Ask This 1 Essential Question Now to Save a Ton of Time Later

“I can see that you worked hard on this report,” Janice, the CEO, told Fred, her head of HR, after sitting through the 45-minute, 33-page PowerPoint presentation about his plans for a talent review process, “but it’s not what I am looking for.”

Fred was clearly disappointed. He spent weeks on the report.

“What are you looking for?” Fred asked.

Great question, wrong timing.

How often have you put your heart and soul into something — a sales pitch, a presentation, a letter, a conversation — only to find that it misses the mark?

I see it all the time and most of the time it can be avoided by asking Fred’s question on the front end.

If someone requests a piece of work, make sure you understand their expectations in specific detail. Here are some questions you can ask:

  • What specifically are you looking for?
  • What do you plan to do with it?
  • What decisions are you hoping it will help you make?
  • Do you want a one-pager or a more exhaustive report?

If you don’t want to ask the questions — maybe you already have an idea in mind — then articulate your plan and check for alignment. I never submit a proposal to a client without telling them upfront how I plan to approach it (“I plan to send you a brief, 2-3 page letter, outlining the five steps we’ve discussed along with pricing and timing — does that work for you?”)

Maybe you think you should know and don’t want expose your ignorance? That’s a risky bet. Fred may have done a thousand talent reviews in the past, but if he isn’t clear on Janice’s expectations, he’s just as likely to get it wrong as someone who has never done one before. It’s not about ignorance, it’s about meeting someone’s expectations.

And if you are Janice in this situation, be as clear and specific as possible. Answer those questions above without being asked.

So what was Janice looking for? A set of questions that could help her — and her executive team — assess the talent gaps in their teams. She wanted 1 page and a robust conversation, not 33 pages and a monologue.

But shouldn’t you give people the freedom to surprise you with their approach? Isn’t that kind of detail micromanaging, you might wonder?


After the fact criticism without upfront clarity is micromanaging. Being clear about what you want — that’s just smart, considerate, reliable leadership.

Originally posted on


  1. I liked the article. First the Question. Ask This 1 Essential Question NOW to Save a Ton of Time Later?
    Instead of Ask This 1 Essential Question: How to Save a Ton of Time Later?
    The fact is that Janice is the CEO and Fred is her Head HR. Yes I know the feeling of putting your heart and soul into any job, no matter what that job may be. (I had a boss tell me once. No matter what you are given to do. No matter how many little menial jobs that supervisors don’t want to do because they think it is beneath them, so they come and ask for you to do it on a regular basis. Just remember this, everything you learn no one can take that away from you. One day the Head Boss will ask one of the Supervisors where is that information and they will have to come to you.) She was right.
    In this case, I think both learned something. Janice delegated this project to Fred probably knowing he would do a good job. But from reading his suggestion to her, then her disagreeing with that in addition to the project he turned in. It seems that maybe Janice didn’t know exactly what she wanted…at first. So she wasn’t clear about it with Fred. When Fred realized it wasn’t what she wanted then made the suggestion he thought would be the best conclusion, then that wasn’t what she wanted either. I think that’s when Janice realized what it was she did want. The fact is it was a one page if that, a couple of lines that could get her meeting with her team going. All of this could have saved a lot of time if Janice had sat down and thought it out. Thought about what it was she wanted for her team. How she wanted the next meeting to go in order to fill in the gaps. For lack of a better term.
    In the end they had to sit down, Janice had to spend 45 min. reading a report she didn’t agree with. Then explain to Fred what she wanted. Then have Fred suggest something else that she didn’t agree with. Only to have Janice come to the conclusion of what she did want. And if she knew all along, to give that job to someone else to do, when you already know what you want. It’s a one page and a couple of lines long. Yet the other person spends 3 weeks preparing it for you. You wasted company time and money.
    This last paragraph is a perfect example of how a person trying to do a good job might over explain him/herself or the situation. Hoping those reading it will agree…..

  2. Sunil says:

    I think instil a dialogue of expectations is the key to macro managing. It seems Janice not very keen of his/her expectations very well. He/She needs to be more strategic in his dialogue.Initiating a dialogue of the assignment, asking open ended questions, that convey interest, accountability and autonomy. Fred’s independence is the key to his performance. Janice seems like staying in nitty gritty details and interfering with freds work, that is obviously demotivating. That may not good for any innovative way of doing things, and stifles fred to use his own judgement.

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