What to Look for in a Great Engineering Leader

Engineering leaders are tricky hires.? Do you want someone with great technical skills?? Great management skills?? Great charisma with customers?? A track record of performance at large and small scale?? Or do you look for your classic leadership principles…. ownership, tenacity, bias for action, customer obsession, hiring and developing the best, curiosity, growth mindset???

Well, yes, all of the above.? But practically speaking what actually matters day to day???

An engineering leader is running an organization that builds things… typically software, or increasingly ML models, but also teams, processes and structure.? At the end of the day, what you want is someone who is great at building.??

the most important trait of an engineering leader is that they must be biased to say “yes”, but willing to say “no”

There are different approaches to building.? Twenty-plus years ago, software was traditionally built in a waterfall fashion… requirements, specs, design, code, test, deploy… repeat.? As an industry, we increasingly moved to a more and more iterative model with shorter and shorter iteration cycles, to the point now that with continuous deployment, many organizations release software updates continuously.???

Depending on what your organization needs, you may want a different type of engineering leader.? If your customers prefer a slower, more methodical release process, you’ll want to bias to an engineering leader who brings that structure and a more consistent drum-beat.? If your business is more dependent on being incredibly nimble and scrappy, you’ll want an engineering leader who makes very high judgment decisions on where to be scrappy and where to invest in the foundation and can build a team that is motivated to build scrappy and is comfortable coming back to clean up later.??

a “yes-man” is the worst possible kind of engineering leader.?

But in my opinion, the most important trait of an engineering leader is that they must be biased to say “yes”, but willing to say “no” and right, a lot, when they say yes or no.?

The world is becoming more dynamic every day.? You’re going to ask your engineering leader to adapt and pivot.? Hopefully you’re pivoting and adapting for well-understood extrinsic reasons rather than just internal churn and lack of direction, but either way, you’re going to want the ability to go aggressively after a new opportunity or pivot away from something that isn’t working.? Your engineering leader’s job is to lead the engineering organization in those transitions.? If you have an engineering leader who is biased to always saying no, you will find yourself increasingly frustrated with him or her.? A great engineering leader is a business partner who understands what the business is trying to achieve and is biased to saying yes.??

At the same time, a “yes-man” is the worst possible kind of engineering leader.? Engineering leaders are also accountable for delivery.? When they say they’ll do something, you’d like to be able to depend on that so you can make commitments to customers, investors, internal constituencies who are depending on what the engineering team is building.? As a result, as much as you want an engineering leader who is biased to say yes, you also must have an engineering leader who is willing to say no when they know they can’t deliver.

“No” is important.? As a leader dependent upon engineering delivering, a clear no allows you to have a detailed discussion about the constraints.? A clear no protects your reputation with your customers, investors and internal stake-holders.? An engineering leader who is biased to say yes, but willing to say no, is a leader who has your back.??

A yes-biased engineering leader will burn-out pretty quickly in a space where they have to say no a lot, particularly if you make saying no extremely painful.

When you find a great engineering leader who is biased to say yes, but willing to say no, you now have a business partner who can ride the dynamic bumps of your business with you.??

Once you’ve found and hired that great engineering leader, your job has only just begun.? The challenge in managing an engineering leader who is biased to say yes is that she or he doesn’t like saying no.? Saying yes and delivering is 1,000x more rewarding to a builder than saying no.? A yes-biased engineering leader will burn-out pretty quickly in a space where they have to say no a lot, particularly if you make saying no extremely painful.??

Your job as a leader is to partner closely to make it possible for them to say yes most of the time while listening attentively and partnering even more closely when they do say no.? Easier said than done, but when that partnership works, it’s magic.??