You might be thinking, “Wait a minute, Claire. I ask this question, ‘How can I help you?’ all the time. How is this possibly a bad question to ask?” Well, it is for several reasons. And trust me, I’m guilty of asking this question as much as you are. Learning how counterproductive this question is surprised me as well.

First off, the question “How can I help you?” is enormously intimidating to an employee. There’s a reason that 9 out of 10 times that you ask it, that the other person says, “Hmm nothing I can think of right now.” It’s because you, as the boss, are putting pressure on the other person to critique your job. You’re giving them no parameters, no direction, as to what kind of feedback or critique you’re looking for… And so your direct report will often think the safest response is no response.

Secondly, asking “How can I help you?” puts a burden on the employee. You’re asking your direct report to do the heavy lifting of figure out how you should be doing your job better as a leader. There are plenty better questions you can ask – questions that, no doubt, require a little more thought ahead of time to come up with. For example instead of asking, “How can I help you?” try asking:

  • What do you find challenging about my management style

  • What aspect of my work do you think I can do a better job?

  • Do you think I’ve been a little micromanaging with how I’ve been following up on projects?

  • Have I not been as cognizant of reasonable timelines, like I should have?

  • Would you like more or less direction from me? Why/why not?

  • What’s a recent situation you wish you handled differently? What would you change?

  • When have you been annoyed, peeved, or bothered by me and something I’ve done?

  • Could I be doing a better job outlining the vision and direction for where we’re headed?

  • Am I giving you enough information to do your job well?

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