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Have you ever walked out of a 1:1 with your boss and felt…well, like it wasn’t a 1:1 at all? It’s always tricky, isn’t it?. It’s either you talking or them talking. If you have a good manager you will likely get a lot out of that meeting, out of every meeting you have with that person actually but luck does run out and eventually you get to a point when meetings become short, topics repeat themselves and you just stare blankly at your manager’s face hoping that he or she starts the conversation with something different than “so, how are things?”.

Truth be told part of a manager’s job is to help you navigate your Career and grow, listen and work with you in reaching your potential. But it is also part of that person’s job to give you feedback, which is never easy and sometimes challenges their own skills. Giving and receiving feedback can go the wrong way, that’s a fact that’s never discussed a lot but it’s as real as it gets: if you don’t know how to give it, you might end up talking too much. If you don’t know how to receive it, you might take it the wrong way.

That is why it’s always better to think before you speak and most importantly, before you ask. Your manager is there to answer your questions (or should be), and it is likely that whatever your day-to-day looks like you’re already asking that person a lot things but what about those instances like your 1:1 meetings, or maybe a business trip or even a happy hour, when you get to ask other things? The more private the context becomes, the deeper your questions get to be.

The first thing you need to do is assess the context properly. If it’s a 1:1, your questions will likely be around what you need to do get better at what you do. If it’s something more informal, your questions can be a bit more intimate, showing that your interest goes beyond your tasks and more around getting advice from someone who’s Senior to you and can help you with his or her experience.

A second next step would be getting comfortable enough to ask the questions you want to ask. If you’re not comfortable enough, your questions might come up a bit harsh, or clunky and that usually translates in poor answers, or as harsh and clunky as the questions. It means you can work in creating a certain atmosphere. Believe it or not, if you set the tone before the question, chances are you’ll get a lot more out of every answer.

And finally you just need to pick the right questions. You can ask whatever you want to ask of course, as long as it’s proper. You wouldn’t ask something too private or something that would put your manager in a position where answering that question creates some liability or any kind of problems. If you’re doing that…be warned, it is likely your manager will see it coming. What helps me the most is asking the questions silently in my head and trying to figure out what do I really want to get with each one of them. I then discard the ones that really don’t make sense and I leave the ones I can make the most out of each answer.

Here’s a quick list that might help you formulate the proper questions:

  • Don’t just ask for feedback, be specific. If there’s something you really, REALLY want to know about how your manager sees you, go straight to the point. A good example would be asking something like: “How do I get better at forecasting?”, which is a question all sales managers wish their sales reps would ask.
  • Focus in the future, not the past. Unless there’s something you haven’t worked out yet and need help doing so, focus on those things that lay ahead of you like getting to the next level in your career.
  • Validate conflict resolutions. If you have worked out something alone (or with your manager’s help), you can ask about it and work from there on other questions around that topic, like “should I have done it differently?”. Look for a broader view on specific approaches you took.
  • Examples. Your manager is (or should be) a source of examples on things you want or need to get better at. Pose your questions so the answer you get is not a text-book one but rather comes with an example. It is likely that your manager’s best asset is experience.
  • POV. Your manager’s point of view is important, just know what you’re asking for. Don’t get personal but rather pose a situation in which you need a second opinion on your approach to it.
  • How can I help? Not many employees offer their help to their managers, but this is a great question to ask. Sometimes your manager does need help even if it’s helping you and the fact that you offer yours allows them to work things out in a better way.




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