Leadership Lessons From the School of Hard Knocks

Leadership Lessons

Leadership Lessons

Leadership is a state of mind.  A strong leader can move mountains by skillfully rallying his or her team behind a common, well-articulated mission.  I have found that this is most directly accomplished by cementing in the minds of the team a mission worthy of achievement.  For leaders, investing one’s leadership skills is equally challenging whether the goals are big or small; hence, I encourage you to embrace BHAG (Big Hairy Audacious Goals) with a “Change the World” vision.  Always ask yourself, “How do I play in a bigger game?”  Having said that, it is important to “walk before you run,” but don’t be scared away from giant ideas that you are genuinely committed to see through to reality.

In order to succeed with an idea, it is the job of a leader to successfully recruit the best, brightest and most talented people that can be attracted to the cause. And, then the real work comes when the leader must unite those capable people to work together harmoniously in ways that deliver amazing results that dwarf what could be accomplished by the sum of just those individuals.  Leaders create “new math” where 1+1+1 can equal 8.  Leaders must look for those opportunities.

Here are some tips for entrepreneurial leaders that I provided in a recent lecture at the Massachusetts Institute of Technology:

Be Bold

  • Shooting only for incremental change doesn’t create a disruptive, high-value organization (or service or product).
  • At ChaCha, we’ve attacked a GIANT world-changing idea:  providing incredibly helpful, highly relevant, timely, fun answers to a global market of over 4 billion people on their mobile phones and online.
  • Few thought ChaCha could overcome challenges such as scaling a human army that helps answer questions, which allows ChaCha to be that “smart friend” that’s available anywhere, anytime.  From the beginning, we loved hearing “that’s just not possible.”  We took a counter-intuitive approach of bringing people back into the loop for challenges that are typically solved today with algorithms.  We set out to solve the ubiquitous problem of how hard it is to effectively use traditional search engines to get information on mobile phones, and to do it cost-effectively, at a price that people will afford (In this case, we made it free).
  • Moral: If you have a solid idea, don’t let the masses and common opinion steer you away from it.  AND, simultaneously, you will personally need to objectively challenge your own vision to determine if you’re on the right track.  Surround yourself with advisors, consultants, and friends who help you think objectively.

Be Passionate

  • Choose to lead when you are genuinely passionate about something:  As your barometer, do YOU and your team LEAP out of bed each morning to tackle the mission, strategy, and tactics?
  • You and team won’t be able to “Do whatever it takes” unless you are passionate.

Fail fast (and tune up)

  • “Fail Fast” is our culture at ChaCha.   When things aren’t working, can you figure out what parts aren’t working and shed them quickly?  The trick is learning how to notice and retain the parts that can work.
  • If we didn’t try different approaches at ChaCha, we would never have found a path to revenue today.  Our original business model started online as a search engine where our guides would chat with people who were searching online.  That didn’t resonate particularly well with users, but when we shifted to offering virtually the same service on mobile phones, the service took off like a rocket!  Then, a year later, we took the mobile Q&A content and put it back online, where it has become the most extensively-curated Q&A dbase available online, thereby bringing revenue-generating traffic to the website too.
  • The moral of the story is to fail fast, tune up, and don’t rule out that an early failed idea might succeed later in a different context.  Many of the things that initially “failed” in my businesses eventually ended up morphing into something valuable.

Lead by example

  • The leader must set the pace, the “whatever it takes” culture, and the “can do” attitude.
  • A few years ago, my robot team was competing in the “DARPA Grand Challenge” 150-mile autonomous robot race through the Mojave desert (using NO remote control of a 6000 pound robotic vehicle that could move at 90 mph).  In the months leading up to the race, we realized we weren’t hitting our goals so we moved the team from our Indiana headquarters to the Mojave desert for the month preceding the race.  By changing the venue, we transitioned into a round-the-clock, whatever-it-takes, fail fast, laser-focused team which produced results at 10x our normal pace.  Be willing to step outside accepted norms when the situation demands it.
  • Again, it’s OK to fail, so long as you “fail fast” and move on.
  • At appropriate critical phases of the company, remember that hard pushes are absolutely required, and it’s YOUR job as the leader to rally the team.  In those times, I personally believe in the concept, “whatever doesn’t kill you, makes you stronger.”

Aggressively fill skill gaps

  • Surround yourself with the best possible talent, always.  And that may change over time.
  • Look for your gaps.  Inspect gaps in the team.  Learn how to be objective at assessment of skill gaps.  Your constant acid test is you asking yourself:  Is there anyone in the world who could do this task better?  If so, how would I recruit that person?  Or, how can I measure our current team (or a particular individual) against the gold standard?
  • Complement your experience and skillset.   Ask for help wherever you can find it, internally or externally.  This is critical. If you are a true leader, pride and useless emotions cannot stand between you and the primary mission.  Watch for this dynamic from other leaders on your team also.
  • Build a walk-on-water internal team, and surround yourself with the best external advisors you can attract.  You might be surprised at the quality and level of the people you can bring into your circle, if you’ve learned how to sell your story (which is another reason to take on BIG ideas).
  • As an example at ChaCha, when it was deemed that we didn’t have sufficient new media expertise, I wasn’t too proud to go out and seek help……and I now we have a world class (and very active) advisory council.

“Safe Debate”

  • Create a culture that invites intellectual debate in a “safe” environment.   This applies internally and with your Board or advisory groups.
  • As a leader, it’s essential to be a “good listener”, BUT THEN be able to rally the team around the best solutions.

Give back

  • Find ways to give back to your community, to schools, to charities.
  • As a leader yourself, I invite you to help create the leaders of our future through a program I’ve recently helped bring to Indiana.  Please join me in making a difference in the lives of over 5000 future Hoosier entrepreneurs.  Consider the impact of helping children understand early in life that they can move an idea from drawing board to reality themselves.  (They can earn $150 in one Sunday afternoon, buy that thing they’ve been wanting, put some cash into a new savings account, and learn to “give back” to charities themselves).  With a little bit of hard work and ingenuity, those children learn that they can shape their own destiny.  Lemonade Day provides powerful life lessons.  I hope you’ll help me bring this very impactful (and fun) program to Indiana this year.  There are about 20 more days for you to help get this off the ground.  You can find out more at www.lemonadeday.org/indianapolis.


  • Think BIG!!
  • Change the World!
  • And, above all, have FUN!!!

~ Scott Jones

Ask me absolutely anything at www.chacha.me/scottjones!

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