Today on Hacker News, I saw this article explaining how a manager should ask their direct reports to complete a task. In short, you need to be mindful of what kind of effort you expect them to put into the task, be explicit about how it should be prioritized against other work, and how you plan to use whatever they are doing for you.

The examples listed in the article are great and I think cover most of the things I’ve dealt with as a manager myself:

  1. Clarify the expected time investment: “Please look into this for me. Do not, DO NOT, spend more than 20 minutes on this. Please come back with whatever you have after 20 minutes.”
  2. Be clear about how it should be prioritized: “I expect this to take about 2 weeks and not cause major deprioritization of other efforts. If that timeline doesn’t seem accurate after diving in, or if you end up having to prioritize against other things, reach out to me ASAP.”
  3. Distinguish between whether you’re looking for prior art or new art: “Tell me if we have anything on this topic already; if we haven’t even thought about it yet, that’s all I need to know.”
  4. Tell people exactly what you’re going to use the information for so that they can calibrate effort levels: “I am going to put this into a response to a sales prospect”; “I need to know this just in case it comes up during Q&A at our next All Hands”; “this is going to be the main topic of our next board meeting”

Item #1 has served me the best. I found early on as a manager that sometimes I wanted a quick answer to a question, but I misunderstood the level of effort involved in coming up with that answer. It’s unfair to be frustrated with someone for trying to go above and beyond for you. I’ve found that asking up front how long a task is expected to take and time-boxing the amount of time you’re willing to invest is a great way to avoid frustration from both sides.

Item #4 is another great idea—one which I practice more often when a manager above me asks for something. This is actually a great idea for all developers to ask when it comes to things like collecting data or generating reports.

If you’re a developer you’ve probably been asked to write reports before. Until I learned to ask explicitly, “what questions are you answering with this data?” that there were always a few back and forth trips as you worked with a stakeholder to verify they had what they needed. Non-technical people can’t be expected to think about all of the different database columns or other hoops you need to jump through. They can tell you the questions they need answered. By asking that up front, you can help them identify the “oh yeah, I’ll also need ______” type replies and get the task knocked out faster.

If you’re a developer, ask the inverse of those questions when a manager asks you to complete an out-of-band task:

  1. Ask for how much time they think is appropriate. “Are you expecting something super thorough, like multiple hours of effort, or a quick write up?”
  2. Don’t assume everyone else knows what’s going on. You’re not going to look dumb if you ask a question; you’ll definitely look dumb if you do the totally wrong thing because you didn’t ask a question.
  3. Do not, DO NOT, assume they are too busy to answer clarifying questions as you work on the ask. Dollars are flushed down the drain every day because people incorrectly assume leaders don’t have time to clarify their asks. Rooms full of people analyze emails and instant messages from the leader like ancient artifacts. Ask the leader for clarification - if they have time to ask you to do something, they have time to clarify that ask.

I can’t stress #3 enough! Managers are always busy, but you should never feel that you can’t ask for more clarification. I’ve never had a boss get frustrated with me for this, and I’ve never gotten frustrated with a report for doing it to me. On the contrary, good bosses appreciate any questions that help put them on the same page with you.