On Leadership

One of my projects this year is continuing my business education through classes offer by the University of Delaware. Below is an excerpt from one of my reflections for one of my courses.

It seems clear to me the quality of the work a group does will never exceed the quality of the group doing the work. When I working remotely I dealt with an additional management challenge: how to lead and manage teams that were working across the country, and even across the globe. Members of my department worked from Puerto Rico, Australia, and Boston.

Specifically, I wanted to reflect on the three C’s of leadership mentioned in Chapter 19:

1. Competence. The video in Module 2.1 mentions that technical skills were most important for a front line managers, given that they are closest to the people doing the work.

This reminds me of an article in the Harvard Business Review titled, “If Your Boss Could Do Your Job, You’re More Likely to Be Happy at Work”. The research mentioned might have some problems—it’s self-reported, and who is willing to call their boss “competent” after saying they don’t like them? But it makes sense that front line managers are generally more well-liked when their reports don’t feel they’ve lost touch with the work they do.

I’m a fan of how David Ogilvy described his former working relationship with the head chef of the Hotel Majestic in Paris. Ogilvy details in his book, Confessions of an Advertising Man, how Monsieur Pitard would occasionally step back into the arena to show his cooks “managing” had not dulled his artistic talents:

He had to spend most of his time at his desk, planning menus, scrutinizing bills, and ordering supplies, but once in a week he would emerge from his glass-walled office in the middle of the kitchen and actually cook something. A crowd of us always gathered around to watch, spellbound by his virtuosity. It was inspiring to work for a supreme master.

Following Pitard’s example, I still write occasional advertisements myself, to remind my brigade of copywriters that my hand has not lost its cunning.

—David Ogilvy, Confessions of an Advertising Man

It’s important for managers, many who lead groups of creative people who care deeply about their craft, to not come off as empty suits who have lost their taste and teeth. As my job involves managing writers, I think about this quote a lot.

2. Consistency. “Dependable” might be the highest compliment you can give—to objects, processes, and people alike. For example, no matter how nice a vehicle is, the most important characteristic is that it turns on every time you turn the key. Anything less just won’t work.

Leadership is the same way. A brilliant but inconsistent leader, or manager, creates a feeling of uncertainty and unpredictability; two traits that are the antithesis of confidence. How can you expect your reports to be confident in your ability to deliver if you don’t do what you say, or if the environment you create isn’t conducive to “if we do well, things will go well?”

3. Caring. According to a study by Gallup, one in two people admitted to having left a job due to a bad manager. Besides perceived incompetence, I’d imagine the biggest source of frustration is when it feels like they don’t appreciate you or your contributions, or when management leaves you feeling like a cog in the machine instead of a person with aspirations for growth and achievement.

At Help Scout, we were invested in helping to grow everyone’s skills. Two big ways we stayed committed was frequent, open-ended 1:1’s and a learning stipend for employees who had been with us at least a year. 1:1’s were really important for us as a remote team, so we wrote up an internal doc of best practices.

For our learning stipend, we encouraged people to spend time and money on industry conferences, books, online classes, and even private coaching. That’s something I now look for at every company—it shows a company is willing to put skin in the game and truly invest in your future, not just with the company, but as a whole.

In all, I thought this section was especially important because managing code, copy, or processes is easy compared to managing people. I don’t think any business can succeed without finding product/market fit and the right people, and the right people are far harder to find.


I’ve a number of ongoing WordPress projects that I manage in addition to schoolwork and my new job as a content marketing lead for Shopify.

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