Dave Kline has a long career as an executive and led multiple divisions at Bridgewater Associates and Moody’s Analytics. He now runs a management accelerator where he trains and coaches leaders. His insights on how to navigate promotion, especially at the senior level, stem from his unique mix of experience as both a senior leader and a coach. This essay draws from a conversation we had with Dave, in which he shared his thoughts and insights with the On Deck Journal.

If you’re looking to advance your career as a senior leader at a company, you might think that what’s given you success so far will continue to move you forward.

This is an easy mistake to make. On one hand, at a fundamental level, the way you get promoted as a senior leader is the same as how you got promoted throughout your career.

No matter what level you’re at, getting promoted is typically a function of your ability to create unique value by leveraging your skills, abilities, experiences, and anything else about you that gives you a competitive advantage and lining it up with what the company needs.

If your company’s needs are aligned with what you uniquely do, it’s a recipe for moving up.

On the other hand, things do become more nuanced at a senior level, where you are competing against a higher tier of candidates to be promoted into fewer roles, and where promotion cycles are both less frequent and less predictable.

This guide covers some general principles of career advancement as well as how to move ahead once you do reach the senior levels of a company. For senior leaders, promotion doesn’t happen by accident. It’s about positioning yourself for promotion by carefully executing a good strategy, and making sure you have the skills and experience to succeed when you do land the role.

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Why career advancement is different at the senior level

As mentioned earlier, no matter what level you are at, but especially as a senior leader, to position yourself for promotion you want to try to align your unique ability to create value with what the company needs

There’s a narrow version of that which is as simple as observing that you have marketing skills and that your company needs a CMO — and expecting to be promoted accordingly. However, the more effective executives are typically more creative than this.

Firstly, they’re not necessarily positioning themselves for an executive role that the company needs today; instead, they’re looking to position themselves for an executive role that their company may need in the next 2-5 years. Having that type of lead time is necessary to cross the chasm of getting to the C-level and accumulate the relevant experiences you’ll need to take the next leap (more on this later).

Another of the things that gets harder when you seek a promotion at a more senior level is that there are less spots to fill and the people who are competing for them are increasingly accomplished. 

For example, if you have a company with 500 analysts as an entry-level role, and 25% of analysts are promoted to associates, then you’ll have 100 people who make the first leap to that second rung. But the further up the career ladder you move, the smaller the fraction of people who will make it up to the senior rungs — and you’ll be competing against five, six, or seven people who have made many leaps. In theory, the best of the best.

Because opportunities for promotion at a senior level are fewer and competition is more stiff, the things needed to take the next leap also become increasingly hard to measure, unlike things which matter lower in the leadership ladder such as technical competency which are easier to compare quantitatively. 

At the senior level, moving forward instead rely on qualities like:

• What does your following look like within the company?
• Are you able to galvanize people with your leadership, or do people chafe working under you?
• How well are you able to pull your peers together and foster collaboration? How do you connect other senior leaders?
• Do you generate a lot of creative, unique ideas?

However, there’s no universal formula. What matters is finding that fit between who you are, what unique attributes you bring to the table, and what the company uniquely needs. The stronger that fit, the better positioned you’ll be to be promoted.

Additionally, while it’s not always enough to “just work hard and ask your manager” for advancement no matter what stage of your career you’re at, once you reach the senior level, good effort and being able to ask for what you want become table stakes. 

You typically will not advance to the senior level in the first place unless you were already doing those things — now it’s about differentiating yourself against other people who are also hard-working and willing to ask for promotions. 

Another issue is that once you get to a certain level, there’s no longer anyone left to ask, because you’ve gone from having someone to ask (i.e. the person above you) to the person being asked.

A final big difference is that, at the senior levels, all the things that got you great grades and school and made you stand out as a junior IC or manager start to actually become liabilities, because the type of work you need to do and the skills you need to have become different.

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Mastering The Leadership Ladder

One way to conceptualize the way that skills are valued differently at different levels of seniority is with a “leadership ladder” that breaks down your career into roughly three tiers of what is valued according to your level of seniority.

Tier 1: Early on, you get rewarded for the work that you produce and for things like your technical competency. But as you start to manage and become a leader, you are valued for your ability to work through others.

Tier 2: The skills that increasingly become the most relevant at the mid-level and more senior positions are your ability to prioritize, delegate, judge and hire talent and then coaching and motivating them, etc.

Tier 3: Once you approach the highest levels, it’s about your ability to build alliances within the company, identify strategic partners, raise funding, choose a vision and a path and eliminate the 20 others you shouldn’t go down, etc.

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Notice that what creates value at the third tier — like identifying strategic partnerships — is very different from running an excel model which is what you were evaluated on earlier on.

To get a promotion at a senior level, you have to be able to cultivate and display mastery of the third tier of skills in order to differentiate yourself. Be able to showcase that you’ve developed the properties of an effective executive.

There is a very high correlation between really effective executives and a devoted following or fan base within the company. These are people who would be willing to follow that executive to other divisions within the company, or even to other companies.

If you can develop an almost rabid fanbase within the company, that’s a key differentiator for you at a senior level.

Mastering the third tier is also about cultivating deep, meaningful, trusting relationships within your company — fueling people’s growth such that they feel that they’re going to rise with you as you rise. This can also help differentiate you.

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Crossing the chasm to your next promotion

At a senior level, the distance between you and your desired role can increasingly feel like an uncrossable chasm — often, this happens when you’re looking to move up from the 2nd to the 3rd tier described above.

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Let’s say you’re a VP and your goal is to be promoted to a C-level role. The distance between where you are and your goal might look like a huge gap  — maybe you now have a team of 10, and you look up at the C-levels at your company and they have teams of 1,000.

That chasm can seem very intimidating, and as a result you may feel tempted to resign yourself to where you are.But what you have to realize is that the people in those roles you’re targeting got there from where you are now because at some point they started to build the bridge to cross the chasm, brick by brick.

So instead of being intimidated by the distance, break it down step by step. What experiences do you need to collect to go from here to there? Here are some examples of the “bricks” you may need to lay to cross the chasm:

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• Managing managers - One thing you can see is that, at the C-level, instead of managing 10 individual contributors, you’re going to have to know how to manage managers. Figure out a way that you can start to manage managers at a smaller scale.
• Adding functions - you may notice that at the C-level, there are functions that you don’t have experience with. Look for projects and rotations that expose you to those functions.
• Building relationships - Look to build relationships with the people who are going to be able to influence the decision of whether or not you’re going to be tapped for the role not only today, but three years from now. Cultivate relationships with the three or four people who might decide. You’re going to have to make these bets based on your own best judgment, since you can’t see the future.

What I find when coaching is that when I’m talking to people about crossing a chasm to get a big promotion or job down the road, everything gets twisted up in your head and it’s like you're frozen. It’s often a very powerful exercise to put the individual pieces down on paper, and lay each step needed to cross the chasm out in writing.

When you actually map it out in this way, it can have the effect of making you realize that they’re not as big and daunting and crazy as they seemed to be when they were all swirling around in your head.

What you’ll then realize is that while it might be hard to go from VP to that C-level, and it might take a good amount of time to elapse before you can get there, and it may require you to iterate with trial and error, it’s not an unknowable list and certainly not an undoable list.

Getting into this headspace of focusing on the individual actions you need to take can actually be quite energizing and have a galvanizing effect that you need to get started.

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Making Promotion Inevitable

Once you’ve mapped out your route to the role you’re seeking in terms of the experiences, skills, and relationships you need to add, it’s also a good idea to make sure you are on the same page as the leaders you report to.

First, it’s about setting expectations and creating alignment with your higher-ups where you state a goal as the starting point of self-advocacy, e.g. “I would like to be VP Product in 3 years.”

Then, have a conversation with your boss or the CFO / CEO where you ask what it would take for that to happen. There might be some equivocation in response as they try to avoid promising too much — to put them at ease, you can respond by asking what objective criteria it hypothetically would take to make it very obvious that you would deserve that promotion.

Once you’ve set and aligned on those expectations, you can break it down into the smaller steps it’ll take to fulfill them and keep checking in to see if the expectation has changed at all. If you keep at this for a reasonable period of time, you’ll make it inevitable that either A) they will give you the job or B) you will acquire the qualifications you need to get that job somewhere else.

Average employees do what they’re told. Good employees do better than what they’re told. People looking to rise to the highest ranks will actually tell you, as their boss, what they’re going to do and then do more than what they told you.

If people in this third category know that typically their role expects that they do X, they will come in and say I’m going to do X, and also things Y and Z that you didn’t even know you needed. Proactively defining a high bar and then beating it is a big differentiator.

The idea is therefore to be proactive in laying out your path to advancement, deeply align on what’s expected and then deliver value that’s well above that.

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Common mistakes in career advancement

Why don’t highly qualified people always get promoted as they might feel they deserve?

If you have the qualities we’ve discussed so far — you have a unique brand, you’re impactful, you have a stellar track record, and you’ve mastered the skills at each tier of the leadership ladder — but you’re still not able to advance, it probably comes down to you not being a great self-advocate.

You have to come to terms with the fact that you need to be your own advocate, and that the thought that you “shouldn’t have to” is wishful thinking. People with reasonably strong self-advocacy tend to win the ties. If you’ve been advocating and marketing your impact, you’re more likely to get promoted than someone who has had the same impact but hasn’t taken the step of making other people aware of that impact.

This is one of the most common mistakes people tend to make that holds them back. That’s why creating visibility for yourself was emphasized so heavily earlier in this guide; it’s probably the area to focus on most if you feel you’re in a similar situation.

Another mistake in a similar vein that tends to hold people back is saying “I don’t play politics”. 

I think this attitude is short-sighted. Now, this doesn’t mean that you need to be involved in backdoor dealings or be a backstabbing, deceptive Machiavellian at work. You should be authentic to your brand and competitive advantage that you’ve built over your career. 

But at the same time, you need to be clear-eyed about the power dynamics of your organization. I’ve worked at many different companies — Bridgewater had a culture of radical transparency, Moody’s had a century of tradition. But in every company, there’s inevitably a power structure or hierarchy that exists; and it’s a mistake to pretend that it doesn’t. 

Doing so is the senior executive version of the “I’m sure they’ll recognize my good work” fallacy mentioned earlier. To operate effectively and advance at the senior levels of a company, you need to know:

• How do things get done?
• How do decisions get made?
• Who is really influential in the room?
• Who is influential, despite not having a fancy title? (hint: it’s usually the Chief of Staff to the executives and long-tenured producers).

If you just dismiss all this with the attitude that you “don’t play politics”, you’ll miss all of this opportunity and nuance. It’s not that you’re not playing politics — it’s that you’re misunderstanding the reality of the environment you’re trying to navigate.

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Avoid Over-promotion and overreach

Sometimes, whether moving up internally or taking a job externally, people can actually move up too fast for their own good. If you’re offered an opportunity you might not be ready for, your ego can often get you excited even though it outpaces what you’re actually capable of at that point in your career. 

Moving up the leadership ladder requires you to stop along the way and acquire the new competencies required as you rise to the next tier. If you neglect to do this, it can come back to bite you down the road — if you skip building the skill of prioritizing and delegating work, for example, eventually you’ll get to a place where you will just get stuck or even fail.

According to Harvard Business Review, 60% of US executives (CEOs and board members) fail within 18 months of being promoted or hired.

Keep in mind that these are the most highly vetted and experienced people, with tons of support, coaches, executive assistants, chiefs of staff, you name it. They’re typically people who are 15 - 30 years into their career, and yet they still have worse than a coin flip’s chance of succeeding when they are promoted into an executive role.

The lesson from this should be that managing and leadership at the highest levels is just extremely difficult, even for people who are very good at what they do. The biggest mistake for most people advancing at a senior level is to be in too much of a rush and get ahead of their skis.

The other issue is that the leadership ladder only goes one way — if you get ahead of yourself, it can be very hard for people to ask you to take a step back to the appropriate “rung”. If you make the mistake of overreaching beyond your capabilities, the next step is often that you will be asked to step off.

There’s nothing wrong with being ambitious and taking advantage of opportunities, but it’s important to do so strategically and know your own limits. A career is a marathon, not a sprint. Make sure that each time you advance, you are prepared and you aren’t setting yourself up for failure.

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Creating visibility & owning your own brand

One of the big mistakes people make, especially when they’re a senior leader looking to level up their career, is naively believing that good work will be recognized on its own merit alone. In reality, this doesn’t happen just as often as it does happen.

Just because you’re doing good work doesn’t mean people are seeing it. If you’re one of 10 people working for a manager, for example, you might be doing a great job without anyone truly noticing.In fact, if you’re doing great work, your manager likely had their attention on the people not doing great work and there’s a good chance they didn’t fully notice what you’ve been doing. 

One of the reasons there can feel like there’s such a promotion chasm when you get more senior is that you don’t have enough ownership of your internal brand. Typically, you have to go through the process of owning your own brand and raise visibility for yourself at your company if you want to get ahead.

A framework I use when coaching people to help them raise their visibility at a company is to use the following 3-step framework:

1. Tell them what you’re going to do.
2. Tell them you’re doing it.
3. Tell them when you’ve done it.

Tell them what you’re going to do: If you’re going to take on a big project, or a new role, or bring a new initiative to light, you want to tell the story of:

• What the initiative is going to be.
• What it can change.
• How you’re going to do it.

Tell them you’re doing it: Next, you want to provide frequent, compelling updates of what’s working and what’s not — whether you’re on track or off track, on budget or under budget, etc. This will help set expectations appropriately while also maintaining visibility for the project you’re working on.

Tell them when you did it: When the project is complete, be sure to celebrate what you’ve achieved and recap any surprise wins, like coming in ahead of time or growing faster than expected. 

This framework makes it so that your company is associating you with a victory through the entire process — it’s a framework that can scale to any initiative, whether it be making an excel model or leading an entirely new division of a company.

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Authentic ways to self-advocate

One issue that people often run into when it comes to creating visibility for themselves is overcoming an internal obstacle.

When some people hear the term “self-advocacy”, they often imagine running up and down the hall waving a flag and trying to get everyone’s attention. In fact, there are much more subtle and impactful ways you can self-advocate even if you tend to be introverted or less prone to self-promotion. 

The way to overcome this is to find ways to authentically provide value in ways that also raise your visibility. Here are some ideas you can use to help build visibility by creating an impact instead of being self-promotional:

Teach. For example, if you’re deeply competent at something, you can teach your department or other departments and share your expertise — this helps others level up their skills, helps your company have more engaged and knowledgeable employees, and also helps your brand as you will become someone associated with being highly competent.

Solve a problem. Solving a problem in the company can also shine a light on you. For example, a lot of companies I’ve worked with in the past don’t tend to have particularly good goal-setting or an OKR process. 

Imagine you’re at that company in the middle ranks and you’re striving to become a senior executive — could you be the one who both solves the problem of having a coherent OKR system and in the course of doing that, more people now get visibility into your impact via those OKRs. You’re therefore creating visibility for yourself at two levels — one by showing your ability to create beneficial organizational change, and two by showing your competence in your current role.

Another way to do this is to “go find a piece of pain” — a problem that is shallow in its individual impact, but wide in how many people at the company it impacts (something broken that is annoying to most of the company, but not a critical problem for any one person). This is the type of thing that always tends to get put off or pushed down the road. If you can be the one to make that go away, it can create a lot of positive visibility for you.

I once worked at a place where 50% of the time when I tried to print, it didn’t work. When we hired a CTO, he could have tried to unveil a sweeping change about our approach to AI or something. Instead, his first action was he moved us all onto one platform and made printing work every time. Even though it was not a critical problem, this helped create an association with him at the company that “this is a person who makes problems go away.”

Whatever you choose to do to help raise your visibility, instead of trying to get eyeballs to point at you, go where the eyeballs are already pointed. 

In general, this means it’s a good idea to try to be in one of two places within the company to fast-track your career advancement: either the engine that generates cash or the engine that generates growth. These are the places which tend to have the most attention, and so it’s easier to create visibility for yourself if you’re situated there.

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Focusing on what you can control

If you follow the frameworks offered in this guide — mastering each tier of the leadership ladder before moving up, building a bridge to cross the chasm, and aligning your skills and experiences with what your company will likely need in your target role 2-3 years from now — you’ll be well positioned to advance your career, either by getting your target role at your company or by having the qualifications to get it somewhere else.

But the last thing you need to understand is that at the senior levels, you don’t have complete control over the outcomes, and getting promoted is not as deterministic as it might have been at previous points in your career.

To understand this, think about how the promotion process works from the point of view of the company and the decision-makers who will ultimately have control over the decision. 

At the very top of a big company, the CEO gets hired by the board — which is its own distinct process that only applies to a very narrow set of people and is typically conducted differently by every company.

But a level below that are C-level roles, Directors, VPs, etc. Filling these roles is typically going to be driven by the company demand for the role based on organizational needs, budget realities, growth, etc. and matchmaking with the people available to step up to that role either internally or externally.

Many times, companies will look externally to fill senior roles with “proven” people and weigh this option against pulling up an internal candidate and giving you a chance at the role for the first time.

Ultimately, the decision involves a lot of individual factors of the leaders making the decision, like their risk profile and personal preferences. Sometimes, companies prefer to go external, and in those cases it can be hard to do anything about it on your end.

That said, companies typically see more success promoting people from within because it de-risks a lot of factors about their career aspirations, personal life, culture fit, etc. If you’re comparing an external person with someone who has spent 10 years at your company, you know a lot more about the internal person — good and bad.

Despite this, there’s a tendency to put a halo on outsiders and look at all the amazing things they’ve done, purely because you have less visibility about the unknown risks and negative characteristics,  which can make it an unfair comparison.

So keep this in mind and don’t get discouraged if you’ve done everything in your control and still get passed up. Remember that the experiences and skills you’ve accumulated in your attempt to cross the chasm don’t go away — and even if the path doesn’t lead you to the exact destination you thought it would, you’ve made real progress towards your ultimate target.

Ultimately, rising to the top ranks and becoming an executive means being able to stomach failure and keep trying. It may be helpful to adopt Winston Churchill’s dictum that “success is moving from failure to failure with no loss of enthusiasm”. As previously mentioned, 60% of execs fail.