Letting Go – The Entrepreneur’s Dilemma

Having worked for many a small business in my day, and being an entrepreneur myself now, I have had the unique opportunity to see businesses grow and how the entrepreneur grows (or doesn’t grow) with it.  It’s a great example of a leadership lid because the business will grow to a certain point and then will either slow down drastically and stagnate completely.  It is not a factor of the economy or industry changes, but more a matter of the lack of changes internally.  The entrepreneur simply doesn’t grow his leadership enough to be ready for how the organization needs to change to accommodate corporate growth.

Wearing Many Hats is Heavy

letting go - too many hatsYou see, when you first start out you are quite often the only person doing anything or at the very least everything revolves around you.  It was your vision and your initiative that got things off the ground, so naturally you feel that you and you alone are responsible for success or failure of this venture.  And so you are the executive management, the accounting department, the sales manager, the fulfillment department, the development head, and perhaps even the janitor.

And then success happens.  Sales are up!  Customers can’t get enough of you.  You have to add staff, hire or appoint department managers, expand inventory, install processes, get more office space, create new products, adopt more formalized accounting procedures, and more!  You are spending more and more time in the office, being pulled in multiple directions, and things are bottle-necking because they have to wait for you to come up with a solution or put your stamp of approval on one.

THIS is the crisis moment.  It becomes a crisis because you haven’t yet learned to let go.  When the company has grown to the point where things are waiting on you, then it is time to decide what things you want to keep control of and what you want to let go of and trust others to carry the load.  When you can let go of things and trust the people you have hired to pick up the slack, then the pace of the business can continue and you can grow.  If you insist on keeping your finger in every pie, most of the pies will not come out right.  In addition, you will become weary and burned out and then……another small business bites the dust.

The Simple Solution – 80/20

Apply the 80/20 rule here.  Eighty percent of your efforts should be directed towards the 20 percent of things that you and only you can do; such as visioning for the future and preparing your legacy.  Look at what you do now and think about the things you do daily and weekly.  If someone else in the company can do it at least 80 percent as good as you, let it go.  If it does not focus on the primary thrust of your business, let it go and let someone else do it.  This is an important step in your leadership growth, not only because of what it does for you, but also what it does for your business and most importantly for the people in your business.  It allows others to grow and become more engaged and take responsibility for the profitability of your business.

“The best executive is the one who has sense enough to pick good men to do what he wants done, and self-restraint enough to keep from meddling with them while they do it. “
Teddy Roosevelt

Half the Battle

Easy, right?  Not even close!  You will likely resist this vehemently.  After all, how can you let any of this go and let someone else do it!  You created this, YOU had the vision, and how can anyone else know enough to do it the way you want it done!

We will talk about THAT tomorrow.

Action Plan

  • Apply the 80/20 rule.  What are the 20 percent of things that you and only you can truly do?  Be honest with yourself on this.
  • Make a list of what you are going to let go of.  Next to each one, write the name of the person to whom you will release it.


Leadership Trainer, Speaker, and Coach Paul SimkinsOn May 10, I helped sponsor (as a vendor) and attended Chik-fil-A Leadercast this year. Leadercast is an annual event where top leaders in business, education, politics, sports, and other areas speak on ways to strengthen your leadership. It is held live in Atlanta and simulcast to locations around the world. I was at Wycliffe Bible Translators in the Lake Nona area of Orlando.

Now, imagine being able to glean wisdom from the likes of John Maxwell, Andy Stanley, Coach K, Jack Welch, David Allen, Condolezza Rice, and others all in one day for one small investment! It was a tremendous experience and I highly recommend you plan to attend it next year.

Here is some of my takeaways from the speakers this year:

Overall Theme: Simply Lead

Andy Stanley (Author, Pastor, Founder of Northpoint Ministries)

  • Be okay with not being the best person in the room. Just lead.
  • Growth and complexity are intertwined. Leaders provide clarity in growth to offset it.
  • To find clarity, ask yourself “what am I doing? Why? Where do I fit into the big picture with my clients?”

David Allen (Author of Getting Things Done)

  • Find your serenity in a crisis in simplicity
  • Give yourself freedom to make a mess
  • Pay attention to what has your attention
  • Get things off your mind and on paper
  • Define it, refine it, date it, map it
  • Make your mind like water, flowing into and filling the gaps and adapting to your container

Sanya Richards Ross (Olympic Champion)

  • Focus on who and what you are
  • Henry Cloud (Author of Boundaries and Necessary Endings)
  • Don’t be afraid to get outside help to do what you must when you ain’t
  • Leaders bring necessary endings in situations both good and bad
  • Prune away what isn’t core to your purpose and vision
  • Who’s your monkey? Monkeys cling to and support one another when things are not well. Who is your monkey you can depend on

John C. Maxwell (Leadership Guru and Author of over 70 books)

  • As communicators we try to complicate things, but need to keep it simple
  • Move people from simplistic to complex to simple
  • Do your math:
    • add value to someone everyday
    • subtract your leadership landmines
    • multiply your strengths by developing them
    • divide your weaknesses by delegating them

Mike Krzyzewski (Coach of Duke Men’s Basketball Team and Team USA)

  • Leaders bring out the best in the team

Condolezza Rice (former Secretary of State, College Professor)

  • The key in complexity is to see simplicity
  • Beware enabling condition
  • Lead where you are

Jack Welch (former CEO of GE, author)

  • Go after your passion with everything you got
  • You have no right to be called a manager if your employees don’t know where they stand
  • Develop the generosity gene
  • Move with self-confidence, simplicity, and speed
  • Fear but go for it
  • No amount of productivity overcomes the wrong attitude, so prune away those whose attitudes are not consistent with company culture and values
  • Over-deliver always

LCDR Rorke Denver (Seal Team Instructor, author, film star)

  • Give the extra inch of reach and do it yearly
  • Calm is contagious. So is panic. Exude calm.

Again, I highly encourage you to plan now to attend next year in May.