Leading Your Reports to the Careers of Their Dreams

Vinodh Sundararajan

Sr. Engineering Director at Earnin



When our company was just starting up, we had decided that, no matter what somebody’s role in the organization was, we wanted our engineering team to have a certain standard of quality to hold themselves to. We wanted to acknowledge the fact that we were all engineers first, with the role itself ultimately being considered on a secondary basis.

Right now, I’m a senior engineering director, but our company culture dictates that my status as an engineer supersedes the director portion of the position. It was an important framework from early on, because it translated into how we conducted our interviews, how we charted career progress, and how we opened up opportunities for everybody in the company.

Actions taken

We take more of a coaching approach, rather than a strictly top-down approach to feedback. Many of the people who currently hold leadership roles in our company were people who joined initially as Individual Contributors. Some of them wanted to explore this path. They didn’t know what this career track entailed, so they wanted to see if they would enjoy it. Others had more conviction about their interest. Rarely, we would promote a leader who was reluctant but who recognized the urgency that we expressed while trying to fill the role.

When expressing a desire to step into these types of roles, we ask our employees to clarify their intentions. We look for candidates who wish to help the organization succeed as opposed to those seeking power and influence over others.

We’ve listed out a few parameters, dimensions of performance evaluation that show where there is room for improvement. Scope and impact come first. We also look for an ability to influence within the organization, as well as a certain set of technical skills. What really matters is being able to clarify what success looks like in each of these roles. Then, you will be able to identify any skill gaps that the candidate has. How can we best go about helping them level up in some of these areas so that they will be able to perform more competently as a manager?

Lessons learned

  • We found that for many, the biggest barrier was providing feedback. Our conclusion was that the best way to provide feedback is to avoid surprising people.
  • Every employee has their own vision for the future. Some may want to continue to progress in their technical career ladders. Others may want to develop themselves into people managers and leaders themselves. Once a manager has some awareness of the aspirations and goals of their reports, they will be able to apply their talent to objectives within the company that give them an opportunity to hone the relevant skills required to advance.
  • Before having any of these conversations in the first place, however, the report must be given some idea of what success looks like. This makes it easy to talk about what is going well and what is not.
  • Any time I tell somebody, “Here is the problem, and here is the solution.”, it always blows back onto me. The secret is to get the person themselves to acknowledge the problem and to try coming up with a solution. What we can contribute as managers is using questions to help them think through what exactly is going on.
  • Our model is called “SOON” — Success, Obstacles, Options, and Next Steps. We start with “Success”. What does success look like? Then, rather than me telling them what their obstacles are, have them write down what they think that their obstacles are. Where do they feel that they are struggling the most? Awareness of the obstacles then prompts the employee to start coming up with options. All of this then distills down to the next step on the road to success. What is a new habit that they can start doing today? Accountability can be upheld by checking in on this resolution.

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Vinodh Sundararajan

Sr. Engineering Director at Earnin

Engineering LeadershipLeadership DevelopmentCommunicationOrganizational StrategyDecision MakingCulture DevelopmentEngineering ManagementPerformance MetricsLeadership TrainingMentorship Programs

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