What I Learned at My Last Job

At my last job, I learned what it really means to be a manager. For the first time, I managed other managers, and I had to build a team by hiring. I’ve added those things to my resume. But I also picked up little points of wisdom along the way. Those were even more valuable. Here are my key takeaways:

Pivots Are Hard

The term “pivot” is used when a company changes its business model. Specifically, I was pitched on helping the company transform from a content/SEO focus to a product focus. My teams built the company’s first non-content products.

This process was extremely painful. Three years later, even getting on the same page about what being a product meant was still an ongoing discussion. Basic concepts such as user engagement, what a product manager is, and engineering as a value center were still not universally well understood.

Learning: Non-product-oriented companies cannot become product-oriented without a LOT of pain.

C-Level Reporting Structure Matters

I did not fully understand the impact of the company being a “matrixed” organization. This turned out to mean that the company was split into many sub-organizations. Each one operated with independent leadership and engineering teams. In practice, it also meant that the various groups often worked against each other instead of with each other.

As part of the product pivot, all the groups, including a unified engineering organization, were put under a CPO (Chief Product Officer). This produced a gap in how engineering was perceived. Instead of seeking to understand how engineering could be empowered, the company attempted to tell engineers what to do.

Learning: For engineering to be properly valued, it needs to report up exclusively through engineering leaders all the way to the CEO.

Trust Your Business Instincts

I probably should have learned this lesson previously. As engineers, we have a tendency to abdicate serious thinking about business problems to business experts. But twice now, I’ve seen that I should trust myself more.

Once before, the red flag was a reliance on Facebook as a partner. This time, it was a reliance on Google and SEO. In both cases, those risks actually materialized into large negative impacts on the business. When you identify a red flag for the business, go into your role clear-eyed about that risk. People you interview with will have polished, buttoned-up answers to these concerns. Remember that they have had months or years to polish those answers! You are smart; don’t discount your intuition.

Learning: Take seriously any business risks you can self-identify while interviewing at a company. Don’t let anyone, even a founder, talk you out of your concern.

Tactical Stuff

Finally, here are some smaller, more tactical items I will take with me going forward.

  • The biggest reason projects fail is lack of alignment with upper management. You need to continuously realign.
  • Treat performance reviews as a year-round job. You should have a living draft of reviews for all your direct reports and regularly talk about the feedback with them. This is especially important if layoffs occur unexpectedly: you don’t want to add to the surprises.
  • Be flexible about team composition. You don’t have to create the ideal team right away, especially if there isn’t alignment with leadership.
  • In the face of ambiguity, a bias toward action should be tempered somewhat with seeking first to understand.
  • If you can’t sit down for a one-on-one with a high-level stakeholder, at least try to put yourself in their shoes.
  • Set expectations of confidentiality around personnel moves. Specifically when moving people between teams and when people are leaving the company, make sure anyone who does know ahead of time keeps it under their hat.
  • Be careful about executing a succession plan for yourself without knowing what your next role will be. Always do the right thing for the company, but you may be moved quickly into a new role that you’re not as excited about.
  • Identifying a problem is not enough. You also need to propose a solution. Otherwise, it’s just complaining.
  • Think about who to CC on email outside your direct group. Any email that you send above your boss in the reporting chain should also include them.


What I really learned was that in a management role, you need to think a lot more about the big picture. You need to think about not just the business fundamentals, but also the the highest level stakeholders.