Episode 9

From exec roles to board seats - Anne Raimondi's leadership lessons for the startup C-Suite

Today's episode is with Anne Raimondi, Chief Customer Officer at Guru, a knowledge management platform. Across her career in tech, Anne has been a founder, operator, executive and an independent board member at companies like eBay, SurveyMonkey, Zendesk, TaskRabbit, Asana and Gusto. In addition to her most critical leadership lessons for scaling up as an executive, Anne dives into her playbook for building impactful boards.

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Anne Raimondi: [00:00:00] I think that that differentiates the best executives, where they're truly a team player and they care about the whole business, even if they're just responsible for marketing or sales or product from a title or on paper standpoint, that they holistically look at the business and the company. And I think that is a differentiator for the most successful executives.

And it also allows them then not to just stay in that lane that they came in, but to take on whatever the next most important initiative is for the company

Brett Berson: [00:00:39] to in-depth a new show that surfaces tactical advice, founders and startup leaders need to grow their teams, their companies, and themselves. I'm Brett Berson, a partner at first round, and we're a venture capital firm that helps startups like notion, roadblocks, Uber, and square tackle company building firsts.

Through over 400 interviews on the review, we've shared standout company, building advice, the kind that comes from those willing to skip the talking points and go deeper into not just what to do, but how to do it with our new podcast. In-depth you can listen into these deeper conversations every single week.

Learn more and subscribe today@firstround.com

for today's episode of in depth. I am thrilled to be joined by Anne Raimondi ANZ had a long and impressive career with pit stops at some of the most interesting companies around. She was part of the founding team@bluenileduringthe.com boom. She then worked on the product marketing side of things that E-bay during its rapid growth.

And then after leading product marketing at survey monkey, when it was just 30 employees, she started a company that was acquired by task rabbit, and later shifted to operations as an SVP at Zendesk, where she led all internal facing teams for five years, she's currently the chief customer officer at guru, which is a knowledge management platform.

She also sits on the boards for Gusto, Patriot, and a sauna, and is a lecturer at Stanford's graduate school of business. What stands out of course is the breadth of these roles. Anne's been a founder operator executive and a board member at both consumer and enterprise companies at all different scales.

She's headed up product marketing, revenue and operations at big names throughout tech, giving her a unique range of functional expertise and lots of insights into different leadership teams and executive roles. And that's the focus of our conversation today. We dive deep into what makes for a great exac in board member, the pattern she's seen across her career and how leaders can grow into their roles.

What I found particularly interesting is how clearly she's crystallized the lessons from each chapter of her career, from what enables the best executives to scale up to how she's approached her own 30, 60, and 90 day plans as a new exec and doles out spot on advice for getting this critical transition, right, and sidestepping common traps.

She also touches on her systems for executive recruiting and interviewing, and when she minds executive talent internally, rather than defaulting to external hires, Finally, we discuss her impressive board work and the essential ingredients for productive, impactful boards across every growth stage today's conversation is a must listen to for executives, founders, and board members looking to level up their leadership frameworks and for folks who someday hope to step into those shoes, I hope you enjoy today's episode.

And now my company. Awesome. Well, thrilled to have you on the podcast. 

Anne Raimondi: [00:03:48] Thanks for having me 

Brett Berson: [00:03:50] want to start, was talking broadly about executives. What makes an executive great. And I'm specifically excited to talk to you about it because you've seen it from so many different angles in so many different types of companies at different scales.

And so maybe a good place to start is when you think about common characteristics across the best executives you've worked with, or when you think your best as an executive, what are the characteristics or behaviors that you see in those folks? 

Anne Raimondi: [00:04:19] I think of it really as great executives are great leaders, as well as great managers and the trades specifically, I think the most successful executives, meaning that they're successful in multiple places in multiple settings, not just in one company, that's a brand name, that's grown a lot, but that they're really adaptable.

They stay curious and they're just genuinely interested in learning deeply about the customers, the products, the team, the needs. They might have a ton of amazing applicable experience, but they don't come into a situation. Trying to apply a playbook. They might rely on that once they're really grounded in the particular situation and need.

But I think that curiosity is just one of the most important traits I've seen in really successful executives and leaders. 

Brett Berson: [00:05:21] Are there other things that tend to tie all the best folks together? 

Anne Raimondi: [00:05:25] Yeah, I think that they genuinely. Want to make the team around them successful. And that means both the executive team, as well as their own team and function that there are some, I would say, good functional executives who come in and they're great at their department or their lane.

Like they're exceptionally talented and they make an impact, but they just see their team as that team versus also seeing the executive team being one of the most critical teams. To keep healthy or make healthy and continue to improve. I think that that differentiates the best executives where they're truly a team player and they care about the whole business, even if they're just responsible for marketing or sales or product from a title or on paper standpoint, that they holistically look at the business and the company.

And I think that is a differentiator for the most successful executives. And it also allows them then not to just stay in that lane that they came in, but to take on whatever the next most important initiative is for the company. 

Brett Berson: [00:06:39] So can you share the stories or some of the folks that come to mind when you think of just really exceptional executives, a moment that stands out or some of the things you took away from watching them operate.

Anne Raimondi: [00:06:52] Sure. I've been really privileged to work with number of and continue to work with a number of reasons, talented executives. I'll start with, I spend a lot of time with Lexi reset Gusto. She's just a standout, I think, both in how she's grown her teams, the business, how she's a partner to the founders, how she really is able to do, especially in a growth setting, the combination of like a deep dive, she can roll her sleeves up and dive in.

Recently the customer operations group was going through some changes and she just dove in there. She does that with sales, but then she also knows when to kind of zoom back out. And that's also a unique trait. I think that's really important with executives knowing not to be a micromanager, but knowing when.

Diving deep and getting context can help you and help the team be more successful. So Lexi's absolutely a stand out when I was at Zandesk. It was really amazing to see Adrian McDermott and his journey with that company. Having started. He's one of those executives that started when the company was small and managing engineering, and then growing into being able to manage a globally distributed engineering and product team.

Be strategic on both what should be built internally and what should be built through acquisitions. And that ability to scale from a 30 person company to a thousands of people, a company is unique as an executive and part of, I think what makes him great is he continually look at like, well, what comes next?

And how do I grow into that? I think a lot of that also comes from the DNA of Zendesk and that's how McKell the CEO and founder operates too, in terms of like challenging themselves and not getting comfortable. 

Brett Berson: [00:08:52] Is that the key thing that allowed that executive to scale, it was just a constant questioning of what's next?

What are the gaps? How do I get there? Or was there something unique that made that individual be able to do that, which is quite rare to your point in terms of going from. Tens of people to maybe almost 10,000 people or something like that. 

Anne Raimondi: [00:09:12] Let's say it begins with like a humility. And I know we're talking kind of execs.

And I went over into founders a bit too, because I was thinking of like other exceptional people. And I have the privilege of working with founder CEOs who also are in the bucket of executives. So we can spend a little more time on that too. But I think that common trait is this humility that starts with like in many cases.

Okay. I am in the biggest job I've ever been in, or I'm leading the biggest team or I'm taking on something I've never done before. And to have the humility of saying, well, what's going to make me great at it. What's gonna make this team exceptional at it. And how do I. Fill the gaps that I have, how do I go seek outside help or help from my board and investors?

Or how do I reimagine how I'm running a certain team, everything from tactical, how do I reimagine how I'm doing my one-on-ones and leading my team meetings and what my team needs to. All right. I've never led this function before. I'm going to go meet a bunch of people who are known for being great at this function or having scaled this function to three X.

What mine is right now, and I'm going to learn from them, then I'm going to hear what they've done, but then I'm going to come back and I'm actually going to. Apply it. And I'm going to get feedback on how I'm doing. I think that's a critical part of the humility is like I'm figuring this out. And so I need people to really be critical of me and help me see the gaps so I can keep working on that.

And I think that's what I've seen the most successful execs who can truly scale and then the confidence again, to hire people around them that they would work for. I think that's another really key trait of great leaders is being really confident that I'm going to find people much better than me at not just the function, but I'm going to surround myself with people that are better at me at the things that I need to work on.

And I'm not going to only hire people who have less experience than me. And that's another, I think key attribute of leaders who've built just incredible teams. Who've been able to do things that no one imagined they could do on their own. And then they achieve that as a group. 

Brett Berson: [00:11:25] On that point. When you think about building out your own team and through the course of your career, recruiting people better than yourself, is there a specific approach or way that you did that other than sort of the obvious thing, which is starting out with a desire to hire that level of talent?


Anne Raimondi: [00:11:40] of what I enjoy about hiring and building teams is understanding people's motivations because the reality and you all see this all the time, right? Is that really talented people have so much choice. They can go anywhere and people who've. Worked with them before are trying to recruit them. They have opportunities to start their own thing.

And so I think with hiring, for me in the past, it's been understanding, okay, what's going to be interesting and exciting and a growth opportunity for somebody that then fits with what I am, the company that I'm at can provide. And so in concrete terms, that might be someone who's been really successful in later stage companies, but wants to be a part of growing an earlier stage company.

And they're excited about sort of the build stage. So looking for those people in companies that might be bigger, same flip side people who've just are functional experts and I've just demonstrated they can build from the ground up and now are really interested in, okay, where's an opportunity to scale.

And so understanding kind of career motivation, understanding personal motivation and values and culture. So often again, like the most talented people, because they have choice. I find that a lot of the really outstanding leaders at any level, they actually care the most about the people around them.

They care the most about the values and the purpose of a company. And so spending a lot of time talking about that and letting them see the inside of the company and team and not just doing the traditional. Interview recruiting process. My goal is that whoever joins the team is just super excited to be part of it.

And there are no surprises there because the inside of every company has its challenges and being really honest about what those challenges are and making sure those are the challenges that someone's excited about solving, I think creates the best opportunity for people to thrive. 

Brett Berson: [00:13:50] What have you learned or have you updated your internal frameworks from the worst hires you've made or the worst senior hires you've made over your career?

Anne Raimondi: [00:13:59] There's a higher failure rate in leadership roles, or often the term is organ rejection. And the 

Brett Berson: [00:14:08] costs of those mistakes are very high as well, because a lot of them are building a team around them and all sorts of other stuff. So it obviously makes sense to try to 

Anne Raimondi: [00:14:16] get it right. Yeah. It's really true.

It's worth spending a moment on that. Cause you mentioned something really important, which is like cost and it's not just like the cost of time of having brought that person on and onboarding them or the cost of replacing them. The worst ones are aware. There's scar tissue left on the team and there's cleanup after and there's trust damage done.

And that costs a lot to the team in terms of how to fix what became broken. And usually in the vast majority of cases, none of them, this is intentional. It's not like an exact came in intending for it, not to work. Almost everyone goes into these situations very much wanting it to work. But if that upfront relationship building, if the expectations aren't aligned, if a number of things have gone wrong, that the damage can be really expensive.

Just from a human standpoint. I've definitely lived through that. I think the mistakes go back to some of the things that we were talking about, like what makes a good leader. Some of the ones that I've seen high failure around is that the exac has been exceptionally successful at their last place. They built something that worked really well.

They had a great reputation for being awesome at that thing, that function, whether that's demand generation, enterprise sales, whatever that is. And they're coming into a new situation expecting to just apply that playbook. And oftentimes they're recruited because of that playbook. They did X super well at well-named company and they kind of come in thinking, this is what I'm hired to do.

I'm going to take that and I'm going to apply it in this situation. And what they don't do is pause and really understand like who's the team around me. Is this the right playbook? Are all the plays applicable? What else might I not know about the situation about these customers? Sometimes it's a slightly different customer profile.

And just that nuance, you know, can really affect a go to market leader. This may sound like totally settled, but if they've built a great sales organization that sells into sales leaders, and now they have to sell to marketers, or they have to sell to customer support leaders and they don't pause to kind of learn the new customer profile.

There's many of those where it's like, okay, I'm going to repeat what I'm great at, where there's the highest likelihood of failure. 

Brett Berson: [00:16:43] So, how does that inform the way that you evaluate executives now versus maybe before you learn this lesson? 

Anne Raimondi: [00:16:51] Yeah. I spend a lot of time more in conversation and seeing how they would approach the very real problems and challenges that the company is dealing with.

And just also a lot of it is actually seeing what questions they have and how thoughtful those questions are. Are they really asking the questions in the sense that they're thinking about? What would I do in this role? Are they starting to picture themselves in the company in the role? It makes a huge difference.

The people who are, and they're genuinely interested, their questions are just different. Their questions are as if they're already on the team versus. I would say maybe more of the superficial questions that you would ask more from like a financial investor lens, growth rate competition threats. Yes. You should ask about those things.

You should get smart about those things, for example. Okay. Good questions I've gotten before is helped me understand some of the most important customers. What do they look like? What was the last thing they shared that they really love about working with this company or the product and what's feedback that they've given of what they don't like and what would cause them to leave people who are really starting to think about, Hey, if I were part of running this business, what would I need to know?

What would I want to know so that I can make the biggest impact as fast as possible. Those questions just are very different. 

Brett Berson: [00:18:17] So, if you think about your own journey and you think about you had a playbook and a set of frameworks and org structures, and what have you in your role at Zendesk, and then you went to guru and I'm sure to your point, there are some elements that are transferable.

And some that aren't, they're kind of in adjacent businesses. How would you describe how the playbook was updated for guru or what are the principles that applied from your Zendesk experience and what are the principles that had to be thrown away and sort of rewritten. The 

Anne Raimondi: [00:18:48] things that are broadly applicable are just understanding that different stages just the organization goes through.

And I think what I brought from Zandesk degree was more of the perspective and the experiences to be able to help the team have context on why certain things were happening at certain times. I know that sounds kind of vague. I had a number of conversations, both at guru, at a sauna at SendGrid around like what growth actually feels like on the inside and why it feels much harder than the stories that are written about high growth companies from the outside.

So I think that the context. Is something that I've found that I can bring, which is, Hey, different parts of the organization are going to grow at different rates. And that is natural, but there's some side effects that causes, right. There's going to be teams. Oftentimes they're the ops teams or the support teams that just are gonna feel more stretched and feel like things are breaking every day.

And they're going to look at some of peer organizations that feel like they're getting funded faster, and that's just a natural, all teams don't grow at the same rate at different stages. So giving people context and then saying, okay, for our company and team. What are the most important things that we get right, right now, from now until the next milestone and what are the things that we can allow to run a little hot or feel like they're a little bit breaking at the edges, but it's not going to fundamentally cripple our ability to be successful until the next milestone.

So those are just questions that we can then ask as a team and answer for ourselves versus saying, Hey, sales and marketing should always be funded and support should run lean. That's not a universal depending on your business. Right. But the concept of some teams growing faster than others is applicable and gives people context.

Does that make sense? Sure. 

Brett Berson: [00:20:50] So, can you give a few more examples of the things that you find to that point that are similar? Because you have a great set of experiences across both consumer and enterprise in different roles at different scales, and then the watching businesses from the board perspective.

And so those categories of things, or the framework that you think is broadly applicable versus maybe a story or two about some of the things that you learned and worked at one company and didn't work at another, 

Anne Raimondi: [00:21:17] the applicable ones for at least in my experience, go back to team and culture and values and making sure, you know, the leadership team founders are spending time really invested in values and culture and talking about it, reinforcing it, evaluating it, making sure it works for every employee, no matter how long they've been at that company and that the system of values and the culture that's being.

Reinforced as well as like grown and adapted helps every person make great decisions and make the team better. And then the specific values, how they're worded, how they're prioritized are going to be unique in each organization. But I've definitely seen it no matter what stage, whether you have 10 people or 5,000 investing that time and energy into your team, the values and culture is so, so, so critical.

And so I would say like, that's something that's been applicable across every team I've worked with. Then there's things more, I would say like around business model and go to market that really are going to be different just because a company is a SAS company doesn't mean that it's going to have all the same attributes as any other SAS company.

I mean, just the three I'm on boards of are all in the category of SAS, but they're all very different. Isana has both a self-serve and light touch motion as well as an enterprise. And they've got expansion, like that's really the business model Gusto just serves as and BS. So that's a very different SAS go to market model.

And then patriarch has got combination of sort of a SAS business model for their creators, but then also a marketplace aspect to it with patrons. And so, yes, they're all in the category of SAS, but the actual go to market strategies and tactics and how you test that are very unique. And so. Have to be applicable specifically to that business and that stage and what's ahead.

And then knowing that sort of diving into each company, it's then focusing on like, okay, what's of all the things the leadership team could be spending time on what really are just the couple, most critical that are going to make the difference. I think that's also something just asking those questions has been really important in any situation that I'm in, because there's always more priorities and always more things that people could be doing then there's actual resources and time, no matter what size company.

So when 

Brett Berson: [00:23:57] you think about executives making transitions from one company to another, and maybe you think about your own last transition, what is a great first three, six months look like? What should you be doing as an incoming executive to increase the probability that you'll have success there? 

Anne Raimondi: [00:24:13] I'm a huge believer in very transparent, 30, 60, 90 day plans.

And in fact, I think good interview processes actually transitioned into developing those 30, 60, 90 plans really naturally. So like, if you have done a good job, finding the right person and having good conversations, those conversations naturally lead to like, okay, what are the outcomes that this person is going to drive in their first 90 days in their role, especially as a leader.

And so for me in diving into any new role, it's what are the outcomes I'm looking to drive with the team around the business? For the first 30, 60, 90 days. And what are the team outcomes, culture, building the team, maybe understanding current team and talent and helping them achieve their professional goals.

And then with a 30, 60, 90 day plan leaving room in there for the learning. So who are the customers I should be spending time with to really understand and listen to what they love and what they wish we were doing differently. Really getting to know all aspects of the team, not just the team that I'm directly responsible for.

So spending lots of time across the organization at every level, and then really understanding the metrics deeply. I think that's critical for, again, any role. Oftentimes people will come into a role and just look at the metrics for their function, but I think good leaders should look at all the most critical metrics across the business to understand where there's the biggest opportunities for improvement and where are the superpowers of that particular business.

And then laying that out. There's lots of great templates out there and I'm sure people have adapted their own, but I like one where it's just really clear where it's like, these are the things that I'm working on. These are the people I'm meeting. And then these are maybe the projects or initiatives that I'm going to be a part of, making sure really land in this period of time.

Keeping it as a draft. And sending it around and asking for input again, from everybody on the team, not just direct reports, not just the founder CEO, but making it open depending on the size of the organization. It could just be everyone in that reports up to you. If it's a small enough company, it could be every employee and getting their feedback and both for myself and people that I've hired be a really, really good way to de-risk the first 90 days and make sure the leader's making an impact.

Make sure they're having the right conversations and make sure that other people have a vested interest in their success. That's the other thing, oftentimes when leaders come into organizations, whether we intend it or not, a lot of people are, have a wait and see we're excited about them, but is this going to work out?

And that comes from past failures, way back in my E-bay days, there used to be a term people would use for new execs, which was like hero to zero. How fast is someone going to go from hero to zero? Because people were kind of waiting and seeing if they were going to be successful versus like everyone should have a vested interest in helping to make that person successful.

How do you 

Brett Berson: [00:27:22] get people to behave or act like that other than just saying. Hey, we need to take a vested interest in this new VP of this or SVP of 

Anne Raimondi: [00:27:29] that. Yeah, definitely is easier said than done, right? When there's lots of everybody has their own 

Brett Berson: [00:27:34] priorities as 

Anne Raimondi: [00:27:35] well. So maybe even backing up to the interview process.

I do think it begins there. I firmly firmly believe that no one should meet their new boss on their first day of the bosses job. That's just such a terrible experience. And so it doesn't mean necessarily that every single person has veto power, but I absolutely believe that any direct report has to be part of the interview process and ideally the whole.

Functional team in some form or other. And that might be group presentation that might be lunch and learn what I like to do with the team. If they're not part of the group that's been designated as a final interview team, that gives feedback. I like to ask people for feedback on two fronts, like what they would be excited about with the new leader and what they're concerned about, and then sharing all of that feedback with the person you hire.

So this is what the team's really excited about all around. They're so excited. You're going to bring these things to the team. Here's what the team was concerned about and may just be like, Hey, we didn't learn this about the person or in their last role. They didn't have responsibility for this. Kind of team or function and the concerns then become, you can do a risk mitigation plan for those great.

These are the concerns. This is how we're going to address the concerns, but just that participation in the interview process, I think, starts to create that vested interest of the team of making the person successful. And then the participation in the 30, 60, 90 day plan, right? Giving input, seeing output, seeing updates on their 30, 60, 90, then it becomes less of a wait and see, like I'm sitting on the sidelines, seeing if this person is going to be successful.

If I have an active part in giving them feedback, if I have an active part in identifying potential risks, as well as an active part in identifying the things that I'm excited that they're bringing, it just feels a lot different than having sort of a new person, a shiny as they are show up. 

Brett Berson: [00:29:45] And when you think about the 30, 60, 90 plan, how do you think about balancing actually accomplishing something or outputs versus learning?

And I think there's sort of some fundamental tension where like a CEO or other executives in theory would subscribe to the person, has to become aware of the situation, understand the nuances that our business, et cetera, et cetera, where at the same time they want to see somebody fix this or launch that or get this thing out the door.

And there seems like there's some tension. And I assume that the 30, 60, 90 day is an opportunity to create alignment amongst everyone about like what's actually being done versus what's just intense learning. So that I can eventually be incredibly effective. Yeah. So do you have any thoughts about how you balance that?

Anne Raimondi: [00:30:32] I think a good 30, 60, 90 includes actionable measurable results. So having those outcomes, but the business outcomes and the team outcomes identified is really important that it doesn't just err, on the side of like lots of listening and learning, almost all of it's going to be situational to the person's role, the team and organization.

But I think making sure you have what I think of it is like quick wins in your 30, 60, 98. What's actually doable, what's measurable and then probably most important. What gives people a real opportunity to work together with you? The best way to build good bonds and de-risk is to work with someone in action on an important project or initiative, I think for good leaders.

They're going to be a balance of both the most strategically critical things, as well as sometimes there's quick win opportunities that are a little more tactical, but they're in that category of like no one currently owns this and we kind of think we need to do it sometimes just picking up one of those opportunities and showing people how you work and your quality of work can be really powerful in terms of, again, like building trusted relationships, building important bonds, as well as like making an impact.

Brett Berson: [00:31:56] There are other traps or things that you've noticed around incoming executives or things to be careful of. Naria that for me, that comes to mind, that's always tricky is as you're coming into an existing team and I'm sure that team has a lot of people that you think are great. There's probably a bunch of people that maybe need to be exited from the company there's new people that have to be brought in.

And there's a lot of. Things that are quite personal about that is kind of like one category of things that you should probably be quite careful of because trust and narratives and others can be set quite early on if that isn't handled thoughtfully, but are there any other things to be quite mindful of?


Anne Raimondi: [00:32:36] bring up something important, right? Which is you're joining an existing team and every team has its strengths and has its opportunities. And some are going to be healthier than others. And for a lot of executives you're brought in because there's something that needs improving on the team. There's some dynamic that for that next leg of the journey needs improvement, needs the bar to be set at a different level.

I would say there it is staying open-minded. You often are going to have heard this through the interview process or even experienced it yourself. If you're a C-level executive coming in, you're going to have spent time with the CEO who might be the founder as well with board members, with the team. And through that process, oftentimes people are pretty open about sharing what the challenges are.

I think it's continuing to stay open and seeing some of it for yourself to be able to make good judgments, but also being open to direct that you're doing that. And the pitfall to avoid is essentially like gossip started with, uh, well, I heard this about so-and-so or I heard this about you. Like that's not helpful.

You know, I think it's being open and direct of like, these are the areas that I'm going to spend time on. These are the things that I've heard are working really well across the team. These are the things I've heard so far that people think there's an opportunity to improve. And then getting people's feedback on that, I think is a great way then to really assess and use your judgment on is what I heard through the process.

Really the same thing that I'm walking into, sometimes teams have a great pulse on it and very quickly you're like, yup, they've diagnosed it. And then other times I think more often than not, it's like, okay, they've diagnosed a part of it, but there's more going on. Right. And so, and you can form your own approach then to like how you're going to address the pressing needs.

You said, what are other things I've seen people do? Well, as well as people sort of fail on, I would say one of the things I've seen people sort of fail on or skip over is there are great things. Assuming you're joining a growth company with a lot of passionate people who are building something awesome.

There's a lot of good going on. And sometimes I've seen leaders skip that part because maybe they're hired to fix something or there are sort of known challenges and they go jump straight to the, like, these are all the things that are broken, or these are all the things that the team's not doing. That very, very well, maybe true.

And what's also true is like, there's goodness going on. And so if you skip over the goodness and you don't spend time on the strains and amplifying those and recognizing people for those, you also kind of quickly lose trust or become known as the person who is sort of like seeing everything that's broken.

And then that can be a pitfall for exact set come from a more mature place. And coming into an earlier stage is like, you look around you. You're like, oh my gosh, there's no, there's nothing here that's been built or the way these decisions are being made. Isn't the way I'm used to a hundred percent true, but it also doesn't mean that it's bad.

It just means there's an opportunity. And it's good to look for the things that are really great and acknowledging those and amplifying those. Yeah, 

Brett Berson: [00:36:11] it's interesting how it seems like it's hard for incoming folks to do that to your point. Maybe they're trying to assert their talents or prove themselves, but it also kind of gets at the kind of an area that I'm always fascinated with, which is like the role of the individual versus the role of the system.

And nearly all cases, we overvalue our individual contribution and undervalue the system, not even the people and all of that, but just like the system we're operating. And I think that's always an interesting dynamic with executives. Like you, you very rarely hear someone say, you know, they had quote a lot of success in the last role, very rarely do they disentangle the system that they were playing in versus what they themselves brought or outcomes they themselves created.

I always find it's hard to disentangle those things. And as human beings, I think most of us over orient on ourselves. 

Anne Raimondi: [00:36:57] Yeah, no, that's such a good insight. And I think it goes back to the idea of like good leaders and executives stay really curious and they have enough humility to recognize. I was in a great situation, but I do think good leaders and executives have the humility to recognize, and we were doing it on a rocket ship.

And then to also have been honest enough of like, and these are the mistakes I made on that rocket ship that I wouldn't do again. And here's how I know that they were mistakes. I think that's important. I think if you, when you're interviewing executives, if they can't honestly talk about mistakes, that's another sign that they might not be a good fit because I don't know a single great executive or a leader who hasn't made mistakes, that they are happy to, like unpack and talk to you about and talk to you about why they learn more from some of those than the things that worked the first time around is that one 

Brett Berson: [00:37:57] of the main areas where you get at this idea of humility, or it's sort of a sense that you've developed over the course of spending time with someone or interviewing them where you can kind of score them on a humility index.

Anne Raimondi: [00:38:08] Yeah. Oh, that's such a good idea. Okay. That's a follow-up for us to build a humility index. I think it is from asking questions around mistakes, around learning around, or even just listening to how they describe their journey. Back to your point of if there's a lot of, like, I did this, I did this. That's sometimes the sign again, good leaders that are humble.

I think we'll talk about their team. They'll talk about, oh, and I, the best thing I did was like, bring this other person on because I learned so much from them. You know, they'll, it's just how they talk about success is often broader than themselves and is about teams. None of the organizations that we work with could exist and can be successful without being very team-based right.

All the work in the knowledge economy is team-based and it's people based. And so the people that are the best at it deeply recognize the difference, a high, high functioning team. That's very, trust-based, that's very learning and growth based. Just the difference that makes not only in terms of achieving outcomes, but just to work with and have fun and enjoy.

So I often find that great leaders like it, we'll talk about the experiences very much bringing in the teams that they are a part of. And it's a lot of, we, we learn this and these are some of the things we tried versus like, I did this and I made this happen. It's slightly 

Brett Berson: [00:39:37] related. When you think about an executive on your team and you think about their hiring accuracy, what do you think is good?

A miracle I would assume would need to happen for that person. For every single person they hire to be exceptional. Do you have a heuristic or you generally want to see X percent be successful? 

Anne Raimondi: [00:39:57] Yeah. I don't know that I have a percentage heuristic. I think that that would be a really good one to study. I think they are on top of it.

Meaning they're paying very close attention to an actively involved in the success of the people on their team. Good leaders are very attuned to how everyone's doing on their team and our course correcting. So that they give everyone every opportunity to be successful. Meaning they're getting feedback, they're listening for feedback.

They're giving feedback, they're getting feedback from the new person on what they could do better to help them succeed. And they're willing to make changes the answer. Isn't always exiting. I'm a big believer it's in fit that it's not a person being bad. It's, they're not the right fit for the role or the team.

And so if it's a growth company of a certain size, sometimes it's just getting yeah. Person into the right role. Maybe you hired them into a role that you had. I thought they were going to be great at, but it turns out that there's something off. Oftentimes they can thrive in another role and I've had that experience and all of a sudden, see someone sort of become an absolutely great superstar.

And those are actually the most rewarding when you've given somebody an opportunity to be successful. So I think the great leaders are assessing that and doing everything they can to make it work. And they are able to make a call. And make a decision when the situation's not going to work. And to me, the situations where, you know, it's not going to work is when you ask yourself the question like, well, is trust broken?

Do you trust this person to do the job, manage the team, be upfront with you on what's working. What's not working. Like if trust is broken and cannot be repaired, it's better for everybody to gracefully part ways and ideally give the person feedback and give them an opportunity to be successful in the next situation.

But good leaders have this whole possible set of things to do. And it's not just one or the other. It's growing your team. It's growing people and it's helping them get to the next level, whether it's with the current company or somewhere else. I know 

Brett Berson: [00:42:12] that you've been spending more time thinking about.

How do you create systems and cultures that enable more existing folks on the team to grow and potentially take an executive or senior leader role, instead of just assuming that given a certain scale, you have to go hire someone. And so I thought it would be great to get some of your thinking about that.

And maybe traps or frameworks or other things that folks can think about to do this? 

Anne Raimondi: [00:42:39] Well, yeah, it's something I'm really excited about and just the opportunity, especially for people that have been on teams for a while and are just grown with the company and are definitely in the biggest job they've ever been in.

But then can you give them the opportunity to keep growing or help them with that versus. Should of artificially say, Hey, at this next stage, whether it's going from series D to series E or whether it's preparing to be a public company, that the only answer is bringing in someone from the outside. And so I think the first part begins with intentional planning around executive team and looking again, as far out as you can with sort of reasonable information and then doing a good assessment.

So I'm working on one of these with a company that I'm on the board of, which is there was a conversation around executives and Hey, if we're planning to be a public company in the future, do we need to start looking for a C-level exec? Who's been part of a public company. And the conversation we've had is like, it's not an either, or we have a really talented person on the team.

Who's doing the role today, who has raised their hand to say that they want to stay in the role, ideally, but is also very self-aware that it's the biggest role I've ever been in. And so what we've actually done is partner with an outside firm to do an assessment. They do external benchmarking for this particular role, and they do a leadership in-depth assessment.

They do 360 interviews. They talk to the board about expectations of the role, and then they assess the current person against that role and external benchmarks. And what it'll give us is basically a roadmap to say, Hey, if this person were to continue growing in this role over the next couple of years, where are the biggest development areas?

And how easy or hard is it to really get successful at those development areas. And we're not done with this assessment yet, but if some of them are deeply technical and it's really like, Hey, it's pretty hard to do it. Then at least we have that information and we can be honest, but if some of them are like, yeah, this would be like coaching or giving the person an opportunity to take this particular area on and demonstrate proficiency would it allows us as also to have a really honest conversation with the person on the team and they get a roadmap on development, which is awesome.

And then the other opportunity it gives us, like if we come to a decision of, Hey, we don't think you're going to be ready. When we need you to be ready, it can also open up the possibility of hiring a very different profile person from the outside. Someone were really honest of saying like, Hey, there's a great person on the team already.

They have ambition to take on this role and grow into this role over time. We want to find someone who's super excited about that. Maybe this is the last C-level role they want to take, and they want one where they can groom someone like it could change the external profile versus bringing someone in that kind of caps, the development of the person we have on the team.

So. I'm super excited about that as a framework of is your work for anybody on the team. If you take the time, it certainly can work for C-level folks because there's a lot of organizations that do this and benchmark and can provide an outside perspective on what great looks like. But it could be a framework that you use for anybody on your team.

It gives them a development plan. It gives them really concrete things and expectations, but it also could shape who else you bring on to the team to help them with those. If you are to hire above them. 

Brett Berson: [00:46:21] When you think about avoiding the reverse, which is quite common, which is probably be categorized as the Peter principle, right?

Basically, and a lot of cases, the organization actually over promote someone for all sorts of different reasons. And the Peter principle is just generally that a high performer always ends up in a role that's too large for him or her. And so, is there anything you do to manage for that? And I just think you see this over and over again, right?

Someone was their first marketing hire and did an amazing job. And so there is a strong desire to have them stay and grow. And they ultimately end up in a role that they're not able to perform exceptionally yet. 

Anne Raimondi: [00:46:57] Yes. I've seen that a lot and been inside organizations, whether it was early on at eBay or when I was at Zendesk where that happened.

So the context I would give people first in the conversation is if an organization or a team is growing at call it a hundred percent year over year, or some of these are growing at 200% year over year, it's really hard for any human to grow their skills and capabilities at a hundred percent year over year.

I think the fastest rate of growth for humans is from zero to one. And I think it slows down as we get older. So just context. Why does it feel so hard? The second I would say is I don't believe things have to be an either or especially if you're having open conversations. So let's take that marketing sample.

It's super come. They're great. Generalists. They have figured everything out from scratch. They've built the team. But they're not yet ready to be a CMO. And maybe that's because that next level of complexity, maybe it is needing a few more cycles on sort of strategic decision-making. And so things that I think can be helpful to someone that doesn't just feel like, Hey, thanks for everything you've done until now.

And like here's your new boss is again, making sure they have an opportunity to go see what great looks like in that role in companies. That are a few stages ahead. Oftentimes again, great people that gives them the have like, okay, I've now just seen what excellent looks like a few stages ahead of where we are and what excellent looks like compared to the skills that I have and the experiences, especially in call it B2B SAS, oftentimes for marketers, it's like, oh, some of the best CMOs spent a good chunk of time in product marketing and they're just excellent product marketers.

And so that may open up the, okay, go build out product marketing, right? We are going to bring in a CMO, but we want you to take on product marketing and really build those skills out and be groomed to be the CMO here or somewhere else. Other things I've seen when people take on a function that they've never run before is supporting them with outside resources and not just like a coach or a mentor, but an actual resource.

When I took on people, operations at Zendesk, I'd never run people operations and McKell was super generous and. Introduced me to a man named Nancy Connery who runs a HR and talent consulting organization. And she was an expert at a function I'd never run before. And she was signed up to be a resource for me throughout my journey.

Like there's things that you can do to help support someone's growth versus just telling them that they haven't done it before, or they're not ready. I think when people know that, but they also want to know how do I keep growing as fast as I can and make as big an impact as I can for the organization.

I feel like rarely do good people want to just leave. Something happens in their experience. If they don't feel like they're supported in their growth that actually pushes them out. Then I don't think that's always necessary 

Brett Berson: [00:50:06] a little bit on this in the role of an executive. I think that you often have these conversations with folks that report to you about if they're a director, how they become a senior director or how do they have more impact and to your point.

There's often, if it's done really well, there's a series of gaps that are identified, and there's a lot of clarity in where a given person is and where they need to get to as a starting point. When you think about folks that have done the best job of then closing the gaps, versus what I find is quite common is there are gaps that are agreed upon and nothing really happens, or they think that the gap was closed and it wasn't really closed.

Is there anything you've seen in either the way that you work with folks on your team, or maybe when you think about your own journey in growing that helps someone close the gaps other than the desire to do so? 

Anne Raimondi: [00:50:54] I do try to encourage the development conversations, the ones that I'm having directly, or people who've reported to me who are having those conversations with their team members to as much as possible, not just be title and promotion based.

I know that's easier said than done. I know it's always easier for people that are already at a C level to be like, oh, don't worry about titles, but I mean that in the way of like, it shouldn't just be about that next title titles do serve a purpose, I think is important, both in internal and external signals.

So I'm not going to discount them, but I think the healthier professional development and career conversations actually have to do with mastery of skills and taking on different and new experiences. I've seen people grow sometimes the most when they take on. What on paper looks like a lateral role, but it's actually a whole set of experiences that they haven't had before at Zendesk that could be having people go join teams in other offices, whether that was in the us or outside of the country, be part of integrating an acquisition.

There were so many opportunities where we just saw people step function, career growth, because all of a sudden they were just in a much more intellectually stimulating situation for them. So I tend to like to have the professional and like gap conversations, really around like mastery of skills and ideally mastery of skills match to what the person is excited about.

And so for some people that could be within the function because they want to grow into being the SVP of sales or the CMO or the head of product. I find that I have more conversations where people are like, I'm still figuring it out. And so some of that just may be. General leadership skills, management skills, getting deeper into data, getting more familiar with the product, getting more technical.

So I think the good conversations matched to the person's real learning objectives, not just title objectives. And I think then those conversations back to like, what do I see, great people who then go out and do something about it. I think when they deeply connect those activities to things that they get enjoyment from, and they're highly motivated to learn, even if that means a few stumbles and failures, as they're on their road to mastery, I've seen that be more motivational versus like, Hey, here's the career ladder.

And here's the different levels. If you are able to demonstrate these things, then you're up for a promotion. Those start to feel more transactional versus truly motivational and a set of skills that the person will bring with them. Whether they get promoted at the current company or they go out and do something else 

Brett Berson: [00:53:44] before we wrap up and talk a little bit about some of your insights from the board work you've been focused on over the last few years.

Maybe we could just spend a couple minutes talking about the inverse of this conversation, which is how to be thoughtful as an executive, making the choice of where to go next. And I'm sure you've had these kinds of different inflection points in your career where you've kind of zoomed out and said, okay, I'm ready for something new and then ran a process or maybe it was more opportunistic, but I'd also assumed that you have lots of folks that you've kind of grown up building companies with, that are reaching out and saying, Hey, I'm thinking about something new.

How would you approach that? Or what would you look for? Or how do I figure out if this company is going to be well set up for me to be hugely successful? And so are there patterns or things you find yourself saying over and over again around this category of questions? 

Anne Raimondi: [00:54:33] Yes. I love this conversation and I do find that I have the conversation a lot, whether it's with people that I worked with before or a have the privilege of being part of a teaching team at Stanford business school.

So lots of amazing second year students are trying to figure out what to do after graduation. So I love this conversation. I think that kind of framework that I talk to people about that I've applied myself. I think of three categories to spend time on and ask yourself questions around the first is I think the mission and purpose and what the company does or what the organization does.

And if you are excited about it, you don't have to be the target customer, but if you just are like intellectually interested in this problem and excited about seeing it solved in the world, I think that's important to wake up in the morning and be really excited. That's the problem set that you're spending the majority of your day on and with other people who are excited about solving that problem.

So I think that's important because sometimes I'll talk to people who are like, okay, well, these are the list of companies on my target list and they're interesting companies and there's a wide range of them. And then I'll ask, okay, well, tell me why you're excited about each of these companies. And a lot of times the answer is like, oh, well, they have a good brand name and they're growing really fast.

And we're like, okay, well, do you like the product or the customer or the problem? And they're like, well, I don't know. I haven't used the product or I haven't spent a lot of time thinking about that. And you're like, okay, go do that because that's what you're going to. Wake up doing so I think that's super important.

The second is maybe tied to some of the conversations we've been having, which is, are you going to learn and grow and make an impact? So is the role or the stage, can it be challenging enough for you and both, you're going to get a lot of learning and growth and you're going to be able to make a good impact and those questions, and also help people maybe be a little more objective around title or role and not be so wedded to get specific title, but really if they can evaluate the opportunity from a growth standpoint and then the third, but absolutely the most important category is who are the people around you?

Who will you be working with? What are the values and behaviors of the organization? Not just what they say, but what they actually do. Do they open their doors and encourage you to talk to people who've left the company. And what did those people say? Do they invite you in? Or if you asked to spend a day with them, do they open those doors?

And does that experience mirror the one from your interview experience? Because frankly like the people around us change us for good or worse. And so that is so important that you really feel that the inclusion, belonging, that the values are lived not just said. And I think that makes all the difference in terms of real growth experience, meaning personal and professional growth experience for people.

And anytime I think people skip over that or kind of have a feeling like it might not quite be there, but the other two are good. Inevitably they're unhappy. 

Brett Berson: [00:57:58] On that sort of last area. Are there other things that a friend of yours is going through a SVP or C level interview process with company X, other things they should watch out for, or potentially yellow or red flags that they should just keep their eye on?

Anne Raimondi: [00:58:14] I do think they should be able to have an open conversation with whoever's hiring them in these situations. It's usually CEO, CEO, founder about other leaders that have left. Because in most of these situations, there's been some turnover. If the person can't have honest conversations around people leaving with enough specificity and depth and reflection, especially if they were regretted attrition, that's a flag.

That's certainly a flag that the person hasn't learned from past experience, or if every situation is someone else's fault, that's a giant flag. So being able to have sort of honest conversations of the things that haven't gone, right. I think the other would be again, like, oftentimes, especially if it's a first time founder, they may be hiring you for a role that no one else has had.

It's the first time there's a head of marketing. It's the first time there's a head of revenue. So they don't have to have the perfect job description or all the objectives. That's part of the fun of being able to shape that when you're a more experienced leader coming in and. It shouldn't be so vague.

There should be a point of view. I think that's a beginning of a conversation. So other flags would be where it just feels like they haven't actually paused and thought about outcomes or informed themselves enough about what the outcomes might look like, because then that could signal that expectations are going to be all over the place.

And you want to make sure that they're not all over the place, especially in the early days in that partnership. And then maybe last but not least, especially as it relates to founder CEOs. Do they listen to feedback? Do they want your feedback? Have they already sought it through the interview process?

I'll say that's often where, when I talk to friends, colleagues, who've gone into a startup and been super excited about it. They thought it matched all three of those criteria. And then it didn't turn out to work. Was that critical relationship with the founder that it wasn't a two-way relationship and that the person wasn't yet ready or open to hearing their feedback and really good experience execs expect that expect to be able to have that level of a conversation, both ways, listening to feedback and giving feedback.

Brett Berson: [01:00:39] Yeah, that's a great set of ideas. It also gets at the both great opportunity and peril in being the first of anything that a first time CEO is hiring for. Yeah. We could probably spend multiple hours sort of 

Anne Raimondi: [01:00:52] talking about that. Yeah, definitely on that really tactically, I think something I've seen work or can work for that founder.

Who's never hired the role before is work with someone who is great at that role. Even as an advisor, just for this opportunity and ask that person to interview your candidates specifically for that role, you, as the founder, CEO should still interview the candidate for values and behavior fit for how well you'll be able to communicate and solve hard problems together for how passionate they are about the company you're building and the product you're building.

But it's okay to ask someone who is a great CMO to like interview CMO candidates to see if they'll be great CMOs for you at this stage. And it can often be. So enlightening and actually for candidates, I think it communicates a seriousness and a thoughtfulness about the function and both what you know, and what you're still learning as a founder.

So that's a tactical one that I've seen and employ that works so well. It can really solve some of these mismatched problems that we were just talking about 

Brett Berson: [01:02:05] last year. I just wanted to chat about as your board experience. And I think what's really wonderful is you have a pretty broad set of experiences now, or the past, maybe call it three to five years.

What do you think makes a great board member maybe that could come in the form of telling the story of some of the folks who served on boards with that you've most admired at their behaviors? 

Anne Raimondi: [01:02:24] Yeah. And especially for maybe my perspective is also especially for operator board members. And then I've definitely worked with really great investor board members, but as an operator board member, you'll hear the advice of you're not there to operate.

And great operators often will go into solution mode. So you're really there to actually ask critical questions and really make sure. That if we get really technical yet you're representing shareholders, you're representing and ensuring that the leadership team is building an enduring company and business, ideally in a growth and sustainable way.

And so it is about knowing how to ask the critical questions. And so I would say. Traits that I've seen or things that I also try to make sure I'm aspiring to do. Certainly in the first leg of joining a board is learning good board members are more quiet than they are talking that they're learning about the business learning what the key issues are learning about the different perspectives of the other people around the team or on the table.

Other board members, I love asking existing board members. Who've been part of the journey longer. Their thoughts on what's working really well. Where are the opportunities for growth? If there was only one thing that they could change. What's that one thing they would like to see change, especially as boards evolve, what even works with the format of the board meeting itself.

Because oftentimes as the first independent board member at a number of the companies I'm working with, the company is growing into a new set of even board interactions. And so not taking. Anything for granted. Oftentimes the company has outgrown how they're doing board meetings, but they just haven't updated it yet.

So just being able to say like, okay, what does great look like for us at this stage? And even how we're having the conversations, what information we're looking at, how we help the team make decisions. And then I personally like to spend time, one-on-one not only with the CEO, but the other leaders. I like spending time with frontline employees in different departments.

It helps me get a better, deeper rounded view of the business all again, in the spirit of like the more context that I have, the more relevant and better, the critical questions that I can ask to help ensure that the company is growing in a healthy way. 

Brett Berson: [01:05:01] So on that point of asking critical or clarifying questions, can you share a little bit more of what that looks like, or maybe an anonymized story of when you thought you were the board did a good job of asking a certain type of question because it's easy to ask.

Good and bad questions. It's easy to fly at the wrong altitude. I think at the board where like the classic example of somebody talking about some color of a button on a website or detailed product feedback in a board meeting, maybe not the most useful format and the other is that it's so high level.

And so presentation oriented that it's kind of this dog and pony show where a CEO gets up and runs through 70 slides in three people say one word and that's a board. 

Anne Raimondi: [01:05:40] Yeah. I definitely have experienced all of those. So some healthy habits, I think all boards should have is not only having a closed session.

With a founder, but having a closed session without the founder CEO. And then most importantly, having a feedback loop from that closed session back to the CEO, just that habit can be life-changing for everybody. Cause often there are all these unsaid things from everybody's perspective, this founder CEO and their team gets a little frustrated when it's 70 pages and then they get three comments and they've spent a whole week getting ready for a board meeting and putting this beautiful deck together instead of running the business or trying to do both.

And then they're like, okay, we got three kind of unhelpful or mildly helpful comments that we probably could have gotten without putting 70 to a hundred pages together. So there's sometimes frustration on that end. And then there's frustration sometimes from the board perspective where it's like, Hey, it doesn't feel like we're talking about the right things.

It doesn't feel like we're spending enough time on strategy. So those are sort of common things, but they don't get fixed unless everybody's sharing that. And so I think one habit to get into, to start making sure that loop happens is having closed session debrief where people can be really honest if they're not yet ready to say it all directly to the CEO and then having a way to deliver that feedback and then act on it.

Once that habit comes into place, what I've seen over time is one everyone's excited that we're actually talking about the right things and then people get more comfortable actually sharing it without needing to have this structure. Everyone just gets better at being direct of like, I like this. I don't like that.

Could we try something new? It's almost like applying, I'm a product manager. It's applying a sprint retro, you know, dear board meeting, what's working, what's not working. What's something we want to try. Those are the kinds of questions I like to ask those open ended. And so I think that's a good habit that I've seen.

Can make a huge difference in the quality of conversation and then the strength of relationships, because the stronger the relationships are, the easier it is to have the difficult conversations. If you don't have that foundation, then the really hard sticky conversations around, Hey, is so-and-so exact, really working out.

Are they delivering what you had expected? That's often one where people skirt around because they Percy or board members skirt around until it's too late or until they're like, okay, you have to fire that person. That shouldn't be the first conversation you have with a CEO founder about someone on their team.

So I know there was a lot there, but happy to dive in deeper. Are 

Brett Berson: [01:08:26] there other things or formats rituals habits that you've seen that lead to the best board meetings or board member, founder, CEO dynamics. 

Anne Raimondi: [01:08:37] Yeah. One of my favorites that McKell did at Zendesk and Samir did at SendGrid. And now Dustin does at a sauna.

And Josh does that. Gusto is they write a board letter in advance of the board, meeting a narrative just from their perspective. Some are longer than others, but it's the voiceover. Before you get the deck, it's, what's on their mind over this last quarter. Here's what I'm really excited about and proud of that the team did.

And here's what keeps me up at night that in particular, so important for the board to know what is the thing that really is worrying your CEO, that for them, the sort of the most critical issue that's preventing them from getting. Good sleep, which your CEO should be getting good sleep as much as possible.

So just that letter has been so helpful in framing the conversation, right. Then yes, you still get the deck and preread, but it gives you context around like, okay, where we really need to spend time. Right. Is this topic that's keeping the CEO up at night. And so I've been really fortunate at all. Those CEOs just did such a good job being really open and honest in these relatively succinct flutters.

And it just changed the conversation at the board. 

Brett Berson: [01:09:57] Anything else like that, that you've seen that other people might consider doing to increase the quality of their board meeting or get more value out of their board 

Anne Raimondi: [01:10:04] members? A number of CEO's I work with will do either board debriefs or board pre-conversations, especially if there's something kind of big that they're working through or strategic, oftentimes they'll do these ahead of going through the strategic plan for the next year, or if they're doing like a three-year plan and there's a lot of depth to it.

They'll spend time. One-on-one just to make sure they're hearing everybody's perspective, but then they'll kind of circle back and make sure that context from those one-on-ones is shared with the whole board. So it doesn't feel like they're having different conversations with different people. I think that's a critical skill of like really treating your board as is that a high functioning team and especially one that doesn't have that frequent a set of interactions.

If they're only meeting quarterly. And if some of the board members haven't worked together before. So that's one, which is the balance of one-on-ones and going deeper on topics and then making sure your whole board is in the loop. The other would be inviting board members to events or conversations to be able to go more in depth, whether that's strap, planning, offsite.

Now that are virtually, but just inviting them to participate in parts, to get more context, encouraging board members to spend time with one another outside the boardroom and then giving time for as much as possible, some aspect of personal bonding as a group, whether that's right now for us on, oh, we're doing virtual happy hours before board meetings.

And it's nice. It's just nice to spend time with everybody. Not yet talking about the kind of business stuff, but getting to know each person more in depth. And I'm sure many companies are doing all of them or each of those things that I've talked about, but the combination again, of sort of investing holistically and creating a high functioning board.

Because if those, again, if they're not comfortable talking to each other or giving each other feedback, that's also going to put a damper in the ability to have robust conversations in the discrete time that you have together. 

Brett Berson: [01:12:14] Do you have any thoughts on what should be covered in a board meeting? What is worthy of a board meeting topic versus 

Anne Raimondi: [01:12:21] not.

A lot of it depends on the stage there's topics for public company boards. There's a set of topics you have to cover. So I'm going to answer this more from like a pre-public company perspective, because I think that's where there's a greater range and it evolves a lot from early stage to late stage.

Maybe more like as a diagnostic, if you're spending a lot of your board meeting doing just updates and read outs, you're probably not getting the most out of that time. And I think the topics that are worthy of bringing to a board, even if your board right now is all investor board members, like these are people who are seeing across a lot of other interesting businesses.

They're strategic, they know your business and you should be digging in on things that are hard, that you should be digging in on the decisions that are the messiest ones. Like too often. I see founders. And maybe it's because they have a lens to the next round of fundraising. And so like, Hey, we want to show that everything's going well, but there's always something that is hard at high growth startup.

Like there is every single one, no matter how lovely they look on the outside, on the inside, it's hard work. And so, so I think really unpacking those hard decisions. It could be strategic roadmap decisions. It could be which customer segment you might have multiple customer segments now, and some are performing on some metrics better than others.

And like, do you deep dive on one and spend a little less time on another? That's a hard decision because both are generating revenue. So there's always something that is what the leadership team or the CEO is spending time on. If that's not discussed at a board meeting, I think you're missing out on an opportunity to get really smart people who have a vested interest in your business being successful, helping to dig in.

Now having said that framing, that conversation is really important, right? So you'd rather spend your time in board prep, framing that conversation, maybe asking your board members to do some pre reading and homework ahead of time on that topic to come informed and ready to have a conversation, I think is the most fruitful versus lots of functional updates that they could read asynchronously.

If it's not a significant decision, or if something's not significantly off track, those should be more like pre reads. You should be spending like in-person time on meaty topics 

Brett Berson: [01:14:51] maybe to wrap up. Are there a story or two that comes to mind of where you felt was the moment of Nirvana or things worked like the board and the dynamic was hugely impactful to the company.

Maybe the CEO behaved in a certain way, or there's a board member that you really admired that you thought ended up really delivering on the promise of what a great board looks like. 

Anne Raimondi: [01:15:14] The privilege of having many of those, the one that I would love to share. Cause I think it's super important in terms of building really diverse and inclusive boards is I had the privilege of working with Fred ball, who was the lead independent at SendGrid.

So when I joined, there were other independents, I was not a former CEO or a CFO, which are generally the profiles, more common profiles to join. I'll say, I think we're getting better at different profiles that can be additive to boards. And it was my first public company board. So Fred. And all the other board members, but as the lead independent really went out of his way to make me feel welcome.

Get me caught up on context and specifically a conversations outside of the board meeting, getting me up to speed on the issues, making sure that I knew which topics that were top of mind for the board members, as well as for the CEO and exec team. And just really making me feel not only welcome, but fully up to speed and included.

And then Fred ran a great. Debrief closed session. That's a model that I now use as the independent and the lead independent at Asana, which is making sure you hear from everyone. So really kind of giving every one on the board, an opportunity after a board meeting to share how they thought it went, what they thought went well areas for improvement, specific feedback for the CEO or any other member of the executive team summarizing it all.

Making sure that it's accurately reflected and then sitting down with the CEO to go through all of that. And then circling back with the whole board to say, I've had the conversation I gave the feedback. Here's the follow-up. It was just such a great model around inclusion, transparency, high functioning from a communications standpoint, but also from a growth standpoint.

So that's really the one that has sort of shaped my experience, especially because it was my first time being a public company board member. Oh, 

Brett Berson: [01:17:29] that's a great place to end, particularly because it's also kind of a very specific tactic that I think folks can use when they think about designing their board 

Anne Raimondi: [01:17:36] meeting.

Yeah, it is absolutely. And it's one you can model and that just provides so many rewards and I've benefited from them. And now that I'm applying at other places, I've also certainly experienced the benefits. And a lot of that is just deeper, great relationships and conversations with groups of very talented people.

So I credit Fred for that. 

Brett Berson: [01:17:57] Awesome. Well, thank you for spending all this time with us. This was 

Anne Raimondi: [01:18:00] awesome. Thanks, Brett. I really enjoyed the conversation.