How to Turn Even the Most Difficult Boss Into Your Ally

Making the leap from high performer to manager changes everything—including your relationship with your boss. In this episode of The Career Refresh, executive coach Jill Griffin breaks down why your boss can make or break your leadership success and shares practical strategies for building a strong partnership, even with difficult managers. 

Learn how to lead with your strengths, navigate authority dynamics, manage up effectively, and position yourself as an invaluable ally. 

Whether you're a new manager or struggling with a challenging boss relationship, this episode will help you shift from threat mode to mutual success.

Chapters

• 0:00 From IC To First-Time Leader
• 1:02 Promotion Paradoxes And Boss Dynamics
• 2:49 Leadership Versus Management
• 4:02 Create Capacity, Not Control
• 5:13 Defining Done And Building Autonomy
• 6:45 Is Your Boss Coach Or Judge
• 8:05 Ask For Help The Smart Way
• 9:16 Lead With Strengths And Context
• 10:25 Borrow Your Boss’s Superpowers
• 11:38 Drop Old Baggage And Patterns
• 13:05 Mutual Dependence And Trust
• 14:06 Read Their Priorities And Style
• 15:35 Stop Gatekeeping; Share Information
• 16:39 Results, Grace, And Generosity
• 17:35 Build A Smart Skip-Level Relationship
• 19:04 Closing Mindset And Call To Share

Transcript

From IC To First-Time Leader

SPEAKER_00 0:00

Hey everyone, welcome back to the Career Refresh. I'm Jill Griffin, executive coach, career strategist, and your guide to career reinvention. All right, today we're talking about one of the biggest transitions that you are going to make. And this is jumping from a high-performing individual contributor to a leader. And specifically, how do you manage the relationship with your boss or your new boss when things might feel very different? Here's the thing: your boss can make or break your success. I know you know that, but when you step into leadership, it becomes a little bit more complicated sometimes. And that relationship is vital to the success of you, your team, and the company. All right, so let's dig in. So you've been killing it at work. You are exceeding targets, you're delivering results, you then get promoted to the next level up. Okay, so I see one of two things happen. Either it feels like you're working for a completely different company, or nothing has changed except your title and hopefully your bank account. Because now you're supposed to manage all the people, but still doing your old work. Your boss really hasn't moved over, they're still in the weeds, nothing's really changed. And this becomes some of the paradoxes that happen around promotion. And I hear this all the time. You know, I was talking to a leader just this week where his boss is now the SVP, he's the VP. And what is happening is the boss is still in the weeds. And there's a lot of tone from the boss, like, you're not doing it my way, therefore it's wrong. And we don't know yet if it's wrong. He was promoted because of his own gifts and his own skills. So give him a chance to grow and breathe. So how does he manage that without really causing friction? And that's the kind of examples that we're talking about today. What no one tells you is that being excellent at your job doesn't make you excellent at leading people. It doesn't. It's a skill that is, it needs to be trained. You can work with a mentor, a coach, you can get professional development. But this idea that the skills that got you promoted, that technical expertise, that core competency, that subject matter expertise, your ability to execute, that doesn't necessarily make you a great people leader. And you've all been in this situation. I mean, I've been in this situation where someone is excellent at their craft and they are just the worst. They're either competing against you or they don't really take much action, or they're micromanaging because they feel like they need to control everything to show that they're doing it the right way, right? So these are all the things that can happen sometimes when we're in this position. So if you came up as an independent contributor, you might not have had to think about how to motivate the team and create capacity for others to get things done. You just had to deliver. But now things are very different. So I want you to think about that leadership is a discipline, it's not a title. And I want to be clear that it's beyond the title of your business card. And unfortunately, in many workplaces, that leadership or management is about either moving the pieces around or um taking credit, maybe, maybe even blaming teams, like you didn't get this done. But they're actually more leaning into the management of things versus the leadership. Both are needed sometimes. But I think management is exactly that. It's like managing things versus um leading is paving the path, showing the way, building their vision. What's the glide path? Helping people, a mixture of showing and telling. You want them to have their own agency. So you don't want to over-suffocate them so they're not bringing their own gifts and talents to the table. You want to show them that glide path. Whereas managing is sort of that level, I'm going to look at of like control, that everything we need to move this piece here and that piece there. And I'm managing the board, so to speak. That's where we want to be less of that and more into the leadership. We're not going to be that person. So your role as a leader, like I said, is to create the capacity for others. It is not to do their work. It is not to micromanage them. It is not to be that helicopter parent. Your job is to create a team that knows how to navigate change. You want to give them a balance of support and stretch, which is going to differ depending on the individual that's in front of you. And you want to guide them so that they're able to really bring their creativity to the table, to the project, the challenge at hand, letting them fly because you're going to learn from them too. But yes, showing them that there's a path and what success looks like. I think what happens often is that leaders fall in one of two camps. They either do the hands off or they say, get it done, but they don't necessarily paint what done looks like. So I find that some of the best leadership is letting people know what success looks like, letting them know what the project being done looks like, and then letting the individual come up with their own way of getting there. If they need help, let them know to come ask you. But you don't want to solve everything. Otherwise, you're not building a strong bench strength. And this is one of the biggest problems I see with new leaders. All right, let's talk about the relationship with your new boss. Are is your boss a judge or are they a coach? What have you made them out to be? I want to ask you a question. How do you want your new boss to view you? Give some time to that. What do you want them to see in you? What do you want to demonstrate for them? Right? Give yourself a beat to take that as an assignment, maybe after listening to this and work through that. For this conversation, I want you to think through how do you view your boss? Are they a coach? Are they an evaluator? Are they a judge? Things can get confusing here, right? Because depending on how you choose to view them or how they're showing up, this can be anything from feeling great and in the flow and really feeling like you're starting to thrive, or it can feel threatening. In order for you to grow in your role, you know that you're gonna need help. And this means that you may have to reveal some of your shortcomings at times. You may need to tell your boss where you need help, or that something is not your strong shoot. And I'm gonna guess that your thought here now is like, Jill, seriously, if I show them my weaknesses, they're gonna think I'm not capable, but they're gonna then put me on a performance improvement fan immediately after I was just promoted, right? They're gonna document this. So you tend to hide, you might, you know, pretend like you've got it all figured out, you may miss out on some very important support that you need. The better approach is to learn your strengths and then bring that to your boss. So, what I often find is when you need support, what frustrates leaders often is that someone's coming to them then and just saying, How do I do this? versus saying, Listen, I thought this through. Here's where I'm stuck. Option one will bring us this, option two will bring us that, but I need a little support here. That's the way you need to be working with your boss that you're bringing, you're showing them you have thought through things, but here's where you're stuck, versus just handing over your agency and your thought and out resourcing your brain and letting someone else do the labor for you. Cause you're not then gonna be an ally to your boss, you're gonna be a drag or an anchor that not an anchor in a good way. You're gonna be dragging them into the undertow. The next thing I want you to think about is leading with your strengths. So instead of framing your conversation like, here are my weaknesses, I want you to frame it as like, as you're getting ways of working together, here's how you're gonna get the best out of me. Letting your boss know the ways that you work, the the conditions in which you work best is going to help you deliver the highest quality results. And yes, letting them know you're not at your best might sound a little scary, but letting them know that this is an area that I'm working on and improving, you know, that I can um I can get a little micromanagey at times, uh, but I'm working on improving that. Or I used to be a certain way and I'm working on improving that. You get to choose what to convey and how you want to convey it, but it's critical to remember that your strengths and weaknesses are not opposite. So you working on a weakness is not going to make it a strength. It's going to improve, hopefully, but it doesn't magically turn into something. It's not going to be an area that you need to shine. So letting your boss know contextually the areas that you're working on and that you're aware that this is an outage, that would be an area. So recently I was talking to a client where he was struggling with executive level storytelling, right? He often had to meet with the board, often had to meet with investors. Um, and on the spot, he was struggling with that. So, here again is an example of how you would let your boss know that you're working on something. And it might be something as simple as listen, I know that in going into next week's meeting, what I really need to work on is those three to four beats of the story, those three to four uh most compelling things that they're gonna need to know. So I'm working on that in advance. And I know that there's an opportunity for me to grow. That's what we're talking about. You're letting your boss know that you're getting ahead of it. Next thing I want you to think about is how are you leveraging, once you figured out your own strengths, how are you leveraging your boss's strengths? And this is where I want you to encourage you to watch them when they're in the flow. When are they in their zone of genius? When are they in their magic? When does their excellence show up? When do they see most confident or most content at work? That's where you want to watch them and see if there's any parts of them that you can learn from or borrow, or leverage them by bringing them into a meeting in the right way. Because if you're viewing your boss as a threat and you're constantly striving to prove yourself or protect yourself, you're not gonna be able to deliver long term. You're not gonna be able to think clearly and it's gonna feel really exhausting. So operating from a fight mode all the time can sometimes, I don't know, sometimes it might generate a clever strategy or an approach. It might make you sharp, but it is not sustainable. You are creating harm in your relationships. And that level of making them sort of the villain or the competition is going to impact your creativity, your exhaustion level, your health. And it also rubs off on your team, or your team may not be able to put their finger on it, but they're gonna sense that there's something off there. And now they have to like figure out how to navigate mom and dad that are fighting. And you don't want to do that to your team. Okay. So next that I want you to think about is stop dragging your baggage everywhere. Stop bringing your past into your future. So have you ever felt this way with your boss where like this idea that you're there's an expression like if it's hysterical, it's historical. So I want you to get clear on your thoughts. I want you to get clear on your authority, and I want you to not drag your baggage into this new relationship or the container of the relationship is new because maybe you're still reporting to them, but you're now promoted. Do you constantly bend yourself into a pretzel to get approval? Do you find that you need validation from your boss to feel like you're in a good place? Do you feel like you need to tell them that they need to tell you things so that you know that they trust you? I want you to reflect on your history here because if these are the patterns that you're making, if you don't change your mindset and therefore your behavior, you may bring those patterns into this relationship. Your boss is not going to always be the same. You are not always going to be the same. People are messy. We are nuanced. We have things happening in our personal lives that may impact our thinking or our disposition or our resting bitch phase when we get to the office. None of us is always everything. But if you think of your boss as having dual roles, then that ship can help more depending on the situation. Sometimes they're a coach, sometimes they're an evaluator. Yes, we want to be, we want to be stretched, we want to get improvement, we want that. We want a coach. We also want someone to say, here's some constructive feedback of where you could be better. Both are necessary to your success. I want you to aim for striving for what I'll call mutual dependence, right? You need them for their success. They need you for the success. You need them for money and growth and whatever you're going for next. Your boss wants to collaborate. They want to lead initiatives. They want you, um, they want you to lead initiatives, they want you to develop your team, they want you to stay current, adaptable, and driving for growth. So, how do you build that relationship and therefore build that trust that you are on those things? I want you to test some low-risk situations, right? So maybe see what the mood is or what the vibe is of your boss. Are they the coach or the evaluator? See which shows up. That will tell you a lot about how they will operate. Asking them questions is a good way for you to see how they respond and therefore understanding are they the coach or are they the evaluator, the judge. Also finding out what's important to them. Are they really big on strategy? Are they big on planning? Are they big on thought leadership, on insight, on first to market, collaboration, consensus, figuring out what is important to them and therefore developing and displaying those skills, assuming that you have those skills, is a way that you can support their goals. And then I want you to think through what do you bring to the department or the unit or the team or the company that is going to make success for everyone? Make sure they see that you bring those things, that you're creating that value. Positioning yourself as an ally to them too, right? There's always a pirate on the ship. If I get promoted and someone gets promoted too, uh-oh, are they going to surpass me, right? This is human nature. These are the things that we think about a lot of times. I've seen so many people weaponize their excellence, that they withhold their best work because, you know, they want to show that the like that that sort of currency, that social currency of information. And their boss almost ends up like begging for the information. It's really hard. Stop gatekeeping, right? Being in that space where you're able to show your boss this is yours, this is ownable, but here are the main points. Again, I've seen this a lot too. Another colleague, another client of mine is in a position where they're recently new into a company and they're finding that one or two of their direct reports are really gatekeeping the information. In the long run, it's not going to work out well for those people. So you don't want to be that person. And when you're in that position, you want to find the way to open it up, let them know that you're not here to do their work, but that you are here to help the entire department grow and that we need that information, right? There's where some of the challenges lie. And that can be the stickiness that can create that tension. So on either side, don't be the dick. Make sure that you're open and sharing and creating allies, both with your boss, both with the people that are below you, whether they report to you or they're um cross-functionally in another department, and then also in your cross-functional leads. This is how you build that relationship. And then lastly, I want you to think about your ability to perform, it is going to be a key factor in creating a solid relationship with your boss. Your results definitely matter. But are you being supportive of your boss, your team, your peers, your direct reports? Are you keeping your boss informed? Are you assuming the best intention? Being generous with people as much as possible at every level. This is where you're assuming people have the best intentions. They are having the best intentions. It's grace, one day at a time. This is what we're doing. The faster you extend it, I'm going to guess the faster you're going to receive it and generate mutually beneficial relationships. Next, thinking about your bosses, the skip level, right? Depending on your organization, this is the person who may ultimately approve your raise, the support for your professional development. And as your role changes, they are going to have a continual broad perspective, not only on the organization, but on the talent pipeline. So, how do you get to know them? You're going to stay in the know. If you're in a meeting with them, make sure you know what's going on within the organization to the best of your ability in the industry. Be up on the latest on news. Don't be asking them things that you can Google or, you know, put into chatty GPT, right? You don't want to be doing that, but you want to make sure that you're up on the inform on the information so that you can provide a very fertile ground for conversation. And then acknowledge wins. Listen, if your skip level has just had a huge win, who doesn't like a compliment? We're all human. Sending them a congratulatory note that has to be genuine, right? It's nice to be neck recognized. We're not going to do something that feels artificial or inauthentic or grandstandy, but hey, you know, I saw you quoted in that article, or hey, I saw you speak at that event. Um, I was really impressed with the way you handled that client situation today. Letting them know those things in a really genuine way, assuming it's genuine, right? We're not just saying things that we don't mean. That is how you're going to create that. You also want to reach out strategically, again, if it's appropriate within your company's culture. You may want to mention that your current boss's name and say, like, I'm working on this with Jill, but I also, you know, wanted to reach out to you so they don't think you're jumping the chain. You may tell your boss you're sending them an email. Um, you're not going to do it without asking permission. You know, you're providing air cover, you're making sure that your boss knows, but there might be an opportunity to ask about something within the industry. Again, this is about being authentic. Maybe they're in an organization that you're thinking of joining. Maybe there's a professional development course that you're thinking of taking. Maybe there's something about a particular project that you're working on where they can be a resource. Again, you want to talk to your current boss and just say, like, listen, I'm going to reach out to Jill because I want to talk to her about this. I'll copy you on the email, right? In a healthy organization, no one's going to stop you from doing that. It just needs to be clear as to why you're reaching out to them and that you're not just jumping the box. All right. What I want you to walk away with out of this is even the most difficult boss can become your ally. It starts with managing your mind, it's getting clear on your strengths, understanding your talk track, letting old patterns go that are not helping you, that are hindering you, and understanding that even if there's some tension, even if there's some friction, your boss is not your energy. They are human. They have their own pressures, their own goals, their own strengths, their own shortcomings. We're all human, right? So when you approach the relationship with generosity, clarity, strategic thinking, this is where you have the opportunity to create the change. Okay. I want to hear from you. Have you been in a situation before? How did you navigate it? If this is helpful, email me what was helpful. Send me a note to uh hello at JillGriffincoaching.com. And as always, if this episode was helpful, please share it with a friend, share it with a colleague. That is how we get the word out, and that is how we create the kind of change that we all want in the workplaces. I want to make workplaces work for everyone. And I want to help people navigate the complexities of today's workplace. And we do this by sharing this work. So I appreciate you. Be in possibility, be intentional, and always, always, always be kind. Okay. I'll see you next week.

unknown 18:42

Bye.