"How to Find & Do Work That You Love - Morning Keynote" featuring Heidi Williams, Director of Engineering at Grammarly (Video & Transcript)

"It's okay to not have a five-year or ten-year plan - I have never been that kind of person. Following my curiosity, interests, finding the things I like and then crossing off the things I don't like as I go has served me well and has kept me interested in the moment." - Heidi Williams

Heidi is the Director of Engineering at Grammarly, where she leads Grammarly Business. In her 25+ year career, she's led several 1.0 initiatives with a focus on B2B and Platforms, including VP of Platform Engineering at Box, Founder of WEST, Co-Founder and CTO of tEQuitable, and various engineering teams at Adobe. Heidi is also a technical advisor for PaymentWorks and Raise For Good. 

Transcript has been edited for clarity.

Karen Ko: I'm so excited we're getting a chance to sit down with Heidi Williams, who is the Founder of the WEST program, as well as the Director of Engineering at Grammarly, where she leads Grammarly Business. In her 25+ year career, she's led several 1.0 initiatives with a focus on B2B and Platforms, including VP of Platform Engineering at Box, Founder of WEST, Co-Founder and CTO of tEQuitable, and various engineering teams at Adobe. Heidi is also a technical advisor for PaymentWorks and Raise For Good. Welcome Heidi! 

Heidi Williams: Thank you! So glad to be here, and I have to say - I love seeing so many familiar faces from every different aspect of my life in my career! Folks who live in my neighborhood, and our kids went to preschool together, folks I worked with at Adobe and Macromedia, and folks from different roles that I've had across my career. Welcome everybody! So glad to see you all. 

Karen Ko: I’m seeing some love for Grammarly in the chat too! I'm going to jump right into the questions now. Heidi, did you know you wanted to become the Head of Engineering of an organization of 35 people when you were little? What were your childhood aspirations and what did ten-year-old Heidi want to be when she grew up?

Heidi Williams: Great question. No, I don't think even 10 or 15 years into my career did I know that I wanted to lead engineering organizations. As a 10 year old, I had no idea that I wanted to do programming or computer science of any kind! I think when I was 10, I probably thought I would either be a teacher or a writer. I think I had interests in people, and learning what made people tick. I think in college, I toyed with maybe going into psychology or learning other languages, or something like that. I think it was it's probably anything BUT going into something in the Sciences actually.

Karen Ko: You mentioned on our prep call that teaching, psychology, and child development - these things all come into play when it comes to people management. To continue this thread on people management - what ways have you found to be effective when it comes to scaling yourself in this role?

Heidi Williams: Yea - I do feel like teaching and writing and psychology all come as part of my job now as an engineering leader because a lot of mentorship is involved in helping people learn and grow in their careers. 

As a people manager, writing and learning how to communicate effectively to get your ideas across is really important. Understanding what's important to someone - what motivates them, what are their career aspirations, and helping them achieve all of that. I do feel lucky that my 10-year-old self can say I got to do some of those things that I had in mind! 

As you grow as an engineering manager, become a manager of managers, and then a director or a VP, a lot of what you need to do to scale is to figure out not just how to delegate, but how to know which folks in your organization are ready for the next level of responsibility. Reflecting when you have time to help someone grow into a role vs. when there's such a gap in how much someone needs to learn. Perhaps you need to bring someone new into your organization that can operate at a more strategic level to give you bandwidth to do the next level of things that you need to do. I think it really does come down to delegating and then figuring out how to surround yourself with the best possible team whose skills complement each other and have different levels of maturity, strategic thinking, strengths or interests. It's one of the things I've tried to do to scale as an engineering leader.

Karen Ko: Absolutely. You can't do all the things yourself when you're trying to scale! The flip side of delegating is, as someone who's an employee of that potential manager who's looking to scale, is learning to ask for what you want. I would love to hear about your story of learning how to ask for what you want. Can you tell us more about that?

Heidi Williams: Yeah I think I actually learned that the hard way. This goes back to when I was pregnant with my first daughter, who is now 16. When I was at Adobe, I ended up interviewing at Google and I was pretty sure that I was going to take the job, and so told my manager and my manager's manager that I was quitting. They said "Wait, wait, you should have told us before that you weren't happy - let's figure out a plan. What is it that you actually want?" 

For the first time I felt like someone was REALLY asking me that question. I was like "okay I'm gonna go for it!" and laid out the different things that I thought were important to me and ended up getting many of them, which really ended up being a huge boost to my career.

A little bit of a backstory of why I learned this the hard way. The reason I was unhappy happened the year before I was on maternity leave. The first half of the year had been the best six months of my career - we shipped this amazing product under crazy time constraints. No one thought we could do it. We were building and rebuilding the whole thing from scratch. It was a really big team - maybe as many as 18 people working on it - and it was an amazing release. Super high quality, super super impactful. 

Then, I went on maternity leave two weeks later for six months, and when I came back, it was performance review time. My manager forgot that I had been there the first six months, and no raise was allocated or set aside for me- it had already been distributed to the team. I had hoped that I would be promoted to senior manager at the time, but because I had been gone for six months, I basically dropped out of people's minds. I was really upset about that - I thought if I worked that hard I should have been recognized for it, and so at the time I said yeah okay I understand, and I just kind of let it go. I didn't push for a raise, I didn't push for a promotion, and it just sat with me for six months and made me unhappy, just feeling that it had been unfair. That was when Google called and said do you want to come interview for this role, and so I thought "why not - maybe Google has an idea of what I can do and how I can be successful." Funny story - they were trying to figure out how to embed Flash in their search engine - going back for folks who remember Flash back in the day. Anyway I thought this is great, I'm gonna have this opportunity to do something new - I'm going to learn, I'm going to grow, they'll give me the title that I want, they'll pay me what I think I'm worth etc etc. Interestingly when I did go back and negotiate, and they asked what is it that you want, I realized what I actually wanted was that I was really curious to learn about the business side of Engineering Management, not just what is it that we're going to build or looking at Partnerships or different kinds of aspects of business, but how do you make these product decisions. So I said that out loud, and they said great we're going to get you a mentor on the business side. He was in corporate development, speaking a language I did not understand at the time, which was fascinating. They also sponsored me to go to a Stanford Executive Education and take two weeks to be onsite and get a mini MBA in two weeks. I did end up getting promoted and got a raise but it never felt as good as if I had just been recognized outright for it. Long story, but there was a moment where I realized it's so much better to ask for what you want early and not let it become a sore spot or feel like a consolation prize when someone's doing a diving save to keep you at the company. I think after that I was more proactive about my career and about asking for what I wanted before it was too late, just to let people know my expectations. Otherwise they'd have to read my mind if I didn't say it out loud! 

Karen Ko: Thank you so much for sharing that! When it comes to career planning and being able to ask for what you want, career planning is the number one thing our mentees want to work on through the West mentorship program. What advice might you have for mid-career women who are trying to find the work that they love?

Heidi Williams: I have never been someone that had a long-term plan that said "you know someday I want to run my own company or be ahead of engineering." I was always looking around and was curious about the things around me. What did the people I admired do or how did they operated, what insights did they have? I would try to learn about someone's role and what was involved. I think I used my curiosity and followed my passions, and that led to more and more responsibility. I started asking for things after I had done that mini MBA, I call it an Executive Education. I got an opportunity to work on a partnership with Salesforce! I was like this is cool why do companies partner and how do they do co-development? I followed that curiosity which later ended up benefiting me when I wanted to get into Partnerships and building platforms at Box. I would say it's okay to not have a plan - that's the big advice - it's okay to not have a five-year 10-year plan. I have never been that kind of person, and I feel like by following my curiosity and my interests and finding the things I like and then maybe crossing off the things I don't like as I go has really served me well and has kept interested in the moment and enjoying the journey, more than worrying about where I end up at the end of it. 

Karen Ko: I think I've also heard you talk about your opportunity to learn within your current role and how that's also kept you engaged. 

Heidi Williams: Yeah, I'm very motivated by learning, and I think I'm always happiest when there's something new that I'm learning and I think there's also something about taking risks. I can go into anything where I know half of it, and I don't know the other half. That's the perfect mix for me where I'm a little bit grounded where I don't feel like I'm completely floating in the air, I've got one foot on the ground, but the other half I can learn and grow and I have a support network around me to help me in case I fail or help me get back on track if I'm going in the wrong direction. I really like doing those kinds of things, taking calculated risks to go explore something new, and that's really energizing for me. 

Karen Ko: That actually plays really well into my next question about how you've been able to find courage in taking big risks in your career! For instance, you left Box to start WEST as a mentorship program, and you co-founded another organization called tEquitable with Lisa Gelobter and I would love to hear a little bit more about how you were able to find that confidence and courage to go for it. 

Heidi Williams: First of all I will say I feel incredibly fortunate and lucky to have been in financial situations where my family could last for a while on no paycheck or a limited paycheck, so just fully recognizing that's not the situation everyone is in, and I feel very grateful that we were able to do that. I set aside a timeline and said even for WEST, I said let me try this for a year, figure out if I can run a business, and know what that's like learning how to do sales - which was wildly uncomfortable when I started! I actually had a bunch of different life experiences that have helped me get good at sales and so learning how to build a business and putting a one-year clock on it and seeing how far we'll go. Doing some budgeting and see if we can make it a year, I think the same thing happened for tEquitable. It within that first year that I was starting WEST that I realized, oh actually I really miss building up a product, and so when the opportunity to work on tEquitable came around, I thought this is great I can use my engineering skills again! It was really within that first year window that I had carved out for myself and as I mentioned, having one foot on the ground and taking a risk on something else whether it's learning a business or figuring out the administrative pieces felt that I had learned through WEST, and bringing that to Equitable. At tEquitable I started coding again for the first time in 15 years, and I thought okay well I know how to problem solve. Maybe I don't know React yet, and I've always been afraid of JavaScript, but I'll figure it out. Google and Stack Overflow helped with all of that! I think that's part of it - not just figuring out what do I know, and what am I going to learn - but then also figuring out what's my support and learning path for that. Going back to coding - Google and Stack Overflow, who do I know in the industry that would be willing to Mentor me into coding again, and things like that. Figuring out my support network for this new risk that I was taking on was an important piece of it. I would say for anyone who's changing jobs, if you're going to take on something risky, ask your new manager, "how are you going to support me in this role and learning Journey?" It's a great way up front to see if they are also committed and accountable for helping you be successful with that.

Karen Ko: It sounds like you've also relied a lot on your network for resilience when it comes to continuing to learn or finding out about new opportunities. You've done so much in your 25 years of your career and there's so many more years to go, as an engineer, founder, mother and leader. What tactics have you learned along the way to help you stay resilient and sane?

Heidi Williams: Yeah there's one that really comes to mind which honestly was a huge mind shift for me when it happened. When I was at Box they offered a bunch of different courses and learning and development opportunities, and one of them was called the Energy Project. All good things come in quadrants so does the Energy Project! The whole concept was how to balance your energy. Knowing we have higher energy and low energy, positive and negative energy and thinking about what it looks like in low positive energy, where you are in a moment of renewal and refreshing. You're in this calm and peaceful place. When you're in high positive energy, you're firing on all cylinders. You're getting everything done, you're at the top of your game. When it starts to get frantic and chaotic, you get into high negative energy where you are freaking out and you're getting really stressed out. The thing that happens after that is low negative energy, which is burnout. From any of those quadrants, you always can come back to low positive energy to refresh and renew. There's also multiple kinds of energy - whether it's mental, emotional, spiritual, physical, and recognizing which of those needs to be refilled in this renewal piece. The big thing that resonated for me was that you cannot stay in high positive energy for long. If you are someone who supports other people or that people are relying on you in some way, you can't do that for a sustained period very long and you have to come back to low positive energy and renewal. That was the first time I realized I didn't have to put myself last. I didn't have to say "after work, my kids, my husband, and my friends, then I can finally go get some exercise or I can have a glass of wine with a friend or take a vacation by myself or with friends or something like that. It was the first time I realized I had to put myself first and refill my cup in order to get back to high positive energy and support everyone else around me. It just flipped the script completely. I think we know a lot of women have the tendency to put themselves last, but this was justification about exactly why I had to tell everyone around me to "sit back, I need a moment," or "I'm gonna go do a thing, I'll be back." It really helped me sustainably take care of myself so that I can continue to be my best for others that rely on me. 

Karen Ko: I love that, thanks for sharing! I feel very privileged to have you and my partner and to be able to ask you all the questions that I want to ask but this Summit is not about me, it's about all of the attendees that have joined us for today! I have one last question for you before we open up to the audience. For our last question, what is one main takeaway you'd like our attendees to remember? 

Heidi Williams: I was reflecting on the name of this Summit and that it's about leadership and I think two things that I would say is one, thank you all for taking time to invest in yourselves in your own careers! It is so important and the reason that it's important is that leadership really does show up in every possible way. You could be an individual contributor, you could be a people manager, you could be a herder of cats like a project manager or a program manager, or someone who works really cross-functionally. You are all our future role models and leaders for the next generation of women in Tech, and so I love that you are investing in your careers and helping yourselves become leaders so that we can continue to grow and increase diversity across the tech industry! Thank you all for being here and I hope you get some awesome takeaways this week and and can share back with your organizations.

Karen Ko: A big round of applause for Heidi for sharing all of her amazing experience and knowledge with us! Please welcome Inky to the stage - she will be running the Q&A portion of this talk! 

Inky Ajanaku: Hi, thank you Heidi! That was amazing - I was taking so many notes furiously! How did you broach the topic of getting promoted? 

Heidi Williams: There's actually a couple of times that I've had to broach that topic. Certainly my example at Adobe was not my most graceful, I didn't really want to use a moment of leaving as leverage, but at the end of it, I really did feel like I deserved it six months ago so why not ask for it.

The other time I advocated for myself to be promoted was when I was at Box. I love telling it because I feel like there are nuggets in here that everybody can use. I was a senior director of engineering, and had already been promoted pretty quickly from director to senior director. I thought I was ready for VP and I had some peers who thought I was ready for VP. However, when I went to talk to my boss and said I'd like to go up for VP, he said I don't think you're ready yet. I was said, "Wait this is news to me. What are you talking about, I thought I was ready and certainly my peers think that I am. I know I'm a different flavor of VP maybe than others, so what I did was a 360 review in person. I went and interviewed a bunch of my peers and said "Do you think I'm ready for VP what does VP of engineering mean to you. What do I do well? What do you think I should work on?" I collected all of that data and came to the conclusion that I actually was a different kind of VP than other heads of engineering. Maybe I wasn't the most deep technically, or the most operationally effective, but business orientation was something none of the other heads of engineering or leaders of engineering had, so I made the case that he needed me on his team because I brought something special, and I had a VP presence around the business side of things and strategy that was really important. So, using the voices of others who gave me feedback about whether I was ready helped me make a case successfully.

The other thing was there was another woman at the organization who wanted to go up for director, and she said I don't know I'm ready. I said I don't know if I'm ready! She's like, "wait a minute - we're doing that thing where we don't think we're ready but we are!" and so I said, "Alright I'll dare you to go for director, if you dare me to go to VP!" and so we both put our cases together, read each other's cases, gave feedback and then we both ended up getting promoted! It was a great case of holding each other accountable and not letting ourselves fall in the trap of thinking we're not ready just because one person said so. That's really poignant because I think a lot of people were talking about imposter syndrome in the chat, and if you feel like you can rely on other colleagues, you talk openly about that in order to get yourself out of that mental loop as long as you can build a trusted relationship with people.

There is a concern sometimes when you are self-deprecating. If you're sharing that with people that you don't fully trust, it can reflect badly on you so be careful not to fall into that trap. On the other hand, if you can find people that are trusted where you can just sort of be like oh crap I think I screwed something up, and I don't know how bad it is, what do you think. You can actually have that open dialogue and have others reflect back to you that maybe it's not as bad as you think, or they don't know that thing either, or nobody has done that and it's hard. It gives you a little boost of confidence that there are external factors that might be at play and it's okay to not know everything all the time. I definitely rely on my peers both at my company and outside of to give me a pep talk when I'm feeling hard on myself.

Inky Ajanaku: That makes a lot of sense. There's a couple of questions here while we're talking about networking and five-year plans. One of the questions asks, "how do you answer people who you are hiring or networking with who ask you about your five-year plans? What do you respond with?

Heidi Williams: It's so funny - I have a trick where I can't answer where I'll be in five years, but instead if you ask me "what at the end of your life what do you want to say you have done or what impact you've had?" For some reason that's easier for me to contemplate. I think the first time someone asked me that I was like, oh yeah before I'm done I want to write a book! I'm like wow saying that out loud I guess I have to write a book at some point. So I think I talk instead about what I want to learn or what I want to do or recognize that I want to have an impact or I want to leverage my strengths like being a business leader. When I first was looking for a job I would say I want to be somewhere where I have a seat at the table to make business decisions and not just product decisions. Those are usually the kinds of things I talk about - either about what I want to learn, where I want to grow, or what kind of impact I want to have, rather than a specific title. 

Inky Ajanaku: That's really helpful. Another question here was talking about how do you push initiatives through that you believe in? 

Heidi Williams: That's a good question - sheer force? I'm definitely someone who's a consensus builder. I think that's my natural style, connecting dots about things. I think there are definitely moments where I have to say no this really has to happen but yeah I like to test ideas. Identify if we are clear that there is a problem, do we have data around that, if we have an idea of how to fix it, can we measure it when it's done. Taking a little bit of an engineering orientation there to be clear about what problem we're trying to solve and then how we'll measure success is often helpful. The other thing I will share is a book I read when I was pretty early in career - called "How to Work with People You Can't Stand." The whole point of it was you can make amazing things happen if you can understand someone else's goal and help them achieve it and you can share your goal and they can help you achieve it. If you work together, you can actually undo a lot of bad behavior or objections from people who say no or stand in your way. It usually comes from some frustration they have in achieving their own goal, and so if I can somehow tie my goals to other people's goals and understand where they're trying to go and how we can help each other, ends up being really effective.

Inky Ajanaku: I think that touches on goals and everyone having the same goal. There's a question here about working in the area of business that isn't being prioritized or not getting as much attention. How do you approach that?

Heidi Williams: So the question here is what to do if I find myself in an area that's under invested? Great question. There's two approaches - one is to ask more questions. How does that area tie into company goals, what are the right levels of investment, what is the most impactful thing that you can do that ladders that area up to the company goals, etc. Or, you could advocate for getting rid of it. If you can say you know, if this thing I'm working on is not that important, then we're all wasting our time, all the whole team. Once you free yourself from being tied to that thing, I feel like opportunities open up, and you can figure out if you should further invest in or cut completely and reorient your team towards something more important for the company. 

Inky Ajanaku: That's a really great approach. Speaking of opportunities, how do you build a personal brand being a woman in Tech especially now, there are a lot of people looking for new opportunities. Do you have any thoughts on that?  

Heidi Williams: It's funny, I think I'm just a super authentic person like I can't help but be myself. There's certainly been times where I shouldn't be fully transparent because I'm the leader of this team and they don't want me to tell them all the things that's on my mind, but I think I've just embraced who I am and tried to lead with authenticity. Maybe one extra piece of advice is I discovered in college that I like public speaking, so that has been an easier way to develop a personal brand because I try to find opportunities to speak and the personal brand comes out around the stories that I tell as as speaker.

I guess it's harder if you don't want to do that, but you could become a writer and write blog posts. A good friend from Box found her voice through writing blogs and I think developed her personal brand in that way, and now she's doing some public speaking as well. I think there are ways to figure out what are your strongly held opinions, what things you believed in, what your strengths are, your superpowers, and then double down on crafting a story around that and then find opportunities to align and leverage your personal brand and interests with the projects and opportunities that you work on. 

Inky Ajanaku: You spoke a lot about being in environments where you've had resources to develop your knowledge but there's a question here about navigating an environment that's ambiguous where you're not really clear what success looks like. Can you talk a little bit more about what you reach for in those environments when you're not sure what the specific goal is? 

Heidi Williams: It's a good question. Hopefully there's someone who has assigned you this work that you can talk with and ask what success looks like, but maybe the first thing to do is a little exploration. See if you can define success together and figure out how to take something really big and turn it into concrete pieces. I think in ambiguous situations, it's not just learning what you need to do, but maybe crossing things off that you know you don't need to do. Figuring out how to scope it out and discuss what parts are non-goals so that we don't have to focus on it. Hopefully there's a few people in the area who you could interview and ask what success looks like, or what do you want to get out of this, or what do we think. Having a goal, even without a success metric is still enough to at least get started. Maybe the first goal is to create a little bit more clarity, more shape, around what it is you're trying to do. I don't know if that's helpful - that sounded very vague to me! 

Inky Ajanaku: It's very helpful! There's a question about diverse teams and how do you make that happen if you don't have a diverse team? 

Heidi Williams: I'm very proud of my team - it is very diverse on multiple dimensions and I really love that. It is interesting, this comes back to what role we all play as leaders and role models. I feel it is a little easier to hire women on my team because I can be a leader and a role model for folks and they really appreciate that. One thing we have as a benefit is to offer mentorship or partnerships, or start building community so I definitely do that I participate in a lot of communities and I recommend that for anyone who's trying to diversify their team and really get involved. Not just for recruiting, but to be there to participate and to give back. I think that's really important, whether it's through WEST or there's a great online community called Elpha which I really appreciate. I have found that's a great way to connect with people, and have people at our company try to participate in different kinds of events, conferences, and community.

On top of that, setting yourself recruiting goals to say let's sort of make sure that my outreach is to a diverse set of candidates and that it's ethnically and racially diverse, and all sorts of underrepresented groups. The more people in your outreach, the more likely you will have some folks that come onsite and interview and pass the interview and come to your company. Partnering closely with recruiting to make sure that we're looking at diversity across the pipeline. 

Inky Ajanaku: I think that was all of our questions this has been great, thank you Heidi!