3 frameworks to help you make better career decisions

Key takeaways from “Founder’s Journal” episode 32 with Romeen Sheth

Link to podcast

My advice to founders and startups generally falls into one of four categories:

  1. How to be more strategic in your recruiting
  2. How to figure out what you really need to hire for
  3. How to hire the best people for what you need
  4. How to assess and manage your team

Each person that a company hires, especially in early-stage startups, is an important investment that can have outsized impacts, both good and bad, on the company. Onboarding new team members not only takes up a lot of time, money, and energy but also brings with it a substantial opportunity cost. 

This pales in comparison, however, to the opportunity cost and investment that an individual makes when they choose where to work, or what to work on. Whereas a startup has many positions to fill and several chances to hire great people, you as an individual can typically only have one job, or work on one project, at a time. This means that your choice of what to work on has a far more significant opportunity cost than a company’s decision to hire.

Many people haphazardly make career choices or take the first opportunity that sounds interesting, because they don’t have a guide that helps them ask the right questions before choosing what to work on.

I enjoyed this short podcast, where Romeen Sheth, CEO of Metasys Technologies, outlines three frameworks that can help people make better career decisions: choosing where to work, building a personal working guide, and how to transition if it’s not working out for you. In this article, I outline Romeen’s three frameworks and include my thoughts after each section in italics.

This guide is valuable for anyone, from someone just starting their career, to an experienced founder. Feel free to jump around to each of the 3 frameworks depending on your situation.

Framework 1: Choosing where to work

Romeen says that one of the biggest mistakes people make is not evaluating their career decisions with intent. You should evaluate career decisions with the same degree of rigor and thoughtfulness that investors apply to their investment decisions.  When evaluating whether you want to work somewhere, ask yourself three types of questions:

  1. Company-Market fit: 
  • ​​Is this company going to win?
  • How’s the company doing? 
  • What’s their traction? 
  • What’s their burn? 
  • What’s their valuation? 
  • What’s the company vision? 
  • What’s the strategy for how the company scales?
  • How do they make money? Is it sustainable? 
  • Who’s the competition? 
  • Who are private and public competitors, and why are they better or worse? 
  • Who are the customers? 
  1. Person-Company fit
  • Am I in a position to succeed?
  • Who’s the team I’m going to be working with? 
  • What are the other teams I’ll be interacting with? 
  • What’s the attrition rate of employees? 
  • Is the company a leaky bucket? Or do people actually stay? 
  • What’s the day-to-day responsibility of the current role? 

Most people early in their careers overvalue their position and undervalue contributing to a winning team. High-growth companies unlock opportunities. They’re the opposite of zero-sum environments. That said, what you do in the short term does matter; you want to be in a position to succeed.

  1. Person-Problem fit
  • Am I in it for the long term? You should imagine spending the next five years working at a company. 
  •  Is this a problem or industry I care about? 
  • When it gets tough, and it always does in any business that you’re in, am I motivated or excited enough to stick it out? 
  • Do I believe that I can uniquely excel in this domain? 

Matt’s thoughts:

You’re never going to have 100% of the information above when you decide where to work. Even the answers you do know today might change over time, especially in startups. That’s OK. What’s important is to ask yourself all of these questions and think critically about where you’re going to work, or what you’re going to work on. Remember, choosing where you are going to work is a huge investment, so make sure you are making as educated a decision as you can.

Framework 2, Building a Personal Working Guide

Romeen says that most conflict in the workplace doesn’t actually come from disagreement over substance. It comes from disagreement over style.

As organizations get larger, style issues start to emerge, from relationship dynamics, varied opinions, conflicting personalities, and disparate interests.

The intention of a personal working guide is to help the people you work with understand your personality, how you think, and what interaction approaches work best for you. Most importantly, it’s not a mandate or set of rules. It’s a starting point for a conversation on how to best work together.

Here’s what to include in your personal working guide

  1. Your personality type
    • What do I get energy from? In what types of environments do I succeed? What are the areas I’m working on to improve? 
  2. Your operating principles
    • How do you like to work? How do you like to collaborate? What’s your default mode of problem-solving? 
  3. Your communication style
    • How do you like to receive and share information? How do you learn best? How do you like to receive feedback? What’s your default mode of communication? Is it text? Is it verbal? Is it just in time? Is it async? 

Matt’s thoughts:

One of the main reasons startups fail is because cofounders don’t work well together. At Magma, we strongly encourage all leaders to fill out their own “Operating Manual” that their team can access. It’s a great way for team members to know how to best work with you, rather than guessing. You should not only fill one out yourself but also encourage your team members to fill one out as well. Follow this link to find our recommended guide for building your own Operators Manual.

Framework 3: How to transition if it’s not working out for you 

Romeen believes that most people idealize careers as clean linear trajectories. They’re not. They’re windy, they’re messy, they’re filled with ups and downs.

People usually get stuck in their careers because of one of the following thoughts:

  • Fear: “I feel like I’m gonna fail. I don’t know what I’m doing.” 
  • Insecurity: “I’m not where I thought I’d be at a certain age and time.” 
  • Resistance: “Am I gonna fit into this new environment? Maybe it’s just not meant to be.”
  • Ego: “I know too much, and maybe I think I’m too good to start over.”

Careers have highs, lows, and everything in between. If you internalize this, it’s liberating.

Now, if you’re making a job switch, ask four types of questions about peak, velocity, endurance, and personal fit. 

  1. Peak: How high can you go? If you make the switch, what’s the potential upside of this new direction?  
  2. Velocity: How fast can you get there? If you do end up making the switch, are you set for a slow and long grind? Or is it a curve that’ll require deep learning and familiarity, but once you’re up to speed, you’re gonna be able to really accelerate fast?
  3. Endurance. How sustainably can you get there? Will you personally endure the path for a long period of time?
  4. Personal fit. If you get there, how do you feel? This is a forward-looking exercise. You should envision you’ve climbed the mountaintop. High fives all around. Do you feel great, or do you feel empty?

Matt’s thoughts:

A lot of people stay in their roles longer than they think they will. Their current job might offer them a feeling of security, and thinking of new opportunities is anxiety-inducing. It’s perfectly okay to stay in your job, but don’t do so out of fear, insecurity, resistance, or ego. 

Don’t compare yourself to others, realize you are playing your own game, and figure out what you really want to be doing. Your future self will thank you.

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