Lessons learned from failing as a leader

Tina He
Tina He
Mar 3, 2019 · 5 min read

The below is an excerpt from my weekly letter for my newsletter.

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Hello, beautiful people —

A friend and I reflected on our times leading teams or organizations. We talked about how our ideas about leadership have shifted quite a lot.

The conversation made me realize how lucky I’ve been in the past few years to have many opportunities to lead and to do a terrible job at almost all of them. I never knew what leadership meant even after reading tons of Medium articles or HBS books on it — this again shows that some knowledge only comes to life with experience.

With less than a few months left, I do feel the urgency to be as useful and valuable as I can as someone armed with an @.edu email, hoping someone gains comfort and perspective from the mistakes I’ve made.

The biggest misconception I had about leadership is that it comes with a title. Having the title of a manager or a president doesn’t make them leaders. Instead, a good leader comes down to what they do and whether they can do three things very well: to understand, to direct, and to inspire.

They understand by knowing your superpower and trying to see things from your point of view, they direct by envisioning a better version of the current situation and showing the best way to get there, and they inspire by their characters and relentless pursuit of their visions. You usually know you are working under a great leader when you feel propelled to become a better version of yourself, as uncomfortable or stressful as the process may get.

Someone can a decent manager by doing just one of the three things, and someone whose mere incentive is the title itself can end up doing none of the three things. On the other hand, the three things can be accomplished without a title. This leads to my second misconception about the prototypes of a good leader.

Being an MVP doesn’t mean being a great leader. Being an MVP can be quite effective when the group benefits from everyone in the group wanting also to become MVPs. That’s why the captain of a sports team tends to be the best player on the team because it’s best for the team when everyone wants to become a better player in that sport. That’s why being the best designer doesn’t make someone the best leader, because not everyone wants to get better at pushing pixels on the screen.

I’m proud of the things I’m good at, but those strengths can turn out to be crippling for others on my team. I once had a team member came up to me, brows tangled with distress: “Could you handle this for me? I would never be as good as you are at design.” I knew I was doing something wrong because she is a marketer, and her primary focus shouldn’t be creating beautiful designs. It’s not hard to see where she’s coming from; my pixel gorgeous presentations with fancy mockups wrongly insinuate that great marketing has to look like that.

This is a classic failure to align context. A good leader comes in all flavors, but they can all align expectations with the people they are leading. A leader of a product team that optimizes for business metrics should empower creative solutions and prioritize high-impact features, and a leader of an under-represented minority group should focus on making sure their members’ voices are heard, valued, and amplified when the time’s right.

All these mistakes also made me realize that there might not a right answer to good leadership. A great leader in one context can be terrible in another context. I got overwhelmed by the thought that I might not be able to do everything right, but I do feel responsible, and as a leader, I feel obligated to take the blame. This led to my last misconception about being a leader: the importance of a leader.

As important as we know great leaders are, the most effective group can achieve optimal outcome without clearcut defined leadership roles. Everyone takes ownership over their work; everyone their own boss. By taking too much blame and taking myself way too seriously, I stopped having fun, and every problem of the group becomes problems that keep me up at night. I became unproductive, irritated, and at one point cynical. The number of dank jokes I spit out wasn’t positive for our productivity or morale.

It took me some time to figure that if I’m having fun during the process, my joy will infect those around me. When everyone’s happy and motivated, they’re cranking out work even when I take some time off from checking Slack and Gmail frantically. I let go a bit and decided I wanted to have fun, and surprisingly everyone seems to be better off because of that.

Thank god after sucking for years, I think I start to suck a bit less. Some questions that have worked magic for me:

1. Why are people in this group? What motivates them to join? If they don’t have an answer to those questions, I should at least share with them why I decided to do this thing.

2. What are their metrics of progress? What are their superpowers? Are there tangible ways I can help them achieve those metrics by leveraging those superpowers? Is my assessment the same or different with theirs?

3. Am I doing my best to get to the shared vision of the group? Am I spending too much time managing tasks than doing the work to get there?

Everyone can benefit from becoming a better leader knowing that there’s no right answer to this. The process becomes one of self-discovery and a more well-rounded person who’s able to live for something bigger than oneself. So why wait?

Stay real,


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