All Work and No Flow

It started with a manila envelope, whose contents are sacred currency: a piece of work that’s also known as a “deliverable” or an “asset.” A thing that needs to come into being to deliver value to a business. The journey of this asset from phase to phase, person to person, is known as a workflow. Workflows have been attacked by tooling and software since the beginning of work, to make it more efficient, more manageable, and less messy. We have database tools for every industry and common process — the CMS for publishing, the CRM for sales, the HR tools for recruiting, and so on.

But workflows are more than data — they also have human elements like collaboration and enforcement. That’s why we’ve seen a recent explosion of web-based productivity tools like Monday.com, Asana, and Basecamp, which aim to manage both aspects of our workflows. Most of these tools still orient around data rather than conversation. Hence the need to shuttle back and forth between data management tools and conversation tools like Slack and email, as well as the need for process experts (project managers) to make sure things don’t get too jammed up.

Which begs the question: Why can’t we have both?

How we got to here: The evolution of workflow tools

To visualize a better future for workflow management tools, let’s first chart how we got to today. And before that, let’s align our understanding of what a workflow is. Merriam Webster defines it as: “the sequence of steps involved in moving from the beginning to the end of a working process.” But that doesn’t tell the whole story.

There are certain key characteristics that all workflows share And there are two critical driving forces behind any functioning workflow: documentation and enforcement.

Key characteristics:

• There’s always an asset. That’s the “thing” that is being passed along from person to person and phase to phase. For example, a piece of writing, or a product in development.

• State is important. The current condition of the asset — in progress, awaiting approval, rejected — is important because it conveys its current condition to the various people that care about how the world of assets is doing.

• The asset changes as it traverses a workflow. Most assets that move along a workflow have a core set of attributes that they carry throughout. A story will have a headline and a byline. A job candidate will have a name, address, and résumé. Still, as an asset moves along a workflow, it evolves and often increases in complexity. For example, a sales lead may start with a name and phone number, but over time that package inherits all sorts of information: email threads, communication notes, a proposal, a contract. As the asset moves along the process, it adapts and changes as other actors get involved.

• There are almost always exceptions. If there is no opportunity for exceptions in a workflow, then it’s probably already been automated. When you click “Purchase” at checkout, a cascade of processes kick off with zero human involvement. Even exceptions are handled in an automated way (e.g., credit card rejected). Often, human judgment is in play (editor hates that opening paragraph), so you can’t automate it. 

• It’s repeatable. There will be many stories that will go through a similar workflow. Some will go through more rounds of editing and some will require more artwork, but the workflow is repeatable. 

• There is pressure. This one is tricky. Zooming out, all workflows are driven by the inherent need to keep moving things forward. Zooming out even further, the organization suffers and is under threat if things don’t move along to some form of resolution. Some who are participating in that workflow don’t care much about that time pressure. You often hear about the editor chasing the writer for a draft. The writer, paid by the word, knows about the deadlines, but they’re not feeling the heat as much as the editors.

Documentation: The Spreadsheet

In the 1970s and ’80s, the world’s first workflow tool took hold: the spreadsheet. The spreadsheet, originally intended as the digital equivalent of an accounting ledger, was appropriated as an incredibly effective way to track a bunch of things. It’s incredibly powerful and simple. Rows and rows of stuff that need to keep moving. You can put in due dates and sort by due date! You can color the late packages in blood red! It’s a great way to get things done.

The spreadsheet’s table format inspires most workflow software today, and the data that powers that software. It is how computers, to this day, deal with information. Grids of information allow for easy storage and retrieval. For humans, grids provide the illusion of order. Neatly aligned bits of information are simply easier to track.

Many of these tools reinforce this grid-centric approach to working. Yes, when something needs attention it can change color (red means now!), but for the most part, boxes with stuff in them (table, kanban, and so on) is the way to go.

Still, there was one massive gap that neither spreadsheet nor today’s workflow tools ever addressed: enforcement. Excel did a great job of putting things in nicely stacked boxes, it just didn’t have the mechanisms to enforce the processes that lay within. Someone has to hunt down and prod the various participants in any workflow to do their part. Otherwise, things get jammed up.

Enforcement: The Project Manager

A project manager’s goal is to ensure the right people are paying attention to the right things and carrying out their part of the process on time. The project manager has to take documentation (rows of data) and turn it into communication. Ideally actionable communication. Illustrated, it looks something like this:

Because humans don’t communicate in grids, the work of getting things done is powered by talking to one another. On the other end of this spectrum are wildly popular tools like Slack and Microsoft Teams. It’s where the real magic happens.

Enforcement is an inherently human skill. Many of today’s workflow tools provide powerful integrations so that when certain criteria are met in a workflow (e.g., moved from stage 3 to stage 4), an email gets fired off, a team member gets a notification on their phone, or a Slackbot lights up. They’re all great ways to get people to pay attention, but that’s not enforcement, because a machine is doing the asking. Too many pings and nothing feels important anymore. To this day, the single most powerful way to move that package along the process is through human interaction.

“I’ll meet you at row 55839”

The journey of productivity software is a journey out of software itself. We haven’t yet bridged the gap between documentation and enforcement, data and conversation: The talking happens in email and chat and the data lives in the boxes. Most tools still orient around data rather than conversation. And the conversation tools focus on reinforcing the social dynamics that make work tolerable and sometimes fun.

The best tools today tend to lean on metaphors. Email is replete with envelope icons. But the challenge of workflow lacks a high-fidelity metaphor because it’s actually a mess in real life. Inventing tools sometimes requires design thinking that leaps beyond known conventions. It’s part design and part anthropology. Technology is more than ready for the task. We just need to think beyond the boxes.

Rich Ziade (@richziade) is Co-Founder and President of Postlight. Drop him a note at rich.ziade@postlight.com.