Career on Locally Optimal

Nobody will take care of your career like you will

Thu, 16 May 2024 00:08:09 +0000

The reality as you get more and more senior is your manager will most likely have more reports, and almost certainly have more problems under their scope. In fact it gets to the point where they are almost guaranteed to have at least one enormous burning fire active at any given time, simply due to the size of their org.

To navigate this, you must take the initiative in your career development and communication with managers. Understanding what you want to be optimizing for (career growth, work/life balance, new skills, etc.) and clearly communicating your desires is crucial. Be proactive in bringing information and suggestions to your manager so they can focus their limited time and energy on solving problems for you instead of guessing what you need.

You also (at least in my experience) likely have to admit that your manager or a single perfect mentor is not going to be capable of providing all you need. Building a rich network of peers and role models helps in understanding opportunities and challenges. You can also assemble a board of advisors (or a Voltron, depending on your preferred analogy) to help develop very specific skills from multiple people where no single person can provide them all.

Considering a detailed mental model of the company's landscape can aid in explicit career planning. Are there teams, projects, areas, or other that you’d like to steer your career toward? Treat your career like an enormous (hopefully very seaworthy) ship – the best way to avoid icebergs and end up where you want to be going is to notice issues early, start turning the ship, always keeping in mind the big picture of where you’re headed. Even the very best managers have limited time for your individual development – don’t outsource being the captain of your own career.

Guard your time jealously, use most of it for high leverage work

Thu, 16 May 2024 00:07:42 +0000

As you become more senior in your career, demands on your time will outstrip the hours you’re willing to work, no matter what. Your time, focus, and energy is perhaps the most immovable constraint on your output. There is a very real ceiling on the useful output hours you get per week – while you can raise the raw quantity of hours easily enough, it almost certainly comes at a cost on quality short term and sustainable energy longer term. So instead of adding hours, focus on making a fixed set of hours really count.

It's imperative for you to be an active owner/director of what you spend your time working on. This includes what to set aside, as not all demands can be met. As you get more senior, you’ll increasingly need to be an active participant in helping your manager and team prioritize what is right for you.

Focus on identifying the top one to three big efforts you want to consume the bulk of your project time. You should be in the details of these things, as is appropriate for your level, of course. Utilize your calendar effectively to ensure your time allocation matches agreed priorities and be ruthless in prioritizing essential participation and eliminating unnecessary commitments.

If you need or want frameworks, you can try the Eisenhower Matrix or LNO, but recognize that all frameworks are useful only in as much as they actually work for you. At the end of the day you should be using whatever tools in the toolbox get the best outcomes for your working style.

Finally realize this is not a one time intervention, it’s an ongoing process. Check in with your manager every so often and confirm these are actually the most important problems. I find my own “top 3” tend to change roughly once per quarter. The single best predictor of my priorities needing a reassessment is feeling overwhelmed or like I'm working on the wrong projects. You should expect and plan for periodic reassessments of your time distribution as priorities shift.

Take a moment to identify your current top three priorities. Does your calendar reflect them? Are they still aligned with your biggest impact areas? Schedule a 15-minute review with yourself this week and consider bringing any findings to your manager to discuss.

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

Wed, 20 Mar 2024 04:56:35 +0000

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.