Is Empathy Helping or Hurting Your Career?

One of the age-old questions is whether or not Good Guys (and Girls) Win. The answer is — it depends, but not in the way that you may think.

The feeling — and for lack of a better word- strategy of empathy has been proven to be quite effective and quite destructive on a consistent basis depending on its method and context of deployment.

In his latest book, Give and Take, Adam Grant outlined an interesting finding — Givers were both the best and worst performers in corporate America.

How could this be true?

This distinction comes from the fact that high-performing givers are very conscious about who they gave to, and steered clear of takers, which it so happens, take a disproportionate amount of value from the economy.

Takers, on the other hand, are rewarded in the short term (see: benefit of the doubt) and are punished in the long-term by the market of Givers, Matchers, and other Takers on quite a consistent and somewhat brutal but not undeserved basis (firing / pigeonholing / etc.).

What about Silicon Valley?

Silicon Valley, like any epicenter of highly qualified and talented individuals (like Wall Street / Hollywood / etc.) has seen it’s share of takers (unnamed) and givers (Reid Hoffman / Ron Conway / Naval Ravikant, etc.) over the years. Overall — it seems to work quite well for founders and investors who deal with early stage startups. Paul Graham has a great essay on the economics behind this — Why It’s Safe for Founders to Be Nice.

After being involved in tech for 13+ years (and living in San Francisco for 8 of those years), I’ve seen a consistent and predictable way in which way empathy (or the lack of it) plays out in both the short and long term.

Empathy as an Investor

Nowhere else is empathy a two-edged sword then when it comes to being a VC. Empathy is the way that top VC’s get into the 1 out of 100 deals that “matter”, and conversely it is the very thing that makes it difficult to reject the other 99 teams. Empathetic people care, beyond the financials, and the process of building and rejecting relationships can take its toll on someone with even the smallest amount of empathy.

Empathy also has a way of rearing its ugliness when that empathy leads to believing the hype or giving the benefit of the doubt to teams and companies that do not deserve it or are psychopathic in nature (by some accounts, 25% of Silicon Valley).

Empathy in Negotiation

Perhaps one of the most underrated area of empathy is in the area of negotiation. Contrary to popular opinion, in an information economy, most top negotiators excel at value creation vs. value taking (a skill that is increasingly becoming commoditized with more data available every day).

Empathy Can’t Be Taught (Easily)

Perhaps the best way to look at empathy is that it is just another tool in the toolkit. Empathy, like many skills, is learned over time (particularly in childhood) and creates a distinct neural pathway in the brain- the more it is practiced.

Like other skills, empathy can be used both in a productive and unproductive manner.

Empathy as a Gift to Empathetic People

What I’ve concluded, is that as a business strategy, it is unsafe to provide the gift of empathy to every individual. When I say this, I do not mean that you shouldn’t save a drowning child or feed a person who is starving.

What I mean is that, contrary to what Adam Grant says, I have found that the average person in the corporate environment (especially at the highest level) is a taker, or a mild matcher at best. In other words, the average person will keep on taking without really giving much thought to giving.

If you doubt this in any way, open your email. I am inundated daily with LinkedIn or Email messages from people I have not talked to or seen in almost a decade asking me for fairly large favors w/no reciprocity. In fact, by my own estimates, less than 5% of these messages have any reciprocal nature to them.

Although I agree with Adam that there are some givers are at the top of organizations, I do not believe that this is a requisite or even positively correlated with achieving high levels of success in business. I would argue, historically, that giving and empathy has a negative correlation with career success, not because it is not a useful skillset, but because it is so often deployed in the wrong way or given to the wrong person.

However — Empathy Can be a Great Super-Power

There is, however, a silver lining to both giving and having empathy — in that it can become a significant differentiator and incredible Super-Power.

This is especially the case if you have a very high filter for people who lack empathy — a skillset that I lack and therefore surround myself with.

Being a Giver can create a very high level of relationship and opportunity in the business world. There have been two examples of this in my life where Giving and having empathy has made my career.

The first example, is quite interesting, in that it is illustrative of the sheer number of takers their are in the market.

While in business school, I connected with an “up and coming” entrepreneur that had already started a billion dollar company and was well on his way to his second billion dollar company.

Rather then reach out and ask him for a favor, I built a deeper connection with him when I asked him how I be helpful to his business in hope of building a relationship.

As a 24 year old kid, he said to me something that shocked me at the time— “You are the first person that has ever reached out to me asking to help.”

Seven years later, this man is my main mentor and a close friend. On top of the personal connection — he was an early investor in my last startup RoomHunt and served as my most trusted confidant as we were going through the company’s acquisition. He also happens to be (not coincidentally) the very person who made it possible for me to make my very first venture investment — which I wrote about earlier (How We Raised $100MM+ for a Stealth Startup) .

The second example is a bit more corporate as it was in the context of one of the largest financing that I have ever been involved in, when my firm (GTP) raised $200MM for an ecommerce company in India. Although I am still under NDA, I can safely share that the sheer complexity and high stakes of the negotiation made the existence of my empathy (and ethics) were very helpful in bringing the deal across the finish line.

On a Personal Level

Though it has worked out quite well for me on the business side — it has certainly led to my share of disappointment and broken hearts in my personal life.

As a true entrepreneur, I have sought to give the gift of empathy to those who could use it vs. those who deserve it the most, a mistake I have paid over and over again.

It should be noted that I have not had a single instance when my empathy or love for an unempathetic person has significantly changed the other person in any meaningful way.

It’s for this reason, that I have decided in the past year to only provide empathy to those who are empathetic in nature. “Love shouldn’t hurt” as they say.

As this post, and my writing, my life is still a work in progress — so I shall keep you posted.

If you like what you read be sure to hold down👏🏻 (clap) below, your empathy is appreciated and noted 🤣 .