Guiding Principle #11: Make sure you have a plan B and can live with ‘worst case’

This is a relatively new one for me and was added after I got fired from Staples.

This is a relatively new one for me and was added after I got fired from Staples. I had been working for Thrive for 7 years with my head down the entire time not even thinking about the potential of what might happen to me after we sold to Staples. I was the VP of Sales who helped get the company to where it was. I led the company culture and if you cut me I bled blue (our colors). I was smart and gosh darn it people like me. I didn’t need a plan B right? Wrong.

Thankfully everything worked out and getting fired from Staples was probably the best thing that could have ever happened to me in my career. But it got me to wake up a bit and realize I couldn’t continue to go all in without having a plan B or at the very least without knowing the worst case scenario and being ok with it. This is relevant across the board to the decisions we make in our career, specific deals and negotiations we’re working on with clients, investments we make with our money, and everything else.

I now force myself to think of two things when making any major investment of my time or money: 1) what’s the worst case scenario if this doesn’t work out and am I ok with it and 2) what’s my plan B if it doesn’t work out. For example, when I’m working with a prospective client and dealing with someone below the power lineand they won’t give me access to the decision makers I then ask myself a few questions: What’s my plan A to gain access to power? Potential answer – develop a business justification and ask my contact to facilitate an intro and including them on the conversation with the executive. Next questions – what if they say no, am I ok with that? Probably not so what’s my plan B? Have my boss or myself reach out to the executive referencing something about them or their role that you need insight on and only they can provide. What if my contact finds out and gets pissed off? Am I ok with that? In my opinion, if I’ve done my job throughout the Sales process, learned about their true needs and know my product can make a difference but my main contact is preventing me from accessing the additional info I need then yes, I’m ok with pissing them off and potentially losing the deal. I’d rather lose a deal for the right reasons than win a deal for the wrong ones. That’s my approach and what I’m ok with. You might have a different approach and be ok with different results. Regardless, we need to ask ourselves those questions to keep ourselves in check. Good luck and happy selling.

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