Hiring an Entrepreneurial Leader

I recently had a client ask me for suggestions on what type of questions to ask of their Executive Director candidates that would help them find someone who would be able to effectively lead their social enterprise efforts. I realized many organizations are in similar situations - going through leadership transitions and wanting to find someone that can lead the organization in a way that supports an entrepreneurial culture. Here are a few tips on questions to ask and answers to look for:

1) Ask what their entrepreneurial experience has been - have they started a business? Have they started major initiatives within a larger organization? Find out how these endeavors ended up. Listen for the mistakes they made and what they learned form those. If they try to sugar coat their entrepreneurial experiences, they may not really get that one of the most important aspects of being an entrepreneur is making mistakes, making course corrections and moving on.

2) Ask how they have or plan to integrate entrepreneurial thinking and support into the organization. Look for indications that they'll set up simple processes for allowing people's ideas to be surfaced and quickly vetted to determine if they should receive more organizational resources to study further. Try to get a sense of how they'll provide incentives for people to come up with innovative solutions to everyday problems.

3) Ask what their expectations are for earned income generation in the organization. If they are wildly optimistic and think the organization can be totally self-sufficient in a short period of time, they probably don't have a realistic sense of what it really means to run a social enterprise. On the other hand, if they are so down on earned income they don't want to have anything to do with it, they may have had a negative entrepreneurial experience they still haven't recovered from. In short, they should be looking to determine the most realistic, sustainable revenue mix (e.g. grants, individual donations, earned income) for that particular organization and develop a plan around how to achieve it.

Lastly, I think it's always a good thing to come across someone who knows what they don't know. If they know they have limitations around particular aspects of being an entrepreneur that's great - you're a step ahead in figuring out what gaps need to be filled through training, other staff or consultants. Best wishes on a successful hire! And, for all of you entrepreneurial job searchers out there - just be honest and be yourself. Really.