Who is in YOUR cabinet?

By Debbie Gordon

Selecting your Cabinet as an Entrepreneur

With all of the activity surrounding the President-Elect’s cabinet selections, it occurred to me that so many entrepreneurs don’t always have the luxury of hand selecting individuals to advise and lead specific areas of our businesses.  In many entrepreneur owned companies, often people assume a role or roles simply because it is where they have spent their time and energy as the company matures.  A person may have been around since the inception of the business, and they do what they do because, well, that’s what they do!  Additionally, one person may wear many hats simply because of budget constraints, necessity, or again, well, that’s just what they do.

Remember back when you started your business.  Oh how lovely it would have been to have the resources and foresight to be able to handpick a group of individuals to be the leaders of each of your critical departments.  Unless you raised significant capital and had a network of people that were ready to drop everything and come to work with you, chances are you started small.  Maybe you enlisted a friend, maybe a partner or spouse, or perhaps you hired someone to simply help out that has since grown into a much bigger role.  

Now consider a very different situation as it pertains to a Presidential Cabinet.  The President-Elect was in essence “hired” to be the CEO of the country and has to select people to lead and advise various departments in which he has little to no experience (NOTE: fact, not political statement).   Think about this in relation to your business. It’s certainly a lot easier to hire people to fill certain leadership roles when you personally have done that job or at least been involved in the decision-making around that subject or “department”.  You have the ability to think critically about what has to get done and how it gets done.  But when you don’t know what you don’t know, it is a lot harder to know if this person is indeed the right person to lead.

There are some things that you can ascertain no matter how your “cabinet” came to be, or whether you are at a point in your business where you can deliberately handpick people.  Here are some simple things to consider:

1.       Do they know (and share) your purpose?  Alignment of values can make or break a business.    Think about this as it pertains to the Presidential Cabinet.  The President-Elect, when identifying potential people for his cabinet, needs to be sure that these people share his values.  In government, those values are very apparent, as we all know from the months and months of campaigning.  But in a business, values are not always so apparent.  Yes, your company may have a values declaration written on the wall or somewhere on your website, but how do those values actually manifest themselves into decision making?  Besides just being aware of your values, does your prospect actually share those values and are they willing and able to make decisions that align with those values?  

2.       Are they your clone?   Have you said something like, “I could totally hang out and have a beer with that person”.  Do they act like you or have similar traits to you?  Do you feel comfortable with them because they are predicable because it is how you would do something?  Nothing will inhibit innovation more than hiring someone who is going to do things just the way you would do them.   As a fast-moving, hard-charging entrepreneur, when you consider a candidate for a leadership role perhaps you may think “they are not decisive enough” or “they are too reserved”.  They just don’t seem like a good fit, right?  I have been in situations where someone’s personality was so different than mine, that it actually made me uncomfortable to interact with them.  20 years ago, there is no way I would have hired such a person.   But when I look deeper at what those things actually represent, that is the foundation for a perfect fit.   We need someone to balance us and bring different perspectives to our ways of thinking.  We actually need someone to think versus simply act, which we entrepreneurs often do all too impulsively.  So that person who you may think is “too reserved” or “not decisive enough” may actually be processing situations in a much more methodical manner versus just going with what comes to their mind impulsively.  Look for people who don’t think like you, embrace them, and learn each other’s styles. 

3.       Are they willing (and permitted) to challenge you?  As an entrepreneur, you likely exhibit an air of confidence when talking.  People in your organization may assume that what you say is already well thought out, and well, a final decision.  For example, if you say “We should do x”, others may hear it as a directive.  But in fact, as a continuously improving leader, what you are actually saying is “This idea literally popped into my mind 3 seconds ago when someone mentioned XYZ and we should think about exploring that so what do you all think?”  Right?   When I ask key executives if they think their entrepreneur/CEO would say that they desire being challenged by their key executives, most of those key executives answer “no” or “not really” or “I don’t believe so”.  Even people who hold high level, leadership roles in organizations do not always challenge the CEO/entrepreneur enough.  That doesn’t mean they are a “yes man” or “yes woman”, it simply means they haven’t been specifically told by the entrepreneur that they actually want to be challenged more.  Once that alignment happens and the key executive has been given permission to challenge, a new level of leadership occurs and in turn, an unexpected (and counter intuitive) level of comfort will be felt by the entrepreneur.

So, in this pre-inauguration season, as our President-Elect continues to select his cabinet members, think about who is in your cabinet.  Having people in your cabinet who share your values, take a different approach to decision making and problem solving, and have been told that you as a leader welcome being challenged, together create a solid foundation for a high performing business.

Up Next: Cleaning out your cabinet.