Hello everyone, and welcome to another episode of The Operations Room, a podcast for CEOs.

I am Brandon Mensing, a joined by my lovely coach, Bethany Ayres.

How are things going, Bethany?

You know how December is really hard and you have to do so much work and you have all of the parties, but everybody's like, but don't worry, it'll all be over.

And then you can breathe out in January.

And then if you run the fiscal year or even one month off, that's a lie because January is twice as hard as December.

Is that true?

I think it is.

Or at least that's where I am.

There's such incredibly intense months and then there's January.

And also just the way that we're running it this year like so I'm just back from four days in Manchester.

The Tuesday was our monthly go to market meeting and kind of quarterly planning session.

I don't know if I've mentioned this, but so I'm also running the account management team as maternity cover for the next year.

And I.

You briefly mentioned this.

Yes, right.

All things to all people.

That's Bethany.

If that's me, that isn't that the CEO thing, like, you know, all the different roles that you can.

Yeah.

The Swiss Army knife of talent.

That means that you can be slotted into anything on top of your other jobs.

I guess what's exciting about that is that you're hitting all the levels of the business, right, is like functional, practical all the way through the strategic.

Yeah.

But then next week I'm luckily at home.

The next week is planning for peak kickoff sales, kick off pro serve, kick off all the content production next week and then the following week back in Manchester for all of those kick offs.

Tuesday, Wednesday, Thursday, get home Thursday night, fly to Jaipur, Friday morning, and then in Jaipur for a week doing kick off.

So that includes like engineering and product kick off.

So that is a tremendous amount of planning and kind of kicking things off for 2025.

So and usually the CEO, you're so intimately involved in all these kick offs.

I'm looking forward to February.

February is when I can read that.

But it was an interesting QPR and strategy session that I thought would be worth talking about.

I was responsible for running the QB R and the Exac off site strategy session and I was really stressed going into it because I felt underprepared and I didn't know what kind of format was work and I didn't know how they were going to go.

So the QPR, just for a bit of background, is a reboot with the wider teams we haven't had.

We've been doing Kubernetes just as an executive and that's been working well and this is the first time we've added the next layer like their direct reports in.

And then this is my first exec offsite two to run.

And first of all, I realized that I'm I much prefer spontaneity than structure.

Surprise, surprise.

I don't know if this is the first time we've realized this about me.

I think has been the consistent revelation over the course of the podcast.

But I guess it's just like you think about a CEO, they're all about structure and process and blah, blah, blah.

And I'm like the antithesis of that kind of code, despite being a Swiss Army knife, is able to do whatever role I need to do.

So we had broad agenda items, but way more relaxed and had a huge amount of preparation.

So like for the strategy day, we probably had 150, 200 slides slash pages to read over a week, questions to think about context.

But if you think about it, it's, you know, across all of the different departments, it's not actually that many slides per department, but everybody having the context of the goals, the challenges, the must dos, what's going well, what's not going well in each of the departments and the interconnects.

We were able to go in and be very much less structured and we kind of started with problem number one and then let it just be an open conversation.

And it was probably one of the most effective conversations we've ever had.

Had some amazing insights come out of it.

And it also naturally concluded at about an hour 45.

I feel like this is resolved.

We're done.

Then we knew what our next topic was.

Took quite a big break because we had to do some other stuff and I regrouped with everybody having that time to think.

And then the next topic was covered in that same kind of time frame.

Naturally concluded as we did our final one.

And the final one was okay.

So because it wasn't like such a totally exhausting day, we were able to have much better conversations around the Oscars and like properly, rather than it being the rush at the end.

People's brains were still active.

And so I was trying to reflect on what made it work well.

And I think it was actually the fact that we're a highly functioning and performant team at the moment.

That means that I don't think the structure matters.

I think whatever structure it was would have worked.

And also a lot of it was around how do we work better, how do we solve the problems together?

How does everybody contribute to the overarching functioning of the company rather than siloed?

And that was really it felt really good.

I guess I found that the really highly structured ones don't work.

So it was a bit of a gamble.

So now of course, I'm like, How do I do it again?

Well, we get to the.

Quarterly versions of all of this.

Why do you think the team was in a good place, do you think, to have high quality conversations?

Because I'm an amazing leader.

Part of it, I think, is because of this, the operating model or the cadence that I've spoken about, where we're seeing each other twice a week.

We're able to bond and build trust through that regular contact surfacing issues.

So not letting things slide.

It's like I do a lot of face reading.

And so when I see somebody whose face is like the micro second of a grimace or an eye roll, I don't let it pass.

And I don't say you've just rolled her eyes because that's, you know.

But I'll just say, it looks like you have an issue with that.

What are you thinking?

And then we let it come out until they're like no grimaces or eye rolls and things have surfaced.

So that is working.

Encouraging more communication between teams.

Or like you two are clearly not speaking enough if these are surprises that are coming out in the meeting.

Figure out how you're going to communicate together.

So there's a lot more interconnect one on ones between team members when it comes becomes obvious that people are not talking the way they should.

And then having a bit of a laugh like being okay with some joking, a little bit of that, the levity of it.

And actually something I've done in the last two days and I don't know, I mean, I have to ask people if it's coming across genuine and genuine or not.

Like for me, it is genuine.

Is my finishing on a high but like reflecting on these been some conversations that are difficult?

This person might be feeling like they're being quite beaten up, but the fact that they're being beaten up is because of how far we've progressed that we're even able to have that conversation versus where we were before.

Let's take a moment to reflect on how much we've achieved and therefore what's going forward.

And also like calling out good things that have happened and recognizing those good things in the meeting.

So it's like reinforcing the good behaviors or the good ideas or the good connections between us.

We have got a great topic for today, which is how do you implement the first team concept?

We have an amazing guest for this, which is Cassie Young.

She's the general partner at Primary Venture Partners and a seasoned S.R.O.

slash chief customer officer.

So maybe first off, your definition of first team.

The most senior team that you are a part of is your first team.

And so as an executive, it's the exact team that for your direct reports, it's that team you like that functional team.

And what that means is that you put your first team ahead of your other teams.

So it's if you're on the exac how do you solve the business's problems and have your team as your department or your function as resource to solve the company's problems rather than viewing it as you're going into exact team meetings to represent your team.

So first team really is prioritizing your peer level team.

And in this case, for us, that's the leadership or executive team.

And the reason why, as opposed to your direct reports and the reason why that's useful is for my collective leadership team to come together to solve the company's problems, fundamentally working together to make that happen as opposed to representing your functional unit.

So I guess some of the challenges in making this come alive for companies.

The first one is conflicting loyalty, which is they're loyal to their direct reports, they're loyal to their function.

That's how they've grown up in terms of their lineage within marketing or sales or whatever.

And now they're being presented with this idea that they should be treating and prioritizing their peer level team, the leadership team, as their number one priority as opposed to their function now.

And they have that kind of conflicting feeling of loyalty.

So what do you do with that?

I think it's around how you mature as a leader, and it's actually something that you need to learn to progress to the next level.

So, you know, as an individual contributor, the first step is being directed by somebody else.

The second step is directing yourself.

Then you have the ability as a manager to direct a team and then as a senior manager or director, it's directing multiple teams.

Then you get to the VP level.

It's not just running a function, it's looking across the teams and so like representing your team, but in the context of the rest of the organization.

So like not having a victim mentality, you know, rather than just saying, well, marketing gives us shit leads, you work with marketing to get the leads that you want.

And that's a real mind shift change.

But that's, I think, still representing your team but not being a victim and being proactive.

And then when you move to the exac it's understanding that now that your team is the company, how does your team help the company rather than how does the company help your team?

So the other one of interest here was resistance to vulnerability, because what you need in that leadership team is for people to trust each other, to be able to bring forward challenges and problems in a very honest, authentic way, to allow the group to help each other figure out what the best thing to do is.

And the worst thing in the world is to have your marketing leader to come in and to obvious skate and to not share what is happening in terms of something that may not be good.

And they feel somehow that they can't trust the others in the group to share it and to feel like they may be viewed in a certain way, I suppose.

And I guess the question is, how do you create that trusting allow that vulnerability to occur where I'm sharing something within my function that is not good, but I need help and I'm happy to share that to the group and actually get the group to help me think it through.

So in the past, I would have thought about it as vulnerability of like, that's a problem in my area I need help with and then have the confidence to feel like, okay, I'm not going to lose my job because of it.

But often the things that are going to cause you to lose your job are your problems.

You know, like you've hired the wrong VP of growth and you're not delivering well.

And there are people issues and actually nobody else can solve that problem because it is something in your own area and in the first team it should be.

How do you broach the topic of it's not that your VP of growth is failing.

It's that the product has fallen behind the rest or the way the sales team is acting and selling is so against the brand.

Your brand is now been rubbished in the market and it's not.

How are you vulnerable around your area, but how do you raise topics that are impacting your team because of other areas and how do you have that rather than like pushing the product person under the bus?

How do you frame it in a way that is a problem that everybody needs to solve?

It kind of works both ways, isn't it, those your functional issues that are happening, but there's also things that you're saying within other functions.

Say you're very concerned about.

Yeah.

And then it comes down to how do you approach it in a way that doesn't freak everybody out and get super defensive so that you can have a good conversation around it.

Talk about resource allocation.

Talk about plans, talk about like what the other departments can do to help the one who's struggling.

And I think to be honest, Bethany, I feel like this topic is probably the single most difficult thing in any business is to have this happen.

You know, I mean, I've seen this over and over again where I've tried all sorts of things over time to put the group in a position where we can have these conversations in a healthy, constructive way.

But it is very difficult.

People fundamentally are very loathed to point out other people's potential issues.

Any things that you would think about as to how to facilitate this or to make this better over time.

So I think part of it at least.

For me is I'm often the one pointing it out in my current role because I can see and I'm looking holistically.

One of the things that I'm using to do this is the SAS flywheel idea.

Where have you seen this?

Where?

It's a line in a circle.

I talked about it actually around metrics for on the business event, but I use it a lot for basically like that customer journey.

So it's leads, opportunities, customers is the straight line and then the flywheel is where the customers you on board, the customers.

They're so happy that they buy more, renew, renew, buy more.

I'm never quite sure which order makes more sense.

And then you on board them.

They're happy and they keep spending.

And that's the SAS flywheel where the land and expand happens or they don't expand, but they're big enough at a point that you retain them.

And looking through that customer journey and seeing the pain points and like, you know, the pain point might be in support and the number of bugs that they're dealing with.

But then you can follow that journey through and see what is causing the issue.

So looking at it systemically and it's not rarely is it one person's mistake or issue.

It tends to be death by a thousand cuts.

And so you look at like, what are all the things that are contributing to that and therefore, what can we all do to make it better?

Yeah, I like that.

So it's more of a systemic view across the organization.

And to your point, a lot of issues are cross functional nature in some form.

It's not usually strictly a sales problem or marketing problem or a product problem.

It's certainly, as you said, across a broader spectrum and kind of walking that logic through, I guess, and also perhaps the data nuggets behind that allows it to be less people function focus and more of a collective problem for the group, I suppose.

And I guess the other part is the modeling, because if you're pointing it out, which as an example, you're modeling the ability for others to do the same in a constructive, useful fashion, which is we are having issues and if you're happy to point things out, then perhaps that's can have a knock on effect for the others in the group to feel comfortable to do the same thing.

And I guess the other point is you being in a position where you're rewarding that behavior, either in the meeting or after the meeting in terms of making people feel like they've done the right thing by having that discussion, doing it in a very constructive way.

And then equally, if people are not doing that, then making sure that you're having conversations around that to, I suspect 1 to 1 in that case to encourage that.

And then also just wanted to point out one thing in what you were saying around, it's not around specific people.

That's actually one of the lessons from the, you know, Wickman book Ethos Entrepreneurial Operating System.

Like I think my biggest takeaway from that book is that all problems are people problems.

You know, like genuinely, rather than trying to scaffold something around somebody who's incapable of doing their job.

Being able to have that conversation.

And so even if you're looking at the entire flywheel, you may notice that we have a skills gap, we have an experience gap.

We have somebody who, you know, it might be that actually that VP of Growth who's not delivering leads.

If marketing realized it, they would just change their VP of growth.

But if somebody else is realizing and pointing it out, then you have a conversation around are we being unfair, blah blah.

And the solution may be that you replace a VP of Growth, but that's a team conversation rather than like the marketing person having to be all by themselves realizing that somebody is underperforming, but they've just hired them and it took them eight months.

They don't want to fire them.

It's like, now you have to fire them.

No, that's a great point actually, because like the skill gap or capability gap or something's happening and be in a position to include that as part of the conversation makes obvious sense as well.

I guess the other one that I was thinking about that you pointed out some time back, and this is a slightly broader trust building kind of activity, I guess, which is something in the business that truly speaking, pulls a leadership team together to focus on something that really, really matters and to have that shared experience, a galvanizing experience where we're all in this together, we got to make this happen.

It's a bit extraordinary, but let's do it and let's make it happen.

And having that shared experience where you're working very closely, side by side with the leadership team can really make a difference.

A breakthrough, a difference in terms of the trust that you've actually built within that leadership team.

I think your example that you gave was fundraising, because fundraising is kind of a bit of a battle cry to the business and in particular the leadership team to pull themselves together to get the right metrics and getting on the road to talk to VCs around, you know, the business and why it's tremendously exciting and so on.

What do you make of that?

I do agree.

Like so often people view fundraising as a burden and a distraction, but instead they should view it as an opportunity to both build together as a team and grow as a team, but also get all the strategy questions out of the way and.

Like really properly think about your next 3 to 5 years when you're doing it.

So love it.

Let's park it here.

And let's move on to our conversation with Ms..

Cassie Young.

So the concept of first team or team number one, as is sometimes called, was made famous by Patrick, like Yoni, who wrote books like Five Dysfunctions of a Team and the Advantage, which are some of my favorite business, reads.

The central concept of it is that the more senior you become in an organization, the more important it is for you to embrace the reality that your first team is your team of peers.

Right.

So the most senior team that you sit on versus your functional swim lane or your direct reports.

So if you are the chief marketing officer of a B2B software company, your first team is most likely that cross-functional leadership team that you sit on with, the CFO and the CTO, etc., not your head of demand gen or head of brand.

And it sounds really obvious when people hear it just said that squarely out.

But people don't think about that often in sort of the day to day rhythms of their work.

And what happens when they don't embrace that is they fall victim to what I call the swim line trap.

And we can talk more about that later.

But the one thing I want to harp on with first team is it actually cascades the whole way down in the organization.

So the example I give people is if you're the chief customer officer, you probably have this team of lieutenants that report to you like your head of technical support and you're head of the CSM team and you're head of professional services.

They are your second team, right?

For all the reasons we just talked about.

But they are each other's first team because that's the most senior team that they sit on.

And time and time again, I find this is a really powerful message for up and coming directors in an organization because it's like the blame game or one function to the other, and they have to embrace the concept of team number one and first team as well.

My experience is I've looked at it in a slightly different way where maybe I haven't realized I was thinking about it in first team.

For me, if you get first team right, then you just don't have the politics because where the politics come in is my team is my identity is being a CMO.

And so what I care about more than anything is how do I promote my function?

And if you have everybody doing that, you get loads of politics.

Whereas if you view the success of the company as your job, you don't tend to backstab your colleagues.

That's right.

And I think like to bring that to life for a moment.

I always share this example of a board slide I unfortunately had to witness right where and I'm going to pick on marketing, but we can pick on some other functions later.

You know, the CMO had this slide in the board deck that was celebrating the fact that quarter over quarter they had double the number of closed one deals that were sourced by marketing, right?

So they said we went from 45% of closed one deal stores by marketing to 90%.

And this was this huge celebratory point.

But what was lost on that particular slide is that this was presented in the context of a board meeting where we discussed how the overall business had shrunk.

Okay.

So the business is shrinking and the marketing leader is in there celebrating the fact.

Right.

That more of the closed one deals were sourced by marketing.

The same thing happens though, like in product and engineering functions.

Everyone comes in and celebrates roadmap velocity and all the feature shift.

You know, we had an event in New York recently where the CTO speaker had this great line where she said, If it can't be sold, it doesn't matter.

And so for product and engineering, I'm like, if you don't have the corresponding data and adoption and monetization, right, it's the same trap.

But that's an A Your point on politics is also an interesting one because all of those books right by table group, they have a whole other definition of the world politics, right?

Where they say politics in the organization is actually when you change your message based on the audience.

Right.

And I think that actually does apply here as well to where there may be one message that you have in your functional lane.

Right.

And one different set of things that you're talking about in the management suite.

And so, one, it's I completely agree with you, it's putting the business above your functional result, but it's also that just consistency of messaging and how you're talking about things.

And I incidentally listened to a podcast, but it was with Shane Battier, who's an NBA player here in the States.

I'm a huge basketball fan.

He's a Duke Ellington, so I always love to look at that in leadership advice.

But they talked about this concept of playing for the front of the jersey, not the back, which I think was another really interesting way to think about the concept of first team, where you're not playing for your name, right?

You're playing for the company.

And I think that's just an easy way to explain the concept, particularly down the ranks as well.

The question on the mind of the CEO always is how do you do this?

How do you actually create a first team?

So if you have individuals that are functionally coming from that mindset of I'm the functional owner, I'm responsible for marketing, I care about my metrics of my team, and they're the most important thing to me.

And then you start trying to shift their mindset to a different space, i.e.

the first team in this case can maybe just walk us through a bit of the practicality of like, how do you make that happen for sure?

Well, the first thing I'll say to you is that I believe.

Eve that teams will never be aligned if their compensation plans are not.

And I think that's a very straightforward place to start.

And I'll walk you through like a very tangible example of this.

I was at a software company called Sales Group, and we went through this journey where the company grew faster than our technology would allow.

We had scaling problems, right?

Everything of that fold.

We brought in an outside CEO and really had to execute something of a turnaround strategy around customer churn, customer trust, etc..

What we said was, okay, there are functionally always going to be three things that matter most to us as a company, right?

The first is to grow our business naturally, and the metric we're going to choose for how we grow our business is exit.

RR Right, because that's the composite of new logos.

It's the composite of what we don't churn, right?

What we grow from expansion.

So number one was grow the business with exit error.

Number two was net promoter score, right?

Because we said we want to.

The second bucket of things is be a trusted partner.

Now, you could argue the merits of NPS as a metric all day long.

We had to focus on that because our NPS score was in the toilet.

After these scaling challenges, it was -26 to give you a sense of it, right?

So we needed its actual focus there.

And then the third for us was operating predictably and responsibly, right?

And for us that became a net burn target.

And then over time it evolved into an EBITDA target, right?

Once the business was cash flow positive.

Now, we had in every monthly all hands for years the same first slide that had those three buckets and those metrics.

So everyone was talking about that.

The numbers change from year to year, but the central principles did not.

Where this comes into first team and the management team was we change the executive bonus plans to say every executive has a 30% bonus that is driven by those three numbers.

You would not believe the behavioral change you see in our product organization.

That happens when suddenly the bonus is tied to Net Promoter score, right?

It's tied to exit RR It just drives alignment.

Now that is sort of the stick approach of how you go about it.

I also think there's a lot of just kind of qualitative changes that you can encourage of the team as well.

So for instance, I would say, you know, if you're an executive, you're probably doing one on ones with every single one of your functional direct reports every single week.

What's your cadence with your peers on the first team?

I don't think you need to be with them once a week, but at a minimum, I would expect you to meet with them once a month, right, that you're sitting down and getting aligned.

So I do think it's on everybody to give that team the same priority and weight that they would.

Right.

The people who report to them that they're sort of growing and fostering.

But I strongly believe that the fastest way to get there is to make sure that the incentives are extremely aligned.

I agree to the extent that whenever I join a company and I am presented with my bonus, I just like, Is this how everybody else on the leadership team is paid?

And if the answer is no, I said, Well, no, we're going to have to work on that.

I'm not going to join where we're not paid in the same way because it doesn't work otherwise.

And you're all pulling in different directions.

The other way that I've helped foster this team is to talk about it as it's an element of development and it's like you're almost not ready for the next one if you can't sync across the company and you can only think in your swim lane and that will keep you from actually getting promoted or retaining that top table role.

And that for me became very clear.

When you hear people talk about it's X's fault, like, you know, marketing won't do what I need marketing to do, piece won't do what I need to do, What can I do?

I am just here in sales and that is not a top team table mentality.

Your job is how do I fix upstream?

How do I fix downstream where a connected system, how do we fix this together?

And that is how you get promoted and stay promoted.

And I think one of the areas of pushback that I've had historically is that you all like a functional leader.

And I'm suggesting to them around this, you know, first team mindset, this is the attitude that we should have.

And their first reaction is, well, that's a whole bunch more activity in meetings that you're asking for that I don't have time for.

So when you have that kind of reaction, you know what I suggested back to that person, this example, this was kind of what Bethany had said, which is, you know, when you think about your career development, you think about the next step for yourself.

The next step literally, is you having to work on the business, not in the business.

And on the business means A, B and C, And if you have no experience doing that, it's going to make it that much more difficult for you to make that jump and to be successful when you make that jump.

So we have this back and forth and eventually we came to the right place.

But this question of pushback around a whole bigger swath of meetings, what do you do with that?

So maybe a two part answer.

I agree with everything YouTube said right around like fundamentally, the job changes when you're an executive.

And someone said to me many years ago that the more senior you become in an organization, the more all roles converge and your job is just people.

Management are running the business right, and you might do it over product that ends.

You might do it over sales and see what the jobs are all the same.

And that really resonated with me.

And one message I'll often say to up and comers is like, you have to choose if that's the path for you.

Right?

I think a lot of times people, they falsely conflate people management with leadership, right?

Like the only way I can be a leader in this organization is if I have a bigger team and I run the function.

That's actually not the job for everybody, right?

There are many other ways to be standout leaders at an organization and to contribute, and I think naming that for people is super important to being very real about what the job it's as you climb through the ranks, right?

Like everything is a people problem.

When you're running a large organization, Like that's your job, that's what you're doing all day long.

That said, Brendan, you know, to your point, I do think you have to be very disciplined in terms of meeting hygiene, right?

Challenging norms.

I feel like as I've been part of growing companies in the past, we've just had to commit ourselves to iterating and challenging the status quo, right.

Every couple of months on what we were doing.

So to give you an example, for the past life, we had a very tight quarterly business review process by every function.

And it just became like the preparation for the quarterly business reviews just became totally daunting and probably not the best use of time.

But we said, why don't we switch into more of kind of an Amazonian memo format, right?

To put that together, give a free read.

So I think there are ways that you can kind of shortcut or short circuit some of the meeting fatigue and prep, etc., that every organization just has to be very disciplined about saying like, is this an energy drain?

And if so, what small adjustments could we make to make that, you know, more accommodating or appealing to the participants?

So this is a challenge that I've recognized recently.

I'm trying to get people to communicate with more empathy to their listeners.

And what I don't mean is being kind or how are people going to feel, but what do people need to know to do their jobs better rather than sharing with people what I've been doing to justify why I have a job?

I think it's very well said.

It's really hard to make that transition and it's something like every meeting I'm just like, how do we get people to think about the information?

And it's amazing because we share so much information that nobody consumes it.

And then I go to a meeting and say something and half the room have no idea of like the one most important thing because it's hidden in all of the justification of jobs.

Have you figure out ways to make this happen?

I think it's really hard to your point, but one framing that I frequently think about many years ago, someone use this acronym and I was like, What's this acronym?

An acronym was Weafer or the what's in it for me?

I share that acronym now because I do think as you're working with different audiences, you have to approach it from the frame of what's in it for them, right?

Like they are thinking about it that way.

So to your point, it's not that you're coming to say, Hey, I need you to go do a ton of customer case studies, right?

Because we don't have a it's hey, your goal is the marketing team, right?

Is aligned.

Do you know ultimately the number of influence closed one deals more of these case studies are going to help us get it done time and time again.

We get that aspect, but it's really making it real for them based on their success metrics, which is why I think it becomes easier if everyone has the same success metrics, right?

So that you don't have to politic that message in different places, but you have to preempt the question and sort of see the so what for people when you're talking with them or making that ask of them.

I also just think there's a huge win to be had with just reinforce positive reinforcement when things work, right?

So I think it's like very frequent.

You know, you talk about customer feedback or problems or requests, but you know, oftentimes like customer wins are just thrown into a Slack channel and never really talked about like bringing a customer into regular all hands meetings, right?

Giving the engineering team one approach that worked really well for me in the past was to bring in the technical stakeholder from different customers and have them sit down with the spread teams who built the product that they implemented.

Because the engineers, like I was telling the CMO, is they didn't like necessarily really want to listen to what the CMO economic buyer had to say, but they loved getting the technical feedback right.

I like the API flexibility, so I think it's meeting kind of your internal stakeholders where they are right with positive reinforcement aligned to the goals can be a strong path as well.

When it comes to kind of cadences and the number of hours that you spend with your first team.

Can you give us a bit of a and around that in terms of on a weekly basis, monthly basis, quarterly basis?

Like what is a.

A good mixture of things, do you think?

Yeah.

So and I'm not going to claim to take credit for this.

I actually think a lot of my own learning on this came directly out of frameworks like those that are presented in the advantage and elsewhere.

Right.

But the general approach that I've seen worked really well.

As you know, you have your weekly leadership team meeting, right, which is usually probably minimum an hour and a half, right.

Kind of growing and scaling companies.

I really like this idea of once a quarter for a day.

You're taking that first team off site somewhere, right?

To wrestle some larger business plan discussion.

Right.

Or talk about what the operating plan for the back half of the year is going to look like, etc..

But I also like this idea of holding time once a month for ad hoc strategic topics that come up that can't wait until the next quarterly offsite.

The trick with that, going back to your previous question, Brandon, about needing fatigue is like, if you don't need the meeting, just cancel it.

Right.

Which I think people are often afraid to do.

But you hold the space, so it isn't like this crazy fire drill at the last minute to find 90 minutes.

And everyone's annoyed because you're disrupting their weekly workflow.

So I like the dedicated weekly meeting and I want to come back to that because I think the format and what's done there is really, really important.

This holding space once a month for an hour, hour and a half for a deeper dive topic, and then the quarterly data gather offsite and maybe once a year that's even longer right than the one that you're doing that for a longer period of time.

Now that's the full team together.

As I said earlier, there's also these monthly cadences around the table, right?

So if I'm the ero, I'm probably going to have another five or so meetings, right, with the other kind of key CEOs around the table just to make sure we're sort of building that report, etc..

And that monthly meeting is a good stopgap.

But I also think it's like great executives go way above and beyond that.

The quick comment I'll make just on the weekly cadence is I think a lot of times those meetings can just be highly dysfunctional, right.

Where it's sort of a free for all what the agenda is.

I do think there are some best practices that companies can follow around.

Okay.

We always start with the numbers, right?

Number one, because we're working on the business right at the end of the day.

It's amazing to me that I sometimes shadow leadership team meetings and I'm like, Where are the numbers again, this meeting, right?

We're not just here to talk about how we're feeling or what the weather is looking like.

So that's number one.

Number two is the CEO is the boss.

Right.

So how do you let the CEO set the agenda for any given week?

So in the past, I've like these approaches where, you know, the senior executives can propose topics, but ultimately the CEO curates the agenda from week to week around the places where they do or don't want to dig in.

I love that talk about the CEO being the boss and the agenda, because then also you're the boss of your functional lead and you're doing the same.

And that was one of the things that happened when I first became CEO and had basically all of the customer functions.

So so is marketing, sales, data science, customer success.

So we have like quite a few.

And then like my job became basically an events organizer.

I felt like I'm getting paid really a lot of money to organize meetings, but that is actually a large part of your job is to think about how to have good meetings and how to have meetings where people can talk and how you can get to the issues.

And it was just such a weird moment for me.

I also think it's like it's that and it's what's happening in those meetings is how you communicate, right?

And how you drive clarity for people.

Yeah, because when you think about it, you've got the 6 or 7 most expensive people in the company meeting on a weekly basis.

And if that meeting is a shit show, you're kind of like wasting that money, number one.

And the number two, the amplification.

What comes out of that meeting, if it's been a terrible meeting and it's divisive or whatever, the impact on the rest of the company is, ripple effect is also potentially quite negative as well.

I completely agree.

And I think to that point, Brendan, like it is worthwhile at the end of executive meetings, particularly like the meatier monthly meetings or the quarterlies, but you can certainly do it with the week is aligning on what you are or are not going to cascade like what is off limits?

And if it's not off limits, then you should feel empowered to go into your functional lane and cascade those mitigations.

I think it's ridiculously important when you're going offsite because invariably when you take seven really expensive senior leaders of the company offsite, you know what's happening on the ground, right?

Everyone's like, what's going on?

What are they talking about is going to be layoffs are going to be this.

So I do think being as open as possible with that is great.

And you can really prioritize doing that week to week.

We do that because I've noticed that there's an inconsistency of ability to communicate or an inconsistency of what is communicated.

And so I introduced that, but I'm not sure we still always take the time.

Like sometimes you have meetings.

Because we meet twice a week.

It's set for an hour.

Sometimes it's a full hour.

But like, as you said, sometimes it's 15 minutes because all we have is 15 minutes worth of stuff.

But we have the two.

And sometimes it's really clear that we need to talk about what we cascade.

And other times it's like we just talked about random shit.

Like, do we need to cascade this or not?

And at first I was like, no, there's nothing to cascade.

And it's like, No, that's not the point.

It's not what should we it's what shouldn't we?

And so it's like we just talked about random things.

All of that is fine to share.

If you think it's relevant for your team, it's much more important to identify the things that you actively shouldn't share.

And then that frees up people to share more, because I think the default is with fear, they share less.

I think related to that and your point about there's just such varying degrees of comfort with how people communicate, I think leaders almost have to force themselves into accountability.

So I mentioned earlier when I was on the operating side, I sent this note every Monday night for years and years and years.

And like I couldn't.

Not do that note.

So it just held me accountable.

And I wrote the note over the course of the week.

Okay, what do I want to include?

I came out of the leadership meeting today.

What am I going to put it from that in terms of takeaways in this note versus what am I not?

My functional leaders knew they could send me stuff that they wanted in there, but it was just this forcing function for making sure I was communicating so it doesn't have to be once a week.

It could be, Hey, look, I'm going to have a monthly engineering all hands and these are the things I'm always going to commit to talking about in that all hands.

Meeting, right, is find what works for you.

But I think you have to have some degree of accountability in like what the mechanism is for how and when you share.

What do you do?

In the case of the functional leader, that is obvious skating.

Yeah.

I mean, I think that really healthy teams have healthy conflict and it starts with the CEO.

Do I mean in terms of making people comfortable, challenging each other very directly.

And so I think what becomes hard is if you're in one of those meetings where silently everybody knows you're sort of an elephant in the room of what's going on and the CEO isn't willing to directly challenge.

No one around the table is going to do it right.

It starts it's all like the classic norming of the team.

And this is why my earlier point about building trust, right, and kind of going out of your way to do that conflict is so much easier, right, when you have that trust in the first place because you can assume positive intent versus if you don't have that right, everything kind of goes haywire.

And so I do think it's how do you get into the company rhythms of just naming it in the meeting?

Going back to that earlier definition that I shared around politics, right, of saying different things to different audiences, this is where that shows up.

It's like we can't talk about it in a group format.

But then I'm going to go back and have a sidebar conversation with my CTO about the CMO.

my gosh, what the hell are they doing all day long?

And there's a polite and constructive way to do it and frame it right in the meeting.

But I do think really strong companies kind of have that public display of challenge questioning, etc., But it's in the name of doing what's best for the business.

I just thought it'd be interesting to take the change topic a little bit back to the first team.

And are there universal skills that make for a great executive that we could almost just then lift as a leadership framework that we use when evaluating ourselves and our other leaders?

Absolutely.

So one is like, as we've just talked about analogy, I'm like embracing this leadership mentality, right?

Where you do put your team number one first, but the second is just strong pencil command and fluency.

And I think this is unfortunately very often lacking in senior executives.

And so what do I mean by that?

If you're a chief customer officer, you need to be well-versed in like the margin drivers of the business.

Right?

Because so much of what you're doing is is servicing the customers.

Right?

And you really have to understand what follows above the line, below the line and how you help advance the ball on that.

And I think a lot of leaders have a hard time connecting their day to day work to the top and bottom lines of the company.

So I think that's a good place to start.

And, you know, people frequently say to me, well, you know, how do I go about doing that?

I didn't go to business school.

I didn't do X, Y or Z.

My number one suggestion to them is take your CFO to lunch.

This is like a branded campaign.

I think I want to launch for 2025 or when I say CFO, it could be the VP of FCPA takes someone in the finance function at lunch because let's be honest, no one's inviting our finance colleagues to lunch right there in the bottom of the invite list, sitting down and saying, Hey, could you walk me top to bottom through our companies now?

And the things that you're thinking about in advance of the next minute.

The finance leaders love it when functional people come and ask them that question.

So I think that's a really easy so I think first team piano fluency, I think the two other things that I'll highlight, one is just a command for what's going on in the market.

So this is going to sound crazy, but I frequently say to people like, do you read the news?

Right.

Do you have a point of view on what's going on?

Right.

Particularly in this era of AI.

Right.

It's you have to have a perspective and you don't need to read that much news.

But, you know, I always say, look, right now I invest in software companies.

Many of them are A.I.

native companies at this point.

There is a lot of industry chatter around is everybody just experimenting with A.I.

software are going to churn off of it.

So if I'm talking to a C.

S leader, I want them to come in with the point of view on what's going on in the market, right.

And how they're thinking about that.

And the final thing I'll mention and this this basically going back to that word you and I, that I do think is is more acute with women than men is just having a strategic network and making the space for that outside of your company.

You may not want to copy verbatim what another business is doing, but every time I talk to leaders of other companies, they say something that just get my gears turning a little bit differently.

Right.

And I think this is particularly important in the era of remote work.

I understand remote work can work really well for various companies, but if you're not going to be in an office every day, you have to work that much harder, right at how am I going to cultivate the strategic network if I'm not hosting people at the office, if I'm not meeting with clients in person regularly?

So I just think people have to be deliberate about it, but that's probably at risk of gross oversimplification.

But I think if you do those four things really, really well, right, In addition to the brass tacks stuff we talked about, about like communicating, etc., which I think comes back, I think that's a recipe for success.

But I would put that communication stuff in that first team bucket is kind of, you know, just being part and parcel with it.

So speaking of seeing things in the news, did you see the video from the Nvidia CEO how he has 60 direct reports, No one to ones.

I would just love to hear your thoughts on that.

That was a talk of our office right when we saw that.

And you probably also saw that was right around the time of the whole founder mode article that came out.

And I thought the founder a piece.

The interesting challenge that was put out there is our founders is going to use this as a convenient excuse to do whatever they want.

And I think my take is 100%.

We had a line when I was at the operating site where we sometimes call things founder itis, right where they were just kind of happening in the business.

But don't miss here.

I think founders are incredible.

Right?

And this really breakout category, defining companies are who they are because of that founder DNA right off of what those founders do.

I think that is probably not aligned with my personal approach about how it goes about clearly they're doing something right and it's working well for them.

I just read a statistic on the number of video employees who are billionaires at this point, and it's absolutely insane in terms of the enterprise value that they've built.

But I do think that is probably like an outlier exception case and it gets dangerous, right when we're out in the news talking about these amazingly highly performant companies and how they do work because the vast majority of companies can't operate that way.

Right.

So I think it's you have to have the creative license as a founder and CEO of what is going to work best for your company.

But as you are getting started on that journey, I don't think you need to recreate the wheel.

I think there are some tried and true best practices that you can throw up in flames, right, if they're not working for you.

But I think orienting my fear is people see these crazy one off outliers.

They're like, well, I'm going to go do it that way.

But fundamentally, that's like a 1 in 1,000,000 company, right?

So getting back to your original fluency comment, you know, it's interesting.

I just think about this in my head as you were speaking about when I joined companies as the CEO, I have like a real interest in piano fluency and being able to partner with the finance leader to ensure that we have forecast models that make sense and so on.

And I end up spending a disproportionate amount of my time with that finance leader to really understand the models at a certain level of detail and to be able to communicate that effectively to investors or for fundraising or for the company or for the other leaders or whatever.

So I end up playing this weird proxy role, like filling that gap or showing that hole in a way where the finance leader can't quite do it.

So I step in as the communicator, but I have more of the understanding of the business in totality as opposed to the finance leader.

So I end up being that person to represent, I guess in some sense.

But I also feel like I maybe it's a bit of like what you said, Bethany, which is I'm filling a hole and legitimately the other functional leaders that are actually running their functions at the company should have my knowledge, as opposed to Brandon being the proxy.

So for our portfolio companies, that primary I interview a lot of like very late stage sales, marketing, customer success candidates.

And time and time again I am shocked that these people who are in VP level roles cannot clearly articulate to me.

Joining me and this is exactly what the air our journey look like or this is exactly what the margin journey looks like.

And so I think to your point, sometimes you're forced into it when you're in the executive leadership team because you're in the board meetings and you're in the air and you have no choice.

So if you are listening, you have to learn some of this by absorption.

But the next level down, I think, is.

Really acutely at risk sometimes and needs.

If they're going to think about C-suite readiness, they need to be able to go and do that.

And I tell people like probably of all of those interviews, I do, and I mean, it's dozens if not over a hundred a year.

90% of the candidates will not pass my interview.

And I'm not like a crazy interviewer.

I think these are reasonable questions and expectations, you know, for someone who's coming into the job.

And so I just think, you know, people that the opportunity is ripe for folks to focus on leveling up their.

I interviewed someone yesterday, a senior candidate who literally didn't mention one number in a 40 minute interview.

If our listeners can only remember one thing from our conversation today, what is that one thing?

The importance of alignment.

I think aligned teams are successful teams, and as I said earlier, I think the number one way to do it is to align compensation, but I think are in a way that is what separates good from great innovation teams.

This is where I think communication matters and why it's not part of top team, but its own skill is alignment is communication, because communication is talking and listening, like you said in the beginning, because you're a good sales leader.

Communication is the means to the end, right?

Exactly.

To your point, that's how do you drive alignment.

You need clarity and you need communication and you need to reinforce that clarity over and over and over again.

But I think also the listening cultivates the alignment because you need to listen to what people are actually saying to understand whether or not they're aligned completely agreed.

And I do think that's where practices like the quarterly business reviews are huge.

And in a prior organization I heard an executive complaining to the CEO that he had to sit in all of the different functional covers.

And going back to our point about what makes a great executive like that is the most naive comment I have ever heard.

Because for you to be a great executive, for you to know how this business operates, you need to know what's going on here to our earlier conversation.

You have to be willing to challenge, right?

If it doesn't make sense, ask the question.

Because when you don't challenge it, when you end up in the blame game 90 days later.

Right.

That no one ever question, how are we going to find our pipeline over 90 days, whatever it may be like?

Do you read the news?

Come on, man, let's go.

So on that note, thank you, Cassie, for joining us on the operations room.

If you like what you hear, please leave us a comment or subscribe and we will see you next week.