Leveling Up In Your Sales Career

A mentee of mine called me the other day with a predicament. He was doing really well over the last year in his new sales role and really felt that he was turning the corner in his career, but he was starting to hit a snag with nerves as more and more senior managers and leaders were joining his calls. He had recently been promoted to a new team where he was speaking to larger clients, and the “flow state” he had when he was running meetings solo was escaping him. In addition to having higher stakes with more senior leaders at bigger companies, he also felt like he had many eyeballs on him from his own company, and this was hindering his ability to run his deals like his authentic self. He could literally feel the expectations on the call.

What struck me during our conversation was that he had felt that he might solve this challenge by engaging with a language coach. I have always admired him for the initiative he takes. I think learning about how to speak and using words that truly matter is a tremendous skill, and something I would also like to work on. Deep down, however, I felt that whatever challenges he was feeling were mental and could be dealt with through simple shifts in mindset.

Conventional wisdom tells you to imagine your audience naked to let go of your nerves. It’s certainly one strategy, though I can’t say I have been very successful at trying it. I offered a few tips of my own.

The first thing I recommended was to read the book “Letting Go.” This was one of the first things I did a little over a year ago after a tough breakup with the CEO of my last startup. I decided to explore consciousness and this book completely changed my life. Through reading it, I began to understand that thoughts and feelings are not real. The real “you” is the one observing yourself having the thoughts and feelings. If you can recognize that – and thereafter recognize what in your past experience is causing you to have these thoughts or feelings – you are much more able to just let them go. By adopting this philosophy, I have been able in very difficult times to let go of conflict that would otherwise cause me stress.

Applying this to my mentee, I asked him a simple question: what is the absolute worst thing that would happen if he started bombing these calls? First, he would get a lot of coaching and encouragement. He would seek out outside help. It was no different than any other time in his life he had a setback, and he always seemed to figure out a way forward. But I played this out further: what if this was the one time he did not figure it out? What if he just kept bombing and bombing? What would happen?

The answer is maybe he would get moved back to his old team. Or even worse, maybe he would just get fired. Then what? Would life stop moving? The reality is, he had demonstrated over the last two years in our work together that he was going to have absolutely no problem landing on his feet. Not only that, he had built such strong champions in his network between me and many other advisors and friends who almost certainly were going to actively help him out. Realizing this context, I noticed a shift in him: even the absolute worst thing was not the end of the world.

Therein lies the real rub with all of these professional situations and sales conversations: we place disproportionate emphasis on everything. Realistically, there was life before whatever conversation you are having and there is going to be life after it. That’s true of all conflict. If you are able to recognize that you are literally just a speck of dust in the universe, you can let go and care less. Caring less and detaching from the outcome removes the gravity of having a few extra eyeballs on the call. After all, who cares if you fail? You’re a speck of dust anyway.

The other thing I encouraged him to do was to have a shift in mindset. On one hand, when entering what feels like an “important” situation you can be nervous. On the other hand, you can be excited. In the case of my mentee, he has been doing such amazing work that he got promoted in a very short period of time. Through my lens, he should be excited to show his new leaders what he is made of. And frankly, even if he blows it on the calls, he should be excited about the feedback he is going to get that is going to make him better. That brings us to the growth mindset.

We are so obsessed with winning as a culture that we often lose sight of the simple fact that you need to lose over and over again to get good at anything. An old colleague of mine used to use the expression “calloused mind.” He thought you needed to callous your mind with adversity in order to get stronger. If you go about life with an understanding that there actually is no losing, there is nothing to be nervous about. If you win, you win. If you lose, you gain the critical feedback and knowledge that you need to win. Either way, you are winning.