Diagnose Before You Deploy: Smarter Strategies for CEOs with Michelle Valentine

Randy Wootton (00:05):

Well, hello, everybody. This is Randy Wootton, CEO of Maxio and your host of SaaS Expert Voices where we bring the experts to you to talk about what’s going on in SaaS today and what does the future hold. This is the first time for us on SaaS Expert Voices we have a repeat guest, Michelle Valentine, CEO of Anrok. I’m super excited to have you back, Michelle. Very specifically today we’re going to talk about a different aspect of building companies, and that’s how do you do it successfully as a CEO. We have been chatting a little bit about this over the time we’ve gotten to know each other, and so thank you, Michelle, for coming back and imparting some of your wisdom.

Michelle Valentine (00:39):

Excited to dive back in.

Randy Wootton (00:43):

As a starting point, as some people know, I’ve been working on this book, at some point it’ll get done. It’s called The Seven Secrets of Success for CEOs. What I will do is I will just catalog them really quickly and just describe what the seven secrets are and then, Michelle, you’ve got some comments on a couple of them. Then I think what’s going to be really interesting is how you thought about developing yourself as a CEO, and that falls under one of them, which is what have you been doing very specifically to broaden your perspective or what I’ve described as sharpening your spear? How do you get better at the job? To set the context, the seven secrets of success at the highest level, and people can read this on my LinkedIn, include driving overall results, specifically like shareholder value, because if your company isn’t thriving then you’re falling short. I think in the change in the market landscape, we’ve seen that play out and I’m sure you have lots of friends that are all super anxious about the results, so that’s number one.

(01:36):

Number two is establishing a winning strategy so everybody knows what businesses they are in today and where we’re going forward. Number three is shaping values and standards that will guide your company over time because there’s never a right answer. There’s always a series of choices and we need to use our values and standards to help us make clear where we’re going to go. Number four is building an effective executive team because you only have one pair of hands. Number five is managing your board and investors and setting the right kind of expectations, which we talked a little bit about your background last time and I think this will be great conversation there. Number six is allocating capital to balance the yield today with the necessary improvements, and then number seven, investing in your tribe. That means working with mentors, coaches, peer groups or building out a personal advisory group or panel to help you make the best decisions you can. Michelle, with that framing of those seven, where would you like to start? Which ones really resonate for you and what would be some of your thoughts?

Michelle Valentine (02:36):

You have to start at number one. Outcomes matter. That’s the reason why that one I think is your number one. What I come back to is people want to work on winning teams, and so results matter, rallying the team and seeing what you’re doing together is really important. Creating a culture that holds people accountable and stretches people for those goals is absolutely the number one thing that a CEO needs to keep their eye on. That said, to get to number one you really need number two, creating that winning strategy to get to those results. Something that we’ve done at Anrok is writing a short memo of why we think we’ll win as well as think about why we might lose and making sure that we have a plan of attacking all of the reasons why we might lose. This type of thinking is something we call Murphyjitsu at Anrok. It’s a term that’s borrowed from Center for Applied Rationality, so it’s not an Anrok original but it’s one that the team uses a lot, which essentially comes from this idea of Murphy’s law, anything that will go wrong will go wrong. It’s all about creating that plan to think about how do we make sure that things that could go wrong don’t go wrong?

Randy Wootton (03:54):

Let’s talk about that, Michelle, if you wouldn’t mind just a second because that is something I think again with your background as an investor that you’ve been able to look at businesses with an impartial view and think about what’s going to work, how it’s not going to work. You probably in many ways as you’re looking to make investments… I always think about it as they’re looking to kill deals more than invest in deals. Is that where your initial skillset, you developed this idea of how to work through the scenario planning and really step into the space of, “How could we fail?”

Michelle Valentine (04:27):

Those are similar frameworks. They’re different in one key way, but first I’ll talk about the similarity that you notice. For investing, the question is often like, “How does this go right?” Because it’s more easier to go wrong than go right, and so in investing it’s more about dreaming the dream and how big could the dream be and could it get there. In venture capital, it’s so easy to pass on a deal because it’s much easier to think about the ways it could go wrong, and so getting over that hurdle to actually invest and thinking about how could this go right is often the harder question to answer as an investor whereas as an operator, you are faced with all of the many things that can go wrong, you’re already in the seat, and your job is to really think about making sure that your team doesn’t miss the mark or miss an opportunity.

(05:19):

Going back to this Murphyjitsu framework, let’s say you’re working on a product launch and the question you can ask is, “Well, our go live date is January 1st. How surprised would I be if we missed the product launch date?” You’d say, “I wouldn’t be that surprised. I think we’d probably miss the product launch date.” “Okay, let’s think about all the ways it can go wrong and ensure that we have a plan to make sure that dates don’t slip or QA is done on time or we beta test correctly.” Now once you have all of those things in place, you almost go through that simulator again and think about, “How surprised would I be if this went wrong?” You might think to yourself again, “I still wouldn’t be that surprised if things went wrong.” Then you think about, “Okay, well, what else could go wrong? Marketing might not be prepared and might not have had a sufficient heads up. Okay, we’ll create a plan for that.” You keep going through this in a simulator several times until when you finally ask the question, “How surprised would you be if this went wrong?” You’d be, “I would be very surprised if this went wrong.” That’s when your plan is ready to be set off into the wild and execute on that plan.

Randy Wootton (06:28):

I remember the last time we were chatting, you were talking about this confidence interval and that when you write up plans, you assign a confidence interval to it and 60, 70, 80% so that you’re indicating to people when they’re reviewing your plan how confident you are in the ability to execute. I imagine this process, this Murphyjitsu, is part of how you increase your confidence for the different documents that you’re putting together or plans. Is that fair?

Michelle Valentine (06:56):

That is fair. I think the other way that you might use the confidence interval where you wouldn’t apply the Murphyjitsu framework is a strategy. The confidence interval is like, “How confident are you? Is this the right or wrong strategy to pursue?” Murphyjitsu is best applied to when you’re actually operationalizing something, when you know this is the right problem to go after or the right strategy to use. It’s more thinking about, “How do you operationalize this in a way that you minimize the risk that things go wrong?”

Randy Wootton (07:27):

Great. Help me understand… You only have so many hours a week. You could be spending time in terms of creating new ideas, building out product plans, doing some troubleshooting, but not the deep think cycling on what could go wrong and creating mitigation plans. How do you balance that? Maybe think about or maybe frame which things do you apply the Murphyjitsu to and then what’s your expectation in a week? How much time are you spending Murphyjitsu-ing versus creating?

Michelle Valentine (08:02):

The more important problem, I think the more important it is to make space and time for Murphyjitsu. It often comes up in a meeting setting. If I’m feeling a little bit worried that something might not go to plan, it’s a really useful framework to almost call out the elephant in the room without calling anyone specific out and framing it as a problem that we can all work on together. What’s helpful is that Murphyjitsu has a very cute name and it makes something scary, like thinking about risks and way things can go wrong, as if it were a fun game. I use this framework I would say almost weekly across all different departments, across product launches, across partnerships, across hiring like, “How surprised would you be if this person was the wrong hire?” And just thinking through like, “Okay, let me simulate if we hire them, what could go wrong? Okay, have I asked references about this way it could go wrong? Do I feel like we’ve tested all of the different aspects of what this hire will be doing for me to feel confident this is the right exec in the seat?” The more important the problem, the more important it is to make space for Murphyjitsu, and I do this at least weekly.

Randy Wootton (09:15):

That’s great. Sorry, it came from the Center for Applied… What was the last part?

Michelle Valentine (09:18):

Rationality.

Randy Wootton (09:19):

Rationality. Wow. Okay. Well, I have never heard of it. It sounds great. I think what I’m struggling with is my own sense of… I tend to be one of those guys that’s always defaulting to the optimistic potential outcome and I’m just going to gut it out and we’re going to do it because we’re just going to brute force it rather than spending the extra cycles to scenario plan and think about it. We do try to do some mitigations, but certainly not at this level. I do like the idea of it depersonalizes things.

Michelle Valentine (09:50):

Mm-hmm.

Randy Wootton (09:51):

One thing in our company we talk about, which lots of people talk about, are big rocks, so big opportunities are big problems. I’ve never used this framework before so I am going to go find the book, find the group, and apply it. That’s awesome. That really helps you feel more confident about the results you’re going to deliver and sort of double-clicking down into that from the winning strategy to specific tactical plans that you’re going to be executing that would then enable you to realize the strategy that you’ve articulated. Is that how they come together?

Michelle Valentine (10:26):

Yes, and it’s about tapping into something that I think is innate in all of us, which is the ability to play out a movie or simulate an environment, but we often don’t use that skill deliberately enough. Usually that’s something that comes out in a daydream scenario or maybe when you’re really optimistic, you’re playing out that movie, and we don’t apply that skill set that we innately have to downcase scenarios enough.

Randy Wootton (10:52):

How do you keep it… Do you do this with your executive team in person? Do you get together on a monthly basis and run through a set of future plans and say, “Okay, we’re going to Murphy this thing and Murphy that thing,” and everyone plays? Or maybe another question is how much coaching does it take to take people who haven’t experienced this and change the way they think about approaching problems and plans?

Michelle Valentine (11:15):

I think if you do it enough, it becomes part of the culture where now teammates at Anrok often bring this up without me, and it’s a good way for… Often high-performing team members have a lot of fear and concern that things might go wrong, and so for them it gives them a tool to put it out in the open to their team to say, “Hey, let’s Murphyjitsu this for a minute.” They might be worried that their teammate might drop the ball on something, and this is a good safe way to bring up that fear and allow the other person to say, “Hey, I’ve got this. I’m committing to this date or this date.”

(11:49):

I’ll give you an example of how it organically came up up actually already this week, it’s Monday, where we were going through our Q3 plan for one of our go-to-market teams. We looked at all of the things that we committed to and we paused to think, “Hey, how surprised would we be if we ended the quarter and didn’t complete all of these things?” We identified something that was missing because we were not surprised if we’d complete the quarter and things were missing, that we didn’t have kickoff dates for the different projects and we didn’t put those different projects in the context of a timeline and assign DRIs that were committed to kicking off those different projects and all we… Yeah.

Randy Wootton (12:32):

Sorry, what’s a DRI?

Michelle Valentine (12:34):

Directly responsible individual.

Randy Wootton (12:36):

Ah, okay. Mm-hmm.

Michelle Valentine (12:41):

One of the things that we do when we plan every quarter is to often bring in this Murphyjitsu framework to have a sense of, “Hey, if things went wrong this quarter, what went wrong? Are we resourcing correctly? Are we setting the right timelines and making sure that we catch things before the quarter ends?”

Randy Wootton (12:57):

Well, that’s great. That almost starts to bleed into the third secret of success, which is around shaping values and standards that will guide your company. This is one of your habits or patterns that when people come to Anrok, they’re going to learn it, much like with… I think about the memo at Amazon where they write the six-page memo and everybody reads it when they’re in the meetings so everyone’s operating from the same, pun intended, sheet of music, but are operating with the same information and they comment and then the discussion starts. Maybe expand on that a little bit. How else do you think about shaping values and standards that will guide your company over time?

Michelle Valentine (13:33):

If I think about the values exercise that companies often do, and we’ve gone through things like this at company offsites, I think what we’ve missed in the past and is common for a lot of companies is you often start from aspirational values and you don’t often start by, “What do people actually do?” I think that exercise is something that’s quite useful to understand, “Okay, what are our values based on what we actually do and how far apart is that from our aspirational values?” So when you get to the point where you want to codify your values as a company, and each company might decide at a sudden scale it’s time to codify the values, making sure that the aspirational values aren’t too far apart from what actually the company does today.

Randy Wootton (14:20):

Yeah, I think that’s great. Often the value exercise can turn into a Dilbert routine and you have a set of values, you put them on a poster on the side of the wall, and say, “Hey, those are our company values.” There is a great article in HBR, Harvard Business Review, and I can’t remember the name of it, but it talks about this, be careful about taking on the value exercise because there are these actual values, these expressed values, that you have to be able to acknowledge and name as much as you then want to articulate new values, and, to your point, the aspirational values introduce those over time. I think company has values whether or not they are labeled, and so being clear-eyed about what they are and then trying to reinforce moving in a different direction that people are committed to and then how do you set up… Maybe this is a question for you is how do you set up the reinforcement in terms of behavior and coaching and rituals to… Do you have a set of… I mean, can you tell me what your values are? Are they four things that you espouse, and then how do you create the rituals to reinforce them?

Michelle Valentine (15:27):

Well, I remember going through this shift at Airtable, actually, where we had very organic and innate values that came from just working with a very craft-minded team. Airtable as a product is very complex to build. For those that aren’t familiar, it’s a database that really presents itself like a spreadsheet, and so it’s a very powerful tool and a very difficult product to build from day one. You can’t release little feature by little feature. When you build it, you have to build the whole thing.

(15:58):

There was this culture of simmering where you’d actually sit and be really thoughtful with a craft and simmer. This was something that in the early days we used a lot, and then at a certain point that didn’t serve us very well because you needed to act with urgency and you needed to actually go to market with a product that you’ve built. There was a clear shift where we went from often in a conversation to say, “Hmm, let’s simmer on that or let’s think about it a little bit.” To like, “Okay, no, we need to make a decision and act with urgency.” That was a very clear shift that happened when we were about I think 100, 150 people where that framework just wasn’t serving us well anymore and the team had to really change the way in which we use that language because it ended up holding us back.

Randy Wootton (16:51):

What were the rituals that you were introduced or that you introduced to move from simmer to act with urgencies?

Michelle Valentine (17:01):

I think the biggest thing that I would say the CEO, how he did, was to stop using it himself and it was no longer in the vocabulary of every day. I think it’s also pointing out to the team that, “Hey, we need to change.” Often the analogy that Silicon Valley founders use is, “Hey, we’re building this plane as we’re flying. Things are going to change while we’re in flight and change is okay.” Something that I’ve learned through seeing companies go through a lot of changes is the biggest thing that holds people back from being able to change is this fear of loss that, “Hey, we’re going to lose something very precious that was very special to our culture.” There’s fear of losing that thing, and it’s important to remind people that change at a startup is very normal and there’s so much more to be gained and company culture is a living and breathing thing that evolves when you’re moving so quickly and when you’re growing from such a small base.

Randy Wootton (17:57):

Yeah. One of the things I found coming into Maxio, which is the mashup of two companies, SaaSOptics and Chargify, who both had been very successful in their own right for 12 years each, was they had ingrained ways of doing things and they were different. I mean, you almost couldn’t find two more different cultures than how things were done in terms of product release at SaaSOptics versus how they were done in Chargify, the way they interacted with each other, how they thought about go to market, management systems, just radically different. One of the things we had to confront was when I came on board in 2022, I was a Maxio employee and my stated mission was to bring the two companies together and do the best we could to build a great company. It was to honor the history and the values of each, but we couldn’t have competing values.

(18:44):

I think that was something we had to work through, and, to your point, I think what you found was the old guard, they weren’t being resistant just to resist, but I do think it was the sense of this fear of loss of what made them special as Chargify or SaaSOptics and how was it going to be consumed into this new board, Maxio? We did end up with some attrition so that by year two with the attrition and the hiring behind, we ended up with more people that were Maxio first than legacy SaaSOptics or Chargify. I think once you hit that tipping point, now you have a group of people say, “Hey, I only know what Maxio is.” It was really important for us to introduce a set of values, we call them HYPE, honest and open, your input matters, passion for progress, and expect excellence. Going to the point about rituals, one thing I like about it is it’s memorable. A lot of companies, you have your values and you’re like, “I don’t know. There are like 10 of them. I can’t remember them.” Having an acronym makes it easy.

(19:38):

Number two is we use every single all-hands every single month. There’s a winner for the HYPE Awards, and then we introduce the year-end… The person who had the most honest and open. The other thing we use Bonusly. I don’t know if you have heard of Bonusly. It’s this wonderful tool where you’re able to give basically token points for people catching them being great. I don’t know, a couple of bucks, but then they go into their Bonusly bank account and they can use it to buy swag, they can use it to buy gift certificates, and so rather than giving someone, “Oh, here’s a Maxio T-shirt.” Instead, it’s like, “Here’s some Bonusly points. If you’d like to buy the Maxio T-shirt, then please do.” But every employee has a certain number of bonus points they refresh every month, so if you don’t use them, you lose them, and when you give them, you have to call out someone along those dimensions, one of those four dimensions, honest and open, your input matters, passion for progress, and expect excellence. It’s just a constant remindering and it’s peer acknowledged feedback versus executives.

(20:42):

I think if you were to ask anyone across Maxio, they would know the values, HYPE, at least I hope they would know what the letters stood for. I’m not 100% sure if people would be able to distinguish between passion for progress and expect excellence, for example, so there might be some evolution of that we need to do over time, but I think the most important thing was we had this group that came together, they determined these were going to be the values, they were reflective of I think the expressed values of both companies, we looked for some commonality, and at the same time they set forward some aspirational values. That’s great.

Michelle Valentine (21:20):

I have a question.

Randy Wootton (21:21):

You go ahead. Mm-hmm.

Michelle Valentine (21:22):

I have a question for you about your fourth value around how to build that effective executive team. As someone who has merged two companies together, Chargify and SaaSOptics, how do you think about whether to discuss problems out in the open in a group versus multiple one-on-ones? Traditionally, if you’re more in an IC or manager seat, how you effectively get things done is to get buy-in from people individually and then bring it up in a group setting, so have multiple one-on-ones and then bring the problem and proposed solution in a group setting. There’s this other school of thought. This is more like Jensen at Nvidia. I know a few other executives say, “I don’t have one-on-ones meetings. I do everything in a group setting, and so all of my execs hear all of the issues out in the open and that’s more effective, and then you get into a habit of being able to have those tough problems with the visibility of everyone on the executive team.” I’m curious, when you’ve merged the two companies, how did you think about having and solving problems in one-on-ones versus in a group?

Randy Wootton (22:30):

Well, I think part of it comes down to what is your rhythm of the business and how do you think about that first team, the executive team. Patrick Lencioni wrote about The Five Dysfunctions of a Team, and that first team… You got to hire people who are committed to the overall business results versus their functional, and that goes… I’ve turned over 50% of the executive team. Not that the other people weren’t able to do that, but just as you bring in new people, you want to be hiring for that inclination orientation that, “I am there to be part of the first team.” I think the other… Not radical transparency, but that whole theory, but I do think getting super clear about what your objectives are, what are the metrics that matter and the targets, and you’re just completely transparent about that. You’re transparent about that at all-hands so if things are trending red, you call it out and you say, “Hey, it’s red and here’s all the things we’re working on.”

(23:20):

We also use column plans on the page, which are effectively like 90-day plans, and so then every executive… We just got done with executive offsite last week. They go through their Q2 plan on the page and talk about what was red, yellow, green, what things they pushed, and share that they have to talk about, “I have this one slide, which is the summary, which is what went well, what were the lessons learned, where are you stuck, what are your asks.” They give this overview of what’s happened in their function, then they reflect on their scorecard and the plan on the page and they use that to tee up their next quarter, so the Q3 scorecard plan on the page. There’s a lot of conversations around, “Well, if I want to try to achieve this target for this metric, here’s what I need to get done by myself and here’s what I need from you.”

(24:10):

There’s the what I call handshake metrics, like if you’re going to build up your pipeline, that’s being dependent upon marketing sales, and for us our customer success team does the expansion sales and then our rev ops team. All four of those people need to be kind of aligned and talk about the relative trade-offs that need to be made, so I think there’s a combination of what is success broadly across the organization that gets reduced down to the corporate scorecard, what is each individual taking from that to drive forward with regards to what happens in private versus how do we escalate so that we have good conversations? We use what I was describing before, that big rocks construct. Here’s a big rock, we’re going to spend time and talk about it. Pricing, for example, for us is one of the things we’ve been working on. Do we have it right? No, and lots of people can opine on it, but I think that’s where we try to take on the problems.

(25:07):

What I find is interesting, Michelle, and I’d love your perspective on this because this actually ties in with building an effective executive team, number four of the secrets of success, is you have people in there… For example, if you’re thinking about pricing, is the head of HR going to really be able to dig in on that? Maybe not, but having him or her as part of the conversation allows them to continue to build context around what’s going on in the business. Similarly, they may be the one that’s leading the [inaudible 00:25:37] program. Everyone has a point of view, they may want to engage on that, what’s working, what’s not on that, but that can be done in a public way where everyone’s participating, so I think how do you have your team engaged depends on the topic and how many people it affects.

Michelle Valentine (25:56):

I’m with you on that one.

Randy Wootton (25:59):

All right. Well, we’ve talked about a couple. I think when we were… The last one, unless you had any other one you wanted to call out, was investing in your tribe. In our pre-brief, I thought that you had this really interesting point of view on how do you build your own skills as a CEO and what are the three things that you’re really focused on in terms of what you do individually versus what you look for a mentor for or what you’re looking for feedback from a peer group. Can you talk a little bit about those three things and we’ll dig in?

Michelle Valentine (26:27):

Yeah. I would say the biggest support network that I’ve had is through a lot of other founders, and I often meet them through our investors, and creating space to swap notes on best practices, to zoom out with similar stage companies has been incredibly valuable. I think the few themes that I notice as a CEO is investing in their personal growth that seems to be productive really comes down to for me three things. One is the best CEOs tend to be right a lot, and the only way to do that is to invest in building your intuition. In our last conversation, Randy, you and I talked about how to quantify how confident you are about something. This could be like, “I have low epistemic confidence, I’m medium, I have high epistemic confidence.” Then you could even start prescribing a percentage on that. It really is so subjective. It’s for yourself, so you know what that means. It’s really hard to say is Michelle’s 80% confidence similar to Randy’s 80% confidence? It’s probably quite different, so it really is for yourself, but I find the best founders tend to be right a lot and the only way that I’ve been able to figure out how to be more like them is to build up my own intuition and quantify how I’m feeling.

Randy Wootton (27:47):

Let me ask you a question because I do think there’s this interesting… I remember when I first got promoted to CEO, it was like a battlefield promotion and I felt like a total imposter and didn’t know what was going on. Had been to business school, I don’t know, 20 years earlier and I felt like I didn’t have the pattern matching skill. Now this is my third time CEO, I’ve been on a couple of boards, I’ve participated, but it’s like 10 years. I was a chief strategy officer in another company, and I feel like I’ve built more confidence in my, what you would describe, intuition, but it’s come from pattern matching. It’s come from having seen it a couple of times. How do you think… I know I’m putting you on the spot, but how do you build your intuition without having that experience, without seeing things play out? Maybe, again, it’s your background as an investor and you’re tuned for the pattern matching a little bit, but what do you do to build your intuition so you know to trust your intuition?

Michelle Valentine (28:43):

It comes down to being curious because you’re right, I think a lot of the ability to diagnose problems, to spot where the business could be operating better comes from pattern matching, and you need a lot of curiosity to accelerate getting those inputs so that you can be a better output. There are ways to do that without running your own company, you’re right. Being in VC is one. I think the privilege of working with many incredible founders when I was at Index Ventures and going to their board meetings, working closely with the CEOs, that’s invaluable. I think in particular what comes to mind is watching Alex Wang at Scale AI really operate the business when they were less than 50 people and scaling to where they are now, a $10+ billion company. It’s been absolutely phenomenal, and even just those few years where I got to work alongside Scale and looking at what makes them a great business is their relentless focus on execution. It was a crowded and competitive space, and they really have won.

(29:45):

Being able to work with many companies like that in VC does help. That said, if you’re a founder and CEO that hasn’t had that opportunity, I do think reading a lot, not just podcasts and hearing other great CEOs speak, but books like the one you mentioned, Five Dysfunctions of a Team, those ones I think really help hone your input so that your output is more valuable. The other thing that I think about a lot comes from one of the Brex co-founders, which is how do you be that CEO that can scale scale with a company? Because it’s not just about seeing the movie once or twice before. It’s like if you hit that rocket ship, you’re probably going to see things you’ve never seen before, and so how do you scale as a CEO through that?

(30:29):

The key that the Brex team found was the people that could succeed and scale the most were the people that could reinvent themselves multiple times in their career. For them, the question then became, “How many times have you had to reinvent yourself in your career and change and adapt to that change?” I really like that framing. It resonates with more personal life concept that I have for myself, which is, “How can I live many lives in one?” One of the great privileges of this life of running Anrok with this team is that I think even within Anrok, we’re living many lives in one. The company is constantly changing. We’re constantly working with different companies where we have to think a little bit differently, we need to operate a little bit differently, and our roles change so much. To me, a good life is often about how many lives can you live in one.

Randy Wootton (31:21):

That is a great quote. I often tell people that one of my principles is this, I want to operate in the edge of my own ignorance. If I’m constantly doing that, then I’m building a broader understanding of things, and that goes through books and conversations, groups that you can join. I’ve been a member of Vistage. I know people out there do EO or YPO or, to your point, through your… But it’s just about putting yourself out there to have conversations with people, challenge assumptions. It’s like I have a point of view, but loosely held. That’s great. That’s the building your intuition and a couple ideas, suggestions for people to think about that. Get in a book club. We have a book club at Maxio. I’ve had book clubs at every company I’ve been part of.

(32:06):

You don’t know where the ideas are going to come from, so how do you create these almost orthogonal experiences to open the subconscious? It’s the chronos versus kairos time. I was just talking to one of the people on the team, and I ride bikes and I talk about bikes and running or any sport could be this way, really, it’s moving meditation. You’re not actually solving the problem that’s right in front of you. You’re just letting your subconscious work through it and you’re cycling through this… Maybe this is what your third point was, which you didn’t call out but I’m going to call it out for you, is make time for reflection, is where do you create space for that so that the subconscious can come out, so that you have some of these ideas evolving? I find my best ideas are often on a bike ride, and I got to stop and write it down on my phone so I don’t forget. But how do you think about the make room for reflection when you’re living many lives, you have all these demands? Do you have a routine you do on a daily basis or a weekly basis or what does that look like for you?

Michelle Valentine (33:08):

It comes in a few different flavors. I think one, yes, I think for me it’s swimming versus for you it’s biking. I often have great ideas by the pool and I have no pen and paper when I’m there. My workout is totally destroyed because I’m trying to remember this one thing lap after lap to make sure I don’t forget. What I do in a more structured way is two things. One, I have a running note that I try to do at least once a week. I borrowed this from Eric Yuan at Zoom where he purports to do this every day, which is write down one to three things that you could have done better. That’s really to give yourself a very fast feedback loop and reflect, “Oh, in that meeting I could have presented this tough question in a more egalitarian or collaborative way or I could have asked a question in a different way that would’ve saved me so much more time in this negotiation with this person.” So really making sure I’m updating that running note thread on my phone at least once a week. I used to do this on my commute to really think about what could I have done differently and grow faster.

(34:16):

Another way that I make room for reflection is through meditation, where realistically I’m only meditating for 10% of the time and the 90% of the time it’s really a time where random thoughts come into my head and it’s usually fixated on a few problems at work that I’m thinking about, but it ends up being productive. Those 10 minutes, those 12 minutes where I’ve sat down and have made that time, I rarely do at any other time and so good thoughts and ideas come to the fore and hopefully I get at least 10 breaths without thinking anything and I feel like I’ve succeeded in my meditation. But if I also come out with a few ideas from that meditation about Anrok, that’s also a success too.

Randy Wootton (34:58):

Mm-hmm. That’s great. Yeah, I’ve tried meditation over the years, many different types and forms. I often find either I fall asleep or I end up not being let go of the thought, whatever’s popped in my head, just to get back to whatever the mantra is. Maybe I’ll try that again and just be more kind to myself and let it be just a time to have some more reflection. Well, that’s great. Well, Michelle, we have time for probably one more, which I think is in line with your diagnose before you deploy. How do you think about that as a skill versus some of the other things we were talking about, establishing a winning strategy, setting up operational structures and contexts? Is there something nuanced around this idea of diagnose before you deploy?

Michelle Valentine (35:43):

Yes. It actually comes from my investing days where I think an underrated skill is the ability to take many data points and synthesize. This does roll up to this creating the right winning strategy. I do think diagnosing the problem that you’re solving for and is this the right problem to even solve and write a strategy for is the precursor, I think, to maybe your number two. The key, going back to the investor point, to diagnose well is the ability to synthesize. Often I think the role of the CEO in a meeting is to inflect the trajectory of the meeting and often ask, “Hey, we’re spending… We have 30 minutes set aside to solve this one thing, but is this even the right question to ask or is this problem even worth solving? Maybe we should get the time back.” This diagnosis before you deploy all the resources I think is important to make sure you’re allocating your resources and capital efficiently.

Randy Wootton (36:44):

Right, and it supports your first point as well, building your intuition to understand is this worth the time of the people in the room or of you yourself spending time on this specific problem versus something else. I don’t don’t know what book it was in, but it was this idea of run to the thing that you’re avoiding because that’s probably the biggest and hairiest problem that you need to address versus do the thing that you feel comfortable. I think as a CEO in particular, that is… I find… Meeting with customers, meeting with prospects, creating space for all of that, I love doing it. I often find that, “Oh, I can find 15 things I could do other than that because it’s hard to get them on the phone or try to set up a meeting.” But when it comes down to it, that’s probably the most important thing for me to be spending time and energy on. How do you adjust your schedule and change your energy around that I think is great.

(37:40):

The last point, I’d offer a story which I love. I was chief of staff at Microsoft for one of the top 14 guys, guy named Bill Veghte. He was brilliant, ran Windows and online services, and by virtue of being his chief of staff, I had entry into some of these meetings that were way above my pay grade, but at the time Steve Ballmer was CEO and he’s sitting around this room [inaudible 00:38:02] 40 executives around the table and all their hangers-on, their entourages were on the side. I was in the back row with the little people and he’d say, “Randy, your objective in this meeting is to listen to Steve Ballmer really carefully and try to anticipate what is the question he’s going to ask about that business, so whatever they’re going through, otherwise you’re wasting your time being in this room. I know you got to be here because you got to capture all these things, but if you can anticipate where Steve is going to pry or poke, you will be building your skill as an executive.”

(38:36):

I think that opportunity to be very thoughtful about business, using every opportunity you have when you work with other smart people to see how they think about a business and building your skill and intuition, is probably the most important thing. To your point around a CEO, you got to be right more than you’re wrong, and the way you get there is through pattern matching, it’s through investing in yourself, it’s operating in the edge of your own ignorance, it’s working with a bunch of people to help selfishly share and then be selfish and take in terms of time. To that point, thank you, Michelle, for sharing your time with me and your insights. I’ve walked away with 40 pages of notes, three things I want to apply tomorrow, and I’m very grateful.

Michelle Valentine (39:22):

Likewise. Thanks, Randy.