The First Sale

Before anyone else will believe in your perspective, you have to trust that you've earned one.

As much as I don’t like to admit it, I’ve been hard-wired to be a people pleaser from the day I was born. Part of it was that I avoided confrontation, part of it was that I didn’t want to disappoint others, and part of it was that I wanted to be agreeable. Honestly, I thought that was the best way to get ahead in the first ten years or so of working.

If my boss had an idea, I enthusiastically supported it. If a client suggested a product or marketing direction, I rarely challenged it. If someone I respected had an opinion, I assumed it was better than any thoughts scattered in my brain. Looking back, I spent far too much time telling people what I thought they wanted to hear instead of sharing what I truly believed.

To be clear, I wasn’t trying to be dishonest; I simply thought that’s how one climbed the corporate ladder and built a successful career. I believed that if I worked hard, met expectations, avoided conflict, stayed under the radar, and kept everyone “happy,” opportunities for advancement would naturally follow. Yes, there was certainly a bit of truth in that, as being dependable and easy to work with are qualities every professional should possess. The problem was that I confused easy agreement with adding value.

What finally changed internally wasn’t my work ethic, as I’ve always been a very hard worker. What changed was my perspective. After I was “invited to pursue career excellence elsewhere” by HALO Branded Solutions in July of 2008, I did a lot of soul-searching. While no one likes to be fired, especially when a young family and a mortgage are involved, there was a sense of relief on my end because I was truly miserable. During my last two years at HALO, I disagreed with the direction we were taking regarding recruiting salespeople from other distributors. Without getting into specific details which really have no relevance to this blog, I simply kept my mouth shut and went along with the plan - a plan I was put in charge of implementing and leading.

Suffice to say, the plan didn’t go as well as hoped, and the blame was squarely put on my shoulders. I recall sitting in a suite at the old “The Hotel” (Now the W) during PPAI Expo in 2008 and being publicly taken to the woodshed in front of my peers. It was embarrassing, and even then I knew my days were numbered. While I was furious at the semi-public nature of my humiliation, I was just as angry that I knew the plan was flawed but never spoke up to disagree and explain why. Six months later, I was on the job market. This time, however, I approached things differently because I finally realized something.

I had earned my opinion through successes, failures, and lessons along the way, and I had a responsibility to share it respectfully. Not because I was always right, but because I had done the work and gained perspective through experience. Candidly, I think this is where a lot of us get stuck.

We spend years learning from people we admire, and that’s absolutely something we all need to do. We read their books, listen to their podcasts, attend their presentations, and study how they think and approach challenges. That’s part of growth, but sometimes admiration makes us think our own voices matter less by comparison. I’ve been there, and I stayed there for years.

The real irony is that the people I admired the most never built their careers by remaining silent. On the contrary, they became successful because they trusted their own experiences enough to develop a point of view. It took getting fired to realize that the marketplace wasn’t looking for another “yes man,” since there was an abundance of them. What it did need was my experiences, my mistakes, my observations, my learnings, and the way I saw the world. My perspective was valuable, and it shaped how I approached interviews after leaving HALO.

I was honest about my thoughts on sales, marketing, and organizational vision. At times, I even challenged (respectfully and professionally, of course) some of the plans for the roles I was interviewing for. At first, it was very difficult, and I braced for impact during that quiet space as I waited for responses. However, it became quickly apparent that simply sharing candid thoughts - whether the person across the table agreed with them or not - was incredibly refreshing. In short, I got the Vice President of Sales job I craved, and I’ve been confident in being candid and forthright ever since.

Looking back, I’ve come to believe that the first sale every professional needs to make isn’t to a prospect, a client, or an audience; it’s to themselves. It’s the moment you stop asking, “What do people want to hear?” and start sharing what you truly believe. That doesn’t mean becoming obstinate or believing you have all the answers. If anything, the older I get, the more I appreciate how much I still have to learn. Curiosity and humility should never leave us, but neither should conviction.

You can’t expect internal or external clients to buy your perspective until you’ve made that purchase for yourself. It took me losing my job in 2008 - and some self-reflection - to understand and believe that my perspective had value. It wasn’t necessarily finding my voice as much as it was trusting it.

The bottom line is that the first sale every one of us has to make isn’t convincing someone else to believe in us; it’s convincing ourselves that our perspective is valuable enough to help shape the conversation.