Ask your manager for 5 growth areas, so they can pick 1-2 that actually work

I always try to remember two golden rules of managers – they’re often busy juggling many problems unrelated to you, and they cannot read your mind. 

I have heard (and have also sometimes personally felt!) complaints like “my manager isn’t offering me the opportunities I want” or “my manager doesn’t get what I care about” or “I don’t care about my job” or “this company doesn’t support my growth”. These are both 1/ valid feelings I don’t want to pretend aren’t real and 2/ frequently unhelpful framings. Both are something you can directly improve with a little bit of honest communication. 

Your manager is not a mind reader. They are probably burdened (like you are!) with a metric ton of other problems. Your career growth doesn’t have to be more important than the severe incident they’re dealing with, but it sure needs to be loud enough to be noticed over the general din and business of an average month at your company. Tell your manager what you want. If they’re a phenomenal people manager, have the spare energy, and feel like taking a fun risk in a 1-1 sometime, they might call you out unprompted and guess at what would make you happier. But in all likelihood, they’re exhausted, they're dealing with something outside work with their kids/partner/parents, and/or they just aren’t sure enough to justify guessing at what you need. 

If you want to change your work or grow your skills, set aside explicit time in a 1-1 and give your manager a too-large set of things you are interested in improving/practicing/whatever. I like to say “5 skills I’d be willing to learn” as a rule of thumb. The point is your manager has their own universe of constraints they’re juggling – people, roadmaps, project deadlines, planning overhead, and a bunch of other reports’ interests to balance. Inevitably your list of 5 growth areas  will not all be realistic right now, and that’s okay. You come with several options, your boss counters with the subset of those that actually match with constraints of reality, and everyone leaves with a better understanding of your interests and a mutually beneficial outcome. 

Bonus points for making sure you tie the skills to specific behaviors or roles. Recently I did this for myself – I wanted to absorb and learn more of Stripe’s secret sauce for building and releasing great product APIs, and concretely proposed that I get more involved in the approval process for APIs. Being specific makes it that much easier for your manager to understand how to help you, and has the bonus of you getting to name your (ideal) instantiation of the skill.

A company (at least a growing/expanding company like Stripe) is always looking for people to step up and handle more. If that’s interesting to you, help your manager help you by explicitly listing what you’d like, giving a few extra options for flexibility, and accepting that your manager has their own constraints to respect. The outcome should at minimum be a better “mental model of what you want” for your boss, and very likely a good project/role match for you.

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