Straight Truth: Is a good boss or good upward mobility more important?

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May 15, 2023

“I joined an incredible high growth start-up, with a lot of humble, kind people. We are close to 100m€ in ARR at this point. Coming from 2–3 companies, with toxic but smart managers, I was looking for a kind, compassionate and humble boss. My boss (the CPO) is that person. As the company has grown I have noticed over the past 12 months, that my boss hasn’t grown as fast as the company has. I enjoy working here, there are some interesting projects to work on, but am not sure how much my bosses personal growth, might hinder my own. Luckily, courses like yours and executive coaches exist. I am in my early 30s, a VP, grew large teams — but don’t feel ready yet to just be content with my growth. Should I look for a stronger leader elsewhere, even if I enjoy working here?”

The tradeoff is personal growth versus a good boss.

A stagnant boss can slow or block your own growth. However, the author describes a rapidly growing company. Two of the biggest factors in personal growth are a supportive manager and quick access to opportunities. While it is possible the author might find a new place with a stronger boss and equal growth, there is risk.

In this situation, I would ask:

How can I help my boss grow? What can I do to help them shine so that they keep pace with the company? Partner with them openly!
Can I step out from under my boss to capitalize on the rapid growth myself, while keeping access to the good boss as a peer?
Is the company still growing rapidly? If it is starting to slow, then moving becomes more necessary.

You should not be content with your growth. But before you give up a good boss and a high-growth environment, spend 3 months exploring ways to grow with or around your boss.

You can always move in 3 months — there is no need to rush.

Note. Many people ask me about a systematic way for career advancement. I wrote a guest post in Lenny’s Newsletter detailing The Magic Loop: A framework for rapid career growth. Many have found it useful.

Audience Insights

As will be the case with all posts in this series, I first post my answer, above, on LinkedIn, and then my audience comments. I have consolidated additional ideas worth considering, including:

Be clear on your career objectives and which areas you want to grow in. Generally, when you are part of a high-growth company, there is opportunity to gain domain experience outside of your field and teams welcome hand-raisers to help (there is always more work than time in the day). Once you identify your growth areas, partner with stakeholders in those domains and ask how you can help (e.g. participate in closing a strategic business development deal, aid with M&A due diligence, improve the current customer support process, organize your company’s annual conference or weekly podcast, etc).
Take this a step further and seek out a mentor in a different discipline (e.g. product, customer advocacy, sales, engineering, etc.) to get a broader perspective of the company and make you a more well-rounded leader. For example, if your goal is to get to the C-suite, think about how your responsibilities tie to finance/revenue (you need to think and talk in terms of the CEO and the Board) and go on a tour of duty across different functions to understand how the different departments operate.
Remember: the only person responsible for your career is you. Be proactive and have candid conversations with your boss about your career aspirations. Then, work with your boss to build a plan on how to get there. Your boss cannot help you if they do not know what your goals are.

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Courses To Improve Your Career

I have built courses to help leaders grow. Popular courses include:

Level Up: Breaking Through to Executive: Covers the specific standards by which executives are selected and how to manage your promotion process to show you meet them.
Managing Up Successfully: Gives specific steps to create effective relationships with your boss and senior peers.

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