“Stories and lessons from an unexpected journey in finance.”

Earlier this week, we talked about the danger of confusing high performance with high potential. How do you actually spot that potential during a busy month?

The answer hides in your one-on-ones.

Most finance one-on-ones are just glorified status updates. We talk about the audit, the variance reports, and the ERP migration. But if you want to build your bench strength, you have to stop using one-on-ones to manage the work and start using them to mine for leadership.

Here are the five questions I use to shift the conversation from a tactical status update to a strategic treasure hunt:

1. “If you had to tear down one process and rebuild it from scratch, what is the very first thing you’d change?”

• What it tests: Double-loop learning. A high performer will tell you how to make the current process 10% faster. A high potential will tell you why the process shouldn’t exist in the first place. You are looking for the courage to challenge assumptions.

2. “Which department outside of Finance do you think has the hardest job right now, and why?”

• What it tests: Enterprise empathy. If they can only see the world through the lens of the GL, they aren’t ready to lead. You want someone who understands that Sales is fighting margin compression or that Supply Chain is battling vendor volatility.

3. “If I told you to permanently drop 20% of your current daily workload to free up capacity, what are you dropping and why?”

• What it tests: Strategic prioritization. Future leaders know the difference between “busy work” and “value creation.” If they think every single spreadsheet they update is a matter of life and death, they lack the altitude to be a CFO.

4. “Tell me about a recent conversation where you had to push back on another department. How did you leave the relationship?”

• What it tests: The “Yes, If…” mindset. Finance is a department of friction. You want to see if they act like a rigid corporate bouncer (“Policy says no”) or a strategic navigator (“We can’t do X, but we can do Y”).

5. “What is a skill you see the leadership team using that you feel you haven’t had the chance to practice yet?”

• What it tests: Self-awareness and ambition. It forces them to look up from the keyboard, observe the executive level, and map their own gaps.

The Takeaway

You don’t need to ask all five in one sitting. Drop one into your next meeting and see where the conversation goes. You might just realize your next great finance leader is already on your payroll.

What is your absolute favorite, go-to question to ask in a one-on-one to get someone thinking strategically?

#TheAccidentalCFO #FinanceLeadership #TalentDevelopment #Mentorship #inersec