What to Ask Your Boss (9 Questions They Want to Hear)

In this solo coaching video, Natalie Fisher explains why employees often feel frustrated with their bosses due to unclear expectations and offers a concrete, research‑backed framework of nine questions that can transform the employee‑boss relationship. She begins by citing Harvard Business School research that shows asking the right questions improves communication, then illustrates the problem with a client story about a manager who seemed erratic and unpredictable. Fisher groups the nine questions into three strategic categories: (1) Understanding the boss’s current pressures, (2) Clarifying performance metrics, and (3) Aligning the employee’s focus with the boss’s priorities. For each category she provides two specific sample questions, explains why each question matters, and gives tips on how to use them in one‑on‑one meetings. She emphasizes the importance of concrete examples, tracking answers, and revisiting the questions when priorities shift. The client case study shows how consistently using these questions turned the employee from a confused, second‑guessing worker into a trusted strategic partner. Fisher wraps up by encouraging viewers to subscribe, explore her “How to Talk to Your Boss” series, and access additional resources for different boss types.
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This video is about what your boss actually wants to hear but doesn't know how to tell you. So stay tuned. So research from even Harvard Business School says that bosses and employee relationships are much better when the employee asks questions. But here's the thing, most people don't know what questions they need to ask in order to really get that communication feeling like a well-oiled machine between them and their boss. And this can lead to a lot of frustration, I've been there, I've done all the trials. And so in this video, I want to share with you some simple things that you can ask your boss to get on the same page with him and to go from being frustrated and second-guessing yourself all the time and never knowing what it is that your boss wants from you to becoming their most trusted advisor. So that's what I'm going to talk about. And if you don't know me, my name is Natalie Fisher. I help people go from knowing that they are really smart and capable to actually getting what they need and actually being able to share that very effortlessly and make it a part of who they Um, because one of my biggest, strongest values is that it's not about changing who you are or changing your personality. It's about adjusting your message and adjusting the way that you communicate so that you can be heard in the way that you deserve and you can get what you need faster and be more successful. So it really benefits everyone, but this is for you, not for, not for your boss. So if you're frustrated with your boss, this will help them, but really it's for you to be successful. So here's what my client did. So I'm gonna use a client example here in this video because I coach a lot of clients on these things and real-life examples are just the best to be able to get my points across. So my client, what she was doing was that she was assuming her boss was scattered. She came to me and she's like, oh, he's so all over the place. One day he's gonna compliment my work and tell me that I did great. And then the next day out of nowhere, he's just criticizing what I'm focusing on. And it's like I was going to San Diego and he thought I was going to New York. And we just were on totally different pages. But yesterday he was so happy with what I was doing, so I don't even know what's going on. And she just gets really frustrated, which is understandable, right? So she's trying to read his mind and trying to anticipate his moves when his moves seem to have no real structure to them or no real way to predict, right? Sound familiar? I know I've been in this situation before and it can be super frustrating. So Here's what happens is most people try to read their boss like a broken navigation system. You know, when the GPS will redirect you, you'll be going down one path and you'll think that's good. And then all of a sudden it'll be like, oh no, you were supposed to be going this way, right? And constantly getting new directions, but never actually knowing what the destination is. And that, that's where you're getting stuck. So you're following these instructions and you're going, going, going. And then you might be like, oh no, I have to switch course. Or, uh-oh, now I have to go back. I didn't know that I wasn't supposed to be headed that way. So, here are some quick little transformational tips that you can use to change the way that you communicate with your boss so that you can be on the same page as much as possible. And you can stop second-guessing yourself and start understanding what it is they need from you. So, one, you want to understand their pressures. So, every day they could be getting pressure from their boss or from a different thing or some things, things are happening in their brain and they're not necessarily thinking, oh, I better tell my employee about this so that they can adjust. They're just handling the pressures of what's going on for them. So, some good questions to ask them in this department would be, which goal matters to you the most right now and why are they priorities right now? So, what is it that's important to you right now and why? Second question, what concerns keep you awake at night thinking about our team initiatives or what our team is working on? So, what are the concerns right now might be a way to put it. But you want to know, like, What is really stressing them out? What is keeping them up at night? Category number 2, clarifying metrics. So one thing you can ask them is, how will my performance be evaluated on these objectives? So if you're working on something, you want to know how that's going to be evaluated, what the success is going to look like, because you don't want to go down that wrong path. So this, this question actually prevents you from going down the wrong path, and it kind of nips things in the bud. So If you ask that question, how will my performance be evaluated for these objectives? Then you're going to be able to start a discussion of whether you actually need to go down that path, how it's going to be evaluated, and it'll give you such a clear way to see, okay, am I investing my time in the right place right now? Second question, what distinguishes acceptable work from exceptional work? So what distinguishes good from good to great? And maybe discuss an example there. Examples are really great. Whenever I possibly can, I ask for an example or I give an example. Example, and that concretizes things. My brain works in a really concrete way. I love to have an example so that I can see, okay, what would be the difference between this being acceptable and then this being knocked out of the park, right? And even if it seems obvious, to just clarify that so that you can know exactly what to expect. And then you can always re— um, come back to these conversations and say, okay, on this day we discussed this and you had said that this would be knocking it out of the park. This has now been achieved, kind of thing, right? So category number 3, aligning Aligning your focus with their focus. So the questions to ask here is, here's how I'm allocating my time. Does this match the priorities that you have right now? So you could tell them what you're working on for the day and say, or for the week or for the month or for the quarter and say, this is what I'm working on right now. Do these priorities match your priorities? I just want to make sure we're on the same page. Okay. Second question, what's the single thing I can handle right now that would simplify your job? How could I make your job easier right now? Right? And it's good, like if you're meeting one-on-one to pick and choose these questions as feels appropriate, but these questions will really help you laser focus and direct in as to exactly what it is you're working on and that you're on the path that they expect you to be on. And if that changes, then you wanna be asking these questions again. And if you're having a one-on-one meeting and you track what you discussed and say, okay, this was the answer to this question, this is what they said at this point, this is what they said at this point, then you wanna reevaluate and be able to say, okay, this is what we had discussed. When did this change? Right? And when did I need to check in with you about that change? Right? I understand these videos, they can't be like, they can't apply to everybody all the time, right? That's why I do the deeper work with people one-on-one and in my containers, um, where I work with people personally, where I can actually say, okay, they said this and we can work out a plan for your specific situation. But these questions will definitely help you clarify and get laser-focused on what it is that you need to be doing. And so the, my main goal is that you stop second-guessing yourself and you stop going down the wrong path and you stop wasting time by asking really laser-focused questions so that you can get exactly what you need, the information that you need to be doing your best possible work. So once these approaches were used, so once my client was able to implement these questions, she was asking these questions periodically, this changed the dynamic, okay? Completely changed her one-on-one meetings. It completely changed the direction of the discussion, the answers that she got, and she went, went from experiencing being confused and felt like she was thrown all over the place and didn't know what was going to happen next to becoming a trusted strategic partner. Okay. And that is where you want to be so that you can move ahead so you can get your, you can get what you need. So basically the name of the game here is communicating and adjusting your message so that you can be heard and you can get what you need in return to do your best work and to be the most successful that you can in your role. So if this helped you and you see how this conversation hits a little bit differently, hit subscribe to the channel, because I'm breaking down exactly how to use these insights with every single different type of boss. This video is also part of a series. It's called How to Talk to Your Boss, and there's several other videos part of the series. So if this was a good video for you, I would encourage you to go back and listen to the 4 different types of bosses, the ways to talk to each different types of boss, see which kind of boss you have. It's kind of fun. And go to my— go to the link below, find the resource that's going to suit you the best. I have several resources depending on where you're at in your career. You can sign up for my Event, and that link will be below. I can't wait to meet you. My name is Natalie Fisher. Subscribe to the channel. Give thumbs up if you like it. Give thumbs down if you didn't like it, and I will see you later, or I'll see you in the next video. Have a great day.
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