Get Your Organizational Wheel of Fortune Spinning

A couple of months ago, I had a two week period when many of our CEOs were leading their own 360 degree reviews, where feedback is provided to them by both their direct reports and by the Board of Directors.  If you are a CEO/entrepreneur, I would highly encourage you to do this, as it is a chance to get feedback in a structured, formalized way and to surface issues that can be addressed before they fester and become harder to overcome.  It is also helpful as the skills and management style that worked when your company was 10 people may not be the same as the skills required and the approach you take when you are 50 people or 500 people.  

As part of their 360 process, one of our companies ran a structured workshop in advance of the review to identify what the Board, the CEO and the company’s outside advisors felt were important characteristics and skills the CEO required to be successful.  Here at Flybridge, we also have an internal set of questions we ask ourselves as venture investors before we get involved in a company that helps us as a partnership determine if a given entrepreneur is someone we want to be in business with. Putting these together, below are six questions that you may want to ask yourself, about yourself, as you think about starting a company:

  1. Are you a Pied Piper?  To me, this is a unique skill that allows entrepreneurs to articulate a vision for their company, instill confidence in their ability to achieve that goal and demonstrate personal leadership that leads prospective employees, partners, customers and investors to feel like they absolutely have to join the parade.  These are both personality traits such as authenticity and trustworthiness, but it also means having a unique perspective on a market need and how your solution addresses that need.
  2. Are you introspective and coachable?  Because no one executive has all the right skills and the needs of the leader change as the organization develops, understanding your personal strengths and weaknesses is critical.  This does not mean a lack of confidence; in fact some of the most confident CEOs we work with are the best at understanding where their talents lay. If you have an interest in learning more, A good resource on this front is Daniel Goleman’s book, Emotional IQ. Of course, to be successful you then need to build a team (see #3 below) that has complementary talents to your skills.  
  3. Can you identify, recruit and retain talent?  This is fairly self evident, but I have observed over the years that some companies are great recruiters and have a way of attracting the best people while others constantly struggle to do so.  And yes, the old adage of A players attracting more A players while B players attract C players is true and is something we have observed repeatedly over the years. To be a great recruiter requires constant networking, a disciplined and intense interviewing process and great follow through and sales skills.  I love some of the approaches Paul English, the co-founder of Kayak, uses as outlined in this article.
  4. Can you create alignment across your team in terms of the company's strategy and objectives? Often an entrepreneur is so convinced their way is the correct way, they fail to realize that the rest of the organization may not understand, or buy into, the path forward and will be, as a result, inadvertently working at cross purposes.  This si not to say debate and conflict across the team is bad, in fact it is critical, but coming out of the discussion there needs to be by-in and alignment.  As an example, I was at a Board meeting at the start of the year where we joked that the CEO must have had a button under the table that allowed him to direct each of the team members comments as everyone's strategy and goals for the upcoming year was 100% aligned with the direction the CEO had laid out for the company in the session he had with the Board alone.  Not surprisingly, since that Board meeting, the company has met all their goals and objectives.  Further, because everyone understands and believes in the goal, any mid-course corrections and decisions can be made quickly as there is a common understanding of what needs to be achieved.
  5. Can you operate at a fast clock-rate and make rapid, data driven, analytical decisions despite rampant ambiguity?  I believe start-ups win in part because their decision making cycle is faster than their would be competitors, so being able to make rapid decisions is critical, despite the fact that often there is very little information at hand to make such decisions.  Some translate this into swinging from the hip decision making, but I think the real skill is understanding the ambiguity, asking the right questions in terms of what information would help reduce the ambiguity as quickly as possible, overlaying that information with input from trusted team members and advisors, pushing forward with decisive action and then reacting if need be.
  6. Are you resilient enough to look at adversity and focus on what needs to be done to overcome the challenges and adapt as necessary? Like a shark that can't stop swimming, startups continually need to be moving forward and when the inevitable turbulence arises, it is important that a game plan to overcome the obstacles be quickly put into place, even if the execution of the game plan will take some time.  If the path forward is not obvious, a starting point at a minimum is developing a plan to get to the plan.  Further, listening to input and being willing to adapt, even if it means admitting the original vision has flaws is an important skill, although often easier said than done for strong-willed entrepreneurs

Interestingly, these skills together can be reinforcing in a positive manner.  I call this the Organizational Wheel of Fortune as outlined below:


Let me know your thoughts and if I am missing any key questions.

4 thoughts on “Get Your Organizational Wheel of Fortune Spinning

  1. Diane Zuckerman May 6, 2010 / 10:08 am

    This is very good advise and clearly you have great insight into many company CEOs/entrepreneurs whereas I can only speak from my own entrepreneurial experience. However, I would add one more element that would speak to Feature Creep and Focus. Maybe this comes in the Alignment bucket. As a CEO entrepreneur who strives for 110% of myself and the team, I also want the absolute best and ‘right’ product and I have to tell myself (and make everyone else tell me) to STOP the feature creep, keep it simple as you can always improve on the product. In that same vein, entrepreneurs are always thinking of additional products so focus and priority are really important – do one thing well and you can always do more. BTW- I like your visual and will use it (and attribute to you, of course).


  2. chazard May 6, 2010 / 5:17 pm

    Diane, Thanks for the comment. I agree with you 100% that focus is critical, and often hard for talented and creative entrepreneurs. I was thinking it would generally be in the alignment bucket. I also agree with you on feature creep, which to me is part of executing rapidly. Getting things out early and then iterating really fast is an important mantra.


  3. Desmond Pieri May 12, 2010 / 9:57 pm

    Chip, I like point you make in the sixth section; if one does not have a plan, then there needs to immediately be “a plan for a plan.” Often, in coming up with the plan for a plan, one gets a good start down the glide path of solving the problem.


  4. Aneel Bhusri May 31, 2010 / 10:15 pm

    Very good piece that I found valuable as a CEO AND VC:-). Hope all is well with you.


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