The following examples happen regularly at all levels of all kinds of companies:

  • A manager asks a direct report “can you do X?” The report spends 10 times the amount of time that was expected to do the task, leaving the manager befuddled – “I wish you hadn’t spent so much time.”
  • An executive asks a quick question in a meeting “can you check this out for me?” This brief ask turns into 24 people preparing 4 versions of a slide deck and working over the weekend in preparation of a meeting that now has a career-making aura. In that meeting, the exec sees the first slide’s first sentence summary and says “oh ok, thanks, no need for a whole presentation.”
  • A leader says “we need to be modern, no excuses!” Not wanting to seem dumb, nobody asks what that means. A month later that leader is deeply disappointed when a critical project is not being shipped on time: “you said to be modern, so we put together a modernization project that focused on a sweeping tech upgrade; that pushed out a bunch of other projects.” The leader had meant to say that over the course of the next couple years, they needed to refresh the syntax of their APIs in a new version.

Imprecise asks from managers and leaders cause a disproportionate amount of turmoil and wheel-spinning. To combat this, leaders should be very precise with the amount of time investment they’re asking for when they ask for things. A little bit of awkward precision up front can save major headaches down the line. Here’s some examples:

  • 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.”
  • 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.”
  • 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.”
  • 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”

On the flip side, if you get an ask from a leader:

  • 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?”
  • 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.
  • 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.

Read More