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EPISODE 9 October 19, 2026 807

When Your Career Has Stalled

EPISODE NOTES

About this episode

Your career can look successful on paper and still feel completely stuck.

In this episode, Steve explores why capable people get passed over for promotions, including invisible ambition, the competence trap, limited opportunities and genuine readiness gaps. Drawing on his own experience of watching colleagues advance while he remained a senior director, Steve explains why being valued is not always the same as being advanced.

You will learn how to have a more useful career conversation with your manager, assess whether the next opportunity truly exists, create visible evidence that you are ready and decide whether your best move is upward, sideways or somewhere else entirely.

Because “let’s revisit this sometime” is not a career plan. It is where uncomfortable conversations go for a little lie down.

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TRANSCRIPT

Episode transcript

Transcript provided for accessibility and search. Minor transcription errors may remain.

SPEAKER_00 0:00

You're listening to How Work Really Works with Steve. Practical advice to help you communicate better, lead with confidence, and advance your career. There is a strange thing that can happen in a successful career. You are busy. You are respected. People trust you. Your calendar is full, your inbox is thriving, and everyone seems very pleased that you are there. And yet, somehow, you are not actually going anywhere. Your career can look as if it is moving because the engine is running, but a parked car with the engine running is still parked. It is just using more fuel. I'm Steve, and this is how work really works. Today we are talking about what to do when your career has stalled. Not collapsed, not exploded, not ended in a dramatic meeting with human resources and a cardboard box, just stalled. I experienced this quite late in my own career. I was a senior director, doing significant work and carrying a lot of responsibility. Around me, other people with similar responsibilities were moving into vice president roles. Some had been there for less time, some had broader roles than mine, some had narrower ones, but they were moving and I was not. I was upset. Very upset, actually. It felt personal because careers always feel personal when somebody else gets the opportunity you wanted. You can congratulate them sincerely and still spend the drive home having a rather energetic conversation with yourself. Looking back, I think the organization valued me. They knew I was reliable, they trusted the work I did, but I had been in the role for a while, and I probably looked comfortable. I had not made enough noise about what I wanted. I had not clearly signalled that I might leave if I could not progress. In other words, they valued me, but they had also become comfortable keeping me exactly where I was. That is one of the most important distinctions in career management. Being valued is not the same as being advanced. Organizations tend to solve the problems that are visible and urgent. If you are performing well, not complaining, and not going anywhere, you may not look like a problem that needs solving. You look wonderfully stable. And stability is excellent for the organization, even when it is not doing much for your career. This does not mean you should threaten to resign every second Tuesday. It does mean you must make your ambition visible. I had assumed that doing good work would speak for itself. It did speak for itself. Unfortunately, what it said was, Steve is doing an excellent job right where he is. A stalled career can be difficult to recognize because it often looks quite successful from the outside. You may have good performance reviews, increasing workload, and plenty of praise. But ask a different question. What has actually changed? Has your scope grown in a meaningful way? Are you learning? Are you gaining influence? Are you getting closer to the role you want? Or are you simply becoming more efficient at doing the same thing? Being busy is not movement. Being needed is not movement. Even being praised is not necessarily movement. Sometimes the first sign of a stalled career is not failure. It is the uncomfortable realization that everybody is happy with the arrangement except you. Careers stall for several different reasons, and it is important to identify the real one. Otherwise, you can spend a great deal of energy fixing the wrong problem. The first reason is invisible ambition. You want more, but you have never said exactly what more means. Perhaps you have hinted. Perhaps you said you would be open to opportunities. That sounds polite, but it tells your manager almost nothing. Open to what? A bigger team? A more technical role? A promotion? A move overseas? A small vineyard in France? Your manager is not a career clairvoyant. People are not psychic. If you want a particular kind of progress, say it clearly. The second reason is that you are extremely useful where you are. This is the competence trap. You have become the person who knows the systems, calms the customers, rescues the project, and remembers why a decision was made in 2019. Moving you creates a problem, so the organization quietly leaves you in place. It may even reward you with more work. This can feel like progress because your responsibilities expand, but if the authority, recognition, and future opportunity do not expand with them, you may simply be building a more comfortable cage. The third reason is organizational structure. Sometimes you are ready, your manager agrees that you are ready, and there is simply nowhere sensible for you to go. This is particularly common in technical organizations. You cannot keep creating more managers, directors, and vice presidents every time somebody survives three budget cycles. The structure has limits. A very capable person may be stalled because there is no open role above them, not because they are failing. The fourth reason is readiness. This is the one people often do not want to hear. Someone may want the next role, but not yet have the technical depth, judgment, emotional maturity, communication skill, or breadth of experience it requires. Time served is not the same as readiness. Promotion is not a rite of passage that arrives automatically after a certain number of anniversaries. As a manager, I have seen employees ask repeatedly for promotion when the honest answer was that they were not ready. I have also seen excellent people who were absolutely ready but trapped beneath a structure that could not accommodate them. Those situations feel similar to the employee, but they require completely different responses. So ask four separate questions. Am I ready for the role I want? Does that role, or something close to it, actually exist here? Do the people making the decision clearly know that I want it? And is there visible evidence that I can perform at that level? Do not blend those into one vague feeling that you deserve a promotion. Deserving is emotionally understandable, but it is not a useful diagnosis. If you are not ready, build the missing capability. If there is no role, explore a lateral move or another organization. If nobody knows what you want, say it. If the evidence is missing, create it through a stretch assignment, broader exposure, or measurable results. And if the answer from your manager is, let's revisit this sometime, ask when. Sometime is not a date. It is where uncomfortable career conversations go for a little lie down. You need enough honesty to distinguish a temporary delay from a permanent parking space. When I realized I was not getting the title and promotion I wanted, I decided to expand the work I was doing. I pushed my manager for more responsibility. Pushed may be the polite word. Coerced might be closer. My thinking was simple. If the title was not coming, I would create broader scope and make the case harder to ignore. The role became global, supporting what was effectively a six-day, 24-hour operation. I was carrying the responsibilities of a chief information security officer while also doing significant elements of a chief technology officer role. It was unusual, broad, and risky. The risk was not that I would be bored, the risk was that I had taken on so much that I might not be able to handle it all. There were real benefits. I gained respect, I gained influence, control, and autonomy. I should admit that I am a bit of a control freak, so the autonomy was not exactly unwelcome. It also allowed me to keep my technical skills current. That mattered because I did not want to become someone who only managed the work and slowly forgot how the work was actually done. But here is the honest part. It did not transform my career as much as I expected. The additional responsibility made me more valuable. It gave me broader experience, it made the work more interesting, but it did not automatically produce the movement I had imagined. That is the danger of responding to a stalled career by simply doing more. More responsibility is not automatically more progression. Before accepting the next stretch assignment, ask what it is stretching you toward. What new decision will you own? What new audience will see your work? What capability will it prove? What happens if you succeed? Is there a real next step, or are you simply volunteering to carry another heavy object? You do not need a guaranteed promotion before taking on anything extra. Careers do not work with that level of certainty, but you should understand the connection between the additional work and your objective. Then have a direct career conversation with your manager. Not a general discussion about development, a specific one. Say what role or type of responsibility you want. Ask what evidence would be required for others to see you as ready. Ask what gaps your manager sees. Ask what opportunities could give you that evidence, and ask what a realistic timetable looks like. If the answers are specific, you have something to work with. If the answers remain vague after repeated conversations, that is information too. You also need sponsorship, not just encouragement. Encouragement sounds like, you're doing great! Sponsorship sounds like, I have put your name forward and here is what happens next. One feels nice, the other creates movement. And do not dismiss a lateral move. We often imagine a career as a ladder, with every good move pointing upward. In reality, a sideways move can give you a new sponsor, a missing skill, broader credibility, or access to a part of the organization that is growing. Sideways and then up can be much faster than standing still and staring at the ceiling. Finally, decide how long you are prepared to wait. This is not an ultimatum you announce dramatically, it is a decision you make for yourself. If the blocker is likely to change within a time frame that works for you, staying may make sense. If the structure cannot change, the opportunity does not exist, or the promises never become specific, then the responsible career decision may be to move elsewhere. Loyalty can be admirable. Passivity is not the same thing. Alright, let's put it to work. If your career feels stalled, conduct a simple career movement review. Take a sheet of paper and answer six questions honestly. First, what exactly do I want? Do not write growth. Growth is what happens to houseplants. Name the role, scope, experience, income, influence, or type of work you are seeking. Second, does my manager know this clearly? Not vaguely, not because you mentioned it over lunch 18 months ago. Could your manager accurately describe your objective to someone else when you are not in the room? Third, am I actually ready and what evidence is missing? Separate capability from confidence. You may be capable, but not visible. Or you may be confident but not yet capable. Both can be fixed, but they are not fixed in the same way. Ask for specific feedback. What are the two or three things that would prevent someone from selecting you today? Then turn those into observable evidence. Fourth, is there a credible opportunity here? Look beyond reassuring words. Is there a role, a succession plan, planned growth, or a likely opening? If the only plan is that someone above you may eventually retire to a beach, you do not have a career plan. You have a weather forecast. Fifth, what is my deadline? Choose a reasonable point when you will review the facts and make a decision. That might be three months, six months, or a year, depending on the situation. The purpose is not to become impatient. It is to stop an indefinite wait from quietly becoming several years. And sixth, should my next move be upward, sideways, or outward? Upward is the obvious answer, but not always the available one. Sideways may build the missing experience. Outward may be necessary when the organization has no room or no real intention of moving you. Now turn those answers into a 90-day movement plan. During the first 30 days, have the explicit conversation. State the objective. Ask about readiness, evidence, opportunity, and timing. During the next 30 days, act on one meaningful gap, not six vague development goals, one piece of evidence that materially improves your case. During the final 30 days, review what changed. Did the conversation become more specific? Did anyone advocate for you? Did a real opportunity emerge? Are you learning and moving, or did you merely receive another development plan written in disappearing ink? At the end of the 90 days, choose the next action. Continue with a credible plan, pursue a lateral move, or begin looking outside. The point is not to leave at the first disappointment. The point is to stop surrendering your timeline to assumptions. I wish I had articulated my career objectives earlier and more forcefully. I thought doing a good job would naturally lead to the next opportunity. Sometimes it does. Sometimes it simply proves that you are very good at the job the organization already wants you to keep doing. So be clear, be realistic about your readiness. Understand the structure. Set a time frame. And if the route ahead remains blocked, give yourself permission to choose another route. That is it for this episode of How Work Really Works with Steve. If you know someone whose career is idling in the office car park, share this episode with them. And follow the show so you do not miss what is coming next. Until next time, be useful, be honest, and remember being valued does not always mean you are moving forward.