by Christopher Meyer on 06/29/2015


President Obama discussed with comedian Mark Maron how the ups and downs of six years in office had made him a better president (paraphrased below).

As you get older, you might slow down or not jump as high as you used to.  But I know what I’m doing and I’m fearless.  This is not pretending to be fearless. Part of that fearlessness is that at this point in life, I’ve screwed up a number of times.  I’ve been in the barrel tumbling down Niagara Falls and I emerged alive.   You lose the fear.

I was struck by Obama’s tone and timing. In that instant, Obama was freestyling his thoughts as a rapper would lyrics.

Unpacking Fearlessness

Obama’s comments caught my attention because fearlessness is as elusive as it is attractive. For me, the opposite of fearlessness is rarely fear but the overuse of rational thought. As long as I stay with analysis, I’m protected from experiencing the results of doing something.  I may not succeed but I’m also guaranteed not to fail.

Few will argue with getting more facts.  That would be foolhardy, not fearless. Right?  Perhaps, but we’ve all reached that point where the insight gained from additional facts begins to wane.  The cost of delay becomes obvious.  What about those decisions where the cost of delay was higher before it became obvious? That’s where fearlessness might help.

Then there’s the bias that decades of critical thinking in academia, consulting and executive roles adds to my worldview.  My “what if” analysis starts with an unstated bias that highlights what could go wrong.  I can’t think of a pitch meeting with an entrepreneur that didn’t eventually turn into a grilling about such scenarios.  Rarely do these meetings begin by looking at what opportunities they might have missed in the “what if things go right” setting?

This could suggest that being more optimistic and action oriented is core to fearlessness.  Perhaps it is, but not if it overrides using our experience.  Experience and logic determine how we make sense of facts.

Obama’s decision to launch the Bin Laden raid provides a good example.  According to Robert Gates, Obama’s more experienced and conservative Secretary of Defense, Obama described the dilemma as “a fifty-fifty situation no matter how you look at it.”  With far more experience, here’s how Gates viewed the same set of facts:

  1. Succeed or fail, the raid would endanger an already fragile relationship with Pakistan – key to succeeding in the war in Afghanistan.
  2. Pakistan’s intelligence service (ISI) could know that Bin Laden is there and have a protective ring around the compound.  At a minimum, they might have more eyes on it than we know.
  3. Worst case, Pakistan could surround the compound and pin the SEALs down.
  4. Gates had multiple examples of failed similar operations with compelling reasons for each that were relevant.

Gates summed up his concerns, “It is a compelling case, for what we want to do. I worry that it is compelling because we want to do it.”  What he did next speaks loudly to both his and Obama’s character.

Gates then told the President that perhaps his experience was doing him a disservice because it made him too cautious. Obama forcefully disagreed, saying that Gate’s concerns were exactly what he needed to take into account as he weighed the decision.  Obama’s fearlessness didn’t come from avoiding the facts as stock Hollywood hero footage might lead one to believe but by embracing them.  Both men knew that not advancing might enable Bin Laden to escape again.

On April 28, 2011, President Obama polled his team.  Gates voted for a drone strike.  The following morning, two of Gate’s aides appeared to try and get him to support the raid.  After further delibeations, Gates called the President’s office to tell him he now supported the raid.  Obama had made the go decision an hour earlier.

Fearless Leaders

Obama described his personal fearlessness.  Just as important for leaders is how to evoke fearlessness in others?  George Fisher, CEO of Motorola when they were at the top of their game, defined leadership as getting people to do that which they would not ordinarily do. It’s my favorite definition of leadership because it captures the toughest leadership challenge: inspiring change.

This is where optimism really matters. I couldn’t think of a fearless leader who wasn’t optimistic.  In fact, while exceedingly demanding to the point of being abusive, successful leaders such Steve Jobs and Elon Musk evoke followership because of their confidence. Being fearless and pessimistic are incompatible.  But fearlessness takes more.

To pull others along, fearlessness has to reach beyond the facts of the moment.  When facts speak loudly, the risk-reward equation is self-evident and lends itself to broad communication.  Fearlessness embraces a higher calling that overrides people’s natural fight-flight instincts to step into a risky void.  Fearless leaders incite something in others that enables that first step.

Fearless leaders don’t stop at the first step.  They widen people’s definitions of success and failure beyond win-lose.  Long before cross functional teams were the standard approach for innovation teams in high tech, I worked with Quantum hard drive President David Brown to transform their product development from a traditional serial and functional approach to what many viewed as a radically inspired team structure.

Brown’s fearlessness was not based on overwhelming confidence that we had the perfect answer.  Rather, he openly declared that there would be some bumps along the way that would require adjustments.  What they were, he didn’t know but he was confident that we could make course corrections.

Inferences and Queries

Queries are questions that Quakers use to guide self-examination.  Rather than the “thou shalt or shalt not” rules of most religions, queries are a framework within which Friends assess our convictions and consider the direction of our lives and the life of our spiritual community.

This piece ends with my queries rather than answers.  Add your own.

  • When do I dig for more data to avoid action?
  • When could asking “what could go right” be more helpful than “what might go wrong?”
  • What are the escape routes and signals I could watch for to course correct if necessary?
  • Where has fearlessness served me in the past that could convince me to be so at this moment?

Decimal Point Thinking:
Good for Operators; Dangerous for Innovation

June 19, 2015

Winter in Detroit is rarely pretty.  Pristine snowfalls quickly turn to grey slush that outwits the best pedestrian avoidance maneuvers.  Once that happens, your feet are cold and clammy for the next three hours.
It was on such a day that a new product team was presenting their “comeback” car design to a panel of senior [...]

Read the full article →

The Day After: Apple’s PayPal 2.0

September 10, 2014

I wrote yesterday’s piece before Apple’s product announcement.  While crafting a response to an email comment I received this morning, it struck me that a post-introduction piece might be in order.
In short, the iPhone 6/6 Plus will cover profits, the Watch will spur innovation and Apple Pay is the potential game changer.
Apple’s Passion for Profits

Read the full article →

Apple New Product Introduction:
Welcome to the Planet of the Ape

September 9, 2014

In a couple of hours, Apple executives will take to the stage.  And millions will be watching because part of our love for Apple is being co-conspirators in the OMG introduction process. While reverence for Steve Jobs will keep “incredibly insane” product descriptions off the table, expect to hear the word “amazing” more than once.
However, [...]

Read the full article →

Zen Start-up Lessons:
What Nest Labs Can Teach Entrepreneurs

February 14, 2014

Nest Labs makes a smarter, Internet- connected thermostat that sells for two to three times conventional models.  Most recently, they’ve introduced a similarly empowered and priced smoke detector.  You might ask if you need a smarter thermostat or smoke detector?  You’ll have a chance to answer that for yourselves in a moment.
Nest was founded by [...]

Read the full article →

The Minimum Viable Business School:
Zipcar Education for Entrepreneurs

February 7, 2014

The hotbed of education experimentation in Silicon Valley are the startup academies, accelerators and hacker boot camps.  Grounded in the minimum viable product philosophy that entrepreneurs harness to speed products to market, these new education entities offer a minimum viable education for tech entrepreneurs.
You know it’s hot because the regulators have come out of the [...]

Read the full article →

Apple New Product Strategy: “Siri…What Did I Miss?”

October 23, 2013

With yesterday’s product announcements Apple confirmed that writing about Apple these days is pretty boring.  No question engineers and designers worked hard to squeeze the iPad line thinner and lighter but, yawn, they’re iPads…now with some free software.  Who hoo.
For those who haven’t moved on to another site, Apple’s actions suggest:

Demand is strong enough to [...]

Read the full article →

Apple’s 2014 New Product Strategy

June 16, 2013

Will Apple Ever Release a New Product?
– headline from this week’s Street.com
The above is just the most recent variant in the continuing drama “Apple After Steve Jobs.”  Investors yawned at this week’s rollout of the new iPhone operating system (IOS).  Noting the new IOS visually apes Microsoft’s two-year old Windows Mobile tiles, the pressure [...]

Read the full article →

You Can’t Be Serious!
The NSA is Monitoring Our Calls & Email???

June 11, 2013

Where have you been?  And so what if they are?  My president tells me they’re not listening live.  It’s like a week-old Facebook feed – who cares?
Besides, they only have my phone number but that doesn’t mean they also have a reverse directory, does it?  And since they’re listening, maybe the NSA should pay a [...]

Read the full article →

The New Corporate Giving Pledge:
An Alternative to Apple’s iAvoid Tax Strategy

June 5, 2013

“Apple has always believed in the simple, not the complex. You can see this in our products and in the way we conduct ourselves.”
Tim Cook in testimony before the U.S. Senate, 5/21/13

Not That Simple
It’s simple to understand avoiding corporate taxes.  But crafting subsidiaries nestled in virtual crevices between international taxing authorities or [...]

Read the full article →

The New Normal Hits Movies

May 21, 2013

Instead of watching Washington pundits dissect the AP-IRS-Benghazi drama closing in on No Drama Obama, I went to an action movie.  I couldn’t help but notice two things.
First, without advertising our world would be a blank slate.  Second, if movie previews are any indication, our world will shortly be a blank slate.
Advertising as Entertainment
Imagine the [...]

Read the full article →