Learning to be a CEO

There have been a couple of good posts recently about startup CEO’s serving on the boards of other startups.  Brad Feld wrote one and Mark Suster continued the thought here.

The logic is that you gain an independent and important perspective on many of the key activities you do yourself by serving on another board.  In particular Brad lists these advantages:

  • “You’ll extend your network. 
  • You’ll view a company from a different vantage point. 
  • You’ll be on the other side of the financing discussions.
  • You’ll understand “fiduciary responsibility” more deeply. 
  • You’ll have a peer relationship with another CEO that you have a vested interest in that crosses over to a board – CEO relationship. 
  • You’ll get exposed to new management styles. You’ll experience different conflicts that you won’t have the same type of pressure from.”

Of course the trick is balancing the additional time commitment with the CEO’s own responsibilities.

I have been lucky at SugarSync to have had a CEO/Entrepreneur on my board.  When I first got to SugarSync, Bud Colligan (cofounder of Macromedia) was a board member.  When he left we recruited Paula Long (cofounder of EqualLogic and now CEO of DataGravity) to the board.  They both have brought a great deal of sensitivity to both the practical and strategic as well as organizational issues and have given me great coaching.  They both had financial “skin in the game” but could take a broad strategic view.

I have not yet served on another startup company board but would look forward to that opportunity for the reasons above.  Because of their importance I have sought out other ways to get some of these experiences.  While it is natural to have peer colleagues at an executive level while working in a company the CEO has no natural peers in the company – you need to seek them out outside.  The first thing I did on this front, based on the advice of an experienced CEO friend and non-profit board colleague was to join an organization called Vistage.  I believe there are a few similar organizations that serve this purpose – I can only share my experience with this one.

Although there are other educational resources and coaching as part of Vistage, I find the core value comes in the monthly meetings with the CEO group.  There are about 15 members of the group – existing members make certain that when members join there is no potential business competition or other conflicts within the group.  The setting is confidential and discussions are moderated by the chairperson.  Our group is about half tech businesses and half from a range of industries from services to heavy equipment.  Over time the members learn enough about each other’s business to have a basic perspective.  After about an hour where each member gives an update there are about 2-3 hours where the group can process a handful of issues identified during the update.

It is incredibly helpful to have a dozen peers with no personal agenda such as their own role or financial investment help you process an issue, alert you to blind spots and share their diverse experiences and wisdom.  They are not expert in your business but have a wealth of experience managing boards, investors, M&A transactions, fundraising, dealing with lenders, personnel issues – many of the common challenges CEO’s face.  Of course the learning goes both ways – when listening to the discussion about another person’s issues – you learn about yourself and how you might deal with your own future challenges.

I’ve been fortunate to have a couple of other venues to network and share experiences with other CEO’s.  Two of my investors, Sigma Partners and DFJ both host annual CEO summits.  I’ve also formed an informal women tech CEO group – we have dinner every couple of months.  These groups don’t have the frequency or consistency of Vistage but the larger network is very valuable.

Developing my skills as a CEO has been a journey.  There’s no “manager” to train/teach me.  I’ve been learning from my board, my CEO peers, “expert” opinions I read such as blogs and mostly from my team.  I thank everyone who’s been patient with me and look forward to continuing to learn.