What a great technical leader looks like
I started programming when I was twelve, so I guess you could say I’m pretty technical. I still code sometimes because I enjoy it. As my career has progressed and I’ve been involved in lots of different startups, I get asked from folks in the community pretty regularly how to evaluate technology leaders.
The technology leaders in a software company, especially a startup, will make or break the business. They are the bridge from the technical side of the house to the business side, and they have to be proficient at both. And it’s really hard for non-technical folks to evaluate technical leaders because, obviously, there’s a lot they don’t know.
I was asked about this again and it prompted me to sit down and write a list of what I look for in a tech leader.
1. Great technical leaders have excellent soft skills.
They will be in lots of meetings, dealing with lots of fires, and need to be able to calmly deal with all sorts of problems in ways that lead to resolution, not inflammation. This isn’t a skill that most technical people learn naturally. But as anyone who’s done this knows, getting people running in the right direction and change management is just as hard, or harder, then the technical problems.
2. Great technical leaders hire and inspire great people
They need to recruit, develop, and retain talent in competitive markets, and make sure their teams are motivated and aligned. There should never be any surprises when it comes to personnel and culture, and they need to insulate the teams from their internal struggles.
3. Great technical leaders have technical mastery
The best technology leaders are the ones who have the ability to understand what’s happening at any level, and deep down they still love technology. They still code and try new things — not necessarily because they plan on contributing to the main code base but because they love it (I wouldn’t touch our production code with a ten-foot pole!). And It’s important that their skills are current and they can jump into a conversation, at any level, and quickly get up to speed and what’s going on and why. Great tech leaders care about things like architecture diagrams and data schemas and how they’re being curated and maintained.
4. Great technical leaders get in the weeds as much as they need to
While it’s tempting to delegate everything when people become managers, sometimes you still need to roll up your sleeves and get your hands dirty. It’s great to trust the people you hire, but trust and verify. Great technical leaders don’t deal in platitudes and buzz words, they talk about specific problems and strategies. The warning sign here is that if someone doesn’t seem to have a good understanding of a problem, they’re probably not going deep enough. They might not even be capable of going deep enough as they should be.
5. Great technical leaders are creative
They come with solutions, not just problems. They invent. It’s really easy to criticize, but at the end of the day it’s no different than an excuse. Even if it’s not our problem, is the person looking accomplish the goal or deflect blame?
6. Great technical leaders don’t expect perfection at 1.0
They realize that the quickest and easiest way to get to your final destination is by quickly deploying, iterating, and then learning along the way. They’re not ashamed to admit mistakes because they are a natural result of imperfect information and moving fast. They realize that there are deadlines that need to be hit and sometimes that means shipping imperfect code. They expect some level of tech debt in order to hit timelines, and creates white space for developers to go and fix it afterwards
7. Great technical leaders don’t deal in binary outcomes
They understand that most things in the real world are not black and white, they are shades of grey. For example, if your goal is to create something productized and reusable, the two options are not either completely hard-coded or completely configurable. These two options are at two opposite ends of a spectrum. One of the things I still struggle with is communicating this gradient to development teams in a way that gives them freedom to go fast while at the same time making choices that don’t constrain future extensibility. It is most definitely a communication skill.
I’ve had the privilege of working with several great tech leaders and I’m also privileged to be working alongside several of them right now. They’re hard to find and are worth their weight in gold, which is probably why it feels a lot like sifting for gold when you try to find them. Hopefully this list helps folks out there looking for technical leaders, good luck!
