"Ready" is a feeling in your boss's head. Here's how to put it there.

The usual guidance says to get prepared first. Pick up the skills the next position calls for, enroll in the course, fill the holes in your résumé, and once you can truthfully say you measure up, speak up. Earn it, then ask. Plenty of us in the Baltimore area were taught exactly that, and it has the merit of being sincere effort.

Yet "ready" is not something objective about you. It is an image sitting in your manager's mind, and the promotion tends to land with whoever is already inside that image, whether or not they are the most qualified person in the room.

First. Readiness gets judged by resemblance, not by a checklist

When a leadership group in a Baltimore firm, a Columbia nonprofit or a Towson agency talks about who could move up, almost nobody opens a competency spreadsheet. They picture the person in the seat. Can they see her leading the all-hands meeting, handling the upset client, presenting to the board? If yes, she is ready. If not, she just needs "a bit more seasoning," which describes the audience's imagination rather than her track record. McKinsey and LeanIn's Women in the Workplace 2025 report found that women leaders are twice as likely to be mistaken for someone more junior. A room that takes you for junior is a room that struggles to picture you in the senior role.

Second. The same list reads differently depending on who is reading it

Tara Mohr's survey, published in Harvard Business Review, found that women often pass on roles they feel underqualified for largely because they treat posted requirements as hard rules. Men tend to read the identical list as a wish list. So a woman waits until she satisfies every line, while a man who meets six of ten applies, gets pictured in the job, and wins it. She was already as qualified as she needed to be at the moment she decided she was not ready.

Third. The ambition gap is not what it seems

That same McKinsey and LeanIn research found that 80% of women want a promotion, compared with 86% of men, and that the difference disappears when support is equal. Women are not less ambitious. Women in Dundalk, Essex and Pikesville simply receive fewer chances to be observed doing the next level of work before the title arrives, and it is that observation that gradually assembles the picture decision-makers carry.

Where the old advice still holds

In Catonsville and Essex, skills still carry real weight when promotions are decided. A promotion into a job you cannot yet do is a glass cliff with a friendlier announcement. Russell Reynolds data shows women CEOs serve an average of 5.2 years in the post, compared with 8.1 years for men. That is a small sample, but a telling one, and part of the story is women being set up poorly from the start. So prepare, but do not wait to be noticed until your preparation is finished.

A better path forward

Get yourself into the picture before the role opens. Run the meeting your manager normally leads when she is away. Present to her boss once a quarter on something that actually matters to the business. After that, state the idea plainly so it becomes concrete for others: "I want the VP role when it opens." What would you need to see from me between now and then?" The answer becomes your real checklist, and it is usually shorter than the one you drew up on your own. Each month, finish one tangible piece of that path while the people who will be present when the decision is made, whether in Ellicott City, Randallstown or Reisterstown, can see it happen.

When leaders talk about the next VP in your organization, is your name a clear picture or just a maybe?