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Got A Big Idea? Draft These Two Teammates First

Posted October 29, 2013 by Danielle Bilbruck in On the Ladder

I was riding with a coworker the other day coming back from a meeting with a potential client. We are both very entrepreneurial types, so we enjoy being able to share what kinds of ideas we have festering at any given point in time. As we drove, we talked back and forth about the different business opportunities we were starting in addition to our side jobs and what kind of obstacles we faced.

I have a big support system,” said my coworker. “Almost too supportive sometimes. I have tons of huge ideas and want to accomplish everything. My friends all believe in me so much that any time I come to them with some kind of new project or business or idea, they just tell me over and over again how awesome it all sounds and how successful I will be with it. It’s great to have…don’t get me wrong.  But I think sometimes, I don’t ever get to hear about why my idea might not work or what obstacles might be in my way, so that can be frustrating.”

Funny,” I said, “I’m exactly the opposite. My support system is great, but I purposely want to talk to people who tell me where I might fail. I think that’s my default mode–I’m terrified of failing, so I want to identify all the reasons it won’t work before I even take it on.”

Throughout this conversation, I realized how different these two outlooks were, and yet how necessary they both were to the path of entrepreneurship. So, if you’re thinking about a new and great undertaking, make sure you have these two people on your team in your ear at all times:

  • The Cheerleader. This person is going to be one of the reasons you decide to get an actual start on  your next hare-brained scheme. When you have your random idea and decide to say it out loud, tell this person first. They will ask questions, get excited, tell you what a great idea it is, throw new suggestions on top of it to make it even better, perhaps even point you in the right direction to get started. They will give you the extra push you need to jump off the ledge. You’ll need to keep this person apprised of all new developments–he or she will be the person celebrating your wins the way you may need. When you hit a roadblock and you find yourself wanting to give up or doubting your abilities, this person will tell you how silly it is to do that…that you have a million dollar idea and that they believe in you. They’ll work the pessimism out of you and you’ll go to bed feeling a little more empowered because of your conversation with them.
  • The Thoughtful Cynic. Now, this person doesn’t have to be cynical, but they do need to be pragmatic enough to see holes in your plot and point them out tactfully. You probably shouldn’t tell this person about your idea first–talk to The Cheerleader first, and then as you get started, ask this person to walk through your game plan with you. Their questions will start with, “But have you thought about…” or “What are you going to do if/when…” in an effort to make sure you are prepared. When you’re feeling beaten down, talk to The Cheerleader, get your game face on, and then bring your frustration to The Thoughtful Cynic. They will be your aid in finding solutions and creating road maps to circumvent the obstacles in your way. Hint: this person should be someone that also wants to see you succeed, but maybe isn’t sure it’s in the cards. Do not pick someone for this role that has no desire to reach their own potential and may be frustrated to see other people reach theirs. 

Everyone is familiar with the old cartoons depicting the angel on one shoulder and the devil on another. Typically, it’s supposed to represent the internal struggle surrounding the choice between good for others and good for self (of course, when they conflict.) You can re-frame this concept by keeping a Cheerleader and a Cynic on each shoulder and let there be a conversation with everyone. This is not a fight between the two mentalities, but should instead be a discussion where all of these traits are a better recipe for entrepreneurial success!

About the Author

Danielle Bilbruck

Danielle Bilbruck is an achievement-oriented and energetic professional in the sales world. She is dedicated to increasing efficiency and productivity in order to maximize profitability. Known for her ability to master a position quickly, Danielle has moved up the ladder several times in each company she has worked with. She is a direct and clear communicator, both in written and oral disciplines, and is excited about being a contributor to CGN. She is dedicated to motivating women of all ages around her toward excellence - simply because she expects it from herself.