How to lose your dream job in three easy steps

When I landed the Content Marketing job at Asana, I felt like I had made it home. Then I blew it.

Daniel Kaplan

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I brought my iPad with my resume on it to a coffee meeting with Kenny Van Zant, the head of business operations at Asana and the hiring manager for a newly-opened marketing role. The job they’d posted was for an Online Marketing Manager, and I told Kenny off the bat that optimizing AdWords and marketing automation systems wasn’t really my thing, that I was a journalist-turned-product-marketer who was mean with a keyboard and a blank screen but not nearly as mean with Excel.

I was sure he was going to tell me that my qualifications didn’t match what they were looking for at the time. Instead, his eyes lit up.

“That’s not what I was expecting when I walked in here, but, you know, we may have just the thing,” he said.

They hadn’t made it formal yet, but Asana was also looking for a content marketer – someone, Kenny said, who got the ins-and-outs of marketing and could write like a dream.

For the next 2.5 months, I went all out to land the role. I created a special account in Asana, filled it with the the projects I would do if I was hired. Over lunch, I walked Kenny through it, task-by-task. When he asked me to write a sample essay about the meaning of Asana’s brand, I worked on it until I felt I’d nailed every word.

The team was sufficiently impressed. I got the job.

An entrée into the role of my dreams

I had just landed the role of my dreams: the first marketing hire at a startup whose ambitions, if realized, could have a meaningful positive impact on humanity and the world, with a promising early product, some great customers on the roster, and some of the most visionary investors in Silicon Valley on the board.

Within three weeks of my start date, Asana was to launch Inbox – a new feature that would finally make it possible to use Asana with your team without relying on email. It was my first chance to shine at my new job, and I did.

Working closely with Kenny and Justin Rosenstein, we came up with a bold story that positioned Asana as the first credible post-email application. Email, we wrote and told the press, had become a counter-productivity tool, and Asana was going to clean up the mess. The blog post I wrote got 727 likes, a whole buncha tweets, and even links from several of the blogs writing about the launch.

If I were prone to doing such things when excited, I might have wet my pants.

Instead, I shit the bed.

The end begins quickly

Shortly after the success of the Inbox launch, I set about building an agenda for the marketing function at Asana. I saw three things that Asana could do to take its marketing to the next level, and got to work pursuing them. I wanted to fully define the on-boarding funnel, build three customer personas, and produce content according to an editorial calendar that would navigate each persona through every step of the way towards pulling out a credit card and making it go bling-bling.

If all of that sounds reasonable, you missed a key element of the above paragraph.

You see, these were all my ideas, my priorities, the three things I believed were most important. Three weeks into my job at Asana, with a single success behind me, and I was acting like I had answers to everything. I completely neglected to first ask Kenny – my new boss and a remarkable marketing mind – what he thought.

The friction was almost immediate. When I lobbied to test Mixpanel or KISSmetrics to measure and analyze the funnel, Kenny pushed back hard. We debated it for a month, until one day, Kenny declared that we wouldn’t be using any off-the-shelf products for this purpose and that the issue was over and done with, full stop.

Next, I wanted to create a customer survey, interview a handful of Asana’s most passionate customers, and use the information I gleaned from both to create detailed buyer personas. My logic was sound: to create remarkable content, I thought it would help to know the fears, hopes, and dreams of Asana’s target audience. But I didn’t communicate my goals in a clear, compelling way. It turned into another debate. Two weeks in, I’d written a survey that I didn’t believe in and that Kenny didn’t really support. I never sent it out.

At the end of the first 90 days, I think, it was already all over. Kenny had either discouraged or straight-up shot my first big initiatives, and I never recovered from the wounds. For the next eight months, I limped along, managing Asana’s blog and trying to build a content program that everyone could get behind, but it was not to be. When, seven months in, Kenny handed ownership of a big content project to a contractor, the writing was on the wall. It was in big, bold lettering, and it said “you are dead.”

Four months later, I was shown the door.

Losing the job of my dreams in three easy steps

After much reflecting and self-investigation, I’ve boiled down the process I used to lose my dream job into three easy-to-follow steps. If you, too, have landed the role you’ve always wanted and you’re looking for a surefire way to send it down the drain, you can approximate them, yourself, to magnificent effect.

They are as follows:

  1. Assume that just because you’re smart, you’re also credible. At Asana, the first mistake I made was to think that the successful launch of Inbox meant I was now officially credible. I neglected to grasp that credibility is a slowly-earned reward, and that to get a meaningful dose of it early on, you have to have really focus on the priorities of your manager and your team. I was just beginning to earn Kenny’s trust with that one small success, and assuming too much, too early ensured that the early trust would dwindle away.
  2. Move way too fast. After the Inbox launch, I immediately proceeded to take it on myself to diagnose Asana’s marketing challenges. Instead of building rapport with Kenny by working through the challenges and solutions with him, I came up with my own definitions of the problems and my own answers to them. Kenny did not approve. I was in a new environment, in a new culture, reporting to a new boss, and I started advocating for my own ideas before he knew who I was or what I was capable of. I racked up a few points in the wrong bucket there, for sure.
  3. Push too hard. When I wanted to test out Mixpanel or KISSmetrics and Kenny didn’t embrace the idea, I pushed harder. Instead of taking the time to listen mindfully and understand his concerns, I kept on advocating for the solution I had in mind. I became so invested in creating an outcome that proved I knew what I was doing that I lost sight of the most important asset: my relationship with my boss. The worst part is that I didn’t really care that much if we used one of those tools; I just wanted a way to answer my questions. But instead of communicating what I was after in a way that Kenny could embrace, I put him a corner. #epicfail

The wrap up

Looking back on all of it, it wasn’t any catastrophic meltdown that cost me my dream job. It was much more insidious and stupid than that. It was a slow melting away that originated from a lack of mindfulness –like when the scoops of your ice-cream cone slip off and splat because you didn’t consider the heat.

It took me a while to come to it, but it’s now obvious to me that all of this was avoidable: All the clever ideas you have don’t matter when you don’t focus on the relationships. When the important ones go sour, it doesn’t mean anything how smart you are, how good your writing and thinking can be…it’s all nothing in the context of whether or not you can communicate effectively with your boss.

It’s now so obvious that it hurts.

These mistakes did not sprout from a lack of kindness in my heart. No, they were simply the dull edges of the blunt instruments I used to deal with my fear. My fear of failure. My fear of success. My fear of being wrong. My fear of being right. My fear that humanity will fail to rise to the challenges of the 21st century and that we will all watch it render tremendous suffering as a result. All of it: one big vortex of uncertainty, spiraling outwards, consuming all things.

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Daniel Kaplan

I finally found the power in storytelling I always knew was there. Learn what I do at http://exponents.co