“As your manager, what is the one area where I am going to struggle with you? Where are we going to have trouble?” There is a reason this is the most important question to ask when hiring. The answer is a strong indicator as to why you may be making a hiring mistake.
This question is better than asking someone “What are your weaknesses?” If you ask this question, your potential new hire is likely going to tell you that they wish they were more organized, believing that this a safe answer. You also wish you were more organized than you are, don’t you? They may also make some comment about wishing they were better at their paperwork. Neither of these sounds like offenses for which someone should lose an opportunity to work for you.
The reason to ask about the one area where you are likely to struggle with a prospective employee is that you both get to decide whether you can live with each other.
No Safe Answers
A salesperson I interviewed once answered the question “Where am I going to struggle as your manager,” with the answer, “I hate prospecting. I don’t want to make any cold calls, and I do better when someone else books my appointments for me, and I just show up to meet with the prospective customer.”
I asked him why he didn’t like to prospect, and he gave me an answer that suggested it was beneath him because he was capable of creating far greater value if someone else did it for him. He thought it helped build him up as a value creator.
I didn’t hire him.
If you dig down to the root of any answer that tries to avoid the truth, you will find some issue worth exploring. Time management is a self-discipline issue. So is a lack of organization. Even not turning in expenses suggests a deeper issue, like an inability to follow rules or an indifference to making sure the rest of their team has what it needs.
You and your prospective hire both need to decide whether the worst thing about them is something you can both live with.
But this isn’t a one-sided affair.
When Hiring, You Tell the Truth
You need to tell your prospective hire the worst part about working for you. They need to know before they accept a job offer what it’s going to be like to work with the worst version of you.
If you are not going to spend time training and developing them, they need to know that. If you expect your reports to be in your inbox before they leave on Friday without exception because you are rigid, inflexible, and detail-oriented, they also need to know that. If you expect them to prospect religiously, it is only fair to explain that to your perspective employee before they accept the job.
If you can get to the truth, you can explore how you and your candidate can work through these issues together. You can set expectations, and you can talk about how you will deal with issues that arise. You can talk about the help that you might offer your new hire, and you might ask them how you can make sure they get what they need from you when they need something. Or, you can decide you aren’t going to be a good fit for each other.
Neither you or your new hire need to discover that you have irreconcilable differences after they begin working. Honesty is the best policy for both of you.