Thinking Like a Leader

I’ve read a little about executive coaches in various blogs.  I always chocked it up to advice for 20 something CEO’s fresh out of college tech programs who really don’t understand how a business works.  A few months ago we started a program at Fido that I didn’t even realize was coaching until I looked up the facilitator.  Free plug to CRA.  I have to admit, I am a convert, it was an exceptional experience.

I didn’t necessarily have 1:1 coaching, but our group of 15 or so Directors formed a pretty good bond over the 4 months.   In some ways I think I actually got better perspective by John introducing topics, concepts and best practices, and then letting the group provide color based on experience.  It was certainly beneficial to me as I always thrive on alternate perspectives.  Some I agree with and some I like to sample, if for no other reason than to excercise my thought process for disagreeing.  Some of what we learned is universal, I’ve even used some of it with the girls.  We had a great discussion last week about how Megan and I can trust them to do their jobs (school, chores, sports), treating us as a ‘boss’ that grants them more responsibility as they perform at a higher level.

But I think most of the really good stuff was about not following the tradewinds.  Leaders have a good idea of what they believe will work and then spend their time not convincing you that they are right, but helping you see that vision as the utopia it is.   Successful leaders actually build what they concepualize.

For the last session we all read an essay, that I have to say is one of the most insightful discussions of leadership that I have read.  It is a lecture that was given at West Point in October 2009.  A few things stuck with me.

  • “That’s really the great mystery about bureaucracies. Why is it so often that the best people are stuck in the middle and the people who are running things—the leaders—are the mediocrities? Because excellence isn’t usually what gets you up the greasy pole. What gets you up is a talent for maneuvering”
  • About David Petraeus (pre-affair) in the context of the Counterinsurgency Field Manual   “No, what makes him a thinker—and a leader—is precisely that he is able to think things through for himself. And because he can, he has the confidence, the courage, to argue for his ideas even when they aren’t popular. Even when they don’t please his superiors.”
  • About a study of college students multi-tasking “…people do not multitask effectively. And here’s the really surprising finding: the more people multitask, the worse they are, not just at other mental abilities, but at multitasking itself.”
  • Which leads to “Multitasking, in short, is not only not thinking, it impairs your ability to think. Thinking means concentrating on one thing long enough to develop an idea about it. Not learning other people’s ideas, or memorizing a body of information, however much those may sometimes be useful.”
  • And most importantly “I find for myself that my first thought is never my best thought. My first thought is always someone else’s; it’s always what I’ve already heard about the subject, always the conventional wisdom. It’s only by concentrating, sticking to the question, being patient, letting all the parts of my mind come into play, that I arrive at an original idea.”
  • I wrote about some of this before, but I like this passage about sourcing news/ideas from Twitter or Facebook “…you are continuously bombarding yourself with a stream of other people’s thoughts. You are marinating yourself in the conventional wisdom. In other people’s reality: for others, not for yourself. “

One of the most important themes I took out of the sessions was the need for me to be me.  Every so often I slip into a mode of feeling that I need to play the Fido corporate game and figure out the best way for me to move ahead.  It forces me to want to check my creative self at the door and build a team that reaches concensus and presents an integrated approach to some idea that really doesn’t do much of anything in the world.  But when I think about what that means, about what i would actually have to do, I am disheartened.  It shouldn’t have to be like that.  I want to do great things and make a difference in the world.

I remember reading that Bill Gates used to take a few weeks every year and get some solitude with a stack of whitepapers and notebooks (he probably went to The Yellowstone Club…jealous).  To a lesser extent, I have done this up in VT, but it is something I really want to focus on in 2014.  Finding time to think, imagine, and strategize.  If I am going to be successful, it will only be by imagining the way that things should be, and then executing a plan to get there. 

The class inspired me to really start moving on my startup and focus on making that happen.  This has been years in the making, but I am finally getting around to making it real.  As we roll into 2014, you will see my posts become less political and more focused on making this thing successful.  Please stay tuned, my best, most thoughtful and forward thinking work is right around the corner.

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About Josh Rutstein

I am an aspiring entrepreneur and hopeful political candidate. Father of 2 very special girls and passionate American. I snowboard whenever possible and follow a 20x mentality for exercise. I also play golf and ultimate frisbee and am a die hard New England Patriots fan and season ticket holder. Everyday I wake up wanting to make this country a better place, someday I hope to actually succeed.
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