Decoding Leadership

Katie Wilde is an accomplished leader from Snyk, Ambassador Labs, and Buffer. She shares how she learned to be an effective director (and how challenging the transition was), and shares tons of insights into why it's hard to build a culture of reliability in engineering organizations. And she shares a bunch of wonderful approaches to make reliability fun and desirable. This episode was a delight, and I learned a bunch from it.

We often don't prioritize the tiny things that make exceptional products. I share a practice we adopted recently that helps us ship lots of little things every Thursday.

Ben is an experienced talent acquisition leader. We discussed how leaders can work effectively with recruiting, how he coaches recruiters to work better with their stakeholders, how to stand out in the current job market, and what he's learned about leadership himself. He also gives the controversial advice to not jump to hiring a recruiter!

I loved this conversation with Alex Kroman, Chief Product and Technology Officer at LivePerson. We dive into the topic of how to craft great leadership teams, balancing vision with execution, overcoming the hub-and-spoke management model, leveraging diverse skill sets, and improving decision-making quality. Alex is someone I've learned a great deal from, and I invite you to do the same in this podcast!

What can we learn from Paul Graham's "founder mode"? Mostly that it describes a poor way of thinking about delegation. It's not just for founders, and it can be dangerous for founders. But it's a useful tool to have in every leader's toolkit.

I interviewed the founders of Reclaim.ai, a successful startup that was recently acquired by Dropbox. Learn the unusual approaches they took to build a radically customer focused company. We cover how they gave up planning, selected leaders with unusual backgrounds, and kept their technology simple. And they share some of the decisions they made that helped them iterate on their approach and build a product I use every day.

We delve into the concept of "piles", and why it can be a useful tool for seeing how to optimize flow.

We cover a simple process change that is the most impactful way I've seen to prioritize reliability work. It's a rule called the "Don't Repeat Incidents" rule. In this short episode, we cover how we developed this rule, and why it made such a difference.

We discuss the inevitable challenge of being the bottleneck and how to get yourself out of this situation, mostly by growing and training your team. Learn approaches such as

1. Setting up indicators to preserve focus,
2. Using the concept of a leadership ladder to uplevel and evaluate your team, and
3. Using completed staff work to provide a standard for management work.

I also share

1. Practical advice for delegation,
2. How to use tenants to shape your organizations thinking, and
3. How to use the "gospel of I intend to" to improve coordination and allow your team to own more.

These are all important techniques for creating teams that can operate more autonomously!

One of the most important concepts in developing a strong organization is "organizational work". I describe the concept, how you can use it to drive lasting improvements in your organization, and how you can use it to build strong, collaborative leadership teams.

Let's talk about macho and bro-ish leadership culture! Macho cultures often exhibit aggressive and sometimes sexist behavior. While risk-taking and aggressive behavior isn't uniformly bad, macho culture can result in groupthink and result in poor decision-making. And it can drive away talent. We explore why these cultures emerge, often due to stereotyped views of leadership, and share techniques for navigating them. 

We discuss two related topics: fan out work and managing bottleneck teams. We first delve into fan out work, its causes, examples, and some of the problems it causes. We discuss a couple of approaches to reduce the impact of fan out work, such as having teams complete their own fan out work, and setting limits on such projects. 

We then discuss bottleneck teams. Every organization has teams that suffer as they support the most critical aspects of the business. We discuss common issues like stakeholder bullying. And we offer some solutions such as adopting self-service models, adding rotation roles, and redefining the responsibilities of the team. 

The format for this episode is an experiment -- I'm not interviewing anyone else!

John Hyland is an expert on making early career engineers successful. They led up the Ignite program at New Relic, which was an incredibly innovative program that was so good they expanded it to more senior levels. They go into some detail about how they set up and adapted the program. They also give lots of advice on hiring for both early career and later career engineers. 

After that, we did a retrospective on deconstructing a Ruby monolith at New Relic. It was a large, complicated project, and some parts of it didn't go as well as we expected. We dug into what we could learn from that that applies to all large, complex software projects. 

Finally, John brings up the Preventable Problems Paradox, and we discuss how to incentivize better behavior at companies besides just firefighting.

In this episode of Decoding Leadership, Jade sits down with experienced engineering leader Jason Poole to discuss the ins and outs of building strong partnerships between product, engineering, and design. Jason shares his insights on:

• Establishing trust and a unified front in engineering/product relationships
• Integrating design into the triad and its transformative impact
• Communicating effectively within the triad through structured and ad-hoc touchpoints
• Helping local teams develop their own effective triads
• Lessons learned from experimenting with the single threaded owner model vs. triad approach
• The distinction between management and leadership skills
• A powerful framework for efficient, high-quality decision making as a leader

Nadya is an accomplished product leader and chief product officer. I've always been impressed with how she has navigated getting large groups of people on the same page. And she's really good at aligning executives. She gives us some tips for getting better at that, and talks through her approach to radical candor, protecting teams, and growing the people on her team.

Keizan Shaffer talks through how he thinks about mentorship. He talks about the importance of surfacing your thinking and sharing your mental models, how mentorship, teaching, coaching, and sponsorship are different. And he shares some career advice that his mentors have found useful. He also talks about Conway's law, and some tips for managing reorgs successfully.

Alexa Stefanko led one of the most dramatic improvements in a team I've seen. We talk about a set of changes we introduced at Gremlin, including the Single Threaded Owner model, the introduction of product metrics, and setting up an "API" between local teams and senior leadership. Alexa also talks about her move to being a director, the differences between medical and tech leadership, and how animal training has influenced (and not influenced) her approach with people.