Homeroom with Sal and Regina Ross - Tuesday, March 8

Hi everyone, Sal Khan here from Khan Academy. Happy International Women's Day! In honor of International Women's Day, we have a special guest, someone who I know quite well, Khan Academy's Chief People Officer, Regina Ross. We're going to talk about her journey and careers, and developing careers as a woman or anyone.

But before we jump into that conversation, I'll give my standard announcement. First of all, a reminder that we are a not-for-profit at Khan Academy, so if you're in a position to do so, please think about going to khanacademy.org/donate. Donations of all sizes make a huge difference. I also want to give a special shout out to many folks who supported Khan Academy, especially when the pandemic hit, and I think we're finally surfacing from it. But it allowed us to really do things like Homeroom and provide support for almost 3x the users that we were seeing when the pandemic hit.

So special thanks to AT&T, General Motors, and Fastly for that, and to all of our other supporters who really keep Khan Academy going as a not-for-profit. Last but not least, a reminder that there's a podcast version of this live stream available wherever you get your podcasts: Homeroom with Sal, the podcast.

And now with that, I'm excited to introduce you to Regina Ross, Khan Academy's Chief People Officer.

"Hey Regina!"

"Hi Sal, I'm glad to be here."

So before we jump into questions, I remind everyone, whether you're watching on YouTube, Facebook, or I believe we're actually live streaming on LinkedIn today, post your questions. Our team members are going to help surface it to me so that I can get to Regina. The topic is about leadership, about managing organizations, etc.

But Regina, I always like to start pretty early in people's journey. If you could tell us a little bit about what you were like as a kid? Where did you grow up? Did you think you would be a Chief People Officer one day? Do you even know what that is? Tell us a little bit about yourself as a child.

"Very interesting question! So I loved and thrived in the academic setting. I was a nerd, a smart kid, loved school. My father was in the military, so we did travel a bit, but then we landed at home in Montgomery, Alabama, and that's where I went to school and graduated. I was part of the gifted program throughout elementary school, and I loved math and science. This really led to my journey into engineering."

"Did you know? You knew I was an engineer, right? That's one of the many reasons we definitely connected on."

"Yeah! I love to travel, and let me just tell you the story. So I was really adept at math and science, and I had a high school chemistry teacher who said, 'Hey Regina, you should attend this Minority Introduction to Engineering program (MITE). It was a two-week introductory program at Auburn University, and that really opened my eyes to the world of engineering because I really didn't know what an engineer was. I was able to explore different disciplines of engineering, and I landed on industrial engineering because I love the intersection of people and processes."

"So I attended Auburn University in Alabama. I didn't want to go too far away from home, but just far enough away. I graduated summa cum laude and started my engineering career. And Sal, I tell you, even though I did engineering—continuous process improvement, mostly in manufacturing—I did transition into operations leadership, sales leadership. You know, I was a Regional Logistics Manager. I have always had a passion for helping people develop, and maybe it's because of the way that my chemistry teacher took an interest in me and said, 'Hey, you can do more.' So that's been my passion for employee engagement and leadership development."

"And I was eventually tapped on the shoulder. I was an operations senior leader at a big box retailer, and they said, 'Hey Regina, we want you to step into HR.' So because of my culture-focused leadership, I took the role, and I fell in love with HR. Some say that I crossed over to the dark side, and I haven't looked back. The thing about HR that I love, Sal, is it really enables me to focus on connecting talent and culture to the business outcomes."

"One thing you didn't know is when I was a junior in college, in pursuing my engineering degree, I wanted to shift majors. I was thinking of being in ministry or being a nun, something! My mom was like, 'No, you're going to finish your engineering degree.' And so it was me stepping into HR years later like, 'Okay, I get it. I'm able to help people; I'm able to drive business outcomes.' Just seeing that connection of my passion and my purpose, I love what I do."

"There's a bunch of really interesting threads there, and just to connect with us because obviously there's a lot of young people watching this—probably young men and women—watching this, probably trying to figure out, 'Okay, is this an interesting path for me? How do I navigate this?' I know in high school and college, everyone has a lot of angst, so like, 'What am I going to do with my life?' It sounds like you found this passion for math and science fairly early on. I think it helped that you had other people believe in you. I definitely resonate with that part of your journey."

"Then industrial engineering, which I don't think a lot of people know, but to your point, it's kind of like how do you optimize a factory? You click on a button on Amazon, now how does that—how do they figure out how to put the right thing in the right package and get it to the right place? Process design, so it's pretty broad. You know, the set of things. Then you went into what you kind of called operations, but that would be more like—it still is process for people in a lot of ways. Then you went into HR, human resources, and I think this is something I think I was naive initially when I was coming straight out of college. I'm like, 'Okay, I'm going to go work for a software company, and that means that a software company does nothing but write software. What do all these other people do?'"

"And I've now realized when you have an organization, human resources, the people function, it's core because it's all about people doing everything. So how do you think about people operations or human resources to someone who is naive like me in my early 20s?"

"You know what? That's what it is, and I was so fortunate, Sal, when I started at a particular company—I won't say the name—but I started as an operations leader. So this is me leaving my engineering career going into operations leadership at a distribution organization. As a senior leader, I had to do some onboarding, and one of the courses was 'Thinking Like an HR Manager.' Like, what? You know, I'm not an HR person! But the way that they put it together is that you're not just leading or managing your business processes; you're leading and managing a team of people who make it happen."

"I had some great mentors who taught me, 'Regina, if you take care of the team, they will take care of the business and take care of the client.' This is why I think I had this culture-focused leadership mindset and approach, that yeah, I'm an operations leader, I'm an engineering leader, but at the end of the day, it's taking care of the people."

"And, Sal, when I stepped into my first full-time HR leader role, the dots really connected, and I saw that potential of really focusing full-time on helping the culture and the people deliver on the business priorities."

"And I will tell you, the Khan Academy job posting that I saw really resonated with me. I didn't have a background in non-profit; I didn't have a background in the educational industry. When I saw the job posting, I thought, 'I don't know if I'm going to be a fit, but there is something in that that kept pulling at me.' And I'm just going to read this verbiage from the job description. It said that this role was to help foster a high-performance culture and a great place to work that enables employees to deliver their best work towards attaining Khan Academy's mission while fulfilling their personal aspirations and career ambitions. Dropped the mic! That was it for me; I was sold. That's what I'm doing. That's why I'm so excited to be here."

"And it's not just that; I love Khan Academy. I love, you know, what we do, and my kids use Khan Academy because even though I'm an engineer, they struggle with math and science, and I'm like, go figure! But I know of the benefit and the beauty of this product and what we do. When I saw this, like the mission and then you, me, and my role in people operations, and actually this statement that I just read, this is now our People Operations Team mission statement about really fostering that high-performance culture, a great place to work that enables employees to deliver their best work. So I'm just excited to be here. I love what I do; I love Khan Academy."

"Now, I think there's a little bit of a lesson in there, which is, you know, your journey already took a couple of turns. And even in that last phase before you came to Khan Academy, there was a little part of you that said, 'Well I've never worked at a non-profit; I wasn't in education.' But this thing really resonated with me, so you were able to kind of not feel impostor syndrome and say, 'I'm going to try.' And as we all know, we were excited to hire you!"

"But you know that reminds me of—I could have never guessed that I would have been in this role either. I remember in business school—the business school I went to—they didn't really fail anyone, but if they did fail someone, they give one, twos, and threes in a class; and the only class that I got a three in was called social entrepreneurship, because no way! I was just—I was so cynical about the not-for-profit sector back then. And you know, fate, destiny, whatever, irony would have it, that this is you know, I plan on doing this the rest of my life now. So I think everyone's life takes these twists and turns."

"I am curious and I always like to get into the head of every now and then—I pretty commonly meet people, teenagers, people early in their careers—and there’s so much uncertainty of what they want to do with their life. If you could go back in time, or at least send a message back in time to 20-year-old Regina or 30-year-old Regina, what would you tell them?"

"Yes, and I'm glad you asked that question because I have spoken to my kids, you know, and other young people that I'm trying to help. So, my tips: One would be to try different experiences versus, you know, just sticking with only one thing and only doing what you know well. So I've been in engineering, I've been in operations leadership, I've been in transportation, I've done sales leadership and like, 'I don't like that! I don't want to do sales leadership.' But it helped me to understand what I liked and what I didn't like, what I was good at, and what I wasn't good at."

"The second thing I would say is build and leverage a really strong support network. I call it a personal board of directors, so you have mentors, sponsors, advisors. My career—I wouldn't be where I am were it not for like my chemistry teacher, who I'm still in touch with, people who taught me strategic planning, people who taught me the unwritten rules of the road in every corporation that I've been at. And so leverage that support network."

"One thing specifically for women is that we tend to build relationships, but according to 'How Women Rise' by Sally Helgeson, we don't leverage those. We think it's not good for us to reach out and ask for help. So we've got to build our network and leverage the network."

"I would say another tip or lesson learned throughout my career is excel at the right things. So I can't be perfect at everything; I know that I'm good at project management and some things I'm not so good at, you know, maybe email management and so it's about excelling at the right things. Focus on what matters most. Particularly when you go into an organization and you're building your career, find out what's really important."

"I've seen other women—and I myself have fallen into the trap of sometimes just being heads down and just trying to get a lot of work done. You burn the candle at both ends, you're trying to do a lot of work but you're not focusing on what really matters the most."

"Another tip is know your worth and advocate for yourself. This is something specifically for women. There are a lot of studies, but one in particular is "Women in the Workplace" by McKinsey and Lean In, where there's just the gap. This is why we're celebrating on International Women's Day, you know, hashtag break the bias. So know your worth; advocate for yourself. Typically, men will negotiate when it comes to salary time or for promotions, and women—we don't! It's just really important to make sure that you know what it is that you want, that you advocate for yourself, and you prepare yourself for that journey and for those greater things."

"And this, Sal, one sounds so important. I think this last one is really defining success on your own terms versus just avoiding the comparison trap. My journey may be very different than someone else's journey, and that's okay. I have taken a lot of twists and turns in my career and in my development. I wasn't really focused on chasing the title or the promotion or, you know, making this move here; it was about me and my experiences, my total quality of life."

"I’m thankful and grateful for where I landed, but I tell you, there are times where I look to the left and look to the right like, 'Oh, I should be at this level by now,' or 'This person is doing that,' and I just really had to, you know, let me define success for myself."

"One thing I would say for younger people is that they think they've got to have it all mapped out early on, and you really don’t. My kids struggled with this; they were stressed out because maybe as a junior in high school they didn’t know exactly what colleges they were going to go to and what they wanted to major in. This is a tool that I found maybe five or six years ago, but it's a Japanese concept called 'Ikigai,' a Japanese term that means 'reason for being.' I wish I had this years ago, but what it does—and this Ikigai is like a Venn diagram where you're looking to find that intersection between what you love doing, what the world needs, what you're good at, and then what you can be paid for. When you find that intersection, that's that sweet spot or that Ikigai—your reason for being."

"We're like, 'Okay, I'm doing what I love. I'm doing what I can be paid for,' you know, because some people want to do a certain career but then they can't make a living at it. And so if you can find that sweet spot, you are golden. Even if you can't find that sweet spot in one job—and this will be the last thing I'll say, Sal, and turn it back over to you. One thing I learned from one of my managers when I was a young engineer was, 'Regina, you may not find everything that you need and get everything you need out of this job, so make sure that you have other outlets for your talents, for your interests, for your passions.'"

"And this is where, you know, you get into volunteering or you do some things on the side that fuel your passion, so that you're not getting frustrated because you expect to get everything out of that one job or out of that first job, and then you realize that you're not getting everything that you want. So those would be my lessons to the younger Regina. I wish I would have known these things years ago."

"I love it! Just to summarize it because I think you could write a book about this, Regina: You know, personal board of directors, but don't just have them; leverage them. Advocate for yourself; do things sustainably so you don't burn both ends; find your own swim lane. That's what I strongly, strongly believe. I wasn't really happy in my career side until I had my own—now I have almost, I have a very my own swim lane; I was in a very competitive swim lane before as a hedge fund analyst."

"And no matter how much you succeed there, when you define yourself by comparison in that swim lane, you're just never going to be really happy. So I love that swim lane. And that last piece is I often give a version of that to a lot of young people—just make sure you always have room for your passions. No one job is going to be able to check all the boxes, and so you’re kind of overloading it and setting it, making it unsustainable if you project everything onto it."

"One question, you know, this is something that I've struggled with in my own career, and you mentioned this especially important for a lot of young women is to advocate for yourself, and it’s often hard when you’re in the moment to say, 'How hard do I advocate for myself? How hardball do I play?' Because there is a point where if you play too hardball people say, 'I'm sorry.' And I've often seen this even at Khan Academy. Like, at Khan Academy as you know, we take great pains to say, 'Look, if someone's going to be doing a job at a certain level, this is what we're going to pay them,' and we have gotten in this situation where someone has told us their comp expectation is 'X,' and we're like, 'Well, this job, we're going to pay you more!' So it’s not that we don’t want to negotiate; we actually— we’re going to try to pay everyone what’s fair."

"Because even though you could probably get away in the short term with paying someone less if they thought that that’s what they were worth, at some point, they’re going to ask their friends; they’re going to realize that they were being undercompensated. And even the people who are going to be paid more for the same job are like, 'Wait, this isn't a fair place; maybe I'm also being taken advantage of somehow.' So as an organization, it super makes sense to pay if people are doing the same level, same performance, same job—pay them the same, and be transparent about it."

"But you know, sometimes we have had situations where people are like, 'Well, I need to negotiate harder,' and we're trying to be very transparent, saying, 'No, we literally give the same pay, so we don’t want to be based on negotiations.' So what advice do you have to someone where it’s like they want to negotiate; they want to make sure they’re not taken advantage of, which I completely agree, but also there could be situations where it might be less productive?"

"I would say, one, do your research so you'll be well-informed because you may be asking for a number that's just really unrealistic. So, you know, do your research, be informed, and then know for yourself like what are the non-negotiables? What are you willing to concede? Because that puts you in the power of choice, so you're not like, 'Oh, they only gave me this and I had to accept this.' I coach a lot of young women; I know you're not having to accept this. You need to make a choice. Are you choosing to accept it or are you not?"

"And so maybe you want this number and your bare minimum is, 'You know what? I think I could be satisfied here.' Then you make that decision of, 'I'm going to be satisfied here,' or 'I'm going to push for here,' and if I don't get this level, then I'm willing to walk. But you’ve got to have that internal dialogue and be very clear about what your limits are, what your non-negotiables are, and stand in that power of choice so you're not feeling like, 'They did this to me,' or 'They made me.' No! You have a choice; you always have a choice. Either you accept it or you don’t."

"Yeah, no, it’s really powerful! I think throughout life, whether it’s negotiating compensation or just everything in life, it is this. I still find this tension of how much do I advocate versus how much do I accept? It is a hard tension, but I think—the way I think—being informed is the right thing. You know, ask as many questions, get zero in, and then know what you really want—know what you really want to deserve. Don’t go into something if you’re feeling kind of bad about it on day one, thinking, 'I’m underselling myself.' That’s not going to set anyone up for success."

"And I'll say on the organizational side, you know, this is what we try to do, and you know Regina, you and I have a lot of conversations about this—how do we make compensation more transparent so you can give people the confidence that, because the worst thing you want is to be in an organization or an environment where you're wondering all the time of like, 'Well, was this right? Am I going to be taken advantage of?'"

"Yeah, and you want to look at the total picture—not just your base salary, but your overall rewards: your time off, your benefits, your quality of life, you know, the type of environment. I have been in so many environments now where we describe it as the golden handcuffs. Well, yeah, I'm getting a big salary, you know, a lot of stock and all that, but it's a toxic environment! So you've got to look at success for you in terms of like total rewards, life experience, quality of life—all of that—and make the right decision for you."

"It makes a ton of sense! Well, we have some questions going on here. So I think this is a question a lot of people are wondering. This is from Stephanie on social media: 'With the pandemic having gone on two years now, what advice would you give to people who are feeling burned out in their job, career, etc.?'"

"Yeah, I really like that question from you, Stephanie! This whole Ikigai exercise—like really taking that time to be introspective of what do I really want? What am I passionate about? What do I feel my purpose is? Am I, you know, in a space where I can achieve that? And if not, then evaluate: do I need to make some changes?"

"Sometimes it may need to be a job shift; sometimes it may need to be putting some boundaries, you know, in your personal life. But I think we just don't know. We think this year is going to be a great year and we see still just more emotional trauma that we're all having to deal with. Evaluate what you need, and then determine what steps actionably that you can take to get what you need—whether it's boundaries, whether it's getting additional help, whether it's doing something that feeds your passion in volunteering—because the answer may look very different from you, Stephanie, than someone else."

"That's great advice. And Regina, you know these homerooms, especially when I talk to really interesting guests like you, go way faster than I ever… but we're already running low on time. But maybe just, you know, if you could kind of take us out with—you heard Stephanie's question. I think at all stages of people's careers there's just like, 'Am I doing the right thing?' Yes, all jobs have certain things that you know you're not super pumped about, but it has other things that are good. How have you navigated it? When do you know it’s time to switch versus time to just perceive what you're doing differently or try to tweak what you're doing within the job? Or any other advice that you have for young professionals or women everywhere?"

"Yeah, one, so a couple of things: One is have your own personal mission statement. This is something that I learned from 'The 7 Habits of Highly Effective People.' Like, have my own personal mission statement and then continually evaluate—where am I? Am I tracking towards that or am I not? Is the job that I'm doing, the role that I'm serving, the way that I'm living, is it in alignment with that mission statement? Am I moving towards my purpose or am I not?"

"Sometimes we have detours, and I just say evaluate the pluses and the deltas in your current situation. Do the pluses outweigh the deltas, or vice versa? If the deltas or the negatives outweigh the pluses, then it may be time for a change. And you are the only person who can determine that."

"There's a great person, Dr. Kim, who says, 'If you always do what you've always done, then you'll always get what you've always got.' Only you can determine if that is enough. So this is what I would leave you with: evaluate where you're going; is it enough? And if it's not, make a change."

"I love that! If you could send me that quote, there’s obviously a true quote, but there's something about the phrasing that is very poignant."

"Well, Regina, thank you so much for taking the time out. I think as everyone can tell, I feel blessed, and Khan Academy is blessed to have you as our Chief People Officer. I look forward to going on this journey together—both helping support the team at Khan Academy in our journey to hopefully support tens or hundreds of millions of people around the world, but also be able to do things like this and share your wisdom with, you know, so many other people on the planet."

"Thank you! I'm so glad to be here."

"Well, thanks everyone for joining. I know I haven’t been doing these Homerooms too frequently; I'll try to do a few more more frequently. It's no longer the daily Homeroom—definitely when we started doing them in the pandemic—but I hope you got as inspired as I did from Regina. And I gotta say, as someone I work very closely with on a day-to-day basis, I've already learned so, so much from her."

"And you know, this is one of the best things about my job: getting to work with Regina and people like Regina and how we can then empower others. So with that, see you later! Onward!"