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“CTO’s Lessons Learned on the Journey from Software Developer to IPO”: Cathy Polinsky with Stitch Fix (Video + Transcript)

July 30, 2018
VIDEO

At Girl Geek X Elevate 2018, Stitch Fix CTO Cathy Polinsky shared stories about learning to code in Logo, how a male boss helped her ask for she needed to succeed as a new mom — and how to manage up.


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Angie Chang: Hi! Welcome to Girl Geek X Elevate, our first virtual event for the Girl Geek Dinner community. My name is Angie Chang, CEO and founder of Girl Geek X, and this is Sukrutha Bhadouria. We wanted to say “thank you” for joining us this Wednesday morning for our Girl Geek X Elevate. We have been hosting Girl Geek dinners here in the Bay Area for over 10 years — we’ve hosted over 170 dinners at 100 companies, over 100 companies — and we are excited to be able to expand and have world domination. When we thought about 10 years of Girl Geek Dinners, we wanted to rebrand and say…

is for the community, our community of 15,000 women. It is not just dinners — it’s events and podcasts and webinars and different formats that can help us reach more women globally. Our community of women has grown over the last 10 years, and we’ve heard lots of feedback from women that want to tune in to last night’s dinner by podcast, on their drive to work, or whether they want to tune in from where they are, which is not necessarily where we are in San Francisco. We’ve also taken this chance — and this opportunity to partner with mission-aligned companies, and today we’re grateful to have the support of fantastic mission-aligned sponsored like Mozilla, The U.S. Digital Service, PayPal, SalesForce, Intel AI, Clever, Quantcast, and interviewing.io.

Gretchen DeKnikker: Is that me now, Ms. Angie?

Angie Chang: Yes.

Gretchen DeKnikker: Okay, hi everybody. I’m Gretchen DeKnikker, COO here. To build on what Angie was saying about how we are looking to change things going forward, and expand. We’re very excited, that we’ve worked very, very hard to have our speakers from a wide range of backgrounds today. 70% are women of color, and 40% are black and Latina. And we had a very special focus on that. We wanted to make sure that we’re bringing underrepresented voices to the table. The whole thing was to create opportunity for women to gain visibility and recognition and to share with the community. I think at this particular time in history, it’s really important as we get a seat at the table as women that we pull up another chair and that we be very mindful of the limitations that are greater than just being a woman, and the challenges. So just being more supportive there.

We do want to have more voices at our table. We’d like to invite in ideas on bringing more women of color into the fold, your guys’s ideas on how do we partner and bring more male allies in. These are all things we’re gonna be focusing on now that we’re on the other side of this event. Part of wanting to do this particular event was, like Angie said, to reach more people. But also to … Another thing that we’ve heard is mid- to senior-level career women aren’t necessarily represented strongly at the events, which is understandable. People have other things to do in the evenings.

We wanted to create this opportunity because as you grow in your career, the theme today is growing from a manager to a leader. So what happens when you become a manager of managers. In every stage of your career, the job is different. We have some great sessions today to help everybody on that journey.

We’ve got one on self-awareness and ego with Minji Wong. We have one on the art of the interview, especially around the candidates interviewing you with Aline Lerner from interviewing.io. We’ll talk about delegation and empowerment and advocacy with Arquay coming up just after Cathy. And planning and goals and finding those metrics that matter. How do you lead by metrics when you’re not doing the work yourself, and you’re not in there every single day. And I think we’ll get into that a little bit at the engineering panel at the end of the day. So, Sukrutha.

Sukrutha Bhadouria: Yeah, hi. I’m actually so excited because I’m seeing people dial in from everywhere all over the world, how cool. I saw people dialed in from San Francisco, Florida, and I also saw someone comment on our shared earbuds. For me, why we’ve been wanting to do this, especially have technical women give talks, not just about leadership, but about … because there’s more important things to talk about. Then we have talks about security, team learning, and just keeping yourself up to date in terms of your technical skills.

Why is this important is because you and I got into women on stage talking about what it’s like to be in technology beyond just what it’s like to be a women in tech.

So we have speakers from Facebook, from LinkedIn, from Salesforce who are going to be providing their insights, their experiences. And hopefully you all have, not just lessons learned, but you also leave with inspiration today to keep at it, going forward with it. So with that, I’m super excited to introduce Cathy, whose our first speaker, so who’s going to be speaking next.

Cathy Polinsky: Good morning, everyone.

Sukrutha Bhadouria: So really quickly I wanted to introduce Cathy. Cathy is the CTO of Stitch Fix, which is awesome. Cathy and I first met when Cathy was working at Salesforce as an SVP. She’s going to talk about her journey. What I really definitely want to call out is right now she leads the engineering team at Stitch Fix, and supports the company’s efforts to deliver services that meet the clients’ needs. Cathy has been working in great companies like Yahoo!, and Amazon, and of course Salesforce where we met. So Cathy, go ahead. I’d love to hear what you have to say.

Cathy Polinsky: Fantastic, thanks. And thanks for this opportunity. I just really appreciate having an opportunity to network and talk with other women. I just got back from a board effect meeting two weeks ago where we were talking about needing more women representation on boards, and more women representation in the industry. As many of you all know, we’ve come really far, we’re seeing a lot more women in the industry. But as the numbers come back, they can be kind of depressing that even though the number of women in software, in technology organizations has grown, the percentages haven’t changed that dramatically over the last decade.

I hope we can work together to build a more inclusive community and support system. I wanted to share my story of how I got to be from a kid who grew up in Pittsburgh, work my way through to be a software developer, and now to a CTO at Stitch Fix.

It’s hard not to be able to see everyone here. I’m not sure how many of you know of Stitch Fix. I’m hoping that there’s a lot of clients out there, but I’m sure there’s many of you who have maybe heard of Stitch Fix, but don’t quite know what we do. So let me just start a little bit with that so you can get a sense of what I do on a day to day basis.

Stitch Fix is really disrupting how people can find clothes and items they love, and look and feel their best every single day. So as many of you probably have shifted your buying behaviors to online, I’m the same way. I hate going shopping. Before I even learned about Stitch Fix, almost all of my purchasing was done online. I never really go to the store, and yet when I’ve tried to buy clothes online, it’s a really broken experience. There’s so much that goes in your head when you walk into a store. What items you think that look good for you and match your style preferences. And there’s so many things that go in your head when you walk into a dressing room to figure out whether something looks good on you, your complexion, your body type. There’s a lot that goes into thinking about your wallet and your price preferences for whether you’ll take that item and spend that money to go to check out.

When you go online and try to buy something, you get a flat image, you may get a review, but you won’t really know if that person is like you, if they have the same style preferences that you may have, or the same body type. So Stitch Fix really disrupting that business. You fill out a detailed style profile. It’s kind of like a dating profile. Everything that goes in your mind for what you do when you’re walking into a store, and what things generally work for you, and what things don’t. And then you get paired up with a personal stylist who takes that information, paired with tons and tons of algorithms and data science with detailed recommendations that are tailored exactly for you to pick items that will work for you. You get a box delivered to your door, you don’t know what’s gonna show up in that box. You open it, try it on at home. Hopefully find things that you love. But easily return things back that you don’t. You only pay for what you keep.

This was just so disruptive when I really got behind the scenes to learn about this business model and what it was doing and how we’re impacting clients lives that I was really excited to join this group, and now I’m the CTO. My role expands across engineering, IT, product management, and security. So it’s a pretty expansive role, and every day I get to do something different, and I’m learning new things as well.

I just feel very fortunate to have this job and to work with such amazing women here at the company. But I wanted to talk to you about my path to get here. It hasn’t always been easy, but I’ve had a lot of support along the way. I wanted to talk to you about things that I’ve learned along that path, and support systems that I have really benefited from that we can also help others along the way, as well. So I mentioned I grew up in Pittsburgh, Pennsylvania. I was in elementary school in the early 80s, and no one had computers at home. Personal computers were just spinning up and the Apple 2s were starting to make an entrance into elementary schools. What’s amazing is that Apple really wanted to nurture that community. They were giving grants out to schools, and donating computers to elementary schools. I heard they even had a surplus of Apple 2s when they launched the Macintosh and say they were really thinking about how they could use that for good. And I was one of the beneficiaries of that. My school took advantage of those programs and created a computer lab, and my teachers loved it. Every week we had a computer lab time where we got to go to the lab and learn computer programming.

My first language was Logo, which was a little tiny triangle on a screen, kind of like the predated Scratch, and you can draw little pictures. You can draw boxes and houses and make simple commands. But it was a real programming language. You could do loops and you can do procedures. It really started that spark for me of what technology could be. I carried that forward for quite some time, even though, after elementary school there were no real programs for me. Our middle school and our high school really didn’t have many computer classes. In high school, I was told about a program at Carnegie Mellon, which was near where I lived in Pittsburgh for a summer program for computer science. And I applied and got accepted into the program, and it was amazing. The morning was taught by a computer science professor at CMU. It was about algorithms and data structures. And the afternoon was special projects where I go to see an arm and try to program an arm robot to make knots and do some object orient programming to make and solve mazes.

After that summer, I really thought that this was something I was interested in and I’d want to pursue. And I had a lot of encouragement in a way through the professor that I got to meet at CMU who talked to me about colleges and talked to me about studying computer science going forward. That spark that I had through both teachers and professors really carried me a long way to thinking about this field because frankly a lot of people of my generation, a lot of women in my generation are only here because of having that spark from someone else, generally a family member. There’s generally someone, a dad, an uncle, even a mom who was a scientist, or someone in that field, but I didn’t have that. But the teachers and the professors that I did engage with really were my spark to enter in the field.

Fast forward, I went to a small liberal arts school in Philadelphia, Swarthmore College and studied computer science. Had a lot of support there for programs around women in technology. And then when I graduated in ’99, it was the peak of the dot com boom, and off I went to Seattle to work at Amazon.com. It was quite an amazing ride, and just every month we were launching new stores. The growth was pretty crazy. The company growth was amazing as well.

It was not easy as I was one of the few women, certainly on my first team, I was the only woman. But I did find my little support group. I had friends that I got to meet, people who helped me through that way as I was trying to figure out a team that worked for me, and I’m forever grateful for that.

I was also there during the rocky bubble burst of the dot com industry, and I had thought that I had missed the interesting times at Amazon, and I wanted to leave and go see what it was like to work at an early stage start up. So I left Amazon, came down to the Bay Area, worked for a small start up, saw it go up and down, and realized it’s not fun to work on software that doesn’t get used. And I swung to much bigger companies since. I went to Oracle right after, which was probably a little bit of an overcompensation. But it was there that I really was starting to do team leading and thinking about being an engineering manager.

A piece of … I have a fun story about that, of I just happened to be meeting with an old friend, and was telling him that I was interested in being an engineering manager, and that I was thinking that I might transition to doing that within the next couple of quarters, it wasn’t gonna happen immediately, but I didn’t think anything of it. And then three weeks alter he calls me up and says, “Hey, there’s a position open for an engineering manager at Yahoo! that I think you’d be a great fit for, you should apply.”

And that just really surprised me. I never thought that another company would consider me for an engineering manager since I had never been an engineer manager. And it never would’ve happened if I hadn’t shared that story and spark with the friend of mine.

Advice that I give a lot of people is to be really free in sharing what your passions and interests are. You never know what opportunities are out there, and people will see you in a different light when you share those aspirations. So figure out things you want to try. Figure out things that you might want to do, and then tell people. It might be a different technology that you want to try, or a new project that hasn’t even been spun up for your company, but your manager or your colleagues may look at you in a different light when those opportunities come out and think of you as a perfect person for that fit.

Fast forward, I went to Yahoo!. It was the most trafficked site on the internet when I was there, ahead of Google. It was a pretty vibrant time when I first arrived. It kind of got rocky. I had my first baby there, and it was … I was working on a really tough project as we were revamping our ad network and really trying to figure out what was coming next for the business. I’d say one of my lowest points of my career happened there where I came back full force after maternity leave, I was excited to be back, I was excited to work on new projects. I even raised my hand to work on this brand new project that was revamping this architecture. Several months after that, I was realizing things just weren’t working. I was really unhappy. I was not feeling like I was being a good employee, not feeling like I was being a good mom. I’ve always felt like I was just chasing to get home in time to relieve the baby sitter, and my baby had stopped eating… I was breast feeding and pumping at work. Even though I had a good enough supply, she was gradually drinking less and less milk every single day. So I felt like this just isn’t working, I need to figure something else out because I don’t feel like I’m doing either job well, from being a great engineering leader, or a great mom. And so I quit — I went in, I went to my boss and I said I was gonna be quitting, and I made up some story about doing some other project.

To my surprise, they all tried to convince me not to leave.

So my boss really asked me a lot of questions. I hadn’t really felt like I was doing that good of a job, so it was really surprising to me at first that they would make all of these overtures to keep me to stay. Other peers and leaders also came to talk to me. And then finally the VP of the business came to talk to me. It was someone I hadn’t engaged with that often. He asked a lot of insightful questions, and I was really trying not to go into details or trying to make it into a way that they would convince me to stay. But he got to a point, and he said, “Cathy, I don’t feel like you’re asking for what you want, or what you need” and that really struck me.

And then he paused and he said, “I don’t know if I can give you what you want or you need, but you’re not even giving me the chance. So if you can think about what it would take to for you to be happy and successful, let us know and give us a chance to make that right.” And that was just such a powerful moment for me. And I was like, “Wow.”

It was the same advice someone had given me before about sharing things that I need and want for transitioning into being an engineering manager. But it was that same advice in a very different context for me when I was going through a difficult time in my job. So I really took a step back and said, “I’m trying to do too many things. I’m trying to be this amazing engineering leader and get the next promotion. I’m also trying to figure things out with my baby. I’m trying to travel to the different sites for these leaders. And I just need to figure out sequencing and not try to do too much at once.”

So I pared things back, I said I’m not gonna do these travel trips for the next 3 months. I also flew my mom out and she helped me with my baby while I looked for a new childcare provider. I got through those next three months, and I decided to stay. What happened after that is I got into this groove, things were doing much better for my baby, things were much easier for my job. I figured out how to do both of them a different way than I was doing it in the past. It really helped, potentially even saved me to stay in the industry at a time that was pretty difficult. It was really thanks to that VP Sandeep who had that conversation with me and made me look at things a different way.

Fast forward, I then went … Yahoo! had a lot of difficult times. I was looking for what’s next, and I had my eyes set on Salesforce. I came into Salesforce and I got to work on a lot of different really great initiatives, but I also got to see a different company that was really focused on giving back. It made me think about that time at Apple, how they influenced specific education and schools and students studying computers where Marc Benioff, the CEO over at Salesforce really wanted to think about how he could give back by not just being a company that makes a lot of money, but also is really successful in helping the community at large. So he created a 1–1–1 model, 1% of time, 1% of equity, 1% of the products were given to non-profits.

I think this is something we can all think about how we can use the power of the institutions that we work for to make a different in our broader community, helping to support other girls, helping women in technology, persons of color, helping with diversity and equality is something I feel like I been it for and I would like to roll forward to others.

I learned a lot working there, and I also feel like I had a lot of advantages working for a company who really cared about equality. So Marc had a program when I was there. He had a quarterly leadership meeting, it was called ECOM at the time. He would bring in his leaders and go business by business and go through the financials of the company. At one point he looked around the room and said, “Where are all the women?” And there may have been a chuckle or two. But after that he said, “No, we need to fix this. I want 30% of the room for all of my meetings to have women in them.”

It didn’t mean that the people who normally would’ve been invited didn’t get to come, it meant that another seat was pulled up to the table. I really liked what Gretchen was saying about just pulling up another chair is really what gives people different opportunities and advantages. I got that opportunity at Salesforce. I was invited to some meetings with really high level leaders at the company, and I got to listen in and engage and learn how the company was operating at that level, and that really helped prepare me for this role as a CTO. And I think that’s something that we can all think about is how can we pull up another seat to the table to give people an opportunity to see what’s going on in your meetings, to see what’s going on in your company, and to have broader access in this industry.

So fastfoward, I’m now at Stitch Fix. It is an amazing job, it’s great to be in this role. It’s something that I’ve always aspired to do and to be. But what I never aspired, and had hoped to work for as a company, that has such high gender diversity. Stitch Fix is 84% women, which is just amazing. Every day I walk into rooms that I’m completely surrounded by such amazing women. That’s something that was so difficult than any other company that I had ever worked. I had been used to being one of the only women in the room where I’ve gone and done the count and said, “Wow, what percentage of women are here today,” and I’ve stopped doing that. After being in a room with 60% women and 70% and 45% women, you don’t really need to do the count anymore. And what I found what’s amazing when you have that level of gender diversity is you really can be your authentic self. I remember early on in my career just wanting to fit in and be one of the guys. I wore T-shirts and jeans and wanted to kind of be appreciated for my technology, and not stand out as different than anyone else.

And now I get to wear dresses every day, I get to be myself, I don’t have to think about how I’m phrasing things or to couch my thought process or argument in a different way to fit in with the culture of the company. I feel like when you have a broader diversity group, everybody can just be themselves and focus on the business, focus on the clients, focus on how to make a difference. And that’s what’s exciting to me.

I love working at big scale companies, I love working at growing teams, growing technology, growing architecture, shipping software, and that’s what I get to do every day here. We’re in this amazing growth phase at Stitch Fix where we’re launching new business lines, where we’re growing our business. And it’s the technology that you see on the website, but it’s also everything that goes underneath it to power it from tools to run our warehouse to tools for our styling organization. Tools also for merchandise, of how we pick and buy and plan and allocate the right inventory for our business. I love wearing T-shirts and jeans sometimes too, and I love wearing dresses, and I love that I can choose. My aspiration going forth in this industry is that we can all be our authentic selves at work, that we can be recognized for what we do.

I hope that I’m seen as a great CTO, as a great technology leader, and not just a female CTO. And that my aspiration is that there are many more of you who rise to these levels as well, and that we can form a great community and support network. I think that that’s essentially my story that I wanted to share today. I think Sukrutha, we may have wanted to open things up for some questions? If anyone has any questions, and you want to type them in, feel free. Oh, there you are, hello.

Sukrutha Bhadouria: Hi, I was looking at everybody’s comments. A lot of people were talking about how they’re loving your story and the honesty with which you’re sharing it. I see a question asking about who your current inspiration is.

Cathy Polinsky: I have to say my biggest inspiration right now is my CEO Katrina Lake. Katrina was a young CEO founder who came up with this idea while she was in business school. She was fascinated by eCommerce disruptions and the sense that the apparel industry was one of the few industries that had not reached double digit online sales, even six or seven years ago. And the sense of the reason is because the model was broken and she had an idea for a different way and a different model. It has not been easy for her. As a young female CEO going to Sand Hill to raise money was not a cake walk. So she really focused on how she could get to profitability as fast as possible so she wasn’t dependent on that industry. And the thing about her is she is just such an authentic leader — she is so smart and savvy, but does not put on airs and is really someone that I’ve watched her, as she’s had her first baby, and navigated the world of pumping and nursing and things that I hid behind. I remember one of my stories of pumping while I’m eating, and having a one on one and someone saying, “What’s that noise in the background?” I’m like, “What noise? I don’t hear any noise,” and not really being that authentic about what was going on and what I needed, really just trying to hide what was going on. And that’s something I don’t think she even thought twice about hiding anything about. She’s not trying to be a role model as much as just authentically is navigating that aspect of being a mom and being an amazing CEO.

Sukrutha Bhadouria: That’s awesome. Someone also pointed out about the fact that there was a podcast where Katrina shared her story. But I do see a lot of questions speaking to your story about Marc Benioff noticing not enough gender diversity and then trying to make a difference. How does one who is not in that level of influence… How would somebody else who would get impacted by a change like that… How would they bring about the influence when they’re not in the seat of power? What advice would you have for people like that?

Cathy Polinsky: I think we could all try to help at whatever level that we’re in — really raising this as an issue to your boss, or thinking about ideas about how you could help, whether it’s the community, or a local university that’s near you. Maybe it’s letting people shadow you in your job and bringing a seat to the table. And then it’s also the opposite of asking — asking, “Can I come to this meeting?” I think that people … It may not always work out for you, but it will never work out if you don’t ask. So really being able to assert yourself and to see if another seat could be brought to that table.

Sukrutha Bhadouria: That’s awesome. And next question, and I am seeing a lot of people asking similar questions, so I’m just summarizing the next question. It seems like a lot of people want to know how do you identify when is the right time to jump at an opportunity, or navigate towards a specific opportunity to grow in your career?

Cathy Polinsky: I’d say the thing I’ve always done is try to look at what are the big opportunities out there that no one is going after, and being open to them. I was going to talk a little bit about managing up. The aspect that has worked for me both as a manager, but also as a strong number two to other of my leaders is to really open myself up to understanding what are the big challenges that my boss is having at any given time, and see how I can make a difference —

What are the big chargers, what are the big opportunities that we’re going after. What are the gaps that we see and how can I lean in to make myself available when there’s challenges. I feel like that’s always helped me, whether it’s a brand new initiative that got spun up, or someone’s leaving the company, someone’s moving to a new role and there’s a gap in the organization. Really saying, “Hey, how can I help? Is there something that I could be doing here? I’d love to take a shot at helping on these projects.”

The way that I’ve always been able to do that is to build a great team. I love to delegate and hire the best people that I can and load them up as much as possible in the same way. And that gives me the space and the capacity to take on more when I am in a growing opportunity that needs more help.

Sukrutha Bhadouria: One quick comment I do want to add is that people are asking for all of your questions to be posted in the ask a question list. So just in case you’ve been posting them in the chat but not in the ask a question list, if you put it there people can vote. Next is actually one of my favorite questions. There are nine and counting votes for people who want to hear more about the differences in responsibilities and duties of being a software developer, an individual contributor, versus a CTO. How did you transition between those roles, what is the main differentiator do you think? Or the biggest challenges.

Cathy Polinsky: Let’s just talk about software developer versus manager because it is this really interesting thing that the things that help you be most successful as an engineer are not necessarily the things that you need to do once you’re an engineering manager. And that’s something that we’re not sure … We talk about that a lot at my staff meeting of if that’s true for a lot of other fields. I get the impression that that dynamic is not always as clear as it is in software development. When you’re focusing a lot on how you’re working on coding and projects and building up your technology skills, those things are great and important to lean on so you understand the projects are going on track, but there’s a whole other aspect of how you’re managing people and projects and initiatives that you don’t necessarily always get to do as an individual contributor.

It was a very challenging and different experience for me, but one that I really loved. I feel like as a software developer, you get these CS highs — You solve some problem, you are excited about getting to a solution that works, and that you can push out and deploy, and that’s just exciting that you get to see that solution, you get to see people using it, and you get to see the difference that you’re making.

When you’re a manager, and you’re not actually writing the hands-on code and influencing through people, things take longer. You can’t always see the, “Hey, I’m trying to give people advice and coaching them in this way. Am I getting through to them? Is this working? Am I shifting the team to be better or not?” It’s not that you can see that on a day to day basis, but that your impact is much broader, and if you can stick through it and realize it’s not the same as that every day, every hour, continuous feedback loop that you find other ways to see your impact, and that you can be really proud of the people and lives that you can influence.

That’s what I really love about the job is that I can have a broader influence and every day is different, as I mentioned. I’m working on a lot of different types of projects, a lot of different types of focus. And I think that’s the thing that also changes as you take on more and more teams, as you go from being a manager to a manager of managers, or a CTO. I was saying as I was making that shift, things when you’re a software developer can go quite fast. You can have a great day, and then you can have a bad day. Depending on the big challenge or bug or issue that you’re dealing with, things are a little slower as an engineering manager. You see the challenges and you’re working towards fixing them, or you’re seeing things working really well, and they stay pretty well for quite some time.

But when you have a larger scope of influence with teams that suddenly don’t have much commonality between them, you can go from one meeting and think, “Wow, things are finally coming together for this group and I can see the light at the end of the tunnel and things are going great.” And then you go into a whole different meeting and you go, “Oh, now I have this other problem that I have been neglecting that I really need to help nurture.” It’s just a different pacing, and just being open to those shifts are really important — and to finding different people to get advice from because this job changed quite dramatically.

Sukrutha Bhadouria: Yeah, totally. I can’t totally relate because I’m going through that as well myself. Thank you so much Cathy, I wanted to thank you from the bottom of our heart to get started with what’s our first ever virtual conference. Your talk was so inspiring, we see it through the comments, and we feel it too. All of the questions that came in, thank you for asking those questions.

Cathy Polinsky: Thank you for organizing this and thank you for inviting me. It’s great to be here.

Sukrutha Bhadouria: Thank you. Over to Gretchen [for our next session] …

Cathy Polinsky is the CTO of Stitch Fix. Prior to Stitch Fix, she was SVP Engineering at Salesforce.