Getting Started in Technical Leadership

I’ve been given the immense privilege of leading projects and teams of various sizes over the years, and an equally immense amount of grace as I inevitably messed something up in each of them. It’s part of the natural progression of shifting from an individual contributor to a leader.

I’m very much still learning myself, but I get asked “how do I get started” enough that I decided to draft this post to share a bit of what has helped me grow over the years. In addition to lived experiences, there are a whole lot of resources I’ve devoured that helped me frame my thoughts, get clarity, and armed me with templates that helped me make sense of this weird, hectic, beautiful, nebulous, and deeply rewarding responsibility.

I’ve split this up into the major concepts that I rely on day to day, at the bottom of each I’ve linked to several resources that have helped me in some way. They explain these topics with the depth they deserve, all have left a lasting impression.

The Many Types of Leadership

There’s countless types of leadership out there, and it is all going to depend on your industry and the size and structure of your organization. But I find it easier to think in terms of what is most often in focus, and for that I break it down into leadership of people, of projects, and of operations.

People Leadership

Coming from a technical background, our analytical brains are celebrated and our skills honed specifically to break down tasks in ways that computers can interpret. We don’t tend to be as naturally adept at doing the same for people, it takes a different kind of mindset and a whole lot more effort in collaboration and understanding.

However, there truly is no greater joy than those opportunities to help someone achieve something that’s important to them.

Project Leadership

Not necessarily project management, think more like technical team leads, architects, and staff engineers. These are technical leaders that are stepping out – at least in part – of the day to day code to do other things that support the team.

These are the people that translate project goals into technical milestones, make high level architectural decisions, helps with defining and grooming epics, creating tickets, identifying risk, and otherwise supports the rest of the engineering team.

Operational Leadership

These are the Engineering Managers, Developer Relations, and Director level roles that are less in the day to day leadership of individuals and projects but are still technical in nature.

This one is admittedly a bit broad in scope, I apologize to folks in any of these roles who may feel I’m over-generalizing.

How do I choose?

While many (most?) roles are likely going to span two or even all three of these types of leadership, it’s likely that one of them is going to be of higher interest to you. My suggestion would be to lean into that one initially.

Leadership duties can be emotionally draining, especially as you’re just starting out. Focusing on the parts that are of greater interest to you will hopefully give you some extra energy to offset some of the drain as you work on building your resiliency.

Standout Skills

In my attempt to maintain some semblance of brevity with this post, I’m focusing on the top three skills that I’ve turned to most in my technical leadership journey. For each I’ll give a quick what and why, some of my must have notes, and then recommended books that fundamentally changed how I approach that skill.

Organization

The more leadership you take on, the less things are going to come to you organized and ready to go. More often than not you’re going to be the one that becomes that organizing filter for others. Embracing nebulous requests, context switching, and acting as a mentor to others all require some level of personal and professional organization.

Organization Must Haves

• Create a todo list that never leaves your side, offload as much as you can to it so you can focus on thinking instead of remembering
• Documentation is a superpower, take some time to set up a place you can quickly turn to for realtime notes and use it – especially during meetings
• Strive for context and clarity in everything
• Follow up when you say you’re going to

Recommended Reading

• Atomic Habits by James Clear
• High Output Management by Andrew S Grove
• How to Make Sense of Any Mess by Abby Covert
• Measure What Matters by John Doerr
• Sprint: How to Solve Big Problems and Test New Ideas in Just Five Days by Jake Knapp
• The Checklist Manifesto by Atul Gawande

Communication

Being a leader means a whole lot of communication, both in terms of clearly articulating what you’re trying to say as well as active listening when others are speaking. It takes a great deal of empathy and emotional intelligence to communicate effectively.

Communication Must Haves

• Assume best intentions from everyone, start with empathy
• Psychological safety is paramount to an effective and happy team
• Listen with the intent to understand, not to respond
• Learn how to recognize burnout and boredom in others, and how to recognize what drains and what recharges you too

Recommended Reading

• Soft Skills: Improving Your Emotional Intelligence
• Active listening by Drs. Carl R. Rogers and Richard E. Farson
• Burnout by Emily Nagoski and Amelia Nagoski
• Losing our Minds by Lucy Foulkes, PhD
• Nonviolent Communication by Marshall B. Rosenberg, PhD
• Practical Empathy by Indi Young
• Quiet: The Power of Introverts in a World That Can’t Stop Talking by Susan Cain

Interpersonal Relationships

Building and maintaining relationships will take significantly more time, but it’s worthwhile and necessary groundwork. Those relationships are crucial to knowing what and when to delegate, how to manage challenging situations, and when to shift from mentor to coach and from coach to sponsor.

Interpersonal Relationship Must Haves

• We are much more than the sum of our parts
• Take all the blame, share all the praise, lead by example
• Get comfortable with delegating and measuring productivity as a team rather than as an individual
• Have a support network to turn to when you need advice, need to brainstorm something particularly tricky, and to get honest feedback

Recommended Reading

• Dare to Lead by Brene Brown
• Engineering Management for the Rest Of Us by Sarah Drasner
• Radical Candor by Kim Scott
• Resilient Management by Lara Hogan
• The Manager’s Path by Camille Fournier
• The Staff Engineer’s Path by Tanya Reilly

Additional Resources

Here’s a few more resources that really helped me that I couldn’t neatly fit into one of the skill categories above.

• The Foundation of Technical Leadership by Brandon Gregory
• The Three Speeds of Collaboration by Erin ‘Folletto’ Casali
• ‘Give Away Your Legos’ and Other Commandments for Scaling Startups by Molly Graham
• Leadership: Practical Leadership Skills course by Chris Croft

What Would You Add?

As I had mentioned at the beginning of this post, I’m still learning and am very interested to hear your thoughts on the types of leadership, standout skills, and especially any additional resources you’d like to share. Let's get a conversation started about it!