Akhil Gupta on navigating uncertainty when transitioning roles

In Episode 10 of Lead Time Chats, Jean Hsu, VP of Engineering at Range, talks to Akhil Gupta about how to navigate uncertainty when transitioning to higher impact roles. How do you know when you’re ready for that next role? How do you fill in gaps, and when do you take the leap?

Akhil started his career at Google, and was a Principal Engineer by the time he left for Dropbox. At Dropbox, he grew the infra org from just 10 engineers, and stepped into the Head of Infrastructure role, then VP of Engineering, and then GM and VP of Enterprise.

Jean and Akhil discuss:

• Akhil’s transition to management at Google — going from 0 to 40 direct reports!
• How to surround yourself with people who are rooting for your success, as you transition to greater impact roles
• The biggest challenges of transitioning from a functional leader to a cross-functional leader (i.e. VP of Engineering to GM of Enterprise at Dropbox)
• What relationship-building looks like when your org has thousands of people, and 1:1s won't scale!

Takeaways from Akhil

Ask for help in new roles!

“It's absolutely important for you to ask for help when you're taking on a new role. People often mistake that if I ask for help, people will know that I'm not good enough. It is far more important for you to say, look, this is new for me. I do not know how to do this. You have done this thing for the last five years. Could be your manager, could be your mentor, could be an external coach. Can you guide me through these things, these are things that I'm struggling with. And if you do that, then you realize actually more people want you to succeed because their success depends on you. They don't succeed if you don't succeed. And if you reach out for help, I'm yet to find someone who says no.”

Look externally to build a network of mentors

“The other thing that you have to do is build a network of mentors, even outside the company, so that you can get advice from someone who may have a different perspective. Sometimes it helps to have someone who's not in the nitty gritty of your day-to-day job or whatever's going on in your company.”

Understand people's motivations first

“I think of my philosophy as more people first, where I tried to understand, what is their motivation? What are the incentives a person has on the team? What makes them happy? What makes them productive? And then use that to see what can this team achieve.”

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About Lead Time Chats

Listen in on unscripted conversations between Jean Hsu, VP of Engineering at Range and engineering leadership coach, and engineering leaders and other influential folks in tech.

Lead Time Chats is brought to you by Range. Range helps hybrid teams check-in asynchronously about what matters most. Know what's happening through status updates that pull from tools like Github and JIRA without scheduling yet another meeting.

Checking-in with Range creates more focus time for heads-down work, all while feeling a deeper sense of connection and belonging with your team. To learn more about Range, you can check it out here.