Tooling the modern organization


In my work as both a product manager and as a consultant, I’ve been part of many cross-functional teams. It seems like the work often comes to a point of chaos where I find myself saying, “ugh, let’s just all get in a room together and move through the work.”

Even though I’ve done it tons of times, I still find myself caught off guard by how effective space-sharing can be for project progress. I don’t mean meeting about the work, I mean pulling people together for a work session. An hour or two with the team in the same room gives us all alignment, the ability to solve issues quickly and with clarity, and it lets everyone see into everyone else’s processes.

This is because, instead of paying lip service to cross-functionalization, we’re actually working as a unit. We can make the progress in a few hours that otherwise might take weeks of throwing work over the walls to each other, waiting for reviews, responses, and approvals.

This scenario should feel familiar to those in the “future of work” conversation — it’s basically a description of open work practices and why they can be beneficial. We know that teams with default access to quality work and reference information between members make better decisions, but the means for actually accomplishing that other than “getting everyone in the room” might not be very intuitive.

I’m going to suggest some ways that teams can leverage simple, off the shelf tools to achieve the “in the room” effect, even if they are distributed or asynchronous.

A Note on Tools

Before we get too in depth, I’d like to make a note related to the tools I’m suggesting. I do not believe that the barrier to better organizational behavior is primarily technological, and as such, I do not believe that any of these tools is a silver bullet. Buying and adopting the brand names in play here will not make you more responsive or open or Agile or the buzzword du jour.

The crux of the discussion is how they are being used. The reason I’ve selected the brands that I have is because they are either easy to adopt (Trello), or are relatively standard in the industry (Slack). There are other options for every tool, and teams choose their own way of working. Feel free to experiment with different tools and share your experience in the comments.

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A Basic Structure for Work: Conversation, Workflow, and Version Control

Imagine a team collaborating on work. They are probably sitting around a table, talking about ideas, recording them on sticky notes, maybe even putting them on a Kanban/Scrum/workboard. Then they stack things they’ve produced (paper prototypes or agreement documents) into piles, throwing out outdated versions. But no matter what they’re working on, there are going to be three basic types of systems (and supporting tools) in use:

Conversation Systems: a semi-refereed means of discussing the work between team members

Workflow Systems: Methods for processing conversation and ideas into outputs or next actions

Version Systems: Repositories and practices for managing and maintaining the team’s outputs

Any tools we adopt should serve to recreate at least the level of productivity a disciplined team with a suitable process will achieve working in a room directly with one another. At best, tools should enhance that work and allow it to be extended into non-shared room formats.

When setting up your system, keep the following ideas in mind

  1. Make tools talk to one another automatically (persistence). The system should take updates to any part and automatically reflect those updates in the other parts of the system, preferably accompanied by some sort of message about the update. Opposite: systems where we manually update each part to reflect current status.
  2. Maintain a single source of truth (SSoT). There should be one source for any file, which is shared, standard, and updated at every save and change made by any user with access. Ideally there is only one (current) version of the file in view in that system. Opposite: systems where tons of different people edit their versions of files locally, save, and send them back to the shared drive. This results in what we often call “version explosion.”
  3. Store configuration in the system. As the system gets used and tested by the team, subtle norms about usage will emerge that aren’t as important to make standard across every team, but that let each team move quickly and clearly. Those norms should be stored in an easy to access place, within the actual work environment. Opposite: A large, complex, tough-to-change list of rules gets referenced by a leader but no one really is sure how it is standardized or where it is kept.
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A system overview that uses Slack, Trello, GDrive, and Dropbox. Arrows indicate the direction that automatic updates can be pushed.
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A Simple Work System: Slack + Trello + Google Drive + Dropbox

Here is a way to set up a system using tools that require very little beyond an internet-connected computer, phone, or tablet to start using.

For Conversation: Slack

Slack is a simple but powerful digital workspace for teams (if we use it incorrectly, however, it’s just a chat tool). We can set it up to integrate perfectly with Trello so that changes made in either place persist between the two, and there are nice import tools for both Google Docs and Dropbox that make simple link-pasting actually store files in the chat history.

For Workflow Management: Trello

Trello is a simple, free “board” tool that is flexible enough to reflect any number of different workflows, from various Agile standards, to holocracy, to dead simple “To Do, Doing, Done.” When properly set up, comments, changes, and file additions automatically post to Slack, so team members who aren’t looking at the board are notified as things change in the workflow.

For Version Control: Google Docs for Collaborating on Content & Dropboxfor Sharing Files

Two tasks regularly come up when we talk about document management: creation and storage. In this system, we’ve broken them apart to emphasize that different tools can be used for each purpose.

Google Documents offer us a simple way to collaborate on most types of work artifact, and at The Ready, most of what we produce begins as a Google Doc, Sheet, Slide, or Drawing.

If it becomes something with more robust design requirements, often the standard tools (Keynote, inDesign, etc) work best natively on an individual’s machine, so we use something like Dropbox to share and maintain the file. Both of these things integrate directly with Slack and Trello so that links, rather than uploads, can be shared.

Connecting Everything Together


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Is your friend in Slack.

To set up this system well, after you have registered for each of the tools the first thing that you should do is add the built-in integrations for Trello, Google Drive, and Dropbox.

Note that Trello has two integrations, so you’ll want to use the Trello Alerts one and then select the types of things you want to be notified about. Play around with this to find the right amount of signal, but here is what Sam Spurlin and I use in a channel we share:

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To maintain a Single Source of Truth, use programs like Dropbox and Google Drive.

By sharing links to GDrive or Dropbox, instead of directly uploading files, we let the actual systems always represent the current version of our documents, rather than having to save and replace, or worse, manage some complex version control nomenclature.

So, rule: share GDrive and Dropbox links; don’t upload directly from your desktop.

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Sharing a link to an Omnigraffle file from MacOS by control + clicking
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“The most efficient and effective method of conveying information to and within a team is face-to-face conversation.” I remember reading those words many years ago and not fully wrapping my mind around them, but as I’ve worked more and more with distributed teams they ring very true.

There is nothing quite like “being in the room,” but properly leveraging modern communications and alignment tools can move us in that direction without requiring anyone to jump on a plane.