She Geeks Out + Datadog Panel: Making the Leap to Manager | Datadog

She Geeks Out + Datadog Panel: Making the Leap to Manager

Published: December 26, 2019

Ami: Hi everyone, I’m Ami.

I work at Game Changer Media.

I interned there, actually, when I was in college and then started right after I graduated, and I’ve been there for over four years now.

I’ve tried a lot of different kinds of engineering there. I started as a frontend developer, then switched to more of a backend focus, then switched to our platform and infrastructure team.

And about five months ago, got a management role.

And so, I started up a small, new team that was in charge of…a new part of the product. That was exciting. And I’ve been a manager since.

Alisha: Hey, everyone. I’m Alisha Sedor. And I feel like the slightly odd one out on the panel in a couple of ways.

The first is that I’m one of those tech-adjacent folks. So, I work at Harry’s. Yes, the men’s razor company that now does more than that.

And I also started as a manager in my very first job, so that’s a slightly different perspective that I guess I’ll bring.

After law school, I worked briefly on a campaign and then took my first big kid job as executive director of NARAL Pro-Choice South Dakota.

So, I went straight into having a team and not knowing what to do with them. I can talk a little about that later.

And when I moved back to the East Coast, I landed at Harry’s a little bit by accident. I was waiting for my New York bar scores to come back, and the temp agency that I was working for at the time introduced me to this crazy little startup that nobody had heard of.

And five years later, I’m still there.

My day job today is as senior manager of quality training and development for our customer experience team. But for the last several months, I’ve actually been focused almost full-time on the integration (we’re combining with Edgewell).

So, we’re going through an acquisition merger right now, and I’m doing internal communications and project management for the integration. (So I don’t sleep very much).

And that’s me.

Shifra: Okay, so our next question probably doesn’t apply to you.

Alisha: It’s okay.

What is the most difficult thing about moving into management?

Shifra: What was the most difficult part of a transition to management since you started as a manager? So, Stephanie, do you want to…?

Stephanie: Sure. I think the biggest difference when you’re transitioning into management is: how do you measure your output and efficacy?

Because when you’re an individual contributor, when you’re a software engineer, or in whatever field, you’re assigned a task, you know the deadline, you know what you’re supposed to accomplish, and you can measure yourself at the end of the day against that.

Similarly, at least when you’re in engineering, you have that satisfaction of, “Oh, I have this problem at the beginning of the day,” and you can put your headphones on and dig in and spend a lot of time just focused in on that and solving it, and feel like, “Hey look, at the end of the day, that’s what I did, and I feel great about it.”

Whereas when you’re a manager, your day is spent doing a lot of different things, and sometimes it can be very hard to say, “Well, what did I actually do today?”

But, the measurement of that efficacy and that impact ends up being over time with the relationships you build, with the direction your team is going, and making sure that people feel like they’re…that they have the context they need to do what they need to do, and that you’re providing that to them.

And so, it just changes, and that’s a hard thing to adapt to just because sometimes it can feel like, “Oh, I don’t actually know what I did,” or “I don’t know how to measure anything.”

But that’s a common feeling a lot of people have.

Ami: Yeah, I would definitely second that one.

I think the feedback loop when you’re a manager is much slower, especially transitioning from engineer to manager. So you don’t really see the output of what you’re doing until like, a couple of weeks or even months later, if at all.

I would say another challenging part for me was definitely figuring out what the components of my job even were.

I think there’s so many different parts of management, and as an engineer, you kind of come in and you have your tickets, and you know exactly what you’re working on for the day.

As a manager, what you’re working on day-to-day (or-week-to-week) can change so drastically.

You have some very people-focused weeks, you have some very code, kind of technical-focused weeks.

And so I think, figuring out what even is under the management umbrella, and then out of that, figuring out what are the most important things for you to be working on day to day is really hard.

Alisha: I will jump in.

So even though my transition was a little different, I think that the hardest part for me was that not only was I a manager and a first-time manager in my first real job, but I also didn’t have a manager, I reported to two boards of directors as executive director of NARAL.

So I had, like, 20 people that were technically my boss, none of whom were really plugged into the day-to-day.

And I think that what I took from that that’s probably applicable to folks that are making that transition no matter where they’re starting from: so I learned how to manage up very quickly, and how to set very clear expectations for myself.

So, on that, “I don’t know what my output is from week to week,” and that changes a lot.

I think I had to be very thorough at documenting what that actually looked like, so I could report back to boards on a monthly basis.

So I think that would be a thing that I would recommend to folks, is get very good at knowing how to clarify what you are doing and capture that, and also share that up to folks and tell them what you need.

Shifra: And one thing I’ll add to that, for those who are in tech itself, I think balancing the coding full-time to managerial is a really hard transition, because to your point, coding feels like you’re getting stuff done, and how do you stay close to the code when you’re not doing it anymore?

Initially you think you’re going to spend half of your time, and then it slowly gets away from you…in my experience anyway.

How does the management transition affect your relationships?

Shifra: So our next question is, were you prepared for how your relationships would change with your peers?

And do you have any good or bad experiences that you would want to highlight?

Stephanie: So when I transitioned into management, I was, as I mentioned, at a startup.

And I think that there are different…where you kind of make that move can be very different depending on the kind of company that you’re at.

And so right now, I’m at LinkedIn, which is a much bigger company that has a full-on program for when somebody wants to transition into management, that you enter and they kind of give you all this training and support for how to manage, how to have one-on-ones, how to talk with your peers and counterparts, and you get coaching, and you have a mentor, and you have all these things.

Whereas when I was at a startup, primarily the reason why I became a manager was because I was on a team and I was like, “Oh my God, this is crazy.”

Nobody knows what they’re doing, nobody knows what’s going on. I could be doing such a better job than the person who I’m theoretically reporting to.

And so you kind of step up (and step into) that role without much in the way of any guidelines about how to do that or what to do.

But, the plus side of that is in that situation, particularly when you’re at an understaffed startup that’s in growth mode, you tend to fill a void that’s needed.

And so when you get into that situation, people tend to recognize like, “Okay, I didn’t think we needed this, but actually we do.”

And so when I was making that move, I think the generation of us who had been there when things were crazy, and messy, and hectic, really respected and understood the necessity for putting better processes into place for those who were more junior and those who were new.

And so, like, our relationship changed from, like, “Hey, we are born in fire, let’s just make this thing work” to “How do we make a system that will work for everybody who comes next?”

But again, that’s very unique to that particular situation.

Whereas when you’re coming up at LinkedIn, or on my team now, if I’m thinking about putting somebody in a manager position, the tendency and the situation is, generally, you have somebody who’s established himself as a leader on the team already, who people respect technically, and you look for them having those kind of leadership skills and talent and try to, you know…so it’s a much more organic…it’s an organic thing, but yeah, their relationship with their peers is going to change.

Ami: Yeah, I would say that since I got a completely new team that had just formed when I became a manager, I didn’t actually experience this as much because I didn’t have that experience of my peers now being the people that report to me.

But I actually found this kind of positive in some ways, because I…when you’re an individual contributor, and you have your peers and your friends, you hear a lot about people’s frustrations and things that you think…that people think the org could be doing better.

And so it was exciting, actually, to finally get a seat at the table, to be able to do something about those frustrations, and to be a little more connected with the people who are expressing them when I got the management position.

So it was actually a pretty positive experience for me, I think.

Alisha: Yeah, I didn’t go through that transition of peer to manager in my first management experience, but at Harry’s, I’ve done that a couple of times.

Or to your point, Stephanie, about things being messy and people moving around, our organization changes all the time.

And so, I think what I’ve found worked really well when I’m going through those transitions at Harry’s (and just in life also) is listen first, change later.

So I always try to come in with the perspective of hearing—to your point, Ami—hearing all of those frustrations before you actually go do anything about it.

And I think that that’s…not only do you have the opportunity to do that as a manager, but the listening part is doubly true and even more important to understand what your team actually needs and wants.

So, not coming in with “Okay, it’s Day 1, here are all the things that I’m going to change and do.” I think that creates a lot of tension.

So, doing a lot of listening tours every time I’m plugging into a new team, or taking on new directs, or making a move to oversee people that I used to work next to has been, like, really fruitful for me.

Shifra: Yeah, and one thing I can add to that, I remember the first time I became a team lead, and I took over an adjacent team, and I’m like, “Well, they all know this better. They’re smarter. They know this.”

And then what I always tell people that I’m mentoring for leadership roles is, “There’s a reason you’ve got the role. So, always keep that in mind, and recognize that.”

What was one memorable mistake you made early in your management career?

Shifra: So, our next question is a fun one. What was a mistake you made early in your management career—and what have you learned from it?

Stephanie: One of you guys can…

Ami: I can start.

Shifra: Yeah, sure.

Alisha: So many. So coming into managing a team in my very first management experience, where I didn’t know what I was doing, and I think that the biggest mistake that I made out of the gate were two interrelated things.

The first is setting really clear expectations for people and just letting them know what I actually need them to be doing.

And then the second is giving candid feedback in a way that is actually setting them up for success, so that they know what they can be doing better.

I actually reached out to two of my former direct reports who I talk to and do chat every day almost still, because we all are very tight from that period.

And I was like, “Hey you all, what did I…”

Can I swear?

Audience: Yeah.

Ami: I was like, “What did I fuck up when I was your manager?”

And they were like, “Well, we had a really good time. It was great. Everything was awesome.”

And I’m like, “No, no, no, tell me what’s up?”

And I think the clear expectations piece was a big one.

And Jenny in particular expressed that, because they weren’t clear, she often felt like she was held to different expectations than her peers.

And I don’t think that that was the case looking back, but it definitely felt that way to her, and that’s what matters.

So, not setting clear expectations and then having that be some of the fallout was something that I messed up pretty big, but I think I’m better at it now.

Ami: I would say one of the mistakes I made early on was just feeling like I couldn’t make any mistakes at all.

So, I would spend so much time and energy preparing feedback, and being ready for meetings, and rehearsing exactly what I was going to say.

And it just ended up taking time away from other things I could be doing, obviously, and it ended up taking a lot of mental energy for feeling like that.

And I felt like anything I did wrong could irreparably ruin my reputation as a manager at the company.

And I think since then I’ve gotten better at feeling like that’s not actually the case and giving myself the space and the room to grow and take risks and make mistakes.

Stephanie: I think one of…I somehow go back on, there was this project that one of…the company when I was sort of transitioning or I’d actually been in management for a little bit at this point.

And it was this project where there were…I had this grandiose scheme about what we would try and accomplish and what we would build, and the end goal and the end thing of what we need, and kind of got the team marching in alignment with that.

But there were all these other things that I didn’t really validate first.

Those were external dependencies or expectations, both from our product partner as well as some commitments we had.

And then this was a team where we were…two products that really were not great to begin with.

And so my vision was, okay, well, we will take the learnings from these two and build something new that will cover…it will cover all of the things that those things are doing badly.

But what I failed to think about was the support footprint of those things.

And so it was like a collision of bad, where I have this vision of like, “Oh, this will be great,” like, “This will all work. This will solve all our problems.”

But the getting there was painful. And it was painful because people were supporting something that was untenable.

And then there were still deadlines, like, externally from people, where they had expectations that something would be done.

I’m like, “No, but you know what…No, we’ll get there.”

So I think it’s one thing to have a vision and a goal, but it’s another to make sure that you’re paying attention to the realities of the day-to-day and to the challenges that your teams are facing.

And iterate, I think, the idea of MVP and the idea of setting realistic expectations and realistic goals, and making sure you validate and challenge all assumptions before you move on a project.

So, maybe that…this is more applicable generally to project management, which is a big part of management in general.

But this was something that I just learned because it ended up being a big slog for people to get something out, and it could have been avoided if I had been a little bit more…the presence of mind.

And also, the other thing that I did was assume that the resources that I had, that was what I could have, and try to make it work with them instead of going to my managers and telling them, “This is what I need to be successful.”

That was another big mistake that I realized.

And I realize now also managing people…the people who are the best are the ones who say, “Actually, this is what I need to be successful,” versus, “I’m going to try and struggle and make it work with what I’ve got.”

And there’s a time for both, but you should at least make it clear what the tradeoffs that you’re making are.

Shifra: So, Alisha, your answer inspired me too, I’ll reach out to my first direct reports. I’m a little scared what they’ll say, but it would, at a minimum, be interesting.

And something I could add. This is a mistake that I’ve found myself making multiple times throughout my career.

As a manager and especially as you become more senior, you forget that the people reporting to you don’t have as much visibility and they don’t see the big picture as much.

So you talk about topics and expect them to understand why you’re doing something.

And don’t take it for granted that they know all the information that you have, they’re not in the same meetings, and basically…it’s your job to make sure they understand.

So, that’s something I…that’s a mistake I found myself making a few times.

Has anyone ever questioned you as a manager—or even you becoming a manager?

Shifra: Did you ever experience a time when someone questioned you as a manager, or becoming a manager?-

Alisha: Myself, every day. Does that count?

Shifra: No.

Alisha: I think to build on your point from earlier, Shifra, so, I thought about this question a little bit. We have the questions in advance, spoiler.

And I couldn’t think…

We have such a supportive environment at Harry’s, and they…so my growth there has been very supportive and people have been like, “Yeah, you can do it,” all the great things.

But when, Shifra, you said, you know, there’s a reason that they put you there, right?

I think that that’s something that all managers, like, if there are folks who are managing people now or thinking about managing, I’m sure you’re questioning, “Do I deserve to take on this role? And what makes me qualified?”

And so, I think the person who questions me as a manager the most is me.

I don’t know, maybe if my directs were in the room, they would say something different, but…And I think the way that I’ve tried to work through that is reminding myself that they’re…you know, smart people put you here.

So, if you trust those smart people, then trust that you can do it, and we’re all faking it together.

So, don’t be afraid to ask for help and lean on each other, and I treat my management role as pretty collaborative.

Like, my directs, it’s not about me telling them what to do all the time.

Of course, we do have some specific things that I’m like, “Yeah, we just have to get this done.”

But my job is really to give them the space and support that they need to chase what they want to do and make the roles their own.

And so, I don’t know, if I’m doing that, then I’m like, “Okay, she’s doing okay as a manager.”

But she’s the…Alisha’s the one that questions my management the most.

Ami: Yeah, I would echo a lot of that.

I think Game Changer has a very kind of similar environment where I don’t feel like people have questioned whether I should be a manager or not.

I think I had a similar experience when I first got into management of questioning if I should be the one in this role.

And I think what helps a lot honestly is that you can’t afford to question yourself really, because a manager has so many responsibilities.

And if you really aren’t living up to them, or if you’re holding back in a meeting when you should be standing up for your team, then you’re not the one that’s going to be hurt by that—your team is going to be hurt by that.

So there’s kind of that responsibility of you need to step up to this role whether or not you’re questioning yourself.

And so, I think that kind of responsibility and knowing that people are counting on me definitely helped me get out of that.

Stephanie: I think it was the hardest when first making that transition from my seat to manager, just for all the reasons that they mentioned in terms of doubt in my own ability to do it.

As well as I think that maybe there are one or two peers who…always that sounds like maybe that person also would have liked the role and they could resent you or the fact that you got that and they didn’t.

And so I think managing those feelings and being able to feel confident and strong enough that the decision that was made was right, that’s something maybe I struggled with a little bit early on, but you kind of have to push forward and get through some of those self-doubt moments and have trust that you know what you’re doing. And as the decision was made, so you just got to charge forward and just write those down in a journal and then close it up and forget it.

Alisha: Sorry, we co-opted your question. A bit of imposter syndrome.

Shifra: No, that’s okay.

And I once…I remember this vividly, this was a very long time ago, and I was promoted to something that I didn’t think I deserved.

And I asked, my boss’s boss, I’m like, “Are you sure? I don’t think I know this space.”

And he said, “It’s intuition. And we trust that you have the intuition to make the right decisions.”

And I’ve thought about that, like it’s been a long time since I got that answer, and it’s helped me.

Would you ever give up being a manager?

Shifra: So, to that point, have you ever thought about going back to being an individual contributor?

Stephanie: You know, I’ve thought about it in mostly sometimes missing the tangible aspect of producing and feeling a little bit removed, and feeling removed from the direct day-to-day technical work.

And so, I’ve considered in sometimes, like, I think being a manager and being in management there’s a lot of…I do ultimately consider myself an introvert, and I think there’s a lot of taxing time of just talking to people and working with people, and time in meetings. And it’s exhausting.

And so there’s something nice about the prospect of like, actually I could even work from home more often or I could have a little bit more flexibility about timing and deadlines and such.

So, I’ve thought about it, but at the end of the day when I think back to being…and I see, and what I wanted, and some of the reasons why I ultimately went into management was wanting to have an insight and wanting to have more visibility into the decisions that were being made and why, as well as the desire both to know people and to coach people, and actually enjoying that aspect of the work, the psychology, the growing people, and the satisfaction and having that impact that scales not just to my work, but to other people’s work.

So I kind of ground it in well, the other’s temptation. And who knows, maybe who’s to say what the future will bring or what will happen then.

But at least right now I feel confident in the management track, and that there’s still more for me to do, and learn, and grow.

So, I’m currently fulfilled, but I would imagine that if for whatever reason that would change, then you have to look into different options and different paths.

Ami: Yeah, I would say the same.

Of course I’ve thought about going back to individual contributor, and I’m never going to close the door on that completely.

I think right now there’s still so much I need to learn about management and still so many places that I actually want to grow, that it’s not really on the forefront of my mind.

But I think we’re lucky in the tech industry that making the move back to individual contributor is not unheard of and people do it all the time, and people make pretty drastic switches back and forth.

And so, I would say that if missing being an IC is what’s stopping you from pursuing a management role, then you definitely shouldn’t let that get in the way because you can definitely after a couple of years or longer move back into the individual contributor role.

And I know people that have gone from CTO to individual contributor too.

And so, it’s never completely out of the question, and I think that’s actually a pretty good attitude to have.

Alisha: Yeah, I’d have to think about what…I’ve not been an IC for an extended period of time ever in my career. So maybe I should try it.

But no, I think I’ve done…

I’m actually having a lot of conversations with my manager who’s a really incredible support and coach right now about my future and my path and what I want to be doing, and I think one of the things that everyone covered over the years of my career and my composite career, because I have a lot of different interests and paths, is that at my core, one of my core motivators is serving others, it’s doing the work to prop up other people.

And one of the most gratifying parts of my job is seeing people learn, and grow, and develop, and take on new things.

Every time someone leaves Harry’s to go do something awesome, you’d think that would make me sad, but it actually makes me really excited.

And so, I think for me, no matter what I end up doing, whether it’s carrying on within our organization, or I’m also trained as a career coach, and do that on the side.

And so even if I went and did that as, like, an IC, as a coach full-time, I’m essentially still managing people through their growth and development.

So, I don’t know that I could ever leave it behind. I don’t know. But I do like the idea of like working from home more, so, yeah.

Shifra: So, this question makes me laugh because my answer is a resounding yes.

When I came today to Datadog, I’d first discussed the role with my boss.

The idea was I was a little burnt out from, like we mentioned, the managing large groups.

And the idea was that I would not have a team, and then on my first day, I found out that I had hired someone the previous week.

So, I now am managing a couple of different teams, but my day-to-day focus is less about…it’s temporary, most of those teams, so, along the theme of you’re given a problem, fix it, so, you know, some people left that we need to replace for this organization to live.

But longer term, I actually hope to be back in an IC role for at least some period of time.

Who were (and are) your mentors? How have they affected your career?

Shifra: Okay, so who are (or were) your mentors, and how have they impacted your growth?

Stephanie: I think mentors come in a variety of forms, and it’s not always what you expect.

And this is something I think I struggle with even as a manager, because one of the conversations you have with people is like, “Oh, I wish I had a mentor.”

And one of the things that’s always happening at companies, and I’ve never really seen it solved in a good way, is they’re always trying to create these inorganic mentorship programs, where you get matched with somebody, and it’s supposed to be like, “Okay, now, this is your mentor.”

And I have rarely, if ever, seen that actually work anywhere, at any time.

Because I think mentorship…to a certain extent is like dating.

You might…meet somebody, and they pair you with somebody, and they’re like, “Oh, this is your mentor,” and you talk to them, and it’s just like, “Well for whatever reason, even though I’m supposed to learn, they’re just not…it doesn’t click,” you don’t have that…

Alisha: Awkward first date.

Stephanie: Awkward first date, right. You’re like, “Oh okay, great, you’re my mentor now…Will you be my mentor?”

But the relationships where it’s been the most impactful are those where you meet somebody, or you see somebody who you look up to for whatever reason, and it can even be a peer, it doesn’t have to be somebody who’s above you.

It’s just somebody who, for whatever reason, you admire the skill set that they have.

So, I might even say that…during my first, I had somebody who I was actually managing at a previous job, who…but she was sort of equivalent seniority but more on an IC path, but always had a lot of insight.

And she was somebody who I could always talk to, and get insight, and get value from those conversations.

And we would help each other…we would lift each other up.

And so that’s almost a mentorship experience.

Whereas now at my current company, I have somebody who is a couple of levels up, who’s a really amazing, like, VP, and he himself has three kids, and he and his wife both work, which you don’t often find.

And so, it’s refreshing for me to actually talk with somebody who is so senior, who is so successful, but who also will talk about potty training his kids, and openly in with this into it, it normalizes those conversations, it makes me feel like this isn’t just a woman thing, this is a thing that’s important.

And he’s also somebody who I really value and look up to from the perspective of how he communicates with his teams, how he leads.

And so that’s, again, not a situation where I was like, “Will you be my mentor?”

And I wouldn’t even know if he would consider that I consider him a mentor, but I do, because every time I sit down and I talk with him, I feel like I’ve gained insight into what I can be doing better and how I can be more strategic, and how I can balance (or not balance) family and work.

So the best advice I have for people who are looking for mentors is don’t go to your boss and be like, “Find me a mentor,” go out and find people that you click with, in whatever regard it is, in whatever part of the organization they are. And go to coffee with them, and just invite them, and then just build that relationship organically.

And you don’t even have to mention the word mentor, just go to those conversations and draw from it what you can because those are the most valuable relationships you’ll have.

Alisha: Yeah, I’ll build on a lot of Stephanie’s sentiments.

So, I think the way that I think about mentors for myself (and the way that I recommend to mentees of mine that they think about mentorship) is to actually have a board of mentors.

I collect people who are good at things that I think are smart and awesome, and then I tap them for stuff when I need advice.

And they don’t know that they’re my mentors, but they are.

And I think early on in my career, when I started at NARAL and I was reporting to two boards of directors, and I had no idea what the hell I was doing, I collected that board of mentors in a few ways.

The first, is that I was lucky enough that the woman who had held that role prior to me, who was much more tenured in her career, she had been a legislator for a number of years and kind of did NARAL like as a fun retirement project almost.

She was still around and available and made herself available to me.

So, I leveraged that relationship to the fullest, and at the same time I had a peer who was working at Planned Parenthood, who had a role that was similar to mine, but not the same.

And I just started hanging out with her all the time and made her go to drinks with me all the time, and really leveraged her knowledge of how to navigate that space and how to work in the South Dakota legislature.

And so, I started to pick some people that I put together, and a lot of those folks are still part of what I call my G-Chat Council, it’s our group chat that I talk to a lot, almost every day.

So, I would say, I think about mentorship that way.

And yeah, to the point around formal mentor programs, they’re really lovely when they work.

So Harry’s just launched one, I think the folks who organized it there are really thoughtful about the way that they’re trying to match folks. So hopefully, we see some really great success there.

I love my mentee and my mentor, so I’m feeling great.

But I’ve also had a mentor in the past through one of those more formal programs who was a delightful human being, but all she wanted to do was set me up on dates.

And that’s very nice, but it wasn’t super helpful for my career.

So, yeah, I think…

And then now, my current mentor, he’d probably turn red if he were in the room. For Harry’s folks, don’t tell Will I think of him as my mentor right now.

But Will Freund, our COO, I kind of dual report because I’m wearing dual hats to our Director of CX, Alejandro, and then Will, who’s our COO, and he and I have had a working relationship for five years now.

And he’s just been an incredible person through this whole process of the integration to make me get really uncomfortable and think about like, “What do I want to be doing? How do I want to turn this experience into something I want to do in the future? Can we dig in on my deep values and motivators?”

And oh God, I would do that, I would talk about other people’s values and motivators all day. But the fact that he makes me sit down and talk about mine makes me really uncomfortable.

But I’m so appreciative for having someone who’s just thinking about me and pushing me to think about me and what I want to do.

So, I wouldn’t tell him, “Yo, you’re my mentor now,” but he is filling that role.

Ami: So, I would say that, and also similar to these two is that it’s happened very organically for me when it does happen, so I think peer mentors are the most underrated type of mentor, but I think that that’s usually where it kind of happens.

And so, a lot of it is just finding someone that you admire or who you think is good at something, and then talking to them about how you can get there or asking them to challenge you and try to make you better.

I think you can really work out if you get a manager that can be your mentor and a manager that you admire.

My manager is right here, so it’s a little awkward. But I think being very, very clear about what you want and where you want to go with your manager is really important.

And I think, just from the start, I was clear about the fact that I wanted to be a manager one day, and so we were able to discuss what opportunities I should take on and what kind of leadership roles I should take on.

And so, it definitely helped my career growth and progression by being very honest about what I wanted, so that we could discuss where I can find opportunities and where I can grow to get to exactly where I wanted to be.

Shifra: I’ll echo pretty much what everyone said, but self-mentorship is what I found that works, and collecting people who can give me advice, etc.

What makes for a good manager?

Shifra: What characteristics or soft skills do you think make a good manager?

Stephanie: So with this question, I think there are two dimensions to it, multiple dimensions.

But the ones that I feel are the most important, first and foremost, you want a manager who is concerned and attentive to making sure that you are growing in your career, and giving feedback, and looking for opportunities for you, and really cares about you and your career, and what you’re trying to accomplish.

So I think that is table stakes for a good manager is somebody who cares.

And I think we’ve all had managers who maybe don’t care, who care about the bottom line of accomplishing things, and they’re not thinking about the people, they’re just thinking about the thing that they’re trying to do.

And when you have that, then it can be a really bad situation.

But the second dimension to that is you can have a manager who’s really thoughtful and caring, but if that manager isn’t effective at setting a strategy and establishing that strategy within the company.

So, your manager needs to be good also at managing up and at navigating the social politics of wherever you are, knowing that those social politics are different everywhere you go, but your manager just needs to be good at navigating and forging that path forward.

Because if they care, but they can’t do that, then they still can’t find opportunities either for themselves or for you to grow.

So, those are the two pieces that I think are really important, are that they care and that they can set a path so that the team can grow.

Ami: Yeah, I definitely agree about the people management part of it and the managing up part of it.

I would also say that a big part of a manager’s job is listening to and synthesizing a ton of information, making decisions off of that and then figuring out who you need to actually communicate those decisions to.

So I think a lot goes into that. I think you need to be able to be an active listener and be able to clarify what people are saying and figure out kind of the root cause of problems and frustrations.

I think being decisive is important.

It is important to get a bunch of different inputs and a bunch of different opinions, but if you’re the kind of manager that can’t ever make a decision, that just ends up frustrating everybody.

So being decisive, and then also being a clear communicator, so making sure that you know exactly who needs to know about each decision, but also being able to communicate it in a way that makes sense.

Yeah, and so active listening, being decisive, being a clear communicator.

But honestly, I think that if you care a lot about your job and you’re willing to work hard, like all of the other things will come, you’ll get better with time, and that all of the other skills will be grown.

So I think just caring and working hard.

Alisha: Yeah, I’ve got a couple of thoughts on this. I agree with everything everyone else is saying, we just love and support each other up here apparently, and just like all think the same things, which is great.

But I would add to that.

So I think, first and foremost for me, as someone who later became trained as a coach and then realized that what I’d been doing for years was coaching, I think coaching and having coaching skills is essential to being a great manager.

I mentioned, you know, that I see my job as propping up my team to go do their jobs well, and I think what that’s about is really understanding what does that mean to them?

And so, creating space to ask more questions, then have answers for people, helps them to learn how to do things themselves.

Like teach a person to fish… Wait, wait, no. Give a person a fish…Whatever that old adage is. Like you want to teach them to fish, not give them the fish.

So, I think coaching skills really allow you to do that by just asking the questions rather than jumping in to try to be the problem solver, which I think as folks, particularly folks who have been very strong ICs, your tendency (and it’s my tendency too, to be clear) is to be the problem solver. I want to fix this for you.

And I think really great managers take that step back and say, “Okay, unpack this for me. Like, what’s going on here? Tell me more about this.” So that you can help them figure out how they would go solve something and not necessarily how you would go solve something.

So, that’s one.

And then I think the other, which is related, is to care very deeply—but take very little personally.

So, I care so much about my team.

But if I’m doing my job well, I’m actually pissing a lot of people off a lot of the time.

And so, I think, you know, to be able to give really direct feedback that ultimately helps people in the long run, that hurts in the short term.

And so, being able to actually deliver that effectively sometimes doesn’t go so great.

But in the long run, you hope that you’re actually developing and growing people well, so you have to care a lot about them in order to do that effectively.

So, care deeply, take very little personally.

Shifra: I was just checking on the time. It seems like we have 10 minutes left. So let’s do one more question and then we’ll jump into FAQ.

Should managers always be upbeat and positive?

Shifra: So there’s a famous quote that goes, “As the leader, it’s your job to be in a good mood every day.” What are your thoughts on that?

Stephanie: I mean, I think that there’s probably a certain amount of…you do want to be the strong person for your team, and you don’t want to let…even when there’s turbulence, you do have to be this strong and steady.

But at the same time, I think that there are times when you do want your team to see that you are both vulnerable and concerned and a person.

And so…also there are times when life might make you not in the best mood or circumstances might make you not in the best state.

And so, I think sometimes also sharing your own vulnerability with your team and your own concerns, or weaknesses, or shortcomings actually makes you more human and makes the conversations that you have more meaningful.

So of course you want to control that, and there are some times when you absolutely need to be that strong person.

But there are other times when you can allow your…whatever is really happening or feelings to come through a bit.

Ami: Yeah, I would say that there’s probably more nuance to this than just being in a good mood all the time.

So I think it is important to be authentic and not be fake because I think people can tell when you’re exuding this fake positivity and it really comes off in a grating way.

But I think it’s really important to be aware of the energy that you’re putting out, because a lot of times people echo the energy that they see from their manager, and so it’s important to know that you’re actually setting the tone for your team in the way you’re communicating decisions and the way you’re talking about stuff.

And I think in general it’s fine to feel frustrated at work and frustration actually reveals a lot of flaws in the process and at the company.

But I think as a manager it’s your job to be proactive about these frustrations and talk about them in a healthy way.

And so, you’re modeling the behavior that you’d want other people to also emulate.

So I think it’s not necessarily about being in a good mood, but it is about being proactive, about being level-headed, about being composed and not letting things get to you too much.

But like this…the fake positivity, I don’t think that that works.

Stephanie: Just with that, I wanted to add one more thing that I thought of that…a lot of the times at work, you’ll have maybe something that really irritates you, or somebody, or some situation.

And I think as a leader it’s really important to shuttle those concerns up and not down.

And I’ve seen…I’ve even had some, like, a very senior IC on my team who had this tendency to just get very frustrated with a thing, or a person, or situation, and then just complain and rattle the team about it.

And everyone gets all rattled.

And I’m like, “Listen, this is not productive. This is not moving anything forward. Like, do this with me, come to our one-on-one and tell me the problem. Tell, and I can echo that upwards, up the chain. But if you’re pushing it down, it’s not solving any problems.”

And so, I think that’s a good mantra to have, which is, “Hey, you’re frustrated with a peer, you’re frustrated with whatever, don’t push that down on the team.”

Ami: And sorry, I would say one last thing, also, is that…

Stephanie: It’s okay.

Ami: I think if the way you’re presenting yourself at work is actually stopping people from being comfortable around you and stopping people from being able to express their frustrations in meetings and to you, then I think that’s when you need to take a step back and reevaluate how you’re presenting yourself.

So, frustration, anger, all of those things are natural, and that’s fine.

But if you’re not good at taking feedback, and if you get really frustrated when that happens, or in meetings, if you’re acting really frustrated or angry, then that’s going to stop other people from being able to contribute, and so that’s when you should kind of pull back and make sure that you change the way you’re behaving and presenting yourself.

Alisha: Agree.

Audience Q+A

Shifra: Okay, we’re going to open the floor…I agree too.

We’re going to open the floor to any questions. Tara’s going to come around with a portable mic. I’ll let you guys answer it.

Person 1: So my question is, when you first became a manager, what was the most beneficial learning and development that you had or wish you had?

Alisha: I wish I’d read Radical Candor like 10 years ago.

And I don’t…it’s not my Bible, I don’t subscribe to every single piece of it, but I think the concept of what you heard probably in my talking points of being able to care for people deeply, making sure that they know that, and then from there, being able to have really direct feedback with folks…that was life changing as a manager when I finally came around to it.

But yeah, I had no L&D for many years.

Ami: Yeah, mine is a book too, it’s Crucial Conversations. That one was recommended to me by multiple people, and it was super, super useful in just one-on-ones with my direct reports and managing ops.

So, I think it’s a lot about treating conversation as an art and making sure that you put a lot of energy in the way you’re conversing with people. And so, that book helped a lot.

Stephanie: I’ll probably double down on something I mentioned earlier, which is making sure to ask for what you need. And if you’re not getting what you need, make it clear what the tradeoffs that you’re making are.

And so you know, if there’s a project and there’s a deadline, say, “Well, either the deadline has to slip, or we need more people, or we have to make some other tradeoffs,” and making it very explicit what you need.

That was something very early in my career, I tried to just say, “Okay, this is what I’ve got, I’m going to make it work, I can do it all,” but you set yourself up for failure.

You set some something up to break, and it will.

Tara: Here you go.

Person 2: Hi. So, I’d like to thank everyone on the panel for sharing their thoughts and experiences.

So, I’ve been hearing a lot about managing up, what does that look like on a day-to-day basis? Like, what are those conversations? What do they entail?

Alisha: Sure. So, for me, it’s essentially about building the same relationships that I have with my direct reports upward toward my manager.

So, creating a space where we both know…so I’m thinking of, well, in this context our COO.

Like, creating a space where we both know that feedback goes both directions and that he can ask me to tell him what he can do better, and I’m obviously receptive to him telling me what I can be doing better.

And so for me, it’s really about creating that space and making it a dialog and not being afraid to speak up, right. So if there’s something that I actually disagree with or that I think we can be doing better, that’s a big part of it.

And the other is being an advocate for my team.

And that, I think, as a manager, it’s not just about me and my needs, but it’s about talking to our CEOs…“Our team isn’t getting X, Y, or Z, and we actually need that.”

So, I know that’s kind of a soft answer, there’s not a template or a format for it from my perspective. But it’s really about just starting to have that dialog and being clear about that, “I’m not going to be quiet about things.”

Stephanie: I think when you’re when you’re an IC, and in general, this is something that’s also often given as coaching advice to women, which is about self-promotion, which is about not just assuming that, “Hey, I’m doing all of this work, and therefore, people know that I’m doing the work and they recognize it.”

It’s about making sure that you’re sending emails, you’re sending status, you’re sending something to represent and echo upwards that, “Hey, this is something that’s getting done, and I’m responsible for doing it.”

When you’re an IC, that’s sort of the guidance they give.

But that trend, that also holds for when you’re managing a team, except it’s now not about me, it’s about my team. It’s making sure that people understand what’s being done, that I’m giving the appropriate call-outs to the individuals on my team.

And then, similarly, also that I’m advocating for the team and advocating for our capabilities so that we make sure that the next opportunity that is being delegated out, they’re saying, “Well, like, I remember that team that did a great job, let’s give them collectively some more responsibility.”

So, it’s about…it’s the extension of self-promotion, it’s team promotion, and team advocacy.

Ami: Yeah, I definitely agree with both of those. And I think the one I would add is also managing expectations for your team, and so making sure that people are very aware of what your team can work on within what time periods.

And also making it…like keeping all of these requests away from your team.

So things that aren’t related to your key team, and things that people want from your team that your team can’t even take on right now are things that you should be talking about when you’re managing up and talking to the people you report to.-

Shifra: Do we have time for one more? One more.

Person 3: Hi. So running off of what Stephanie said of “Just ask for what you want,” so in my previous job, I really wanted to have the growth there and continue with them, but we couldn’t find a number that I was happy with, and I felt that it was kind of below the market value.

And so, I found another company that respected the number that I wanted and hence moved there. I work here, so, love it.

And I’m just curious as what you would do in that situation. I wanted to grow with them, I wanted to stay. Ultimately, I had to find someone that respected my work ethic and the number that I wanted.

Alisha: Yeah, I mean, it sounds like you made the right choice for you. So, congrats on making that money.

I think that in these situations it’s really just about quantifying the growth that you might have gotten at this other place.

So, it is a lot about… I mean, I’m a member of Ladies Get Paid, so I’m all about the money, like go make it.

But also sometimes there are tradeoffs that you’ll make for a learning experience or a growth opportunity that will actually set you up for success in the future.

So, when I started at NARAL as the executive director, I don’t know for folks…a lot of folks are in tech here, so I don’t know if you know what the salary ranges are like in the nonprofit space, but take whatever you make as an entry-level person, and cut that down to about a quarter of that, and that’s what the executive directors are making in a lot of the nonprofits that you look at.

And that was a conscious choice that I made. I was like, “I’m not going to make money for a few years because this is an incredible opportunity to run a team out of the gate and go lobby in the legislature and spend time in DC, and do all sorts of wild and crazy things.”

But that was a choice I had to make to quantify that.

So it’s not exactly parallel, but it sounds like for you it’s here you will also have growth opportunities and the money. So good job.

Ami: Yeah, I think it sounds like you made the right decision.

And I think it definitely is about tradeoffs, but I think you need to figure out, you know, whether it’s money or anything else, like what are your hard limits, and be very clear with your company about what those are.

And if you feel like any one of those is not getting met, then it’s important and it is your responsibility to yourself to tell your manager and your manager’s manager exactly what you need.

And if you don’t get it, then I think that’s when you make the decision that you did.

Stephanie: So, I mentioned in my early career I was working for Goldman Sachs, and then I made the decision to move to a tech startup, which, I think being very clear on the tradeoffs you’re making and why you’re making them and also all of your life circumstances that are happening when that change occurs.

For me, moving…I was at Goldman, which was very comfortable, which was good money, but I was unfulfilled both with the mission of the company as well as my day-to-day, what I was learning, and I felt that were I to stay there the skill set that I was building ultimately would make it so that the only place I could work would be Goldman.

And so, actually making a shift into something that was not going to pay as well, but where I would be learning something completely different and much more marketable skills, that was a tradeoff I made.

And I was also in a position to do that at the time. I wasn’t married, I had no kids. Something I think I’ve mentioned in other conversations is when you can take risks, take them, don’t be afraid.

And again, this is like another thing that I think is…tends to be more of a woman thing, which is being married to a job or married to a place, and being like, “Well, I’ve been here for so long, like, I’m so invested.”

A lot of guys are just like, “All right, up and out,” for whatever reason they’re not married to the position.

You have to look at your career as not not just one upward trajectory, and that there’s not just one way of measuring that, it’s not just about money, it’s about skills.

So what you’re learning, going to a growth startup, you might make less money, but you might have different opportunities to take on more leadership, or to learn how to build something from the ground up, experiences that…like now I’m at LinkedIn, which is a much more stable company, which is…but it also moves slower.

And that’s the way things go and that’s another tradeoff. I could be at a place where, hey, things are moving faster and I’m making less money, but I’m…you just have to make that decision very consciously and think about where you’re trying to get and what is most important to you in that moment.

Shifra: You definitely made the right choice. And have we mentioned that we’re hiring?

Raffle and prizes

Shifra: Okay. And I think with that, we’ll wrap it up, and raffle off some prizes.

Facilitator: Thank you so much, all. So we are going to wrap up with some of our raffle prizes and then we’ll have a chance to network.

So if there’s any questions you didn’t get to ask, you’ll probably get a chance to ask them at the end.

So everyone if you want to pull out your raffle tickets. So how this works: I’m going to show you all the prizes, whoever I pull first will get the first pick of the prizes, and then I’ll pull the next one and so on.

So all the prizes are very geeky because this is She Geeks Out.

So, we have a wine glass that has glasses on it.

We have a Nasty Woman Magnetic Poetry Kit that goes on a fridge.

We have a William Shakespeare party game. It looks like Cards Against Humanity, but all William Shakespeare-esque.

We have a Secret Loves of Geek Girls comic book.

And then we also have some gifts from Datadog.

So, we have a Datadog tote full of goodies.

All right, so first number is…let me make this fair.

Okay. 119389.



Check your tickets again, if not, I’ll pull the next one.

All right.

All right, go to the next one.


Come on up.

All right, you get the first pick.

English teacher. Shakespeare game is gone.

All right.

All right, next ticket.

Come on up.

Wineglass is gone.

Oh yeah, I thought that was going to be the first to go.

All right, next one.

No, it’s fine, I trust you.

Hurray, come on.

Person 4: You know what, it’s funny, I never [inaudible].-

Facilitator: Don’t admit that. Oh, not here. Not here, not here. I won one here once too, and I never win.

Audience: Yeah, that’s it.

All right, so now we have left the Nasty Woman Magnetic Kit and the Geek Girls comic book, which is pretty awesome.

All right.

I know the tension is high in here.

All right.

This table.

Come on.

Person 5: Lucky table.

Facilitator: Come on up. All right, we got the comic book, hardcover, or the poetry kit.

All right, all right.

So for the Nasty Woman Magnetic Poetry Kit, the winner is…119417.

Come on up.

Here you are, winner.

Oh God, I got to shuffle better.

All right, you all, well there is still food over here, we have our panelists to speak to, we have one another to speak to.

Oh, and then one other thing, so this is up to you, but if you are someone with a sticker that is either “I am hiring” or “I am looking,” if y’all want to congregate in this corner over here just so you can…yes, yes over here, Datadog can be over here too.

I know they’re hiring a ton, feel free.

But everyone else feel free to obviously stand wherever you want and talk to whoever you want.

But that will conclude.

Thank you all so much. And thank you so much, Datadog.