Ask Savannah
Navigating promotions, plateaus, offers, and the moments when the obvious next step stops being obvious.
Being noticed and being promotable reward different things — visible individual output gets you seen, while building capability in the people around you is usually what actually clears the next gate. A strong track record of personal wins doesn't automatically demonstrate the second skill, and past a certain level, only the second one is really being evaluated.
Readiness is about capability; comfort is about familiarity, and only the first one is actually required before stepping up. Check whether your judgment holds under bigger, less certain conditions — not whether the role feels natural yet, because that feeling reliably lags behind actual readiness.
Take that seriously rather than dismissing it as a lack of drive — the things that motivated you at thirty aren't guaranteed to be the things that motivate you now, and wanting something different isn't evidence the earlier plan was wrong. Separate what you still value in your current path from what you've simply kept pursuing out of momentum.
Name specifically what you'd be leaving to gain versus what you'd be giving up by staying — vague dissatisfaction rarely resolves into a clear answer, but a concrete accounting of both sides usually does. If you can't articulate the specific gap staying isn't closing, that's worth examining before you act on the feeling alone.
Understand every component separately — cash, equity, timing, vesting, what happens if the company is acquired — rather than evaluating the headline number alone. The mix matters as much as the total, and executives who negotiate well tend to ask about the parts of the package other people don't think to question.
Look at the actual mechanics behind the equity — total shares outstanding, current valuation, what happens on exit — rather than the number of shares or the percentage alone, which tell you almost nothing on their own. Equity is a bet on a specific outcome; know what you're actually betting on before you discount your cash to take it.
Ask what success needs to look like at 90 days, six months, and a year — and confirm your own read against what your manager, peers, and team each think, since those three views often quietly disagree. Listen before you act, and find early wins that signal your actual values rather than just your energy.
Separate the momentum of your current trajectory from the honest criteria that matter to you now, which are often a different list than the one that mattered fifteen years ago. The answer sometimes still points upward, and sometimes points somewhere else entirely — both are legitimate if they're the genuine answer rather than the automatic one.
Separate what the setback actually says about your capability from what it says about fit, timing, or circumstance — the two get conflated constantly, and only one of them is actually informative about what to do next. A setback examined honestly is a specific dataset, not a verdict on your future.
Consider lateral moves toward genuine mastery, roles with more real influence and less formal authority, or a deliberate flattening of ambition in one place to build something new elsewhere. None of these read as traditional progress, and all of them can be a more honest answer to what would actually improve the next chapter.
The technical and functional readiness is usually the easy part to verify; the harder, more decisive question is whether you've built genuine commercial judgment and the ability to develop capability in others, since that's what the seat actually requires. If your value still comes mostly from your own individual output, that gap is worth closing before the title changes.
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