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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?

  • @enderland The position I accepted is a transfer into my parent organization, so my new boss already promised the CEO my time for interviewing and training a new guy – maple_shaft Apr 16 '13 at 19:51
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    All this sounds more like something you should mention in your exit interview and not when interviewing your replacement... – yannis Apr 16 '13 at 19:54
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    For the sake of clarification, it basically sounds to me like you want to know how the person operates in/reacts to/works within an environment in which there are no buffers between the dev and the people in the field (a zone in which buffers are almost always a good thing). Is that right? – jcmeloni Apr 16 '13 at 20:00
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    Removed [software-industry], don't see anything industry specific in the question, so let's not limit it to industry specific answers. – yannis Apr 16 '13 at 20:01
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    Maple shaft, you have to be honest with yourself: interviewing your replacement is never completely bias-free. Subconsciously, one wants to demonstrate his/her superiority; if you are forced to interview your replacement, please bear that in mind and check your motives frequently. – Deer Hunter Apr 16 '13 at 20:44
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I'm smiling because I can picture the person who could very much enjoy this but you're right that it's nearly impossible to describe. Here's some thoughts:

Look for previous experience

This is actually not an entirely unusual job - folks who have worked as consultants, hardcore contractors, or as sales engineers are used to this kind of chaos. Anyone who says "supported sales" on their resume is at least somewhat aware of this type of grind.

Be aware when you screen resumes that folks that worked very much in a little dark hole like R&D, big development teams, and large corporations far, far away from customers - are not going to be the best candidates for this element of the job. They may be unique outliers who have untapped potential, but realize that in the time-management department, they should not be your first round of interviews.

Look for personal style, work habits, preferences

Ask them to describe an ideal job. Ask them to describe an ideal day. Ask them how they'd handle situations that you have handled. Ask for personal preferences. Anyone who says:

  • I love planning things out, I thrive on order and planning
  • I hate shooting from the hip, I cannot thrive if I can't consider something fully

Also - look for good/bad experiences. While a person won't ever say "I really hate annoying sales people who lie and make stuff up" - a person will talk about a story where the sales person exaggerated, and they had to deal with the repercussions.

People who haven't worked near sales are going to be something of an unknown... it's harder to tell, but you need someone personable, who likes talking and "what if" conversations, but who can buckle down and get things done - a difficult mix. Many tech folks who don't work near sales will talk about their love for the job in terms of getting to work with similarly smart, knowledgeable people - that's a bit different than the role you're filling and you may want to have care here.

Go right to it - scenarios and descriptions

"We have a challenging role to fill. You'll be going on site with sales staff, talking to potential clients, and dealing with very uncertain project estimates - how will you handle that? Can you give me some examples of similar work?" Is a fine question.

Also the "what if" game:

  • What if you're in a meeting with a client and the salesperson quotes a number that sounds completely impossible?
  • What if you're in a meeting and all the client can do is complain about the current project?

Cruelty

Be as clear as you can. Don't load the language ("you'll be dealing with insane sales people, unreasonable customers and an estimating process that makes a Ouija board look accurate... does that sound like fun?") But do be clear on the challenges and what will be required. Let the candidate try to convincingly rise to the occasion.

Not only does it put the issue out there and give them a way to answer your concerns, but it makes them aware of the actual role. There's nothing worse than coming into a role you find yourself totally unsuited for, and you may find that some candidates self select out - but at least you'll get people who are really up for it.

The gut is a great thing - realize that you may very well have gut instinct on someone. As the person who can do the job, there may be a feeling of "like me in just the right way" that tells you exactly who is right for it. That's not wrong. There's some pretty good research saying that these instincts can be good - particularly if your logical brain can explain some of "why". But be aware of the counter-force - the "like me" can some times be for superficial reasons, so do question your instincts enough to know that the right instinct is engaged.

It is not "unfair" or "cruel" to say that a smart person won't do well in a certain job - picking the wrong person is more unfair and cruel than turning down a good one.

  • This is an excellent answer and more than I was hoping for. Thank you. You have given me a lot to think about! – maple_shaft Apr 17 '13 at 0:00
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    +1 for "not an entirely unusual job" - this sounds par for the course for any senior tech person in an agency environment, for a start. – Carson63000 Apr 17 '13 at 12:49
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I ask people about working with non-programmers and the funny thing is that the ones giving the "wrong" answers - answers that make them a bad fit for my company - are clearly positive the whole time that they are giving a fantastic answer. You can practically hear "Nailed it!" echoing across their forehead as they finish the answer.

If you ask, "our environment is like this, is that good for you?" some people will say yes because they want the job. If you ask "do you prefer this or that environment?" some people will say "they both have their advantages" etc. You need to ask a really open ended question. Some that have worked for me:

  • tell me about working with non technical people. What roles do you work with a lot? What roles would you like to be insulated from?
  • where do requirements and requests usually come from in your company? Do you think that's the best way to do it?
  • do you estimate tasks before you do them in your current role? What tools do you use for that? How would you change that process if you could?
  • tell me about a time someone asked for an unrealistic schedule and what happened
  • tell me about a time you were asked to start a task without proper requirements and what happened

Often you will get someone who very proudly tells you about their ultra rigid waterfall way of thinking complete with escalating to HR, or someone who delights in telling the time they prevented a release that had been promised, or elaborate hypothetical explorations of what they would do that are the opposite of what you know would be right in your firm.

If you're lucky, someone will "light up" telling you about a scenario that's very much like one you've faced recently, and will describe doing something that would be right in your firm. Then you know you've found a good fit. If you're not sure, you could actually just tell them a recent story, and ask what they would do next. If they say they would write a memo to the CEO explaining why the customer couldn't have what sales just promised, you know you haven't found the right person yet.

  • These are all great suggestions, but I could never relate to giving an answer on an interview that they don't want to hear. I am pretty good at reading an interviewer and figuring out what answer it is they are looking for, regardless if I feel it is the right answer or if I would be a terrible fit. Maybe I am just giving the candidates too much credit, that most of them will shoot themselves in the foot and make my job incredibly easy. – maple_shaft Apr 17 '13 at 12:53
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    guessing the right answer is easier for "can you?" "have you?" questions and harder for "tell me about a time" questions. I have received many cheerful and happy WRONG answers from people who are sure they just told me exactly what I wanted to hear – Kate Gregory Apr 17 '13 at 12:56
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    @maple_shaft - your ability to read people is probably a key indicator for why you did well in this position, but many technologists do not posses it. Maybe the person who can bullshit you into thinking they love being criticised by a customer is the one you should hire? – user8365 Apr 18 '13 at 16:21
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    @JeffO You bring up a good point! Such an excellent BS artist would get along well with the sales team ;-) – maple_shaft Apr 18 '13 at 16:42
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My suggestion would be to consider the maturity of the person you're interviewing. Have they had to handle giving estimates quickly in the past? Have they had to juggle schedules and be their own project manager in addition to handling development tasks?

The key here is to get an idea of whether or not someone has the battle scars and what do they take from those days as ways to handle this challenge within IT. I'd be tempted to look for stories from the person's past combined with what adjustments would they make in the future to prevent similar situations in the future. Some people would enjoy meeting with clients and seeing what features are being asked to be built while others may find this overwhelming.

As for doing this in a fair and humane manner, the key here is to give the person the opportunity to tell a story or two from their past and then tweak them to come out a bit of a hero. In a sense, one could see this as setting up the opportunity for one to play hero by knowing of some of the pitfalls and avoiding them so that the project is delivered safely and not jeopardized. If the person shines in discussing the changes, that is key as in a way you want someone that will make adjustments and fine tune a process rather than take the way things are done and stick to it, never deviating from the script.

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