Is It Time To Leave Your Job?

The Career Escalator, Reverse 9-Box and other tools to help you make this hard decision

Hi there, it’s Adam. I started this newsletter to provide a no-bullshit, guided approach to solving some of the hardest problems for people and companies. That includes Growth, Product, company building and parenting while working. Subscribe and never miss an issue. If you’re a parent or parenting-curious I’ve got a podcast on fatherhood and startups - check out Startup Dad. Questions you’d like to see me answer? Ask them here.

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In this newsletter I was joined by Ravi Mehta. Ravi is a senior product executive and founder with experience leading product organizations for globally recognized brands like Tripadvisor, Facebook, and Tinder. Ravi is a well respected thought leader and his frameworks on product strategy & product leadership have been adopted by thousands of professionals across the industry.

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“What’s the regular, expected struggle associated with change, creating ownership, etc. and what are the signs for when someone should just look for a new company?”

I recently waded into a discussion in a Slack community that was discussing a few “state of product management in 2023” and “outlook for 2024” threads and articles. Specifically this one and this one. 

I responded:

This response resonated with a lot of people there and then eventually led to the question above.

I’ve written a lot about how to choose and onboard to the right company - from finding your own PMF, to reverse interviewing, and your first 90 days to skill building and unlocking career optionality. But I haven’t yet written about the other end of the rainbow… when you need to pack up and head out.

And it got me thinking: why is that and when is the right time to leave?

The first part is simple - these decisions are highly situation-dependent. Sending out a newsletter to tell you “it depends” is the most PM of all PM moves. It didn’t seem right to answer this question without some process or framework to leverage. But also, can you really reduce such an important decision to a simplified framework?

To help with this decision I spoke with my friend and fellow product leader Ravi Mehta (Outpace, Tinder, Facebook, Tripadvisor) who, it turns out, also gets this same question a lot. 

Today, we’re sharing two approaches to figuring out if you should stick with your company or start looking for new opportunities: The Career Escalator and the Reverse 9-Box. Not surprisingly, both approaches are rooted heavily in evaluating your current environment which is supported by another article on career considerations that we both like by Bangaly Kaba (take a look here).

The Career Escalator (Ravi)

Most people think about their career as a ladder — a ladder that they climb, rung-by-rung, entirely on their own. A better metaphor is to think of your career as an “escalator”. Factors outside of your own efforts can help carry you towards your goals or work against you. 

Career development feels much easier when you are working with the system. An escalator helps carry you up, making each step a little easier. On the other hand, career development is much more difficult when outside factors add friction. Imagine walking up an escalator going in the wrong direction. Each step forward is thwarted because the system is working against you. An extraordinary amount of effort is necessary to make progress.

It’s certainly possible to get to the top when circumstances are working against you. But the path will be more challenging than it needs to be. 

That is why my first question to people looking to get ahead is: “Are you on an escalator going up, or an escalator going down?”. This question illuminates the fact that not everything is in your control—in order to make good career decisions, it’s essential to take stock of your current situation.

Which Direction is Your Escalator Going?

When I ask this question, people sometimes have a hard time evaluating how their situation is helping or hindering their career. Ironically, this is especially true when things are going well. It’s human nature. We tend to give ourselves credit when things are going well and focus on all the external obstacles when things are tough. 

Accurately assessing your situation is critical. I’ve coached people who are too eager to leave a good company because they are impatient to level up, only to find that they’ve traded a pretty good situation for a much tougher and riskier new role.

I’ve also coached PMs who have spent years doing good work that has gone unrecognized or unrewarded. This could be due to internal politics or external factors like a hyper-competitive market or lack of funding. In either case, making the right career decision is a matter of evaluating your talents and how they match your situation.

Here are some surefire signs that you're on an escalator helping to propel you in the right direction:

Business is great 

There is no better career accelerant than success—both the success you achieve directly and the success you’re surrounded by. Successful businesses need to hire and expand quickly. This creates an opportunity to take on more scope and a bigger team. It will boost your prospects within the company and enable you to “level up” in your next job. You’ll benefit not just from being associated with a successful company but also from the accomplishments and promotions that were easier to attain at a growing company.

You got that promotion you wanted (or even one you didn’t)

A clear indicator of being on the right career path is receiving promotions effortlessly, often before you even consider advancing to the next level. If promotions arrive more frequently and with less effort than in prior roles, it's a sure sign you're in a great environment.

You love the people around you (especially your boss) 

Relationships are key to both your day-to-day happiness and your long-term career progress. A strong rapport with your manager will make your work more enjoyable and more rewarding. You’ll be able to have candid conversations, give & receive effective feedback, and trust that you, your boss, and your team are working towards the same goals.

You get the recognition you deserve (and then some) 

Do you feel recognized and appreciated when you do good work? Recognition can take the form of good performance reviews, praise for your work from your boss and others, positive feedback, opportunities to work on challenging and sought-after projects, or even a simple “thank you”. Well-deserved recognition is a clear sign that you are in an environment that values your talents and your efforts.  

You feel a sense of “flow” at work

The theory of flow, popularized by psychologist Mihály Csíkszentmihályi, describes a mental state of deep immersion characterized by a feeling of energized focus, full involvement, and enjoyment. Flow occurs when individuals are completely absorbed in what they are doing, leading to a loss of their sense of time and self-consciousness.

This state is typically achieved when a person's skill level perfectly matches the challenge of the task, creating a harmonious balance between the demands of the activity and the individual's ability to perform it. Flow is often associated with peak performance and personal fulfillment, and is considered a key component in both personal and professional development.

Do you often feel a sense of flow? If so, you’re likely in a role tailor-made for your strengths and talents. Want to learn more about flow? Watch Mihaly’s TED Talk, “Flow, the secret of happiness” or read his book “Flow, The Psychology of Optimal Experience.”

These are all signs that your environment is helping to move your career forward. What does the opposite look like?

Your sense of flow is missing 

Flow is achieved when people do work at the ideal level of challenge: a) not so easy that they’re bored and b) not so hard that they’re overly stressed. Are you bored or stressed most of the time? In this case, it’s worth assessing whether you’re under-challenged or over-challenged in your current role.

The promotion you want seems out of reach

Two things can happen here: 1) you feel you deserve a promotion, but still haven’t received it or 2) you’re unable to understand what is needed to rise to the next level. As a first step, it’s helpful to work with your manager to make your career aspirations clear and set expectations for what it will take to get that promotion. If you’ve made your best efforts and still can’t see that promotion on the horizon, it may be worth seeking out a role where you are better set up for success.

The relationship with your manager feels strained

It’s extremely difficult to make career progress without a good manager relationship. Signs that the relationship is strained include 1) a lack of feedback, 2) little recognition for good work, 3) no “benefit of the doubt”, and 4) criticism that feels unfair or unwarranted. Open, honest communication is necessary to improve this relationship. Ideally, you should be able to express your concerns, seek candid feedback, and provide feedback to your manager about what is and isn’t working for you. However, if these efforts fail and the relationship remains strained, it may be worth seeking out a role where you can have a strong, honest, and mutually beneficial relationship with your manager.

What can be done if your career is headed in the wrong direction?

You’re already ahead of the game by understanding the relationship between your work and your environment, and by recognizing that your situation is making it harder to achieve your career goals. The next step is to take stock of the headwinds and tailwinds that you’re facing. This can help you appreciate the good things about your current role and recognize challenges that you may be able to overcome.

Get clear and actionable feedback from your manager and those around you 

This is the single most important factor in you getting what you want from a career perspective. If you don't know what your manager is looking for in order to promote you to the next level then you're not going to be able to provide and demonstrate it. A good way to make sure you are on the same page is working with your manager to put together a document that you both agree on.

Within it define very clearly 1) the specific behaviors that your manager is looking for you to demonstrate and 2) the specific goals that your manager is looking for you to accomplish in order for you to show that you're ready for the next level in your organization. In addition, it’s helpful to agree on a specific time when you can check in on the plan – usually between 30 and 90 days.

Put in your very best effort to achieve your goals once defined  

After you and your manager have agreed on a plan, it is in your hands to put in the effort and show them what you can do. Once you feel you’ve achieved what was on the plan, it’s time to have a candid discussion with your manager. You can start by saying, "Here's what we agreed for me to accomplish, and I believe that I've done that. Do you agree?" 

Ideally, both you and your manager will see eye-to-eye and agree that you’ve made significant progress on the plan. This is the perfect entry point to discuss the next step in your career.

If your manager doesn’t feel that you’ve made progress, then you can ask for candid and specific feedback. However, it’s also worth asking yourself whether you are fighting an uphill battle. It’s okay to start looking elsewhere to achieve the progress you want and deserve.

When is it time to refocus your energy by moving to a different position within the organization or exploring other opportunities?

If you've acted on all the feedback that you've been given, honestly believe that you've achieved the goals that were set out for you, and the promotion and the recognition you desire has not come, then take a step back. Are you in the right environment to foster your career growth?

There can be many reasons why your career has stalled. Perhaps your manager has different expectations—expectations they may not have clearly articulated to you. There may be factors outside your manager’s control. This past year has been challenging. Many companies have held back on promotions as part of layoffs, hiring freezes, and restructuring.

Your career development may be out of your hands. In fact, it may be outside your manager’s hands as well. The system may be working against you, and you may not be able to change that. Coming to that conclusion can feel daunting, but it’s not necessarily a bad thing.

That situation has happened to all of us—remember, even Steve Jobs and Sam Altman once got fired.  The fact that you're recognizing the situation means that you can deal with it. You can focus your energy where it matters. You can change your circumstances and set your career up for success.

When a lateral move is a step forward

Often, people seek job opportunities that represent a step up, either in terms of higher pay, elevated titles, or increased responsibilities. However, it's crucial to consider the broader picture, especially when circumstances are working against you.

In certain situations, a lateral move can be immensely beneficial. It can put you in a new context that shines a better light on the work that you're doing. A new role can be re-energizing. 

Careers are not a straight line of continuous progress – everyone has launching pads and setbacks. If you’re on an escalator going the wrong way, hop off and find a better path.

“The obstacle in the path becomes the path. Never forget, within every obstacle is an opportunity to improve our condition.” – Ryan Holiday from The Obstacle is The Way

The Reverse 9-Box (Adam)

It is possible to score your likelihood of success in a role and at a company. In performance evaluation the concept of the 9-box is a system for scoring employees across two dimensions: performance and potential. This system is for the employer and used by managers and executives.

It looks something like this:

On the X-axis you have “Performance” which is based on an employee’s current performance—are they below, meeting, or exceeding expectations. On the Y-axis you have “Potential” which is an employee’s potential to grow into a more senior, leadership position. 

This 9-box is used to ensure consistent scoring and treatment of employees across each of the 9 combinations of performance and potential that they could receive. It also acts as a form of succession planning—employees in the upper-right quadrants should be identified as on track for promotion; those in the lower-left should (probably) be shown the door.

Now, let’s flip this on its head and as an employee and use it to evaluate your employer (company). Instead of performance, think of it as the skills you currently possess to do the job well. Instead of individual potential, think about it as environmental potential. This is the potential opportunity for you to be successful within the current environment you operate (your team, company, manager, etc.).

If you’re in a high potential environment you’d be on the escalator going up. If you’re in a low potential environment you’re (unfortunately) headed down.

Signs of a high potential environment:

• A growing company

• Limited politics and infighting

• Supportive managers who provide constructive, clear feedback leveraging a competency model (growth or product)

• An aligned philosophy on how your department/function/role should operate

Signs of a low potential environment:

• Stagnating company growth

• Misalignment on how your department/function/role should operate (you want an empowered product team; the organization and leadership wants a feature factory)

• Managers who don’t provide actionable, clear feedback 

• Tons of politics and infighting

• Rewarding motion over progress

As with the traditional 9-box, the nuances in the reverse 9-box are around the edges. Specifically the upper left (low skills / high potential environment) and lower right (high skills / low potential environment). This is where the decision to stay or go is quite challenging.

In the lower-right box, if you decide to stay at the company then you’ll have to leverage all of your skills to try to change the environment. And depending on how pervasive the environmental challenges are (team vs. organization vs. company), how large the company is and your level of seniority this can range from very difficult to nearly impossible.

As Charlie Munger once said, 

“I would regard it as a sentence to hell if they gave me some company with a million employees and told me to change the culture. I mean it’s hard to change the culture in a restaurant.”

It’s also up to you as to which challenges you want to pursue in your career—do you want to run up the down escalator, even if you’re the fastest and could make it to the top? Or would you be better off working on growth, product, or design challenges rather than environmental ones?

In the upper-left box you’ll have all the support in the world coming from your environment, but your skill gaps may be so significant that you’re actually pursuing a role you’re not well-suited for. As Ravi mentioned above it might not be team or company transition alone that gives you the best long-term options.

Final Thoughts

Managing your career is one of the toughest things you’ll do and you don’t get that many chances to do it. If you find yourself asking the question that kicked off this article:

“What’s the regular, expected struggle associated with change, creating ownership, etc. and what are the signs for when someone should just look for a new company?”

Start by asking yourself “Am I on an escalator going up, or going down?” 

If you’re wondering if it’s time to look for a new company there’s a good chance you’re on the down escalator. Plot your place on the Reverse 9-Box to help you think through it. If you don’t have the skills to be successful, are you in an environment where you can get them? If you do, are you in an environment that is ready to take advantage of them?

Remember that some struggle is necessary and the job isn’t supposed to be easy. But an environment with limited potential means you’ll be struggling in the wrong areas. So find that place where you can be challenged intellectually, not endlessly frustrated with the environment and get yourself back on that escalator heading up.