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People Management

Careful What You Wish For...

Do you really want to be a people manager?

July 30, 2020

If you work in tech, there's a good chance you're a real grinder; you're self-motivated, with ridiculously high standards and a carnivorous attitude about crushing your goals.

And if you are indeed an overachiever in your individual contributor gig, you probably expect others to notice and reward you for your accomplishments.

Beyond the common desire for more compensation, many see a promotion to people management to be an inevitable and desirable next step. It's the textbook career ladder - first, we master a craft, then we run a few cross-department initiatives, and then we take on a team of our own.

Why Would I Not Be the Best Manager in the World?

If you are absolutely crushing it as part of a team, imagine what it would be like if you ran the team? You know the business, the product, and what success looks like.

It's a match made in heaven.

So why is it that so many first time managers — who clearly know the company and have already excelled— struggle, and I mean REALLY struggle when they are given teams to oversee?

The dark secret...

What nobody tells you when you are offered your first management job is this:

"The things that made you a great individual contributor will likely have zero bearings on your skills as a manager."


Your high standards, attention to detail, obsessive-compulsive, maniacal drive to get-shit-done-at-any-cost may be your collective undoing as a boss. And worse - nobody tells you this until you are knee-deep in team morale problems, HR complaints, and a bundle of negative GlassDoor reviews.


Bringing Your IC Self to a Manager Role

Let's look at the prototypical top dog sales performer as an example. If On the Origin of Species was written with revenue in mind, Darwin would have opined that a top salesperson must have thick, scaly, reptilian skin to survive the countless phone hang-ups and lost deals, and crushing pressure to produce.

They cannot be oversensitive. They must remain a body in motion — since activity begets activity — so can't stop and dwell on losses or failures. Similarly, they cannot get overly focused on details, lest that slow their overall activity. (Show me a sales guy with all of his ducks in a row, I'll show you a sales guy with a crappy pipeline.)

Now, at this point, I should note that I'm a sales guy at my core.

But give a high-performing salesperson a team to manage, and it's often a train-wreck.

How do I know?

Because I was that train-wreck.

I took my first sales job in January of 2000. By mid-2001, after crushing my number for six straight quarters, I was given a team of 10 enterprise sales execs... and it was a nightmare.

I commandeered calls. I yelled at folks who couldn't match my pace of work. I micromanaged–down to reps' email structure and punctuation. The traits that aligned so well with that of a high-performing salesperson were, in many respects, mutually exclusive with the traits found in good people managers.

Tell Me What You Really Think

Years later, laughing about my less-than-optimal style over drinks in Chicago with a few former colleagues, I found out that my team members had kept a list of "Wilner-isms"– quotes from me that they amassed over time. Here are a few of them:

  • "I would have expected you to be better at this by now."
  • "I don't need your MBA-speak–just give me a straight answer."
  • "If I have to take these calls with you, why am I giving you commissions?"

...and my personal favorite

  • "I've shown you how to do this three times, and you may actually be even worse now than before."

As a salesperson, I was outstanding.

As a young sales manager, I was a five-star asshole.

Like many top IC performers, I immediately defaulted to the so-called Pacesetting style of management. Pacesetting can be summarized as follows: "hey's not that me do it for you." That's the comfort zone for many top performers— see a problem, jump in quickly, and handle the issue. No patience. No coaching. No empathy.

I lost a number of good people, well over half of my team, before coming to the realization that I was failing badly in my new role.


Ask Yourself Why You Want to Be a Manager

This blog isn't about how to be a better manager. There are thousands of articles, books, blogs, videos, TED Talks, seminars at the Red Lion by the airport, etc. on this topic.

Instead, I hope to encourage you to reflect on why you want to be a manager before you double click.

So, be honest with yourself. Why do you want this promotion?

Is it money? The assumption that managers make more? Keep in mind this isn't always the case. Top performing sales folks will always make more than their managers. Principal Engineers tend to make more money than their supervisors. If grabbing fat stacks is your only motivation, best to double-check that your assumptions are correct.

Is it ego? The simple recognition that you're a badass at your job? The American Psycho gilded business cards with your important title? That's common. It feels good to get props, to have everyone see and acknowledge that you are valued. But when the novelty wears off, and it WILL wear off, you want to have a job YOU are happy with. A job you are well-suited for, where you can repeat your pattern of success.

Is it, "that's what I'm supposed to do?" It's easy to see a career as one ladder, one conveyor belt, one path. But in today's dynamic, constantly evolving world of technology, traditional rules about career path and trajectory are out the window. You are in control of your life.

Can You Embrace Learning New Skills... and Some Initial Incompetence?

If you are satisfied you want to be a manager for the right reasons, you need to ask yourself some other hard questions.

Are you ready to be really bad at your new job out of the gate?

Can you accept that you will likely need an entirely new set of competencies and skills?

Can you embrace the fact that being a great manager is not about telling others what to do, but instead helping them become the best they can be? A manager–a good manager–is much more coach than a dictator.

We most often fail by overestimating how far our domain skills and force-of-will can carry us in this area. We underestimate the work required to become a respected and effective leader.

Ready to Take the Plunge? Be Sure It's Intentional

This blog is not just a confession, some kind of penance for past sins (at least not entirely so.) After 20+ years in technology, much of which was in leadership roles, I find conversations with new managers to be the most interesting and satisfying work that I do. Hopefully, some of my mistakes, gaffes, embarrassments, and occasional triumphs can be a source of conversation for folks early in their careers.

I've been fortunate enough to help launch or accelerate the careers of hundreds of colleagues. It's a noble calling and could be one of the most rewarding things you do. It could also be an unfortunate and painful detour in your career, depending on your mindset and circumstances. Do the work before you decide. Talk to first-time managers to feel their pain. Get others' feedback about your skillset and any blind spots. Be honest with yourself about your motivations and your willingness to learn.

And hopefully, you can avoid sitting in a bar five years from now hearing what an asshole you used to be.

About Auth0

Auth0 by Okta takes a modern approach to customer identity and enables organizations to provide secure access to any application, for any user. Auth0 is a highly customizable platform that is as simple as development teams want, and as flexible as they need. Safeguarding billions of login transactions each month, Auth0 delivers convenience, privacy, and security so customers can focus on innovation. For more information, visit

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