I recently received this question from a client, and because it was a great one I decided to write some more about it.

My client asked, “How do I know I’m working on the things that my boss really cares about?”

They went on to explain that they would like to have a promotion within a year, and that they were working hard to get there. But it dawned on them recently that they’ve essentially designed their own development plan based on what they think their boss wants to see and what they think the needed skill gaps are. (Key word there is think—not know.)

Meaning they MIGHT be working on the right things to get to their goal, but they might be wasting their time focusing on things that aren’t that important.

So how do you know you’re working on the right things to get where you want to be?

The bottom line is that this is going to require a series of conversations with whoever your decision makers are. This probably includes your boss but also might include their manager or other senior managers around you depending on your situation.

Here’s my top advice for how to approach this situation:


  1. Decide who the decision makers are. It’s ultimately your manager, unless your promotion involves moving to a new team or department. In this case you’ll need the buy-in of your current manager and your potential new manager. However, other managers will likely be involved in the conversation. Even if they are not the final decision makers, their views matter. Think about the last time you interacted with them and what work they’ve seen you do. If you need to do some relationship building here to get to know people better, it’s good to start now.
  2. What skills do they think are important? Keep the guesswork out of this one and ask. Go to your main decision maker and ask them to explain to you what excellence looks like in your target role. Which hard skills are most important? Which soft skills? Get a good picture of what this role really requires; it will help you prepare and it will help you sense-check that it’s really something you want to pursue.
  3. Where do they see you in relation to these required skills? Where are you already doing well, and where do you have some development to do? I would start this conversation off with a self-assessment. No, they aren’t the most fun things to write, but it’s a much easier way to start a conversation since you are giving someone something to engage with rather than asking them to have a clear picture of you right off the top of their head.
  4. Be open to hearing something you weren’t expecting. You might be closer or farther from your goal than you were expecting. You might have not understood the full scope of what the new role requires. Go in with an open mind and a way to take notes so you get the full value of the conversation and can use it to propel your success.