How to Effectively Delegate and Avoid Stealing 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 3 Foundational Roles of Successful Leaders

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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A Comprehensive Look at How to Give Better Feedback

A woman sitting on one side of the table as she receives feedback from two individuals

A few months back, I published some notes from a presentation I gave at Automattic all about why receiving feedback tends to sting. While everyone is focused on developing the skill of delivering feedback, I truly believe becoming a better feedback receiver is worth spending some time on. The skills go hand in hand. While you can’t always control how feedback is delivered to you, you can control your reaction to that feedback.

Still, there is an art to delivering feedback. When delivered appropriately, feedback can grow the relationship you have with colleagues, teammates, and even friends/family. When delivered inappropriately, it can create animosity.

If you remember the three types of feedback triggers, you’ll know that the three reasons feedback tends to sting are:

  • Truth triggers – We’re upset by the substance of the feedback. It’s unhelpful or simply not true.
  • Relationship triggers – We’re upset by the dynamics with the feedback giver. Either we feel mistreated by this person or we feel as though they’re not in a position to give us feedback on this particular topic.
  • Identity triggers – The feedback we’re receiving conflicts with our own internal narrative.

Similar to receiving feedback, I led a workshop awhile back at Automattic on the topic of giving feedback. Here are some extrapolated notes from that topic. They’ll address specifics like:

  • Feedback comes in all shapes and sizes. We’ll talk about the three specific types of feedback and why you’re likely falling short on one of them.
  • Now that I know why colleagues are set off by feedback, how can I tailor the feedback I’m giving to avoid the three triggers mentioned above?

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Be Unnecessary (And Two More Tricky Leadership Principles)

I’ve been reading, learning, and writing a good deal about leadership over the past two years. It’s one of my favorite topics because the applications expand far beyond your business career into your personal relationships, family, and more. Regardless of whether you’re in an official leadership position within an organization, you’ll benefit greatly from developing leadership skills.

In my mind, one of the best ways to learn about leadership is to read, absorb, and apply lessons from the greats. I wanted to distill some of the more counterintuitive principles I’ve picked up from reading books like The Score Takes Care of Itself, Extreme Ownership, and What Got You Here Won’t Get You There.

  1. Be a leader, not an achiever.
  2. Make yourself unnecessary.
  3. Take all the blame.

Here’s more about those leadership principles and how they specifically apply.

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How to Kickstart a Feedback Culture on Your Team

I distinctly remember a time when a feedback conversation blew up in my face.

I was managing a team of personal trainers at a recreation center on my college campus. During a shadowing session with a newer trainer, I sat down with them to go over some suggestions I had. In my gut, I knew this wasn’t going to go well.

Immediately, the trainer grew defensive. Instead of listening to what I had to say, we were arguing back and forth. Firmly entrenched in my own viewpoints, I argued back. The conversation didn’t get out of hand, but it was clear we weren’t making any progress. Both parties were set in their own thinking and showing no signs of budging.

Perhaps you’ve been in this exact situation—approaching a new teammate with some critical feedback. You want desperately for the conversation to go well. In many ways, that first feedback conversation sets the tone for the rest of the relationship. Recovery from a bad start is possible, but it’s uncomfortable and difficult for everyone involved.

Starting a cycle of feedback on your team is equal parts important and delicate. The trick is to not start with direct, critical feedback but rather progress that direction over time building a relationship along the way. Here’s a step-by-step progression for moving from 0 to “This could be better” without burning bridges.

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Moving Up the Care Personally Axis (Radical Candor)

I just finished up with Radical Candor, a book on leadership by former Google and Facebook executive Kim Scott. Scott lays out two axes that exist within leadership—care personally and challenge directly. Together, they create the radical candor framework.

A visual depiction of the radical candor framework
This post on First Round Review offers a great breakdown if you just want to learn more about the framework. Image from Radical Candor.

Care personally is just that—demonstrating to your teammates that you give a damn about their well-being and success.

Challenge directly is all about helping them improve, giving them feedback, and pushing them to excel.

I want to talk about moving up on the Care personally axis and moving towards Radical Candor pulling both from the book and personal experience.

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The Unpracticed Art of Receiving Feedback

Receiving feedback, particularly critical feedback, can be challenging.

When I first stepped into the role of team lead at Automattic, I knew one of my biggest areas for growth revolved around feedback. Sure, I’d led a team in the past, but this felt like an entirely new ballgame.

I dove in headfirst into reading all about feedback. I scheduled feedback sessions with everyone on my team and encouraged them to give me feedback as well with leadback surveys. Overall, I thought I had a handle on the feedback thing.

About a year ago, I stumbled across the book Thanks for the Feedback by Douglas Stone and Sheila Heen. Not only did the book have an amazing tagline1; when I put it down, I realized I had earmarked nearly every other page. It changed how I viewed feedback in general.

Giving feedback was only half of the equation; receiving feedback was the other (arguably, more important) half. I realized that focusing on the latter could help with the former.

In January of 2017, I gave a workshop to my colleagues at Automattic all about receiving feedback covering many of the concepts from the book and examples of how I was putting them to use. A few people told me the workshop was helpful so I thought I’d share it here.

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