Lessons from Loom on product strategy, organizational leadership, and cross-functional performance | Anique Drumright (COO at Loom)
Episode 100

Lessons from Loom on product strategy, organizational leadership, and cross-functional performance | Anique Drumright (COO at Loom)

Anique Drumright is the COO at Loom, a video communication tool for streamlining workflows. Loom has raised over $200M, and was last valued at $1.5B. Anique has a proven track record across product development, executive leadership, and building high-performing organizations.

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Anique Drumright is the COO at Loom, a video communication tool for streamlining workflows. Loom has raised over $200M, and was last valued at $1.5B. Anique has a proven track record across product development, executive leadership, and building high-performing organizations. Before joining Loom, Anique was the VP of Product at TripActions, where she scaled the team over 8x globally, and she has also held multiple roles at Uber.

In today's episode, we discuss:


Where to find Anique Drumright:

Twitter: https://twitter.com/aniqued

LinkedIn: https://www.linkedin.com/in/anique-drumright-53978a1a

Where to find Brett Berson:

Twitter: https://twitter.com/brettberson

LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/


[00:03:00] The similarities and differences between PM and executive leadership roles

[00:06:53] How Loom uses storytelling when launching a product

[00:10:01] Managing cross-functional scope and performance

[00:13:41] Goal-setting with functional leads

[00:16:59] The importance and difficulty of organizational alignment

[00:20:40] How Uber achieved alignment at scale

[00:24:06] Rituals for staying aligned

[00:25:23] Loom's winning one-on-one format

[00:27:49] When and how to help functional leads

[00:29:13] Hiring for roles outside your area of expertise

[00:32:55] Go-to interview questions for prospective leaders

[00:33:55] Changing the hiring process for roles outside your area of expertise

[00:36:09] Common patterns of failed external hires

[00:37:40] Common patterns of failed internal hires

[00:39:05] Avoiding over-promotion in your organization

[00:40:51] What inspires people in a company

[00:45:40] Tactics for getting honest answers in interviews

[00:47:12] Asking the right questions during reference checks

[00:51:29] A month in the life of a COO

[00:52:52] The importance of employee energy levels

[00:54:53] Loom's leadership dynamics and why it works

[00:57:30] People who had an outsized impact on Anique's career

Brett: I thought maybe one place we could start is, I think you're about a year into being a COO for the first time after kind of being quite functionally oriented spending, I think most of your career in various versions of product management. I'm always really interested when somebody takes on kind of an adjacent role like. What has been interesting or surprising for you? 

Anique: I don't know if this is surprising, but more confirms how interconnected product is with marketing, with storytelling and how that connects to customers. And I think it's really confirmed just how central product is to the customer experience and how the various functions support that and influence one another.

Brett: So maybe on that point, if you were to go back and lead product again, what are like the things that you've observed in this role that might make you think differently about what you would do as a product person, if anything?

Anique: I think a best practice that is too often glanced over is what do you wanna see in the market?

What do you wanna say to your customer? How will you explain it? In really beginning, every product review with that, you know, the first principle of what do you think the impact of it will be? But I think starting with the storytelling of what this feature, what this new offering will do, and starting much more on, on the marketing side rather than on the functionality side or even the opportunity side.

I would probably start earlier with that. 'cause I think it creates a lot of cross-functional clarity.

Brett: What does that look like in the context of loom? 

Anique: So I think an example is everyone's building with AI right now, and so I think initially it was like, okay, what are the capabilities we could use? What's the functionality we could use?

But really starting with how could we make this easier for a creator to connect with their audience? And what do we want the creator to be able to say and what do we want the audience to be able to say? And starting in many ways with the product marketing and how we'll explain that moment in product has been, I think, hugely helpful.

Whereas I think when I was just wearing my functionals, I think too quickly and too easily, we began with execution. And so I think it's evolved the way I think about key customer experiences. 

Brett: And how does that connect with this idea of marketing and storytelling? becasue you're starting with the story of the value you're gonna provide.

Anique: I think all good product management starts with it, but I think it's often something that like begins with, you know, that five minutes, this is how we'd explain it to a customer, rather than saying, this is the key moment we wanna create over the course of the next three months, the next six months. This is what we think the value will be to the customer base.

This is how we would frame it for our customer base. This is what we think the value of the business would be. And spending a lot more time on that almost product marketing moment earlier on, I think brings your cross-functional team with you much faster. Rather than making it a by the way and spending a vast majority of your effort on the product review, the feature requirements, the designs, all of that is still incredibly important.

But I think I underestimated how clarifying that best practice is in bringing your cross-functional team together. And I think it builds a better product because you're spending a lot more time obsessing about what the value you're trying to bring to the customer is. 

Brett: And so is your sense that should be driven by the PM who's owning this thing?

Or a product marketer or it kind of depends.

Anique: I think it depends. I think it like depends on where your team's strengths are. I also think those are really perforated lines, right? Like the line between a designer and a product manager, perforated like product manager to engineer perforated. And I do think it is a collaboration.

Ultimately, I think the product manager needs to be driving that perspective in its totality, but I think there's room for various functions to take the lead.

Brett: So maybe when you think back to the last six months and the products that you've shipped as an organization at Loom, when you think about really nailing this idea of storytelling, is there one thing the company launched that most comes to mind, and what did that look like?

Anique: It's like product managers and designers. We were excited about this idea of auto packaging. This idea that we could magically make a loom better with less effort from a creator and it would land better for a viewer. 'cause something that we had learned from talking to creators and talking to viewers is like, viewers really want context as to what their loom is about and creators really.

This makes a ton of sense. They really want their loom to land. Their viewers are what motivate them, right? Who they're communicating with are what motivate them. And also the number one thing that they value with Loom is that it's super fast and it's super simple. So how do we make that connection automatic?

And so we talked a lot about this idea of auto packaging and auto context, and you know, over the last few months we've released automatic titles and automatic summaries and automatic chapters. And this idea of packaging your loom automatically. What we're seeing is creators love it because it's less effort.

There's the right amount of delight and utility. 'cause we give you your title and we select an emoticon for you. And from a metrics perspective, the viewership is going up because I have richer context. And the loom itself is more engaging. And I think that's one where we haven't been sharing about it a ton externally, but the storytelling we told internally around ourselves around hey, what is the set of features that package this loom automatically and help make creators more successful in providing context to their viewers? Really helped clarify what we wanted to put in scope of this initial push. 

Brett: And so what did that look like when it was getting kicked off in terms of getting things off the ground, aligning around this narrative?

What's going on at the beginning before any features and functionality is articulated.

Anique: I think we're really lucky to have a great user research in design partnership, and they also work really closely with our product marketers and product managers. And so it begins with a real synthesis and internalization of, Hey, these are the customer problems we wanna solve, and these are the new capabilities we believe in, and how did these come together?

But I do think that our product design team, especially at the initial kickoff, plays a really large portion in setting the, what's the vision of what we wanna do and why do we wanna do it? 

Brett: And like what's the deliverable there? Is it like a multi-page doc that tries to articulate what this narrative and set of value props might look like, that then gets shared with the team and people kind of workshop it.

Anique: Yeah, that's generally what it starts. It's the product manager starts with the PRD. The designer plays a really large role in like leveraging the UXR that already exists and really framing up the customer problem. And between the PM and the designer, they say, Hey, this is the headline of what we wanna create, and this is the feature set that we think between the effort impacting confidence rubric we're recommending. 

Brett: I'm I really interested to learn more about what your process is for getting your arms around these other parts of the org that you didn't come up under. When you end up in the COO role, you end up having sort of this span of scope that's quite cross-functional. 

Anique: Yeah, I think it's a very. Interesting question.

I think that the place that I always try to begin with is just re-anchoring myself because I think every function connects differently to the business's stage and the business's strategy. So I begin with trying to re-anchor to myself, Hey, what is crucial for the company right now? And like, where does this function support?

Where does marketing really need to get an A at? Where does data really need to get an A at? And just re-anchor myself on the like broader context that we're functioning under. And then from there, I just begin with information gathering. Just trying to understand what's the team currently working on? What do they think they really need to get an A on?

And just slow down to listen. I think the next kind of double click I do is with critical stakeholders. So for data, for example, what does my sales leader think? What does my customer success leader think? What does my product manager think? What do they believe should be the priorities for data based upon what they need to achieve from a business perspective?

And then from there, I try to align with the leader on do we have a shared definition of, of what we're trying to get an A on and why? And that's really like the starting point of the work is that clarity on how does this function connect with the broader business context and strategy, and are we aligned on what the priorities are?

Brett: And is that just happen through organic conversation or have you developed some sort of process or approach to create that type of alignment? 

Anique: I definitely go through this process. So I'm a big believer in writing down like the three things that any organization, any function really needs to be absolutely crushing at for the next three months.

'cause I think it's really clarifying. I think especially at a startup, the work, there's so many opportunities and there's so many problems, and there's such a dearth of systems. So you're building the business while you're building the product, and you're building your systems all at the same time. So there's a never ending list of things that you could improve.

And so I think getting extremely clear on what the priorities are and how those priorities support the business helps you also say no to a lot of things. And so the process that I always go through is I re-anchor myself on like, okay, what's the business strategy? What is my own instinct on what I think needs to be going on.

I then go, listen. I meet the team, I listen to what they're doing, and I really try to learn about their workflow. I then try to learn from the cross-functional stakeholders, so you could call this phase more of a traditional listening tour. You talk to your customers and then after that it's okay.

Between me and the functional leader, are we aligned and what is the refreshed set of priorities? and then from there, it's okay. What are the couple of things we can just trim and stop doing? What are the couple of things where we can be more efficient? And then a question that I often try to ask myself is like, where can I support in making the cross-functional ties stronger?

You know, when people are exhausting themselves, it's because there isn't cross-functional alignment. And the reason why there isn't cross-functional alignment is because. I'm probably not creating that signal to noise that helps everyone independently prioritize and feel like they're playing off the same plan.

And I haven't done a good job of saying, oh, no, no, no. We actually, we can pause on this because this other thing is more important. But that's generally the framework that I'm consistently trying to use. And then I'm usually like rinsing and repeating that cycle every two months or so. 

So when you think back about a cycle from like the past six or nine months, What's an example of the three goals or priorities?

Because I'm curious like at what level of altitude you think is most effective for those type of governing goals? 

Yeah, so I think, you know, the most recent example is we just hired a new marketing leader, a new VP of marketing at Loom and so as part of finding that leader, I had to really re-anchor myself as well as our CEO on what do we want this person to be really, really great at, and what does Loom really need for the next 12 months? And the level of the goals is we really want someone who's like great at growth marketing. And when we say growth marketing, we're really talking about paid marketing, we're talking about SEO, and we're talking about positioning and we want to be great at those three things.

Brett: And that feels like one sort of functional example of getting really clear on kind of three goals. Is there an example of the cross-functional three most important things that then guide sort of everyone's work? 

Anique: It's how we do our quarterly planning is based upon like high level like key deliverables that we want to achieve over the course of the next three months.

But then we meet every Monday to cross-functionally to review the key customer moments. And that's something that we've recently started of like, Hey, these are the five like key critical moments that we wanna achieve over the next three months, and we all cross-functionally go through that. So it's brand, it's product marketing, it's data, it's product management in sales.

And we're essentially having a staff meeting saying, Hey, these are the critical customer moments over the course of the next 90 days. Are we all aligned against them and are we all prioritizing against them? 

Brett: What's an example of a customer moment? 

Anique: So one of the like easy customer moments is we're releasing Multilanguage transcripts.

Loom has a wildly large international base for right now. You know, your closed captions and transcripts are only in English, so we need to be ready to support that in multilanguage. Another one is, Our AI editing suite, how do we go from how user, community and beta community to GA and how do we amplify that and make sure that it's the highest quality it can be through validation with customers as well as landing in market.

Brett: And so for those five areas, you wind up sort of reviewing those with your functional leads on a weekly basis. 

Anique: Yep. 

Brett: And what is the structure of that meeting end up looking like? 

Anique: The structure of that meeting is we begin with, there's like a visual of what the customer journey looks like over the course of the next 90 days.

What are the key customer touchpoints of admins, of creators, of paying customers, of our free user base, et cetera. And then we go through each one of those releases. In that chronological order, you know, 'cause not a single PM is overseeing every piece. Not a single designer is overseeing every piece. And so that we can hear, okay, what's the feedback?

What are the things that we said we were gonna solve cross-functionally last week? Did we solve it? Cool. We close out that piece of release and we go to the next piece. And so it really helps us begin our week together and so that we can hear from each other cross-functionally what we need to rally around to achieve these key customer moments. 

Brett: Why do you think alignment tends to be so difficult in companies of almost any size? I was actually talking to a CEO that we partnered with for many years and we were talking about it randomly alignment last night, and it's one of those things that intuitively makes sense, but I feel like most companies at any given time aren't in alignment in almost any facet.

Is there a reason that it seems to be so difficult to operationalize or action on? 

Anique: This is a much more philosophical answer, but I think the reality is this, that we're humans. I'm different today than I was yesterday and the day before, and I'll be different a week from now. And I think, you know, a company is just a bunch of humans working together and so your perception of what the plan is and your belief and understanding of the plan is evolving.

And because everyone is evolving, you have to evolve the system together. I think that's why people spend so much time on alignment is it's, I think it's the reality of teams working together and I think the promised land of like alignment is when people have when the what and the why is like pulsing through you.

And it's, it, that same version is pulsing through everyone and, and you feel it as a team, right? There's like moments of Oh yeah, yeah, yeah. Like we all know the what and the why and, and we're fired up about it. The autonomy and the velocity comes with it and it's why you see people fight so hard when they're out of alignment.

It's 'cause you're always trying to get back into that tempo run. In some ways 

Brett: When you think back across your career thus far, what are the moments where you felt that the most? 

Anique: I think there were definitely times in my journey at TripActions where the what and the whys was so absolutely clear. I definitely felt that way, and like I would say right now at Loom, I feel that way in the sense of there's just such a belief that the capabilities of AI can be used to just further the experience of creators so intensely that there's just this excitement and a clarity of the opportunity in front of us that the alignment is much clearer and much more simplified. And I think if I were to like double click on both of those experiences, I think the way larger tech companies have evolved is you know, you have your 12 autonomous teams and they're running in parallel. But in both of those experiences, the one I'm currently having right now and the one at TripActions, we're actually running off of one plan. And there's absolutely a divide and conquer. But I think when there's too much of an effort to parallelize, then you lose that sense of alignment and that sense of broader mission.

And I think in both of those moments of time, there's only one play, you know, and that play may have three or four steps, but it is singular focus. 

Brett: Do you think that a lot of companies can have a meaningful percentage of that time where everyone is aligned to sort of get to the top of that hill, or it's just the nature of scaling businesses that.

You have a bunch of people that are charging up their own hills and that's just sort of a constraint of bigger businesses.

Anique: I think it's definitely possible. I don't know. I think back to my time at like Uber 2015, everyone really was trying to make transportation as easy as running water. And I would say that company when I joined was in the thousands, right? I think it was 5,000 when I joined and it, it scaled. It probably doubled over the couple of years I was there. I do think it's possible at scale now. Do I think every single step, every single day by every person is as synchronized? Probably not. But I also think if that mission is so clear, I also think you see goodness in in bottoms up ideas.

You see really hungry people pitching smart ideas, and those ideas may be executed on, or they may be like, yeah, not right now. But I think that, I do think it's possible. 

Brett: So if you were to deconstruct, well, what's happening in Uber at that time, what was sort of the setup or the conditions or the rituals that created that type of alignment at pretty meaningful scale. 

Anique: I think there were probably two rituals as a person who was like new to the tech sector, new to Uber, that ended up being really powerful. I think first there was like an extremely healthy all hands culture and then if you like double click on what was presented in that All hands.

It was all about rides, it was about global rides. Global drivers. And that was the exact same thing that was being presented in many ways in the regions on like the city teams and regional teams. It was all about rides. What was the best week ever for rides? Did you have the best day ever, et cetera. And so there was just everyone in the company knew what metrics we were excited about and we were obsessed with.

And then I think one of the most impressive. Onboarding experiences I ever had was 2015 Uber. I remember one of the finance leaders basically gave the economics of an Uber ride, and it was such incredible context for every single employee at the company to have. And so everyone operating from the foundation of, there's all of this excitement and these are all of the strengths in the market, but also this is very much like where we're vulnerable and why we need to be so protective of the unit.

Economics was incredibly empowering. Right? And I was just a new person an IC joining the company, but I think the repetition on the metrics as well as the context so early on enabled everyone to be an owner. 

Brett: How do you know if you're in or out of alignment as an organization? 

Anique: I think there's the inputs and there's the outputs.

I think the outputs, everyone instinctively knows. The outputs generally look like you're shipping slower than you were. Another output would be a lot of people are asking a lot of clarifying questions, right? I think another example is one function's moving really fast on a product launch and another function doesn't even realize.

But I think those are all the outputs of misalignment, and I think there's many different indicators. I think what I have learned is when launching a new initiative or when rolling out a three month plan, a six month plan, et cetera, you always wanna preview it. You don't want anything to surprise anyone.

You wanna get lots of informal feedback ahead of time so that critical leaders and partners. One you like heard their high quality feedback and had the opportunity to execute on it, but also that they can be partners in creating that alignment and creating that clarity and that they're able to provide way ahead of time.

And when I say way, we're talking about startups. So I'm talking like five days, 10 days. Give me a week or two to create the cross-functional alignment that they think they're gonna need in order to succeed. Here's a really easy example. We way amped up. Some of our growth marketing targets, and we shared 'em with the company last week, but probably three or four weeks ago, both like the marketing leader and the data leader and the brand leader were able to say, Hey, various prioritization's going to have to occur in order for us to achieve this.

And all of that leg work was done ahead of communication rather than before. So when it's communicated, everyone's feeling confident that they're going to be successful. 

Brett: You talked about this a little bit in the context of Uber, but once you have a clear plan and folks are aligned around it, what do you think are the most important ongoing touch points?

Anique: I'm a big believer in the end of a four week do a review. And when I say a review, I don't mean 30 people need to sit together, but it's, Hey, these are the things we said we'd get done in the next 30 days that connect with what we're trying to achieve, what's our progress plans and problems, and how would we grade ourselves? Red, yellow, green. And then I'm pretty formatted in how I do one-on-ones. And one of the key questions is, what's your perspective on your team's execution Quality. Red, yellow, green, big fan of binary questions. 'cause I think it forces clarity and like how are your big three rocks going? And so I think between the weekly staff meeting, the one-on-ones and how it connects to this like 30 day template, it really supports consistent alignment and reflection.

And are we all seeing the world the same way? And then our exec staff, Has a very similar format. I think one of the big changes that Joe and I have worked on is just ensuring that on our exec staff, we're spending most of our energy on the biggest growth levers in customer deliveries, rather than getting distracted by all of the operations that is building a startup.

Brett: Maybe you could expand on what the overall format of the one-on-one is.

Anique: So the one-on-ones are the standard questions of how would you grade your OKR, what is your team crushing at? How can I be helpful? And then hot topics. But I actually think the most telling questions are the top two. So the first is, What's your energy?

Red, yellow, green. And then how would you grade your execution? Red, yellow, green? Because I think both of those questions, especially in like a remote global team where you're not in office every day, give you the best indicator on how your critical leader is feeling and helps you understand where execution is falling down, and how on track are we to hit the goals that are within their domain, because very rarely is someone on track for like a great product launch, a great closing of a sales deal, and then they're red on energy and red on execution. Like how we perceive our work is the input to our outcomes. I think for me, it gives me the greatest indicator of where I can support and in diagnosing. How likely are we to achieve our goals?

Brett: So when you think about a 20 minute or 30 minute or 60 minute one-on-one, where does most of the time end up spent along sort of that framework that you outlined?

Anique: I do 30 minute one-on-ones. Because I do 'em weekly, I think about five to 10 minutes get spent on the first two question, the what your team is crushing at, I read asynchronously, but it's also to remind leaders that their team is crushing at things.

You know, it's too easy to look for the problems. And so that question is almost for them and not for me. And then depending on how like the kind of key goals are trending and how they grade them we may spend a couple minutes on them or very little, and then I think we generally spend about 15 minutes on the hot topics.

Brett: And hot topics are just a catchall basket of 

Anique: Yeah, it's generally like I am, I'm concerned on our new calculation for CAC great. Let's talk through that. How can I be helpful? We're hiring for this role. What's your take on it? This is how I'm thinking about it. We need to close scope, we need to narrow scope on this feature set so it, it is a catchall, but I think the beginning format creates focus and gives me a really good line of sight into how is this leader doing and how do they perceive their work and when they grade their execution and likelihood to hit their goals.

What is it amounting to? 

Brett: What are the problems that you should be helping one of your functional leads figure out versus what they should be figuring out on their own as a functional lead if they're operating at an appropriate level? 

Anique: I think this is such a good question, and it's one that I'm like often calibrating with myself on.

I think it depends on tenure, right? So if you have a new VP or a new director coming in, I think you're in like a trust but verify mentality, definitely for the first 30 days, but into the first 90 days, 180 days, you should no longer be there. But I think the first 90 days, you're still in a support function.

I generally think cross-functional relationship building, this isn't going well. That's not going well. I think as someone is becoming more senior, you shouldn't be spending time there. That is just a core leadership capability to work cross-functionally. But I think where you end up spending time is actually sparring on the choices and the decision making.

Like, Hey, we can go deep on this analysis, but we won't have time on X, Y, Z. Or we can fund three parts of the product strategy, but not four. This is what I think we should give up. What do you think about that? I think as people get more senior, you spend more time on the judgment and the decision making that's gonna impact the business and the humans we work with every day. And you spend much less on, on the interrelationship piece. 

Brett: So we talked about this at the beginning of the conversation, this sort of idea of developing expertise and instincts and areas that are not in your power alley. And I was interesting in looping back on that you mentioned you recently hired a new marketing leader, and maybe we can zoom out a little bit and talk.

Talk more about how you think about hiring or the functions that, in this case, in the context of your career are not in product and how you get good at that. And maybe we could specifically talk about the marketing leader search as kind of a case study given you just, you just did it. 

Anique: Again, this is why I think product is really helpful.

Like I began with a mini listening tour. I talked to CMOs in my network and in like Loom's network to just educate myself on the role, how they assess the role, what would be strengths that they would look at given our business dynamic and what are parts of the marketing repertoire that you would really want someone to be great at.

And so I think phase one was really just acclimating myself and leveraging my network to develop an instinct for myself on what I was looking for. 

Brett: As you do that listening tour, are there specific questions that you find are particularly illuminating? 

Anique: I think the question that I asked that was the most helpful as I did community interviews or like network interviews was, if you were coming into Loom, what would be strengths that you would be hiring for?

Given what I'm telling you about our PLG motion or sales led motion, what would you consider growth channels that would just be a non-negotiable for you? It enabled me to like develop an instinct much faster on what I think we should value and you know, how do you balance like expertise externally with internal instinct.

And what's the Venn diagram between those two? 'cause when you've worked at a company for a couple of years and you're working with founders who have been working on something for, you know, five, six years, they have their own instincts that are very much real and have a lot of value. And what's the Venn diagram between those two?

But I think anchoring it on, if you were coming in, what are the strengths you would look at to contribute to our growth story was very clarifying. 

Brett: Did you find that the most useful conversations are people that are leading marketing orgs at companies that are shaped very similarly to Loom, or you found learnings from a hardcore enterprise top-down leader, a variety of other companies that look somewhat different from yours?

Anique: I did a mixed bag, but I definitely made sure that I talked to two or three people from specifically a PLG business because I do think with a PLG product, the line between product and marketing is very perforated and sales, right? I think it's why it's such a like an emerging area of expertise, but I definitely also talked to people who had a more traditional sales led background because that's also really valuable as we build a sales motion.

Brett: So continuing on down the journey, you, you sort of begin with this idea of building context through talking to other folks in somewhat similar, maybe dissimilar marketing roles. Then what happens? 

Anique: So, yeah, after the listening tour, I again re-anchored myself on what do I know about our business strategy over the next 12 to 18 months and what do I believe that this person really needs to get an A on?

And what are their skill sets that I'm saying, Hey, this person doesn't, isn't an A plus at this one thing. Let's say PR, for example. That's okay because we have other strengths on our existing team that will make up for it. And then I just ensured that Joe and I were aligned and then I spent a ton of time trying to curate who was interviewing, was it cross-functional in nature enough?

And then just preparing for my own interview assessment, 

Brett: what does that look like? 

Anique: Me preparing for interviews. So for this one specifically, yes, I absolutely went through the standard tell me about your last three roles. What did you achieve? How did you achieve it? Biggest learning, biggest accomplishment, and I always exclude the team because I think a lot of times leaders will say, my team's my biggest accomplishment.

I'm like, yeah, yeah, but I wanna know what, what your team achieved and how it achieved it. And so I purposely say, you cannot say team, like what was truly your biggest business accomplishment? And then what's your biggest failure? But I think the best question that I've learned to ask whether I'm a cross-functional interviewer or the hiring manager is, and this is specifically a question for leaders, your entire team disappears overnight.

What's the skillset you hang your hat on? Because I think it tells you as a hiring manager or as like a cross-functional person interviewing. What is their killer skillset, and it also tells you, especially as a hiring manager, what are probably the one or two skill sets that they're gonna be hiring for to just round themselves out as an organization.

Brett: If I were to watch you interview for this marketing leadership role relative to a product leadership role underneath you, other than sort of that context setting and learning at the beginning by talking to other people who are really excellent in this function. Are there other differences in overall process, methodology approach for these areas that sit outside of your core area of expertise?

Anique: I think the difference is the learning tour at the beginning, but I still think I, I start with, what am I trying to get an A at? What's a project that would be an indicator that this person could get an A on those things. Okay, create that project. 

Brett: What was the project? In the case of a marketing leader, can you kind of give an example of what it looks like?

Anique: Yeah, so I did a two part exercise. I think the first was the standard about you proudest accomplishment, like what's the story arc of your career, what's your biggest accomplishment in case study from the last company you worked at, or the one prior. I think that's a pretty standard exercise for a leader.

Brett: And they present it as like a case study to you? 

Anique: Yes. They presented as a case study via loom. 'cause we're a loom and we prep asynchronously and it's also really nice 'cause then the take home is completely scalable to everyone who's going through the interview loom. And then the second part that I asked for was like, take a look at at looms footprint today. How would you diagnose. Like our marketing footprint and how would you build a gross marketing plan for us? And I think it enabled me to see how hungry was someone, right? So how in detail did they go on our footprint? How scrappy were they in terms of using just open tools on what our traffic was, how many people are coming to it, how do we compare to competitors, et cetera.

And then it also enabled me to see the framework at which they break apart problems. And so that was also a presentation in a loom. 

Brett: When you think about other projects for other roles, does it tend to look somewhat similar to that? 

Anique: The project always reflects something about, tell me about yourself in a case study, because I think it's scalable for the candidate and it enables you to see what they consider their, their strongest body of work in their storytelling.

But then the project I always assign has to do with what I need this person to get an A at. 

Brett: When you think about the hiring errors you've made where you hired person X and thought they would be exceptional and you had to let them go, did you notice that they clustered in a certain set of patterns that you've now updated your process on?

Anique: I think there's two buckets to that question. I think bucket one is internal, like building your bench internally, which is. You know, a really important thing at a startup, and then there's hiring externally. So I'll answer the question for hiring externally, but I actually think they're two separate reflections for me.

I think on the hiring externally when I've gotten it wrong, I think in my gut, I've always had the doubt. I think earlier on, if I didn't have a really clear reason, I would try to talk myself into it and I'd look for evidence. And now I'm much more inclined to slow down and investigate my gut, and especially in the broader interview cycle if there are flags or concerns.

I slow down to investigate it. It's like I really, really slow down to investigate it and I change like the back channel process and the references based upon it. And then I would say the other piece, which is much more of a skillset that I think is critical at a startup where you're trying to move quickly into your questions on alignment is clarity of communication.

So if in the interview there were concerns on clarity of communication, both written or verbally for specifically product ops marketing data roles, which I would say are heavy storytelling in cross-functional roles. 

Brett: What about the second category? I think you were saying internal recruiting maybe? 

Anique: Yeah, so I think something that is really exciting about being at a startup is getting the opportunity to try new things. But I definitely think there are times where, you know, you're building a bench and you, you place a bet, you make an investment and it doesn't quite work out the way you were intending, or maybe you sat on that investment a little too longer and you know, the role and the complexity is actually just bigger than, than someone is able to grow.

Something that Ariel at TripActions used to tell me. He's like, you know, you need to reinvent yourself every three months because the business is gonna change every three months. Reinvent yourself, figure out how to uplevel yourself. And I do think that that is largely true. And so I think one of my big reflections is literally one of my favorite parts of being at a startup is, Watching people take on nebulous problems and have outsized opportunities that are business aligned.

But I think the verification process that it's going well along the way is really important. And when I say the verification process, it's that trust and verify saying, so it's not only is the output happening, but also what's the perception of the cross-functional stakeholders? Are their impacts being optimized and maximized?

And are you creating a rich feedback loop as you're taking risks on growing leaders? Trusting, but verifying has been. Definitely one of my key learnings over the last five years. 

Brett: Is that how you avoid the Peter principle. The Peter principle, is this sort of idea in general management that almost everyone is promoted one rung above their level of competence.

So let's say you have a super star product manager, right? And they're super ambitious. Then they become, and they really want to be a senior product manager, and then they do an awesome job as a senior product manager. Then they want to be a group product manager to do, and eventually what what happens is not everyone, but a vast majority of people end up one rung, effectively over promoted.

And so they go from a rung where they're exceptional. To one where they sort of cap out. And so you, you have this issue of where you, you've taken someone who was really effective and you've pushed them beyond their capabilities and so they become ineffective. 

Anique: I think when I'm doing my job poorly, that happens.

And have I made that mistake before? Yes. But I think when I'm doing my job well, people who are getting promoted are already doing the job, like they've been doing the job probably for the last. Three to six months, and I've been doing a really good job listening in the process and not just listening to them, but listening to the people that they impact as well, who are seeing that next level of detail.

Are they inspired to be working with that person? Because I think all of us who choose to work at startups, we have a Superman gene. We wanna help create a world, whether it's a working world or a social world that is different than the one we're currently in. And so I think the two ingredients when I'm doing it really well is listening.

And that's really what I call this like trust, but verify. And in listening to understand is like the work getting done at the level that I think the work should be getting done at. And also, are the people that are cross-functionally working with them, are they inspired? 

Brett: Can you help people inspire other people?

Or, it's a little bit like charisma, like most people are either charismatic or not. 

Anique: I don't think it is. So I have a non-traditional background to tech. I was with Teach for America for five years and I think one of my biggest learnings from being in the classroom was the what and the why. My lessons where the what and the why were clear always went so much better than when I was just like having someone, you know, draw their arrays.

I'm like, we're just doing arrays. Just get them done. I actually don't think it's any different with product management or leadership. I don't think it is charisma. I think you can actually have a lot of charisma and when the what and the why isn't clear I don't think you're really getting a true inspiration.

I don't think it's internalized. I don't think it's linear enough to truly sustain for a period of time. I don't think it's possible on just charisma. 

Brett: And so on this topic of inspiring a team or a group of people, when you work with folks on your team that are trying to develop. That skillset. And you explain how, what sounds like a meaningful percentage is the ability to clearly articulate the what and why.

Are there other things you are doing to sort of teach someone how to do this? 

Anique: I'll just give a recent real life example. 'cause I think it's the easiest. So I was in a, a one-on-one with a new leader who's in a very cross-functional role, and they were telling me, I really just think we need to make this a company priority.

It's the only way it's gonna get done. And I was like, I think the resources are there. I think you need to spend time sharing context and inspiring cross-functionally. And I think that your cross-functional stakeholders don't have enough context to know how this relates to the top line company goals. I don't think me editing the company goals is the way to solve this problem.

I actually think context is the way to solve this problem. And then, you know, this person fairly asked, they were like, well, do you have an example? Is there an example of how you, how you think this should be done? I literally just pulled a couple of looms from people that I believe were our strong product managers, or I pulled one from design and I just showed different disciplines of giving context and giving data and potential impact.

If someone's joined a company, they're already bought in, they already wanna win. That's like why we all come to work every day. That's why we choose to work at a startup. We wanna be creating new value in the world. My assumption is that the motivation is already there and when there isn't motivation, it's 'cause the context isn't there.

And it actually was the highlight of my week this week because on Monday I came in to like an unbelievable loom providing context in providing the milestones around the project. And I talked to, you know, the cross-functional stakeholders this person was working with, and they were like, oh, yeah, yeah, I get it now.

That was super helpful. Like, I'm so glad this person did it. So that's an example of, of when I've done that, it just happened this week. 

Brett: It's interesting in those dynamics how often I think like the normal human reaction is this person is behaving in a way that I don't want them to behave or they won't do what I want them to do instead of what am I doing right?

How am I creating these conditions? And I think that gets at. If you are having an issue with some cross-functional project, maybe there's a lot more in your control. In this case, the what and the why context setting. Maybe that's the reason that the thing's not getting done. Maybe it's not that Sally doesn't like you or this person's a jerk or they're too busy on their other things.

I, I think we all have a lot more agency than maybe at times we would imagine.

Anique: I actually think this person believes, like has a lot of agency. I don't think it was that. I think sometimes it's your perception could be a bit off. I mean, I don't know how many times I think I clearly articulated something and I did not like they were like, the trade off is not clear.

Like you made no decision, right? And you're like, oh man. And so I think having like real partners at work, like whether it's your manager or people you work with to give you that this is how it's landing. Let's go try again. Is really important because I actually, I do think most people see agency and they feel like they are working within their agency.

It's more of a gap in perception. That's my hot take. 

Brett: I wanted to loop back to a couple, maybe more brief topics that you touched on a little bit. But one is, are there any interview questions across the different roles you've hired for that you really like and maybe what's the story behind those? 

Anique: The two questions that I always ask, no matter the role is like the biggest accomplishments, biggest failure.

And like what was your actual role and what was your learning and what was your positive learnings and what were your like, I need to grow. And then the other one that I like to ask, and this is you know specifically with product managers, is how would your engineers describe you? How would your designers describe you?

And specifically like what's the thing they really want you to improve on? And I think that it gives you a sense of awareness, and I think that's in any leadership role.

Brett: How do you avoid the kind of pre-canned, you know, I try too hard or they're like rehearsed on their one big failure and all they learn from it and how the phoenix sort of rose from the ashes or whatever.

Anique: I generally, if I feel like I'm getting that answer, I normally course correct it and I normally say, no, no, no, no. I really wanna know. What's the thing that you do that annoys your like cross-functional stakeholder? Because there's something about the word annoyance or disappoints that's emotional. Like you can't give a polished answer to it.

Like no one has like a cute annoyance answer or like a phoenix rising from the ashes answer to that. It has to be raw because I'm asking for an informal answer and so that's, that's generally how I cut through. 

Brett: What are the misconceptions people have about you is pretty interesting. That's very related to that.

I find people struggle to instantly not tell the truth. When you ask someone what's like the misconception that people have at work about you or your team member, that there's like interesting fodder that comes of that. I'm not exactly sure why that specific one leads to interesting places. 

Anique: I think you're just not expecting that question

Brett: and it's very easy to have an instantaneous answer.

Because people implicitly or explicitly, I think, have thought about misconceptions about them. And so it's easy to sort of share. 

Anique: Yeah, it's a subconscious response. I think that's what I try to get to when I'm like, what would someone say is like really annoying or frustrating about working with you? I'm looking for the subconscious 'cause everyone's gotten that feedback that stings.

And you remember it and it's, it's probably connected to that misconception. 

Brett: You just briefly mentioned this, but anything you do in reference checks that sort of gets to the essence of someone 

Anique: In the reference checks I go through the standard questions, the background, strengths, weaknesses. I think the three questions that I really try to spend time with is at the top of the reference check or back channel.

It's tell me about your working relationship with this person. 'cause I wanna understand how long did you work with this person? Were they a peer, were you their manager? Were you a direct report, et cetera? Because I think it's the context for all of the other insight. And so I really wanna understand the length of time.

And there's some early indicators, right? If someone only worked with you for three months, That's an indicator to me that that's actually not a great reference. And so it's like the first flag in the conversation. And then the second two questions that I generally spend time on is, would you rehire this person?

Would you rehire this person for almost any role? Because I think there are certain people that you truly would, would rehire. And in both of those questions, I'm really listening for how enthusiastic or passionate they are. I mean, there are some people on my team that I'm like, I would be dying to give a reference for you.

I cannot wait for the day that I get to give a reference for you, and I get to talk about how amazing you are for 30 minutes. And I give those types of references. Right? Or there are many, many caveats. This is the first thing that person do is they caveat. Well, it really would depend what the role is. I mean, it'd have to be this very.

Specific thing to me that's an indicator that this person may not be as flexible or as much of a generalist that, that we may need right now. And then the second question that I always ask is, where would you rank this person in the top percent of people you've worked with? Top 1%, top 5%, top 10%, top 15, top 20.

But I generally find it's a forcing function for honesty because it's a binary question, right? And it's, it's harder to skirt around. And to your point on misconception, it's a gut question. And I do generally believe that people by default wanna be honest. And I think it's a very clarifying way to end the reference check.

Brett: What percentage of the time when you're referencing a candidate, do you get that level of enthusiasm in that question? 

Anique: That level of enthusiasm that I just showed, probably like less than 25%, but some level of enthusiasm and positivity and excitement. Probably closer to 50. 

Brett: Is your bar that 25% or you think for a lot of roles, 50% that amorphous, whatever the 50% is?

Yes, I would hire them again, but it's not, this is the most incredible person I would kill. To work with them again is perfectly fine for most roles. 

Anique: I definitely think you wanna be hiring people that are like, ideally top 5%, top 1%, top 10%, right? 'cause these are references, someone is giving you. But I also think the reference is anchored by how many people they have also hired for as well.

And so do I think that there's like a grave difference between the top 1% and top 5% of a reference? I don't because I think it's anchored in in the references hiring, but for someone giving you a reference, You definitely want the person you're hiring to be in the top 10% of talent that that reference has worked with.

And on the strongly rehire, they don't need to be effusive like I am right now, but they do need to say with strong confidence that they would rehire them. 

Brett: Have you noticed there's a discernible difference between references that the candidate gave you and you doing your own backdoor references? 

Anique: I think for the right candidate, no.

I really do think that, I think there are certain people that have a very consistent reputation. Whether you're like informally asking or formally asking for a reference, you have all sorts of social proof of that. You'll say someone's on your team at a, you know, at a dinner or a networking event, and someone's face will be like, oh, I worked with them.

They were amazing. And that that reputation is very consistent. I think there are times in a back channel versus a reference. That the back channel may be more detailed on that person's area of growth. And we all have areas of growth, right? Even your, your high performance have areas of growth. Like we're all a consistent work in progress, but the overall sentiment I think is generally pretty consistent.

Brett: The last couple things I was hoping to chat about were some of the ways that you. Run your org and your team and spend your time, and one that sort of comes to mind is now that you're in this role of COO, what does a given month look like? And are there specific rituals or way that you spend your time that you found particularly impactful?

Anique: I think we touched on this a little bit earlier, but my like 30 day clip is pretty consistent, right? So I begin my week on Mondays, essentially with a staff meeting. Generally going over what are the key customer moments of the next 90 days, what is the health across these launches or big rocks. And then at the end of the month, I basically have a template that's tied to the company plan that is asynchronously updated, and then I'll create a short loom over it.

And so it's like a forced moment of reflection. 

Brett: What are the other key touch points that happen every month for you? 

Anique: Every morning I check our data. I have a terrible habit at Slack. Slack bots are, you know, my best friend info. But I start my morning looking at the daily dashboard on, on how our self-service business did the day before, but I do actually find that really anchoring 'cause it starts my day on, on kind of progress to goals. 

Brett: Do you find that if the data looks really good, your morning starts out better? 

Anique: Yes. 'cause I'm a human. Absolutely. It's why I ask the question in one-on-ones, like, what's your energy level?

What's the perception on execution? Because. I believe that every person you're hiring in a startup, every like leader on your team wants to be excelling. Extraordinarily rarely is someone crushing, having like both the inputs and the outputs that they wanna be seeing and have an energy on red. That is very rare unless there's something extraordinary going on in a person's life.

And so yes, when I look at the data and we're having a good day, am I in a better mood? Absolutely. 

Brett: Do you find that there are people, regardless of how things are going, that are always green? 

Anique: That's actually, that's a great question. I don't think anyone is always green. And if they are, then they're not being truthful with themselves or you. 

Brett: Even if they meditate a lot?

Anique: I mean, I meditate a lot and I just told you I spend my, I start my morning looking at our self-serve numbers. 

Brett: You need to be more detached from the metrics. You can watch them go by like a thought. 

Anique: Yeah, a lot of noticing. A big fan of noticing. 

Brett: I'm noticing the numbers to not look good yesterday. 

Anique: What I would say is I think there's a group of.

People that when things are hard, they're actually green. The numbers just hitting. They can go either way. It's the challenge or like the novelty that really lights them up and it's the digging deep and I think that actually is a unique person. 

Brett: Are there other sort of parts of your week or month that you find useful?

Anique: I think those are the big ones. It's like the Monday staff meeting for me, it's how the one-on-ones are connected to the company plans and templates. It makes sure you're spending the time and the discussion time and the synchronous time in the right place. I think the end of month reflection is just healthy.

Otherwise, the 30 days become 60 days. And then in addition to the executive meeting, we also have a go to market meeting where we review the pipeline and how that's going in key projects that we're working on to support our sales of business, and those are really the rituals that I lean into. 

Brett: Something we haven't talked about is the relationship that you have with your CEO and how you sort of structured that. and I'd be interested particularly in hearing it from you, given there's a lot of areas that I think that you own in the context of a COO that is not sort of like normal in in a PLG or or B to B company, given that you have so much ownership over design and product and that tends to be something A CEO owns and then gives a lot of the go-to-market finance ops over to COO.

So I'm curious kind of what that working dynamic looks like. 

Anique: Yeah, I mean it's something that's definitely evolving that we check in on and, but we do have swim lanes in order to make us both successful. But Joe is, has unbelievable taste and has like incredible instincts on user experience in the brand experience of Loom and the product strategy.

And so I am still very much his partner in that. You know, he gives direct feedback on designs and product direction and product strategy. The way that we think about my role is, you know, at a PLG business, marketing, product design data, are so interdependent. And so bringing them together creates a lot of efficiency and focus for the cross-functional team rather than everything being so functional.

Brett: What was the configuration before you took on the role? 

Anique: Before I took on the role, I would say it was a much more like traditional, like these are the seven functions you have and we're all working in parallel. And now I think that we are working in a model that's much more cross-functional by nature and in in that way more flexible.

Brett: And what does that end up looking like? 

Anique: The traditional org structure is you right, you have product, you have engineering, you have design, you have people, you have finance. You have sales, you have marketing, right? And every single one of those functions is, is reporting into the CEO. And I think what we've actually said is like, actually, if we carve out the functions that are working the most closely together, engineering is, you know, led by our CTO and co-founder Vene.

Product marketing, design operations data actually is 9 out of 10 times working on the exact same body of work. Can we make those priorities across those various functions absolutely clear, and can we build supporting rituals? That enable us to work better cross-functionally. 

Brett: Is there anything outside of the engineering that doesn't sit in your direct org now?

Anique: The people team, the finance team, and then customer success and sales.

Brett: I, I wanted to end in an area that I, that I always like to, which is when either you think about your current role or your product career thus far, who are the folks that have an outsized impact on you, and what kind of tangible or specific thing did they impart that's kind of a part of the way that you think about building companies and products now?

Anique: That's a great question and there's different phases of it. So I'll start from the beginning. Kind of the roots. So I would say for my time at Teach for America, it was some of the best feedback that I ever got was know when you're communicating for yourself versus you're communicating for others because there is a difference.

And when you no longer know, that's a sign you should take a beat. Like you should, you should reground yourself. And so really thinking about the audience, and it's fine that sometimes you need to communicate for yourself. That's fine, but you should always know whether it's for yourself or it's for the person you're coaching or the person sitting across from you.

And I found it such simple feedback that it always stays with me. And even when I feel like I did something well or didn't do something well in terms of communication or coaching, it's, it's something I come back to. Ariel at TripActions are now, Navan is a force of nature. There's so many things I learned from him, but I think a, a few of my favorite are if you're at a startup, And you're posting quarters, like this'll be done in Q two, this'll be done in Q three.

You are deeply confused about your job. And it's, again, it's so simple and he's so right. That's not the right mindset. We are confused, right? If you start getting more specific, if you start getting hungrier, you get down to a date and that date may move because you have more information, but at least it, it's an indication of, of hunger to deliver.

And again, it's really simple, but I think it's. It's very true, and I still do it to this day. If I get something with a bunch of, it'll be done by the end of the quarter and I'm like, who knows? What'll happen at the end of the, I don't. I mean, 90 days, what of the day do I pick? I mean, it is true. 

Brett: What are some of the other isms?

That one was very good. 

Anique: Oh, he has so many isms. They're good. Another one of the isms, which is absolutely true. While there is value in AB testing, if you're only AB testing, it's inherently incremental, and that should be an indicator that you're not taking enough bets even before you get to a product review, if you look at what's on the docket for the next 60, 90 days, that's a majority of what you see.

That's an indicator that, that you're not being ambitious enough of what you wanna deliver or what your view of what's ahead is. Another one of my favorites is sometimes the most strategic thing to do is the thing that will kill you first. And I think what that really means is don't get so lost in being strategic that you, you forget about the task at hand.

You forget about the customer at hand. You forget about the salesperson you're working with who isn't able to like hit quota because they need X, Y, Z from the product, or they need some type of support. And so ensuring that you are absolutely taking a a midterm view, but excellent execution is what makes successful companies.

I think that's really what he meant when he used to jokingly say that to me and it was extremely clarifying. I'll ask myself that from time to time, and I think with Joe, Joe centers around simplicity and delight, and he will always go back to that. It's extremely grounding in the sense of when we're looking at a design, when we're looking at an experience, even when we're looking at communication, is it simple?

That's the first bar you need to clear. And then the next one is, is it delightful? If I think about times where, where something we've shipped has really landed, it always goes back to it's the intersection of utility and magic, and I think that's just a different way of leveraging kind of Joe's core beliefs on user experience, which is around simplicity and delight.

Brett: Good place to end. Thank you so much for spending this time.