Managing Up

Everyone Has Had A Terrible Boss I’ve had them, and I’ve been one… but, bosses are only terrible if you allow them  to be. Here’s my framework for managing my manager, improving my personal happiness, and becoming a better delegate. Management 101: Define Projects Using Five Variables Time $ Quality/Scope Expertise (who performs the work) Risk […]

How To Portray Confidence As An Engineer

Murphy’s Law, “Whatever Can Go Wrong, Will Go Wrong” Best Exemplifies The Mindset Of A Great Engineer An engineer’s outlook is inherently pessimistic, although some may simply call it “practical.” This is appropriate when building stuff, but when speaking with CEOs or board members, that sort of approach doesn’t fly. “I figured out a simple, […]

How to Manage Your Company’s Technical Debt

Debt, At Its Most Basic Definition, Is When You Trade Getting Something Now For The Cost Of Interest Even if you pay back your debt quickly, you’ll still end up paying more than you originally took. If you don’t, then your debt will increase. If you choose to ignore your debt altogether, you’ll eventually go […]

How to Hold a Rally Meeting

The Rally Meeting Is An Unavoidable Event “Bad shit is coming. It always is in a startup. The odds of getting from launch to liquidity without some kind of disaster happening are one in a thousand. So don’t get demoralized.” – Paul Graham The truth is, success in the industry is hard won, and even […]

How To Be A Great CTO – 8 Things All Great CTOs Do

Being a CTO… Means working with people to create technology, not, coding. A good CTO is a CTO 100% of the time. Doing any other jobs for a company kneecaps your ability to do your job. Many people assume a great CTO is the best technologist in the room. Instead, this responsibility falls to the […]

Focus On One Thing When Working With People

It’s All About Focus I was thinking the other night about something a long time mentor shared with me a while back. On a long hike, he stressed the importance of improving only one skill at a time when working with people. I was surprised by his advice, having expected a larger lesson about dedication […]

Failing to Create Upward Mobility For Your Staff Will Destroy Your Team

Create An Exit Strategy For Everyone Ask every member of your staff “Where Are You Headed And How Fast?” and then work to help them accomplish their goals. Hold the conversation early and often. If you don’t, your team will implode. You’d Think A $2 Billion Startup With 500 People Would Have Basic Leadership Principles Down… I […]

CTO vs Chief Architect – Career Paths For Engineers

Not All Engineers Will Become CTOs Many engineers think that they will become a CTO one day, but statistically this isn’t even remotely accurate. Most engineers are surprised when they learn what a Chief Architect does, because it’s usually a much more attractive job for introverts. Ask yourself if you want to be talking to people […]

5 Tips For Balancing Quality vs. Speed When Developing Software

How I Meet Deadlines While Maintaining Code Quality Cutting corners to ship code as fast as possible is a necessary evil. But, there is a reason they call it “Tech Debt”. Deadlines means revenue, and more revenue means more money for everyone. Unfortunately, when left unchecked, the cost of the shortcuts we take stacks up […]