A Leadership Toolkit

Leading people takes a lot of energy. Once you move from being an individual contributor to a manager, everything feels and functions differently. To combat this, I created a leadership toolkit for myself.

It reads like a letter to myself, a reminder that when things get chaotic and I’m overwhelmed, I always have choices. I’ve amassed expertise I can draw on. Even making mistakes will help me hone my craft. I aim to keep it updated as my career evolves and I grow in different ways. I bet I’ll read it more often than revise it, as that’s its biggest purpose.

I’m sharing not because I think this exact set of principles will help anyone. More that maybe in reading this, you’ll be inspired to explore and build your own toolkit. If you’re on the right path to creating a system that works for you, you’ll see it’s not about becoming or being a leader, but instead, reminding yourself of who you are already.

Special thanks to Akshay Kapur, whose coaching and collaboration helped me craft this over the last year-plus working together. If you’re looking for a leadership coach, please reach out to him.

Leadership statement

I bring empathy and persistence to my work as a leader, focusing on seeing clearly and helping others do the same.

I aim to foster perspective, movement, empowerment and transparency with the people I work with every day. I see my job as selling ideas. I plant the seeds of the ideas so that individuals and teams can come up with better ideas. To carry the metaphor further:

“Be a forester. Plant the trees; remove what can’t flourish. You tend to the forest because you know that diversity and strong bonds between elements creates the strongest ecosystem.”

Mindsets

I use a few mindsets in my work:

Journalist: I’m a storyteller through and through. Ever curious, always asking questions. Think of the popular journalism axiom: “comfort the afflicted and afflict the comforted.” Writing helps me often get to better clarity.

Runner: I know races aren’t won the same way every time. I constantly look to apply the right training and approach to what’s ahead. I’m not afraid of a tough run or a run on a new trail. That helps me grow stronger.

Co-Leader: I lead, but with people and through people. I’m excited when people engage with me on a challenge. Where some may see opinions and noise, I see opportunity for alignment and clarity.

Maker: I create for a living and out of necessity. I have to because it’s how I’m built. Making gives me the most energy.

Methods

These methods serve as reminders to how I like to work:

Imperfect: My craft requires creativity, and there’s no “right” way to find it. But you won’t find it if you’re trying too hard.

Gentle nudges: I prefer to nudge people toward a path. But I know when I need to apply more force too.

Put it down: When I get stressed because something takes hold, I remember I have a choice. I can put it down.

Practice silence: My job requires a lot of inputs. Silence can be one that helps me know which inputs matter most at any given moment. It helps me make my own inputs too.

Think in buckets: Who needs to help me right now? Journalist, Co-Leader, Runner or Maker? What needs attention? People, Process, Projects or Me?

What’s the story? What’s the narrative here? I’m always searching for the story because if I know the story, I’m closer to clarity.

Tools

I can practice these skills when I’m unclear:

Do nothing time: Take 30 minutes to do nothing. Let your mind wander without an agenda.
I wonder: Ask yourself, “I wonder if…”, “I wonder why…”, “I wonder how…”

Write it out (journal): The faster you do it, the more valuable it usually becomes later.

Draw it out (whiteboard): You are a designer after all.

Talk it out (inner circle): Play the journalist and co-leader.

Know/Don’t Know exercises: This is the research that will always drive the story.

Leadership as a craft

Approach your work as though it’s a trade. Here’s a process to practice that:

  • Listening: Ask at least two questions that make others pause & think
  • Balance: Block your calendar between 6pm-6:30pm daily
  • Writing: Type for 5-10 minutes without an agenda

Emergency!!!

Feeling overwhelmed?

  • Find time to workout. Kettlebells to the rescue.
  • Schedule “do nothing” time. Aim for at least three times a week.
  • Write. Just put words on a page somewhere.

Published by David A. Kennedy

I work as a Design Director at Automattic on Jetpack, focusing on the front end experience.