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Our 5 favorite episodes from StartupCTO


Our 5 favorite episodes from StartupCTO

Podcast for engineering leaders

Think back to when you were first asked to step up as a manager. Maybe you’re the exception, but at this transition, most engineering managers realize that they have little understanding around how to actually lead a team.

Kevin Owocki (@owocki) and Miles Matthias (@miles_matthias) felt this way too, and decided to do something about it. Over the past few years they’ve interviewed engineering leaders on a variety of relevant topics and made these conversations available to the world via StartupCTO.

This podcast is perfect for engineering managers who enjoy hearing others’ perspectives on leading technical teams. Before you dive in, we’ve collected a list of our favorite episodes with some of the best moments from each.

Without further ado, here are our 5 favorite episodes from StartupCTO (in no particular order):

Scaling the Rocket Ship


While being the CTO of DigitalOcean, Julia Austin (@austinfish) is also a senior lecturer at Harvard Business School of Entrepreneurial Management, and an advisor and board member of multiple startups in the Boston area. In this episode, she shares lessons learned from scaling at the speed of a rocket ship. Our favorite moments:

  • “We keep adding all these people, why can’t we get more done?” When your hire more people, there’s more organization, more prioritization, and more communication required. Consider evaluating whether your processes are scalable before you scale your team.
  • “It’s important to have some structure in place—not because we want to have a hierarchy, but to have the ability to empower and enable teams.” Ultimately, having some form of a hierarchy will help give teams autonomy, and reduce the amount of bureaucracy that slows them down.
  • Don’t waste time taking on something that you’re not good at. Someone within your reach is good at it — find them. If it’s vital to your company — say, finance — and that person is not already in your org, hire them. It will save you (and maybe even your company) in the long run.
  • DigitalOcean retains engineers by encouraging their individual development. One way they do this is by offering “learning streams” that employees can sign up for, and call it the “DigitalOcean University”.

“Don’t put process in for the sake of process. Process should be elegant and light.”

Apart from scaling teams, Austin touches on topics like getting an MBA, early stage startups, and how DigitalOcean perceives their customers. Listen to her interview here→

Understanding People is a Superpower


You might have heard of Michael Lopp (better known as @rands) from Managing Humans, or Being Geek. In addition to actively writing about leadership, tech, and writing itself, Lopp is the VP of Engineering at Slack, and has previously lead teams at companies like Pinterest and Apple.

In this episode, Lopp articulates lessons he wishes he’d learned earlier, principles of effective management, leadership styles, and how writing and coding are similar.

Here’s what we learned about being an effective engineering manager:

  • As a manager, your job is to “make the machine run well” by only focusing on people, processes, and the product. Listen, observe, and be realistic about what your strengths and weaknesses are. Stop doing the things that you’re bad at, and focus on creating differentiated value. So if you’re bad at something, find the person that’s good at it…
  • And delegate. Engineering managers are generally bad at delegation — our industry teaches engineers to devalue delegation, and are not rewarded for people-oriented skills. But it’s a vital to your growth as a leader. When Michael delegates work, it sounds like this: “here’s what winning looks like, here’s how we’re going to watch you win, and….Go.”
  • 1-1s: 30 minutes, every week (and don’t change them). Earlier in the week is better. Michael strongly recommends doing them: they build trust, and are a signaling mechanism. You can learn things like how your team is communicating, and how data is getting to you. They’ll help you stay connected with what’s going on in your team.

“I want the product to grow, but if I don’t have happy, talented, and productive engineers, I’m screwed. My main job is to figure out how can I get this group to thrive.

Listen to Understanding People is a Superpower→

Creative Engineers are the Leaders of the Software World


Jud Valeski (@jvaleski) has been part of technical teams at IBM, Netscape, Onebox, AOL, and most recently was the co-founder of Gnip (acquired by Twitter). In this interview, Valeski illustrates the value of creative developers, the importance of creativity in the development process, and shares how to make room for this type of exploration in your team.

Here’s what we learned about building a world-class culture:

  • “Never lose site of the value of these individuals”. Technical teams are often the most expensive thing in the room. “You have to be very careful about who you assemble and rally to be on that team.” And a lot of care typically goes into assembling that team. The challenge is then how to effectively deploy that resource.
  • Find the right degree of definition around what the company wants to build: so “your team can apply their technical capability as well as their creativity to solving the problem.” If you’re overbearing with definition, you’ll squelch your team’s full potential. Yet if the definition is unclear, you risk losing site of the bigger picture (or having your team all work in the same direction).
  • Want to build trust in your team? It all boils down to your ability to empathize. “Unless leadership has written software, gotten it into production, and gotten it consumed by users, I think you can wind up with some pretty nasty operating environments and companies.”

“It’s about building a crew – a creative and technical and scientific crew – and blending all that together to build interesting, highly scalable software.”

Listen to the full conversation here→

Bend the Learning Curve by Consistently Putting Yourself into a Place You’re Uncomfortable


In addition to having founded her own technology consulting business, Kathy Keating (@kathkeating) has helped build several successful technology startups, and is an active member (and mentor) in the Denver tech community.

In her interview on StartupCTO, Keating talks about some of the most important things she’s learned from her experiences consulting with and mentoring the leaders of tomorrow.

Here’s what we learned:

  • It’s important to surround yourself with people who are experienced with making great decisions. This could mean simply following them on Twitter or Medium, but consider also attending conferences when you can. Actively listen to leaders, and you’ll subconsciously become a better manager — whether it’s by making better technology decisions, or by getting a fresh take on how to communicate with your team. It’s all about strengthening your intuition.
  • Another opportunity to be active in your community is to be a mentor — it’s a great place to practice your leadership skills. Plus, it’s a great way to build a network, which will improve your hiring pipeline. Kathy has hired many of her former mentees. That being said, you have to be realistic about what you can take on. Engaging with the community doesn’t have to be a weekly practice — it can be quarterly, or yearly even.
  • It’s not easy, but continue to practice building your capability to say “yes” when you need to say yes, and say “no” when you need to say no. It’s vital to your effectiveness as a manager.
  • The quickest way to “bend the learning curve” towards becoming a professional is to put yourself in a place that you’re uncomfortable. Being comfortable with being uncomfortable is a learned skill — if we can understand this about ourselves, we can better understand what type of role or type of company we should be in. And because putting yourself in a place that you’re uncomfortable accelerates learning for individuals, it’s your job as a manager to ask how you can put your team in a place that’s both uncomfortable and supported so that they can continue to learn and grow.

“How can I put my team in a place where they’re comfortable being uncomfortable, so they can move forward and grow?”

Listen to Kathy’s interview here→

Optimize Your Learning Velocity


Scott Carlton (@scotterC) is currently the VP of Technology at Andela, a global engineering organization dedicated to fostering the next generation of elite tech talent across Africa. With an entirely distributed team, building culture is a particularly interesting challenge.

In this episode, Carlton breaks it down to a science.

Here are a few of our favorite moments:

  • “I think a lot about communication through a company in the context of dynamic systems and controls. You can have an input of information where someone’s unaligned or there’s some dissonance, and you’re not going to feel the full tail-whip of that until it works it’s way through the organization.”
  • “I’ve found that in hiring, I should look for ‘potential’ — not ‘pedigree’”. Scott had a number of experiences with bad hires, or bad fits, before he hired what would become some of the best engineers he’d ever had. They were passionate, ambitious, and took feedback really well.
  • “I didn’t want to do 1:1s at first. You’re always going to find out things you didn’t know. But that’s one thing I’ve learned in startups—if there’s something you don’t know, you want to race towards that as fast as possible.” And as for 1:1s in general, they’re all about getting everyone aligned. “If we’re not all aligned, we’re not going to be able to push in the right direction.”
  • “I’ve joined two companies where I came in late—I started after the engineering team had already formed.” If you find yourself in this situation, “at first, 1:1s are about clearing out a backlog, and putting problems into the light. Then, you can focus on the problems of the ‘now’— the painful things, or the hard requirements. Then, after time, you can focus on the future. And that’s when engineers really start to gel as a team—when they all have the combined, unified future to work towards.”

“As a leader, it’s not about hiding issues. It’s about actively seeking them out, and becoming a lightning rod for issues.”

Scott had plenty more to say that demonstrated his passion for developing peoples’ potential. Listen to the full interview here→

Quantifying Engineering Productivity


Here’s a bonus one, and of course, we’re biased. In this conversation, GitPrime’s CEO, Travis Kimmel, recalls the challenges he ran into as an engineering manager and shares his vision to revolutionize how software teams work. Listen to the full conversation here→