A short time ago I was helping a CEO recruit a CTO for his company. One important requirement was that the two of them should have a relatively easy working relationship. He wanted to know that their day to day relationship would be fundamentally comfortable, so that when things did get difficult (as they inevitably would from time to time) then conversations would not be exacerbated by any underlying tension.
This seemed like a sensible thing to want, and I started to think about ways one might test for “good day to day relationship”. I’ve previously been able to measure intangible things such as reputation and trust, so there must be an answer here. But my past experience was misleading me, and the CEO had a ready answer—he would take the candidates out for dinner. To me, this was clearly a good idea. It tested for social and communication skills in a natural environment that was likely to be a key part of a growing company with external investors.
By coincidence, a few days later I read an article by Marty Cagan about hiring for another senior role, this time in the Product area. He talks about the need for “chemistry”, and offers the same solution:
Make sure the interview process includes a long dinner with at least the CEO and CTO. Be open and make it personal.
It was reassuring to see the idea validated.
We should be careful about this, though. The need should be appropriate, as should the solution. I once knew a Head of Development who wanted to hire developers he “could go down to the pub with”. A developer is a very different role, and that “requirement” is both unnecessary and unnecessarily discriminatory.
That caveat aside, I like the very elegant solution to a problem that seems full of intangibles.
niksilver.com 
I’m a bit worried this can lead to a bit of people-like-me syndrome, though.
Yes, I think that’s a legitimate worry. I guess you have to be careful how you do it. “Business dinner” may be different to “Dinner followed by night on the town”. Perhaps another safety net is if it’s the last step in a process which scrupulously casts the net to bring in a diverse set of candidates.