About the author : Clifford Jones

Founder and "Chief Revenue Guy" at Clarity Strategic Advisors, LLC. Author, speaker, entrepreneur. Learn how to get better sales and marketing results, guaranteed.

Sally is a brilliant entrepreneur. So why does she stink at leadership? Well, it’s not unusual for many of the best entrepreneurs to stink at leadership. This is a story about one entrepreneur with a big vision and an intensity that scared many who worked with her away.

Have you ever met a brilliant person who couldn’t seem to get along well with people? Imagine a super-high energy woman with tons of vision and drive, who seemingly never stops grinding forward to the next goal. Meet Sally, as I’ll call her, the quintessential entrepreneur.

I got to work with Sally and her small team several years ago. I’ll never forget her relentless, frenzied approach to making sales and marketing work. I share this with you as an example of how to align great entrepreneur talent with leadership skills. It’s an honor to work with the Sally’s of the world.

The reason Sally had issues producing results was most of the people Sally hired found her too intense and at times, overbearing. As a result, there were only two people on Sally’s team who could keep up and keep Sally happy. There was a ton of work that needed to be done and nobody qualified to do it, like run the marketing automation as one example. The bottom line is when I showed up the team needed leadership help.

Leadership Defined

Sally is a great entrepreneur, but not the kind of leader many will follow. Let’s look at the definition of a leader, then an entrepreneur, from a literal sense.

See the keywords for a leader?

“Directorship, governance, administration, guidance, direction, management, supervision.”

Not Sally.

What happens when Sally hires and aligns with a business leader who can help her close the leadership gaps? Good things, as you’re about to see. A move like this can be outsourced, as was the case with Sally, or it can mean hiring a full-time person to lead the team while you be you, the hard-charging, take-no-prisoners entrepreneur.

The Entrepreneur Defined

Now let’s look at the definition of an entrepreneur. Please understand that it IS possible for entrepreneurs to possess amazing leadership qualities, but in my direct experience in the small business consulting world, it’s not common to have both.

Organizes and operates (wears 9 hats!) the small business herself, “taking on greater than normal financial risks in order to do so.”


Ever meet an entrepreneur who DID NOT who didn’t get stuck in “technician” mode, meaning buried in doing all the work; baking the pies, washing the pots, making deliveries, doing the books and more? If there’s little or no time, ability and willingness for the true entrepreneur to be an effective leader, they must delegate leadership to someone who will work well with them and the team.

L:eaders tend to work more “on the business” from a strategic and organizational view. Entrepreneurs may be capable of these exhibiting these qualities, but often are so mired in the operational struggles to manage the business there is little time, energy or desire remaining to pull away from the day-to-day grind and refine the vision and plan based on results.

How Do Small Companies Get Big?

Short of luck, company growth happens when great leadership combines with amazingly-entrepreneurial talent in a way that the team aligns, performs and produces a measured result over long periods of time.  The right team of people come together and work hard to follow the vision, mission and plan of their stable, qualified leader.

It’s that simple. No way around it. Leaders need to be good at leading. The measure of a great leader is the people who follow him or her. Just look who’s following.

Most true, entrepreneurs and small business owners struggle with stable leadership. They also struggle to keep the right people working for them; people who can get the detail work done that they are accustomed to controlling and doing themselves. Small businesses fail most of the time because of the owner’s inability to plan and make effective decisions allocating a finite amount of capital, especially time. It’s just too hard to succeed without the right combination of leadership, entrepreneurial and management skills.

What Happened To Sally

Let’s wrap this up by revisiting what happened with Sally’s new plan and team. When I worked with Sally there was no question in my mind that she was a true entrepreneur. There was no way she was going to fail, no matter the cost. But the cost of churning through people to grow her business was massive.

Sally needed help with leadership, a crystal-clear strategy, a plan of action for her team to follow, and three, key positions filled to get the results she told me she wanted.

Here are the three roles I helped Sally fill to BEGIN closing the “people performance gap.” (Think normal timeline for a turnaround like this is 6-9 months if everyone does their job right the first time.)

  1. Chief Marketing Officer – This person needed to be extremely strategic, but able to manage the tactical execution of the digital marketing plan. Sally’s marketing took place online.
  2. Web Design & Development – This needed to be one person, even though design and development are different, complimentary skill sets. But budget constraints and the ability to find a great, outsourced fit closed this gap.
  3. Sales Administrator – This person needed to run the Customer Relationship Management (CRM) system, the marketing automation software, as well as manage all the projects related to marketing, recruiting, payroll, etc.

The good news is the marketing lead in this case was me. Because my leadership experience and style helped Sally feel more confident and clear in the new plan of action, we quickly got on the same page to fill the roles crucial for our success.

The Plan Worked … Until

Sally and the team started seeing better sales results within 30 days. The new, core marketing campaigns got finished and launched, and they produced new leads for the first time in a while. We built a real sales pipeline, optimized the CRM and automation, and the systems began working great.

Sally was happy because she was getting what she wanted; a sales pipeline that was growing. This happened because finally, people could work under her highly-entrepreneurial style, complimented by my leadership abilities to assemble and lead the marketing team. My leadership skills melded beautifully with Sally until Sally made a crucial mistake.

Ever meet an entrepreneur who changed her mind too much? This is not always a bad thing, but if too pervasive a habit of the owner or leader/entrepreneur, the more likely you’ll lose people, flow and any newfound gain in performance.

In the end, Sally got impatient. She decided to completely shift strategic and tactical gears after about 3 months of the new plan and work. This sudden, drastic shift in focus threw the new team into a tailspin, and Sally found herself two steps back, once again.

The moral of this story, and countless others like it is this: Small businesses only become big companies when leader, entrepreneur and team align to the same goals and plan over long periods of time.

We need the Sally’s of the world to start things and fire us up, always daring to be different.

We also need stable, high-EQ business leaders to compliment the entrepreneurs who all know and love.

Got a question, comment or concern?

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About the author : Clifford Jones

Founder and "Chief Revenue Guy" at Clarity Strategic Advisors, LLC. Author, speaker, entrepreneur. Learn how to get better sales and marketing results, guaranteed.

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