From Stuck Senior PM to Director Leading Product | Lynne Levy Coaching Review

In this interview, Phil, a senior product manager who felt stuck and doubted his abilities, shares how Lynne Levy’s Inspired Product Leader (IPL) coaching program transformed his career. After a failed lateral move away from product, Phil’s confidence hit an all‑time low, prompting him to seek external help. A conversation with Lynne, coupled with a success story of a former participant who quickly moved from senior PM to director, convinced him to enroll. Key takeaways from the program include embracing authenticity, revamping personal branding on LinkedIn, and rebuilding confidence. Phil emphasizes that group coaching—through peer feedback, case‑study exercises, and community networking—was the catalyst for his breakthrough, more so than one‑on‑one sessions. The IPL framework helped him create a clear career roadmap, leading to a director role at a startup where he will run the product organization and report to the CEO. Phil credits the program for restoring his self‑belief, teaching him to present his true self, and providing a supportive community that directly contributed to his new position.
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Um, I, I, it helped solidify me or reestablish the confidence I had in myself that I am good at what I do and I am a good product manager and I can be a director. And now I am a very good product manager and I'm a director. That's what I'm— there we go.
So good to see you. How are you?
I'm doing great, Lynne Levy. How are you?
I'm great. I'm so excited that you start your new job in a week or two.
Yeah, I'm, I'm super excited about that too. Can't wait to, can't wait to get going.
So let's dive in. So tell the folks listening, where were you before you decided to start the program?
I was at a point in my career where I knew I wanted to take a next step. And I knew director was the— I wanted to be a director. Of product. That's what I felt I needed. And I remember even asking a manager at the time, telling a manager who was a director above me, you know, I want your job. What can you do to help me get there? So I tacked in my own career and made a decision. I actually left product for a while, for a brief stint, just trying to figure out what came next. And so left product, realized that was a bad move, pivoted back to engineering, pivoted back, excuse me, to product and found myself back in a senior product role and really uncertain of just, I wanted to make that next step, but really unsure, like how to do it. I had made a move that didn't work out. My confidence was ultimately at like an all-time low. I was really questioning, like, are you even good at this product management stuff? Can you even, are you in the right career? Should you be switching careers? What are you thinking? Like every sort of. Question you would ask about whether what you were doing was right. It was what I was asking myself at the time, um, when I found the program.
And what, what made you decide to ultimately say, hell yes, I'm going to invest in myself?
Uh, Lynne, you had reached out to me, um, and we had an amazing conversation, um, where I was just able to sort of articulate to you. And it was, it was great to have somebody who, when I described what I was looking for resonate back and say, okay, yeah, I can help you get there, as opposed to a, okay, we'll talk about that. Like, and then you also had, there was an example, you gave me an example of someone else who was in the product. And it was one of those, like one of your, your, your students who, or, you know, participants who, who had gone from like a senior manager, senior product manager to director, in a fairly, in a matter of months, it wasn't years, this wasn't something that was like, oh my gosh, you need like years of training, like you can reposition yourself. And so those two things, one, finding someone who would listen and contribute back to help me, and then two, seeing that this isn't— you're not years away, Phil, right? Like, this is something you can figure out, were two of the big motivating factors for me to try to sign up for the program. Felt like I needed something.
What were some of the key learnings that really helped transform things?
Oh, without question, the biggest key thing that I still to this day advocate to everybody is your, your message about being your authentic self. I kept— I think what I kept trying to do was figure out, like, how do I fit myself into the role of director? Like, how do I— how do— like, there was a preconceived idea of what it meant, like, and I was, I was like missing a piece, or I was like somehow I was not complete yet. To match that role. So being your authentic self and then having somebody— when somebody tells you like, yeah, that's okay. For some reason, when I hear that about like an area I'm struggling in, it's super helpful. So hearing that like, hey, be yourself. And you know what, if somebody doesn't think that that's right for their job, then you're not right for that job. And that's all right. And there is a job that's going to be right for you. It changed the way I interviewed. It changed the way I talked about like new— or I approached different things even in my current job, but specifically when I was looking for new roles. I just was way more comfortable being myself and acknowledging that if somebody didn't, like, if somebody didn't laugh at my jokes or somebody didn't get what I was saying, like, okay, then you know what, that was a sign not that I'm not right for a director role, but I'm not right for that director role, which was super helpful for me in, um, you know, bounding back and forth. The other thing that really resonated with me was like the the personal branding messages about LinkedIn. And I will not say that my LinkedIn profile at this point is not still a work in progress. It is combining those two things. I have on my product LinkedIn that I'm a strategic leader. I'm a product Jedi. I'm a huge Star Wars fan. I love putting that on my LinkedIn. And again, going back to the authentic, the authentic piece is that if someone looks at that and says like, oh, I don't want this guy, like, great. But if somebody looks at it and says like, oh, I get it. That's cool. I'm like, great, let's talk, right? And just being able to put myself out there like that was, was, and then, and then thirdly, I mentioned that I should say that I talked about the program, like entering the program, my confidence in myself was at an all-time low. And so the other big takeaway was restoring my confidence in, in that I was, I didn't have to consider, am I good at being a product manager?
So I get a lot of people saying, all right, Lynne, I don't know about this whole group coaching thing. Is it— can't we just do a bunch of one-on-ones and it'll work?
Oh, I— the group coaching, honestly, I talked about the confidence. Group coaching is what did it. I mean, that was the thing. That was the big thing for me, the group participation. So, so then one of our one-on-ones were great. I don't want to take away the importance of the one-on-ones. That's super helpful to get that one-on-one, that one-on-one feedback, that one-on-one experience. But for me, the group settings were so helpful because you've got all these two specific things that it really gave me. One, it was great to get outside perspective. I mean, so much of your, or at least for me, so much of my product coaching, my product experiences always come from, you know, work and job experience. And so you're, you're working with people who are in your job or in your field, but to, but to like be bouncing ideas off of them and talking about technology and product solutions and see the commonalities there. And like doing those group exercises, the group exercises were awesome. Like it was basically like the case studies. I mean, those were the things where you're stretching yourself to try to understand, okay, if I'm working at company X and I know nothing about it, how am I going to solve this problem? Or how do I even approach it? And just the validation of one having an idea and having other people tell you like, oh, that's right. Or, oh, what if we did it this way? It like opened opened my mind up to like just thinking differently. It was, it was so beneficial. Like the, the Inspired Product Leader is like a community. I mean, when I was out then doing my job searches, this job, the job that I took, the director job I got, I wouldn't have taken if it weren't for the IPL because I, I wrote a post to the group saying I was looking for— so the job I actually applied to ended up being a director through negotiations of the title, but the job was head of product. It was a small company, and I wouldn't have even applied for it had it not been for a post that I sent out to the ICL community.
And what were you— you were saying earlier, you're on a different trajectory now. So let's talk about that a little bit.
Yeah, yeah. I mean, I went from being— I hate to use the phrase stuck, but it was stuck. I mean, I was a senior product manager for 5 or 6 years. Before that, I was a product manager, as a product manager at other companies, and I just couldn't seem to figure out how to get myself into that, that next level, that leadership, but I just had no idea how to do it. It's amazing. You ask me to build a roadmap, I'll be like, yes, absolutely know how to do that. And then you say, hey, what about building a roadmap for your career? I'd be like, whoa, whoa, whoa, can't build that. No idea.
Exactly.
I don't have any idea how to build that. But with the program, I mean, really, that's what I've been able to do. And, and because I now have a roadmap and a vision for what I want to be, I went from there being totally lost to now having that title of director. And I am going to be running the product organization for a small startup and reporting to the CEO.
Amazing.
That wasn't like— and really the change was going to the program.
Welcome. I am so excited to watch your career. You are such a rock star. You're going to have such an impact on the product managers who report to you because you get it. Thank you, Phil, for doing this. You're a rock star. I can hardly wait to watch your journey.
Awesome. Thank you. Have a good—
thank you. Bye-bye.
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