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Making the Leap from Tactical Contributor to Strategic Leader | That’s a Good Question

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Making the transition from being a tactical contributor to a strategic leader can be daunting, especially if you have limited experience managing others. So what do you do when you’ve proven yourself and want to take your career to the next level but others making the decisions don’t see it that way?

In this episode of That’s a Good Question, our listener finds herself in this very position. Between workload overload and feeling under-valued, unsupported, and frustrated she ultimately resigned to prioritize her self-preservation.

Through active problem solving, practical advice and shared experiences, Celeste and special guest Ellen Lee offer tips and tricks to help our listener navigate a job search and make the leap into leadership — or determine if her next leap is a career change all around.

 


Guest Expert: Ellen Lee

Ellen LeeEllen Lee, TPM Director, has been leading large scale engineering programs at Google for over 18 years. In her tenure at Google, Ellen has helped to build Google’s first data centers as part of the Technical Infrastructure organization and is known for growing robust, execution driven Program Management Organizations inside of Geo and now for Core. As a T/PgM Steering Committee member, she is an ardent advocate for the value T/PgMs bring to Google’s overall success. Ellen is a strong advocate for building inclusive and diverse teams. She serves as DEI Council chair for Core and is the executive sponsor for Grow with Google’s first ever Project Management Certificate Program. Ellen is a founding member of Tech Advisors and plays an active role in advising and mentoring the next generation of Google leaders.

Our Host: Celeste Headlee

Celeste HeadleeCeleste Headlee is a communication and human nature expert, and an award-winning journalist. She is a professional speaker, and also the author of Speaking of Race: Why Everybody Needs to Talk About Racism—and How to Do It, Do Nothing, Heard Mentality, and We Need to Talk. In her twenty-year career in public radio, she has been the executive producer of On Second Thought at Georgia Public Radio, and anchored programs including Tell Me More, Talk of the Nation, All Things Considered, and Weekend Edition. She also served as cohost of the national morning news show The Takeaway from PRI and WNYC, and anchored presidential coverage in 2012 for PBS World Channel. Headlee’s TEDx talk sharing ten ways to have a better conversation has over twenty million total views to date. @CelesteHeadlee

 


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Episode Transcript:

Celeste Headlee:

Okay. So we’ll begin Natasha with you. And I want to hear some details about what it is that’s happening that has brought you to us. What’s going on?

Natasha:

Yes. Thank you Celeste. So I emailed with my problem, my issue. And it’s basically for really over five years. I’ve been working in more or less individual contributor roles for a couple different organizations. And most recently the organization that I worked for, I expressed during my interview that the reason for leaving my previous role was that I wanted to have more strategic responsibility and have the ability to lead a team or at least a person.

Because I rose through having been an analyst and over five years and rose like to a senior or manager level. And I was interviewing for a director executive compensation position. And so I expressed that in my interview and was told, “Yep, it’s definitely something we can consider. No problem.”

While once I joined the organization, I put my head down, learned I needed to do and thought I was doing a pretty good job. Had a few system implementations that needed to be completed. And I went through all of that. And after about a year, I raised a concern again about wanting to add a head count so I could be more strategic in my work. That really wasn’t addressed or well received.

And eventually at some point soon before I left, I was told, well, this is a one person job. And we’ve talked to other people in the industry and they’re doing the same thing. And I’m pretty sure it was conveniently other companies who were doing the same thing. But they are other organization who actually have a full executive compensation team. And so that left me really frustrated and I felt I had no choice other than to just exit and find a position that was more in line with what I was looking to do.

There was also the toll on family. It was a lot of long hours because all the responsibility fell on me. Vacations. If I took a vacation, work would pile up because I was the expert on exec comp and equity administration. And so taking a vacation was like punishment and it just… It didn’t need to be that way.

And so I have left that organization as I mentioned. And I’m currently looking for an opportunity that will help me to move to that next level. Have that people leadership responsibility, be able to be more strategic in my work. And also not get burnt out because I’m the only person doing the work.

Celeste Headlee:

So, I mean I’m so glad that you’ve brought this question to us. Because this is an issue that is facing all of corporate America, which is an epidemic of burn out. And that was happening before the pandemic, actually. The WHO was warning the world about an epidemic of burn out looming in 2019.

So I want to bring Ellen Lee in immediately so we can talk about these so called one per person jobs that aren’t actually feasible for one person. Ellen Lee has been leading engineering programs at Google for more than 18 years. She’s exactly the right person to talk about this. So Ellen, hello. And thanks for joining us.

Ellen Lee:

Hi, thanks for having me.

Celeste Headlee:

So can we begin just with this idea of one-person jobs and how it gets decided how much one person can handle?

Ellen Lee:

Yeah. I think it’s actually a very interesting phenomenon. It’s oftentimes starts as a one person job. And as person picks up, is able to do more, that gets… The work gets, it’s piles on, or the scope broadens, I should say. And sometimes also as other people leave, right? Then you end up picking up a little bit more. You pick up a little bit more. And the next you know, you’re doing two people’s job, or it certainly feels that way.

And I think what sometimes gets us in trouble here is that we just say, “Well, I don’t have a choice.” And so now what the job that maybe I started with, doesn’t quite look like the job I have now. But we don’t think that again, there’s an option. And one of the things that I do try to help folks identify is, well, write it all down. Be really clear as to what your job is now. Again, not the job that you signed up for originally. But what is the job now. And then look and compare them. And that is a conversation you can have with your leadership around, do you all see that this is now a different job?

Celeste Headlee:

It’s difficult I imagine. And I’ll bring Natasha in immediately to talk about how these conversations have gone. But Ellen, I know it’s difficult when there’s too much space between the people that’s making these decisions about what is a one person job and what isn’t and the job itself, right? That job may have evolved to become quite large if you can’t even and take vacation. That’s a real problem. But if someone isn’t doing that job and is in leadership, and so they haven’t done that level job for a very long time, how do you go about informing them that they are ignorant here?

Ellen Lee:

Yeah. And I think that’s where being able to articulate, right? And yes, I’ve certainly heard that where you have somebody saying, “Hey, this is the job.” And you have somebody in leadership saying, “Well, 20 years ago when I did that job, it only took five minutes.” So being able to have the conversation, having the data, having being able to show, yes, you’re right. Five minutes ago, but that was when the team was 10 people. And now we have a thousand people. And so the job is much harder.

Natasha:

And that’s so true because the population… Ellen is, I’m sure you can relate to over the years, you do have more and more people coming in to what, at least the population that I was responsible for was executives and everyone who was receiving an equity award. And over the years, that population continues to increase as that becomes a more and more popular vehicle to attract and retain employees.

And so every year, that population is growing between five and 10%. And you’re right. It may have been okay as a one person job. Perfect example with the company I worked for prior to that. I joined the company knowing it was a one person job. And so I actually left thinking, well, that it’s going to be hard to convince this company. And so let me take my skills elsewhere, where I can at least communicate that I am looking for that next level.

And Ellen, I see that you were, or that you are part of the DI Council. You’re the chair for Google Core. And one of the things about my situation that frustrated me even more was just the fact that I was one of maybe… Well, not maybe. I was one of two people of color on my team. And I didn’t have any direct reports. Every other person who was at my level did. I had people who were below my level, a couple of managers, a level down, who also had direct reports.

 So it… That part of the situation frustrated me even more because I couldn’t help but wonder, is there an element to this that is based on my race. That, is that a factor? Don’t want to play the race card. But that is how I felt. And that, based on the facts, it just seemed really strange to me that that wasn’t a consideration to have everyone at the same level, have direct reports except for this one person of color on your team. So I just wonder how have you dealt with that kind of situation in your experience with managing and creating diverse teams?

Ellen Lee:

Yeah. I think… I guess without understanding the structure of your organization, were the peers… You said the people at your level who had teams, were they all doing similar type roles? Were those functions viewed as one person roles, or were they viewed as this is a team role?

Natasha:

Well, those were… I think one of them historically had been a one person role. And then that person justified getting a direct report. And then there was a larger team that had just always been… The broad based compensation team had always been on the larger side. And so, the way that I got worked on, honestly, was I would get a couple of people on the broad base to help me with certain things, with certain projects.

And so there was the opportunity for me to delegate that work. But without having a dedicated person, it just was a challenge. I would just have to get help when I could, which wasn’t always convenient.

Ellen Lee:

It strikes me that there’s two pieces here. There is this part about your ability to get all the work done as just one person. That there’s simply too much work and that wasn’t recognized by your leadership team. But you were actually resourceful and you found people from this other team to help you and get the work done. So that’s one is just simply the workload, there was a mismatch between the workload and the capacity, right? So that’s one.

The second thing though you’re talking about is management and having a direct report, which could solve the first problem, right? If there was recognition that there was too much work, then yes. Clearly you needed another person to help you. But I want to talk about that as there’s the, again, the need based. Meaning again, in order to get the work done, you needed to have a direct report. And then there is the, well, everyone else has a direct report. So what does that say about me? And I’m curious. And maybe Celeste, you can jump in on this point. Because I’m curious about that.

Celeste Headlee:

So here’s… Let me ask a question that I imagine a lot of people can find relevant here. Ellen, how is a woman of color… There’s all three women of color right here on this podcast right now.

Ellen Lee:

Yes.

Celeste Headlee:

And we know perfectly well that there’s a lot of gas lighting that goes on in workplaces. Especially of women and especially of women of color. How do we know when we are being overworked, undervalued or held back because of our gender, because of our race? As opposed to that just being part of the dysfunction in our workplace. How do we know?

Ellen Lee:

Yeah. I mean, that’s such a good question. I think that, as I reflect back on my career… Because I’ve had… People have asked me this question. I’m in technology. Oftentimes I’m the only woman in a room. Less so these days. And certainly at Google there’s a lot more women in the workplace. But earlier on, people would ask me, they’d say, “Are you treated differently?” And I thought about it a lot. I used to say no. But then I was like, well, how would I know, right? How would I know? I’m not in the room when people are acting differently. How would I know that they aren’t treating me differently?

And so, one of the things is really trying to have everything be… As I think Natasha mentioned, somebody else was able to justify the need to add somebody. I would be looking at, okay, what did they present? And if I present the same thing, maybe why am I having a different outcome? And so being able to say, if I tried to do the same things, should I be able to be judged the same way and have a similar outcome?

Celeste Headlee:

Natasha, there appears to me to be not only this problem of not knowing whether you’re being treated differently for completely unfair reasons. But there’s also this very pressing problem of a job that you cannot, not only it sounds like you can’t accomplish it efficiently and effectively without having damage to your wellbeing, but also, I can’t imagine how you could move ahead to get training to be in a management position, advance your career development while you’re completely overwhelmed and buried by work. Is that accurate?

Natasha:

That’s correct. Yes.

Celeste Headlee:

So Ellen, maybe we can deal with that piece first. This piece of trying to communicate in an effective way, meaning that you’re actually heard. The reality of the job duties and that Natasha needs support.

Ellen Lee:

Yeah. Absolutely. This is fairly common. I think especially if… Like in my role as a program manager, our job is to keep everything together. And so it feels like complaining that I can’t keep it all together means I’m failing at my job. So in our role, we tend to just suck it up and just do it, right? We’re just trying to get everything done. The downside of that is then the leadership looks and they go, “Oh, okay. Great.” Ellen took care of it, right? Natasha took care of it. I guess it’s a one person job.”

And so there’s something here about being able to say, “Here’s the heroics, right? Here’s everything I had to do to deliver this thing. And it was not a one person job. And here’s how you’re…” But sometimes we’re just so in the middle of getting everything done, we just don’t have time to talk about that. We don’t want to…

And sometimes we… I would say maybe as a woman of color, sometimes I feel like I shouldn’t be talking about how hard it was. Because maybe that makes it look like maybe I’m not as good at this job. But I think realizing though it’s just the work is too much for one person. Not just too much for me, Ellen. But too much for one person. I think being able to make that distinction is important.

Natasha:

That’s true. Yeah. Because there were several nights working till 3:00 AM and weekends. And I guess, when your husband says to you, “This is ridiculous. Just quit.” Then you know there’s a problem. And that’s where it got. It wasn’t…

Celeste Headlee:

How has it gone for you in the past Natasha when you brought up these issues with leadership?

Natasha:

It… So I’ll talk about in my previous job prior to this one that I left most recently. It wasn’t really well received. But I chalked it up to, well, I joined that organization as an analyst and that’s just how it was at the time. I didn’t really know what I was getting into. And to be quite honest, that job was a lot more manageable than this next one. So even though I was doing the job by myself, I got… I rose from being an analyst. And by the time I left, I was a senior manager. So I had several promotions. But with each promotion, it was still just me with the more senior person on the team.

And so I figured in that situation, it would be difficult to convince otherwise. Because that was the job I was hired for, right? I was hired into an individual contributor job. I thought that having been promoted a couple of times that that would justify me getting a hire. I did get an analyst for a few months. So I at least got that with that job. But then eventually I did leave because there was a change in leadership and it wasn’t quite a good fit anymore. And so I didn’t have success in that situation.

But when I interviewed for the next job, which is the most recent one that we’re talking about here, I did express that in my interview. And so I felt that that was known, right? Prior to me even taking the job, that was known that is what I wanted to do. I did want to have the opportunity to lead a team, a person at least, and be more strategic. So I felt more justified in making that request and it… And when the workload became unbearable as it did, I just felt there was no other choice.

So, like I said, there were different levels of leadership and the decision had to come from further up the chain. And just not having that knowledge of what goes into everything that I did, I believe was a factor.

Ellen Lee:

So it sounds like Natasha though you tried to explain that there was just way too much work. Is that correct?

Natasha:

I did. Yep.

Ellen Lee:

And they-

Natasha:

I sure did.

Ellen Lee:

Did they just… They just didn’t understand that or did they actually challenge that? How… What was that conversation?

Natasha:

So the one conversation that I alluded to earlier, that was just, that was the end for me when I was told, “Well, this is a one person job and that’s not going to change.” So that changed from when I had interviewed and I brought that up and it was like, “Yeah, that’s something that we’ll consider.” So at that point I realized, okay, this is no longer something that’s going to be considered. It’s just not going to happen. And I was told other companies are doing the same thing, right? Other people, other companies have this as a one person’s job.

Well, that’s just not true. Because yes, sure. They are companies who have it as a one person job. And there are others that don’t. And so it was just one of those blankets statements.

Celeste Headlee:

Yeah. I’m always skeptical of anytime someone says, this is how it’s done. But also really good research shows that black women in particular are more ambitious, more likely to say they want to advance than average. But less likely to find mentors that help them. This is also often true of Asian American women. And I wonder Ellen if it might be useful at this point for Natasha to find a mentor, an advocate?

Ellen Lee:

Yeah. Absolutely. I think that having a mentor and certainly an advocate or a sponsor in the organization, right? Somebody who has visibility into the work that you do and you’ve done can help to at least provide more visibility into what you’re doing. So when they say… When somebody in leadership says, “I don’t know. I think this is a one person job.” There’s somebody else who can say, “Well, I’ve seen the work and it’s more.” Right? More than one person can do.

But Celeste, if you’re referring to mentorship even outside of the organization, I think having someone to help brainstorm ways to talk to the leadership team about your challenges, right? Absolutely, I think would be very helpful. Is that something you have Celeste? Oh, sorry, Natasha.

Natasha:

Not officially. It’s interesting. Since I left the company, I’ve had a couple people who have really latched on and are just determined to help me in my surge which is really encouraging. These are people outside of the company that I worked with. A couple vendors actually for systems that I implemented.

And so that’s been encouraging. But I don’t have a go to mentor or person. And that’s something that I was hoping to find in this organization. It was a fairly large organization. But I feel like I was just always head down and getting work done and didn’t really have time for that. So that’s something I definitely recognize is key to have a sponsor in your organization and something I’d be looking for.

And Ellen, I also wanted to ask how… Both Ellen and Celeste, how did you get past that initial? It’s probably been several years now. But that initial… Because what I’m going through, I’m looking for a job where I want to have management responsibility. Not necessarily on day one, but eventually.

So how do you get past that hurdle of, “Well, you don’t have people leadership experience. We’re looking for someone with people leadership experience.” How do you… I communicate that’s what I’m looking for. And I’ve had… I’ve managed people indirectly. I’ve had an intern. But how do you get past that as a hurdle in applying for jobs and interviewing when the question comes up about your people leadership experience?

Ellen Lee:

Yeah. That’s a great question, right? How can you be qualified for a role, right? If you’ve never had that experience. But how are you going to get that experience if you’re never offered that opportunity? That’s a great question. And I think the way I’m going to answer this though might… I don’t know how this will land though with this conversation. Because I don’t think of people leadership as only meaning you’re leading a team of people who report it to you, right?

So in my mind, people leadership is you’re leading whether it’s… You mentioned Natasha that you, for some of your projects, you were able to get resources from another team. You also earlier said you’ve indirectly managed or led people. And that means you have a vision, you have a plan, you’re getting the group together to work on something together. That’s people leadership.

And so when people say, “Do you have people leadership experience?” You can say, “Well, I don’t have direct people management experience, but here’s how I have led people. Here’s how I have coached and mentored people. Here’s how I have… Right? You… If you have those experiences, then you should certainly be able to talk about them. If you don’t, which I mean, maybe you have some but not enough, then the next role you find, if it’s an individual contributor role, maybe it’s finding the opportunities to do that type of leadership there.

So again, they don’t have to report to you. In fact, what I found is, if you can get followership from people who don’t report to you, that’s even more powerful. Because here are people who say, “Yeah. Natasha’s my leader. I don’t report to her. But I will… I believe that she is a wonderful leader and that’s incredibly powerful.

Celeste Headlee:

I would also just give a couple more suggestions here because the way that I was able to break through that ceiling, I did a couple things. Number one, I found opportunities for myself, like short term projects that I could do where I could lead people. And so I made the opportunities myself.

The other thing I did is I went out and then I got training with some people who then acted as my references for my people leading skills. I found some management training, some leadership training, and then the leaders of those workshops were the people speaking for me and my references as I tried to advance forward. And it really worked out because they’re trainers. So their word meant something.

But Ellen is, I mean, of these ideas, is all about giving yourself the qualifications and not waiting for someone else to say you’re qualified. You’re ready. But you saying I am ready. And so I’m going to go ahead and do this, which I highly, highly recommend. But I would also say that finding yourself an advocate within, even if you don’t find a mentor within the organization you’re in right away, finding an advocate, someone who even if they’re on the same level as you, or someone who might attend the same meetings, someone who backs you up can be really valuable.

Ellen Lee:

Right. Exactly. And I think… I know you’ve already left that company. But you mentioned that the person who ran a team that had these resources you would tap into, right? That might have been a person who [inaudible 00:28:18] and had said, yeah. I mean, Natasha is already leading these folks. And being able to speak to your capabilities and your skills there.

Celeste Headlee:

Yes. Absolutely. We’re getting ready to wrap up. I wonder Natasha, if there were any last questions you want to ask? Or Ellen, any last bits of golden wisdom that we could get from you?

Ellen Lee:

Why don’t I let Natasha go first?

Natasha:

Yeah. And I know just… Like Celeste said, any nuggets of wisdom I would appreciate. I am going through the job search process and obviously being very selective because I know what I’m looking for and I definitely won’t make the mistake of going into a situation where I will end up being an individual contributor again. So I just want to hear from you Ellen. Any words of advice in terms of how to target my search? How to present what I’m looking for in terms of the leadership opportunity, strategic work and just…

I think what I’m finding is, there’s always that lingering question in the back of people’s minds where maybe it’s paranoia on my part. Why did you leave that job? I’m finding it’s easier to get a job when you have a job. But in my situation, I just… I had to make that decision and here I am. Any words of advice you can share would be appreciated.

Ellen Lee:

Yeah. I think I’m going to talk more generally about, when you’re looking for a role, there’s… Keep it mind that you’re looking for something. But you’re also offering something. And on the hiring side, they’re looking for something and they’re also offering something. And so being very clear, like in this case, if you’re saying I am looking for an opportunity to manage a team. But really be clear on what it is you’re offering too.

Because then, if that’s the thing they really want, they want your expertise around equity and exec compensation. And you know how to do this. And you’ve done this many times and you’re an expert, right? Then being able to say, “Hey, here’s what I’m going to bring to you. And with a team, here’s this amazing work that I can do.” Right? If you… If it’s just me, I can do X, Y, Z. But if I have a team, because I have a vision of what I want to do, you’ll get all this extra.

And maybe that’s one of the ways you can start the conversation so that it’s… So that it’s also about what you’re offering and not just what they’re looking for versus going into a role where they’re saying, “Hey, we’re looking for a one… It’s a one person role. We’re looking for someone to come in and do this.” If they’re starting there and they’re not interested on all the extras you can do with the team, well then you’ll know on day one, that’s just… Maybe it’s not a fit for where you want to go. If that makes sense.

Natasha:

Yes. That makes sense. And I’ve had those conversations and we’ve agreed to go separate ways. Hence, I’m still looking.

Celeste Headlee:

I want to say thank to Natasha, because this question that you brought is I’m sure something that a lot of other women are grappling with. A lot of other people are grappling with at this point. And thanks of course to Ellen Lee. Thanks for joining us and giving some advice to someone who really can use it.

Ellen Lee:

Absolutely. I hope this was helpful. And thank you for having me. It’s such a wonderful program. I’m so excited to be part of it.

 

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