The 3 biggest challenges leaders face when trying to get promoted

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As a leader, the path to getting to the next level is very gray. In fact, there is no path. You have to go and make it up, but the most common thing I hear is “I don’t know how.” Listen in this week and learn the 3 biggest barriers leaders face when trying to get promoted. It’s easier than you think when you start taking your thinking to the next level. Listen and learn.

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Hey, I’m Lindsay Lyman. I worked almost 12 years at Amazon and saw so many brilliant and successful overachievers burn themselves out and leave their jobs because they’re so stressed and anxious. But guess what? Having a successful career does not have to be at the expense of your mental sanity and personal time. There’s an easier way, and I can show you how. Let’s do this.


Hey y’all, how you doing? Happy 2024. I personally don’t buy into the whole New Year’s resolution thing, mainly because when I’ve used it in the past, it’s just another way for me to set unrealistic expectations for myself and feel bad about myself. So I’ve decided I don’t do New Year’s resolutions. I can use any day as a new day to reset if I want. It doesn’t need to be January 1st. So if you struggle with New Year’s resolutions, I grant you permission to join with me and not do them. You’re the boss of you.


Today we’re going to talk about the three biggest barriers I see with senior leaders as you’re trying to move up to the next level. I’ve been talking and working with quite a few people in this scenario. It’s funny because I see this common thread of usually, we believe the problem is, “You don’t know how,” and what happens a lot of times is their leaders mean well, but they give terrible advice that’s not very helpful either. It’ll be really specific and really vague at the same time, or just totally vague, right? So it’ll be something really vague like, “Just take things up a notch. You’re doing great. Just take it up a notch.” Okay, that means absolutely nothing. Or again, it’ll be specific but still vague of like, “Just start speaking up more. Focus more on the strategy. Get out of the day-to-day.” Scale what you’re doing. They’re meaning well and trying to help; it’s just not helpful.


And in its very simplest form, I think there’s three main things we need to do when trying to get from one senior level to the next senior level. It doesn’t matter the company; it doesn’t matter how senior you are. It comes down to basically doing more of what you’re doing with less oversight and less handholding, getting better at working through the noise, so like working on the right things, not getting caught up in all of the noise of everything, and knowing how to balance when to focus on strategy and when to focus on execution. So in its very simplest form, trying to grow your leadership position to a higher leadership position requires kind of those three things in the right flavor, in the right form, according to your area of expertise and your company.


But I want to talk about the three things really keeping people stuck from figuring it out. Okay, so the first one is you are believing your own excuse. You’re believing the excuse, but how? Stop waiting for the step-by-step guide and go figure it out. Figuring it out is literally how you get to the next level. If you’re already at the top of that “how to progress” chain, the way you make up the next level of progression is you make up how to get there. There’s never going to be a clear roadmap, but here’s the thing: we’re not just managing your career anymore. We’re leading it. You’ve got to go try some things and make it up.


Okay, here’s what I hear you saying: you’re like, “Great, I get it in theory, but I don’t know what to try.” Again, this is a lie. This is an excuse. You’ve got to stop believing your own excuses. Your brain wants to feel good right now. It wants to keep itself safe, and it wants to conserve as much energy as it can. Trying to think of something new and figure out how and make it up goes against all of this, and that’s okay. You can do it. Stop believing the lies of “You don’t know how” and “You don’t know what to try” or “Where to start.” When we believe these lies, our brain tells it to us, and we just accept it and we give up, and we quit, and we move on, and we stay in confusion and overwhelm and uncertainty, and then we just get restless and frustrated because we’re not progressing, and we start becoming the victim and blame everyone else and everything else.


You do know what to try. You probably just have a lot of judgment about it. Is this good enough? Is this the right thing? Will this actually work? I don’t know if we can do this. Here’s what you want to do: write down all of the ideas of what you could try. Then ask yourself, “What else? But what else? But what if I did know? What if I just guessed?” Make a list. Your brain is going to want to tell you, “I don’t know, I don’t know, I don’t know.” Let that thought come and let it go, because we’re no longer believing that lie, and we’re going to be like, “No, but I think I do know. I’m just not sure yet. What if I just guessed? What if I made something up?” Your brain will start to go to work. Your brain loves a problem to solve. Don’t let it get off the hook with “I don’t know.”


I’ll give you an example. So the other day, I was sitting down as I was working on some things I want to do in my business in 2024, and I was really going back and forth with my brain on trying to figure out how do I get my message out to more people? How do I help more people? My brain was like, “I don’t know, just keep doing what you’re doing.” Again, I know that’s a lie, so I was like, “Okay, I’m just going to guess. I’m going to write it down.” You have to allow yourself to write down all of the ideas that are dumb and stupid and not great and that you would never do in a million years to let your brain get those thoughts out of the way. Let it have all the judgment and keep pushing your brain to be like, “What else? What else?”


So as I started to write down some of these ideas, this is where my brain went. Some of these ideas are terrible, and I would never do them, and I would not encourage anyone else to do them, but they’re ideas my brain came up with, so I just wrote them down. Just because I write it down doesn’t mean I have to go and do it. I’m just trying to give my brain permission to give me the idea because the idea is in my brain.


So as I was trying to figure out how do I get this message out to more people, I’m like, “Well, I could try to go on other people’s podcasts. I can invite key strategic guests on my podcasts. I could do more paid ads. I could try to speak at conferences. I could send more emails. I could post on social more. I could hire an entire marketing team to do all of it for me. I could go out and just copy and steal other people’s ideas.” Again, not what I’d recommend doing, but I’m just letting my brain come up with ideas. I could reach out to different tech associations and see what I could do to help them. I could cold call people. I could email people. I could write a book. I could start publishing articles weekly. I could start an online streaming show. I could create my own community. I could figure out Twitch and go have my own streaming channel. I could reach out to HR companies and offer free help. I could ask my network. I could create a referral program. I could do print ads.


Do you see how my brain just starts coming up with all these ideas? Again, not all of them are great, and not all of them are things I’m going to go and do, but I just want to help my brain see it’s a lie I don’t know what to do.


Let’s look at it in a work setting since not all of you are trying to grow your own business out there. Let’s say you wanted to get promoted to the next level. Okay, you’re already kind of a senior person wanting to get to that next senior level. I saw this a lot at Amazon between the L6 level. The L6 is a lot of like catch-all. There’s a very wide range of capabilities, I will say, within that L6 level. But to get to the L6 to L7 was a hurdle because it’s not as clear of a path, and L7 to L8 was even more of a hurdle I saw. But you know, essentially, you need to come up with some big idea or own some big project, own most of it, deliver it pretty independently, and deliver impact. Crap’s going to go down 100%, but you show up and who you are along the way is actually what will get you promoted. You want those obstacles to come because if it just goes smoothly, no one believes it was like a big hard project.


Okay, so if you know you need to come up with some sort of a big idea like this, I get it, your brain’s going to be like, “Well, I don’t know. I don’t know what to do. I don’t have time. How do I do this?” No, stop believing the lies. Go write down 10 gaps you see that your team is dealing with. Then go identify 10 more. Yeah, your brain is going to want to tell you, “I don’t know.” Remember, just be like, “Okay, we’re just going to guess. These can be terrible ideas. It’s okay. We have to let the terrible ones come.”


Then for each of those gaps, go write down 10 things you could do to help close those gaps. Watch your brain. Okay, it’s going to want to tell you why this is hard, why it’s not possible, why this is a terrible idea. I just like to remind myself, “Yes, and terrible, hard, not possible ideas are very welcome here. Bring them all on. I’m not fighting with my brain. I’m not arguing with my brain. I’m agreeing with it, and I’m encouraging it because it reduces the stress and pressure on my brain to come up with the perfect, amazing, most wonderful, fabulous ever idea and just lets me come up with tons of ideas until finally one comes, and I’m like, ‘Ooh, you know, maybe that one might be good.’ It’s just this little glimmer. It’s not this amazing, fabulous moment, right? We’re just looking for those ideas that have a little glimmer of like, ‘Oh, maybe I could go try that.'”


One thing is, you’re trying to shift from a senior leader to an even more senior leader. Stop believing the lies you need to take your thinking to the next level. You’ve got to get out of the habit of thinking, “I don’t know.” Erase it from your vocabulary. Every time my brain tells me, “I don’t know,” I quickly follow it up with the word “yet.” I don’t know yet. I don’t know yet. It gives me permission. I’m trying to get that phrase out of my brain. You need to get out of the habit of thinking, “I don’t know,” and accepting that answer and moving on. Do not accept it as an answer. Tell yourself, “I’m not sure yet. I want to figure it out. I know one thing I could try. I’ll figure it out one step at a time. There’s no rush. I want to go make it up. I love creating things. This is going to be fun.”


The first thing you’ve got to overcome is stop believing lies your brain is telling you. The second barrier I see from senior leaders struggling to get to that next leadership level is you believe once you get to that next level, you’re going to feel better. And it may in bits and pieces, and it may for a time, but it’s also going to be hard because there’s no magic. You’ve arrived, and all of a sudden things are amazing. That’s not how it works. Here’s the thing: your brain’s going to believe once you have the title and promotion, then you’re going to feel more confident to speak up and voice your opinion in those meetings. But guess what? It’s not true. In order for you to have the title and promotion, you’ve got to learn how do you feel more confident and start speaking up in those meetings today.


Your brain’s going to believe, “Yeah, but once I have the scope of work, then I’m going to feel valued and appreciated and important.” No, you’ve got to go learn how do you feel valued and appreciated and important today to go and make up that scope of work that you’re going to go and create and own. Your brain’s going to want to tell you, “Once we have more money, then we’re going to feel more secure in our job.” No, you’ve got to learn how to feel more secure in your job today so that you can go and make more money. Your brain’s going to want to tell you, “Once you’ve figured out how to get promoted, then you’re going to start feeling more motivated again.” No, you’ve got to learn how to feel motivated right now so that you can start figuring out how to get promoted. Stop doing things backward. It’s not “have, do, feel”; it’s “feel, do, have.” Learning how to create that feeling you think you’re going to have once you quote-unquote “arrive,” learning to create that feeling right now is how you get there. It’s where you’re able to figure out the one next step and go and do it.


So the first barrier is you’ve got to stop believing lies your brain is telling you, and second, you’ve got to stop doing things backward. The third one is you need to start to acknowledge the reward and satisfaction. It’s different. It’s so much more simple and more grounded and more satisfying and more deep and more powerful and more there all the time because the reward and satisfaction of getting to that next level, guess what? It’s really not money. More money, if you’re already a senior leader living a certain lifestyle, more money isn’t going to substantially change that. It’s not really the title and more scope. That is not where the reward and satisfaction comes in because, yes, people may treat you differently, but guess what? People are going to treat you differently. They’re going to expect different things from you. They’re going to scrutinize every word you say in a different way.


The reward and satisfaction, it’s totally different. It’s about how you help and the purpose of what you’re doing now, adding value and helping in what you’re doing. It may be in the actual product or service that you’re doing, or it might be in who you are and how you help along the way. It doesn’t mean you have to be working in a field that’s saving lives and doing these big, crazy things. That may be where you’re at, which is amazing, but the reward and satisfaction can also come from who you’re being, how you show up, how you treat people, how you help people, how you make it easier, how you make it more fun, how you make it more inclusive, how you improve things along the way. That’s where reward and satisfaction comes in.


For me personally, there’s nothing more satisfying than helping someone feel seen and important and needed, helping them get to that emotional state for themselves is the most satisfying thing for me. It’s not money. It’s not title. It’s not followers. It’s not fame. It really is that deep, grounded, very simple, satisfying feeling of “I like who I was, and I feel like I’m helping people along the way.” Maybe that satisfaction is going to come from teaching other leaders how to be better leaders. Maybe it comes from removing unnecessary operational overhead. Maybe it comes from getting really good at managing all the changes above you so the team doesn’t churn and they can do their job. You’ve got to acknowledge the more senior you get, the less tangible the reward and satisfaction is, which is a beautiful thing. Stop looking for intangible things. Notice the intangible reward and satisfaction you already have and go for more of it.


So the three things I see people struggle with if you’re already a leader trying to become a more senior leader is one, you’re believing your own lies; two, you’re doing it backward and waiting to feel better when; and three, you’re looking for the reward and satisfaction in tangible things. I know the more senior you get, the more challenging it becomes, the fewer peers you have, the more pressure there is, but it really comes down to taking your thinking to the next level. That is what is going to enable you to figure out how to keep growing and be that calm, confident leader we all need. You’re amazing. You got this. We’ll talk soon.


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Hey, I’m Lindsay Lyman

I spent the last ~12 years growing my career at Amazon. I’ve built teams, launched new products, and created my own jobs. As a certified coach, I teach people how to manage the noise in their head to feel motivated and valued at work again.

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