But I wouldn’t anyway, because I really have no idea what the premium plan gets you, suffice to say that it just isn’t compelling enough to warrant seeking it out and spending hundreds of dollars per month. 

Trello is a traditional kanban system for project management. We have a few boards, like Slack channels, for each department. Columns such as Up Next, Recurring Tasks, and In Progress indicate the current state the task is in, the most important one, in my opinion, is Dave Review. Then cards themselves represent the tasks.

As the team will tell you, I am, to a fault, neurotic about making sure each card has a complete description as well as a checklist. 

It sounds simple, but I find few people naturally do this. 

The description is important because I often find myself task switching across various people and departments and I need an easy way to jog my memory. 

The checklist, in addition to helping everyone understand where we’re at in the task, is important in that it forces the task owner to really think through the steps when they start. When you do this, you often see the various potential bottlenecks and approvals that are needed and can more efficiently approach the task. 

A reasonable question would be – where do you discuss tasks? Trello, or Slack?

TBH, it’s mostly Slack.

It’s a bit odd because, Trello saves the history of any notes related to the card on the card itself, but, in the same way that Slack isn’t a project management app, Trello isn’t a chat app. 

Again, maybe these things aren’t 100% ideal, but, they rarely cause a problem. 

Moreover, you’d probably assume that we integrate the two tools, so that changes and updates in Trello appeared in Slack. 

It’s true, they are integrated, but the number of notifications going from one to the other is pretty minimal – you’d hardly notice it. I’m a big believer in as few notifications as possible, which is why I’m basically not subscribed to any newsletters and maintain a consistent inbox 0. 

BUT, we do have a neat little automation between Google Forms and Trello that allows us to take a client intake form and automatically create a task on an associated Trello client board. 

So, we’re not totally in the stone ages!


I think there’s an assumption that as you get larger, you have to act like it. 

Acting like it means paying for expensive communication tools and CRMs (oh, we don’t have one of those either – just spreadsheets). 

But this has worked for us, and it’s worked for us at every size we’ve been so far, and while I’m not sure if it will always work, I can’t say I am seeing the limits of our current setup.

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