Executive Career Upgrades

8,145 followers

5h

Most executives over 50 assume they’re losing interviews because of age.

Sometimes that’s true.

Most of the time, it’s these five signals:

🚩 Calling yourself “old school” Instead: Position yourself as experienced and adaptable. Companies want wisdom, not resistance to change.

🚩 Using examples from 10+ years ago Instead: Lead with recent wins. Your best story should come from the last 2-3 years, not your glory days.

🚩 Saying “I’ve always done it this way” Instead: Show how you’ve evolved. Talk about what you’ve changed, improved, or learned recently.

🚩 Talking more about experience than results Instead: Experience gets attention. Results get offers. Lead with outcomes, metrics, and business impact.

🚩 Acting skeptical of AI Instead: You don’t need to be an AI expert. You do need to show curiosity and a willingness to leverage new tools to improve performance.

Age doesn’t usually eliminate executive candidates.
The signals that make hiring managers think you’re stuck in the past do.

The executives getting hired at 58, 62, and even 65 aren’t pretending to be younger.

They’re proving they’re still relevant.

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Executive Career Upgrades

8,145 followers

9h

Nobody told me this when I started working with senior leaders, but the average executive job search takes 6 to 9 months. And almost nobody plans for that.

I want to talk about this because I think the silence around it causes real damage.

When most people lose a job or decide to make a move, they think in weeks. Maybe a couple of months if they're being realistic. At the individual contributor level, that timeline might work. But at the director level and above, the search process is fundamentally different.

The roles are fewer. The competition is more qualified. The hiring process involves more stakeholders. Companies take longer to make decisions because the cost of a bad senior hire is enormous. Background checks are more extensive. Negotiations are more complex.

Six to nine months is the realistic timeline. Sometimes longer.

And here's why that matters beyond just patience: it affects your financial planning, your mental health, your family, and your decision-making. If you don't know that a 7-month search is normal, you start panicking at month 3. You start taking meetings you shouldn't take. You start considering roles that aren't right. You start negotiating from a place of desperation instead of strength.

The executives who navigate long searches well do a few things: