← Second in Command: The Chief Behind the Chief with Cameron Herold
Second in Command: The Chief Behind the Chief with Cameron Herold
Ep. 564 - Asana COO Anne Raimondi - How to Conquer Imposter Syndrome and Lead Powerfully
00:49:29
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- [00:00]
A
Just a quick note before we dive in. This is actually one of our older episodes, but we're bringing it back because it's one of the most downloaded ones we've ever released. Clearly it struck a chord with a lot of listeners and I know there's so much value packed inside. So whether you're hearing it for the first time or revisiting it, enjoy this fan favorite.
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B
I do think it starts with that which is like what does great look like and what does excellence mean for that company at that stage with that board? And and then where are the gaps today from even just like board meeting and time spent standpoint, the friction points or the like. Gosh, we're not getting as much out of often is because that hasn't been clearly defined or redefined. Right? Which is like the precious time we all spend together and the time that the management team spends preparing for these meetings. What does a good outcome look like, you know, and what does the company need over this next arc of its journey? Welcome to the Second in Command podcast produced by the COO alliance and brought to you by its founder, Cameron Herold. In the second in command podcast, we talk to top COOs who share the insights, strategies and tactics that made him the Chief behind the Chief. And now, here's your host, Cameron Herold.
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A
Our guest today is Asana's COO and Head of Business, Ann Ramundi. Ann first joined Asana's board of directors in 2019 and is an industry veteran with over 20 years of experience leading various product and business functions in fast growing SaaS companies. Prior to her role at Asana, she was the Chief Customer Officer at Guru, Senior Vice President of Operations at Zendesk, Chief revenue officer at TaskRabbit, and held senior positions with SurveyMonkey and eBay, with a strong commitment to fostering innovation in the technology sector. Ramundi is also a Lecturer in Management at Stanford Graduate School of Business and and she served on the Board of Directors for Gusto, Patreon, Guru, Sendgrid Block and Thredup. Ann holds a BA in Economics and Sociology and an MBA from Stanford University. Ann, you are a classic underachiever.
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B
I'm going to invite you to introduce me to my children.
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A
That's a crazy bio. You really got some experience behind you. I'm not even entirely sure where to start with this. What do you think got you to where you are today?
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B
That's such a good and big question. I would say if I trace it all the way back, it's actually just a willingness to stay Curious and keep learning. I started out my career as a management consultant and just, just discovered that I actually really like business problems, but also business and people and team challenges. And so found my way to becoming a product manager. And I would say I credit a lot of the rest of my career path to that early product training of customer discovery and development. Like what's asking the five whys, what's actually at the root of it? And how do you create many possible solutions to solve a problem? I would also say timing. I was really fortunate to enter the workforce at a time during the dot com boom and all these businesses were being built really for the first time with the growth of the Internet, really saw the possibility of startups and scale ups. So those two things I would credit for then creating lots of doors that opened.
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A
Okay, so I'm going to date myself, then I'm going to travel back in time with you to kind of March of 2000 when Steve Ballmer stood up and said there was an Internet bubble and we're all like, oh shit, don't tell on us. And the whole stock market collapsed. The Nasdaq crashed by 78%. Why would you stay in that space? Why did you stay in that sector? Because it was fun from kind of 97 to maybe 2000. But why did you stay?
- [04:12]
B
Yeah, and when he said that I was living in Seattle selling diamonds online,
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A
I was in Seattle too.
- [04:20]
B
So yeah, of all things. Right. So I would say why I stayed is, you know, chasing it back to being at a startup, Blue Nile. And then later what led me to join ebay was actually the customer pain point. There was, yes, there was a lot of froth in that era and lots of businesses, if you look back that, you know, are the original concepts are now huge businesses today. They're not in the same iteration as the dot com boom. But when we, when I looked back all the way to like, well, what kept me engaged was we were really reimagining how to solve, you know, customer pain points. So whether that was the friction in buying jewelry in traditional retail settings or then later at ebay, being able to reach other like minded collectors and fans across the world who had sort of these shared passions. And prior to a platform like ebay, they would have to, if they could travel, they would have to go to annual shows and meet one another. But if they had a local antiques business, they were really limited by the number of people that they could attract. And all of a sudden ebay opened up all these possibilities. So I think that combination of customer Pain point. And then just seeing real kind of entrepreneurial spirit just kept me really motivated of look, there'll be ups and downs in the technology industry, but this desire to create and improve life for other people is really motivating now.
- [05:57]
A
If.
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B
If.
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A
Okay, so I understand why you stayed and probably what got you to where you are. I was living in Seattle that same. The same time period. So I probably bumped into you at Belltown Billiards. And I, I was living at 2nd and Vine. My office was at 2nd and our first in Bell. Love that whole area.
- [06:17]
B
We were, we were neighbors because down there. And I lived on fifth in Queen Anne.
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A
So positive.
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B
We passed each other.
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A
Then we probably had the. Oh, at Teeny Teeny Bigs was where I was drinking my martinis right at the bottom of Queen Anne and getting Cosmo to deliver our Ben and Jerry's ice cream. Right?
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B
Yes. Or packs of gum if you just ran out of gum. They also delivered that.
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A
Yeah. With our dvd. All right, so you were very. Do you think the product focus, do you think that's critical for COOs to actually understand product and product development? It feels like it is.
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B
I do. Well, I'll caveat this being like my experience is within technology and different industries within technology. But I do think it is really important for CIOs to understand, I would say sort of the, you know, the fundamentals of like what you're putting out in the world. Right. And so within a technology organization, that's product and your customers and, you know, what are their pain points and what's the strategy around building that product? Again, there's different flavors of CEOs and we'll probably get into that. But certainly as a head of business that's responsible for go to market and how we meet our customers and how we serve them. And it intimately is related to then how is our product built? Why are we building it the way we are? And then how together do we deliver for our customers? My partnership with our R and D organization is extremely critical to our ability to grow the company.
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A
Now you're at a company right now that their brand is super strong, publicly traded company. Your career is kind of strong. What keeps you there versus being poached to go somewhere else.
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B
I really fundamentally love a couple of things here. One is the problem that we're solving. I sort of feel like this is the problem I'm meant to solve. I was. You mentioned me going to Stanford undergrad. I was an organizational behavior major as well as econ. And so from an early standpoint I just love the problem of like, how do you help humans work better together? And so that's very much the problem that we're solving at Asana. How do we reduce friction in teams of all sizes and just make sure people's talent and time is put towards the most important problems in the world and spending time there versus what we call like the work about work. And then the second is I really love the people I got to know, the leadership team and employees. And during my time as a board member and I just deeply believe, especially over the last almost two years, of what the world has gone through, who we spend our time matters so much. It changes us and it can change us for the better if we pick wisely. And so the problem that we're solving and the people I get to solve it with is why I get excited to wake up early every morning and come to work, you know.
- [09:16]
A
So when you were on the board at Asana, how big was the company back then? How many employees approximately?
- [09:22]
B
We were, let's see, when I first joined, we were probably about a third of the size of where we are now.
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A
Can you say how many employees?
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B
Yeah, I'm trying to remember the exact. We were probably around less than 300 employees.
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A
Okay. And you're bumping into the thousand mark now.
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B
Yeah.
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A
So it was. So was it a board of directors at the time or board of advisors?
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B
It was a board of directors I joined as the first independent director.
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A
You don't seem bored enough to be on boards. What was it that kept you intrigued as being a board member?
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B
You know, I actually had found over my career that sitting on boards made me a better operator. As an operator, you know, so much of my day to day can be reactive, especially in growth companies going through a lot of change. And I just really enjoyed the opportunity to be on board because the conversation at that level is strategic. It needs to be. And so I would go back to my day job asking better questions and tying my work better to the strategy of the company. And so I've been really, I was really, really motivated there of balancing that strategic view with my day to day operating role. And then now I've come to really see that boards done well in terms of thinking about governance, really have the opportunity to change the ARC not just for that company itself, but if they're seen as a leader in the space, things like DEI and pay equity boards are governing those decisions. And so I just feel like that's such an important opportunity to make an impact in more people's Lives if I pick wisely with boards and companies that really are kind of pioneering change.
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A
That's interesting. And listening to you too, I love that it actually deepens or richens your operational expertise as well. So you said something just around the product and I want to talk a little bit about Asana. I mean you pretty, if you're in business, you've heard of Asana, but can you explain to people, I guess, why Asana is different than some of the other project management tools or I guess tools that are in and around your space?
- [11:51]
B
Yeah, I think that our, our fundamental difference is how our founders, Dustin, our CEO and jr, who's a co founder and they met each other and worked together at Facebook and decided to solve this problem when they were at Facebook and built an internal system there which then motivated them to start Asana. And it was very much this architected from the beginning the concept of what we call the work graph. And so it's not just about task management or project management, but it's understanding all the elements of what comes together for teams, teamwork and in particular cross functional teamwork. So it's the who, what by when, why, all that context and that richness in our data architecture actually translates into real benefits for anybody who's using Asana. So to make it more concrete, so me coming in as a new leader, I've been here about three months now. I had gone through a lot of C level onboarding in my prior lives. You know, in high growth companies, bringing on other C level execs and onboarding a new exec is usually a heavy lift for the organization, the team. Right. There's special meetings, decks created, you know, ways to like update and you want to ramp a new leader, you want them to make an impact. The difference here at Asana, because we run Asana on Asana, is I did not have to have a special meeting or special content created for me to get up to speed on what was happening, decisions that had been made and probably most important for me, people context around all the incredible team members globally that I have the privilege of working with. I've been able to see their work, their contributions, their successes even before I meet them. And that's really the power of Asana. It's that contextual information around the work that gives people clarity.
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A
Okay, so you just dovetailed into a question that I was burning to ask you, which I'll ask now then. In 2005 or 2006, I was down at Microsoft's head office about 120 entrepreneurs or CEOs from around the world. I was there as a COO and we were being taught project management by the head of Microsoft Project. And after day one, partway into day two, he stopped and he said, but I need to tell you something interesting. Microsoft has banned the use of Microsoft Project inside of Microsoft. And we're like, wait, what? And he goes, yeah, we don't allow it to be used because it's too complicated and it slows everyone down so all we use is Excel. And I was, we were just like, what the F is wrong with your company that you build something you won't even use? And I always kind of wondered, and you said it, that Asana was built on Asana. Was that because Dustin was kind of entrepreneurial in a fast paced growth company and wasn't the big bureaucratic Microsoft that because you guys have crushed project.
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B
Yeah, I think there is. I would credit to this deep passion that Dustin and J.R. had for great user experience. So what you just shared of like the, you know, Microsoft banned Microsoft Project because it was too complicated. I think Dustin and J.R. really understood, hey, to do this well, people have to enjoy and want to use it, right? Because there are, you know, less, you know, less well designed alternatives that break at a certain point. But spreadsheets and docs and email, right? And but in order for us to truly realize the value of a product like Asana, people have to want to use it. They have to want to use it and see it as a great place to get their work done, to collaborate with colleagues. And so from the beginning, a simple user experience that's intuitive but then also fun. When you check off tasks in Asana or complete projects, a unicorn might come across your screen. And if you're like me, I've also turned on, there's a feature where you can turn on extra delights. And so, I mean, who turns down extra delights? Right? We need more of that in our life. So there's just lots of those moments of surprise and delight and also appreciating and celebrating your colleagues. I think that's the other thing that sort of built into Asana is when someone, you know, when someone, not just when they complete something, when they comment on something that you're doing, when they share something, you can thank them really easily and show that appreciation. And I think that builds stronger relationships too.
- [16:36]
A
Yeah, I think you've really listened to and built it for humans and then you also built it for Gen Y. But because you built it for Gen Y, the baby boomers love it. As well versus, you know, Microsoft Project and some of the old legacy project management systems were really built for, for engineers and product project managers and it never really bled into the rest of the organization. So you really are right in listening to the consumer. Can you talk about. So what I want to ask about Dustin really quickly, not so much about him as a human because I am very intrigued with Dustin Moshkowitz. But what did he see in you to bring you on as a coo?
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B
I feel strange asking, answering that question about myself in the third person. Maybe I'll flip it around and say when. When Chris Farinacci, our retiring COO shared his news after an incredible 30 plus year career, six amazing years at Asana, that he is headed towards a well, well deserved retirement. So when he and Dustin reached out and said, hey, you know the business, you know the team, what do you think about this opportunity? It was probably the only operating role that I at that time would just dive into and say 100% yes. I'm so excited given our stage and scale, the opportunities ahead. To come back to the question you answered, my hypothesis is some of it was just that we had had a chance to build a relationship over two and a half years and gotten to know one another. I had the privilege as the lead independent of sharing feedback from the board and having these conversations with Dustin after the board meetings. I feel like that that's my hypothesis on the reasons of just like we had a trusted relationship and you knew how much I cared about the team and the business as well as just how much I care about the problem that we're solving. Okay, so I'm gonna have to ask him that question.
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A
Yeah, I'm intrigued. Like I know you're the right hire.
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B
Sure.
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A
But I'm just curious as to what they see. How do you push back with that classic. Because he is classic entrepreneur. Right. I would imagine a little bit add kind of bipolar driving, 1,000 miles an hour idea to execution right now. How do you get to push back with him? Or is he like that?
- [19:04]
B
Yeah, I was just going to say actually Dustin's not. I would describe him differently. I think Dustin is incredibly intentional. He is absolutely a visionary founder and CEO or CEO. He's got a long term vision for the problem that we solve. I think that is rooted in just a deep understanding that how you help humans work well together in any size team and especially in larger organizations in solving some of the most complex problems is not an easy thing to do. Humans are inherently complicated and especially very smart humans with Lots of different ideas of how to solve problems. And so I think that long term view that Dustin has is incredibly motivating. And then he goes about decision making and empowering people in an incredibly intentional way. And so what I have found is maybe unlike the stories that we hear and even the experiences you and I have probably both had with other founders where there is almost this sort of frenetic nature of like there's just so many ideas and they're trying to get them out so quickly. I think Dustin actually is quite self aware and he does a really good job knowing how and when he should have an impact and knowing how to empower the people around him. And he, and he also is like that. Self awareness is also something that helps all of us get better. Right. He models a way to lead that I think is quite exceptional.
- [20:51]
A
I love that. All right, can you talk about when you're listening to the customers and you're so customer focused and customer centric, customers always have ways that they want us to build our product bigger and better. And for some of their own use cases, how do you know when to say no and how do you say no to them so that you don't build something that's maybe tangentially different from what you're supposed to be building?
- [21:16]
B
Yeah, I think that's, that's such a great question because I think there's, there are a lot of, you know, tropes in Silicon Valley in particular about like listening to the customer, not listening to customer. Does the customer know what they want, all those. I think my deep belief is the customers absolutely understand their pain point. They definitely know what doesn't work for them, what they're trying to solve, how they wish it could be solved better. And then our responsibility in building a product and a platform that we want to be accessible to as many customers of as many sizes as possible is to look for those underlying commonalities that then inform what we say yes to, and then what we say, hey, how about an alternative too, right? And stay creative because we ultimately do want to solve their problems, but they might come at it with a solution that in the end, when we unpack, is not actually the complete solution or doesn't solve the pain point as completely as we ultimately want to. For them and for many other customers and especially something like Asana, we believe that the more companies and more people are using it, the more rich examples we get that we can share across our customer base of the future of work management and that we're particularly excited about. So we do not see ourselves as creating something bespoke. We think the shared learnings across the incredible customers we have actually will accelerate our ability to. To have, you know, more people have more time towards their mission.
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A
I'm curious, this is a bit of a side question, but your background at Guru, which is kind of like the. One of the original outsourcing platforms. I remember back when it was, I think Guru. And was it Elance?
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B
It's a different. There are two gurus.
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A
Oh, was it two?
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B
Surprisingly intact. The Guru I was at is in. In the knowledge management space.
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A
Okay, different guru. Oh, I know that. I've heard of that one as well. Okay, so that I'll wipe out that question then completely.
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B
No worries.
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A
I was curious whether you, whether you did believe in outsourcing and. Or if you are very much kind of hiring keep people from within so we can sidestep that question completely. So talk about the. I'm curious how you stay entrepreneurial and fast growth when the company is that, you know, 900 person. I mean you're, you're not the behemoth of like a Google, but 900 people is tough to get stuff done. Politics has absolutely started to be around. You know, you've got silos and how do you stay entrepreneurial and fast growth in those organizations? What do you do to bust through that or to.
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B
To.
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A
To keep away from the politics?
- [24:11]
B
Yeah. I think there's a couple of things that are really important. One is to instill in the culture that no matter what team department people are on, that everyone should stay as close to customers as possible. Whether that is creating opportunities for people to join, customer discovery interviews, to hear customer stories. Just that focus on here's what we're all here collectively to do, I think is one of the most critical things leaders can ensure. The second is to continue to really look at and ask the question of where is there friction in the organization? What are we doing that makes things harder? And to stay really open to that feedback from employees, whether they are veteran employees who will say, gosh, it used to be a lot easier to do xyz or their newer employees in their tenure who come in and say, huh, this, this feels a little unexpected. This feels like a little bit heavier lift. And so I think as long as leaders are staying very open and curious about those friction points and what is happening that makes things more difficult, then we can unpack and solve those. It's not letting those become inertia and just that the stories being told by employees, if it becomes the. This is just the way it is, or this is part of being a big company, then it becomes the reality. But if you say, hey, our priority is to stay as entrepreneur and agile as possible, this is what it means to do that, call us on it when we're not enabling that. The last, you know, you talked about politics and I think politics come from when people don't have shared clarity on the work that they're doing, who's doing that work, how it's reaching the impact and objectives and outcomes of the organization. Because then people start to create the okay, well if I don't know and no one knows how my work is impacting the purpose, then I've got to create my own stories and my own proof of that. Because I don't inherently believe that humans want to come together and spend their time politicking. I truly believe people want to show up and matter and know that they're making a difference. And so I think, and that's also fundamental to San is like providing that transparency and clarity. And again, emphasizing that as leaders, the stories that we share and tell have to be those ones around solving customer pain points, staying entrepreneurial, rewarding and recognizing when people are giving direct feedback to make something better versus rewarding and recognizing what's perceived as political.
- [27:09]
A
Yeah, I was almost curious whether, you know, building a sauna on a sauna helped you steer away from politics because it does give visibility to all of that. Right. It shows people the value in meaning their work. It shows people what they're getting done. It forces them to stay away from it.
- [27:22]
B
Yeah, definitely.
- [27:30]
A
Hey, it's Cameron Herold, your high energy leadership guru, here to pump you up on the second Command podcast. If you get frustrated because your managers aren't leading like you want them to be, check out my Game Changing leadership course@investinyourleaders.com that's investinyourleaders.com for just 347 per leader. You get 30 years of my proven experience straight from taking 1-800-got junk from 2 million to 106 million as COO and it's packed with 12 easy modules. Learn situational leadership, coaching, delegation, conflict management and more all in under six hours@investinyourleaders.com with straight to the point videos, worksheets and real life scenarios. Your team will master time management, be able to hire a players and get aligned with your vision. It's all backed by a 30 day money back guarantee and raved about by hundreds of CEOs and thousands of managers already learning from the content Grab this now and watch your business soar. Can you speak to the onboarding of. Because you mentioned onboarding earlier in your onboarding, I'm curious how you go about onboarding new senior and mid level people that you bring into an organization from the outside in two aspects. One, how do you bring them in and socialize with the team that you know, the seven of you did not get hired. We brought this person in above you, but we still love you and want to keep you. So how do you do that? And then secondly, how do you onboard new people so that they understand the culture and the DNA of the organization and their role and so that you onboard them at 100 miles an hour?
- [29:06]
B
Yeah, two really great questions there. I think the first one I have experienced deeply many times at high growth companies and I'll credit. I had a great manager at ebay when we were growing. So I joined ebay when we were about 1,000 employees and left when we were 10,000 after five years. So talk about a lot of growth. And I had a great manager who just drew a really simple diagram on a whiteboard one day when, when, you know, when we were experiencing all these pain points like all these new directors were being brought in and VPs and people wanted to know like why weren't they getting promoted as fast? And he drew this chart which said, hey, we are growing at over 100% year over year right now. And he said, no, humans grow at 100% year over year in terms of capability and learning competency. It is just not, we're just not wired that way. And different people are also on different parts of their learning curve and their mastery curve. And so to expect that every, you know, that you're just going to keep getting promoted and take on bigger and bigger roles. Everyone will get that opportunity because the company is growing. And of course we're going to put a priority on the people who know the customers, know each other, know the product, but it's just not going to on the outside look like the same rate for everybody. And I just, I always go back to that and share that with teens, which is bringing someone, if we do it well together, bringing a new leader in actually adds what I call new amplifying DNA to the team. That, done well creates actually more opportunity for everybody on the team because it can bring in a new perspective, someone who can help look around the corner, someone who understands how to scale a particular function or someone that just brings creative new ideas and good leadership coaching that all of a sudden gives the whole team different and new ways to grow. And so part of it is how to make sure people are included in that process and understand the outcomes you expect a new leader to drive in terms of both business and team. So being really clear on that and then having that inform onboarding. Right. To me, there's onboarding into the culture, the product, the business, and then there's also onboarding that's a continuation of the journey of the interview process, which is, hey, these were the beliefs we had on why we brought you in. Let's make sure you hit those milestones, and together we're achieving the outcomes that we brought you in versus, if not done well, oftentimes, again, because people are in maybe a wait and see mode, then it's like, all right, I'm going to wait on the sidelines to see if this person succeeds or fails versus, like, wait, we're all in this together. Like, our success depends on this new person's success.
- [32:13]
A
Yeah. And as a leader, you hired the person. It's your job to make sure they're successful because you love them when you hired them. It's your job to make sure you love them all the way through. I think.
- [32:20]
B
Yeah, definitely.
- [32:21]
A
You kind of touched on something and I want to mention. So I launched a course earlier last year called invest in your leaders. And my belief has been that a leader's job is to grow people. And there's a series of. I have 12 skills that I always want to grow people in. Situational leadership, coaching, interviewing, running effective meetings, one on ones, delegation, all the kind of soft skills of leadership. What areas do you or does Asana focus on growing their people? Because again, if the company's doubling in size, we've got to double the capacity of our people and their skill set every year or they're out of a job. Are there areas that you focus on growing your team?
- [32:58]
B
Yeah. One area that from the beginning Asana has invested in is making available to all employees conscious leadership training. So the 15 commitments of conscious leadership and providing a day and a half deep dive into it, I think that provides what's so important to doing that and making that available for everyone. And then having those practices available is it provides a common language and framework. There are so many different leadership frameworks and books and methodologies. I do believe at the heart of them, so many of them, there are similar themes right around accountability, around, like, how we show up, around how we understand and empathize with how other people are showing up. And so I think by beginning with conscious leadership and saying hey, this is a framework that we want to make available to all employees, and different employees are going to have different levels of engagement with it. But at a minimum, it gives us a common language and framework to bring people in to create a more shared experience. I think that's so important to do. Then we have an incredible team here in our people operations and learning and development. So make available. There's training every week around all kinds of topics in terms of management, decision making, allyship. And so I think that set of resources and just ongoing prioritization of learning and development is also really critical.
- [34:39]
A
I love that. All right, I want to talk. You mentioned earlier about staying open to customer feedback and really kind of soliciting some of that hard feedback from customers. How do you stay open as a leader to feedback from your peers? Like, feedback about you and feedback on how you can grow. How do you search for it? How do you stay open to it? I used to really take it very personally, and I almost got confrontational at times with my feedback. I felt like it was criticism, and now I'm way open to it. How do you stay open to it?
- [35:08]
B
Yeah, I couldn't agree more with you on that journey. And I think many of us go through that journey, especially people who have a high bar for themselves. And usually the reason we react to that feedback is like, somewhere we already recognize we could have done that better. And so. And then someone kind enough to point it out, you're like, oh, that hurts a little. So I. I have a. I have a favorite alternative analogy to the. There's a common phrase of, like, feedback's a gift, you know, which also kind of makes people feel like feedback can be unloaded on you in any form. And it's a gift, and you're, you know, you're supposed to be open to it. So my. My alternative is I have come to see feedback as like, a good workout, right? And the reason I like that analogy is, like, there's definitely some mornings where I'm not looking forward to the workout, but I know it's good for me. I feel great after I do it. But I also like that analogy because when I think about the feedback that if I'm taking a good class, you know, with a good trainer, the feedback that that person might give me is really to help me get better, to make sure I'm not hurting myself. But it's also very specific to me, and it gives me ideas of what I could do better in a particular exercise. I like that analogy because there's a few Things it's one not having to go into get any feedback session of all this feedback to give. It's a choice of how I take the feedback, what I learned from it, questions I should ask good questions because I don't understand the root of the feedback or what I could do better, then I can do a better job understanding and helping to unpack that. And then also in terms of giving feedback, if we so often I think again with that analogy of feedback's a gift, it encourages people to sort of just dump everything and be like, well I'm helping you. And I actually think to give good feedback you have to begin by deeply caring that, that it's going to help the other person get better at something. And so what's a way to share that? What's an example? When do you pick a moment when that person is open to it? Have you asked permission to see if they're open to that feedback? But to me having shift because I actually love giving and getting presents and I never felt that way about feedback. And so now that I think of it as a workout, I can separate the two and continue to enjoy gift giving but also just see feedback as a way that like I get stronger. Hopefully I'm helping other people get stronger.
- [37:59]
A
Can you. Is there something that you specifically do to ask for feedback or to get feedback? Like do you have a question or two or do you have like a survey you send out or do you use something like 155 like how do you get feedback when you're looking for it, when you, when you want it, before someone's maybe offering it up?
- [38:15]
B
Yeah, I actually like all different formats depending on the situation and my relationship with the person. But in general I just like asking open ended questions like is there, is there something or what could I do better? You know, we just had a meeting, we just had a conversation. Is there anything that you know, I could provide greater clarity on? Is there anything that's confusing, you know, but just sort of asking those questions of like what could be better? I also like to ask questions of like what, you know, what seems to be going well. What would you like to see me do more of? So some of the more of less of questions, you know, is it landing? Is it not landing? Why? Why not? I think are always like good beginning threads and it just sort of reinforces ideally for everyone. Like I'm always open to feedback and then, and then I think as a leader I think it's really important to then publicly share hey, I got this piece of feedback right? This Is something somebody or many people shared with me of what I could be doing better or what we could be doing better. And so here's the steps I'm going to take because then it, then it helps people see like giving feedback actually matters. It actually leads to change. And then I think structured ways, you know, as an organization where we actually of just diving into our employee poll survey that we do twice a year, there's gold in that, in the free form comments that employees take the time to share. And so for me, reading in their own words what they're excited about, what they wish we did differently, there's just no better way for us to improve as an organization.
- [40:06]
A
Yeah, it's huge. I find sometimes when I'm looking for feedback is I'll be in a situation and I feel like the energy just went flat or something. I might be coaching somebody. I'm like, oh, that kind of sucked. I'll be like, hey, what can I do better? Because I know it didn't work right. Whereas other times I'm like, wow, that was awesome. It just felt good. It's. Whenever the energy feels flat, I usually kind of loft something out and they're really apt to give it to because they know it kind of sucked too, right?
- [40:30]
B
Yeah. And maybe bringing back to the framework that we have of conscious leadership, there's a concept of like facts versus stories. And, and so often the things that we're like, oh, this is the truth, this is a fact, is actually a story that we're telling ourselves. And so even just approaching it that way, like when there is a situation where energy level is down or like the meeting didn't go well, is even just beginning with like, oh, I have a story that that wasn't how we wanted it to go, or I have a story that that wasn't how I wanted it to go or that my, you know, like we didn't achieve the outcome or that felt like there was more friction or more uncomfortable than it needed to be. What was your story? You know, even just that like opens up the conversation in a different way.
- [41:14]
A
I love that. All right, I've got a final question before we wrap up. Can you give us some thoughts around how companies should work better with a board? With a board of directors or board of advisors, how can we get more from a board than we do?
- [41:29]
B
Yeah, I, I love that question. Because a couple of the boards I'm on, we recently went through kind of an evaluation reevaluation process of how we wanted to work together with the management team. I think that, you know, I do think it starts with that which is like, what does great look like and what does excellence mean for that company at that stage with that board? And. And then where are the gaps today? Right? And often it often from even just like board meeting and time spent standpoint, it often, you know, the friction points or the like, gosh, we're not getting as much out of often is because that hasn't been clearly defined or redefined. Right. Which is like the time, the precious time we all spend together and the time that the management team spends preparing for these meetings. What does a good outcome look like and what does the company need over this next arc of its journey? Sometimes that could. There is that arc that is always sort of strategy. But underneath that strategy oftentimes there's the. Over the next 18 months, 24 months, these are the most critical things. And then it's like then are we spending our time on the most critical things versus it can often become again like a habit, like anything else, which is like we should share all these different things. And then we use the two and a half hours out of three just reporting out. And then the board feedback is like we're not talking about the right things. And so it's sort of just unpacking that and starting with the what does great look like and being willing to. And I'll caveat this that the boards I'm talking about are still private company boards because there's a whole set of requirements and things that have to happen for a public company board. But with the private company boards, it you began with just the let's, let's unpack that and then let's experiment. Right? Let's. For the next meeting, we've all said this is what we want. So we want more time, deeper dives on more strategic challenges. That was both the boards I was on. That was something identified. So then it was like, how might we create that and how might we have that conversation? What do we do more in pre reads? What do we do live? How do we structure those live conversations? And then afterwards, did we achieve it? Did we not, you know, how do we evaluate ourselves on it? And then iterate.
- [43:56]
A
So I just had, not only have I had my pen just blow up on me as I'm talking to you, but one of our members of the COO alliance knew that I was interviewing you and in backchannel just asked me a question that I think is really interesting. When have you had imposter syndrome that you know, you like, how the heck Could I be in this role? This is way over my head or whatever. And then how have you gotten yourself through that imposter syndrome that I think we all find ourselves in once in a while?
- [44:23]
B
Yeah, I'm smiling big at that question because I was actually asked that. It was right after I joined the Gusto board and Josh, who's the CEO and founder there, like kindly hosted me for a fireside Q and a chat with the team. And someone asked that. Someone said, oh, you know, imposter syndrome is something that I face. Like, have you ever faced that? And I said, I faced that this morning, getting up and saying, like, I'm going to do a Fireside chat in front of all these employees and be expected to have all these smart answers of like, what does success look like and how do you build this amazing career? And I, you know, in that moment it was like, oh, do I, do I have smart enough answers ready? Is it going to be insightful enough? Is it going to help as many people as possible? And so, you know, I share that because like, I think, I think everyone on the inside has moments, no matter where they are in their career, where they're like, oh, do I, you know, am I good enough for this? Am I going to be successful? Did they make the right decision? And I think for me, going back to even the beginning of our conversation for me, the way that I've kind of recognized it, so it's not trying to get over it, it's trying to understand, hey, what triggers that? Why do I feel that way? And then over time for me it's just been, I don't have all the answers. There is no way that I'm ever, especially in high growth tech, ever going to have all the answers and all the confidence, especially if the jobkeeper getting bigger and bigger because the company keeps getting bigger and bigger. But what I can do is go back to the can I ask the right questions? Can I stay open and curious? Can I bring as many wonderful people along the journey so that we create better solutions? And can I stay in learning mode? Because as long as I'm staying in learning mode and growth mode, the fears that we have of failure, like our lesson, because okay, maybe I am going to make a mistake, we all make mistakes. But if I stay in learning and curious mode and I am with the right people, we will learn from that and get better and stronger.
- [46:42]
A
I love that. All right, I want to go back to final question to the 22 year old Ann Ramondi and I want you to give yourself Some advice that you wish you'd known when you were 22 that you know to be true today.
- [46:54]
B
Oh, so much. 22 year old Ann Ramani I would just say one piece of advice is take more risks. Especially in the world of technology, there's such rapid change and doing things that feel a little or a lot uncomfortable where you're like, huh, I have no idea how this is going to turn out. Those have actually been some of the best experiences in my career with some of the best people. So I think that like, you know, giving yourself permission to take risks, I think the other is very much and so much easier to say now. But I, but I believe it deeply is just enjoy the journey. You know, enjoy the journey and don't worry about the destinations. Like so often at 22, I think it's, there's, it feels like there's just these set destinations in a career and if I, you know, if someone had told me what the, all the different things I would have the privilege to do over my career when I was 22, I probably would have looked askance at them like, what are you talking about? You know, what are you talking about? That I'm going to work at a, you know, I'm going to sell diamonds online, or I'm going to be part of a survey company that had a monkey as a mascot, or that I'm going to be part of an industry that completely changes, like how software is bought. I think those possibilities just would have felt so foreign at that time when I graduated. But so I would just say take risks and enjoy the journey.
- [48:36]
A
That's great advice. Amramundi, the COO for Asana thanks so much for sharing with us on the Second in Command podcast. Really appreciate the time and the experience share today.
- [48:46]
B
Thanks so much. It was such a joy to spend the time with you and I really appreciate the invitation you've been listening to Second in Command brought to you by COO Alliance Founder Cameron Herald. If you enjoyed this episode, please be sure to like, share and subscribe to us on Apple Podcasts, Spotify and our other podcast streaming platforms. For more best practices from industry leading COOs, visit COOAlliance.com.