Never Skip Retros

The Overlap #4

Photo source: Elizabeth Goodspeed

Welcome to The Overlap, a newsletter that explores the intersection between product management and organization design. 

Every team should have a retrospective practice

“We’re looking to be more agile. What’s the first thing we should do?”
“We’re a new team. What meetings should we put in place?”
“I want to transform this company. Where do I start?”

My usual answer to all three questions is this:

Start doing retrospectives.

I don’t typically prescribe a specific method to a team. I encourage teams to come up with their own solutions because their solutions are informed by their knowledge and insight of the organization, rather than something they pulled from a Medium article. I try to stay method agnostic.

However, there is one practice that I am adamant about: retrospectives. Regardless of your team’s way of working, they should have a regular retrospective practice. Here are three reasons why.

Reason #1: Retros disrupt the habit of anticipating the future.

Large or small, early-stage, or Fortune 500, most meetings in most companies are future-looking. 

“We need to align on what needs to get done.” 
“Let’s hash out our next steps.” 
“What’s our roadmap?”
“What’s our strategy?” 

Retrospectives are the only meeting that empowers teams to look backward instead of forwards.

It's rare for teams to compare what actually happened (after launch) to what they thought would happen (at kickoff). Because they’re onto the next thing! But without comparing our initial hunches with reality, we won’t learn as a team. And nothing is more valuable than learning as a team. Learning as a team builds psychological safety: the feeling of being able to say what you mean without fearing judgment or negative consequences.

Reason #2: Retros are low hanging fruit.

Compare retros to other tactics like...

  • giving every team a product manager, scrum master, and agile coach

  • implementing an end-to-end management framework like Holacracy

  • switching one documentation tool for another

While each of these tactics has its own benefit, it will take a while until we see benefits. There's a lag between doing the thing and seeing results from the thing. That lag is discouraging to teams trying something new. I want your team to see benefits immediately so that they get a sense of momentum from the start. Retros produce an immediate benefit.

All it takes is a calendar invite and a shared commitment to attend. And trust me, you will be tempted to skip a retro when that calendar invite is approaching. “I feel super busy, and could use that time to get my work done.” That is a trap. Don’t skip retros.

Reason #3: They put teams on the path to continuously improve.

Every product development framework boils down to continuous improvement. The best teams learn quickly and inexpensively and adapt based on what they learn.

From Reflection is what counts:

It’s often said that the retrospective is the hallmark of agile in the sense that it typifies the ethos of inspect-and-adapt and improvement that transcends any particular framework, practices, or tools.

If a team isn’t sure how to begin their journey of continuous improvement, retros are the best place to start.

So whether you’re team is kicking off, tweaking its way of working, or embarking on a transformation effort, start doing retros. Creating long-lasting change can feel vague, amorphous, and overwhelming, but retros will give you and your team clarity on what needs to be done next.

Some of my go-to resources for facilitating retros

  • Parabol: the best tool out there for facilitating remote retrospectives. Trust me. Parabol cares deeply about making meetings great and their product shows that.

  • Fun Retrospectives: a library of tons of retro formats. Go here when you need inspiration for your next retro.

This issue's reads

1/ Uncommon metrics that say a lot about your company - Tim Casasola 👋🏽

Inspired by this tweet, I was curious why many companies don't track metrics around distributing authority, customer focus, diversity, and compensation fairness. So I wrote a 2-minute read about it.

2/ Plantations Practiced Modern Management - Harvard Business Review

Here’s a hard pill to swallow: slave plantations practiced scientific management. In the 1840s, planters were depreciating their slaves, determining their market value, and assessing their productivity. These practices are eerily similar to common management practices today. All the more reason to question Frederick Taylor and his influence on management.

3/ Navigating Power & Status - Tom Critchlow

Great piece on navigating organizations. It’s written for independent consultants, but its lessons can be generalized. It’s hard for PMs to get things done unless they’re aware of the power dynamics at play.

4/ The Amazing, Shrinking Org Chart - Venkatesh Rao

 “The collapse of organization charts in our thinking reflects a deeper collapse of the underlying imagined organizational realities. The organization chart is shrinking because we are slowly recognizing what has always been true: there is much less ‘organization’ to chart than we’d like.”

5/ Feature Team Adoption Map - LeSS Works

I’m a big fan of any model that helps teams understand where they’re at and what they must do next. Yes, maturity models assume linear growth, and linear growth isn't how growth works. But these models are useful in that they build a team’s awareness of where they’re at today and how they want to improve. In my view, a team that’s aware of where they’re at and where they want to go next beats a team that’s striving towards a theoretical, unreachable ideal.

6/ The Slack Social Network – Stratechery

Slack and Microsoft Teams are similar products with entirely different strategies. Microsoft is focused on being an all-in-one product for enterprises, while Slack is focused on improving the enterprise-to-enterprise experience—shared channels being an example of this. 

See you in two weeks.
–tim

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