Helping Your Reports Grow in Their Careers

Henry Hsu

Head of Engineering at Trade Coffee



"I have three angles I look at when talking about the development of people. First, what is my management philosophy and how can I apply that to the conversation? Next, what does the individual want? And last, what does the company need? With these three aspects I am able to talk with a report about the different ways to grow and figure out what is the best path for them."

Actions taken

My management philosophy

"In general, I want to build upon people's strengths and figure out how to make somebody the best version of themselves. Therefore, I begin by looking at what they are good at. How we can build upon that, capitalize on it, or help them develop it even more. Also, my job as a manager is to help people get to the next step in their career, whether that is at our current company or not. Based off of their life goals, I am here to help them along that path in whatever way I can. If I can help them and also help the company, well then that's a great win-win. I explain to reports that it is their career and what they want out of it is their responsibility. However, I am here to facilitate and create opportunities for them so they can get what they want. More so, I inform them that I can give them options but they have to tell me what they want out of life. It's just a matter of framing it in such a way to give them time to think about it and allowing them to come out with an answer on their own."

What the individual wants

"Ask the report to look at people around them and identify who they want to be (or who they don't want to be) in that group. These people can come from leadership, different teams, or from outside of the company. Take those names and have a conversation dissecting each person, what they are like, what they are good at, and what their roles and responsibilities are. Talk about why that person is interesting (or not). This gets the report thinking about what they want (or don't want) their career to look like."

The company's needs

"This will obviously vary greatly between organizations depending on size, finances, skill sets, and mission statement, among other things."

Lessons learned

  • "Sometimes people are happy where they are in their career. They aren't thinking two steps ahead and just want to be where they are. That's totally fine."
  • "There isn't a template to follow for guiding someone on their career path. What works in one situation may not work in the next, so try different things with different people. That being said, there are some situations I applied to another to test its effectiveness and had decent results."
  • "Get comfortable with the fact that neither you nor your direct report really know a definitive answer on the best way to develop and grow. Yet, you are both discovering and on the journey together, so be willing to have an exploratory mindset."
  • "As a manager, the path of your report shouldn't just be about what is available in the company. It doesn't necessarily have to follow a particular laid-out company track or the skills that develop along that track. Instead, is should be more about what the individual wants and focusing deeply on that conversation. After that discussion, then you can try to find places where they match with the company's objectives."

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Henry Hsu

Head of Engineering at Trade Coffee

Leadership DevelopmentCareer GrowthCareer ProgressionIndividual Contributor RolesStaff EngineerPrincipal EngineerTech LeadLeadership RolesEngineering ManagerVP of Engineering

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