Content
Most CS leaders are excellent at reading a room.
The conversations they have about their own career rarely get the same quality of attention.
The questions that matter most get deferred into the slot that never opens. Whether they’re actually growing or just busy. Whether the role they’re in is still pointing in the right direction. Whether they’re being paid what the market would actually pay them. Whether the story they’re telling themselves about why now isn’t the right time is true or just comfortable.
CS leaders are trained to be responsive. To solve problems, keep the business moving, support the team. The quiet, uncomfortable work of sitting with hard questions about their own trajectory doesn’t come with a deadline or a stakeholder asking for an update.
So it waits.
These are not conversations most CS leaders are avoiding on purpose. They’re just never urgent enough to schedule until they are.
Busy and growing are not the same thing. And the years that look full from the outside can quietly be the ones where the least development is happening.
1. Am I growing, or am I just busy?
Busyness is the most convincing distraction from the question of whether you’re actually developing.
CS leaders are almost always busy. The work doesn’t stop, the team needs things, the customers need things, and the pace of a high-growth environment rarely creates natural pauses for reflection. Busy becomes the default. And the question of whether the busy is producing growth gets deferred alongside everything else.
The conversation to have with yourself: what can I do now that I couldn’t do 18 months ago? What have I learned that has genuinely changed how I think about CS leadership? What new territory have I navigated that stretched my capability?
2. Is this role still right for where I’m trying to go?
Most CS leaders stay in roles past the point where the role is still serving their development. The work is familiar, the team is good, the company is stable. Leaving feels disruptive and staying feels responsible.
But there’s a specific moment where a role shifts from building your career to coasting on one you’ve already built. The challenge that used to stretch you has become the work you do on autopilot. The skills that used to be new have become the skills that define you in a box you’re starting to outgrow.
The question isn’t whether you can keep doing this job. You clearly can. The question is whether this job is still building toward the version of your career you actually want.
3. What do I actually want my career to look like in three years?
This is the one most CS leaders can’t answer with any real specificity. And without the answer, every decision is reactive.
A promotion opportunity arrives. Should you take it? Depends on where you’re trying to go. A new company approaches with an interesting offer. Is it the right move? Depends on what you’re building toward. Someone asks you to take on more scope. Does it make sense? Depends on whether that scope is developing you or just adding weight.
Without a clear sense of direction, every opportunity gets evaluated on its own terms rather than against a destination. That leads to a career that accumulates rather than compounds. A series of sensible decisions that somehow don’t add up to the thing you were trying to build.
Take the question seriously. Three years is close enough to be real and far enough to require genuine intention. What do you want to be doing? What kind of company do you want to be in? What does your leadership scope look like? The more specific the answer, the more useful every decision that follows becomes.
4. Am I being paid what I’m actually worth?
This is the one most CS leaders put off the longest.
CS has historically been underpaid relative to the revenue function it protects and generates. Most CS leaders know this in the abstract but haven’t translated it into a concrete question about their own situation. The conversation feels uncomfortable to initiate. They’re not sure how to make the case. The timing never feels quite right.
The cost of not having this conversation compounds quietly over time. Every year the salary conversation doesn’t happen is a year the gap between what you’re earning and what the market would pay you grows a little wider.
The honest conversation to have with yourself first: do you actually know what your market value is right now? Have you looked? Have you had conversations with peers, with recruiters, with people in comparable roles at comparable companies? If the answer is no, that’s where to start. You can’t make a case you haven’t built.
5. What story am I telling myself that’s keeping me stuck?
This is the hardest one. And the most worth having.
Most CS leaders who are stuck are not stuck because of external circumstances. They’re stuck because of an internal narrative that’s shaping every decision they make without being examined.
The story that it’s not the right time yet. That things will change if they just keep delivering. That asking for more feels like complaining. That the promotion should come without them having to advocate for it. That being good at the job is enough.
These stories are not irrational. They’re often built on real experiences and real contexts. But they’re running in the background, quietly closing doors before the decision even gets made.
The conversation is simple and uncomfortable: what story am I telling myself right now that, if I stopped telling it, would open up a move I haven’t been willing to make?
You probably already know the answer.
the pattern
The CS leaders who end up somewhere they didn’t intend rarely got there through one bad decision.
They got there through a long series of decisions made without a clear sense of where they were trying to go. The career conversations they didn’t have with themselves created a vacuum. And other people’s priorities, timelines, and definitions of success filled it.
That’s a recoverable position. But it starts with the conversation.
