In working with my clients, I have had numerous conversations about hiring executives.
Hiring that CEO for your business, or that senior executive for your team is a high-stakes game. Getting it wrong is costly across too many dimensions.
And by the time you have that shortlist of candidates, it is not about qualifications.
It is about fit
It is about culture
It is about style
It is about assessing if that individual will execute
It is about whether you and this executive can drive the business to new levels.

How do you test against that? We can behavioral interview , and assess if past experience translates to your needs. That is critically important.
But at the end of the day, there is that doubt. They might have worked in a big corporation, but can they fit into my business which has many differences? Can they build upon the culture and aspirations you have built?
How do you test that?
Throw aside the notion of the interview. These discussions need to be direct.
Tell them you want to have a conversation about the business, about your priorities. Engage in a conversation of peers and you will understand the perspective the candidate brings.

In no uncertain terms, tell the candidate the three things you like about them and the three things that you are unsure about. Directly. Clearly. Tell them! I am concerned how you will take this organization and business and bring a passion to execute to the table. Tell them you are concerned about how your business is vastly different from the business they have led. Tell them you are concerned about their lack of experience in certain areas.

Whatever it is, the time for probing is over.
It is time for that direct peer-to-peer conversation.
That is when their perspective, their acumen will emerge.
That is how that nagging doubt gets clarified.
Because, after all, this is as much about thought partnership than anything else