How To Deliver Feedback with Compassion and Clarity

Thank you, Harry. I’m super excited to be here.

I think one of the biggest things for me is when I was starting out as a founder, I scoured podcasts and articles, reading stories about moments and kind of now being on the other side of it a little bit, I’ve realized that moments aren’t really a moment. And for me, I think there were really three ingredients to my moment in building Cooley’s that happened over the course of probably years. So the first one was after a stint at a late stage startup in San Francisco, I moved back to Seattle, didn’t know what I was supposed to be doing.

Cold messaged someone on LinkedIn. His name was David Rosenthal. He’s now the co-host of a popular tech podcast called Acquired, but at the time he was a principal investor at Madrona Venture Group. So one thing led to another and I ended up as an early stage investor, which was something I never planned for. And I think one of the great aspects of early stage investing, and I was bad at many other parts of it. So I have deep admiration for investors, is that you could really take time to dive deep into any topic that you thought was interesting.

And so I took a lot of time to learn about open source and open core in the developer space, really just like inspired by kind of the stories of open and collaborative software development, the models that were pioneered by companies like Red Hat and Zensource and Cloudera and Hortonworks. And you see all these amazing companies today doing the same like MongoDB and Databricks and Starburst and Confluence. And so I think first off, it opened my mind to a completely new way of not only building software, but kind of distributing software.

Secondarily, through all of that work that I was doing in the developer enablement, developer tooling and open source space, AWS reached out and they had an opening for someone to help lead product marketing for serverless computing, which was a big strategic, innovative new area for AWS, as well as ultimately open source. It really mapped to what I was thinking about at Madrona. So I wanted to kind of get that hands on the ground experience. And when I got to AWS, I saw experientially the way that developers adopted serverless computing was not through this notion of kind of enterprise direct selling, right?

It wasn’t about a salesperson reaching out to a central decision maker who then would decide to adopt serverless and kind of put it down to all of the practitioners and developers. It was about developers learning and enabling themselves to learn how to use serverless, sharing knowledge and best practices with each other, deciding that it was the right tool that they wanted to use for their next mobile app, then going to their manager the next day at work and saying, I to build the next mobile app on serverless.

So it was a very much developer led bottoms up adoption motion. And so the team I was on, we set out to build developer community. and this was around 2017 when we really started building all of the developer community engagement programs that AWS still has today, including our developer Slack, our Reddit engagement, our Stack Overflow engagement, open sourcing product roadmaps on GitHub. And through building all of those programs out, I saw not only how positive of a reception developers had with AWS starting to do these things.

I mean, it was incredible that developers weren’t coming to these communities only to ask product questions and get their questions answered and leave. They were sticking around, sharing knowledge, helping each other out, creating content, really living and breathing that community first ethos. And so we saw that our developers, our customers really loved this type of engagement. It was authentic, it was personal, it was transparent. But we also saw internally how marketing teams, product teams, all sorts of teams that previously did not have that sort of direct access to the people that use the software they built. were able to now, through these community programs, engage directly and develop a huge amount of developer and customer empathy.

And I think those things combined just made me realize that this new model of kind of sharing knowledge and product development really felt like it was the future.

I think one of the biggest learnings I had from Amazon was the way in which an organization can align around a set of core values. Well, calls them leadership principles to really permeate every aspect of the company’s culture and decision making. So at Amazon, you’re exposed to the leadership principles from the first second that you interview for the job, because the entire interview process is based around those 10 core principles. to every single decision you ultimately make, big and small, as well as like the day to day comportment of every employee. like everyone wants to live and breathe the values.

And so when I left Amazon, I wanted to bring that learning with me to whatever I started next. And I had a series of conversations with someone who I consider a dear mentor of mine, who’s David Richardson, the VP of serverless at AWS. And he’s a long-time Amazonian. He invented many of the core services at AWS that people know and love today. And one of the things that he told me that was so eye opening is he was like, I always saw Amazon’s values as a way, a framework for disagreement.

It enables employees to lean on the values to advocate for what they think is right, even when it is counter to what their leadership may think. And I never thought about values as being a mechanism to kind of level the playing field between an employee and a C level exec, right? You never think about values as giving a voice to an organization that otherwise may not be able to compete on authority or intellectual knowledge or experience. So to me, that was when I realized that values need to exist from the very beginning.

Because if you’re building an organization, you want your organization to have a voice and you want to surface and provide a framework for conversation and debate. I think that’s one of the most important things that you could possibly do for your company, not only from a cultural perspective, but in terms of making sure that we’re making the right decisions.

Yeah. So I think there’s two pieces to this. The first is people need to know what the values are. right? So it needs to start from the second that someone interviews at the company. So we do a core values based interview where we send the candidate our values and we say, we’re going to ask you questions as part of this interview process that map directly to figuring out whether or not you have these values, whether or not you share these values with us. The second piece of it is, I think, just making decisions and making the values part of your everyday lexicon, right?

So when we have a difficult decision to make that has trade offs, we speak in the language of our values and we say, well, we have a core value around strive for simplicity. So this conversation is starting to overcomplicate the problem. Let’s strip it all down and think about the most simple solution. Or we have a value around craft excellence. So what does that really mean? It’s up for interpretation. And I think great values are meant to be interpreted. But crafting excellence can mean different things at different times.

And for us right now, it’s around launching amazing product features quickly and at a very high bar of quality, including stability and reliability. And so that’s kind of how we define it today, but it can be fluid over time. And then I think the third part of it is like, you have to be willing to change your values. So right now we’re actually thinking about changing two of them because we don’t use them very much in our day to day life. We don’t allude to them very much.

We allude to other things more. And so when that happens, you have to ask yourself, should I swap out one of these values, which sounds really great on paper for one that in practice we talk about all the time. And so I think values need to be living and breathing. They’re not something that you decide on day one and set in stone. I guess, you know, if I were a Supreme Court judge, I’d be a loose constructionist.

Yeah. So you can get into some wordsmithing here, but I think it’s about a core fundamental point that you can all, as a team and as leadership align on as being like a primitive. So strive for simplicity. I think that there’s a huge urge for really smart driven people to oftentimes overcomplicate a problem. It’s easier to kind of start going down the path of how is this problem so complex versus taking a step back and thinking, why can the answer be so simple? And so for that value, it’s generic, but we use it very specifically, right?

We use it in situations where we feel like we’re overcomplicating a problem, where five people are in a room, we’ve talked for an hour about something, no decision has been made and why. If you take a step back, it’s really not that hard to make a decision. It may not be the right one. It might not be the best one, but it’s really not that hard to make one. And so I think that value is really about, like, can we strip out all the intellectual sort of massaging that we do day to day about all the complexities in the world and just focus on making it simple?

Yes. So naturally, by my personality, I’m transparent and direct person. And I think that transparency and directness are often poised as an antithetical to like empathy or compassion, which my investor and advisor, Jeff Weiner, defines as being empathy plus action. But I think that they’re actually two parts of the same whole in that one of the most compassionate things you can do in life or in work is to speak the truth and to speak it transparently. Even when it’s as difficult as letting someone go. one of the most compassionate things you can do is let someone go who’s not going to succeed in the current role that they’re in.

But I think that while speaking directly and transparently is the what, being compassionate is the how. And that’s something that’s incredibly difficult, much harder than simply speaking directly. It’s something that I work on every day. I mean, I’ll give you a tangible example. Like last week on the team, some stuff slipped and I spoke very directly to one of my awesome teammates. and I wasn’t wrong, but I definitely spoke in an intense and direct way. And so in that moment, I failed on compassion. And so, you know, I think they’re two parts of the same whole, but in practice, they can often be at odds.

And yeah, it’s tough, but you can’t have the what without the how, right? At the end of the day, it’s how we do things that really matters.

Yeah, I’m still working on that myself. But one of the things that I’m not a huge fan of is the shit sandwich, which is this notion that you want say something nice and then, you know, give a direct piece of feedback and then say something nice again. That’s not really how I want to communicate. And so we kind of have this rule on the team that like, we’re not going to give feedback as a shit sandwich. We’re just going give feedback directly and transparently and honestly, You know, we’ll celebrate our wins as a team and we’ll celebrate the things that we mess up on as a team.

So that’s kind of how I think about it. I don’t think it’s antithetical to compassion. In fact, to me, it’s just a more efficient way of communicating.

Yeah, so it’s definitely not a perpetual plan. It is our near term plan and our plan so far. So probably until the end of this year, we’ll be looking to bring on board folks who are experienced. And we did this because I think a couple reasons. The first is we are very much a COVID era startup. We closed our seed round the Friday before the markets tanked. I think it was like Black Monday or something. We’ve been remote this whole time, even though the majority of us are in Seattle.

And we had a choice between hiring senior people or hiring a diverse set of skill sets, which were at risk of not being successful because of the nature of us needing to move very, very, quickly, and also us not being able to ever be in the same room. Right. Because when you are starting out your career, so much of what you learn is through osmosis. I think of the most critical moments in my early career were just being there like a fly on the wall when my VP of finance was having a conversation with the CFO at the desk next to me.

And we realized early on that that just wasn’t going to be possible because of COVID. And so we did not want to put a super ambitious person who’s just starting out their career into an isolated room and put the onus of reaching out to folks on the team and getting help on them. I think the second piece of it is there’s this myth around startups that you need to be a college dropout or you’re this kind of natural born savant and you’re just a team of incredible 20 year olds who have a dream.

In reality, I think it’s more about can you solve customer problems? Can you build amazing software? Can you provide educational marketing? Can you go to market in a way that is good for your customers, but also good for your business? And to me, all of those things come from having some level of experience because you’ve seen things that have worked, you’ve seen things that haven’t. A lot of the folks on our team, they’ll say to me, I’ve done a couple of startups, I have so many regrets from them.

I’ve seen the ways in which I’ve messed up or the company has messed up or things that we could improve upon. And I to do that again at CommonRoom. I want to fix the things that I didn’t do well the last time. And to me, that’s awesome because that means that they’re carrying with them a set of stories that can help us be better.

Yeah. So maybe this gets to how my co co-founders and I got together. So similar to how I got my job at Madrona by reaching out cold on LinkedIn, I met my co founders on Tinder for Enterprise on LinkedIn. Francis and Viraj were both just cold messages that I reached out because I saw their profile and thought they had superpowers that I didn’t have and a really interesting background. And the long poach story here is that I reached out to Francis and Viraj on LinkedIn and they ignored me.

I didn’t hear back from them at all. It wasn’t out of malice. Francis and his wife Lisa had just had their first kid and he had just left Facebook to be a full time dad. And Viraj was kind of in the throes of a very busy and important job as the technical advisor to the CEO of the last company he was at. And they didn’t respond. And so a couple of weeks or months passed, and I continued to kind of make progress on my own, talking to customers, doing tons of customer discovery.

And when I felt like I had a new level of insight or I had reached kind of a plateau in terms of progress, I reached back out to them and I would update them, right? I would say, hey, would love to catch up again. Here’s all the things that I’ve learned since the last time I messaged you, not knowing at all if they were even seeing my message. And I think persistence here pays off over time, but also showing that continual progress where ultimately they did pick up my call.

And with Francis, it was organic and it happened fairly quickly where we were just like, let’s do this. With Viraj, even after I got on the first call with him, he was pretty skeptical. He was intrigued for sure. And so it took actually a couple more months of me doing the same thing, reaching back out, updating him on our progress where, you know, he finally felt the sort of seriousness of what I was saying, right. which is that I wanted him to be my co-founder.

This of goes way back. I’m an immigrant. I moved to America from China when I was five. I’m an only child. I grew up with pretty much my two parents hardworking, and I think they taught me the value of persistence. And as a result of my persistence and my kind of determination to achieve my goals, I’ve gotten the reps in. I’ve seen how being persistent and not giving up has led me to achieve things that I didn’t think were possible, including changing careers, going to a school I never thought I’d get into.

It’s almost like sports, right? You practice and then you lose, you practice and one day you win. And now you know that hard work and practice leads to sometimes winning outcomes. And so when you lose, you’re okay with that because you know that all you have to do is practice more. So to me, persistence is as much about that kind of mentality of practice where I could get a hundred no’s and I’m good because I know that I learned from each and every one of them.

And those a 100 no’s are going to get me to the yes. So I don’t have a scarcity concept here. The world is large and to me, I optimize for learning along the way, which means that you will fail. Like, there is no winning without losing.

is something I’m definitely still working on, but I also realized that one of the biggest parts about growing as a human is realizing what you’re good at and what you’re not good at and being okay with the things that you’re not good at. They don’t make you less valuable. They don’t make you a worse person. I am horrible at administrative tasks and logistics and everything there. I’ve missed four flights in my life just because I got confused about the time. I’ve booked hotel rooms on the wrong dates.

I’ve lost my luggage multiple times. I make my own life very, very difficult. Now I realize that I’m bad at those things and I’m okay delegating. Like I just got a business administrator who’s going to be my executive assistant and I always hesitated to have an EA. Like it felt like to me, who am I? Who am I to think that I should have an EA? But now meeting the right person who loves to organize and handle a list of tasks with the utmost authority, I’m like, yes, you are who I’ve been looking for my whole life.

And that’s just one simple example of just being okay with the things that you’re not good at and leaning into the things that you are good at and knowing that that’s enough.

So I process data in this way where everything that I receive as inputs, file away. Like I organize them and I file them away into my brain bank. Maybe I take action on it at some point, but maybe I don’t. And they kind of just sit there latent. And so while it may seem like to my team that I am such a rational person who thought we were doing one thing and then when presented with a piece of data, I’m now like, okay, yes, that’s the path.

In reality, it’s because that new piece of data has been filed with all its little data friends into a file folder that has gotten so fat over time that it’s almost impossible for me to not ignore it. And now I know with confidence that this is the path. So that’s kind of how I process things. And I would say no decision I’ve ever made as potentially in the moment surprising as they have been, have been, surprises to me, if that makes sense.

So Danny and I are, I think are a lot alike in this respect where frankly, I think I’m an incredibly rational person, but I’m also very feelings and intuitive driven person. And for a long time, I didn’t understand how I could be both. And I think people close to me couldn’t understand it either, and they thought I was odd. But now I’ve come to the conclusion that they’re very symbiotic. When you get presented with a hard piece of data, like a candidate’s perfect resume on paper, that’s a piece of data that goes directly to your head.

You’re saying, hey, I process this data. I know it to be presented to me as truth. But intuition is this interesting thing where I think that it takes into account that hard data, but also like a multitude of subconscious informations and channels aggregated over years and your entire existence. And it’s also like the most base of human survival mechanisms. Right? It’s what made early humans wake up in the middle of the night and get the heck out of dodge, even though they don’t actually see a predator around.

And so to me, intuition is the summation of that hard logical reason, plus a lot of subconscious things that you may not really fully understand in the moment. The example with the candidate that I’ll give is someone who looks amazing and perfect on paper, but then when you talk to them, there’s a whiff of ego or there’s just something that’s not quite right about how they’re speaking about their experience. And there, I’m always going to go with my intuition because it’s already taken into account the hard data. right?

It’s kind of the whole.

I think that it comes down to our relentless focus on the customer pain point that we’re looking to solve and spending almost 100% of our time and resources on that. You may not know this, but we didn’t have a website. We hadn’t updated our LinkedIns. We had done zero marketing up until we announced our Series B. And it’s not because we were sitting there not doing anything. We existed, but we were having very focused relationship building conversations with innovative organizations and companies that wanted to seek a better world for what community engagement looked like at their companies.

And so by doing that, what we ended up doing was we ended up, I think, building a better product faster that our customers could get hands on quickly and start seeing real value out of CommonRoom. So building features is one thing. Getting value out of a piece of software is a completely different thing. And we focused on that maniacally. So I think with respect to funding, we just wanted to, first of all, both of our rounds have been opportunistic and we’re working with investors who had a deep, deep, experience and thesis in the space.

So it was very, very, easy to kind of say yes to the dress. But secondarily, we have some incredible customers that we’re working with today who are going to be running their kind of community critical operations on top of CommonRoom, And we simply wanted to make sure that we were well resourced to provide them the best service and also build the best product that we can.

Yeah. So this is the tough part, right? everyone knows writing surveys are really, really, hard because you have to kind of wordsmith and get it just right. I don’t index on that piece of it at all. I focus on two main things. Who is my customer? Like as a person, what do they want for their team and their work? And then secondarily, like what are their pain points and what’s getting in the way of the things that they want do. And I think when you focus on those two things, then you’re asking about problems.

You’re not asking your customers to give feature requests. You’re not asking them to propose solutions because that’s our job. We to listen to the problems and then we need to go and innovate on behalf of our customers to figure out and propose a plausible solution. Sometimes that can look like product features, and sometimes it can look like sharing knowledge across a set of organizations that all have the same question, right? It can look like a lot of different things, but we never ask our customers for features.

We ask them to tell us their problems, and that’s how we always start.

Oh man, this is hard. I was a literature major, so I feel an allergy reaction when I’m asked what my favorite book is because a couple of different things here. The first is I have way too many favorite books and I don’t always have reasons for why I like them. Because books are such like, your love of a book is also a function of like who you were when you read it and all this stuff. But secondly, I hate reading books now. I don’t really read because for most of my childhood and all through college and even beyond, I read like five books a week.

And I’m it’s just a place I don’t actually want to return to all that often.

have a weird relationship with books. I probably need a therapist to of help me work it out.

Okay. I don’t think people are gonna like this answer, but I genuinely don’t think for what we’re trying to do, any company at all is I really see our competition as inertia, as the way that companies are already doing things, as human nature. That’s a terrible answer, but that’s what we’re up against. We’re up against organizational change. We’re up against challenging companies to think about servicing their customers, building their product innovation in a totally different way, which is around being community first. And that to me is the competition.

And if there’s other companies in the space who share this same mission with us, then I don’t necessarily think of them as our competitors. I think of them as, I guess, frenemies. Okay, don’t say that. That’s how I think about succeed, then this was a big enough market and a big enough need where we can all exist. I think it’s far too early for me to be worried about any competitor, large or small, so I just don’t spend too much time thinking about it.

I think the first angel was Dylan Field at Figma. It came about because he obviously is the co- founder and CEO of Figma, which is one of the greatest community first product led growth stories of recent years. And he has such a conviction and passion around building community as not only like a way to enable adoption of Figma, but also to provide a platform on which people in developing countries or people who are just starting their career can build a set of expertise and skills that will enable them to take it with them in their career.

And so I think he was really passionate about the space and he had investing in sort of adjacent companies that may not have necessarily worked out. And he thought that we could be one of the companies that could kind of take it further. And so I think Dylan was our first angel.

Well, he’s younger than me, so you’re winning on this one.

I don’t like bananas because of the way that they sound when they’re being chewed. And I don’t like who I am in that situation because I hate the person who’s doing the chewing. and I don’t like that. On cheese, you know, when I first moved to America, I thought it was really weird to have dairy on your meat and dairy on your raw leafed vegetables and dairy all over the place, and dairy on your cake. Like the way it was used was very, very, controversial controversial for me.

I used to pick like cheese off of my pizza, which, you know, I don’t do anymore, but I’ve now accepted cheese. I’ve come to a new, I don’t know, acceptance that cheese is like a big thing.

The most challenging element is the space between the greatness that I know that we can achieve the work that it’s gonna take to get there, both from a team perspective, but also from like a personal perspective. I have to transition and learn how to go from, someone who was an only child who always got straight A’s and like did everything on my own to someone who can teach and coach and inspire and lead. And it’s a tough transition. I probably need a therapist. Maybe I’ll get one after this conversation.

But I think it requires like everyone on the team to like dig deep and kind of learn more about themselves and challenge themselves to like reach something that they may not have ever reached before. But also like we need to grow quickly. Like we are more than doubling our team this year. And so how can we do all of that while still growing and like never dropping the ball on our customers? I think above like all else, the trust of our customers is the most important thing.

I meditate, so I just started doing it. It’s really nice to kind of quiet the racing thoughts that are in your head, right? Like if you’ve ever woken up at 3am with racing thoughts and you think you’re being brilliant, but none of those ideas are ever good. That’s something that I’m definitely trying to improve upon. And then also being present and just appreciating, like, so one of the things I like to say is the horrible situations of today will be the kind of happy hour stories of tomorrow.

So even when things are going terribly, like enjoy it because it’s such a privilege and honor to be able to do this thing. And I look forward to, you know, one day when we’re all laughing about something that made us cry a year ago.

I think in the next five years, we’d love to inspire, encourage, challenge more organizations, not just the amazing ones today that we work with and who are already bought into kind of this community first ethos to become more community driven, to think about how they can organize their customer facing interactions to be authentic and build relationships with people, not accounts, to view their practitioners as their biggest advocates and their biggest evangelists and the ones that need to be enabled.

And if we can do that and service, the amazing companies that are doing that already today and struggling to do so with existing tooling, but also expand and help other companies think that way that aren’t doing that today, I think that would be success for us.

I’m glad I threw away whatever I wrote.