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ColumnsLeadership & ManagementSecurity Leadership and ManagementSecurity Education & Training

Leadership & Management

You Asked. Now Ask Again.

Good leadership can mean asking the right questions.

By Michael Gips
Leadership & Management
Image: 9dreamstudio / iStock / Getty Images Plus / Via Getty Images
October 19, 2026

Good leadership often hinges on asking good questions. My journalism and media-training background particularly informs how I approach them.

In mock print interviews, senior executives and experts often begin with canned, clipped, guarded answers. I get the conversation moving, demonstrate that I know the subject, and lower the temperature. Then I return to an earlier question, reframed in light of something the interviewee has said since.

Now the real conversation begins. For the interviewee, the lesson is to know your objectives and not be drawn casually beyond your lane. For the journalist, that is often exactly where the interesting material lies.

The lesson travels beyond journalism. I routinely interview executives about risk appetite, critical assets, security culture, and priorities. Sometimes they think there is a “right” answer. I need a candid one.

In one case, a client was building a global security operations center. I interviewed executives and security leaders about their biggest security priority. Everyone had a different answer: employee safety, supply-chain security, reputation, proprietary information, life safety.

When I asked what the GSOC should do, their answers followed those priorities. One wanted fire and weather monitoring, another shipment tracking and distribution-center cameras. Others focused on access to sensitive areas.

All were legitimate, but staffing and budget required choices. So I posed the second question: What decision do you expect the GSOC to help you make?

Instead of listing things to monitor, executives began talking about identifying emerging threats, getting actionable information to decision-makers, and coordinating response. Their priorities differed, but the underlying need was remarkably similar.

The first question had elicited preferences. The second revealed purpose.

The useful second question depends on what you are trying to uncover. After an incident: “What surprised you?” During a risk assessment: “What are we assuming?” In a briefing: “What haven’t I asked that I should?”

Security leaders should use that power carefully. The goal isn’t to catch someone contradicting an earlier answer or manipulate them into saying something unintended.

A journalist who does that may lose a source. A leader may lose the trust that makes candid answers possible.

The best second questions show that you were listening closely enough to realize the first answer was only part of the story.

KEYWORDS: corporate culture security career security leaders security leadership skills

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Michael Gips is a Principal at Global Insights in Professional Security, LLC. He was previously an executive at ASIS International. Columnist image courtesy of Gips

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