Asking Questions That Create Untouchable Distance

Interviews are won or lost on differentiation. At this level, everyone is qualified - what matters is positioning yourself as the only choice. I have seen more exceptionally well-qualified executives than I can count come away without an offer because they didn't do enough to be the outlier.

How do you do this? By asking the right questions.

Strategic, well-timed questions reveal the company’s true priorities and uncover challenges that you would have otherwise never known about. Even more importantly, they provide you with the intel needed to tailor your responses, guiding the conversation toward why you’re uniquely positioned to solve their problems.

Done right, this helps you create significant distance between yourself and your competition.

Your goal is simple: make it crystal clear that hiring anyone else isn’t an option.

Start With “Why Now? Why Me?”

One of the most effective ways to establish yourself as the only choice is to set the tone right at the beginning of the interview.

Think like a consultant: before diving into solutions, understand the problem.

Example Opening:

"Before we get started, if I may, I’d like to ask: Why now, and why me? What’s happening in the business that makes it the right time for this hire, and what interested you in my profile?"

This single question is powerful for several reasons:

1. It positions you as a strategic partner. You’re immediately signalling that your focus is on understanding their challenges, rather than just waiting to be asked questions.
2. It extracts critical insights about their pain points, priorities and expectations, giving you the context you need to tailor your responses during the interview.
3. It forces them to verbalize why you’re sitting in front of them, reinforcing their own perception of you as the right candidate.

This is how you start creating distance.

Understand the Playing Field: Why Hire At All?

Every executive role exists for a reason, and uncovering that reason is critical to establishing your value.

Ask:

"What happens if this role isn’t filled soon? What challenges or opportunities are driving the need for this hire?"

This question gets the company to articulate the stakes, which serves two purposes. First, it reveals the urgency and importance of the role, giving you insight into how to position yourself as indispensable. Second, it shifts the conversation from “Why you?” to “How quickly can we get you on board?”

If there's urgency - a looming deadline, a competitive threat or an ambitious growth target - you now have the ammunition to emphasize your ability to deliver swift, decisive impact.

Have You Considered Other Solutions?

Conventional wisdom says you should avoid mentioning alternatives. Strategic thinkers know better.

It might sound counterintuitive, but it works because it puts the hiring team in a position where they must rationalize their decision to make this hire, and by extension, their decision to consider you specifically.

Ask:

"Have you considered other solutions, like using consultants, or restructuring the existing team instead of hiring for this role?"

By discussing alternatives, you:

• Force the interviewer to articulate why they need a senior hire.
• Position yourself as someone who thinks about the company’s best interests, not just your own.
• Proactively overcome objections that might arise later in the process.
• Get valuable intel that you can use later.

If there are other options, you now know which angles you need to work to get an edge.

Sizing Up the Competition

In any hiring process, there’s a pool of candidates with overlapping qualifications.

How many times have you lost out to another candidate when you were 'perfect' for the role?

Someone had an unknown edge in an aspect that mattered to the company. You need to understand what the company values most from the hire they’re looking to make. 

Ask:

"What has stood out to you in the other candidates you're considering - is anything missing? I'm just trying to get a good sense of what's really valuable to you."

This does two things:

1. It gives you insight into what the company values most. If they admire another candidate’s technical expertise, you can add more weight to counter that. If they mention a missing skill, you can position yourself as the solution.
2. It signals confidence. By openly discussing the competition, you demonstrate that you’re focused on understanding the company’s needs, not dodging comparisons.

The Value of Being Miles Ahead

When everyone is well-qualified, the margin for differentiation is slim. Being slightly better isn't enough to close the deal. You need to ensure there is no credible alternative.

Strategic questioning achieves precisely this. By uncovering priorities, exposing pain points, openly discussing alternatives and their shortcomings and aligning your responses to their goals, you ensure the decision-makers see you as the only viable option.

When you do this right, the outcome should feel inevitable.