Leadership is simple and simple is hard


It’s been a while since the last time I wrote a summary of what I had learned about leadership. This post is about some of the general concepts I’ve picked up along the way — partially so I have them written down, mostly so I can share them.

Mind you — there’s no panacea to be found, just guidelines. I wouldn’t have it any other way. I just try to absorb as much as I can.

Management philosophy: lolwut?

A common question I get from folks: “What is your management philosophy?”

My first response to this question is to ask if you think management and leadership are related, mutually exclusive or complimentary. If I had to boil it down, leadership is your ability to motivate people. Management is how well you execute. I’ve also heard that management is doing things right while leadership is doing the right things.

However you define these, I don’t see how you do one without the other. Lean too far in one direction, you’re a babbling prophet with great intentions. Lean too far the other way, you’re a lonely, walking and talking autobot. Both are undesirable fates not meant for humans.

Let’s just say I strive for competency in both and always will.

A useful list of stolen wisdom

I still need to answer the question, which leads to a discussion about non-hierarchical empowerment. I don’t think leadership or management philosophies have a 1-minute elevator pitch, though.

To answer in long form, I constantly draw on a series of idioms, quotes and principles I’ve accumulated over time. Some of them I have borrowed permanently from other leaders, and I’ll link to sources. Others are just things I say all the time. Let’s run through these:

  1. Start with the why, ask questions about how and the what takes care of itself
  2. Hire great people and get out of their way
  3. An engineering team isn’t an assembly line — and shouldn’t be run like one
  4. Success is the quality of one’s effort
  5. The only time I’ll get mad at you is when you don’t try
  6. Look for humility and faith — without those, you have nothing to work with
  7. Know where people want to go and help them get there
  8. Push power to the edges, and find a way to have decisions happen where information is
  9. Work is like improv
  10. No assholes!
  11. Does this have to be said by me? Does it have to be said now? Does it have to be said at all? (Mike Shaver/Mike Beltzner/Canada)
  12. Listen like you’re wrong, fight like you’re right (John Lilly)
  13. Don’t whine, don’t complain, don’t make excuses (John Wooden)

No, you won’t find this stuff in textbooks

Being asked about management and leadership so many times last summer made me realize my answers seem obvious. Five minutes into spewing statements like the above and it sounds “textbook”. I actually got this feedback once after an interview. To that, I ask: what textbook? I’d like to read it.

The truth is you won’t find the answers in just one book. They are all over the place. Many of these concepts are relatively simple or common sense, but most books, blogs or articles work hard at uncovering an undeniable truth:

Simple is really, really hard.

iPhones, web search, airplanes, TCP, cars, 4GLTE — if you look around we are surrounded by amazing, complex things we take for granted. Do you realize how amazing it is that we can fit 40,000 vinyl records into our pocket for less than the cost of a television? Is it easy to give people access to data anywhere they are? Hell no. Simple concepts, impossible delivery.

Management and leadership both have many simple concepts that are difficult to handle. They can be harder than deterministic systems because people are difficult. John Taffer (from Bar Rescue – love this show) always says, “I can fix bars, but I can’t fix people.”


If all else fails, watch this:

And this:

Inspiring people sounds easy but it’s damn near impossible to do unless you believe in what you’re saying. The hardest part of being a leader is putting yourself out there — to be humble, vulnerable but confident all at once. While you do that, you have to constantly fight your urge to take over, take full control. Because leadership is not about power or control, it’s about creating an environment. That is what makes you a vehicle for your mission or idea. That is what makes you a force people are inspired by. Simple, right? Right.

Simple, but really, really hard.