That jerk might just be an angel in disguise ☺

I had a bit of an epiphany recently thinking about a really bizarre interview I had years ago where one of the guys was a complete a$$ to me. It was at a point where I had a good job but was realizing it was probably time to start exploring opportunities for my next gig. Someone I met at a dinner invited me to come visit a prominent private equity firm to talk about positions with their portfolio companies, so I jumped on it and was excited about what it might open up for me.

In addition to the guy who’d invited me, there was another sitting at the table. I started providing a quick overview of who I was and my background when he abruptly cut me off. He immediately started coming after me, disparaging my then employer, asking why I’d work for people of that ilk, probing on why I was “playing it safe” with my position and career strategy when it didn’t make sense vs. what my husband was doing (i.e., I should be pursuing something with a higher risk/reward profile to complement my husband’s more stable corporate lawyer role).

He went on to ask me a few questions about what I wanted to do next, what my career vision or goal was and I honestly said I was unsure and felt a bit stuck. I elaborated that in tech, I’d ended up doing what I loved—a bunch of everything, including sales, marketing, product development, services, and more—by getting to sit between the “guys who carry a bag” (a.k.a. sales reps) and the “guys who code” (i.e., engineers). I then started to explain that dynamic also created a challenge because many software companies didn’t have that role, that I was an applications-focused person and Boston mostly had infrastructure tech firms, etc.

He abruptly cut me off again, “You are completely boring me…I have no clarity on what you want to do…I don’t know why anyone would hire you…you need to go get a sales role if you ever want to be successful and a ‘real’ executive…” It got so awkward that the guy who’d invited me into their office stepped in to defend me, saying “Look, I asked her to come see us because her background is really rich and unique in tech, so I thought she might be able to help one of our portfolio companies…” At that point, I threw in the towel a bit and politely said, “I know you’re both extremely busy and I’m very grateful for your time and insights.”

As the “nice guy” and I walked to the elevator, I was a bit shell shocked by everything the “jerk” had said, and all of it lingered in my head for days, weeks, months, and even years after. I learned that several others who knew him had also struggled with his tough personality and that he was widely reputed to be an a$$.

All that said, I must say looking back that the guy was right (mostly) and his comments provided me a level of honesty that I needed then and thereafter to light a fire under my own a$$ :) and catalyze changes that I needed to make. I must admit that my initial reaction was one of defensiveness and dismissal, but hearing cold, hard truth from someone I didn’t know turned out to be an unexpected message from the “gods” trying to tell me something I needed to hear—that I needed to move on and figure out a clearer story about myself and what I wanted to achieve. It also helped me realize that my story needed to be focused on what I could do FOR prospective employers vs. dwelling on my own internal struggle around what I liked to do (or not), what I’d done (or not), what I could do (or not).

Fast forward to right here and now—and I’m in an amazing time in my life where I’m in the opportunity of a lifetime, working for a spectacular company that’s better for me on every possible dimension—personally, physically, financially, cognitively, socially, and otherwise. I can’t credit him with all of it but his annoying yet truthful voice inside my head certainly didn’t hurt and provided a much-needed wake-up call that pushed me to exactly the right place.

Beyond this guy, I talk about others of this ilk in my book, Men@Work: A career girl’s guide to navigating male archetypes. If you’ve ever seen the movie “The Departed” (one of my top five!), you might remember that the guy everyone thinks is “good” (Matt Damon) is actually bad while the guy everyone thinks is “bad” (Leonardo Dicaprio) is actually quite pure. This dynamic turns up a great deal in work and life more broadly—some of the colleagues or bosses who I thought were the toughest on me provided the most value over the longer haul serving as strong advocates and coaches while some of the guys who seemed good in the moment would often take advantage of me, claim my work as their own, neglect to include me in the room, and more.

Should you encounter one of these devils, I hope you’ll take the time to consider whether he or she might just be an angel in disguise. That person who pops up with cold, hard criticism and honesty might just be exactly the tough love you need to realize your next level of awesomeness. Worst case, you can use their jerkiness to fuel your drive to prove them wrong. :)

For more thoughts and advice on Tough Love, I hope you’ll check out my other blog focused on the topic. Or, if you’re looking for guidance on how to navigate these guys and the continuum of types you’ll likely encounter throughout your career, I hope you’ll take the time to peruse Men@Work.

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