Leadership Lessons From the Tech Trenches

From December 2013 to March 2014, I led our largest commercial partnership at Palantir, an enterprise software and data analysis company. There were lots of week-to-week learnings, growing pains and, fortunately, successes. But it is only in the last month, after a break from the international travel, executive meetings, contract negotiations and varied personalities of the rapidly growing team that I’ve been able to articulate the most important lesson of all: leadership is really, really hard.

Here are five takeaways that I am just now able to appreciate:Wharton leadership lessons learned in the tech business

At some point, your powers will fail you.

It’s common in feedback sessions to discuss one’s strengths and weaknesses. We celebrate the things we’re good at and devise contingency plans to manage the things we’re bad at. But guess what? At some point, your strengths will fail you. It will happen unexpectedly. Your team will be bewildered and you will want to crawl into a hole and never come out. And that’s OK for a few days. But then you have to figure out how to bounce back, and it’s difficult because you feel like your team expects you to do everything well, all the time. If you focus on the bright side, though, which is that you have actually strengthened yourself by adding to your arsenal of experiences, it can be pretty uplifting.

Here’s a tangible example: I have above-average emotional quotient (EQ) and am able to form strong, trust-based relationships with clients. However, I recently endured a face-palm kind of experience where I completely misread a project sponsor. I thought he was forward leaning, visionary and on the same page as us. As it turns out, he wasn’t. Though we eventually figured out how to turn around the situation, the experience certainly left some bruises on my self-esteem. I’ve come to realize, though, that this experience provided me with more rigorous methods to evaluate clients and the ability to better articulate how I do this, which I’ve been able to pass along to colleagues. It’s pretty awesome that an individual moment of weakness can lead to a communal moment of strength.

When it comes to your boss, a healthy relationship is also a complicated one.

When you’re at the bottom of the totem pole, your relationship with your boss is pretty straightforward. You may strongly like or dislike him personally, but the way you interact from a deliverables perspective is simple. You are given tasks and your goal is to complete them effectively and efficiently. As you take on leadership positions, the lines start blurring. At Palantir, I’ve always greatly respected my boss, but I’ve also disagreed vehemently with him, been enraged by him, felt like he was asking me to do something I couldn’t do—or that he “just didn’t get me.” Stepping back, I’ve realized that he’s always had my best interests and rapid growth in mind. Despite knowing that I will thrash when he pushes me to figure out something hard by myself, he does it anyway. He knows that I will be a better leader because of it.

It is insufficient to view your weaknesses only through the lens of your own development.

I’ve become a lot more comfortable discussing my weaknesses, but I’ve largely thought about these weaknesses with respect to … me. How do they affect my growth, my opportunities, my development, my effectiveness, my impact. Recently, I’ve realized that it’s important to think about weaknesses with respect to how they affect others. Take something like ineffective delegation. This is a known weakness of mine, but one I’ve often put on the back-burner because I’ve thought, “This just relates to my bandwidth.” Someone recently pointed out, however, that by trivializing this issue I am actually stunting the growth of others. As written, it seems so obvious that it’s painful to admit how monumental this conversation was for me. Mind, blown. The urgency with which I am trying to correct this is now 10-fold.

It’s easy to use your modus operandi as a crutch.

We’ve been told time and time again to “be true to who you are.” There are many cases in which this message holds very true. A fellow female recently told me that I need to be less “mom-like.” The best way to describe my peer is fierce, intense and highly rational. This is why people respect her and this is how she gets things done. I am intuitive, approachable and overcommunicative. But I also get things done. That said, I’ve historically overindexed on factors that make me who I am. I have implicit trust for people who are “like me” or who I “like” but implicit distrust for people who are difficult, despite their intelligence. In college, you largely get to choose who you work with on group projects. In my previous career in private equity, I was surrounded by very bright people, but there was limited diversity. At Palantir, I’m immersed in teams where people have all sorts of backgrounds, many of which I know very little about. Sometimes it’s easier to tell myself that I just can’t work with so-and-so because he is so frontal, or unintuitive or [insert something I’m not]. The reality is that if I want to grow, I need to figure out how to work with people who are different, trust them, help them succeed and help them help me.

Leadership is lonely

The most challenging lesson of them all is that leadership is often lonely. In the last year I’ve found many people, organizations and constructs to blame: the incessant travel, the rapid growth of my team across multiple continents, the nature of business development roles, the rat race that is New York City. I thought that the problem might go away if I changed roles or teams, companies, industries or cities. Then I spoke to lots of people, in different roles, teams, companies, industries and cities, and I found that this is a truism of leadership that no one seems to really talk about. So, how to address it? Well the first step is probably making time for yourself and your priorities outside of work. Some folks claim that this is the only way, but I fundamentally do not believe this. If we are all giving so much of ourselves—our time, our skills, our emotional capacity, our creativity—toward a common mission, I have to believe that there are ways to develop a stronger sense of community. I’m on quest to find out how, and I hope to report back with some useful tips shortly!



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