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Isaac Mosquera: On Managing Technical Teams and Two Books Every Engineer Should Read

Posted by Jenny Medeiros on Oct 23, 2019 12:46:00 PM
Jenny Medeiros
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Isaac Mosquera on a starry background next to Frontier Podcast logo

Sometimes you don't feel like listening to a podcast, but you still want to know the most important points. We get it, so we're taking fascinating podcast episodes on engineering and turning them into easy-to-read stories.

Today, we're covering an episode from the Frontier Podcast produced by gun.io—the freelancing platform where "engineers go to hire other engineers." On episode 157, Isaac Mosquera (CTO at Armory) was invited to share why he moved from coding to managing, how he ensures his own team runs smoothly, what advice he has for others in technical management, and the two books he recommends to every engineer at Armory.


Here are the main takeaways from that episode.


Moving to management

Isaac knew early on that he wanted to be an engineer. His father was one, so it seemed like the most natural choice. But after working in various engineering roles, he realized there was something about sitting down and coding to solve problem after problem that just wasn't fulfilling to him anymore. Management wasn't even a passing thought at this point—until a team of ten people was dropped into his care.


Being the proactive guy that he is, Isaac jumped into his new responsibility headfirst. He began by asking them to rate their happiness level from one to four, and was surprised to learn they were all deeply unhappy. "I started working to try and understand why they were unhappy," Isaac said on the podcast. "And ultimately, over a period of time, I got all their happiness ratings to threes and fours—I didn't lose a single person on that team. It was genuinely satisfying and fulfilling."


So while Isaac loves coding and will always mark himself down as an engineer (even on his dentist check-in form), today he defines himself as someone focused on empowering others to accomplish their goals. Although, he does admit that it's "much harder dealing with people than it is dealing with technology."


How he manages his own team

Armory is known for its high-performing, world-class engineering teams. So, when asked how Isaac manages to keep his engineers engaged, productive, and working on the right things—here's what he had to say:

On keeping engineers engaged in the business problem

At Armory, engineers are flown to help onboard clients onto Armory's Software Delivery Platform for streamlined business and development workflows. For Isaac, these interactions are essential to keep engineers in touch with their user's perspective and pain points when using the products they're building.


"When you separate people too far from the user, they lose touch with the business problem," Isaac explains. "Giving them context enables them to have a greater sense of autonomy and ownership over their product."


He adds that this practice also makes his own job easier, since he doesn't need to tell everyone what to do. This in itself is a game-changer for most engineers, who typically come from companies where they're simply "the coders" who never interact directly with the end user.


"They're growing themselves in the sense that they're doing things a company has never asked them to do before," he says. "They're learning a whole new set of skills on how to communicate, how to gather feedback, and how to organize their peers to solve a problem. I think that's super important, especially in this day and age."

On avoiding conflict

Having a self-organizing team can get messy without proper communication and some form of guidelines. Isaac shares that his team operates under a governing philosophy called the "roundabout culture."


In short: most companies follow a "stoplight culture," where a product manager tells an engineer what to build and when—similar to how a stoplight tells cars when to go and when to stop. At Armory, they're moving towards a "roundabout culture," where each team member individually decides what they need to do. Just like in a real roundabout, everyone is responsible for their own behavior.


To make this new culture work, Isaac's only requirement is that they be transparent and inform anyone who would be affected by their work.

On tackling the right features

Engineering teams at Armory need to find a healthy balance between building proprietary features that generate revenue, and building open source features that keep the OS community alive. Plus, they need to manage their technical debt. That's a lot to juggle.


Isaac's answer to ensuring his team focuses on the right tasks is: metrics, metrics, and more metrics. 


"We set targets and milestones for how we're going to divide up the underlying resources and focus on proprietary versus open source." He adds that every time they create a JIRA ticket, they label it (as a feature, tech debt, etc.). Then, at the end of the quarter, they analyze whether they're investing their time in the right things.


Furthermore, if an engineer wants to spend time on clearing tech debt, they first need to present the metrics to justify why doing so is a priority. "I know how painful it is to deal with tech debt, especially when it doesn't get prioritized," he says. "But I think it is important for engineers to explain what the business value is of any activity, not just tackling tech debt."


His advice for engineers and technical managers

How to avoid bad retrospectives

Continuing his point on empowering engineers to make their own metric-based decisions, Isaac emphasizes the importance of holding retrospectives to go over the decisions that went well (or not well at all).


He then dives into what he strongly believes technical leads shouldn't do in a retrospective:

  • Don't name names when someone messes up. It's important that people don't feel bad about themselves when things go wrong. Instead, focus on two or three action items to improve the system for next time.
  • Don't let the quietest person get drowned out. Everyone should get their turn to tell you what went well, what went wrong, and what we can improve—without getting interrupted. Set a time limit for each person.

Isaac then gives an example of a past off-site retrospective where he opened it up to the entire team and allowed them to guide the conversation—rather than make all the shots himself. "Anybody can participate and anybody can change anything in this organization," he says. "We all win together and we all fail together."

What every technical lead should know

"Be more empathetic."


That's the key piece of advice Isaac has not only for technical managers, but to his younger self. He says that whether you're an engineering leader or senior engineer, empathy is what the industry lacks the most.


"I think so many times we're quick to judge the decisions others make and we get into these really these heated technical discussions that you can see on Twitter," he says. "It's just really unhelpful, it never moves the conversation forward."


Isaac ends his sage advice by encouraging engineers to figure out how to work better together and solve the business problem. "Ultimately, whatever the argument is about, it matters a lot less than actually coming together, finding a solution, and making us better as an industry and as people."

The two books every engineer should read

Finally, Isaac reveals his top book recommendations for new hires at Armory.


The first book is Accelerate by Nicole Forsgren, and Jez Humble. "It talks about how to empower an organization to move faster and measure productivity," Isaac says with enthusiasm. "It also gives a good framework, based on science and statistics for measuring those aspects CIOs and CTOs have so much trouble with."


His second book recommendation is The Lean Startup by Eric Ries, which most technologists have already read—or have at least heard about. "It's not just about code," Isaac says. "It's about running experiments and trying out things that are small in nature, but can impact the direction of the organization."


Listen to the podcast

You can listen to the full Frontier Podcast episode with Isaac for extra stories and details that didn't make it to the post. If you want to know more about Isaac Mosquera and his work at Armory, you can connect with him on Linkedin. You can also catch him at the upcoming Spinnaker Summit as he's set to give the opening keynote on behalf of Armory (which you can already add to your calendar).


Lastly, if you haven't signed up for Spinnaker Summit and don't want to miss two days of talks, hands-on workshops, and the chance to meet all your software heroes in one place, register now while seats are still open.



Topics: Inside VOICE podcast, Spinnaker, Interview