Getting Beneath the “Why”

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Early on in my book, “Authentic Selling: How to Use the Principles of Sales in Everyday Life,” I talk a little bit about the five “why’s.” Basically, this is where you ask yourself “why” you are motivated to succeed five times in order to get to the real answer. Many people have a surface-level awareness of what they are looking for but have not truly spent the time to ask themselves what they really want in life.

For example, it’s fairly common that someone would tell you that they just want to make a lot of money. But surely there is a reason why having a lot of money would be appealing to someone, because the money in and of itself is not particularly interesting. Does money give you an opportunity to travel the world? Does it give you the financial freedom to pursue a risky endeavor? And regardless of what the answer is, why is that your answer? Only when you peel the proverbial onion and interrogate yourself do you ever find the right answers.

Our “why” is important because it is the bridge to shared values. I talk a lot in my cold-emailing course about the importance of shared values. Shared values are ideas or concepts that we share with others and generally they make us feel more accepted. Given that acceptance is the number one biological human desire, it is important to feel accepted and to make others feel accepted, often through the lens of a shared vision of the world.

We know that shared values are incredibly forceful. Think about every single war that has ever happened throughout human history. It is almost always predicated upon a lack of shared values. When people do not share our values, we (unfortunately) have been compelled to try to do terrible things. I do not condone those things – I am merely pointing out that we have a biological impulse to protect our own ideas, and that is one of the chief reasons why you see so much political disparity and tribalism today. Now more than ever, people are willing to be openly hypocritical about their belief system as long as it keeps them aligned to their “team.”

A ”why” is a great way to establish a shared value with another individual. For example, I do a lot of mentorship in my free time. If I met someone else who did, say, the Big Brother Big Sister program, I would naturally be drawn to that individual over the shared value of mentorship. We would have something instantly to talk about. I would learn about their experience with their little and they would learn about my experience with my little. We would both come out of that interaction feeling welcomed by the other individual and hopefully we would both learn something.

In movies, it is fairly common for a protagonist to be enduring some conflict or some internal heart of darkness. Maybe they have a fear of being unwanted or deserted by a loved one, or maybe they really need to win the big game in order to achieve stardom. Whatever it is, it is generally something that is relatable in a high-level way for the viewer. We have all at some point in our lives shared the fears and anxieties of protagonists that we see in films. That is what pulls us into the narrative: the values we share with the protagonist and our ability to relate to whatever we are watching.

Being relatable, articulating an authentic, clear, and strong “why,” and understanding our shared values with others are all the keys to building fantastic relationships. Unfortunately, in today’s society (and particularly with the proliferation of social media), we find more and more that people are more keen on portraying versions of themselves that are not a reflection of reality. The suicide rate among teenage girls has skyrocketed in recent years as more and more young girls feel a need to compare themselves to superficial and fake versions of other girls. This has a compounding, spiraling effect that only gets worse and worse.

That is why I find it so important to talk up the importance of authenticity. Once people get back to feeling comfortable being themselves, there will be less jealousy, less social climbing, less greed, and yes, less suicide. People will ultimately be happier knowing that they do not have to strain themselves so much around other people. There is something very relieving about knowing that just being yourself is the best ingredient for success with others.

When I mentor individuals looking to break into tech sales, I ask them to uncover their “why” and to be honest about it in jobs interviews, no matter how personal it is. Let me give you a tale of two candidates, and you choose for yourself which one seems more attractive to you for an entry-level sales role. One of the following individuals is fictitious and the other is a real person that I mentored.

The first candidate is a young woman named Emily. Emily went to a pretty good liberal arts school and is interested in getting into tech sales because her father works at a prominent Venture Capital firm. She grew up listening to him talking about tech startups. She has identified a company with a strong company culture and she thinks that it is a good place for her to get a growth opportunity where she will get promoted in 12-24 months into a higher-earning sales role. She tells the recruiter that she really values the company’s “work hard, play hard” mentality as it reminds her of her father.

The second candidate is a young woman named Leslie. Leslie is a first-generation college student who is the daughter of Chinese immigrants. Leslie’s parents worked multiple jobs growing up to support the family, and Leslie herself had to delay her college education to work in order to support her family. Leslie did some introspection and realized that she really lacked autonomy growing up since her family had to come first, so she made a lot of personal sacrifices. She tells the recruiter not so much about the company she is applying for, but how she thinks it is a place where she has an opportunity to create financial independence for herself that would ultimately give her the autonomy she never had as a child.

I think most people would view the first candidate as a more “traditional” candidate who best fits the mold of working in a tech startup, but if I were the hiring manager, I would not hesitate to take the second candidate, who was a real former mentee of mine. Why is that? Because she actually knows what she wants, and based on her background, I really believe her when she tells me she will work hard. I believe her because she has thought things through. She has a plan to get from Point A to Point B. The first candidate just told me all the same fluff that any other candidate would tell me – that the company culture seems great, she can make a lot of money, maybe the office has cool snacks, or her father coaxed her into the role. None of these are really good reasons because they have not gone to that deeper layer of understanding.

Let’s go back to poor Emily for a moment and figure out what would make her “why” a bit more compelling. Let’s say hypothetically that sadly Emily’s father is no longer with us. Emily might tell us that her father always wished that Emily would be a pioneer as a female leader in tech and to carry on his legacy. Now Emily’s “why” is that she wants to make her father proud of her and fulfill that destiny.

While I am not trying to kill off innocent parents on purpose, this “why” is clearly a lot more powerful than the first one. And to be sure, I have had mentees who have unfortunately lost loved ones and who, in fact, have gone into interviews and talked about what sense of purpose that gave them. That is good and I encourage it, so long as the person is able and willing to talk about their trauma. I do not encourage this so people feel bad for anyone; I encourage it because it is the raw, unfiltered truth and I want employers to know what they are really getting with the person they are talking to.

What is the downside to being honest? The answer is that there isn’t one. Let’s say hypothetically that Emily tells this personal story about her father and wanting to follow in his footsteps. And let’s say that the hypothetical company she is interviewing with is really turned off by this rather personal story, and they end up not hiring her. Is this a bad thing for Emily?

The answer is “no.” In fact, I would argue that it is a very good thing. When you are honest and authentic about your motivations, you weed out the people who are not truly a good fit for you in your life. In my estimation, Emily dodges a bullet in this hypothetical scenario, because now she is not working for a company that will hold grudges or cast judgment upon others based on the events of their personal lives.

I have told every company I have ever interviewed for that I have a work ethic and a motor unlike any they have ever seen before. Naturally, a lot of people ask me why that is. I give them the truth, albeit in a funny way: I had a stereotypical Jewish mother growing up who pushed me really hard to succeed. However, she always emphasized effort over results. I was never yelled at for getting a B+. I was yelled at if I mailed it in and got an A, though. That mentality stuck with me through life. But I bet you that most interviews do not have stories about paranoid Jewish mothers. This makes me memorable, but it’s also the honest truth. And it’s such an outlandish story to tell that it feels even more believable to the other person.

Trying to navigate today’s information environment is incredibly difficult. I have a hard time right now in my personal life seeing something going on in the world and being able to distill fact from fiction. More than ever, we have ways to fake information both about ourselves and about the world. Technology has reached a point where we can create lifelike, animated videos of other people doing things that they are not actually doing. All this to say, we are losing our authenticity, and the repercussions will be massive if we do not all do our part to see the beauty of being ourselves.

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