Entrepreneur Muscle-Building

Entrepreneur-turned-VC, Mark Suster, recently posted an article on his blog, Both Sides of the Table, highlighting what he considers to be the essential qualities of entrepreneurship.  At the heart of his post is a very, very simple philosophy: entrepreneurs just do it.

For some people, this is easy.  Moving ahead, pulling the trigger, motivating people into action, moving at light speed — categorize it however you like, but how comfortable you are with this type of thing often starts out as being a very basic part of your personality.

For other people, however, this is much, much harder.  Whether it’s a fear of being wrong, a need to collect input from numerous different sources, or just a methodical decision-making process, some people are very uncomfortable churning through a couple of dozen decisions per day, and tap-dancing their way around obstacles in real time.

So what do you do if you want to own your own business, but rapid-fire decision-making did not come baked into your DNA?  Here are a few tips and tricks I use when working with new entrepreneurs, to start getting them comfortable with what the role demands of them:

Define and document your process
Everyone has a different process for making decisions.  But for most of us, it’s intuitive and has evolved over time.  We often don’t think about it, or even recognize all the steps.  The benefit of sitting down and writing it out (I often either recommend a flow chart or a bullet list) is that it helps us be aware of places we are likely to get stuck or where we become repetitious.

Focus on what your process actually is, not what you’d like it to be.  (You can work on changing it later.  Start off by understanding it.)

Even more valuable, however, is having this on hand when it comes to working with others.  Because if you can show your partner or your staff what your decision-making process looks like, it helps manage their expectations.  It also identifies at what point you need input, and at what point they need to be prepared for action.  It sounds amazingly simple, but it’s invariably far more powerful an exercise to go through than most people expect.

Once you’ve documented your process, the next step is to identify the part of the process with which you are least comfortable (generally speaking), and at which point in the process you most frequently find yourself getting stuck.  Sometimes it’s the same step, sometimes it’s not.  But again, breaking it down and really thinking about something that you do instinctively is critical if you are going to start changing your habits at all.

Partner up
For as nice an idea as it is that we are all always going to keep our promises to ourselves, the truth is, our promises to ourselves are often the first ones that we break.  So for most of us, accountability is most successful if it is to someone else entirely.  So find a parter, coach or collaborator.  It’s like having a workout partner for the gym: sometimes knowing that someone else is expecting you is the only way you’re going to make it.

Whether you go to an organization like SCORE for a mentor, or you hire a business coach, or even a part-time project manager to help you with planning and organization, sometimes the best thing you can do for your progress is to put yourself — and your money — on the line.  Putting some skin in the game is almost always good for the end results.

Break it into bite-sized pieces
Some projects and efforts are just huge, and until you dice and slice them, they are simply too overwhelming to make any real progress.  So break it down.  Again, this may require some outside help, but once you have your efforts broken down into logical chunks, it’s much easier to define tactical next steps for each piece, and then to show — and see — progress.

The best rule of thumb is to keep every piece to 8 hours (or a day’s) worth of work or less.  Don’t let anything get too big, and it’ll be much easier to stay focused.  If you’ve parsed out your steps into day-by-day sized pieces, then you will also often find that the difficult decisions that seem huge in their original state are also broken down into more readily managable sizes, making them easier and faster to resolve.

Not everyone is a natural born entrepreneur.  But there are tons of people who are willing to do the work to make the transition, including being ready to push themselves out of their comfort zone to get there.  There is nothing wrong with wanting to analyze details in more depth; just be aware of the fact that being wrong is ok, and that there are very few decisions that can’t be reversed if they really need to be later.

Often times it’s not possible to know for sure that an answer is right until you’ve explored the wrong one a bit.  But if it doesn’t come naturally to you, find some help.  There are lots of people who have been there and figured it out already.  Take advantage of their expertise and get their assistance building a system to help you make the transition you need.

Alora Chistiakoff is an entrepreneur, content strategist and project manager who has been developing online business and technology for startups for more than a decade.  She co-owns The Indigo Heron Group, Inc., a content strategy firm in Austin, Texas.