The Most Powerful Career Question You Can Ask: “Am I at the Top of Your List?”

A mentor once shared with me a question that sparked the most useful career conversation he ever had with a manager. He was a senior engineering manager, aiming for a director role, and he knew he wasn’t the only one. Several other leaders at his level were also positioning themselves for the next step. Instead of waiting for an opportunity to arise, he decided to be proactive and asked his manager:

“If a director role were to open today, would I be at the top of your list to recommend for the role? If not, what skills or experiences would I need to have to get to the top of the list?”

This question is powerful for several reasons:

1. It Signals Your Intent

If it wasn’t already clear to your manager that you’re aiming for the next level, this question makes it unmistakable. Rather than hinting or assuming they know, you’re stating outright that you’re working toward a promotion. Leaders value clarity, and by framing the conversation around a hypothetical scenario, you give your manager the opportunity to think ahead rather than react in the moment.

2. It Removes Emotional Charge

Because it’s hypothetical, there’s no immediate pressure, competition, or disappointment attached. There isn’t an open role—yet—which means your manager doesn’t have to navigate the tension of choosing between multiple candidates or worrying about delivering bad news. Instead, you both can focus on constructive feedback.

3. It Shifts the Conversation to a Clear, Actionable Plan

Many career conversations stay vague—"keep doing what you’re doing” or “you’re on the right track.” But this question forces your manager to evaluate your readiness for the next level and articulate what gaps exist. If you’re not at the top of the list, why not? What specific skills or experiences do you need to build? This gives you a concrete roadmap for what to focus on before your next performance evaluation.

4. It Reveals Whether You Have the Right Champion

If your manager can’t or won’t answer the question meaningfully, that tells you something important. Either they aren’t invested in your growth, or they don’t see a path forward for you. In that case, you may need to find a champion elsewhere in the company—someone who will advocate for you and help position you for leadership. On the other hand, if your manager gives you clear feedback and action items, you’ll know they’re invested in your success.

When to Ask This Question

The best time to ask isn’t during a performance review—it’s in between. Mid-cycle is when you have time to address any skills or experience gaps before your next formal evaluation. This conversation also keeps your goals top of mind for your manager, making it more likely they’ll think of you when opportunities arise.

If you’re serious about career growth, don’t wait for promotions to happen to you. Use this question to take charge of your trajectory and position yourself for success.