Stop Asking How
The clearest sign is what employees ask
Job Search, Promotion, and Career Clarity: The Mid-Career GPS Podcast
Aug 25, 2026 · 22 min · 7 segments
Send us Fan Mail There is a moment in your career when you may still be showing up to meetings, answering emails, and doing your job, but something…
You have become emotionally detached, almost sterile in the sense of things just kind of bump off you and they don't affect you anymore.
And when employees are frustrated, you will see them fight to make things better.
People will cross that bridge when they've stopped growing, when they've been overlooked repeatedly for projects or promotions.
At some point, the message gets really clear for them, which is, I may be valued here, I may be appreciated, but I'm not going to advance.
When there've been broken promises, leadership changes, organizational policies change, there's a lack of transparency.
If you've ever sat in a conference room and in the conference room, you've got these big placards or posters that talk about the mission, the vision, the purpose of the organization.
And I would walk into a conference room like that and I'd go, are we doing any of this today? Is this why we're here? Let's get back to center on this.
If you're thinking about leaving your job, I want you to ask yourself these questions.
Have you clearly communicated what you need to your leadership? Have you had the intentional conversation to get the information you need to make a clear and clean decision about your next steps? Have you advocated for yourself? Have you said words like, I want this? Have you explored alternatives inside the organization to see where there may be a better fit? Sometimes people think they've already crossed the bridge and it's time to leave when actually what they have done is they've just avoided having a difficult conversation.
You have become emotionally detached, almost sterile in the sense of things just kind of bump off you and they don't affect you anymore.
And when employees are frustrated, you will see them fight to make things better.
People will cross that bridge when they've stopped growing, when they've been overlooked repeatedly for projects or promotions.
At some point, the message gets really clear for them, which is, I may be valued here, I may be appreciated, but I'm not going to advance.
When there've been broken promises, leadership changes, organizational policies change, there's a lack of transparency.
If you've ever sat in a conference room and in the conference room, you've got these big placards or posters that talk about the mission, the vision, the purpose of the organization.
And I would walk into a conference room like that and I'd go, are we doing any of this today? Is this why we're here? Let's get back to center on this.
If you're thinking about leaving your job, I want you to ask yourself these questions.
Have you clearly communicated what you need to your leadership? Have you had the intentional conversation to get the information you need to make a clear and clean decision about your next steps? Have you advocated for yourself? Have you said words like, I want this? Have you explored alternatives inside the organization to see where there may be a better fit? Sometimes people think they've already crossed the bridge and it's time to leave when actually what they have done is they've just avoided having a difficult conversation.
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3 of 7
Stop Asking How
The clearest sign is what employees ask
The Ten Names Envelope
One question revealed who was leaving next
When Retention Backfires
Money and guilt rarely repair broken beliefs
+4 more clips · 8 min 35 sec of audio in all
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