Embracing Imperfection

Communication in the Bot Age

To keep pace in realtime workplaces, the most effective teams will need to flex effortlessly between structured & free-form communication.

With platforms like Slack, what was once a company-wide productivity mandate is now a series of team-level decisions. Instead of being bound by absolutes, bots grant us the flexibility to create our own workflows and conventions.

This dramatic shift from one-size-fits-all systems to AI-facilitated experiences will make us question how and why we interact with each other.

As we set out on this journey, we should be careful not to lose sight of what makes us human.

A Natural Beginning

In a small team, we’re likely to embrace flexibility by adopting what feels natural, like a weekly priority meeting or daily stand-up. These add just enough structure to coordinate efforts while keeping an open team dynamic.

Everything goes swimmingly until the team starts to grow and something pokes at our imperfections.

We get mixed up on priorities or drift out of sync with each other because, after all, we’re human.

For something so inevitable, our reactions can be a bit dramatic:

Human faces talking to human faces in realtime? What is this, the dark ages? If only we had a process…

That’s when complex “productivity” systems start to look appealing:

• Planning work? Write a detailed user story and estimate the level of effort in points. Oh, and cross-reference team capacity with velocity
• Started work? Assign the ticket to yourself and set the state to “in progress,” then update your team somewhere else
• Completed work? Mark the ticket as “Resolved” — or is it “QA”? I think it’s “Done” but you should probably ask the Owner to review anyway

Woah, what happened?

In a Faustian bargain, we traded our imperfect, but natural communication for complexity in the guise of productivity.

These systems delude us into thinking our desired outcomes are already known as fixed points on the horizon. With our path clearly charted, we’re encouraged to abandon our diverse set of tools and activate autopilot.

The State is a Lie

In theory, these complex systems promise that maintaining all of this “working state” will make teams more effective. However, in practice, the true benefit lies in their communicative side effects:

• Subjective story point estimates are primarily used as discussion starters for scope, alignment, and definition of done
• Ticket state changes can help notify people of milestones and exceptions (even if they’re stuck “in progress” hours after being completed)

The side effects are valuable, but the means are unnatural overhead that impede communication and make us feel like machines.

As our communication filters through these complex systems, our team culture becomes less about a safe place to work together and more about keeping the system up-to-date.

Why we Stand-Up

Let’s bring things back to our starting point: doing what’s natural.

In my experience, teams that abandon these heavy methodologies usually keep their daily stand-up ritual. Why?

Stand-ups calibrate our work by grounding it in reality.

They’re a place for us to:

• Say good morning
• Raise exceptions and ask questions
• Triage emergent work
• Discover serendipitous relationships between projects
• Adapt if a teammate is sick or priorities change
• Resolve blockers
• Decide where to eat lunch 😎

It feels natural to discuss any of these topics because expectations are deliberately communicated up-front.

Over time, this structure is codified in group norms that promote psychological safety, a cultural trait that Google found critical to making a team work. We know this intuitively: when people feel like they have a forum to say something without getting shot down or breaking decorum, the team is more effective.

Unfortunately, not all teams are structured this way.

A recent HBR article on Collaborative Overload summarized that “up to a third of value-added collaborations come from only 3% to 5% of employees” and that improvements would require “resetting social norms.”

So, there’s an opportunity to be more effective if we can figure out how to encourage safety through social norms, like stand-ups. But, we also want to avoid rigid overhead that impedes our communication.

Where should we turn?

Uncharted Territory

What if we could adopt dynamic conventions and working structures while communicating naturally with one another?

Beating bureaucracy isn’t just one more re-org. What’s needed is an approach that’s emergent, collaborative, iterative, and inescapable; one that “rolls up” rather than “rolls out;” something more like an open innovation project and less like Mao’s cultural revolution.
- Gary Hamel and Michele Zanini, Harvard Business Review

To “beat bureaucracy,” we need to change our relationship with machines, starting by ditching the notion that we should be more like them.

Machines are designed to handle state, organize information, and present it in context based on relationships. People are good at assigning relevancy, deriving meaning, and uncovering insights from well-organized information.

There’s a clear partnership staring us right in the face:

Let’s embrace our imperfect communication and leave the structure and overhead to bots.

At Awesome, we believe bots should create an invisible layer of structure that frees us up to focus on outcomes and relationships.

By offering a clear set of tools to stay in sync, document decisions, and uncover insights, Awesome makes teams more effective right where they communicate.

No magic, just facilitation of structure when you need it.

That way you can focus on what matters: being awesome to each other.

You can invite Awesome to your Slack team right now: