The Leader’s Guide to Hacking

This week’s CBS Money Watch blog focused on three leadership hacks.  The purpose here is to give details: a full disclosure of my hacking background, how hacking fits into leadership, and then the steps to creating your own leadership hacks.


Like many young Gen-Xers living in the suburbs in the mid-80’s, I was bored—out of my freaking skull bored.  And so, when my electrical engineer father brought home one of the first Apple II computers—before floppy drives, and when the top of line had 16k of memory, I was thrilled.  Even though that’s 16k, as in the size of an average email, not 16 megabytes (a small thumb drive today), or 16 gigabytes (the size of my current email database).

My dad’s instructions to me were simple: figure it out.  As a side note, many people think that Apple’s contribution to the world is the iPhone, touch screen technology, iTunes, or Apple Stores.  For people in my generation, Apple Computer (as it was known then) saved us from boredom and turned us into hackers.  The real contribution of the company was catalyzing the hacker movement.

Hacking has a deserved bad wrap.  The most famous document ever written on hacking is the “The Conscience of a Hacker,”  back from the year I graduated from High School—1986.  It describes a young student bored, judged, made to go through an educational system that was neither engaging nor fun. Then the kid finds a computer, which doesn’t judge him, and that opens up a world of learning, in sharp contrast with the teacher who busts him for not showing his math work because he did it in his head.  The hacker also describes hackers being arrested.

This was my life in the 1980s, minus the arrest.  My savior was an AppleCAT modem, which was to hacking what Harry Potter was to the imagination of another generation.  After convincing my parents to spring for it, I began running scams of all kinds.  Breaking into a few computer mainframes, setting up conference calls which only the phone company could do at the time.

The best hack (and one that makes me cringe to this day) was that I’d have my modem call the High School’s single pay phone.  It would ring and ring—no voice mail in those days—until some early-to-rise worker would show up, answer it, and hear a dial tone, which my computer emitted.  The person would think the caller hung up and would return the phone to its base.  My computer, however, didn’t hang up, and continued emitting the dial tone.  All through breaks and recess of the school day, students would pick up the phone, insert their coins, but no amount of dialing would make the dial tone go away.  So they’d figure it was broken, hang up the phone, having lost their 10 or 25 cents.  After a few hours, I’d escape from a math class (being labeled “highly gifted” had few perks,  getting to leave classes was one).  I’d walk to the phone, dial in my code, which commanded my Apple II to hang up.   The phone sounded like a Vegas slot machine that just hit it big.  All the money deposited since my caper began in the morning came out.  The first time I did it, so much change came out that I got scared it would give me away.  If anyone reading this blog went to James Monroe High School in the 1980s, I probably owe you some loose change—and an apology.

I turned from the dark side of hacking early enough that I don’t have a criminal record—unlike several friends.  I got scared straight when I saw what one in my circle, Kevin Poulsen, was doing, including winning a Porsche from an LA radio station by jamming their phone lines, ensuring that he would be the 102nd caller—and the winner of the car.  It didn’t take a highly gifted high school student to know the law would catch up with him, and it did.  While I was an amateur, Kevin was a pro.  Where I had gall, Kevin had guts.

But the hacker’s impulse didn’t go away when my conscience (and fear of being caught) overtook my desire to mess with things.

Years ago, after I’d joined the establishment as a professor, I got one of the first iPods.  It was huge by today’s standards with only 5 gig of storage, and it didn’t work with a PC.  One solution would be to buy a Mac, but the hacker in me saw a challenge.  I connected it to my PC (no small challenge at the time), figured out how its cataloging system worked, downloaded some MP3 songs, and after a few days of tinkering, got Madonna to play on the iPod.  I called my now 88-year-old father and told him of my exploits.  Unlike my illegal hacking activities, which he never knew about, this one made him proud.  And I told him how to duplicate the process.  He did.

That’s what real hacking is about: messing with something, learning hacks from other people, trying them, and passing along what works and what doesn’t.  Today, the web contains all sorts of hacks.  Some let you get to the next level in a videogame.  Some jailbreak an iPhone.  Some show you how to get almost unlimited storage on a TiVo.  Hacking is value-neutral.  It can be used for bad, which was me in High School, or for good, which takes us to leadership hacking.

Hacking’s Place in Leadership

So, you might ask, what does any of this have to do with leadership?

Leadership has two components—best thought of two hemispheres of the same brain.  One is a set of principles that have to be understood, and internalized.  I keep highlighting Warren Bennis as the codifier of many of these principles.  Leaders are conceptualists, as Bennis says.

The other part of leadership is a set of steps that work in specific situations, also known as a set of hacks.  Each hack has three parts: a problem statement, a set of steps, and a success indicator—how you know if it’s worked.  Other hackers will take your work and try it in a slightly different situation, tweak the process, and produce a new hack.  Others will combine hacks.

Today’s CBS Money Watch blog highlighted three leadership hacks that follow this format.

To be clear, the principles and the hacks need to connect.  Leaders are more than people with a set of steps that they try at random.  Leaders analyze everything, looking for the part of the system most open to change.  Then they implement a hack, and learn from the experience.

Designing Your Own Leadership Hacks

Here are the steps to developing your own leadership hacks:

  1. Start by focusing on the greater good, and realize that the greater good is often not what individuals want.  Many people want “Hollywood values”—glamor, fame, money, sex appeal, power, influence, and adoration.  What people need is a connection to a higher purpose, and organizations that serve people, and invent the future.
  2. Go deep with the principles of leadership, until they resonate in your bone marrow.
  3. Find an area of your organization that demonstrates a lack of leadership.  Usually, these show burnout, the after-effects of bad management (people who have been treated like a commodity), a lack of innovation and a group that is directionless and not passionate.
  4. Find the available leadership hacks that others have tried.  Try them exactly as they are documented.
  5. If it works, report success to the community.  If it doesn’t work, report that, too.  You can post here, or on other leadership blogs.  Or start your own.
  6. If it doesn’t work, ask: what do the principles of leadership suggest I do here?  Use improvisation on existing hacks.  Combine hacks.  Report even partial success—others will take what you’ve done and add to it.

Along the way, remember that leadership hacking requires no formal authority in an organization.  And your organization may not welcome your leadership hacks, but they are necessary. Most organizations are dinosaurs, having to eat an enormous amount of food, and producing almost equal amounts of excrement.  Now that the environment is changing, they need to become more like warm-blooded rodents, that can move fast and get by on less food.  They need to be hacked for their own good.

Never, ever forget the golden rule.  Don’t use a leadership hack on others that you wouldn’t want used on you.


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