Building Strong Relationships with New Bosses: Practical Advice

Episode Transcript

Hello and welcome to the Daring to Succeed podcast.

My name is Julianna Yau Yorgan and I’m a workplace strategist who teaches leaders how to show their value and increase their impact through compassionate strategy.

Today, I’m going to share some real-world mistakes that some of my staff have made when they were newly reporting to me.

I do this not to shame them, they were actually some of my best staff and progressed really well in their careers, but more of a lessons learned for anyone out there trying to adjust to a new boss.

Even though it’s your boss’s job to properly onboard you, I think these stories can show how even some very, very experienced people have the opportunity to make some adjustments so that those first interactions lead to a better working relationship overall.

So let’s dive in.

Okay, so this first situation was sort of an ongoing issue I had with a one-on-one I had with, well, my one-on-ones that I was having with one of my staff. When we started having them, he basically spent most of our time running me through everything he did for that past week.

And this was really hard for me because my style of one-on-one was really different. I kind of like to have them a little bit more casually, get to know the person, especially at the beginning, and really dive in to focus on what challenges they might be having that I could help them with.

Where could I add value as their leader? So sometimes that might be giving them insights on what’s going on in the company or just working through like an interpersonal issue or trying to figure out how to solve some other problem.

But from what I could tell, this guy was used to doing this like schedule recap of his week with his prior bosses. And even though I would try to kind of take him away from that style, he kept falling back to it. And this went on for a really long time until we broke through and it was really hard for both of us because I could tell he felt unheard.

He seemed to feel like I didn’t really care what he was doing with his day. And on the flip side, I got really impatient and wanted to kind of rush him through that because I just didn’t want to sit there listening to his week and couldn’t figure out how I could help him as his boss.

Like I said, we did eventually move through that and the story here isn’t so much about my specific style and his specific style. It was more that when you start working with a new boss, don’t assume that whatever you did with your former boss in your one-on-ones is going to work for your new boss.

Now obviously the, I don’t know, the reflex or the default would, for most people, I think, be that, hey, this is what I did before, so I’m just gonna keep doing this.

And especially if that’s worked for the last few bosses that you’ve had. Instead, what I really recommend is at those first one-on-ones, kind of share, hey, this is what I used to do with my previous boss. This is what they were looking for. This is the value I got out of it.

And then ask them, hey, does this work for you? Is this also what you’re looking for? And it just opens up the conversation so that you can discuss how the two of you will use your one-on-one time. because I know even having different styles of people reporting to me, some people see that time as, hey, I want to meet with you and get all all these decisions made. Or I had someone else who really used that time to try and figure out, OK, what else is happening in the company? What are you working on? What’s the future plan?

So everybody has something different and you need to make sure you remember that when you go in with your new boss as well that they’re going to have something different that they want out of it than what your previous boss did.

The second situation I had was more of an isolated incident. I don’t even remember specifically what we were talking about or what the situation was, but I remember the conversation was just a little odd because she basically came out and said, blah, blah, blah, but these rules don’t apply to me.

They’re for these other people, not for me. And It was, I guess, a little funny for me because I think she thought she was kind of setting up her boundaries and saying, here’s how I see things. These are my expectations. Let’s get this done.

And because I’m very curious about people and what makes them tick, I didn’t really take it personally, but I could see if she was reporting to someone different, maybe one of my other director peers that Maybe they would take it really personally and immediately get their back up. She’d have a target on her back and basically there’d be like this push and pull of like a power struggle.

And regardless of what it was and regardless of whether it was even true, this kind of thing is really difficult because you don’t want to set up your initial conversation in a way that your boss is already trying to figure out, how do I establish myself as the authority figure in this relationship? Because oftentimes, especially if you have a good boss, they don’t want to tell you what to do. They don’t want to overly do it on the HR stuff.

But if you’re going to put it out there and say, hey, like black and white, this is what I expect. And I expect you to bend the rules for me. You may be in some trouble. Hopefully you’re not necessarily in that situation.

But really, again, what the takeaway here is, if you need accommodation from your boss, especially with all this work from home stuff that’s going on out there, test the waters first. get to know them, get to figure out which rules they are pressured to enforce, how they will work around those situations, and kind of where their line is drawn before you go in hard with a big ask.

And obviously, I don’t know, there’s so many situations where you need accommodations or Maybe you had a special arrangement that wasn’t on paper that you need honored to manage your personal life as well. But again, just tread carefully when you go into these situations because I know some people who feel like if they’re doing that if they’re more assertive that they’re going to be respected by their boss and they’re establishing their boundaries and doing all this right stuff to protect themselves may work but in most cases may backfire terribly.

So whatever it is, kind of piece out what you need and test it out until you get to know your boss well enough to know if you can go in with a direct ask. And then the last situation I have for you is kind of the toughest one for me.

Again, going back to these one-on-one conversations, I often use that time to share what I was working on. And I did this a lot with people who reported to me who wanted to move into the same level I was, that they wanted to move ahead in their careers, and I use this sort of to share with them what type of work they can expect they need to do and the type of thinking that I need to do, the type of strategy I needed to work on. and use it really as like a on-the-job training for hey this is what to expect here’s here’s what you can start thinking about and really make sure it is the type of work that you want to be doing and This was, again, really challenging for me because one of the things I teach is how to work with your boss to understand their stress points, understand the work that they need to do and how you can help them.

And this was difficult because in this particular instance, this guy reporting to me was just overly helpful. And what he’d do is every time I told him about my work, he would just go out there and do a bunch of stuff that he thought was going to help me and then bring it back to me all proud and say, hey, look what I did. I did all this stuff that you can use this.

But oftentimes it backfired for him because I was just thinking, oh my god, like how much time did you just spend on all of this work that I didn’t tell you to do? And why weren’t like, what about all the other stuff you actually had to do? Like even trying to figure out how to have that conversation was so awkward. And eventually when I even got to the point to say, hey, I’m sharing this with you for insight only, please, please, please don’t do anything with it.

Because, like, I actually have to do this for myself and you have all this other work to do. I don’t think you have capacity for it or whatever the conversation was. But no matter how directly I told him to stop, he kept trying to help. And it got to the point where I had to kind of sit down and think, how do I, how do I manage this without simply just cutting him off and not sharing these insights with him anymore?

And, you know, honestly, I think a lot of bosses would have just stopped because, OK, I’m sharing, you’re not responding the way I want you to and you’re cut off. So you don’t want to be trying to be helpful to a point where your boss is afraid to share things with you because you’re going off and doing all this proactive stuff.

What you want to do instead is try to understand if there is an opportunity to help by asking. So I think it would have been really different if I shared all this stuff and he said, hey, would it help you if I did X? or show me maybe a little tiny bit of something to say oh you were you told me about this I kind of was thinking about it could this be helpful to you and if they say no back off And if they say yes, then yeah, go for it.

But it’s, again, very important to test the waters with this new boss to figure out where is their line for how much they want help with, how do they delegate, where do they want you to spend your time? Because as helpful as you think you may be, even if you’re doing it for the best purposes, If you’re doing more than what your boss wants you to do it can be actually really frustrating because again you’re gonna have your job that needs to get done and if you’re doing all this other stuff it’s going to make your boss wonder what you’re doing with your time that is not the job that they’ve hired you to do. So these are just some of the examples of things to do and things to avoid if you’ve got a new boss.

And something I’ve done for my leaders amongst leaders community is I’ve taken my experience with reporting to literally a dozen different managers in my 20 years in corporate and six years of my own experience having staff reporting to me, including managers and project managers, and turned it into a simple workbook for anyone to follow. In the workbook, I go through what conversations to have, cues to watch for, and classic mistakes to avoid and how not to seem like the teacher’s pet. And it includes my exact checklist, scripts, and secrets to put your best foot forward.

And the whole point is to help anyone adjusting to a new boss avoid getting micromanaged before it even starts. figure out whether your new boss is worried about you, and if they are, how to get off their radar, and gain their trust quickly so that you can just get back to focusing on your job and your team. I also go through some tricky situations, kind of like what to do with an interim boss. So these would be bosses that they’ve pulled in for a short period of time before they hire someone long term.

So sometimes this could be somebody that just they’re kind of moving into that spot, or maybe you’re reporting to your boss’s boss for a little bit. I also go through how to handle promises made by your last boss, and I’ve got tons more examples of those. And then as well, especially for all you leaders out there, or people who are trying to get into leadership, what to do if you wanted their job and didn’t get it, because I’ve seen tons of that.

And I’ve also moved into positions where I knew I had people reporting to me who wanted that. So as I was putting this together, I realized it could help anyone who has a new boss, not just other leaders. So I’m offering it to my non-members too. So all of you out there. So if you’re interested in learning more, just check the show notes. I’ve popped a link in there for you.

Okay. That’s it for now. And I guess I’ll see you next time.