How to Push Without Pushing People’s Buttons

Ever felt like you needed to push an employee for more – better work or faster work or new ideas – but weren’t sure how to push in a way that wouldn’t make you feel like a jerk?

To be clear, there’s nothing jerky about pushing for more when you need it … but we’re human, and most of us don’t want to feel like we’re being ogres when we’re telling people that something isn’t good enough.

Here’s some language that you can use to push people and hopefully still leave everyone in the conversation feeling reasonably good.

How to push on deadlines:

  • “So that I understand, what’s involved in making this happen?” (This might get you context that you didn’t know about previously, or it might help you lead into talking about ways to move things along more quickly.)
  • “I hear you that you have a lot going on. Taking that out of it for a minute, when do you think this would ideally be done by?”
  • “So that I understand the context, what’s behind the timeline on this?”
  • “Suppose for a minute we had to get this done by Thursday. What would it take to do that?”
  • “What is the next step for this? Do you think you can finish that part today/this week, instead of next week?”
  • “How long does X take? Do you think you can find time for it in the next day or two?” (where X is a component of the project)

How to push on quality:

  • “If you wanted to strengthen this, what would you change?”
  • “What would you do with this if you were able to spend a little more time on it?”
  • “Here’s what’s in my head on this. I’m picturing (Major Funder/Player) seeing this and wondering about X.”
  • “As you know, I think you’ve been doing excellent work on this kind of thing, but this one doesn’t feel up to that standard.”
  • “I know you’ve been working hard on this and that this is not for lack of effort, but I feel like we could be getting better results in this area. Can we talk about what that might look like?”
  • “Everyone assumes that because we’re young we don’t know what we’re doing, so we have to counter that by being extra-polished in our presentation.” (In other words, use the “everyone feels X about us so we have to do Y…” construction to explain why you feel particularly strongly about a particular dimension. Y might be things like making sure our stuff is really perfect / proving value quickly / being easy to work with.)

How to push on ideas (when you think an idea isn’t well-thought out or doesn’t quite make sense):

  • “Can you say more about how that would work?”
  • “What do you see as the downsides to that?”
  • “I can imagine someone hearing this and saying X — what would you say to that?”
  • “Here’s what gives me pause about that…”
  • “Can we talk through how this would work with a real-life example?”