How to Tackle Tough Decisions in Business

“Yes, no, maybe so, black, white, I don’t know.”

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It was all a mumble jumble in her head and she was waiting for me to be her savior. Just tell me what to do!

Let’s call her Rachel. She came to me with a dilemma.

“Should I hire someone to make calls for me and help build my list? I need help now. Is it worth the investment? I’m afraid that my business is too new for this. But my gut is saying that I should just go for it. Am I crazy?”

So first, let me say to Rachel and anyone else who is feeling the same way. NO. YOU ARE NOT CRAZY.

It’s absolutely normal to have times of indecision in your business. It’s normal to feel confused.


The challenge is: How do we get out of our black and white thinking?

How do we move towards seeing creative possibilities?


In this situation Rachel saw only two options. Should she hire? Or not?

And the solution was as simple as this one question:


This one question that I asked led our conversation down a whole new path. Instead of staying stuck in fear mode, she was able to move into the zone of abundant possibility.

Suddenly, without any deep thought or effort she responded, “Well, I could hire someone on a trial basis and see if it’s worthwhile for me.”

That answer seemed too obvious, that I had to wonder why she hadn’t considered that alternative to begin with.

So I asked, “What was holding you back from looking at that as an option until now?”

With this prompt, I coached her through the process of uncovering some of her deeper fears, which included - “How can I hire someone else to do something that I hate to do myself?” and  “If I don’t know what success looks like in this role, how can I determine the results of the trial?”

Oh. These are totally different questions than simply, “Should I hire or not?”

And they have better answers than yes or no.


When asking a yes or no question, you are looking at the picture in grayscale mode.
Ask better questions, and suddenly that image comes to life in vibrant color.


From this place of open possibility, I worked with Rachel to create a custom strategy that took into account her personal situation. With this plan in place, she was able to feel at peace with her decision.

Creative people need creative questions.

Because they deserve creative solutions.