Can a small business learn from the C-Suite of Microsoft?  Hear what Bob Herbold, the former Chief Operating Officer of Microsoft Corporation and the author of “What’s Holding You Back? Ten Bold Steps that Define Gutsy Leaders” told me regarding lessons that small business owners can learn from his experience.


CR: Why is it so difficult for solopreneurs to make the leap and hire employees?

BH: Because they are taking a risk.  It is only natural that they should feel apprehensive.  On the other hand, there is a time when you have to face reality and decide based on what you believe.  You do all the analysis and collect all the data you can, and then take stock and decide.  The faint hearted will procrastinate at this point, and undermine their efforts.  If you can’t make those kind of decisions, maybe entrepreneurship is not your cup of tea.

CR: How can a small business staff up for success to take their business to the next level?

BH: The answer is “very carefully”.  You should press yourself hard regarding exactly what the staffing will do and why it is needed.  Most importantly, when you hire, be very careful to get very strong performers.  The due diligence process in vetting candidates is critical. 

CR: What about those that are entrepreneurial and don’t want to take on financial risk, how can they engage leadership within an organization and persuade them to take on entrepreneurial projects (so that the individual doesn’t have to take the financial risk but can still exercise his entrepreneurial spirit)?

BH: It is all about selling your ideas.  You need to do solid analysis, and collect as much relevant data as possible, and then put it together in a persuasive way.  

CR: How can small businesses extend leadership principles to their interactions with outsourced service providers?

BH: Outsourced providers / vendors need to have very specific rules of engagement and performance criteria.  They need to be evaluated regularly, just like your employees.   Being sloppy can really hurt you, just like not being clear with your employees about the vision, strategies, and measures causes floundering.

CR: What are the other top takeaways and lessons a small business owner can glean from What’s Holding You Back?

BH: The first principle in the book is to confront reality and develop a demanding game plan.  That is even more important for a small business because the room for error is less.  You need to be constantly looking at your products, the behavior of your customers and the trends of the market and then develop a game plan to make the most of your situation.  Too many small businesses launch a set of products and then assume they are done and that they just need to execute each day after that.  It is not that easy.  The world is always changing, and the successful companies are the ones driving the change, taking advantage of new technologies and new customer trends. 


Bob Herbold is the former Chief Operating Officer of Microsoft Corporation and the author of three books on leadership.  His latest, “What’s Holding You Back? Ten Bold Steps that Define Gutsy Leaders” was released February, 2011 by Wiley/Jossey-Bass.  Bob’s blog on leadership can be found at