Ep. 198 – Asana COO & Head of Business, Anne Raimondi

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Our guest today is Asana’s COO and Head of Business, Anne Raimondi. 

Anne 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, Raimondi is also a Lecturer in Management at Stanford Graduate School of Business and she is currently serving on the board of Gusto, Patreon, and Guru while having also served on the board of directors for SendGrid, Bloc and ThredUp. 

Anne holds a B.A. in Economics and Sociology and an M.B.A. from Stanford University. 

In This Conversation We Discuss:

• The importance of product focus to produce growth in the business 
• What kept Anne intrigued to be a board member of Asana 
• What makes Asana fundamentally different from other productivity management tools 
• How to stay entrepreneurial and fast growth with over 900 employees 
• Areas of focus for the team 
• How to stay open to feedback   

Resources:

Connect with Anne Raimondi: LinkedIn 

Asana – https://asana.com

Connect with Cameron: Website | LinkedIn

Get Cameron’s latest book “Meetings Suck: Turning One of The Most Loathed Elements of Business into One of the Most Valuable

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Before we jump into the episode, you need to know about two important ways that we can help you and your company grow. Number one, check out the COO Alliance. It’s for COOs Presidents, VP Ops, or whoever is your company’s second in command to the CEO. The COO Alliance is the world’s leading community for the second in command, and it gives COOs the tools and connections to grow themselves and the company. Head over to COOAlliance.com to learn more about our members and the results of the program, and our 10X guarantee. If you qualify for membership, you can set up a complimentary call with our team to discuss if it’s right for you. I will tell you about number two in a bit. First, let’s start this episode.

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Our guest is Asana’s COO and Head of Business, Anne Raimondi. Anne first joined us on as board of directors in 2019. She is an industry veteran with over twenty 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, and Chief Revenue Officer at TaskRabbit. She held senior positions with Survey Monkey and eBay with a strong commitment to fostering innovation in the technology sector. Raimondi is also a lecturer in Management at Stanford Graduate School of Business, and she served on the board of directors for Gusto, Patreon, Guru, SendGrid Block, and Thread Up. Anne holds a BA in Economics and Sociology and an MBA from Stanford University. Anne, you are a classic underachiever.

I’m going to invite you to introduce me to my children.

That’s a crazy bio. You 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 now?

If I trace it all the way back, it’s my willingness to stay curious and keep learning. I started out my career as a management consultant and discovered that I like business problems, but also business and people and team challenges. I found my way to becoming a product manager. I credit a lot of the rest of my career path to that early product training of customer discovery and development. Asking the five whys, what’s at the root of it, and how do you create many possible solutions to solve a problem? I would also say timing. I was fortunate to enter the workforce at a time during the dot-com boom. All these businesses were being built for the first time with the growth of the internet. I saw the possibility of startups and scale-ups. I would credit those two things for creating lots of doors that opened.

I’m going to date myself then. I’m going to travel back in time with you to March of 2000 when Steve Ballmer stood up and said that there was an internet bubble. We’re all like, “Don’t tell on us.” The whole stock market collapsed. The NASDAQ crashed by 78%. Why would you stay in that space? Why did you stay in that sector? It was fun from ‘97 to maybe 2000, but why did you stay?

When he said that, I was living in Seattle, selling diamonds online.

I was in Seattle too.

Chasing it back to being at a startup, Blue Nile, and what later led me to join eBay, why I stayed was the customer pain point. Yes, there was a lot of froth in that era. If you look back, for lots of businesses, the original concepts are huge businesses now. They’re not in the same iteration as the dot-com boom. When I looked back all the way to what kept me engaged was we were re-imagining how to solve customer pain points. 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 these shared passions.

Prior to a platform like eBay, if they could travel, they would have to go to annual shows and meet one another. If they had a local antique business, they were limited by the number of people that they could attract. All of a sudden, eBay opened up all these possibilities. That combination of a customer pain point and then seeing real entrepreneurial spirit kept me motivated. There will be ups and downs in the technology industry, but this desire to create and improve life for other people is motivating.

I understand why you stayed and probably what got you to where you are. I was living in Seattle at that same time period. I probably bumped into you at Belltown Billiards and I was living at 2nd in Vine. My office was at 1st in Belle. I loved that whole area.

We were neighbors because the Blue Nile was down there. I lived on 5th in Queen Anne. I’m positive we passed each other.

Tini 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.

Yes or packs of gum. If you ran out of gum, they also delivered that.

Also DVDs. With product focus, do you think that it’s critical for COOs to understand product and product development? It feels like it is.

I will caveat this, being my experience is within technology and different industries within technology. I do think it is important for COOs to understand the fundamentals of what you’re putting out in the world. Within a technology organization, those are products and your customers. What are your customer’s pain points and what’s the strategy around building that product? There are different flavors of COOs and we will probably get into that. Certainly, as a head of a business that’s responsible for go-to-market and how we meet our customers and how we serve them, it intimately is related to how our product is built, why we are building it the way we are, and how we deliver together for our customers. My partnership with our RnD organization is extremely critical to our ability to grow the company.

You’re at a company right now whose brand is super strong. It’s a publicly traded company. Your career is strong. What keeps you there versus being poached to go somewhere else?

I fundamentally love a couple of things here. One is the problem that we’re solving. I feel like this is the problem I’m meant to solve. You mentioned me going to Stanford undergrad. I was an Organizational Behavior Major, as well as Econ. From an early standpoint, I love problems like, “How do you help humans work better together?” That’s very much the problem that we’re solving at Asana. How do we reduce friction in teams of all sizes, and make sure people’s talent and time are put towards the most important problems in the world, and spending time there versus what we call “the work about work.”

The second is I love the people that I got to know, the leadership team and employees, during my time as a board member. Especially over the last few years of what the world has gone through, I deeply believe that who we spend our time matters so much, and it changes us. It can change us for the better if we pick wisely. The problem that we’re solving and the people I get to solve it with are why I get excited to wake up early every morning and come to work.

When you were on the board of Asana, how big was the company back then? How many employees approximately?

When I first joined, we were probably about a third of the size of where we are now.

Can you say how many employees?

We were probably around less than 300 employees.

You are now bumping into the 1,000 mark.

Yeah.

Was it a board of directors at the time or a board of advisors?

It was a board of directors. I joined as the first independent director.

You didn’t seem bored enough to be on boards. What was it that kept you intrigued as a board member?

I have found over my career that sitting on boards made me a better operator. As an operator, so much of my day-to-day can be reactive, especially in growth companies going through a lot of change. I enjoyed the opportunity to be on board because the conversation at that level is strategic. It needs to be. I would go back to my day job asking better questions and tying my work better to the strategy of the company. I was motivated there of balancing that strategic view with my day-to-day operating role.

Now I’ve come to see that boards have done well in terms of thinking about governance and having the opportunity to change not for the company itself but if they’re seen as a leader in the space. Things like DEI and pay equity, boards are governing those decisions. I feel like it’s such an important opportunity to make an impact in more people’s lives if I pick wisely with boards and companies that are pioneering change.

Asana: It’s such an important opportunity to make an impact in more people’s lives if you pick wisely with boards and companies that are pioneering change.

I love that it deepens or richens your operational expertise as well. You said something about the product. I want to talk a little bit about Asana. If you’re in business, you’ve heard of Asana. Can you explain to people why Asana is different than some of the other project management tools or tools that are in and around your space?

I think our fundamental difference is how our founders, Dustin our CEO, and JR who is the cofounder, met each other and worked together at Facebook. They decided to solve this problem when they were at Facebook and built an internal system there, which then motivated them to start Asana. It was very much architected from the beginning the concept of what we call the work graph.

It’s not just about task management or project management but it’s also about understanding all the elements of what comes together for teamwork, in particular, cross-functional teamwork. It’s the who, what, when, why, and all that context. That richness in our data architecture translates into real benefits for anybody who is using Asana. To make it more concrete. Me coming in as a new leader, I had gone through a lot of seed-level onboarding in my prior lives in high-growth companies, bringing on other C-level execs. Onboarding a new exec is usually a heavy lift for the organization and the team. There are special meetings, decks created, and ways to update. You want to ramp up a new leader. You want them to make an impact.

The difference here at Asana is because we run Asana on Asana, I did not have to have a special meeting or special content created for me to get up to speed on what was happening and the decisions that have been made. Probably, the most important for me is the 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, contributions, and successes even before I meet them. That’s the power of Asana. It’s that contextual information around the work that gives people clarity.

You dovetailed into a question that I was burning to ask you, which I will ask now. In 2005 or 2006, I was down at Microsoft’s head office with about 120 entrepreneurs and CEOs from around the world. I was there as a COO and we were being taught project management by the head of Microsoft Project. After day one, partway into day two, he stopped and said, “I need to tell you something interesting. Microsoft has banned the use of Microsoft Project inside of Microsoft.”

We’re like, “What?” He goes, “We don’t allow it to be used because it’s too complicated and it slows everyone down. All we use is Excel.” We were like, “What is wrong with your company that you build something you won’t even use?” You said Asana was built on Asana. Was that because Dustin was entrepreneurial in a fast-paced growth company and wasn’t the big bureaucratic Microsoft? You guys have crushed the project.

I would credit to this deep passion that Dustin and JR had for great user experience. You shared about Microsoft banning the Microsoft Project because it was too complicated. I think Dustin and JR understood that to do this well, people have to enjoy and want to use it. There are less well-designed alternatives that break at a certain point, like spreadsheets, docs, and emails. 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. From the beginning, it’s a simple user experience that’s intuitive but then also fun.

Asana: In order for us to truly realize the value of a product like Asana, people have to want to use it and see it as a great place to get their work done and collaborate with colleagues.

When you check off tasks in Asana or complete projects, a unicorn might come across your screen. If you’re like me, there’s a feature where you can turn on extra delights. Who turns down extra delights? We need more of that in our life. There are lots of those moments of surprise and delight, and also appreciating and celebrating your colleagues. The other thing that’s built into Asana is when someone completes something, and comments on something that you’re doing or shares something, you can thank them easily and show that appreciation. I think that builds stronger relationships too.

You’ve listened to and built it for humans, and then you also built it for Gen Y. Because you built it for Gen Y, the Baby Boomers love it as well. Microsoft Project and some of the old legacy project management systems were built for engineers and project managers, and it never bled into the rest of the organization. You are right in listening to the consumer. I want to ask about Dustin quickly, not so much about him as a human, because I am very intrigued with Dustin Moskowitz. What did he see in you to bring you on as a COO?

I feel strange answering that question about myself in the third person. Maybe I will flip it around and say that when Chris Farinacci, our retiring COO, shared the news that he is headed towards a well-deserved retirement after an incredible 30-plus year career, and six amazing years at Asana, he and Dustin reached out and said, “You know the business. You know the team. What do you think about this opportunity?” It was probably the only operating role at that time that I dove into and said, “100% yes. I’m so excited given our stage and the scale of the opportunities ahead.”

To come back to your question, my hypothesis is that one of them was that we had a chance to build a relationship over two and a half years and get 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. That’s my hypothesis on the reasons we had a trusted relationship, and he knew how much I cared about the team and the business, as well as how much I care about the problem that we were solving. I’m going to have to ask him that question.

I’m intrigued. I know you’re the right hire for sure, but I’m curious as to what they see. He is a classic entrepreneur. I would imagine a little bit of an ADD or 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?

I would describe Dustin differently. I think he is incredibly intentional. He is absolutely a visionary founder and CEO. He’s got a long-term vision for the problem that we solve. I think that is rooted in a deep understanding that how you help humans work well together in any size team, especially in larger organizations, in solving some of the most complex problems is not an easy thing to do. Humans are inherently complicated, especially very smart humans, with lots of different ideas of how to solve problems. That long-term view that Dustin has is incredibly motivating. He goes about decision-making and empowering people in an incredibly intentional way.

What I have found is this. Unlike the stories that we hear, and even the experiences you and I probably both had with other founders, where there is almost this frenetic nature of they have so many ideas and they’re trying to get them out so quickly, Dustin is quite self-aware. He does a good job of knowing how and when he should have an impact and knowing how to empower the people around him. That self-awareness is also something that helps all of us get better. He models a way to lead that I think is quite exceptional.

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. For some of their own use cases, how do you know when to say no? 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?

There are a lot of tropes in Silicon Valley, in particular, about listening to the customer, not listening to the customer, and whether the customers know what they want. My deep belief is the customers absolutely understand their pain points. They definitely know what doesn’t work for them, what they are trying to solve, and how they wish it could be solved better.

Asana: Customers understand their pain points. They know what doesn’t work for them, what they are trying to solve, and how they wish it could be solved better.

Our responsibility in building a product and a platform. We want them to be accessible to many customers of many sizes as possible. It is to look for those underlying commonalities that then inform what we say yes to and what we say, “How about an alternative” to, and stay creative because we want to solve their problems. They may come at it with a solution that is not the complete solution or doesn’t solve the pain point as completely as we want for them and many other customers.

Especially in 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. We’re particularly excited about that. We do not see ourselves as creating something bespoke. We think that the shared learnings across the incredible customers that we have will accelerate our ability for more people to have more time towards their mission.

This is a bit of a side question, but I’m curious about your background at Guru, which is one of the original outsourcing platforms. I remember back when it was Guru and was it Elance?

It’s different. There are two Gurus, not surprisingly. The Guru I was at is in the knowledge management space.

I’ve heard of that one as well. I will wipe out that question completely. I was curious whether you did believe in outsourcing or if you are very much into hiring and keeping people from within. We can sidestep that question completely. I’m curious about how you stay entrepreneurial and fast growth when the company is 900 people. You’re not the behemoth like Google, but 900 people are tough to get stuff done. Politics has absolutely started to be around and you’ve got silos. How do you stay entrepreneurial and fast growth in those organizations? What do you do to bust through that or to keep away from the politics?

There are a couple of things that are important. One is to instill in the culture that no matter what team or department people are on, 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. That focus on “Here is what we’re all here collectively to do” is one of the most critical things leaders can ensure.

The second is to continue to look at and ask the question of, where is the friction in the organization. What are we doing that makes things harder? Stay open to that feedback from employees, whether they are veteran employees who will say, “It used to be a lot easier to do X, Y, Z,” or they’re new or employees in their tenure who come in and say, “This feels a little unexpected. This feels like a little bit heavier lift.”

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. If the story that is being told by employees becomes, “This is the way it is,” or “This is part of being a big company,” then it becomes the reality. You say, “Our priority is to stay as entrepreneurial and agile as possible. This is what it means to do that. Call us out on it when we’re not enabling that.”

You talked about politics. I think politics come from when people don’t have shared clarity on the work that they’re doing, who’s doing that work, and how it’s reaching the impact, objectives, and outcomes of the organization. People start to create like, “If 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.” 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.

That’s also fundamental to Asana. We’re providing that transparency and clarity. We’re emphasizing that as leaders, the stories that we share and tell have to be those around solving customer pain points and staying entrepreneurial. Also, rewarding and recognizing when people are giving direct feedback to make something better, versus rewarding and recognizing what’s perceived as political.

I was almost curious whether building Asana on Asana helped you steer away from politics. It does give visibility to all of that. It shows people the value and meaning of their work. It shows people what they’re getting done. It forces them to stay away from it. You mentioned onboarding earlier, and 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 the seven of you did not get hired, we brought this person above you, but we still love you and want to keep you. How do you do that? Secondly, how do you onboard new people so that they understand the culture and the DNA of the organization and their role so that you onboard them at 100 miles an hour?

Two great questions there. The first one I have experienced deeply many times at high growth companies. I had a great manager at eBay when we were growing. I joined eBay when we were about 1,000 employees and left when we were 10,000 after five years. Talk about a lot of growth. I had a great manager who drew a simple diagram on a whiteboard one day. We were experiencing all these pain points. All these new directors and VPs were being brought in. People wanted to know why they weren’t getting promoted as fast. He drew this chart that said, “We are growing over 100% year over year right now.” No humans grow at 100% year over year in terms of capability and learning competency. We’re not wired that way.

Different people are also on different parts of their learning curve and their mastery curve. To expect that you’re going to keep getting promoted and take on bigger and bigger roles, everyone will get that opportunity because the company is growing. Of course, we’re going to put a priority on the people who know the customers, know each other, and know the product, but on the outside, it’s not going to look like the same rate for everybody. I always go back to that and share that with teams. If we do it well together, bringing a new leader in adds what I call a new amplifying DNA to the team that if done well, will create more opportunity for everybody on the team.

Asana: Bringing a new leader in adds a new amplifying DNA to the team that, if done well, will create more opportunity for everybody on the team.

It can bring in a new perspective. It’s someone who can help look around the corner, understands how to scale a particular function, or brings creative new ideas and good leadership coaching that all of a sudden gives the whole team different and new ways to grow. 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 clear on that, and then having that information on onboarding.

To me, there’s onboarding into the culture, the product, and the business. There’s also onboarding that’s the continuation of the journey of the interview process, which is, “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.” If not done well, oftentimes, people are in a maybe a wait-and-see mode. It’s like, “I’m going to wait on the sidelines to see if this person succeeds or fails,” versus, “We’re all in this together. Our success depends on this new person’s success.”

As a leader, you hired the person. It’s your job to make sure they’re successful because you loved them when you hired them. It’s your job to make sure you love them all the way through. You touched on something. I launched a course called Invest In Your Leaders. My belief has been that a leader’s job is to grow people.

I have twelve skills that I always want to grow people in like, situational leadership, coaching, interviewing, running effective meetings, one-on-ones, delegation, and all the soft skills of leadership. What areas does Asana focus on growing their people? If the company is doubling in size, we’ve got to double the capacity of our people and their skillset every year or they’re out of a job. Are there areas that you focus on growing your team?

From the beginning, one area that Asana has invested in is making available to all employees the Conscious Leadership training, so the fifteen commitments of conscious leadership, and providing a day-and-a-half deep dive into it. What’s so important to doing that, 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, books, and methodologies.

I do believe that at the heart of so many of them, there are similar themes around accountability, how we show up, and how we understand and empathize with how other people are showing up. We begin with conscious leadership and saying, “This is a framework that we want to make available to all employees.” 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.

That’s so important to do. We have an incredible team here in our people operations and learning and development. There’s training every week around all kinds of topics in terms of management, decision-making, and allyship. That set of resources and ongoing prioritization of learning and development are also critical.

You mentioned earlier about staying open to customer feedback and soliciting some of that hard feedback from customers. How do you stay open as a leader to feedback from your peers? 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 take it very personally. 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?

I couldn’t agree more with you on that journey. I think many of us go through that journey, especially people who have a high bar for themselves. Usually, the reason we react to that feedback is somewhere we already recognize that we could have done that better. Someone was kind enough to point it out and you’re like, “That hurts a little.” I have a favorite alternative analogy. There’s a common phrase, “Feedback is a gift,” which also makes people feel like feedback can be unloaded on you in any form and it’s a gift and you’re supposed to be open to it. My alternative is I have come to see feedback as a good workout.

The reason I like that analogy is there are definitely some mornings when I’m not looking forward to the workout, but I know it’s good for me but I feel great after I do it. I also like that analogy because when I think about the feedback that if I’m taking a good class with a good trainer, the feedback that person might give me is to help me get better to make sure I’m not hurting myself. 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 are a few things. One is not having to go into any feedback session of, “This feedback is a gift.” It’s a choice of how I take the feedback and what I learn from it. I should ask good questions because I don’t understand the root of the feedback or what I could do better. I can do a better job understanding it and helping to unpack that.

Also, in terms of giving feedback. With that analogy that feedback is a gift, it encourages people to dump everything and be like, “I’m helping you.” To give good feedback, you have to begin by deeply caring that it’s going to help the other person get better at something. 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? I love giving and getting presents, and I never felt that way about feedback. Now that I think of it as a workout, I can separate the two and continue to enjoy gift-giving. Also, seeing feedback as a way that I get stronger. Hopefully, I’m helping other people get stronger.

Is there something that you specifically do to ask for feedback or to get feedback? Do you have a question or two? Do you have a survey you send out” Do you do something like 15Five? How do you get feedback when you’re looking for it or when you want it before someone is maybe offering it up?

I like all different formats depending on the situation and my relationship with the person. In general, I just like asking open-ended questions. What could I do better? We just had a meeting. We just had a conversation. Is there anything that I could provide greater clarity on? Is there anything that’s confusing? It’s just asking those questions of what could be better. I also like to ask questions like, “What seems to be going well? What would you like to see we need to do more of? It’s some of the more-of or less-of questions. Is it landing? Is it not landing? Why or why not? I think these are always good beginning threads. It also reinforces ideally for everyone that I’m always open to feedback.

As a leader, it’s important to publicly share, “I got this piece of feedback. This is something somebody or many people shared with me what I could be doing better or what we could be doing better. Here are the steps I’m going to take.” It then helps people see that giving feedback matters. It leads to change. I think of structured ways as an organization. We’re diving into our employee poll survey that we do twice a year. There’s gold in the free-form comments that employees take the time to share. For me, reading in their own words what they’re excited about or what they wish we did differently, there’s no better way for us to improve as an organization.

Asana: Giving feedback matters because it leads to change.

I find that sometimes when I’m looking for feedback, I will be in a situation where I feel like the energy went flat or something. I might be coaching somebody, I’m like, “That sucked. What can I do better?” I know it didn’t work. Whereas other times I’m like, “That was awesome,” and it felt good. Whenever the energy feels flat, I usually left something out, and they’re apt to give it too because they know it sucked too.

Bringing it back to the first framework that we have of conscious leadership, there’s a concept of facts versus stories. Often the things that we’re like, “This is the truth. This is a fact,” is a story that we’re telling ourselves. It’s approaching it that way. When there is a situation where the energy level is down or the meeting didn’t go well, even beginning with, “I have a story about that wasn’t how we wanted it to go,” or “I have a story about that wasn’t how I wanted it to go,” or “We didn’t achieve the outcome. That felt like there was more friction or more uncomfortable than it needed to be. What was your story?” Even just that opens up the conversation in a different way.

I’ve got a final question before we wrap up. Can you give us some thoughts on how companies should work better with a board of directors or board of advisors? How can we get more from a board than we do?

I love that question because a couple of the boards I’m on went through a reevaluation process of how we wanted to work together with the management team. I do think it starts with, “What does great look like? What does excellence mean for that company at that stage with that board? Where are the gaps today?” From even a board meeting and time spent standpoint, the friction points are like, “We’re not getting as much out of.” Often, it’s because it hasn’t been clearly defined or redefined. With 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?

What does the company need over this next arc of its journey? There is that arc that is always strategy. Underneath that strategy, over the next 18 to 24 months, these are the most critical things. Are we spending our time on the most critical things? It can often become a habit like anything else. It’s like, “We should share all these different things,” and then we use the two and a half hours out of three just reporting out. The board feedback is like, “We’re not talking about the right things.” It’s unpacking that and starting with what does great look like. I will caveat this that the boards I’m talking about are still private company boards.

There’s a whole set of requirements and things that have to happen for a public company board. With the private company boards, it began with, “Let’s unpack that. Let’s experiment. For the next meeting, we’ve all said this is what we want. We want deeper dives into more strategic challenges. In both the boards I was on, that was something identified. It was like, “How might we create that? 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? Afterward, did we achieve it or not? How do we evaluate ourselves on it and then iterate?”

One of our members in the COO Alliance knew that I was interviewing you, and asked me a question that I think is interesting. When have you had imposter syndrome that you’re like, “How could I be in this role? This is way over my head,” or whatever. How have you gotten yourself through that imposter syndrome that I think we all find ourselves in once in a while?

I’m smiling big at that question because I was asked that. It was right after I joined the Gusto board. Josh, who’s the CEO and founder there kindly hosted me for a fireside Q&A chat with the team. Someone asked that. Someone said, “Imposter syndrome is something that I face. Have you ever faced that?” I said, “I faced that this morning, getting up and saying, ‘I’m going to do a fireside chat in front of all these employees and be expected to have all these smart answers of what does success look like and how do you build this amazing career?’” At that moment, it was like, “Do I have smart enough answers ready? Is it going to be insightful enough? Is it going to help as many people as possible?”

I share that because everyone on the inside has moments, no matter where they are in their career, where they’re like, “Am I good enough for this? Am I going to be successful? Did they make the right decision?” Going back to even the beginning of our conversation, the way that I’ve recognized it is it’s not trying to get over it. It’s trying to understand what triggers that. Why do I feel that way? Over time for me, it’s been that I don’t have all the answers. There is no way that I’m ever going to have all the answers and all the confidence, especially in high-growth tech and the job keeps getting bigger and bigger because the company keeps getting bigger and bigger.

What I can do is go back to, “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? Can I stay in learning mode?” As long as I’m staying in learning mode and growth mode, the fears that I have of failure are lessened. Maybe I am going to make a mistake. We all make mistakes, but if I stay in learning and curious mode and I’m with the right people, we will learn from that and get better and stronger.

I want to go back to the final question to the 22-year-old Anne Raimondi. I want you to give yourself some advice that you wish you’d known when you were 22 that you know to be true now.

One piece of advice is to take more risks, especially in the world of technology. There’s such rapid change. Doing things that feel a little or a lot uncomfortable where you’re like, “I have no idea how this is going to turn out.” Those have been some of the best experiences in my career with some of the best people. I think that giving yourself permission to take risks. The other that is so much easier to say now, but I believe it deeply, is to enjoy the journey and don’t worry about the destinations. Often at 22, it feels like there are these set destinations in a career.

If someone had told me all the different things I would have the privilege to do over my career when I was 22, I probably would’ve looked at them like, “What are you talking about that 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 how software is bought?” I think those possibilities would’ve felt so foreign at that time when I graduated. I would say take risks and enjoy the journey.

That’s great advice. Anne Raimondi, the COO for Asana. Thanks so much for sharing with us on the show. I appreciate the time and the experience you shared.

Thanks so much. It was such a joy to spend time with you. I appreciate the invitation.

That was great.

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• Anne Raimondi
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