Driving alignment and urgency within teams, work-life balance, and the changing PM landscape | Nikita Miller (The Knot, Trello)

Nikita Miller (00:00):
And many of the companies that I've either worked with or advised, coached over the past few years, it was all about outcomes. Everyone was, "Outcomes, outcomes, outcomes," which is right. You want to make sure you're doing the right thing with the right goal, and that's fine. And some folks, myself included at certain points, swung way too far on the outcomes train and forgot that output is an indicator of that. So if you have a team that's doing all of the ideation and figuring out how to make decisions quickly and getting the right documentation and setting up the right product briefs and design briefs and experiment briefs, all the things that we know go into to successful product development, that's great, but if you're also not shipping a lot of things to market quickly enough, then it just doesn't matter that much.

Lenny (00:52):
Welcome to Lenny's Podcast, where I interview world-class product leaders and growth experts to learn from their hard one experiences building and growing today's most successful products. Today my guest is Nikita Miller. A huge thank you to Camille Ricketts for recommending Nikita and for connecting us. Nikita is senior vice president and head of product at The Knot Worldwide. Before that, she was VP of product at Dooly, and before that she was head of growth and retention at Trello for over five years. In our conversation, we dig into how product managers and people getting married are similar, a bunch of advice on getting into product management, a really cool framework for how to align roles and responsibilities within your cross-functional teams, a bunch of advice for working effectively as a remote and distributed team, and the one question that Nikita asks constantly to get the most out of her teams. Nikita is amazing and I am excited for you to learn from her. With that, I bring you Nikita Miller after a short word from our sponsors.

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(03:21):
Thousands of people apply to join this collective, and I personally review and accept just about 10% of them. You won't find a better place to hire product managers and growth leaders. Join almost 100 other companies who are actively hiring through this collective. And if you're looking around for a new opportunity, actively or passively, join the collective. It's free, you can be anonymous and you can even hide yourself from specific companies. You can also leave anytime and you'll only hear from companies that you want to hear from. Check out lennysjobs.com/talent. Nikita, welcome to the podcast.

Nikita Miller (03:59):
Hey, Lenny. Thank you. I'm excited to be here.

Lenny (04:02):
I'm excited to have you. So I don't know if you know this, but I'm actually having a kid in a couple months and I've been doing a lot of reading, as you do when you're going to be a parent. And I was reading a lot of stuff on The Bump, which turns out I realized was something that it was in your umbrella of products.

Nikita Miller (04:15):
It a part of The Knot Worldwide. Yeah.

Lenny (04:17):
And then I realized y'all have that for pregnancy, you have a site to help you with proposals, you have a site for obviously wedding planning and vendors and just party planning in general. And so is the general strategy to be there for every adulting milestone in life? Is that the plan?

Nikita Miller (04:34):
Yes. That's a nice way of putting it. We talk about it as being there for the big celebrations in life. We have these celebratory moments that mark adulthood, and so to be part of that journey, we primarily focus in the wedding space but yes, across the whole journey.

Lenny (04:52):
It feels like the two pieces you're missing are divorce and funerals. Is that the plan or do you want to stick to happy things?

Nikita Miller (05:00):
I think we're sticking to celebrations. I think we're leaning on the world needs a lot more celebration right now, so helping folks do that.

Lenny (05:07):
You're here. Okay, cool. It's a really smart strategy. It makes a lot of sense, once you get someone with their wedding and then they expand from there.

Nikita Miller (05:15):
And their friends too.

Lenny (05:18):
Interesting, right, because they register on The Knot and they'll know what's going on there.

Nikita Miller (05:22):
That's right. You register.

Lenny (05:24):
Genius. So we're going to talk about some of the things you've learned along your time there, but I wanted to start with your previous gig at Atlassian and specifically leading growth and retention at Trello. Many people listening to this podcast either use Trello and love Trello or are thinking about using Trello, and so I thought it'd be interesting to hear just who do you find Trello is the most ideal for? When is it good and smart to go with Trello versus Jira or Linear or Asana or something like that?

Nikita Miller (05:53):
A few things. So I think Trello initially started out as being the task management or planning tool for anyone as opposed to the others you just mentioned, which tend to be in software in our industry, and that's who we're geared towards. Trello when it first started was very much on being simplicity of design, being easy to use, tactile, easy to onboard. You don't need customization, you can use it in single-player mode or multi-player mode. And so that meant that at the beginning, we got a lot of people using the product that were small businesses, that were families, that were people planning their weddings potentially. 

(06:32):
And then over time, as our users became more sophisticated or had more problems to solve, that's how I think we evolved and grew with them. So some of it's around this concept of progressive disclosure where you start with a small problem and as it gets more sophisticated, Trello grows with you, whereas I think some of the other products, they start with complexity and if you want something simpler, you kind of have to pull things away or tease things apart. And that was definitely something that helps Trello stand out. I think now, many years later, you'll find that Trello is very fully featured and fully powered and they now lean into that a lot more, but that wasn't always the case.

Lenny (07:14):
So it sounds like Trello broadly was meant for a lot more than just software teams building product?

Nikita Miller (07:18):
Yes. It started off I think being inspired by software teams and wanting to understand how to move and manage tasks easily. That was the origin story, but then very quickly became the kind of tool that anyone could use to manage anything. And now I think we're back more the product is way more towards the software development and that's a lot more of the competitive advantage, but I think the people that are excited about Trello and the ones that made Trello really impactful weren't necessarily software.

Lenny (07:50):
Got it. When you think back to your time helping grow and retain folks on Trello, is there a big win or something you're really proud of that you think back to that was a huge success in that time to help Trello grow more or be more successful?

Nikita Miller (08:07):
That's probably not what you'd guess. So when I started Trello, I actually joined to build out Trello's enterprise business. And so a lot of our growth and retention was actually about how to get more teams into the product and then spreading it throughout the org, so not only software teams but sales teams or marketing teams. And so the big push there was around collaboration. How do you create a shared perspective for everyone working on a project, not just a software team?

(08:38):
So we had a good time thinking through what's the customer experience, but obviously in the context of enterprise, which for Trello at the time was really tricky because it's such a customer first product, I think shifting our mindset to understand enterprise and teams specifically as a cohort was very different. And I think we've done a pretty good job of that or the team did a good job of that, and I think being a part now of the Atlassian suite definitely leaned into that even more.

Lenny (09:09):
Was there a specific feature that unlocked a lot of opportunity or is it just broadly, there's a bunch of little things you have to add?

Nikita Miller (09:15):
I think it was broadly a bunch of little things. So all the enterprise features that you can imagine that all products need to operate at the enterprise level, smaller features around labels like how do you color them? How do you name them, when do they appear? When you invite people, do you invite individuals or do you invite teams? So a lot of the work was around going from single player or two, three player mode to 5, 10, 20 people.

Lenny (09:41):
Got it. Coming back to the question of Trello versus Jira, because I think this might be interesting to people. Just if you're trying to decide should we use Trello or should we use Jira, what's a simple way to think about which way to go as a founder maybe or as a product team?

Nikita Miller (09:55):
I think that smaller teams, especially folks that are ideating, when you haven't landed on what you're going to build yet, I think Trello's a great product for that. For pulling ideas, for prioritizing them, for tracking how we're progressing through discovery, I think Trello's really great for that. For things that have been decided and are ready to go and are really in the breakdown these tasks and assign it to people, then something like Jira is probably a better use case, but I'm sure there people that'll disagree with that.

Lenny (10:29):
Cool. Building for PMs is what you were doing while you were working in Trello. I imagine that's kind of a bittersweet experience. I imagine in some sense they're an amazing market to sell to, on the other they're probably really annoying. What's a surprise maybe or a lesson about working on building products for product managers?

Nikita Miller (10:46):
I think you're right, it is a bitter sweet place to be. I think I less thought of it as building for product managers and just thought about it in the context of productivity overall. And productivity software in itself is really what's bittersweet because there are a lot of trade-offs and when you're dealing with a software team, for instance, how you measure productivity or define it for a PM or a designer or engineer and a data scientist is probably really different. And so the impossibility of solving for all of those use cases I think is always what's challenging, and we know that no one product is actually going to solve all of those use cases, no matter what the marketing taglines are out there.

(11:29):
And so it was really challenging to figure out what are the core things that a product manager might need to see or a designer or a developer, and how do you make sure that that core is there? So you get the 80% and then you spend time on the 20% that you know a very small segment of users are going to use, but they're probably your core, so maybe you spend some time there. But the answer is no one's going to be happy, and with Trello in particular it was challenging because for a while we built a product that was easy to use for everyone, and so then trying to really narrow in on well, what is a software development use case and what do we really need for that? And that might be very different from what a mom-and-pop shop is going to need or someone planning their wedding is going to need.

Lenny (12:15):
That's a good segue to something else I wanted to ask about. You used to build for product managers and now you build for people getting married. I'm curious what is similar about those two groups and what's maybe most different?

Nikita Miller (12:26):
A lot of similarity. So folks planning their weddings, think of it as an emotional, high stakes thing that you're hopefully going to do once, and so the pressure is really there. The pressure and expectations are really high, not unlike product managers or other folks in software, and ultimately wedding planning is this huge project where you have a bunch of stakeholders, friends, family. You need to manage multiple vendors, and the time horizon for a wedding once you're engaged is anywhere from 12 to 18 months, so it is a longtime project. I think there's a lot of similarities there. 

(13:06):
Some of the things that are a little bit different in terms of how we're building the product is the amount of decisions probably that need that go into wedding planning are far more than you'd imagine. So one of the reasons being at the Knot is so interesting is we go all the way from planning tools, so actively, how do you help people find inspiration and plan their wedding day-to-day to two-sided marketplace. We have our e-commerce business that's supposed to be registry and paper and obviously our affiliate businesses and the ads businesses, so it's a little bit different from a SaaS productivity tool, the business that we're in, but a lot of the problems that we're solving for users are actually really simpler.

Lenny (13:48):
Which one's more, I don't know, stress inducing.

Nikita Miller (13:51):
That's a great question. I think that couples, it's such an emotional thing for people, for individuals and their families and their friends, so I personally feel like I empathize with that in a way that I don't do the same for product even though I'm a product manager, because there are many projects and there're always things that we need to manage and that's just part of the gig. Whereas planning your wedding, for couples this is for many the most meaningful time of their lives, and everyone does this differently. So we have folks that are planning their multi-hundred person weddings and then there are 10, 15 closest friends weddings, but the emotional side of it is the same and you don't want to let them down because most aren't going to do it again.

Lenny (14:38):
Yeah, okay. That's what I would've guessed. It feels like wedding couples are more stressed. I just had an idea. I imagine you think about this. We're doing a baby shower right now and it feels like you're missing a opportunity to do the baby shower invite platform.

Nikita Miller (14:51):
Yes, we've thought about it.

Lenny (14:54):
And also registry, a registry platform.

Nikita Miller (14:56):
Yes, also that.

Lenny (14:59):
Okay, okay. So many opportunities.

Nikita Miller (15:00):
All the life moments.

Lenny (15:01):
Oh my God. One last question about Trello. Do you have any just tips for someone using Trello and may not be aware of something they could do with  Trello?

Nikita Miller (15:09):
I think the biggest that people probably know about but are often underutilized are Power-Ups, which is basically our integrations. And Power-ups are folks that are usually doing things that are more complex, often. But Trello, when you think about it with other products like Asana, as you mentioned, Linear, some of what people are worried about is that it's just not powerful enough, and Power-Ups are a way to do that. And there are dozens and hundreds of integrations that you can use it for. So that's worth checking out.

Lenny (15:39):
Awesome. Great tip. Shifting a little bit and zooming out, you've worked at a lot of different companies at a lot of different levels, also a lot of different geographies and I want to chat about that last piece. But maybe just broadly, what are a few of your biggest lessons about building successful and impactful teams?

Nikita Miller (15:59):
This is kind of my jam.

Lenny (16:01):
Excellent.

Nikita Miller (16:02):
It's kind of what I spend a lot of time thinking about, and I think every company go into you approach it slightly differently. For me, it usually starts with individuals identifying very clearly early on roles and responsibilities, like what are the expectations of a role? So in software, for most of us one of the things that I think I've seen done well or contributed to and multiple companies is the triad, product, design, engineering, data. And what does it look like for these roles and data science that's like other?

Lenny (16:38):
I see you put data in there.

Nikita Miller (16:42):
I'm trying pull that in. That is my mission. I love that. My mission is product, design, engineering, data.

Lenny (16:47):
It's not a triad anymore though, but I love it.

Nikita Miller (16:50):
I know. It's a quartet something.

Lenny (16:50):
It's just a chair.

Nikita Miller (16:53):
It's a chair. Great. So I think about that a lot. What are the roles? What do you expect for each of them and how do you define the responsibilities that we have to each other? I know it sounds maybe on the softer side, but I think a lot of what we can solve for in creating strong teams is exactly that. The exercise that I often do is I generally have an idea of what I think the roles and responsibilities are and the expectations across these four roles, but the exercise especially with leaders in an org is to have them sit down and write them for each other.

(17:29):
So Atlassian has some of this that they do in the form of playbooks, but it's basically I as a product leader, I'm going to write down what I think the expectations and the role and responsibilities of my engineering manager, of my designer, of my data. And then we look at it together and then we arrive at essentially a contract with one another about what we think that looks like and what that responsibility is to our teams, and from there, we cascade it throughout the org. This is very time-intensive, as you can imagine, and often leads to a lot of debate because depending on the kind of orgs or people's backgrounds, our expectations might differ, but I think that contract early on is really important.

Lenny (18:08):
This is super interesting and I want to go two levels deeper. Is there a template that you have? Is there specific questions you're answering? Is it freeform? How do you actually know what to write in one of these?

Nikita Miller (18:21):
There is a template. There are templates we can probably share after this-

Lenny (18:24):
Awesome. Great.

Nikita Miller (18:25):
... to run the roles and responsibilities, and it usually comes in a couple of forms. It's what the expectations as an IC? What's the expectation as a manager or with your team? And then what is it to each other and what are the things that are shared? So when we're running an experiment, a product manager's likely to write a product brief and go into the details of what that means. The data scientist is likely to help write the actual experiment brief, but we're all putting inputs into it. But then when it comes to data and analysis, my expectation is that both of you are doing that together.

Lenny (19:01):
And is the idea the PM writes, "Here's what I'm planning to do," is it the data scientist writes on behalf of the pm, "Here's what I expect you to do?" Who's taking the charge in each of these?

Nikita Miller (19:11):
You write your own. So I as a product manager, I write what I think my role is and also what I think what my expectations of my counterparts are and they do the same, and then we review it together.

Lenny (19:23):
And you encourage every team within your domain to do this amongst themselves. 

Nikita Miller (19:28):
Yes. 

Lenny (19:29):
That is very cool. If there's an example you could share that we could put in the show notes or a template, that would be great.

Nikita Miller (19:35):
Yeah. We'll do that.

Lenny (19:36):
What have you found as impact that comes from doing this a before and after? What kind of difference do you see having done this on team?

Nikita Miller (19:45):
So I'd say recently, I'd say in the past maybe five years, one of the things that has shifted and has caught some people by surprise, I don't know if it should or not, is around project management. So I think 10, 12 years ago, everyone expected that they would have Scrum Masters, and Scrum Masters have largely in many companies just disappeared. But then you think well, where did that responsibility go, because someone has to do project management? And this is different from program management internal to a team. 

(20:18):
And from my perspective, a lot of that now sits with engineering managers, which is a little bit different from how it was when I started in product where actually, a lot of that was put on PMs. And some of you might recall, it caused a lot of issues with product managers because they were the ones that were constantly like, "What's happening in the sprints? What didn't make it? Why didn't it?" Doing a lot of that work. And I think PMs are still responsible to keep track of that, but engineering managers are increasingly expected to be the ones that are actively making sure that sprint goals, for instance, are met. And that's a shift that I've seen recently that we do have to debate often.

Lenny (20:57):
I think one of the most interesting elements of this approach is that the product manager role is so I ill-defined and so different in every company, and so I imagine much of the benefit here is just what the hell is the PM's responsibility?

Nikita Miller (20:57):
100%.

Lenny (21:10):
Is there anything that you find is surprising about what teams end up taking off the PM's plate or putting on the plate that maybe other companies don't?

Nikita Miller (21:18):
I think a lot of people end up putting a lot on the PM's plate because of that misunderstanding. And so you end up looking at something as a group and saying, "Well, no one human can do all of those things all the time, so let's talk about what the shared responsibility looks like." And what I think is really powerful about the triad is that it's a recognition of there are shared responsibilities. Who's responsible for making sure that everyone understands what we're doing and why, the PM leads that, but evangelizing that is something that would be expected of designers and engineering managers and data scientists as well.

Lenny (21:57):
On the data scientist piece, you talked about how you're trying to embed that more and more into product teams. At Airbnb, data scientists were embedded in every team, so I totally get that.

Nikita Miller (22:05):
It's not everywhere.

Lenny (22:07):
Yeah, exactly. What more can you share there of just why you found that to be important and how you're approaching that?

Nikita Miller (22:13):
From my experience as a product manager, it was always a blocker. Getting your hands on the data, maybe having someone to troubleshoot with if as a PM you couldn't kind of understand or figure it out yourself, it was just always a blocker. And so then you'd also then have to go and negotiate with other teams about getting someone's resources to look at this problem, so that's one. The other is just that data scientists, as with most humans, we get better the more focused we are and the more in depth we are in understanding the product itself. So if you have someone that's dedicated to a zone or an area of the product, then it's much easier for them to spot patterns as opposed to attempting to understand what's happening every time a ticket comes in.

Lenny (22:58):
And so the shift you push for is instead of a centralized data team that you convince to give you resources, you embed the data scientist into the team.

Nikita Miller (22:58):
Right.

Lenny (23:07):
And do you call them data scientists, do you call them analysts? How do you think about that?

Nikita Miller (23:11):
That also varies per company. That depends on the organization and the work. Some teams require data scientists, not all. Some require analysts, so that just depends on what the team's working on, what's needed.

Lenny (23:27):
Got it. Coming back to the roles and responsibilities framework, do you encourage teams to revisit that every once in a while or is it like this team's done this thing and we're good for a while?

Nikita Miller (23:36):
I encourage them to revisit it and it's usually because something's fallen off the rails. I think if they were really great at it, I'd say every three months or every six months, let's have a look and see how this is going. But often it happens because there's some conflict or tension or something was missed and someone thought it was theirs or not and we have to do a quick retro.

Lenny (23:59):
What do you find is often that thing that is maybe missed or often causes tension?

Nikita Miller (24:04):
Execution. It's usually around execution and velocity.

Lenny (24:10):
Not moving fast enough?

Nikita Miller (24:11):
Not moving fast enough.

Lenny (24:13):
What do you find often is a way to help with that as a leader of teams?

Nikita Miller (24:18):
Well, one, just identifying what the velocity issue is. It can vary, so for PMs it's often around the velocity of decision-making. How long does it take us actually from saying we need to do a thing to defining it potentially, and then deciding are we actually going to do it or how? And that I think takes a long time for most companies, most people. So velocity of decision-making, so I think that tends to fall on the PM most often. The actual execution of it, the development tends to fall on both PM and engineering. So in engineering I find that depending on the org, some folks understand breaking up tickets into small pieces and why that's valuable and how to do it, and that's something that I think everyone in industry probably needs a refresher on, why that's valuable and how it works. And some of that is also shared by the PM because if you haven't articulated clearly or well enough what we're trying to do, then it is hard to break that apart. So those are the two things that are on my mind a lot.

Lenny (25:27):
Is there anything else along the lines of what you've learned about building successful teams? I really love this roles and responsibilities approach.

Nikita Miller (25:35):
Outcomes and output also comes up a lot, and many of the companies that I've either worked with or advised, coached over the past few years, it was all about outcomes. Everyone was, "Outcomes, outcomes, outcomes," which is right. You want to make sure you're doing the right thing with the right goal and that's fine. And some folks, myself included at certain points, swung way too far on the outcomes train and forgot that output is an indicator of that. 

(26:10):
So if you have a team that's doing all of the ideation and figuring out how to make decisions quickly and getting the right documentation and setting up the right product briefs and design briefs and experiment briefs, all the things that we know go into to successful product development, that's great, but if you're also not shipping a lot of things to market quickly enough, then it just doesn't matter that much. So that conversation is one that I think we often have to revisit on all the teams I've ever been on that yes, outcomes are important, but also the indicator is around execution and velocity. So if that's not in line, then a lot of the other things don't matter that much.

Lenny (26:50):
And so when you say outcome, you're saying here's the goal they're achieving or the impact they're having, or is it just the idea we know what our outcome will be but they're not actually shipping anything? When you say output and outcome, what are you referring to specifically?

Nikita Miller (27:04):
The outcomes are understanding what the goals are and what we might do to get there. So OKRs is one way to talk about that. Great. But embedded in that is and how are we going to get there? And the fact is, the more tries you have at it, the likelier you are to get it right. So we're not actively monitoring how fast does it take us to ship things to market.

Lenny (27:28):
I see. So if I can rephrase it, a lot of teams know and talk about what they should be doing. They have a strategy, they have a goal, but what you're finding is that there's just not a lot of action a lot of times and there's a huge opportunity just to get a team to actually ship more often and move faster.

Nikita Miller (27:46):
Yeah. There's not a lot of understanding of our role and urgency. It's urgent, and software in particular. You probably can't forget that because someone else is likely doing something similar or better and faster.

Lenny (28:02):
Makes me think of I think Frank Slootman is his name, the Snowflake CEO. He wrote this book called Amp It Up, where he talks about how to build thriving software companies and businesses in general. One of his three most important recommendations is always have urgency, to never let off the gas of urgency. That things always need to feel urgent.

Nikita Miller (28:22):
I'll check that out. But I think product managers, I consider product to be the ones that really need to drive urgency.

Lenny (28:33):
Say more about that. What have you found helps in creating that sense of urgency and continuing to increase output?

Nikita Miller (28:39):
Mostly reminding people often. And I don't think that's a question of, "Well, show me list of everything you ship. That's never going to work." Well, that doesn't make people feel good about the work that they're doing, but let's talk about our experimentation backlog. What do we have in there? How quickly are we getting those things out? Those are the kind of conversations that I think help. I think that having a good pulse on competition helps as just a friendly reminder that there are others out there doing this and thinking about things very similarly, possibly, to how we're thinking about it, so how do we differentiate ourselves? And a lot of that is about how quickly are we getting many ideas to market? Small tangent. The competition side is interesting to me because I've worked at a few companies where I've worked with founders who are like, "We don't have competition, we're the only ones doing this," and then fast forward a few years and you're like, "Here are all the companies that were your competition that you didn't recognize then that are shipping great product now."

Lenny (29:52):
This might be a tough question, but I think there's always a sense of we can move faster. It's rare that no, we're moving fast as we can. Do you have any kind of heuristic or I don't know, gut feeling of knowing and sensing where this team's doing fine versus this team isn't moving as fast as they can?

Nikita Miller (30:09):
How much time do we spend on what I'd consider optimizations versus bigger bets, and how long does does it take for that to happen? Right? Because you know you've talked to the folks or been in the companies where you talk about something that by most measures is pretty simple. Someone goes heads down for a week or two and gets it done and you talk about it and then two quarters later, someone mentions it again and you're like, "Oh, okay. So what are all the things we did in between that time to now why that seemingly simple thing didn't get done?" And I think that's hard to say as a product manager because everything we do is all about prioritization, and I'm sure there are a bunch of other things that were prioritized, but they're these little things that come up periodically, or bug fixes. Something is broken. How long does it take us to recognize it and actually fix it?

Lenny (31:03):
Do you have a heuristic, speaking of big bets versus optimizations, of just how much time/resources to put into each bucket?

Nikita Miller (31:11):
Unfortunately, the answer is it depends. If you're working on a business that is 30 years old and has many acquisitions, it is very different from a startup or a growth stage company.I think it just varies.

Lenny (31:27):
Yep. That's often what I find. One last question along these lines that was on my mind as you were chatting. When you're finding that a team is not delivering as much output as you would think, what have you found works in helping them recognize that and not get defensive and not have all these excuses for why it's happening, just help them see what you see?

Nikita Miller (31:46):
I'll tell you what I do. I don't know, I think folks might get defensive sometime.

Lenny (31:52):
Yeah, I think.

Nikita Miller (31:53):
But I'll tell you what I try. For me the biggest thing is just if folks are working on a sprint, it's very simply, "What did you deliver this sprint?" That's it.

Lenny (32:04):
Just asking questions.

Nikita Miller (32:05):
Just ask a bunch of questions. "What did you deliver?" And more questions, "Okay, fine, but what did you deliver to production? Great. And how long have you been working on that? How long? What was the cycle time?" So these questions that are really just I think seeking to understand because I understand complexity and so that exists everywhere, but maybe helping folks see that as they're reviewing their own work or their team's work goes a long way.

Lenny (32:35):
And it comes back to your approach of just focus on the output, not what they're planning to do, what they've actually done. This episode is brought to you by Ahrefs. You probably know Ahrefs as one of the leading all-in-one SEO tools used by companies like Facebook, Uber, Shopify, LinkedIn, Pinterest, and thousands more, but Ahrefs is not just for big companies. With their new Ahrefs Webmaster Tools, you can optimize your personal website like a professional for free. You can scan your website for over 100 common SEO issues that might be hurting your performance and search engines plus get advice on how to fix those errors. 

(33:09):
You can have it automatically browse your website's internal and external links and get actionable insights from your backlink profiles, and you can learn what keywords your website ranks for and see how you stack up against your competitors. Visit ahrefs.com/awt and start improving your website's visibility. That's ahrefs.com/awt. Shifting a little bit, you've been a PM for a long time, since 2010 I believe, and a lot of people move out of pm and so it's really cool to talk to someone that's been in the field for a while. What have you seen in terms of how product maybe has changed? The role of product management, the role of product leadership, and also maybe other functions like designer engineering?

Nikita Miller (33:51):
I think the biggest change for product at macro is how mainstream it is. I still find fascinating getting degrees in product management and going to business school to transition into product management and the whole discipline. And there's a whole business, honestly, around the business of product management, which I find really fascinating and it didn't exist. And I think for better or worse, that comes with a lot of good and in some ways might have removed some of the quirkiness and creativity that probably is required of product, but that's probably a different podcast. So that's one, just macro. In terms of the roles, I think that what we were talking before about roles and responsibilities and defining those for product managers, I think product managers are increasingly I think a bit more technical or expected to be. I think there was a moment where they were technical and then it was, "No, no, we're all generalists," and now I think we're going back to PMs need to be more technical.

(34:54):
I think designers, the expectation is that they'll be more business-oriented, design as a means, honestly, to an end. I think that's trending and probably for the better. I think the best designers I've ever worked with are also exceptionally savvy business people. And I think engineers are increasingly becoming what more product-focused, more user-focused. So product engineers is something Trello I think did really well. This idea that great ideas can come from anywhere in the org at any function I think is really magical. So as you're seeing PM's becoming more technical, I think designers becoming more business-oriented, engineers are becoming a lot more product/user-focused, to me that's amazing because it means that we're getting closer to what I'd consider really deep collaboration. And it's not to say that we're not experts. There are expertise within that that we expect of folks, but that care for other disciplines I think is where a lot of magic happens.

Lenny (35:57):
That's really interesting. When you say PMs  getting more technical, when you're hiring, interviewing, what are you looking for? Do PMs need to learn to code? How technical do you find they need to be?

Nikita Miller (36:08):
I don't think so, necessarily. I think a lot more PMs are. A lot more PMs are taking boot camps or coding classes, which I think is all to the good. I don't know that it's a requirement, but there is more of that and I think is very helpful. Similarly, a lot more PMs are taking more classes or digging more into data analysis, also really valuable. I don't think it's a requirement. I am not a technical PM, I don't have a tech background. I think I've been doing it long enough at this point to do okay, but I think it's a benefit.

Lenny (36:42):
You said that the PM is becoming more of just a thing with training classes and courses like that? 

Nikita Miller (36:47):
Yeah.

Lenny (36:48):
I did a search once on LinkedIn for how many product managers there are. Guess many PMs there are in the world, that have the title PM in their LinkedIn profile?

Nikita Miller (36:57):
A lot. I'm guessing a lot.

Lenny (36:59):
2 million.

Nikita Miller (37:01):
That's wild. 

Lenny (37:02):
That's wild. And there's 800,000 just in the US.

Nikita Miller (37:05):
Wow. 

Lenny (37:06):
That's a large group that I didn't expect.

Nikita Miller (37:10):
Back in my EdTech days, a friend of mine, her kids were in school and she came in one day, her son was in grade school at the time, in elementary school and he had this match to what careers, what you see, and they had a person at a computer, this image, and it was product manager. There was an option for product manager. And that's when I knew, I was like, "Okay, this is mainstream. We're about to become consultants."

Lenny (37:37):
I always used to joke, no one grows up and is like, "I want to be a product manager when I grow up," but I think that's starting to-

Nikita Miller (37:41):
It's a starting. It's a thing.

Lenny (37:45):
While we're on that topic, I imagine people often ask you for advice on how to get into product management. Do you have any advice there for folks that are listening that maybe want to get into that?

Nikita Miller (37:54):
There are many ways now. I think there are a lot of the typical programs that a lot of the big tech companies have, I think is one way. I think getting into startups as a product manager is a pretty awesome way to get into product because it's just a lot of problem-solving. The problem with that is you don't have anyone to teach you the right way, but the product will teach you the right and wrong way if you're with a team that is moving quickly. I still think working on smaller products and companies is a way great way to get into product management in part because you'll get to touch all of the functions that are required parts of the product discipline, and I think it's hard to get that experience otherwise.

Lenny (38:40):
The PM role, we haven't talked about this, it's just very hard and very stressful and mostly sucks in many ways. 

Nikita Miller (38:48):
Yes.

Lenny (38:48):
And we could talk about that if you want, but it was more of a segue to work-life balance, which I know you have some strong opinions about. So I don't know, you could take it either direction, but just thoughts on work-life balance/how hard the PM role is.

Nikita Miller (39:01):
The PM role is really hard. I feel especially now that I'm managing a lot of teams and PMs at a lot of different levels, I do find that periodically I remind them with the core of my being that, "I know this is hard." It is hard. There are a lot of expectations. You're expected to be competent across many areas all the time, you're expected to have an answer and you're expected to keep your calm and not lose your shit, and that's really hard. It just is. It's stressful. So I think I spend quite a bit of time with my team, my PMs, helping them understand that I understand that. And so when we're problem-solving, let's probably not solve for everything. Let's focus on one of many things that are expected. It's really hard. On work-life balance, as I mentioned to you I think about this a lot, I'm currently a mom and as you can imagine, that's a lot to manage at any given time.

(40:05):
And so recently, when I think about work-life balance, I don't use the word balance, I use optimization. It's this question of what are you optimizing for right now? Whether it's today or this court or this year, with the understanding that I don't think you can have it all at the same time all the time. And so I'm increasingly coming to peace with that. Where that's been interesting over the course of my career, I was chatting with my husband about this yesterday and was thinking about, early in my career I remember when we had big releases, folks would just work nonstop for a couple of weeks. We would stay in the office late, we would come in early. If it was international, we just probably wouldn't sleep because we wanted to make sure we QA'd everything before we released it, and that was an expected part of the product development life cycle.

(40:55):
And that was a lot of my early product years and I just did it and it was very exciting and I quite enjoyed it, but even then, the flip side of it for me was I also was a runner back then, so if I was training for a half marathon or a marathon, then the next week I'd probably do my long run in the morning and not start work until 10:00 AM. That was my version of balance. And I think many of us are lucky enough, especially in tech, that a lot of companies get that form of flexibility. So now fast forward 13 years, it is very similar. I don't do all of the drop-offs and pickups for the kids, but there are some weeks where I'm like, "This is the week I'm going to do all of the drop-offs and pickups," or, "This is the day," and that's felt much healthier for me than this expectation that I'm somehow going to balance it all and everything is going to be equally great or cared for all the time.

Lenny (41:56):
I think what I'm hearing essentially, which I really like and agree with, is sometimes you're just going to have to go sprint and go hard and work really hard and go long hours and then that doesn't need to last forever. And then when it's not, enjoy that extra time and build and recharge and do the things you got to do.

Nikita Miller (42:18):
Yeah. That's about right.

Lenny (42:18):
I find the same thing. I find that just working hard is very correlated with success, and a lot of times that's just a lot of long hours and sometimes you can't balance it for periods of time.

Nikita Miller (42:30):
Right. And it can also be at different points in your life, right? So right now at this particular moment in my life, I'm probably not going to go hard at a super early stage startup because I believe that you probably need to be in person and working really hard together for long periods of time. And not everyone feel this way, I know that. I've had these conversations with lots of friends and colleagues. So personally for me, that's probably not the decision I would make at this moment in my life.

Lenny (43:02):
I get that. Another area I wanted to touch on is remote work and distributed work. I believe most of your career, you were remote or you worked with remote teams and distributed teams and that's such a on-trend thing now where a lot of teams are working hybrid, working remotely, working with distributed teams. What have you learned about being successful working with distributed and remote teams?

Nikita Miller (43:23):
Yes. My entire career has been with remote or distributed teams. That's right. When I started early my career, I lived abroad for a while. I lived in Shanghai. I had a core team there, but also worked for the distributed team in Europe and Latin America, which meant all kinds of crazy hours and lots of sprints like we just talked about. Things that worked well, one, documentation. It's a thing. Asynchronous communication, everyone just has to get used to it and better at it, so increasingly just being better communicators, whether it's on a video or written.

(44:00):
I think that's just really important, and everyone building up that muscle is really important. For all of the roles I've been in, this notion of what does it mean to have really meaningful and valuable in-person time that can sustain you for the remote and distributed time is a really important. I think a lot of what's happened now in COVID and even now, a lot of teams have never met their coworkers. They don't onboard in person, they don't have events or offsites as frequently. And I think flexibility is really great, but I think that really, that makes it really hard, and to me, what I've figured out I think is that it especially makes it hard to solve hard problems.

(44:43):
Solving a hard problem remotely with folks that you haven't spent in-person time with, that you haven't broken bread with, that you haven't disagreed with in person and built that trust is just really hard. In fact, it's much harder. So some of the things I've done even here at The Knot Worldwide is periodically when there's a really gnarly problem, I wave the flag and I say, "Hey everyone, why don't we try and get together for two days and hash some of this stuff out, and then we can go back to our remote lives?" And I think folks have been maybe unsurprisingly very open to that because I think they see not only the efficiency but the camaraderie that can happen there as opposed to what was happening potentially on a Hangouts or a Zoom call.

Lenny (45:28):
What does that event look like? Where do you do it? What's roughly an agenda?

Nikita Miller (45:32):
One, the agenda is pretty tight before we get there. Myself or someone else are responsible for making sure that that's a well-articulated agenda that we all kind of agree on before we even get there, so I think that's one. I think 48 hours, two nights, and that's important to me because it tends to still just be hours in a conference room or a meeting room during the day, but you do need to build in the, "And let's go have dinner since we're all in person anyway, or let's have an extended lunch and maybe an extended day." I think that's just really important. And even early in my career when I was working more internationally, the company I worked for was pretty amazing because two or three times a year, the entire company globally came together for a week or two and it made a huge difference, and many of the folks that I worked with there are still friends and mentors.

Lenny (46:29):
Are you able to share what was the challenge you're trying to overcome in one of these times? 

Nikita Miller (46:34):
I can speak about it generally, which was just we had a change in strategy and we needed to land a couple of core decisions about what we might build. And there were lots of documents and lots of conversations, and back to the velocity of decision-making, remotely that can be really hard because with time zones, someone sends a doc, you comment on it, you get to the other day by the end of the week. And so days and days have passed and we still haven't landed it, and people have really strong opinions obviously that's something that big, so it's like, "Nope. Okay, great. Wave the flag." And not everyone could make it. Most people could, and the folks who could not were, yes, on a screen.

Lenny (47:15):
Was there anything specific in that offsite that helped you get to a resolution?

Nikita Miller (47:21):
In that particular one, it was one, very cross-functional and the unlock there was giving the data person the space to educate all of us. That was it. It was like, "You have the floor, educate."

Lenny (47:40):
I find that's often the solution is people just don't have all the same information that they're basing their decision on, so make sure everyone starts with the same foundation. Awesome. And that comes back to your push to get data integrated into every team and make that part of the four quad triad.

Nikita Miller (47:57):
That chair. It's the chair.

Lenny (47:59):
Anything else around remote work or distributed work that you found to be incredibly impactful or important?

Nikita Miller (48:04):
Well, the flexibility of it that I'm sure you've talked about with others, that is really important. I do think that Trello and Atlassian did this really well, is having standards around a couple things. The biggest one I think was overlapping work hours. So everyone had general flexibility, but there were some set of hours where everyone needed to be online at the same time for the most part every day, and that made a big difference. Onboarding happened in person. I think that in-person onboarding for new folks is really important for everyone. For any new person to an organization, I think how we work culturally, having a contact that you can reach out to, all of that I think is really crucial. I'm definitely of the so much of my early learning was in person and I have no idea how we're going to replicate that in a non-office setting. It's just really hard.

Lenny (49:04):
How long do you try to have that person in the office for onboarding? Is it a week? Is it a few days?

Nikita Miller (49:09):
A week.

Lenny (49:09):
Awesome. Shifting a little bit, just a few more questions. You mentioned you worked in China, you also worked in the UK for a while, obviously in the US now. What have you found to be some of the biggest differences in maybe the product culture or just culture in general working in these different areas?

Nikita Miller (49:26):
The confusion around what product management is is universal. That's not specific to US I think, and the fact that it's changing, that I think was the same. I don't know that I've found that many differences in terms of how we approached goal-setting, all very similar. The need for urgency, all those principles I think this are the same no matter where you are. Part of what I experienced when I started in Shanghai was the feeling that the product manager was expected to have all the answers, which as you can imagine was really overwhelming. And so I remember because I was young and I didn't know that much about product management, and I definitely did not have all the answers, I spent a lot of time helping the team help me get answers and that was a little bit of a culture shift in our team at the time. 

(50:25):
And I actually think that's kind of carried me through my entire career, which is trying to figure out how to share the product management load so we're equally responsible for what we're building. So that was a good unintentional learning that I think has been really important for my career. I think that part of that learning that I've had obviously here and in London as well was the figuring out how to make room for creativity. So in Shanghai and also in London at the time, this was a decade now so many things have changed since then, there just didn't seem to be as much room for ideas to come from anywhere, which I think is also related to what I've seen before. 

(51:13):
So making space for people across functions to share ideas and then across geographies to share ideas, especially in companies where English might have been the primary language but most of the employees were not native English speakers, there was a lot of time I think that I felt that I wanted to spend, and I did, on just creating space for people to comfortably share their ideas honestly. And that for me was really formative because I think it's really impacted how I've approached my entire career and I don't know that I would have, had I not had those experiences.

Lenny (51:52):
I was browsing through your LinkedIn post and you said something just like that on LinkedIn of just how formative that experience was for you. I know it's not something people can just say, "Hey, I'm going to go to China and work for a startup," but it sounds like you recommend working at companies of different cultures because it feels like it is a lens.

Nikita Miller (52:10):
Yeah. I do. I also think my family, I'm Jamaican, I'm a Jamaican immigrant, and so all of our experiences inform how we perform our jobs and how we think about problems. And being able to expand that, yes, I would recommend it to every and anyone that gets the opportunity. And I think it's really important as product managers because I think it's really hard to be a product manager if you cannot empathize with the people and problems that you're solving for, and being out of your comfort obviously is one way to learn empathy.

Lenny (52:50):
I love that. One final question before we get to a very exciting lightning round, not to not count those questions. Are there just any frameworks or processes or methods that you found to be very valuable in your career as a product leader that you would want to share?

Nikita Miller (53:08):
The question I ask myself and I ask everyone in my life probably, whether it's on my team or when folks, friends talk to me, I always ask, "What are you optimizing for?" That's the question, it's what are you optimizing for? And it's the short, medium, lon-term in product, but it's what are you optimizing for today, this quarter, this year? Whatever time horizon. And I think that can be just a really illuminating way of thinking about obviously just how are you spending your time? And I think it works for product as well. Every time we talk about OKR or goal-setting, ultimately it is what are we optimizing for some period of time. And I think that always for me, whether personally or in product, is very illuminating.

Lenny (53:53):
I love that. I'm pretty sure I've asked that question 1,000 times myself. One thing I find though is people get annoyed with you just like, "Okay. You're such a PM."

Nikita Miller (54:02):
I know, but it works.

Lenny (54:05):
It does work. What are some instances where you deploy this question? Is it in a meeting where someone's asking a question where you're just like, "What are we optimizing for here?"

Nikita Miller (54:14):
I ask this question all the time. I ask this question to my husband. What are we optimizing for?

Lenny (54:17):
I'm sure he loves it.

Nikita Miller (54:19):
He was a PM too, so he gets it.

Lenny (54:20):
Okay, okay. That's helpful.

Nikita Miller (54:23):
I ask this to my five-year-old, honestly. We talk about it a lot. Now we're going to quarterly planning, all of us, and now we have information from Q1 so let's look at it and say, "Given what we know now, what are we optimizing for? Because it might not be the same thing we did before with new information or it may be," and that's usually just then helping us get better at figuring out obviously how we're doing trade-offs-

Lenny (54:55):
That's awesome.

Nikita Miller (54:56):
... because if the first point isn't clear, then the trade-offs aren't going to be clear.

Lenny (54:59):
Yep. The other question is what problem are we trying to solve here? I feel like I need to make mugs and put these some mugs for product managers. Well, with that, we've reached our very exciting lightning round. I've got six questions for you. Are you ready?

Nikita Miller (55:13):
Yes. I don't think I prepped this, but I'm ready. Yes.

Lenny (55:16):
Okay. Well, it'll be the most fun then. What are two or three books that you recommend most to other people?

Nikita Miller (55:23):
These are not product books. I recommend Anna Akhmatova's You Will Hear Thunder, a book of poetry that is excellent. I recommend almost anything by James Baldwin, The Fire Next Time I most recently reread, and back to software, High Output Management.

Lenny (55:43):
What are some favorite movies or TV shows they've recently watched that you really enjoyed?

Nikita Miller (55:49):
I am really into K dramas right now, and actually-

Lenny (55:52):
Is that Korean?

Nikita Miller (55:53):
... Korean dramas right now. Crash Landing on You, it's great. It's a love story.

Lenny (56:01):
That's wonderful. Very out of the box. I love it. What's a favorite interview question that you like to ask?

Nikita Miller (56:08):
For product managers, we think about product in the context of artist, scientist, general manager. Where do you spike?

Lenny (56:15):
Artist, scientist, general manager. Interesting. And is there one you ideally look for the answer or it depends on the role you're hiring for?

Nikita Miller (56:23):
It totally depends on the composition of my team.

Lenny (56:26):
Interesting. Cool. I like that. And a different triad. What's a favorite product you've recently discovered that you love?

Nikita Miller (56:33):
Arc by The Browser Company. I think they're a product that's clearly having a lot of fun and you can feel that in the product. When I first opened it, they have an unveiling experience, which isn't something you'd expect of a browser, and there was something really delightful about it.

Lenny (56:51):
Yeah. I imagine you've heard the interview with Josh. 

Nikita Miller (56:55):
I did.

Lenny (56:55):
What a guy. What a cool product. I love it. We have a whole hour and a half on it, so check that out if anyone wants to learn more about Arc. What is something relatively minor you've changed in your product development process that has had a tremendous impact in your team's ability to execute?

Nikita Miller (57:11):
Helping product teams try and use product, design, engineering and data to understand their shared roles and responsibilities.

Lenny (57:19):
Awesome. Call back to our previous discussion. And final question. What's a pro tip for someone trying to use The Knot and or one of the other properties?

Nikita Miller (57:29):
Ooh, good question. Two things, but the big one is probably checking out The Knot Worldwide marketplace. It is the most comprehensive two-sided marketplace to find your wedding vendors to create your wedding team, and you'll find that they're really cool small businesses on there.

Lenny (57:47):
Awesome. I'm going to go check that out. Nikita, thank you so much for being here. I'm going to go and ask my wife what she's optimizing for and read some stuff on the phone.

Nikita Miller (57:56):
Good luck.

Lenny (57:57):
Wish me luck.

Nikita Miller (57:58):
You said she's pregnant, right? She's optimizing for creating a human probably.

Lenny (58:02):
Yeah. That seems right. Okay. I'm not going to ask. Two final questions. Where can folks find you if they want to reach out and learn more about what you're up to and how can listeners be useful to you?

Nikita Miller (58:13):
You? I'm on Twitter and LinkedIn, easy enough to find me. I am very responsive actually, or at least I try to be when folks reach out on anything product related. And ask me questions. I think that's always helpful. If you have other ways of doing things, I'd love to hear about it.

Lenny (58:29):
You mentioned also that you're doing some angel investing. Is there anything you're looking for specifically that you'd want people to ping you about?

Nikita Miller (58:35):
I am doing some angel investing, maybe a little bit less so recently, but I'm starting to ramp that up again. So if there are any early stage seed or pre-seed companies out there, you can ping me.

Lenny (58:47):
Amazing. Nikita, thank you again so much for being here.

Nikita Miller (58:50):
All right. Thanks a lot, Lenny.

Lenny (58:52):
Bye, everybody.

Nikita Miller (58:52):
Bye.

Lenny (58:55):
Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.