How to Have a Better Relationship with Your Boss

Hello and welcome to this week’s episode of the podcast. Today, we’re going to talk about how to have a better relationship with your boss. Bosses are one of the most important relationships that you have at work, maybe even the most important. And I’ve talked about the boss relationship in quite a few episodes, but not quite in this way. Today, I’m going to share four specific actions you can take to improve the relationship with your boss. And really, these can be applied to any key stakeholder relationship that you have. Because As you know, at the end of the day, your relationship with your boss and stakeholders impacts your potential growth, how much you like your job, even your mental health at work. And when you take a few strategic and intentional actions, you can build and sustain a healthy, healthy and productive relationship that can lead to better performance reviews, promotions, and overall, just more happiness in your career. Now, although the best of managers try to avoid bias and favoritism, when your boss likes you and you have a good relationship, it’s natural for them to just think of you when new projects come up, opportunities for visibility and exposure, like getting to go to key leadership meetings.

So even if you don’t think your boss is great, I really encourage you to take in these actions that I’m going to share with you today and give them a try. Over the years, I have definitely had bosses that have helped me grow, challenged me, and were fantastic mentors, and those that helped me back in my career. That elevated men and treated me like a woman, and you know what I mean. Assigning all the administrative work to me because I’m good at it or the best at it, and doing the real work behind the scenes the men are the ones invited to the meetings and the ones talking about it and getting all the glory. Now, there will be misogynist men that we just have to encounter, and this episode isn’t about the extremes. We all have biases, and Women, there just sometimes is an uphill battle and things that we have to deal with that white men just don’t. But instead of giving up or settling for this norm, we have to rise above it. We have to get better at our skills and learn to navigate the workplace, difficult colleagues and bosses. It might not feel fair, but this is how we get ahead.

This is how we beat the game. In my experience, playing the good girl, waiting my turn, being more like them doesn’t actually move your career forward. We end up feeling worse. We end up feeling more like an imposter, more like we’re not being our authentic selves. And that doesn’t lead to a fulfilling career. We end up staying more stuck. And even when Even when we do get ahead, even when we do get those promotions, it doesn’t feel the same as if we did it in a way that felt really good to us and we felt like we got it on our own merit and we got it being our authentic self, letting our own strengths and skills shine. So instead, I like to really pivot to focusing on the skills you need. Because when we level up our skills, we win. Because we won’t just elevate ourselves into meaningful roles and opportunities, but we take these skills with us for the long run. The skills are what will stick with us as we progress in our careers, and they will compound and give us more success over time. So while others might wait their turn or rely on just their Brosky friendships to help them level up, that’s a short term game.

I truly believe that they will lose in the long run. It’s like strategy. It’s like playing chess. We are looking ahead at the big picture and equipping ourselves to be successful in any environment, not just ones that we succeed in by playing political games. No one wants that. Think of this episode as an opportunity to build your skills, to think of your relationship with your boss differently for how you can leverage this relationship regardless of how much you like them to further your career and get what you need to do your job well. Experiment with the different actions that I’m going to give you today. Try one of them, try all of them and just see what happens. You’ll start to show yourself just how much is in your control and how focusing on skills is really the key to making the difference. All right, let’s dig in. Let’s start with these actions. The first one, understand your boss’s goals and challenges. Now, bosses are often misunderstood. If you’re a boss, you know this. There are so many things that bosses have to deal with that are not visible, and on top of it, they’re humans with their own flaws and personal issues and strengths and weaknesses.

Understanding your boss’s goals and pain points or challenges will help you be an invaluable asset to them. It will help you communicate better, get more visibility, because you know what the real problems are, you’re going to be able to be a go-to resource. Now, here’s an example. Earlier in my career, I was promoted to be a senior leader, and I had three different managers and their teams reporting through me. I was promoted beyond my peers into that leadership role. Now, one of the factors in this is I observed and got to know my manager from a place of curiosity instead of judgment. When my manager struggled, I didn’t complain and tell her the things that she was doing wrong. I looked to see how I could help. When one of the teams was struggling with errors and compliance issues, I offered to help them out and work with my peer leader to train them and resolve the root cause. I talked to my boss about where she saw our department going, what we needed to do with our stakeholders to increase revenue. By just talking to her and offering to help where I could, again, from curiosity, not judgment, it put me in a unique position to stand out and be seen as a leader among my peers.

When my boss saw this over time, we talked about how I could continue to support her and make her job easier, furthering our department goals. I just had a natural curiosity and getting to know more about the work that she was doing, and then through that, was able to help her with things that normally wouldn’t be within my scope. She ended up creating a new senior leadership role for me and changed the reporting structure where my peer managers were reporting to me and I was the one reporting to her. Now, you can do this for yourself, too. So here’s a couple of things that you can do just to get started. You can schedule a one-on-one meeting to ask your boss about their priorities, their goals, their biggest challenges. You can show interest in their success, which is going to foster stronger alignment and teamwork, and it’s going to show that you’re on the same team, that you’re a team player. You can also work this conversation into your regular one-on-ones. You can also, next time that your boss does something or the stakeholder does something that you just don’t get that you think was just a stupid idea, right?

Instead of having the judgment of, That was stupid. That doesn’t make sense. I just encourage you to approach it with curiosity of why would they make that decision? Because at the end of the day, judgment isn’t going to get you ahead. Observe their priorities. Pay attention to the projects or goals that they emphasize in meetings. Understanding what’s important to them will allow you to anticipate their needs and then also be able to insert yourself and help, which is going to get you ahead in the long run. Now, number two is to be proactive in your communication. When it comes to your boss, I have found it to be wildly successful to proactively communicate, and that includes discussing preferences around communication and updates on projects at work. So many conflicts can be avoided when you are transparent and proactive in your communication. We tend to assume things or work the way that we have worked before that has given us a lot of success or blindly follow advice we’ve gotten in previous roles to be successful, and then it just doesn’t work in our current role. And so that can happen in these relationships when you’re working with a new boss or stakeholder where there’s a lot of assumptions or old ways of working brought into that relationship.

Because some bosses want to have proactive updates on projects, some are okay with just waiting until the end. You might find it helpful to have a check-in part way through to be sure that you’re on the same page and that you’re meeting their expectations of your work, especially if you tend to be a perfectionist. You might want to wait until you have everything tied up and about to show it, believe me, ask me how I know, so that you’re putting your best work forward. But what can happen is you spend way more time on the project and deliverable, which builds up an expectation for your boss of what it’s going to look like. And if you’re not on the same page, it’s going to backfire. You spend so much time on something and your boss is left thinking that you just delayed the work and got it wrong. So instead, you could try having a check-in partway through just to discuss what you’ve done so far. You can talk to your boss about this to see what they prefer. Ask them how they like to communicate. Do they want to stop by, pick up the phone, use Skype or your chat message internally?

Do they like email? Don’t wait for your boss to ask for updates and don’t assume how they like to get updates or how they like to get their communication. Proactively schedule these check-ins to give updates on key projects or challenges that you’re facing. But more importantly, talk to your boss about the way that they want to get these updates. So a couple of things that you can try is to solve problems before they escalate. You can bring it up early with the solution in mind, with what you anticipate the risk to be. So if your boss delegates something to you or you’re working on a project and you see a problem with it, don’t just try to go fix it on your own or ignore it or assume that they know the problem. Just have an open conversation with them, but you will position yourself as a leader if you have a solution backed with your problem or what you identified. This is going to demonstrate leadership and initiative. Also, be sure, like I’ve said, to clarify expectations. If something is unclear, ask for clarification rather than making assumptions, because it’s better to ask upfront and then deliver something that is actually what they need as opposed to just guessing because you’re worried about how you will seem or if they think that you won’t know what you’re doing, if you ask the question, just ask the question.

It’s going to pay off in the long run. Now, number three is to adapt your communication style. When I work with clients, we do an assessment to identify their communication style, their needs and priorities, and also blind spots. And you also learn how people read other styles so that you can adapt your communication to your audience or to your stakeholders, to your boss. Because it isn’t about you being someone you’re not, it’s about the skill of being an excellent communicator. What defines your ability to communicate well is not how well you think you did, but how well the audience or person you’re speaking to understands and receives what you said. I worked for this boss that had a totally different communication style than me. I didn’t notice it at first, though, because, of course, I went in, I was a high performer, always had been, always had gotten good reviews, had a good relationship with my prior boss. So I didn’t do some of the things that I’m suggesting that you do today. And we kept having miscommunications. They were more subtle, less direct in what they wanted. And I’m more direct and I’m more fast paced.

I also really invest in quality work and I want to delight people with what I deliver. So I would think that I knew what they wanted. I would deliver my Nordstrom level work and they were like, oh, you didn’t have to do all that. It was so frustrating. Have you ever experienced this before? We put so much work into something and you think it’s just going to wow your boss and they’re like, oh, I didn’t need all this. Thanks anyway. You hit it out of the park and their response is like, I didn’t really need all this. Now, how I repaired was to be more curious and ask better questions so I could be clear on what they needed or wanted so I didn’t waste my time or theirs. I’m also someone who likes to talk through ideas, which is why this podcast is great for me. And this was someone who liked to think through ideas alone. So this was another way that I had to adjust my style to meet theirs. And what this can look like is sharing when you want to talk something out or providing a pre-read so that they can read through what you want to talk about ahead of time so they can process and marinate on their own thoughts and the information so you don’t overwhelm them.

Now, some other things you can do is to observe their preferences. Do you notice that your boss writes really detailed emails or are they more quick bullet points or face-to-face conversations? I’ve had bosses that want all of the details in their emails, and I’ve had a boss that was like, Honestly, Melissa, if it’s more than three bullet points, I’m not reading it. So you’re wasting your time writing it to me. So knowing that information, having those conversations, is really going to save you so much frustration. It’s also going to help you have that better relationship with your boss, and that’s going to help you stand out and again, get more opportunities and advance your career. So it also matches their tone and approach. If they’re more data-driven, if they’re focusing on facts and analytics, if they prefer big picture thinking. Avoid getting too lost in the weeds. You want to look at what is the right way to deliver the information to them? What information do they need to pay attention to? Have you ever gone to a training or something where they don’t tell you what you’re going to learn? They’re just providing all of this information and you’re trying to figure out how it’s relevant to you and what you need to do with that information, whether it’s at a town hall or a department meeting or training.

It’s that. If you notice with my podcast episodes, I always tell you what you’re going to be learning and how it applies to you before I dig into the content. Otherwise, you could read the description, you could see the title, but you’re trying to piece it together and that’s distracting you from actually taking in the information. So it’s the same thing when you’re communicating with your boss, you want to think about how they like to get information? Because if you’re very data-driven and you want to provide all of the data to support your conclusion and they don’t understand where you’re going or what your ass is going to be, that might just be very overwhelming. And the whole time they’re thinking, get to the point they’re not actually listening to you. So it’s good to just think about what is the information they need, how do they need it. And again, the easiest way to do this, if you don’t want to just observe and be a detective about this, is to just ask their preferences. So you can ask in a one-on-one, ask directly how they prefer to receive updates or tackle problems.

And this is going to show respect for their work style and also that you care about their needs as much as yours. Now, the last action today is to provide constructive feedback and ask for it. Now, giving and receiving feedback is really important to any stakeholder relationship, especially your boss. I have a whole separate podcast episode on giving and receiving feedback and another on questions to ask in your next one on one that is geared to getting meaningful feedback. So I would check those out if you want to take a deeper dive on this topic. Feedback doesn’t have to be stressful. Let me just say that. Something that I did with stakeholders and my boss in my career was to have check-ins where I asked them specific questions that allowed us to have an open conversation. It’s the same approach I use with my clients to measure results and for them to use it with their stakeholders, and they always rave about how well it works. Giving and receiving feedback helps build mutual respect. It’s a two-way street that improves not only your performance, of course, but also your boss’s understanding of how they can better support you without you having that awkward conversation of like, Can I let you know you did this thing I didn’t like?

I’m going to tell you what to do instead. Because the feedback loop that you want to have with your boss and stakeholders is about problem solving and process improvement and avoiding any resentment or false opinions. It’s also about acknowledging what is going well because most people want to know what’s going well, what their boss appreciates, so they can do more of that, so they can feel acknowledged and valued for what they’re contributing. Now, I can share some insider information with you that there are things that can hold your career back that are not part of your performance review. If you are wondering deep down, why do I keep getting these performance reviews that are so glowing, but I’m not actually getting promotions or advancement opportunities, this could be why. There’s something that they’re not telling you. There are things that we can do or not do that are so minor. They don’t actually impact our ability to deliver, but they leave people questioning if we’re actually leadership material, if we can handle that bigger project. If there’s any doubt, advancement is going to be more difficult. I suggest pulling out this information to get to the micro things that could be improved proactively so that you’re ahead of this and also have those glowing performance reviews that also lead to the career growth that you want.

Now, you might be worried about giving your boss feedback, especially if you want them to improve in some area. So this method I’m going to share with you is going to be so helpful. Here’s my hack. At regular intervals, suggest with your boss or stakeholders that you review what is going well, what isn’t going well, and what either of you can do differently. It’s that simple. This allows you to both acknowledge what is working and get the positive feedback, but also have an open dialog about something that didn’t go well, and then what you can do to prevent or change that moving forward. You can do this on overall performance every couple of months, or this is something that you can integrate as part of project reviews or certain milestones that you achieve. It’s not, what can I improve on? Am I doing a good job? Do you have anything for me? Here’s where you’re not doing well. It’s strategic, it’s collaborative, and it’s not personal. And the more that you do it, it’s going to become the culture of your relationships. So try this with your boss. If you have a team, try it with your team.

And you can also, like I said, that podcast episode I have on three questions to ask in your next one on one, you could include that with these questions that I gave you today. All right, so let’s recap the four ways that you can have a better relationship with your boss. Understand your boss goals and challenges, be proactive in your communication, adapt to their communication style, and provide and seek constructive feedback. Improving your relationship with your boss isn’t just about making work more enjoyable. It’s a strategic move to advance your career and future leadership opportunities. I really encourage you to just take at least one step from today’s episode and apply it next week. Maybe it could be scheduling a meeting with your boss about their priorities or observing their behavior, clarifying expectations on a project, you can choose what step you want to take. All right. Have an amazing week. I have something special for you. 

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