From Work to Home Ep. 5: Getting Uncomfortable, Seeking Help, and Setting Boundaries with Meenakshi Dhingra

[00:45] Introducing today's guest, Meenakshi Dhingra
[01:54] Keeping up with new things
[07:31] Balancing family and personal time
[10:06] Rejecting the status quo
[11:59] Getting the right kind of help
[14:29] Engineering boundaries with Stripe
[17:13] On leadership and rewards
[19:03] Moving countries, transition phases
[22:26] Settling down in a new country
[25:25] An advice, parent to parent
[26:52] Connect with Meenakshi

TRANSCRIPTION

[00:00 Qin En] 

Hi, I am Qin En, and this is the Parents in Tech Podcast.

In this special collaboration series with Stripe, the financial infrastructure platform for businesses, I speak with parents at Stripe on how they create work-life integration and balance their career ambitions with family aspirations.

In this episode, I speak with Meenakshi from Stripe's User Operations team. Meenakshi is a mother to two children, aged 13 and nine.

[00:45 Qin En] 

Hi, Meenakshi. Welcome to the show. To begin with, could you tell us a bit more about your family?

[00:51 Meenakshi] 

Sure. Thank you for having me. It's the four of us, my husband and my two boys who are aged 13 years old and nine years old.

[01:00 Qin En] 

Beautiful. So in the teenage years, how is it like being the mom of two going to be teenage boys?

[01:06 Meenakshi] 

Oh my God. It's constant learning and recalibrating. It's much easier when they're younger. You have to just take care of their physiological needs: feeding them, putting them to sleep, and making sure they are safe.

And now suddenly there are so many other things that you need to take care of from emotions to aspirations, to keeping them grounded. So it's learning.

[01:27 Qin En] 

Yeah. I guess it's all part of the journey. But also as a parent, sometimes the phase you're in all this doesn't seem to be the best. I don't know for me, I have a young daughter.

Right. And I can't wait for her to grow up so she can be more independent, but I'm sure. You also sort of miss the days when they were younger and a lot simpler to care for. You earlier also mentioned, Meenakshi, that you had to learn and keep up with new things. So maybe tell me what is one thing that you had to learn reading.

[01:54 Meenakshi] 

Well, I joined Stripe last year and I changed industries after being 13 years in one company in online advertising. So I think just making the switch to a new company, learning a whole new industry and such a complex product was a pretty uphill task. And I don't think I've done one and a half years into it.

Stripe is moving so fast and we are growing so quickly that there's always much more to learn, pretty much that.

[02:23 Qin En] 

That's incredible, but you got to tell me the story of what led to the switch, especially since it must have been quite a big position to make, right? Leaving the advertising industry after 13 years, what was going through your head at that point?

[02:36 Meenakshi] 

Indeed. And I would say there were two things I was trying to do. Number one, anytime I've chosen a career or a role or a switch, I'm trying to always balance that equation of learning with the impact I'm making. While at my previous company, I think I was very comfortable that was making a high impact. I was learning, but I wasn't feeling challenged enough and I thought it was time to get uncomfortable again and just challenge myself and see if I still have got that learning muscle in me.

So I think that was kind of one big consideration of just doing something which is new, uncomfortable, and just an unexplored territory. Secondly, when we think about careers, which are 30, 40 years long, depending on how much you want to work, it's important to sort of gain that breadth of experience across different companies, different cultures, different industries, and this is my sort of attempt to move, to see things from a different lens and just learn from that.

[03:38 Qin En] 

Got it. So of all the companies and all of the industries you could have joined, why Stripe?

[03:44 Meenakshi] 

I would say I am pretty bullish on where FinTech is going and I was very bullish on where online advertising and e-commerce were 10 years ago when I joined Google.

I strongly think FinTech is just getting started. Online payments are just 12% of the total payment volume in the world. And there's such a huge opportunity ahead of us. So I felt I want to kind of go join violets early and ride that wave of learning and growth.

[04:11 Qin En] 

That's beautiful. So now that you have joined Stripe, how do you explain Stripe to your children?

[04:19 Meenakshi] 

That's an interesting one. When I first joined Stripe and told my kids that I was changing companies and that I'm going to Stripe. My younger one who's now nine, but was then seven, jumped in tech. "Oh, you and joining Sprite, that company that makes the drink. And we are going to have an unlimited supply of those bottles at home."

And he was super happy. Uh, so it was after the party that I tried to explain to them that it wasn't Sprite. Though we could buy the drinks. We're taken care of. Um, it was Stripe. And what I told them was, "Look, Stripe is like a postman that Alexia lottos and sort of delivers them to any country. Any address. And you don't have to worry about once you post on kind of whether it will be deceived, they just do it perfectly and efficiently."

I also told them when a new building or a new township comes up and you need a new post office or a postbox, Stripe does that for you. So you just let them know that you need a solution and they will put that post box where people can post their letters. That was interesting because then we could actually kind of look at some websites and say, okay, it's actually meant for the online world. But I think that analogy, letters, and postman were what I tried the first time.

[05:35 Qin En] 

I love that. It's such a simple to understand such a relatable analogy, but I think it's also so true to what the start mission and mandate are on trying to disrupt the FinTech space.

So the question that I have therefore is about changing careers, changing industries, and companies. I'm sure that was a very steep learning curve. Maybe talk to me a bit about how you brought yourself up to speed quickly.

[05:58 Meenakshi] 

I would start by saying it was an uphill task. It's never easy, but once you kind of start planning your days around learning and impact and start balancing that equation, it becomes routine and becomes a habit.

For me when I first joined Stripe, the first 30 to 60 days, we were really going deeper into product and seeking to understand why certain things are done. Why are they valuable and why do we exist? And what's the sort of purpose and vision and mission? And there's just so much to understand, but at the same time as a newbie, you also bring in that fresh perspective on why not three other ways.

For me, just going back to those first principles and asking those basic questions has been a way of learning more going deeper, but also sometimes challenging the status quo and moving to a point where you are changing things for good. In mind, mental culture is such that we allow people the flexibility to experiment, fail and succeed and let them be.

But I would say it does take quite a bit of time to get comfortable. The other thing I would say is for me, a big belief is you learn best when you do things firsthand. So though I joined as a manager on the team, I started doing some of the tickets or support cases that the team was doing firsthand. And there's no better way to learn than interacting with your users, understanding their pain points, and then going and finding answers sometimes the hard way. But that's tremendous.

[07:31 Qin En] 

I love the part where you just roll up your sleeves, get your hands dirty and come in with a low or no ego that you do the work. Also so you can really understand what your team goes through. Now, the part that I'm curious about actually here, it's about, I'm sure you've learned a lot on the job, but there are also elements that you have to learn off the job.

How do you balance that with your family time, your personal time, because I feel like, in your previous role where you were comfortable, you were experienced, you're very well knowledgeable? Of course, you will still have to keep up with things, but also when you're in a new role, right? 

Tell me, how do you navigate that balance? Especially in the first few months of joining Stripe.

[08:08 Meenakshi] 

I think it's a perpetual effort to balance two careers, two kids, and a job switch. So it's multiple balls up in the air. And then you're trying to catch some at a time or leave some for the other. And just kind of speaking personally, my partner and I, are super enrolled as parents and I wouldn't want my job to switch to becoming in the way of me helping them with homework or attending parent-teacher meetings or just being there in the moments that they need me.

And then both of us as personalities are deeply career-oriented. That learning phase is great. But as a leader, it's also very uncomfortable that you don't know what your team is doing.

And you just want to be short about the detection that you are doing because you're impacting so many others. So I think so to manage this all, one thing that we've had going is a common calendar between us. 

We sit down and diligently work on a Saturday. So we locked down like our big events, our big schedules. Work-wise. Travel-wise and also kind of where the kids need us. And there's a different color coding depending on whether both of us need to be there. One person can take turns and the other ones, and sometimes very simple things like who's going to pack lunch and snack in the morning. 'Cause, the other person is kind of doing some meetings or study time or who has a night call and the other putting them to bed.

It's all on a calendar and it's all on our phones, very tactical, but has really kept us sane on those things. The other part is just, I know, operating as allies and sort of giving each other that space. When I started at Stripe and I really did. I spend the time at work. I know he was stepping it up so much in terms of taking care of kids and taking care of the house and kind of everything else.

And then when he's traveling or he's having those tough periods, I take the flexibility or I take my turn to sort of support.

[10:06 Qin En] 

I really love that equal partnership where both of you come together very collaboratively and make a very conscious effort to make it work. I don't think it's like creating a calendar of personal events to some, I saw like, oh, wow.

Like why did we go to such great lengths, but it clearly has worked for you. So on that note, I'm curious about what is perhaps a status quo as a mum, or even as a dad, when you look at your husband, that you reject?

[10:32 Meenakshi] 

Traditionally as a society, I grew up in a very conservative society back in India, where women do not go to college. I was the first girl in my town, which has a population of about 4 million people to ever go do engineering. So my journey of challenging the status quo started at a very young age. Typically women either become teachers or nurses or just become housewives. So starting engineering 20 years ago was a big challenge to the status quo.

And I remember sort of, kind of having a lot of debates within the family and why that was the right thing to do or why that was the right risk to take. But the status quo that I continued to challenge is that you cannot have it all. Like sometimes we think, oh, you can either be a great parent or you can have a great career or you can be a great partner, but doing it all is tough.

And I think just shaking that belief and saying, okay, I can have it all. I may not be perfect at times, but I'm going to seek help. I'm going to forgive myself, but I'm going to just try and desire and make all of this my own, makes a big difference to how you show up in every part of your life.

[11:41 Qin En] 

Yeah. And I think a big part that you've mentioned over there, it's so seeking the help of course seeking to help from your spouse. That's one. But also tell me a bit more about the help that you have gotten both at the workplace and also at home, especially when both of your sons were younger. That's where I'm sure a lot of that came in. What did it look like for you?

[11:59 Meenakshi] 

Sure. 

I think when my kids were growing up, I actually did not have a lot of like family help.

So we were living far from where our family was, so I didn't have the luxury of kind of grandparents around. Back in India, 10 years ago, or 12 years ago, even the daycares or the formal childcare network wasn't that trustworthy. You can leave the child there for two to three hours, but living with them for a full day was unheard of.

Two things that helped us: one, I would say it was a blessing to be in the tech industry. My husband worked at Microsoft at that time and I was at Google and we just worked out our schedules in such a way that we had to drop our kids at daycare only for three hours. I would start really early in the morning at like six o'clock and be home by three.

When he would only leave at 12, and he'll be home by nine. And we used to see each other only on the weekends. But that's the trade-off that you make because you want to keep it going. And you also want to spend that quality time with your child. I also saw a lot of help. I would say from people I was working with.

One thing I still do and I used to do when my kids were young was to define my non-working hours. But people typically define working hours. So that's a bit of a departure, but my concept was except those four or five hours when I'm a dedicated mom and I'm not doing anything else.

Other times I'll be around, I can make midnight work, but probably I cannot make 6 PM work, because that's kind of my peak time in the park. Some of that has stayed through till now. And when you set those boundaries and tell people that this is what you stand for, and these are your limitations, I've seen my peers, my bosses, and my teams actually come and support and show up for that. I remember there was the vice chief of staff for our very senior person back in my previous company.

There was a very important critical meeting happening during my non-working hours. And I was willing to flex though I wasn't happy. And this person walks up to me and said, "Hey, man, actually, this is your non-working hours. You should not be going back on your principles. And we can actually move the meeting," which had like five VPs and a lot of kind of senior leaders, but we moved into that.

Once you go and seek help and tell people what your boundaries are, you'll be amazed at how much people are willing to support and help you and just kind of show up for you.

[14:29 Qin En] 

Absolutely. And I think that inspiration from the people who have supported you, I'm sure you're carrying that now to your team at Stripe.

Maybe talk to me about how you engineer that kind of boundaries or this kind of good practice among your current team at Stripe.

[14:44 Meenakshi] 

Few core principles there. Number one, we talk about work-life balance, but actually, we just have one human being. So the concept is actually work-life integration and I learned it from a very senior leader at Stripe.

So when you talk to people about number one is kind of understanding where your team is in their journey of that integration. Some people are at that stage where they want to kind of work crazy hours or they want to kind of, you know, really make it happen. There are others who are trying to balance different things and everybody has a unique way. So I think number one is seeking to understand, without making any assumptions about other people's lives, and just kind of being a good sounding board.

Number two, I would say is in an environment like ours, people can define what they want to do. And you'll be amazed like as a leader when I let them define their goals, they do a much better job or they stretch much more. Versus if I try to tell them what is our north star? So when you trust the team and you empower and lead, give them that much, they can do wonders.

And the third principle that I've lived almost all my career and very much so at Stripe is to lead with a kind of goal in mind rather than the inputs in mind. So I couldn't care like where they're working from, when are they working or how are they sort of kind of doing it, but if they've set some boundaries for themselves, I would absolutely respect that.

And on a side note, if I see any of my team members that I think like late emails or online, I do go back and say, "Hey, what are you doing? Is there something broken or, you know, it's your time to take off?" So I think just encouraging that also goes a long way.

[16:28 Qin En] 

Just creating an environment where people can come forward to talk about the boundaries they have, and also you keeping a close eye for them, potentially crossing those lines is super helpful. But I guess the one thing I was just kind of pushing this topic a little moment, actually, it's a big part about culture. It's about what you've rewarded and what you don't reward. It's a common stereotype. It's, you know, companies that just put the values on the wall, but then at the end of the day, it's also about how you reward because rewards drive behavior.

So I'm curious as to how you, as a leader, have thought about those rewards and also measured things like outputs and deliverables to make sure that there's a right balance between the team's work-life and also what needs to get accomplished.

[17:13 Meenakshi] 

I'd like to think that the award mechanism is in three parts, the number one is what impact are you driving?

Right. So every business has a set of KPIs or metrics and goals. And of course, as a team, you have to deliver to those targets, right? And as a part of that, the team understands that they have to deliver on those numbers and those targets. So that's kind of number one. The second one that's equally important to me is how are you delivering those?

So it's about behaviors. It's about, do you care about lifting others versus lifting yourself? Do you care about doing the right thing, even if that comes at the expense of certain metrics? Do you care, communicate, collaborate, or really kind of build that culture, where all of us are more than the individuals, and how, do you kind of bring that synergy?

So there, how is really, really important to me, there are times when we fail in experiments, but I would make it a note to give a shout out on how we tried, how we showed up, and how we supported each other when things were breaking down. But I think that's really important and it's important to embody.

The third component here is how were you feeling at the end of it? You could be driving great impact. You could be really showing up, but then maybe inside your suffering as a pattern or like something is really breaking down or you're not feeling great about kind of what. Like a lot of my check-ins also are around "how were you feeling?" Which goes beyond how you doing are, or what's sort of bothering you.

I think that brings out that connection and that compassion that helps people keep going forward. And the end of the day, if you take care of their feelings, their impact, and their behaviors, I think it makes a great combo for success.

[19:03 Qin En] 

Yeah. And I really liked the part about how you call out, not just the achievements that the team has made, but even when things don't go, according to plan. Being able to talk about it openly really normalizes it, and people feel a lot more comfortable to kind of share and discuss this.

So maybe shifting gears a little, Meenakshi, maybe tell me a bit more because I heard that you grew up in India. When did you make the move over to Singapore? And where were you in your family stage at that point where you did the transition? Because I'm curious about the culture and the cultural differences, so to speak.

[19:38 Meenakshi] 

It was an interesting shift. We moved here in 2018.

[19:43 Qin En] 

So relatively recent.

[19:45 Meenakshi] 

Relatively recently. Almost four years here now. It was an interesting switch on multiple counts. As I said earlier, we were trying to balance two careers and my husband was kind of really doing well at his company, Microsoft, and I was at Google.

I got an opportunity to kind of lead a regional role and it looked like a great move, but it also meant disrupting his kind of role and figuring out what he's going to do. It wasn't easy. We had long discussions about what it is going to be like. Are we going to do a long-distance? Are we going to try it out a little bit?

But then both of us as parents are so specific or particular that we were sure we're not going to live, do a long distance. And kids have either one parent or the other. So we wanted to make it work. Mainly moved initially. And we took the decision to move. We were told that when it could work remotely from Singapore, for India, but two months after the move, we figured out that that wasn't possible legally and heavy work, right?

Like one person sort of optimizing for their credit. And the other one asked actually writing down their resignation. In those moments, just kind of, again, going back to the basics of what matters as a family. How you support each other was a kind of our go-to principle. So we looked at our financials, and we were fine.

We were liking the place. We thought it was good learning. It's a good move. And then if he persisted, we will find like, you know, other opportunities or commensurate opportunities even in out. So for the first six months, I actually took a career break just to settle down with kids. So he was the one managing.

Who's finding the house, running everything, and even training our helper while I was kind of really managing that transition at work. And then, later on, he joined a company here in Singapore. And fast forward today, like three and a half years since he joined, I think his absolute love of what he does and so am I. So I think it's really about sometimes just being okay with plans not working as they were and sort of remaking them as we go along.

[21:51 Qin En] 

Wow. Thank you so much for sharing that story. That's truly inspiring sometimes. You know, when you look at leaders like yourself and your husband, it's easy to see. Oh, everything looks like it's smooth sailing and all, but I think being realistic about that, very much appreciate it.

Now I want to double click also on that transition for both your sons at that point, right? When they were relatively younger. Arguably it's easier for, let's say you to make the transition because you know, you had a job lined up and as adults, I think you could cope with that. Any challenges in kind of settling down now settle, even settling as a family and a new culture altogether.

[22:26 Meenakshi] 

Yes, it's always a package deal, but I'll go back a little bit. My younger one, when he was two years old, he was diagnosed with a kidney condition and we had to kind of go through a certain set of very rigorous treatments. He's doing is slowly fine now. And I feel blessed about that, but that was a very tough phase in our lives.

So before moving to Singapore, I actually had to turn down an opportunity to move to us for a very large global role. I had to decline a very meaningful opportunity, something that I always wanted to do in my career, but it required the location of Sydney. The doctors were not sure if the environmental change will really help him or would make the condition worse and it was not a chance worth taking.

So it came to a lot of that sacrifice. Once he turned five, when he was outgrowing that condition, we started evaluating our options all over again, and we moved. But he was still on a lot of medications. So when we moved here because of kind of constant years of steroids and other difficult medicines, he was emotionally very sensitive to a change of place.

When we were actually kind of wrapping up our house back in India, he wasn't there. Like we had kind of taken him out, sent him with a friend and he didn't know that we were moving. All of this while on the radio as we are going on a long vacation and we are going to have fun and eat ice cream every day.

And when we came here and we started living here. I know my partner since he was not working. And this is actually a blessing in disguise because he was not working. Every time we saw him going to the emotion, it was like, okay, let's go to Sentosa. Let's go-to kind of another theme park. This is vacation time.

And we just kind of ran it like a vacation for the first couple of months, just to settle him down to the started liking that place, that opposite question, that any sort of emotional issue could kind of impact them physiologically. So we were very, very sensitive. On the other hand, I think there is also a lot to learn from kids, right?

That they are much more resilient than adults are. So my elder one was constantly helping us. Sort of makes that story to the younger one, on how we are on a vacation, how he goes to school on a vacation because the younger one was not going to school and others, the elder one was great. So he would create that story like he's sort of playing a school role, but it's not actually a school.

So I think I learned kind of how-to, I got like really supported. And mostly, I would say the transition wasn't easy for me. That's not me. That assumption. I had so many friends in such a great network back in the day. Moving countries and moving jobs sometimes make you very lonely.

For six months honestly, if there was one person who wanted to run back, the first one was me. The second one was my younger one, and I think the two other boys were a lot more resilient and they definitely found us an anchor here.

[25:25 Qin En] 

Wow, thank you so much for sharing this. This is truly a moving story, and I'm so glad that you went through this successfully, but I'm sure no amount of words can describe the challenge that you must have felt because of the new country, new role, and all those challenges, but I'm so glad that you persevere to get as a family.And now that's a good outcome to that. 

So looking back at this entire experience, Meenakshi, what kind of advice would you give to parents out there who potentially might be considering such a big change in their lives? With families, you know, what are some of the lessons you have learned?

[26:00 Meenakshi] 

I would say two things. Number one, have the belief you can have as all. Have the desire and have the belief that it's all possible. Sometimes just having that mental energy and having the belief can do wonders for us. And number two, I would say is to seek help and set your own boundaries, on what you want to do and what you don't want to do. After all, everybody has a unique journey.

Sometimes we go into that mode of looking at others and thinking maybe they have a perfect life. The moment we start getting comfortable with our own imperfections and we start getting comfortable with sometimes imperfect work that we do or imperfect speech that we give or imperfect deliverables that we have, it starts to lose enough.

It starts to fall in place. Take it easy. Have the belief have the patience and the world is open for you.

[26:52 Qin En] 

That's such beautiful and on-point advice, I completely agree. Right? You believe that you can do it all, do your best. And of course, include your family in the process and work something out collaboratively. As you have very much exemplified.

Meenakshi, thank you so much for coming on today's show and really opening up and sharing. I think it's truly an inspirational story that you and your family have been true. If some of our audience would like to connect with you, how can they best do so?

[27:19 Meenakshi] 

I'll be privileged to connect with anybody who would like to I'm available on LinkedIn. They can reach out to me on that and I'll be happy to share and learn from them too.

[27:29 Qin En] 

Sure. Sounds good. Well, once again, thank you so much for taking time out to join us today. Meenakshi. Such a pleasure speaking with you.

[27:35 Meenakshi] 

Likewise, Quin. Thank you for having me. It's an honor to be here and thank you for being such a wonderful host.

[27:45 Qin En] 

Thanks for listening to the Parents in Tech Podcast with me, your host, Qin En. We hope you were inspired on how to raise kids and build companies. To catch up on earlier episodes or stay updated with upcoming ones head over to www.parents.fm to join our community of parents in tech. There, you can also drop me a question, idea, feedback, or suggestion. Once again, the website, it's www.parents.fm. That's all for this episode, folks.

See you next time.