Episode 9 - Kevin O’Connor

Summary

I’m here with my husband Kevin O’Connor who has recently left his job at Reddit to now work for Memorial Sloan Kettering Cancer Center in New York City as a Director of Engineering. In this episode, he’ll walk you through his career journey in the tech industry. Learn about his take on managing former peers, managing up to his leaders, and how he’s used his privileges to help those around him. Also, just note that if he sounds like he knows what he’s talking about, it was because I coached him throughout his career. But if you don’t agree with what he says, that’s on him.

Questions and Time Stamp

Scan your resume. [2:37]
You were in tech your whole life, and now you’re going into healthcare. Total different jump. Why the change? [5:20]
How would you describe the tech industry compared to other industries? [7:23]
So going to this new industry in healthcare, what do you think will be some obstacles that you’ll encounter? [8:24]
Do you think [your new job] will be stressful because the stakes are so much higher? [9:50]
Do you think it was by luck that you got where you are today or was it hard work? [10:44]
How do you learn best? [11:44]
When you got the news that you were going to be an Engineering Manager, what was going through your mind? [13:00]
I’m sure you had to manage some former peers, what was that like? [13:50]
Why [was managing former peers isolating and lonely?] [15:04]
What is advice you would give someone who is going to manage a former peer? [15:52]
What do you think would happen if you didn’t do a new manager assimilation and you just went straight to management mode? [17:42]
How would you describe yourself as a manager? What is your management style? [22:06]
How do you measure if you're providing business value? [23:02]
Where do you need to improve? Where would you like to get better? [26:37]
How do you voice a dissenting viewpoint to leaders? [31:01]
How do you manage up to a manager? [36:07]
How do you find out what motivates them? [36:47]
Once you find their motivation, what do you do next? [37:46]
What if it’s a personality issue you need to manager up like your manager talks way too much, or is always late to meetings, or cancels meetings all the time. What do you do in those situations? [38:38]
How would you describe yourself in terms of race, ethnicity, gender, age, etc.? [41:28]
How has your identity positively or negatively impacted your career? [42:33]
You’re pretty self-aware of the privileges that you have? How did you get that way? [45:49]
How have you used your privileges to help those around you who do not have the same privileges? [48:49]
LIGHTNING ROUND [52:14]
What advice would you give to new managers just starting out? [57:08]
What advice would you give someone who wants to advance in their career? [59:44]
Any books, articles, resources you recommend to people? [1:02:57]

Resource Links

New Manager Assimilation

The Manager’s Path by Camille Fournier

High Output Management by Andrew Grove

An Elegant Puzzle by Will Larson

Will Larson’s Blog

Guest Bio

Kevin O’Connor is a Director of Engineering at Memorial Sloan Kettering in NYC. In his spare time he likes to play volleyball, climb the steepest hills on his road bike, and playing video games with his buddies. He currently resides in Brooklyn with me (his wife!) and daughter.

Hosted by

Jessica Nguyen

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