How to Be a Senior Leader
Many people want to advance in their careers. It’s natural to seek career progression and the increased compensation and autonomy that typically come with it (although of course it’s also more than fine to remain in a role that you enjoy for the long term).
But what are companies actually looking for in senior leaders? What skills should you work on, what should you avoid? Some mentors and managers will help to set you up to become a senior leader at your company, but in many situations the question of how to advance is opaque.
This post runs through some of the most important dimensions for being a senior leader that I personally aim for, and that I look for when promoting or hiring senior management. For the purposes of this post, we’ll treat senior management as anyone who is roughly:
VP / “Head of X” at a startup
Director or above at a 500+ person company
Level 6 or above at the most competitive companies (FAANG and equivalent), particularly in management
If you want to get promoted as a manager, or are considering whether to promote someone on your team, check out the points below.
Build a Machine
When you’re the head of a significant team, whether it’s a small team like Legal, a large organization like Engineering for a major product, or an entire department like Sales, you now represent the entirety of an important capability for your company. And as a complete function, you owe the company certain outputs – whether it’s a working codebase, a certain $ amount of pipeline, or validated product wireframes.
What this means: You need to build a machine that repeatably produces the outputs that you owe the company, rather than focusing on producing the outputs themselves through personal heroics or force of will.
For a small example, if you’re a PM like me, you can’t generate the roadmap differently every single quarter based upon the latest cool framework, and then get buy-in by being personally convincing or charming the executive team. You need to come up with a consistent process for roadmapping and buy-in that can be run by a self-sustaining team that you build.
This is one of the most common ways that executives fail to scale as their role or the company grows – they fail to make the transition from thinking in terms of their own work, to thinking about building a machine that allows them to scale beyond themselves in a repeatable way.
There are a few components to turning your department or function into a machine. We’ll run through each, including a litmus test for whether you’re on the right path:
Hire great team builders. Your team needs to be self-scaling and self-replicating.
The litmus test: The leaders on your team should be able to hire new team members who are at least as strong as those that you would have hired yourself.
Structure your team well. Make sure that you have an effective management corps that has a high ratio of doers vs. managers. Minimize dotted line reporting – dotted lines lead to confusing org charts, where people don’t know who their “real” manager is and need to rely on tribal knowledge to get things done.
The litmus test: If you had to replace 20% of your team, you would keep roughly the same org structure.
Hire independent leaders. It can be tempting to hire people who seem like great executors: Always willing to do what you ask of them, and great at following your instructions. Resist this – you want people whom you can trust to operate independently of your guidance.
The litmus test: There should be leaders on your team who could credibly fill in if you quit tomorrow.
In order for a process to be repeatable, your strategy needs to be sufficiently consistent that your team can execute on it for a long time. Among other things, this means setting a consistent path forward and not getting distracted or reacting too much to recent inputs.
The litmus test: In the last 4 quarters, your departmental strategy should not have changed more than once.
Make sure that your team has an understanding of the metrics and goals that will drive the strategy above.
The litmus test: >75% of your department (ideally 100%) can cite the metrics that determine whether your business is successful, and how they’re able to move them.
An overall litmus test for whether you’re accomplishing the task of building a repeatable machine – if the wheels start falling off the bus when you take a 2-week vacation, either because everyone was waiting for you OR because you were the only one who could cut through the tallest roadblocks, you don’t have a repeatable machine.
If you can accomplish all of the above, you’re almost guaranteed to be at least a middle-of-the-road leader.
This is also why many executives are obsessed with hiring and employee retention. They know that building a repeatable machine requires a strong team, and that long tenures are the equivalent of doing regular maintenance to keep things running in top shape.
Being a Leader Means Never Saying “That’s Not My Problem”
When you’re a more junior member of a team, the path below is usually the most direct route to success:
Figure out the scope of what you can control
Drive the best outcomes you can within that scope
Call out the factors that you couldn’t control (“X other team didn’t pull their weight”; “The CEO made us do it”) so that you don’t get blamed if a project fails due to circumstances outside of your scope
When you’re a senior leader you don’t get to throw your hands up and say that there was nothing you could do. Did your project rely on another team who screwed up? Sorry, you still need to figure out how to get it done. Are you an Engineering leader who hates their Product counterpart? Do they hate you? Too bad, you still need to get things done.
There are a few reasons that it’s critical to not give up –
Giving up means “I can’t solve this, so someone else needs to fix it.” When you’re a VP or more senior, typically there is no one else. You’re at a level where there are few people with the skills and experience to fix the problem at hand, and all of them are going to be busy, too.
Giving up inspires learned helplessness, which is highly contagious. If you give up publicly, you’ll soon find your team and others around you doing it too.
Bad executives give up. Good executives know that the cavalry is not coming – you are the cavalry.
An important corollary here –
Being a Leader Means Winning With People You Dislike…
… or people that you don’t respect, or people that you think are rude, or people that you just don’t think are very smart.
In fact, if you excel, occasionally people you don’t like will succeed because of you. Prepare yourself emotionally for that.
As you become more senior in an organization, you should expect to work with people who you don’t like. As the org chart pyramid narrows, your partners become less interchangeable. Are you a Product Marketing Director who doesn’t like their Product counterpart? Sorry, they might be literally the only one at the company who can do their job.
If you don’t like another leader, your team is going to notice and mimic your behavior. This can very quickly turn into an escalatory cycle in which your team doesn’t trust your partner team, and they increasingly don’t trust you. The easiest way to stop this cycle is to never start it.
If you don’t like working with someone at a senior level, the first step is usually to try to get on the same page about your goals and blockers (and understand theirs). Be transparent about what you need but listen a lot. Incompetence and differing priorities can look really similar – and the way that these conversations go can let you know if you need to escalate.
Hunt For Feedback
High-quality, honest feedback becomes much harder to find as you rise through the ranks:
You get less direct upward feedback because people are worried that you can do damage to their careers (this also means that when you get feedback, they’re more likely to really mean it)
You get less indirect upward feedback (ie someone tells your boss where you can improve) because it requires that people go around your back. This typically requires going to an even more senior person to bring critical feedback (and if you’re the CEO, that more senior person may not exist)
You will get less downward feedback because your boss is more busy and your job is to build a repeatable machine independently – see above. Your boss is less likely to check all aspects of your work, and unfortunately somewhat more likely to just fire you if things aren’t working out
If your organization is growing fast, your job literally changes and becomes harder every year. At the same time, the amount of helpful feedback that comes to you naturally diminishes.
What this means - you need to solicit and listen to feedback much more aggressively:
Ask team members that you trust what you can do to help things run more smoothly
Ask them what you can stop doing – an often missed area for improvement
Talk to peers at other companies, and hear how they approach similar situations to you – things that work well for them that you aren’t doing can help you see easy opportunities for improvement. Note that these conversations will not happen if you don’t force them to!
Read a lot, especially from your friendly neighborhood anonymous blog
Be a Professional
And finally – be a professional. Being a professional won’t help you advance in isolation, but it’s one of the fastest ways to lose your title by losing your job. And it is absolutely, 100% one of the checkboxes that executives look at when deciding promotions.
As you move into senior management people will increasingly observe your behavior. You can use this to your advantage by being a great role model, but don’t give anyone an excuse to behave badly just because you did.
Some table stakes behaviors:
Don’t be a jerk or act improperly
Be discrete – be a trusted custodian of the increased number of sensitive secrets that you will hear
Have the company’s best interests at heart
Don’t be confidently incorrect
Don’t lose your temper
This might seem obvious but many people unfortunately don’t follow this advice. When you’re an executive you’ll be held to a higher standard, so avoid this sort of unforced error.
To become (and remain) a senior leader at your company:
Build a machine
Don’t give up, don’t say “that’s not my problem”
Learn how to work with people you don’t like
Hunt for feedback
Be a professional
– The SaaSy Product Manager