I spend a lot of time reading books and listening to podcasts and every once in awhile, I come across something that hits me so hard that I have to drop everything and write about it.
This is one of those times.
I actually had a post ready to go for this week on remote work and mental health that I had to bump in favor of writing about Aaron Dignan’s recent interview on The Knowledge Project podcast.
If you’re not familiar with Dignan’s work, he has written a book called Brave New Work and is the co-host of the podcast by the same name. There are likely 100 pieces of content I could point to as “must reads/listens” in his back catalog, but this interview tops my list. The combination of Shane Parrish’s probing questions and Dignan’s concise and actionable insights pack a punch that forced me to rewind over 100 times to write down a note (I counted).
So, while I implore you all to give the full podcast a listen, I also wanted to share some of those notes with you, intermixed with a few of my own thoughts.
You’re only as effective as the honesty of your feedback loop
I’ve never met a leader who doesn’t say they want feedback. Every leader worth their salt knows what they’re supposed to say about getting feedback from their teams… But I’ve met a ton of leaders who actively bristle when they receive negative feedback.
The result is predictable… It looks something like this.
Give it a couple of years and before you know it, you’ll be surrounded by two types of people… Sycophants and people who know better than to bring you bad news.
This creates a toxic feedback loop. Leaders are no longer receiving feedback that’s representative of reality and their decisions are impacted. They can’t make decisions rooted in reality because their worldview isn’t rooted in reality.
“We’re trying to steer dynamically based on the feedback we’re getting… but if you live in a system far removed from feedback, it’s problematic. Or, even worse, if the feedback you receive is disconnected from reality.”
Aaron Dignan
This is why seeking dissent is such an essential tool in an effective manager’s toolkit, especially in a remote-first setting where our feedback loops can become even more insular than they were before.
The foundation of an effective decision-making process is establishing a shared, even if not fully unified, view of reality. Leaders who struggle with this will fail in remote-first contexts more than in-person contexts because of how divergent their teams’ work experiences can be compared to the controlled environment of the office.
Navigating Complicated vs. Complex Systems
“You’re yelling at the weather.”
This line from the podcast interview made me guffaw because I’ve seen it play out before, but I’ve never had the language to articulate what I’m seeing.
Dignan broke down systems into two types… Complicated and complex.
Complicated systems are predictable. There’s a clear cause and effect and they behave consistently. When problems arise, it’s easy to solve them in a logical and linear fashion. When my car breaks down, I bring it to the dealership and they fix the part that isn’t working. The car behaves the same way every time. No surprises.
Complex things aren’t as predictable… They’re dispositional. They don’t have a clear cause and effect, but rather trend in one direction. You may be able to see where they’re headed, but you can’t tell for sure how they’ll react to a stimulus. Think of the weather or a toddler. You can predict how a complex system might react, but there’s less certainty.
When business leaders bring a complicated lens to complex problems, things tend to go poorly. Instead of checklists and formalized procedures, which are the lifeblood of a complicated system, leaders need to approach complex systems with open ears.
As Dignan says, “We can’t describe complexity from one perspective.”
The systems best equipped to handle complex problems are NOT focused on ensuring flawless execution, they’re focused on consistently increasing capability and learning. Anti-fragile systems need to make trade-offs between short-term execution and long-term learning in order to remain healthy.
Running a Great Retro
There is nothing more painful than an ineffective retrospective.
I’ve spent dozens of hours in retros that fail to clear even the lowest possible bar of insight synthesis. I’ve also spent time in amazing retrospectives that are dynamic, engaging, and challenging. Once you’ve seen the difference, it’s impossible to go back to a terrible retro without wanting to pluck your own eyes out.
But something’s always vexed me about retrospectives… Why is there such a stark difference between the great and the mediocre? Retrospectives seem to act more like sushi than pizza.
Even bad pizza is pretty good, but sushi is either great or causing you digestive problems.
The breakdown Dignan did of his team’s retrospectives at the end of this interview provided a great overview of what makes the best retrospectives work. He broke it down into how your culture acts before, during, and after the retro.
Before
“If you don’t have a culture of authentic communication… You can show up to the retro and everyone’s clenched or tight. But if you have a culture of constant feedback, then when you get to the big one, the air is out of the balloon and now it’s safe.”
Aaron Dignan
This resonates with my experience. You want the team to come into the retro with an open mind and a sense of honesty and vulnerability. This isn’t the time to defend your work or feel attacked. This is when we come together to unpack what happened.
During
“It’s really easy to have a retro that’s boring and stale and asks a question that doesn’t provoke… If I don’t see conversation happening while I’m facilitating a retro, that’s my first clue that we’re not doing the right stuff.
You want burstiness in the conversation where people are talking over each other. If you don’t see that, you need to change the question or participants.”
Aaron Dignan
I’ve been in both of these retros… I’ve been in the silent one where one person talks the whole time or we take turns parading our work like a dog and pony show. I’ve also been in the retros where people are so excited to share their insights and build on each other’s ideas that they can’t help but interrupt one another.
Great retros poke, prod, and provoke. They uncover insights that would remain hidden without careful inspection. They connect ideas that would remain separate. If your retros aren’t accomplishing that goal, your facilitator is to blame and something needs to change.
After
“What do you do with the insights? That’s where most teams really fall down. Most teams have really great insights and then it kind of goes on the cutting room floor to die.”
Aaron Dignan
As much as I loathe drawn-out, boring, stale retros, I hate inaction even more.
When we spend multiple hours of the team’s time reviewing something and nothing changes at the end? I want to jump through the Zoom window and slap some wrists. Great teams deserve better than this ineffectual bullshit. That’s where Dignan’s passion currently lies with his startup, Murmur.
The way he referred to this was by talking about moving away from the “to-do list” space, which is perpetually bloated and being delayed, and into the governance space. Instead of ending this meeting with a list of actions we should take, how do we end with a few agreement shifts that can improve the way we work together?
After all, leaders are responsible for how we work. If that’s not being deliberately designed in your organization, you deserve a more intentional workspace.
Tim Hickle is a marketing leader who helps high-growth startups and scale-ups get unstuck and hit their goals while embracing AI and the future of work. To learn more about how Tim can help your organization grow, visit TimHickle.com