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Sales is winning steak knife sets; consulting wins customers.

July 22, 2022

I have been in sales for the majority of my career. When I tell personal friends this, they often look at me in shock. You are not super outgoing/bubbly/extroverted/etc. No, I am not. I was a painfully shy child who still prefers a quiet night with 1 or 2 friends over a crowded party. But I have made a career out of consultative sales.


Mostly because sales in my experience is nothing like what people think it is from afar. Enterprise sales involves selling to a buyer that often knows more about their business than I ever will. It involves humbly listening and learning. I will never win business by providing an excellent pitch or a very smooth Sandler sales trick.

In fact, I credit much of my success to my authentic awkwardness which translates into being trustworthy. I do not always have an amazing comeback to an objection. Many times, I may agree with the objection.

My “secret” if you can even call it that, is a genuine interest and curiosity on finding a solution. To figure out how to make a situation better. I love to share new ideas, to empathize with someone’s struggle.

I enjoy the very real experience of relating. Much of my sales process involves bringing together multiple stakeholders to ensure each party understands how they will benefit and the potential changes that they will need to agree to so we can move forward. Working with lots of different types of people is a daily masterclass in learning to relate with others.

I often find I develop the deepest professional relationships when I get a sincere No. Instead of shutting it down, I recognize this as an opportunity to learn more about the Why. Good opportunities do not always have the ideal timing. But ultimately, most people want their situation to improve. And if I know I have a solution, it’s my job to help the buyer overcome those objections.

I love working in the intersection between healthcare, insurance and technology because it is an essential service we all will use, and it is a space that has so much room for improvement. Even so, it is an industry that is incredibly fragmented and involves numerous stakeholders with various priorities. I cannot change these priorities. My job is to figure out how these different priorities can exist within my solution.

In working with various organizations, I have found many different styles of sales leadership. I often find Founders and CEOs enamored with the initial meeting. The praise of the initial review. The press release, the final ringing of the bell. These parts are fun. But lots of people can be great at one meeting. Buyers are wise to that. The real work is to get past the compliments and figure out the real concerns. What are the hesitations they are afraid to mention? Every potential buyer has their own baggage, their own back story. They had a recent purchase that was deemed a “success” and are therefore extra confident and want to use this opportunity to further make a name for themselves in their organization. Or, they had a purchase that didn't go as expected and they are now hesitant to use their social capital on another initiative.

More often than not, whether a sale is successful has more to do with things completely outside of my control. My goal is not to change the situation. It’s definitely not my goal to try and control the situation. My only goal is to understand the situation. My goal is to develop trust. Get the real story. This does not come out in an amazing demo.

Once I fully absorbed the understanding that my success was in no way tied to my likability, I became a better consultant. In enterprise sales, you are asking people to do extra work. You are not always going to be everyone's favorite person. You may be the person they look back on with respect and appreciation, but you will not always be loved during the process.

What's funny is that most people think of sales people as charismatic and engaging, like a politician. In reality, sales is 80% the behind the scenes project management that involves methodically moving through a buying process. At times nudging a bit more than they would like. It involves listening and addressing concerns and objections, not focusing on whatever the product is I’m trying to sell. Sales is more about coaching your buyer in a way that resonates with their priorities. Helping support them as they navigate the internal political process of working through procurement, contracting, security reviews, etc.

Consultative enterprise sales is complex. It leans into all the different parts of my brain. It has helped me be more patient and understanding in my personal life. But at the end of every week (because we all have those really tough days) I am grateful I stumbled into the industry and this career. I wish someone had told me, sales is not about you. It’s about making other people feel seen, heard, and appreciated.

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