These  decisions are not easy by any means but as the statement points to they have the power to determine the outcome of your company.

Make the wrong choice and you might place your startup in such a compromising position it may never recover.  But make the right choice and you have just changed the trajectory of your company, and possibly history.  No doubt these decisions created the Intels, Apples, Facebooks and Googles of the world.

So how do you know when you are siting face to face with a bet the company decision?

First off, you will know by the all too familiar gut feeling that something big is about to happen.  More weight will be on your shoulders and you will hesitate making a snap judgement because you recognize this could be pivotal and you need more information before making the decision.

You will be saying things like “shit… don’t screw this up” and “finally, this is our chance!”

You also will most likely be pressured by outside influences, whether it’s another company wanting to make a deal or market influences putting pressure on your next move.  Bet the company decisions usually take the form of “if X than Y” outcomes, where X is you and Y is another company or market entity.

Lastly, you will sense that things will be different after this decision is made and there will be no going back.  It’s like the “talk” in a relationship…. something will change going forward for better or worse.

Here are some things to think about when making a bet the company decision:

• What do we have to gain by this decision?
• What do we have to lose by this decision?
• What is our current trajectory and how would this decision affect it?
• If we don’t move forward, what happens next?
• Will the brand take a hit, or will it be improved as a result?
• Can we afford NOT to do it?  Can we afford TO DO it?
• Who is affected outside our walls by this decision?

Next, draw out scenarios for all possible outcomes, lay them out  and evaluate each according to your business goals.  Most of the time there is not really one “right” answer you are looking for but more of a “what makes the most sense at this time” answer you can move forward with.

Finally, after deliberation and evaluation you must go with your gut instinct.  Making a “bet the company” decision will surely change the direction of your company but the decision must be made confidently.  Once made, there shouldn’t be any looking back, only forward.  If things don’t work out later on you will be presented with other options to make another decision at that time, but currently your thinking must remain on the present decision at hand.

If it’s not obvious by now I have been presented with a “bet the company” decision and still determining how best to approach it.  I can’t wait to tell… but for the time being I will let you off the hook.   Thanks for letting me think out loud and I hope you are now more confident in your “bet the company” decision.

@jnickhughes