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Being Comfortable in the Gray

Most things aren’t black or white. They aren’t either/or. Most things live somewhere in the middle of a continuum. This is why all generalizations are lies.

We like to talk about ideas as if they’re all universals. And there are surely some universal principles that can’t easily be broken, like gravity. But most of the situations we encounter in business and in sales aren’t black or white. They live somewhere in the gray.

The right approach with a customer at the beginning of the sales cycle isn’t always to diagnose their needs (although it is to discover dissatisfaction), nor is it always right to challenge the customer with your new insight. There are different stakeholders within your client companies, and some of them will have ideas about what they want, while others will be more interested in hearing from you. We take our opportunities as they lie.

Much of the time it’s a good idea to diagnose before you present. But sometimes you need to demonstrate your capabilities before you’re even allowed to diagnose. Sometimes the right approach is to occupy gray area.

Your sales process outlines all of the steps you take and the commitments you need to move from target and close. It’s the ideal. It’s supposed to be a universal. But following your sales process can occasionally lead you to a stalled or lost opportunity. Sometimes doing what would customarily work is exactly what costs you an opportunity. Instead of doing what normally works, you from time to time need to do something different to get the outcome you need.

Your clients and prospects are different, they have different needs, and they want you to create value for them in different ways. You have to be comfortable in the gray.

The more you understand about sales, the more you understand about the buying cycle, and the more different processes and methodologies you have available to you, the more comfortable you are living in the gray. Living in the gray gives you more choices. It allows you to be flexible in your approach. You can respond in a way that gets you the outcome you need.

Most of us are uncomfortable in the gray. We’re happier believing there is always one right answer. But there isn’t one right answer. There are a lot of right answers and a lot of ways to get those answers.


What do want to believe is either black or white?

Why is does uncertainty make you so uncomfortable?

Do you always approach your clients as if some certain set of assumptions are true?

What do you do when those assumptions turn out to be wrong?

What could you do to improve your ability to be more flexible in your approach?

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  • Jay Oza

    Good post Anthony.

    You need to do lot of homework before you ever show up for a meeting, since you may have only one shot. Often it is better to postpone it if you are not sure of the outcome of the meeting.

    It is not only you being comfortable in the gray. You really need to find out whether the customer is comfortable in the gray or in black and white. If you and the customer are separated by shades of gray, then you can probably have a productive meeting and a mutually favorable outcome.

    I have gotten burned badly when I was in gray and the customer was not. It was partly my mistake. I did not ask, or did not listen well. The customer never once during our phone and email correspondence mentioned that they had a process problem and that’s why they were interested in our solution. I assumed they had that all figured out otherwise why even look at our application development solution. I was wrong and I talked them out of considering our solution since they were not ready for it.

    Keep up the good work. Enjoy reading your posts and watching your videos with Gerhard.


    • S. Anthony Iannarino

      Thanks, Jay!

  • kel

    wouldnt saying all generalizations are lies be a generalization too?

    • S. Anthony Iannarino

      Absolutely! It’s a meta thing.

  • Marc Zazeela

    Anthony – My experience has taught me that little in life or in business is black or white. We live in shades of gray. There are exceptions to almost every rule.

    Thinking in black and white terms only serves to limit our imaginations and our possibilities.

    Having specific expectations about everything can be very debilitating particularly when the expectations are not met,exactly. We need to think and act with some degree of flexibility. We need to reserve the ability to adapt to situations that are ever changing.


    • S. Anthony Iannarino

      Experience is a great, if brutal, teacher.