Fostering a Healthy One-on-One Mentorship

Tripta Gupta

Engineering Manager at Brex



A company is composed of many people - some managers tend to focus intently on a few individuals, but I have found that engaging my reports more directly organizes the group as a whole. A one-on-one relationship increases interconnectivity between departments. This pairing structure provides immediate access to advice, direction, and support.

I was hired into my current role six and a half months ago. One of my reports had been with the company for five years - wishing to earn his trust, I spent time establishing a personal connection with him. What type of environment burns him out, where does he thrive? What are his goals, what types of challenges refresh him?

Actions taken

After doing my homework, I became more acquainted with my employee’s needs. He expressed that his step-up ladder within the company did not feel realistic. This was valuable feedback, giving me the tools I needed to set him up for success. Without a one-on-one relationship, these connections would have never been made. I share my own experience, hoping to inform their own.

There’s this concept called rubber duck programming - you put a rubber duck in front of you, and you pretend to talk to the rubber duck about the problem that you’re having. A fifteen-minute pairing session with a trusted manager addresses the same need, with the added benefit of providing viable feedback. I am lucky to manage a team able to pair almost all of the time.

To begin one of these sessions, I put myself into my employee’s shoes. I give them alternative solutions to their problems. This not only solves the problem; I learn how they approach obstacles and where they tend to run into trouble. Providing this open space builds a personal relationship that keeps us all on track.

Lessons learned

  • Consider your company holistically - the health of the individual becomes the health of the group as a whole. A one-on-one mentorship gives us space to examine the human condition as it relates to who we are for eight hours a day.
  • Our careers are bigger than our daily tasks, and our lives are more than our office hours. Thinking of your employees in this broader context allows them to grow beyond what it will take for them to get that next big promotion.
  • When pairing my employees, I take care to choose mentors who have already found success in their desired area of specialization. If I have an Engineer with great potential as an architect, I put them in touch with successful architects within the company.

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Tripta Gupta

Engineering Manager at Brex

Leadership DevelopmentCommunicationMentorship ProgramsFeedback TechniquesCareer GrowthCareer ProgressionIndividual Contributor RolesStaff EngineerPrincipal EngineerTech Lead

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