Here are my questions for you:

What good career development looks like 👀

There is no one right answer here that fits everyone. (OP knew this - see above.) My advice is to create a culture where your team tells you what they want out of their careers.

I remember once coaching a CTO who was world-class at mentoring his team through technical challenges as they came up in the company. But he loathed the idea of doing personal 1-1s that centered around “career advancement.” To him, it was never something that he chased after, and I strongly suspect he thought career advancement was a waste of time and much more political than it was related to someone’s actual job performance.

I gave him this same advice: rather than putting the onus on yourself to create the perfect career plan for each of your direct reports, encourage them to do it for themselves.

This is helpful for a multitude of reasons:

1. Your direct reports will spend the time thinking through what they actually want for themselves. 
   This avoids the “one-size-fits-all” approach. The reality is, no one will know what they want more than themselves. Anything you suggest to them will be influenced by your own biases and opinions.

2. It encourages them to be proactive and come to you with their ideas, hopes, and desires. 
   This creates vocal, participating teammates who are less afraid or shy about voicing their thoughts and opinions to you, even as their manager.

3. It’s a lot easier to mentor and manage someone who gives you something to work with, rather than someone who expects you to start from a blank slate and magically come up with career development plans for them.

Management growth vs Individual contributor growth 💡

I’m a firm believer that not everyone should aspire to become a manager. All humans are unique and different. Managerial positions aren’t the right fit for everyone.

Unfortunately, the corporate world has evolved to make us all believe that unless you’re a manager, you’re basically stuck with limited earning potential and have no ability to create more wealth for yourself.

That’s why you end up with people who vie for managerial positions, but who really have no actual desire to work in a managerial role.

The higher up you are in your company hierarchy, the more likely you can influence this one: this is especially true if you are a Chief of Staff or COO. Create two paths of advancement for your most important roles.

For example, if you’re running a software company, there should be two paths of advancement - one for individual contributors (e.g.: senior, staff, or principal engineers), and another for managers (e.g.: software engineering managers, head of engineering, etc.) Both should be comparable in salary potential (both base and equity) to incentivize people to stick to the things they’re actually good at and enjoy.

The most successful companies I’ve seen have paths that look like this for their most mission-critical roles. You can think of the Individual Contributor role sort of like an “industry expert” role. Wouldn’t you want someone, like an AI Researcher, to make top dollar to do the best research they’re capable of…rather than forcing them to manage people if they despite managing people?

Same thing with a tax-focused SaaS company. Your tax expert is probably one of the most mission-critical roles you’ll hire for. Don’t you want that person to be well-compensated, even if they never manage anyone (or their scope of management is quite limited)?

To pay more or not during promotions 🤑

When I hear this question, I think back to a story Reed Hastings shared in his book No Rules Rules.

Netflix’s Director of Engineering, Han, found an exceptional candidate named Devin. Devin possessed a rare skill set that was highly sought after, having recently left a position at Apple.

The salary Devin requested was nearly double that of existing programmers on the team and even exceeded Han’s own salary. But despite the high compensation, Hastings supported hiring Devin, reasoning that no current team members could match Devin’s capabilities, and his contribution would surpass that of multiple average programmers.

This decision underscored Netflix’s commitment to investing in top-tier talent to drive innovation and maintain a competitive edge.

Rather than ask yourself, “How much should I increase this person’s salary by?” Every time they get a promotion, the better question to ask is: How much would I pay a person for this role if I were to hire for it from outside the company? That determines the appropriate salary band. Every role has responsibilities with an expected ROI. You want the salary band to match the perceived ROI accordingly. That’s all that matters - the existing salary is almost a red herring.

The best situation is if you already have someone internally who can do the job, because they have tons of context and therefore will ramp up in their promoted role much faster than if you were to hire externally. It’s also easier to fill in lower levels in the company.

Going back to the promoted person in question - if the salary band means they deserve a raise, then give them the raise. Especially do it if it means you can save your recruiters time and fill the role faster!

Otherwise, the salary can stay as-is, and you’ll have objective reasons as to why there is no raise accompanying the promotion. In this case, by the way, I wouldn’t frame it as a promotion as much as a retitling to match the role better with the teammate’s responsibilities.

Remember: You hopefully operate your company with a high bar of talent density. You don’t run your company as a charity that holds onto low performers - they’re either doing kickass work, or they’re out.

Similarly, your employees are not running a charity either. Don’t expect them to do work for free - especially if they’re world-class at what they do.

When your teammates don’t want promotions 🙅

There are some cases where a teammate is happy exactly where they’re at. They find personal fulfillment in their current roles, and they aren’t interested in the traditional hustle of, “More, more, more!” They find their “more” in their existing role and responsibilities.

This is especially true of many Executive Assistants I know. While many EAs I’ve worked with aspire to grow into Chiefs of Staff or department leads, I know just as many “Career EAs” who want to stay where they’re at because they love their job, the workload, and the flexibility they have.

I also know many software engineers who are happy staying at the Senior level, and never aspire to hit a Staff or Principal level. When I ask why, they shrug and say, “It suits my skillset better. I have new problems to solve every day, and I know that taking on ___ promotion would require me to take on XYZ responsibilities - none of which I’m particularly interested in or even good at.”

The short of it: teammates that don’t want promotions are NOT the same as teammates who are lazy. It’s easy for operators to forget this, especially co-founders. Most people who start and build companies are wildly ambitious when it comes to climbing social ladders, so it boggles their mind that someone wouldn’t want this.

There’s also a common trope that someone refuses promotions only because they’re lazy or unable to achieve the promotion in the first place. This is false, too. Some people find genuine satisfaction right where they’re at. This isn’t inherently problematic.

👉 Here is the most important thing to evaluate: is this person good at their job? Would they pass The Keeper Test? (“If this employee were to leave tomorrow, how hard would you fight to keep them?”) If they are a 5 out of 5 on The Keeper Test in their role, that means they’re excellent at their job. Why should it matter whether they want a promotion or not?

When there is no more room for promotions at your company 💼

I think it’s important for operators to understand what their teammates care about beyond money, and why.

A best reason talented employees join a team is because they get to learn on the job and tackle challenges.

The nice thing for you is, they don’t have to get a promotion to learn on the job and tackle challenges. There’s a never ending number of ways for someone to learn and grow, while staying in their own role.

But what happens when someone has been on your team for many years, and they want a promotion - but the seat they’re best suited for is already taken?

The uncomfortable answer (sorry!): evaluate who is actually better for that job.

Sometimes, the apprentice really does end up being more qualified than the teacher for the job. Your job is to make sure that at any given point, you have the best person for the role in the appropriate position. This is more than just the tangible responsibilities, by the way: this is also the EQ, relationship between the person and the rest of the team, and many other factors. Please take into consideration the holistic picture when making this decision.

If you end up going this path, it will require you to have an honest conversation with the person who is in the more senior position. If they’re self-aware, they may even know that their direct report is better for the job than they are. And perhaps there are other places in the company that they would thrive in - they might be more interested and willing to move laterally in your company.

👉 I once saw this exact situation unfold: there was a Director of a department who was struggling in their role. Simultaneously, this Director’s right-hand operator was a natural fit for the director role.

In the end, the Director admitted they were probably not the best person for the job, and suggested a different place in the company they could go to where they would genuinely thrive. This freed up the director’s operator to step into the director role. Everyone ended up happy and genuinely living in their zones of genius.

Want more operational content?

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About Regina Gerbeaux

Shortly after her role as Chief of Staff, then COO, she opened her own coaching practice, Coaching Founder, and has worked with outrageously talented operators on teams like Delphi AI, dYdX, Astronomer, Fanatics Live, and many more companies backed by funds like Sequoia and Andreessen Horowitz.

Her open-sourced write-ups on Operational Excellence and how to run a scaling company can be found here and her templates can be found here.

She lives in the Pacific Northwest with her partner Lucas and dog Leia, and can be found frequenting 6:00AM Orangetheory classes or hiking trails nearby.