“The Boss,” a Successful Leader & Role Model for Taking Calculated Risks in a Leadership Role

The difference between exceptional leaders that get outstanding results for their organizations, and those struggling in leading their people, is that the former take calculated risks, despite the fear of potential failure.

What is your risk tolerance and when do you know you’re ready to take that leap?

Are you the perfectionist that waits ’til everything, including all the moon phases, are aligned?

Consider this, if you were making a presentation in front of your very best, most dedicated customers or employees that have the highest loyalty and regard for you, would you risk presenting something that you felt was only 80% ready to go?

Two weeks ago, one of my musical heroes, Bruce Springsteen, aka “The Boss,” did that very thing. It was on Friday, September 21st at New Jersey’s MetLife Stadium.

With 65,000 people anxiously waiting on Springsteen and his band to take the stage, Springsteen chose to open the concert with a song he and his E Street Band had never played in front of a live audience.

But, more important than that, the song was, in my amateur estimation only about 80% ready to be played live. How do I know that?

Because “The Boss” screwed it up! (see video below)

He forgot the words! He took a risk and failed!

In the age of the contrived, coddled, lip-syncing celebrity live performer, this type of risk-taking is extremely rare.

But, you know what? Springsteen survived.

Not only that, in my estimation, he thrived.

When the show was over most of the hardcore fans agreed it was one of his best live concerts ever (and as many of you reading this know, I’m a connoisseur of live Springsteen shows, this was my 76th, followed by my 77th the next night).

Opening the show with this song was a huge risk.

First, it was a rarity. A song only hard-core fans would be familiar with.

Springsteen risked alienating a football stadium full of people coming to see a superstar perform. Somewhere between 20-50% of the 65,000 were long-time, hard core fans, for whom this song was played, but what was he focusing on in that moment when he made the decision to play that song?

The focus that drove that decision is the singular difference between becoming a world renown rock and roll superstar and someone floundering in the obscurity playing weddings and bar mitzvahs.

As aspiring organizational leaders what we choose to focus on when making risk-calculating decisions can be the difference between building a resume of achievement and waiting for opportunities that never seem to be right.

In front of 65,000 people Springsteen had the confidence to open a show with a song that wasn’t 100% ready to go and even more importantly he had the humility to laugh at himself in the moment. Watch the video below to see what happened and how Springsteen reacted (this is taken with my IPhone from perch just a few feet from the stage that I was lucky enough to secure).

The video picks up about half-way through the song right before Bruce realizes he’s lost his place. At about the 50 second mark of the video Bruce picks up the lyric sheet to read the words from it:

This is not the first risk Springsteen has taken in his career.

The biggest one occurred in 1977 when he filed a lawsuit against his manager that got him his first record contract and got him on the cover of Time and Newsweek Magazines the same week in 1975 just one year after he released a hit record.

This lawsuit kept him from recording for 2 1/2 years at a very critical time in a career and an industry where fame is fleeting. Five years later, after releasing his most popular pop music to that point, he released a dark and stark solo acoustic record against the advice of many.

Leaders need to take calculated risks. The small business leaders I come across often procrastinate on key decisions, waiting for the perfect time. Waiting on perfection is a losing proposition because perfection will never be reached. On September 21st, Bruce Springsteen showed us all that taking calculated risks can be done, and be done successfully.

One of my business mentors, Alan Weiss, always encourages us to take action on an initiative when we think it is 75-80% ready, not 100%. If we wait for it to be perfect it ain’t ever gonna be, and we miss tremendous opportunities. Springsteen went for it when his song, “Waiting on the Edge of the World” was 80% ready.

One final important point, Bruce recovered extremely well because he had the humility to laugh at himself (which you can see in the video), and move on.

Something all of us small business leaders can learn from.

’til next time, make it a great week!

6 thoughts on ““The Boss,” a Successful Leader & Role Model for Taking Calculated Risks in a Leadership Role

  1. Eswari Kalugasalam Lawson says:

    I once worked for a boss ( and I have many), who told me that you can never be 100 percent sure that the decision you make is the right one unless you are God. I learnt over the years, that mistakes will be made, you will learn from the mistakes and you take responsibility for those mistakes. Share the lessons learnt with your team. For they too, will learn that it is okay to make mistakes and learn from them .. and that makes them take ownership of their duties and their roles in the organization.

  2. Skip Weisman, Workplace Communication Expert says:

    Thanks for your comments. You are absolutely correct. Unfortunately, not many bosses have that attitude and create an environment where people are afraid to make mistakes. This is because they have not developed within themselves the confidence to lead people in a way that allows them to communicate for development and instead communicate to control.

  3. Tonya Pomerantz says:

    Wow! Thank you for this. As someone who shares your feelings towards Bruce Springsteen, I appreciate the video and the article.
    I agree – he certainly took some calculated risks in his career, and ultimately his life.
    Confidence is a fundamental factor in not just a strong employer, but a strong and engaged employee as well. With action comes confidence, and with confidence we realize that we will survive those imperfect moments.
    Thanks for the post,

  4. Skip Weisman, Workplace Communication Expert says:

    Tonya, Thanks for stopping by and being inspired to leave a comment. I appreciate you reading my blog and I especially love having other Bruce fans in my world. Please come back and contribute to the discussion again. You’re always welcome! Can’t wait for this Thursday night in Hartford, my 78th live Springsteen performance!

  5. Tonya Pomerantz says:

    Oh Skip!
    I would say I am jealous, but truthfully I am just happy that you are getting to see him again.
    I have spent the entire evening listening to TRACKS and I will be going to sleep listening to Springsteen Radio.
    Have you written about Springsteen before? I am delighted that I found your blog and have bookmarked it and will be subscribing to it.
    Here’s to a magical 78th!
    Take care,

  6. Skip Weisman, Workplace Communication Expert says:

    Well, your comment inspired me to republish an article I wrote in 2007, which was posted on my old website and never republished here. You can find it at this link


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