I am leaving my current company to go to something better within my current company's parent organization and will very shortly be tasked with interviewing my replacement. The company is extremely small < 10 employees overall and my replacement will need to be an island unto himself in terms of software and product development, maintenance, and final tier product support.
The past employment history of software developers at this company is abysmal, with every previous software developer (apart from myself) being fired for inability to perform the basic functions of his/her job, or by the unique stress of the job driving them away in months of starting. I admit that the job is "difficult" and had its frustrations and scary moments, but I still count it overall as a positive experience. I picked up a wealth of career advancing experience and was afforded a technical freedom and creativity that your typical corporate job would have never allowed for.
I feel that I know how to spot somebody who is independent minded, a jack of all trades, and eager to learn new things. One thing I am not sure how to test for is the ability to handle the unique stressors that come from dealing with sales people at a small company.
Part of my job would be to participate as the technical guy in sales meetings with current or prospective clients. When current clients were angry or unsatisfied with work or progress then I would internalize this and get stressed. Also when meeting with prospective clients where the sales people pitch a product, as these things often go, the client says something to the effect of, "Yeah your product V is great! We love it! But what we really need is custom development for W, X, Y, Z and integration packages into A, B, etc...". The sales people of course humour and confirm these ridiculous demands before even asking you about level of effort offline, or worse yet they put you on the spot and ask for a rough estimate immediately. Two hours later you are in another sales meetings and even more promises are made so now you are sweating buckets worrying what happens if they both take you up on it, only to realize a week later that both prospects fell through because they were hoping the custom development was free.
Needless to say, dealing with sales can be an emotional rollercoaster and isn't for the faint of heart.
My question is, how can I take the above scenario and somehow translate that into an interview test that accurately judges the candidates ability to deal with a similar stressful situation? Bonus points: How can I do this without being overly cruel or unfair?