The Steve Jobs skill I found in our intern

Our killer Chief of Staff intern, Michael, has a superpower that most seasoned CEOs are still trying to master.

Young Michael will go on to do great things.  I'm extremely confident of it.  I shared this positive POV with him and watched his shoulders immediately react… Then he tensed up again.

"How do you know, Jesse?" he asked.

He didn't believe me!  He wanted cold hard evidence.

I told him I've hired 500+ people at his age over the last 15 years.  I gave him examples of how he works hard, is affable and has a fire in his belly.

It didn't satisfy him.  "EVERYONE has those traits at McKinsey, Jesse!"

He was right.

So what makes him stand out?

Then it hit me.  Michael possesses an extraordinary skill — one I rarely see in young people, or even in hardened CEOs.

Michael has the ability to fly at virtually ANY level of business.

What does this mean? Let me break it down.

This is where hedge fund managers and CEOs of super big companies operate.  They look ten years ahead, analyzing trends and moving chess pieces across the board.  They make strategic choices to invest in an industry or sell a business unit.

I think of this as the common "operational CEO" role.  They work with an executive leadership team.  They think one year ahead. They focus on initiatives, resourcing and performance.  They carry a clipboard.

This is where first-line managers (or startup CEOs) operate.  They manage workers directly.  They set the tone for the team.  They are responsible for who does what. They, ultimately, own what ships or what service is delivered.

This is where the DOERS live: The coders.  The hackers. The writers.  The designers.  These people get their hands mired in mud, obsessing over pixels or sentence structure.

Ok, Jesse, that feels pretty straightforward.  What makes Young Michael so special?

In my experience, the best founders and leaders can:

1. Fly at ALL of those levels

2. Switch between them DYNAMICALLY

3. Maintain SITUATIONAL AWARENESS (and self-awareness) to FLEX across levels as the business demands

And that's what Michael does.

Take Steve Jobs, arguably the best entrepreneur in history (still rings true even 14 years after his death).

Jobs saw the future at a time when BlackBerry said no one would move away from keyboards. He ensured his team of creatives shipped.  He wooed customers with incredible pitches.  He OBSESSED over pixels on the screen.

Jobs flew at every level.

Once you see this, you can't unsee it. Almost every great entrepreneur does it.

Did Jobs fly at all levels at all times?  Of course not, that's impossible. (But my buddy, Brett Adcock, comes close.)  And that is part of the genius.

Let's talk about the failure modes of this. Then I'll share my tips for developing your chops.

1) Inability to fly on a level

I DO NOT think any one level is better than the other.  They each require their own skills that need to be developed.  Sometimes founders excel at building products, but struggle with market positioning.  Some founders can't make critical decisions around people or resourcing.  They’re missing the 30K or 10K level.

Still, others can think out years ahead and have HUGE vision, but when it comes to sitting down and demanding high-quality work or writing something, they struggle.  They don't like the mud.

If you can't fly on every level, you will inevitably stall your business.  It may show up in the wrong strategy choice, an alienated team or the low quality of outputs.

2) Wrong level, at the wrong moment

EVEN if you can operate on all levels, founders sometimes jump to strategy when they should be focusing on execution.  Other times, they micro-manage when they should be coaching.

This is not easy.  When I learned to become a CEO, I used to say, "First you have to develop all the tools in your toolkit.  Then (much more difficult), you need to know WHICH one to use and when.”

Ok, Jesse. You've opened my eyes to these levels, their importance and how I f** them up.  What do I do now?*

Well, you build up your skillset.

1) Practice

Business is like anything else.  Reps and practice are how you learn and win.  EACH level requires its own practice and intention to improve.

Some specific suggestions:

• For the 30K-Foot View: Read The Wall Street Journal, talk to the investment community, schedule strategy sessions with peers.

• For the 10K-Foot View: Read management books. (Yes, seriously.)

My favorites are The Great CEO Within, The New One Minute Manager and High Output Management. Practice giving feedback and having difficult conversations.

• For the 1K-Foot View: Hold regular, hands-on conversations weekly or daily.  This is "micro-management," and there are likely a few parts of your business that need it RIGHT NOW.  Find one to two places and dig in.

• For the 100-Foot View: Create something!  Write, make a deck, code a product.

2) Awareness

This is a broad category, so let's split it into a few areas:

• Self-awareness: Know yourself!  That's where it always starts.  Which level are you more comfortable at?  When you're stressed, where do you go?  In this very moment, where are you flying and why?  Creating awareness will go a really long way.

• Feedback: Cultures of feedback allow for points of view and critical information to flourish.  If you aren't actively soliciting feedback you won't have the information to know where to fly. Ask the team where they see issues. Create simple, low-friction systems for sharing.

• Information: Think TPS reports.  They matter for similar reasons to feedback.  Customer surveys, revenue pacing, pipeline.  If this information isn't accurate and timely, how will you know what needs attention?

I find this to be the hardest for most CEOs.  They don't know what's going on with them, their people, their clients or their company. That makes them zig when they should zag.

3) Name where you are

This is sort of like self-awareness, but it's a tactic I've found so helpful.

When you are discussing an item, where are you flying?  Name it. Is it strategy?  Is it resource allocation? Is it execution? Or is it actually doing work?

Ask people, if that seems appropriate.

When you plan your week, think about where you should fly in general. In each meeting, ask that same question.

When something goes terribly wrong, think about WHICH level is required.  Does it need a different strategy or does the execution need leveling up?

Oftentimes for me, I mess this up when I avoid seeing the field clearly, and then I actually ask myself why it's not working.  Those questions go a long way.

Mastering the different levels of founding and leading a business is lifelong work.  They're some of the many fun "game" aspects to building something.  Now that you are aware of this, what level do you best operate at? At what level do you struggle most?

Have a great week!

-jesse