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If the Shoe Fits: Tough Questions

by Miki Saxon

A Friday series exploring Startups and the people who make them go. Read all If the Shoe Fits posts here

5726760809_bf0bf0f558_mAsk any recruiter or manager who has been around for awhile and they’ll tell you there is only one guarantee when it comes to talent: supply and demand are always at odds.

The danger is highest for those to whom hiring is newest and founders can be especially vulnerable.

Obviously, founders and others in a startup are excited and high on what they are creating or they wouldn’t be there.

And therein lays the danger.

In the heat of competition from other startups and the excitement of converting the candidate to their vision interviewers forget or avoid asking certain questions.

Worse, if the candidate is super-hot or possesses badly needed skills interviewers often avoid asking anything that might spoil the deal or turn the candidate off.

But it is of little use to hire even extraordinary talent if they don’t stay or bring in someone who will trash the culture and tear the team apart.

Which questions are most often ignored?

The tough questions, which are, by definition, any question to which you don’t want to hear the answer.

Simply stated, tough questions are the ones that bring a negative answer when you want a positive one and vice versa—in effect killing the deal.

Here are some sample tough questions and their potentially deal-killing answers:

  • Q: Does the project turn you on?
    A: Not particularly.
  • Q: Then why are you here?
    A: I heard I could make a lot of money and get a ton of stock options.
  • Q: What do you find attractive about the position?
    A: The perks are awesome.
  • Q: Do you like our location?
    A: Well, it’s about an hour from where I live.
  • Q: How soon after accepting can you start?
    A: I’m in the middle of a project and would have to finish, and I’d like to take a couple of weeks off—say, about three or four months.

Money questions are often a minefield.

  • Q: What kind of compensation package do you want?
    A: Well, I just got a raise, a promotion, and a large stock grant and currently I have six weeks of vacation, and I’d like to improve on that.
  • Q: Our salary range goes to $100,000.
    A: Oh, I’m currently making 95 and have a review due in a couple of weeks.

The important thing to keep in mind about tough questions is that if the response kills the deal or raises serious red flags you are better off to know it sooner rather than later, before you spend time crafting an offer or having to contend with a hire who damages the company.

There are other important benefits from asking though questions.

Bringing potential problems out in the open gives you the opportunity to solve them, but first you have to identify them.

Finally, the discussion itself is valuable.

You learn more about a person’s priorities, ethical structure, style, and personality when discussing difficulties and solving them is the beginning of the bond that is the basis for the most productive relationships.

Image credit: HikingArtist

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