Leading Teams and Delighting Customers

Category: Articles

Longer-form opinions, ideas, and how-to’s that I’ve shared here and elsewhere.

Build Your Own Red Team

At some point or another, I’d imagine virtually all of us have answered some form of the “money is no object” question. Essentially this: If you didn’t have to worry about money at all, what would you do?

My standard reply is to open some form of bookstore and coffee shop.

There would be no WiFi, and we’d stack the whole place with good old-fashioned physical books. If we want to get really specific, I’d name it “Penny University,” a callback to English coffeehouses in the 17th and 18th century. Oh, and we’d have monthly discussions where we call in experts to debate both sides of a “hot topic” (education, politics, poverty, future of work, etc).

I’ve thought about this a lot!

As much as I love this idea though, I’m probably not going to open a bookstore. The whole thing just feels so risky, especially as we talk about a worldwide pandemic (setting aside the ebook vs. physical book discussion).

Imagine my shock and delight when I read about Ryan Holiday’s new bookstore outside of Austin, Texas—The Painted Porch. He wrote a piece for the Texas Monthly aptly titled “Opening a Small-Town Bookstore During the Pandemic Was the Craziest Thing We Ever Did.

Sounds accurate.

The whole experience was fascinating, but one piece stuck out, what I would equate to a version of red teaming:

Whenever I’m considering an idea I’m excited about, I like to ask friends to talk me out of it.

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Listen, Learn, and Help. Then, Lead.

I’m constantly drawn to leaders in military settings. I suspect it’s because of the immense gravity surrounding their specific situation.

It’s hard to fathom what it’s like to lead a country being bombed on a nightly basis like Churchill or finding a way to stay positive when you’re facing a seemingly dominant adversary with a dwindling force and no money to pay new recruits like Washington.

These situations only magnify the importance of great leadership, which makes them all the more useful for us to learn from.

Recently, I finished reading Call Sign Chaos by four-star General James Mattis and Bing West. The book traces Mattis’ 44-year career through the Marine Corps and the various leadership lessons he learned along the way. Outside of the direct experience he gained leading millions of troops in battle, Mattis is a voracious student of military history.

When someone with this much experience offers to share their knowledge, it’s not a bad idea to listen!

Mattis continually referred to the “Listen, learn, and help. Then, lead” leadership style attributed to George Washington. This approach provides a helpful contrast against the typical power-hungry

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Taming Your Advice Monster

For the past few weeks, I’ve been going through an internal workshop at Zapier called “Coaching For Performance.” I have many takeaways that I’m trying to implement in my own work. By far the most difficult strategy though involves “taming the advice monster.”

I imagine you’re familiar with this concept already. The advice monster frequently rears its head when someone approaches you with a problem. You listen patiently for a minute or two and then immediately begin offering up your advice.

Because, obviously, you have the solution, and they need to hear how awesome it is!

Maybe a solution is exactly what the person was looking for but probably not. Maybe they just wanted to talk through the issue and be heard. Maybe they wanted your feedback on a specific piece. Maybe they could come up with a solution on their own.

Engaging your advice monster has some obvious negative consequences:

  • You’re robbing the other person of a learning opportunity. Giving answers works in the short-term but not in the long-term.
  • You’re reducing their sense of autonomy. Instead of empowering them to resolve their own issues, you’re creating a bottleneck where you’re the answer provider.
  • You’re sending the subtle message of “You can’t figure this out yourself.”

The list goes on!

These downsides are obvious. You and I both know better than to continually engage our advice monsters. So, why do we do it constantly?

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Make Your Work Easy to Find

It feels like a gross understatement to say that the pandemic has changed the future of work.

Unemployment, remote work, shifting industries…you get it. I’m not saying anything you haven’t heard about many times over already. I do want to drill down on a particular aspect of leading remote teams though. How do you know when anyone is getting work done?

In an in-person office, we start with the assumption that if you’re at work, you’re getting work done. Rightly or wrongly. Even if you accomplished nothing during the week, you could say, “I was here.” (Bad) Leaders can therefore fall back on “butt-in-seat management” wherein visible attendance equals valuable output.

This obviously gets trickier in a remote environment! There isn’t an “office” to show up to on Monday morning. Sure, most companies have some kind of communication tool like Slack. Unless your leader is really nosy though, they probably have little idea when you’re actually around.

So, what do leaders do? And, how can we, as teammates, help?

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Could We Go Faster?

Recently, I came across Patrick McKenzie’s blog post about working at Stripe. He breaks down why he feels like Stripe has been able to move faster than most other companies of the same size.

There are obviously many factors at play here including organizational policies, team structure, communication norms, hiring…the list goes on. I really loved this line of questioning though:

I have seen truly silly improvements occasioned by someone just consistently asking in meetings “Could we do that faster? What is the minimum increment required to ship? Could that be done faster?” It’s the Charge More of management strategy; the upside is so dramatic, the cost so low, and the hit rate so high that you should just invoke it ritualistically.

Most organizations operate at nowhere near the frontier of their capabilities. That is a choice, and strikes me as a valid choice, but you can choose to move closer to the frontier, too.

What Working At Stripe Has Been Like, Patrick McKenzie,

There truly is very little downside in asking the simple question “Could we do that faster?”

That question has been bouncing around in my head for quite some time specifically as it relates to my role in leading people and teams. How can I create an environment that increases the cadence of our team? What obstacles commonly get in the way? How can we avoid them?

Here’s a non-exhaustive list I’ve compiled on why teams move slower than necessary and how to address each.

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Foundational career skills

Or, as an alternative, wordy title: The Theoretical Pyramid of Professional Development.

Today, I want to chat about career skills, but if you’ll spare me a moment for a quick digression, I’d like to wax on about a completely separate topic: CrossFit. We’ll tie this all together here momentarily.

Courtesy of CrossFit.com

One of the fundamental principles in CrossFit is communicated through a pyramid, specifically the “theoretical pyramid of athlete development.”

Nutrition exists at the base of the pyramid followed by metabolic conditioning (aka cardio), gymnastics, weightlifting, and finally, sport.

This pyramid has a few different implications as we’re looking at athletic development over the long-term, the primary one for today being:

Your success at any given level is predicated on how well you’ve developed prior levels.

For example, your weightlifting capacity will be impacted by poor nutrition. A solid conditioning base will improve your gymnastics capability. And so on.

Let’s bring this all back to the professional arena.

A few recent experiences1 have caused me to think about what professional development pyramid would look like. Meaning, if our goal was long-term success and fulfillment throughout our career, what kinds of skills would form the backbone of that success?

I’ve listened to two podcasts on the topic and chatted with some managers at various companies during a recent conference I attended. Here’s a tentative list I’ve come up with in no particular order.

  • Effective Communication—This is critical regardless of whether you’re working with a team, sharing timelines with your boss, or chatting with a potential customer. Can you articulate your ideas in a clear and concise manner both verbally and textually? One may be more important than the other depending on context.
  • Reliability—Can I count on you to do what you committed to doing to the level that you promised on the timeline we agreed to with minimal follow-up? That sounds like a doozy, but it really is a core skill. If any of the components (delivery, scope, or timeliness) has to slip, do you communicate that as early as possible?
  • Organization—It doesn’t really matter if you use the latest productivity app or a notebook and a pen. Can you effectively plan out your day/week/month to deliver results? If you’re tasked with something during a meeting, do you have some method of recording that so you don’t have to be reminded?
  • Focused AttentionCal Newport has literally written books on the importance of focused attention. I’d direct you to Deep Work for starters. The ability to concentrate all of your talents on the most critical task at hand for long periods is critical for accomplishing anything of value.
  • Humble, Adaptable Mentality—Can you take feedback on your work? Are you open to debating points of view on a certain issue? If we move forward in the direction opposite your viewpoint, can you adapt and come along? Are you up for tackling new things, even if you might not excel in the beginning?

These skills form the foundation on which you can build specific skills like learning JavaScript or data analytics. If you focus on the specific skills first though and ignore the foundation, you’re shortchanging your future self.

Tying this all together then, if we built out our own pyramid of professional development these skills would sit at the bottom. I feel like this is important primarily because it’s easy to interview for and focus on developing the career-specific skills that look good on a resume. These foundational skills are harder to tease out in an interview, which is one main reason I love the trial interview process at Automattic.

Don’t steal success from your teammates

Time for a scary admission: I can be a bit of a control freak.

For the longest time, if I was asked about my biggest weakness, I would say just that – I have a hard time letting go of control especially if we’re talking about managing a project or a complicated task. I was the kid in school that preferred to work by himself rather than in a group (yeah…that kid). I knew I would do the project correctly. Someone else? They might screw it up.

As a result, I’d pile on tasks even if I was overwhelmed. If I took it on, I knew it would get done. That was all that mattered! If I did hand something off, I’d be sure to provide step-by-step instructions on how to get it to the finish line.

This might be a bit of an exaggeration. I’ve been steadily trying to get over this fear of letting go especially after I read Marshall Goldsmith’s What Got You Here Won’t Get You There. I’ve gotten better at handing over tasks and allowing others to run with ideas. Still, it’s an area that I’m constantly trying to work on – how to delegate effectively and allow others to crush projects on their own, without my needless meddling.

This concept of effective delegation popped up again recently as I read The 7 Habits of Highly Effective People. One of the habits (Put First Things First) spoke to this idea of delegating ideas. It broke down two types of delegation – Gofer and Stewardship – and described how the former steals success from teammates while the latter empowers them.

Let’s dive in.

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The critical roles of a leader

In Good Boss, Bad Boss, I came across this definition of what it means to be a leader:

A boss’s job is “to eliminate people’s excuses for failure.”

The author, Robert Sutton, went on to distinguish two aspects of a leader. The first aspect is to manage and oversee performance meaning are you doing everything possible so your people can do great work? The second aspect involves humanity. Are you helping your people “experience dignity and pride” in their work?

If you Google “definition of leadership,” you’ll get over 500 million results, each highlighting a different aspect of what it means to be a leader. Some keep it short and sweet in a single sentence. Others list out 10 commandments leaders should follow.

I believe the true definition of leadership is a personal one, and it’s unique to each individual person.

Over the past few weeks, I’ve had the same conversation with multiple people. In those conversations, I defined the three characteristics I believe make up a good leader so I wanted to share them here.

My personal definition of leadership is that it involves three pieces:

  1. Setting the vision for where your team is headed.
  2. Providing actionable feedback to help them get there.
  3. Developing your people by connecting them with opportunities for growth.

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The toxic tandem in leadership

“Followers look a the leader; the opposite does not happen as regularly or intensely.”

The above is from Good Boss, Bad Boss. It’s a quote by anthropologists that study group dynamics among chimpanzees, gorillas, and baboons. These species are unique in that they have a set power structure. They have alpha males and leaders among their ranks.

Anthropologists studying these groups noticed something unique:

Studies of baboon troops show that a typical member glances at the alpha male every twenty or thirty seconds.

Followers revere the leader of their group, assembling cues on how they should think, feel, and act. Psychologist Susan Fiske elaborates on why this might be the case:

In an effort to predict and possibly influence what is going to happen to them, people gather information about those with power.

This makes sense. If someone has even a small stake in your future, it’s in your best interest to understand how they think and respond in specific situations.

This wouldn’t be a problem if leaders were always conscious it was happening and acted accordingly. But, that’s not always the case. There’s plenty of evidence that power warps the awareness, thoughts, and attitudes of those that have it*.

The overarching themes are laid out in Good Boss, Bad Boss. Leaders tend to:

  1. become more focused on their own needs and wants
  2. become less focused on others’ needs, wants, and actions
  3. act as if written and unwritten rules others are expected to follow don’t apply to them

The “toxic tandem” is this: Leaders are under intense scrutiny from those around them yet their position often results in self-serving behavior.

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