68. First Team Loyalty: The Key to Executive Success
In this episode we discuss: how to implement the first team concept. We are joined by Cassie Young, General Partner at Primary Venture Partners, and seasoned SaaS CRO/CCO.
Love The Operations Room? Please support us by rating and reviewing it here.
We chat about the following with Cassie Young:
- How can leaders ensure that their "first team" prioritises organisational success over individual functions?
- What steps can teams take to align incentives and build trust to resolve conflicts more effectively?
- How does empathy in communication and transparency enhance team dynamics, especially in structured yet flexible meeting cadences?
- Why is developing P&L fluency and understanding market dynamics essential for senior executives, and how can organisations address these gaps?
- How can leaders strategically network and cascade critical insights to maintain clarity and alignment within teams?
References
- https://www.linkedin.com/in/cassyoung/
- https://www.primary.vc/
Biography
Cassie Young is a General Partner at Primary Venture Partners, a $1B AUM early-stage venture capital firm in New York, backing companies like Chief, Alma, and K Health. She leads B2B software investments and oversees the firm's portfolio impact team, the largest of its kind among seed funds globally.
Previously, Cassie was Chief Customer and Commercial Officer at Marigold (formerly CM Group), where she led global operations and strategy across a portfolio of marketing tech brands, following Marigold’s acquisition of Sailthru in 2018. At Sailthru, she held multiple executive roles, ultimately serving as Chief Revenue Officer. Earlier, she led marketing and analytics teams at GLG, Savored (acquired by Groupon), and TheLadders, starting her career as an analyst at Citigroup.
A Duke graduate with an MBA from Tuck School of Business at Dartmouth, where she earned the Dero Saunders Award, Cassie is passionate about advancing women in leadership. In 2023, she launched On the Business, a program helping hundreds of senior women in software enhance their P&L fluency and boardroom skills.
To learn more about Beth and Brandon or to find out about sponsorship opportunities click here.
Summary
08:12 Introduction and Context Setting
19:17 Understanding the Concept of First Team
21:00 The Importance of Team Dynamics
21:35 Creating a First Team Mindset
23:00 Fostering Cross-Functional Collaboration
24:13 Aligning Incentives for Team Success
28:25 Overcoming Pushback on Team Engagement
31:12 Communicating with Empathy
34:04 Effective Meeting Cadences
41:03 Navigating Conflict and Accountability
42:23 Essential Skills for Executives
46:06 The Role of Founders and Leadership Styles
48:43 The Importance of Alignment and Communication
Transcript
Hello everyone, and welcome to
Speaker:another episode of The Operations
Speaker:Room, a podcast for CEOs.
Speaker:I am Brandon Mensing, a joined by
Speaker:my lovely coach, Bethany Ayres.
Speaker:How are things going, Bethany?
Speaker:You know how December is really
Speaker:hard and you have to do so much work
Speaker:and you have all of the parties, but
Speaker:everybody's like, but don't worry,
Speaker:it'll all be over.
Speaker:And then you can breathe out in
Speaker:January.
Speaker:And then if you run the fiscal year
Speaker:or even one month off, that's a lie
Speaker:because January is twice as hard as
Speaker:December.
Speaker:Is that true?
Speaker:I think it is.
Speaker:Or at least that's where I am.
Speaker:There's such incredibly intense
Speaker:months and then there's January.
Speaker:And also just
Speaker:the way that we're running it this
Speaker:year like so I'm just back from four
Speaker:days in Manchester.
Speaker:The Tuesday was
Speaker:our monthly
Speaker:go to market meeting and
Speaker:kind of quarterly planning session.
Speaker:I don't know if I've mentioned this,
Speaker:but so I'm also
Speaker:running the account management team
Speaker:as maternity cover for the next
Speaker:year.
Speaker:And I. You briefly mentioned this.
Speaker:Yes, right.
Speaker:All things to all people.
Speaker:That's Bethany.
Speaker:If that's me, that isn't that the
Speaker:CEO thing, like, you know, all the
Speaker:different roles that you can.
Speaker:Yeah. The Swiss Army knife of
Speaker:talent. That means that you can be
Speaker:slotted into anything on top of
Speaker:your other jobs.
Speaker:I guess what's exciting about that
Speaker:is that you're hitting all the
Speaker:levels of the business, right, is
Speaker:like functional, practical all the
Speaker:way through the strategic.
Speaker:Yeah. But then next week I'm
Speaker:luckily at home.
Speaker:The next week is planning for
Speaker:peak kickoff sales,
Speaker:kick off pro serve,
Speaker:kick off all the
Speaker:content production next week
Speaker:and then the following week back in
Speaker:Manchester for all of those kick
Speaker:offs. Tuesday, Wednesday, Thursday,
Speaker:get home Thursday night,
Speaker:fly to Jaipur,
Speaker:Friday morning, and
Speaker:then in Jaipur for a week doing
Speaker:kick off.
Speaker:So that includes like engineering
Speaker:and product kick off.
Speaker:So that is a tremendous amount of
Speaker:planning and kind of kicking
Speaker:things off for 2025.
Speaker:So and usually the CEO, you're so
Speaker:intimately involved in all these
Speaker:kick offs.
Speaker:I'm looking forward to February.
Speaker:February is when I can read that.
Speaker:But it was an interesting
Speaker:QPR and strategy
Speaker:session that I thought would be
Speaker:worth talking about.
Speaker:I was responsible
Speaker:for running the QB
Speaker:R and the Exac off site
Speaker:strategy session and I was
Speaker:really stressed going into it
Speaker:because I felt underprepared
Speaker:and I didn't know what kind of
Speaker:format was work and
Speaker:I didn't know how they were going to
Speaker:go. So the QPR, just for a bit of
Speaker:background, is a reboot
Speaker:with the wider teams we haven't had.
Speaker:We've been doing Kubernetes just as
Speaker:an executive and that's been working
Speaker:well and this is the first time
Speaker:we've added the next layer
Speaker:like their direct reports in.
Speaker:And then this is my
Speaker:first exec offsite
Speaker:two to run.
Speaker:And first of all, I realized
Speaker:that I'm I much prefer spontaneity
Speaker:than structure. Surprise, surprise.
Speaker:I don't know if this is the first
Speaker:time we've realized this about me.
Speaker:I think has been the consistent
Speaker:revelation over the course of the
Speaker:podcast.
Speaker:But I guess it's just like you think
Speaker:about a CEO, they're all about
Speaker:structure and process and blah,
Speaker:blah, blah. And I'm like the
Speaker:antithesis of that kind of code,
Speaker:despite being a Swiss Army knife, is
Speaker:able to do whatever role I need to
Speaker:do.
Speaker:So we had
Speaker:broad agenda items,
Speaker:but way more relaxed
Speaker:and had a huge amount of
Speaker:preparation.
Speaker:So like for the
Speaker:strategy day,
Speaker:we probably had 150,
Speaker:200 slides
Speaker:slash pages
Speaker:to read over a week,
Speaker:questions to think about
Speaker:context.
Speaker:But if you think about it, it's, you
Speaker:know, across all of the different
Speaker:departments, it's not actually that
Speaker:many slides per department, but
Speaker:everybody having the context
Speaker:of the goals, the
Speaker:challenges, the must dos,
Speaker:what's going well, what's not going
Speaker:well in each of the departments
Speaker:and the interconnects.
Speaker:We were able to go in
Speaker:and be very much less structured
Speaker:and we kind of started with problem
Speaker:number one and then let it just be
Speaker:an open conversation.
Speaker:And it was probably one of the most
Speaker:effective conversations we've ever
Speaker:had. Had some amazing insights
Speaker:come out of it.
Speaker:And it also naturally concluded
Speaker:at about an hour 45.
Speaker:I feel like this is resolved.
Speaker:We're done.
Speaker:Then we knew what our next topic
Speaker:was. Took quite a big
Speaker:break because we had to do some
Speaker:other stuff and I regrouped
Speaker:with everybody having
Speaker:that time to think.
Speaker:And then the next topic was covered
Speaker:in that same kind of time frame.
Speaker:Naturally concluded as we did our
Speaker:final one.
Speaker:And the final one was okay.
Speaker:So because it wasn't like such a
Speaker:totally exhausting day,
Speaker:we were able to have much better
Speaker:conversations around the Oscars and
Speaker:like properly, rather
Speaker:than it being the rush at the end.
Speaker:People's brains were still active.
Speaker:And so I was trying to reflect
Speaker:on what made it work well.
Speaker:And I think it was actually
Speaker:the fact that we're a highly
Speaker:functioning and performant team at
Speaker:the moment.
Speaker:That means that I don't
Speaker:think the structure matters.
Speaker:I think whatever structure it was
Speaker:would have worked.
Speaker:And also a lot of it
Speaker:was around how do we work better,
Speaker:how do we solve the problems
Speaker:together? How does everybody
Speaker:contribute to the overarching
Speaker:functioning of the company
Speaker:rather than siloed?
Speaker:And that was really
Speaker:it felt really good.
Speaker:I guess I found that the really
Speaker:highly structured ones don't work.
Speaker:So it was a bit of a gamble.
Speaker:So now of course, I'm like, How do I
Speaker:do it again?
Speaker:Well, we get to the.
Speaker:Quarterly versions of all of this.
Speaker:Why do you think the team was in a
Speaker:good place, do you think, to have
Speaker:high quality conversations?
Speaker:Because I'm an amazing leader.
Speaker:Part of it, I think, is because of
Speaker:this, the operating model or the
Speaker:cadence that I've spoken about,
Speaker:where we're seeing each other twice
Speaker:a week.
Speaker:We're able to bond
Speaker:and build trust through that regular
Speaker:contact surfacing
Speaker:issues.
Speaker:So not letting things
Speaker:slide.
Speaker:It's like I do a lot of face
Speaker:reading.
Speaker:And so when I see somebody whose
Speaker:face is like the micro
Speaker:second of a grimace
Speaker:or an eye roll, I don't let it
Speaker:pass. And I don't say you've just
Speaker:rolled her eyes because that's, you
Speaker:know. But I'll just say,
Speaker:it looks like you
Speaker:have an issue with that.
Speaker:What are you thinking?
Speaker:And then we let it come out
Speaker:until they're like no
Speaker:grimaces or eye rolls
Speaker:and things have surfaced.
Speaker:So that is working.
Speaker:Encouraging more
Speaker:communication between teams.
Speaker:Or like you two are clearly
Speaker:not speaking enough if
Speaker:these are surprises that are coming
Speaker:out in the meeting.
Speaker:Figure out how you're going to
Speaker:communicate together.
Speaker:So there's a lot more interconnect
Speaker:one on ones between team members
Speaker:when it comes becomes obvious that
Speaker:people are not talking the way they
Speaker:should. And then having a bit of a
Speaker:laugh like being okay with
Speaker:some joking, a little
Speaker:bit of that, the levity of it.
Speaker:And actually something I've done in
Speaker:the last two days and I don't know,
Speaker:I mean, I have to ask people if it's
Speaker:coming across genuine and genuine
Speaker:or not. Like for me, it is genuine.
Speaker:Is my finishing on a high but
Speaker:like reflecting on these
Speaker:been some conversations that are
Speaker:difficult?
Speaker:This person might be feeling like
Speaker:they're being quite beaten up, but
Speaker:the fact that they're being beaten
Speaker:up is because of how far we've
Speaker:progressed that we're even able to
Speaker:have that conversation versus
Speaker:where we were before.
Speaker:Let's take a moment to reflect on
Speaker:how much we've achieved
Speaker:and therefore what's going forward.
Speaker:And also like calling out
Speaker:good things that have happened and
Speaker:recognizing those good things in the
Speaker:meeting.
Speaker:So it's like reinforcing the good
Speaker:behaviors or the good ideas or the
Speaker:good connections between us.
Speaker:We have got a great topic for today,
Speaker:which is how do you implement the
Speaker:first team concept?
Speaker:We have an amazing guest for this,
Speaker:which is Cassie Young.
Speaker:She's the general partner at Primary
Speaker:Venture Partners and a seasoned
Speaker:S.R.O.
Speaker:slash chief customer officer.
Speaker:So maybe first off, your definition
Speaker:of first team.
Speaker:The most senior team
Speaker:that you are a part of is your first
Speaker:team.
Speaker:And so as an executive, it's the
Speaker:exact team that for your direct
Speaker:reports, it's that team
Speaker:you like that functional team.
Speaker:And what that means is that you
Speaker:put your first team
Speaker:ahead of your other teams.
Speaker:So it's if you're on the exac
Speaker:how do you solve the business's
Speaker:problems and
Speaker:have your team as your
Speaker:department or your function as
Speaker:resource to solve the company's
Speaker:problems rather than viewing
Speaker:it as you're going into
Speaker:exact team meetings to represent
Speaker:your team.
Speaker:So first team really is prioritizing
Speaker:your peer level team.
Speaker:And in this case, for us, that's the
Speaker:leadership or executive team.
Speaker:And the reason why, as opposed to
Speaker:your direct reports and the reason
Speaker:why that's useful is for
Speaker:my collective leadership team to
Speaker:come together to solve the company's
Speaker:problems, fundamentally working
Speaker:together to make that happen as
Speaker:opposed to representing your
Speaker:functional unit.
Speaker:So I guess some of the challenges in
Speaker:making this come alive for
Speaker:companies.
Speaker:The first one is conflicting
Speaker:loyalty, which is they're
Speaker:loyal to their direct reports,
Speaker:they're loyal to their function.
Speaker:That's how they've grown up in terms
Speaker:of their lineage within marketing or
Speaker:sales or whatever.
Speaker:And now they're being presented
Speaker:with this idea that they should be
Speaker:treating and prioritizing their peer
Speaker:level team, the leadership team,
Speaker:as their number one priority as
Speaker:opposed to their function now.
Speaker:And they have that kind of
Speaker:conflicting feeling of loyalty.
Speaker:So what do you do with that?
Speaker:I think it's around how you mature
Speaker:as a leader, and it's actually
Speaker:something that you need to learn to
Speaker:progress to the next level.
Speaker:So, you know, as an individual
Speaker:contributor, the first step
Speaker:is being directed by somebody else.
Speaker:The second step is directing
Speaker:yourself.
Speaker:Then you have the ability as
Speaker:a manager to direct a team
Speaker:and then as a senior manager or
Speaker:director, it's directing multiple
Speaker:teams.
Speaker:Then you get to the VP level.
Speaker:It's not just running a function,
Speaker:it's looking across
Speaker:the teams and so like
Speaker:representing your team,
Speaker:but in the context of the rest of
Speaker:the organization.
Speaker:So like not having a victim
Speaker:mentality, you know, rather than
Speaker:just saying, well, marketing gives
Speaker:us shit leads, you work
Speaker:with marketing to get the leads that
Speaker:you want.
Speaker:And that's a real mind shift
Speaker:change.
Speaker:But that's, I think, still
Speaker:representing your team
Speaker:but not being a victim and being
Speaker:proactive.
Speaker:And then when you move to the exac
Speaker:it's understanding that now
Speaker:that your team is the company,
Speaker:how does your team help the company
Speaker:rather than how does the company
Speaker:help your team?
Speaker:So the other one of interest here
Speaker:was resistance to vulnerability,
Speaker:because what you need in that
Speaker:leadership team is for people to
Speaker:trust each other, to be able
Speaker:to bring forward challenges and
Speaker:problems in a very honest, authentic
Speaker:way, to allow the group to help each
Speaker:other figure out what the best thing
Speaker:to do is. And the worst thing in the
Speaker:world is to have your marketing
Speaker:leader to come in and to obvious
Speaker:skate and to not share what is
Speaker:happening in terms of something that
Speaker:may not be good.
Speaker:And they feel somehow
Speaker:that they can't trust the others in
Speaker:the group to share it and to feel
Speaker:like they may be viewed in a certain
Speaker:way, I suppose.
Speaker:And I guess the question is, how do
Speaker:you create that trusting allow
Speaker:that vulnerability to occur where
Speaker:I'm sharing something within my
Speaker:function that is not good, but
Speaker:I need help and I'm happy
Speaker:to share that to the group and
Speaker:actually get the group to help me
Speaker:think it through.
Speaker:So in the past,
Speaker:I would have thought about it as
Speaker:vulnerability of like, that's a
Speaker:problem in my area I need help
Speaker:with and then have the confidence
Speaker:to feel like, okay, I'm not going to
Speaker:lose my job because of it.
Speaker:But often
Speaker:the things that are going to cause
Speaker:you to lose your job are your
Speaker:problems.
Speaker:You know, like you've hired the
Speaker:wrong VP of growth
Speaker:and you're not delivering well.
Speaker:And there are people issues and
Speaker:actually nobody else can solve that
Speaker:problem because it is something
Speaker:in your own area and
Speaker:in the first team
Speaker:it should be.
Speaker:How do you broach the topic of
Speaker:it's not that your VP of growth
Speaker:is failing.
Speaker:It's that the product
Speaker:has fallen behind the rest
Speaker:or the way the
Speaker:sales team is acting
Speaker:and selling is so against
Speaker:the brand.
Speaker:Your brand is now been rubbished in
Speaker:the market and it's not.
Speaker:How are you vulnerable around your
Speaker:area, but how do you raise
Speaker:topics that are impacting
Speaker:your team because
Speaker:of other areas and how do you
Speaker:have that rather than like pushing
Speaker:the product person under the bus?
Speaker:How do you frame it in a way that
Speaker:is a problem that everybody needs to
Speaker:solve?
Speaker:It kind of works both ways, isn't
Speaker:it, those your functional issues
Speaker:that are happening, but there's also
Speaker:things that you're saying within
Speaker:other functions. Say you're very
Speaker:concerned about.
Speaker:Yeah. And then it comes down to
Speaker:how do you approach it in a way
Speaker:that doesn't freak everybody out and
Speaker:get super defensive so that you can
Speaker:have a good conversation around
Speaker:it. Talk about resource allocation.
Speaker:Talk about plans, talk about like
Speaker:what the other departments can do to
Speaker:help the one
Speaker:who's struggling.
Speaker:And I think to be honest, Bethany, I
Speaker:feel like this topic is probably the
Speaker:single most difficult thing
Speaker:in any business is to have this
Speaker:happen. You know, I mean, I've seen
Speaker:this over and over again where I've
Speaker:tried all sorts of things over time
Speaker:to put the group in a position where
Speaker:we can have these conversations in a
Speaker:healthy, constructive way.
Speaker:But it is very difficult.
Speaker:People fundamentally are very
Speaker:loathed to point out other
Speaker:people's potential issues.
Speaker:Any things that you would think
Speaker:about as to how to facilitate this
Speaker:or to make this better over time.
Speaker:So I think part of it at least.
Speaker:For me is I'm
Speaker:often the one pointing it out
Speaker:in my current role because I can
Speaker:see and I'm looking holistically.
Speaker:One of the things that I'm using to
Speaker:do this is the
Speaker:SAS flywheel idea.
Speaker:Where have you seen this?
Speaker:Where?
Speaker:It's a line in a circle.
Speaker:I talked about it actually around
Speaker:metrics for on the business
Speaker:event, but I use it a lot for
Speaker:basically like that customer
Speaker:journey. So it's
Speaker:leads, opportunities, customers
Speaker:is the straight line and then the
Speaker:flywheel is where the customers you
Speaker:on board, the customers.
Speaker:They're so happy that they buy more,
Speaker:renew, renew,
Speaker:buy more. I'm never quite sure which
Speaker:order makes more sense.
Speaker:And then you on board them.
Speaker:They're happy and they keep
Speaker:spending. And that's the SAS
Speaker:flywheel where the land and expand
Speaker:happens or
Speaker:they don't expand, but they're big
Speaker:enough at a point that you retain
Speaker:them.
Speaker:And looking through
Speaker:that customer journey
Speaker:and seeing the pain points and
Speaker:like, you know, the pain point might
Speaker:be in support
Speaker:and the number of bugs that they're
Speaker:dealing with. But then you can
Speaker:follow that journey through and see
Speaker:what is causing the issue.
Speaker:So looking at it systemically
Speaker:and it's not rarely is it one
Speaker:person's mistake
Speaker:or issue.
Speaker:It tends to be death
Speaker:by a thousand cuts.
Speaker:And so you look at like, what are
Speaker:all the things that are contributing
Speaker:to that and therefore, what can we
Speaker:all do to make it better?
Speaker:Yeah, I like that.
Speaker:So it's more of a systemic view
Speaker:across the organization.
Speaker:And to your point, a lot of issues
Speaker:are cross functional nature in some
Speaker:form. It's not usually strictly a
Speaker:sales problem or marketing problem
Speaker:or a product problem.
Speaker:It's certainly, as you said, across
Speaker:a broader spectrum and kind of
Speaker:walking that logic through, I guess,
Speaker:and also perhaps the data nuggets
Speaker:behind that allows it to be less
Speaker:people function focus and more of a
Speaker:collective problem for the group, I
Speaker:suppose. And I guess the other part
Speaker:is the modeling, because if you're
Speaker:pointing it out, which as an
Speaker:example, you're modeling the ability
Speaker:for others to do the same in a
Speaker:constructive, useful fashion, which
Speaker:is we are having issues and
Speaker:if you're happy to point things out,
Speaker:then perhaps that's can have a knock
Speaker:on effect for the others in the
Speaker:group to feel comfortable to do the
Speaker:same thing.
Speaker:And I guess the other point is you
Speaker:being in a position where you're
Speaker:rewarding that behavior, either
Speaker:in the meeting or after the meeting
Speaker:in terms of making people feel
Speaker:like they've done the right thing by
Speaker:having that discussion, doing it in
Speaker:a very constructive way.
Speaker:And then equally, if
Speaker:people are not doing that, then
Speaker:making sure that you're having
Speaker:conversations around that to, I
Speaker:suspect 1 to 1 in that case to
Speaker:encourage that.
Speaker:And then also just wanted to point
Speaker:out one thing in what you were
Speaker:saying around, it's not around
Speaker:specific people.
Speaker:That's actually one of the lessons
Speaker:from the, you know, Wickman
Speaker:book Ethos Entrepreneurial Operating
Speaker:System. Like I think my biggest
Speaker:takeaway from that book is
Speaker:that all problems are people
Speaker:problems.
Speaker:You know, like genuinely, rather
Speaker:than trying to scaffold something
Speaker:around somebody who's incapable of
Speaker:doing their job.
Speaker:Being able to have that conversation.
Speaker:And so even if you're looking at the
Speaker:entire flywheel,
Speaker:you may notice
Speaker:that we have a skills gap, we
Speaker:have an experience gap.
Speaker:We have somebody who, you know,
Speaker:it might be that actually
Speaker:that VP of
Speaker:Growth who's not delivering leads.
Speaker:If marketing realized it, they would
Speaker:just change their VP of growth.
Speaker:But if somebody else is realizing
Speaker:and pointing it out, then you have a
Speaker:conversation around are we being
Speaker:unfair, blah blah.
Speaker:And the solution may be that you
Speaker:replace a VP of Growth,
Speaker:but that's a team conversation
Speaker:rather than like the marketing
Speaker:person having to be all by
Speaker:themselves realizing that somebody
Speaker:is underperforming, but they've just
Speaker:hired them and it took them eight
Speaker:months. They don't want to fire
Speaker:them. It's like, now you have to
Speaker:fire them.
Speaker:No, that's a great point actually,
Speaker:because like the skill gap or
Speaker:capability gap or something's
Speaker:happening and be in a position to
Speaker:include that as part of the
Speaker:conversation makes obvious sense
Speaker:as well. I guess the other one that
Speaker:I was thinking about that you
Speaker:pointed out some time back, and this
Speaker:is a slightly broader trust building
Speaker:kind of activity, I guess, which is
Speaker:something in the business that truly
Speaker:speaking, pulls a leadership team
Speaker:together to focus on something that
Speaker:really, really matters and to have
Speaker:that shared experience, a
Speaker:galvanizing experience where
Speaker:we're all in this together, we got
Speaker:to make this happen. It's a bit
Speaker:extraordinary, but let's do it and
Speaker:let's make it happen.
Speaker:And having that shared experience
Speaker:where you're working very closely,
Speaker:side by side with the leadership
Speaker:team can really make a difference.
Speaker:A breakthrough, a difference in
Speaker:terms of the trust that you've
Speaker:actually built within that
Speaker:leadership team.
Speaker:I think your example that you gave
Speaker:was fundraising, because
Speaker:fundraising is kind of a bit of
Speaker:a battle cry to the business and in
Speaker:particular the leadership team to
Speaker:pull themselves together to get
Speaker:the right metrics and getting on the
Speaker:road to talk to VCs
Speaker:around, you know, the business and
Speaker:why it's tremendously exciting and
Speaker:so on. What do you make of that?
Speaker:I do agree. Like so often people
Speaker:view fundraising
Speaker:as a burden and a distraction,
Speaker:but instead they should view it
Speaker:as an opportunity to both
Speaker:build together as a team and grow as
Speaker:a team, but also get all
Speaker:the strategy questions out of the
Speaker:way and. Like really properly
Speaker:think about your next 3 to 5 years
Speaker:when you're doing it.
Speaker:So love it. Let's park it here.
Speaker:And let's move on to our
Speaker:conversation with Ms..
Speaker:Cassie Young.
Speaker:So the concept of first team or team
Speaker:number one, as is sometimes called,
Speaker:was made famous by Patrick, like
Speaker:Yoni, who wrote books like Five
Speaker:Dysfunctions of a Team and the
Speaker:Advantage, which are some of my
Speaker:favorite business, reads.
Speaker:The central concept of it is that
Speaker:the more senior you become
Speaker:in an organization, the more
Speaker:important it is for you to embrace
Speaker:the reality that your first team
Speaker:is your team of peers.
Speaker:Right. So the most senior
Speaker:team that you sit on versus
Speaker:your functional swim lane or your
Speaker:direct reports.
Speaker:So if you are the chief marketing
Speaker:officer of a B2B software company,
Speaker:your first team is most likely that
Speaker:cross-functional leadership team
Speaker:that you sit on with, the CFO and
Speaker:the CTO, etc., not
Speaker:your head of demand gen
Speaker:or head of brand.
Speaker:And it sounds really obvious
Speaker:when people hear it just said that
Speaker:squarely out.
Speaker:But people don't think about that
Speaker:often in sort of the day to day
Speaker:rhythms of their work.
Speaker:And what happens when they don't
Speaker:embrace that is they fall victim
Speaker:to what I call the swim line trap.
Speaker:And we can talk more about that
Speaker:later.
Speaker:But the one thing I want to harp on
Speaker:with first team is it actually
Speaker:cascades the whole way down in the
Speaker:organization. So the example
Speaker:I give people is if you're the chief
Speaker:customer officer, you probably
Speaker:have this team of lieutenants that
Speaker:report to you like your head
Speaker:of technical support and you're head
Speaker:of the CSM team and you're head of
Speaker:professional services.
Speaker:They are your second team,
Speaker:right? For all the reasons we just
Speaker:talked about.
Speaker:But they are each other's first
Speaker:team because that's the most senior
Speaker:team that they sit on.
Speaker:And time and time again, I find this
Speaker:is a really powerful message
Speaker:for up and coming directors
Speaker:in an organization because it's like
Speaker:the blame game or one function to
Speaker:the other, and they have to embrace
Speaker:the concept of team number one and
Speaker:first team as well.
Speaker:My experience is
Speaker:I've looked at it in a slightly
Speaker:different way where maybe I
Speaker:haven't realized I was thinking
Speaker:about it in first team.
Speaker:For me, if you get first team right,
Speaker:then you just don't have the
Speaker:politics because where the politics
Speaker:come in is my team
Speaker:is my identity is being a CMO.
Speaker:And so what I care about more than
Speaker:anything is how do I promote
Speaker:my function?
Speaker:And if you have everybody doing
Speaker:that, you get loads of politics.
Speaker:Whereas if you view
Speaker:the success of the company
Speaker:as your job, you don't tend
Speaker:to backstab your colleagues.
Speaker:That's right. And I think like to
Speaker:bring that to life for a moment.
Speaker:I always share this example of a
Speaker:board slide I unfortunately
Speaker:had to witness right where and
Speaker:I'm going to pick on marketing, but
Speaker:we can pick on some other functions
Speaker:later.
Speaker:You know, the CMO had this slide
Speaker:in the board deck that was
Speaker:celebrating the fact that quarter
Speaker:over quarter they had double
Speaker:the number of closed one deals that
Speaker:were sourced by marketing, right?
Speaker:So they said we went from 45%
Speaker:of closed one deal stores by
Speaker:marketing to 90%.
Speaker:And this was this huge celebratory
Speaker:point.
Speaker:But what was lost on that particular
Speaker:slide is that this was presented in
Speaker:the context of a board
Speaker:meeting where we discussed how the
Speaker:overall business had shrunk.
Speaker:Okay. So the business is shrinking
Speaker:and the marketing leader is in there
Speaker:celebrating the fact.
Speaker:Right. That more of the closed one
Speaker:deals were sourced by marketing.
Speaker:The same thing happens though, like
Speaker:in product and engineering
Speaker:functions. Everyone comes in and
Speaker:celebrates roadmap velocity
Speaker:and all the feature shift.
Speaker:You know, we had an event in New
Speaker:York recently where the CTO
Speaker:speaker had this great line where
Speaker:she said, If it can't be sold,
Speaker:it doesn't matter.
Speaker:And so for product and engineering,
Speaker:I'm like, if you don't have the
Speaker:corresponding data and adoption and
Speaker:monetization, right, it's the same
Speaker:trap.
Speaker:But that's an A Your point on
Speaker:politics is also an interesting one
Speaker:because all of those books
Speaker:right by table group, they
Speaker:have a whole other definition of the
Speaker:world politics, right? Where they
Speaker:say politics in the organization
Speaker:is actually when you change your
Speaker:message based on the audience.
Speaker:Right. And I think that actually
Speaker:does apply here as well to where
Speaker:there may be one message that you
Speaker:have in your functional lane.
Speaker:Right. And one different set
Speaker:of things that you're talking about
Speaker:in the management suite.
Speaker:And so, one, it's I completely
Speaker:agree with you, it's putting the
Speaker:business above your
Speaker:functional result, but it's also
Speaker:that just consistency of messaging
Speaker:and how you're talking about things.
Speaker:And I incidentally listened to a
Speaker:podcast, but it was with
Speaker:Shane Battier, who's an NBA player
Speaker:here in the States. I'm a huge
Speaker:basketball fan. He's a Duke
Speaker:Ellington, so I always love to look
Speaker:at that in leadership advice.
Speaker:But they talked about this concept
Speaker:of playing for the front of the
Speaker:jersey, not the back,
Speaker:which I think was another really
Speaker:interesting way to think about the
Speaker:concept of first team, where you're
Speaker:not playing for your name, right?
Speaker:You're playing for the company.
Speaker:And I think that's just an easy way
Speaker:to explain the concept, particularly
Speaker:down the ranks as well.
Speaker:The question on the mind of the CEO
Speaker:always is how do you do this?
Speaker:How do you actually create a first
Speaker:team? So if you have individuals
Speaker:that are functionally coming from
Speaker:that mindset of I'm the functional
Speaker:owner, I'm responsible for
Speaker:marketing, I care about my metrics
Speaker:of my team, and they're the most
Speaker:important thing to me.
Speaker:And then you start trying to shift
Speaker:their mindset to a different space,
Speaker:i.e. the first team in this case can
Speaker:maybe just walk us through a bit of
Speaker:the practicality of like, how do you
Speaker:make that happen for sure?
Speaker:Well, the first thing I'll say to
Speaker:you is that I believe.
Speaker:Eve that teams will never be aligned
Speaker:if their compensation plans are not.
Speaker:And I think that's a very
Speaker:straightforward place to start.
Speaker:And I'll walk you through like a
Speaker:very tangible example of this.
Speaker:I was at a software company called
Speaker:Sales Group, and we went
Speaker:through this journey where the
Speaker:company grew faster
Speaker:than our technology would allow.
Speaker:We had scaling problems, right?
Speaker:Everything of that fold.
Speaker:We brought in an outside CEO
Speaker:and really had to execute something
Speaker:of a turnaround strategy around
Speaker:customer churn, customer trust,
Speaker:etc..
Speaker:What we said was, okay, there
Speaker:are functionally always
Speaker:going to be three things
Speaker:that matter most to us as a company,
Speaker:right? The first is to grow our
Speaker:business naturally, and the metric
Speaker:we're going to choose for how we
Speaker:grow our business is exit.
Speaker:RR Right, because that's the
Speaker:composite of new logos.
Speaker:It's the composite of what we don't
Speaker:churn, right? What we grow from
Speaker:expansion. So number one was grow
Speaker:the business with exit error.
Speaker:Number two was net
Speaker:promoter score, right?
Speaker:Because we said we want to.
Speaker:The second bucket of things is be
Speaker:a trusted partner.
Speaker:Now, you could argue the merits of
Speaker:NPS as a metric all day long.
Speaker:We had to focus on that because
Speaker:our NPS score was in the toilet.
Speaker:After these scaling challenges, it
Speaker:was -26 to give you
Speaker:a sense of it, right? So we needed
Speaker:its actual focus there.
Speaker:And then the third for us was
Speaker:operating predictably and
Speaker:responsibly, right?
Speaker:And for us that became a net burn
Speaker:target.
Speaker:And then over time it evolved into
Speaker:an EBITDA target, right?
Speaker:Once the business was cash flow
Speaker:positive.
Speaker:Now, we had in every
Speaker:monthly all hands for years
Speaker:the same first slide that had
Speaker:those three buckets and those
Speaker:metrics. So everyone was talking
Speaker:about that. The numbers change from
Speaker:year to year, but the central
Speaker:principles did not.
Speaker:Where this comes into first team and
Speaker:the management team was we change
Speaker:the executive bonus plans to say
Speaker:every executive has a 30%
Speaker:bonus that is driven by those
Speaker:three numbers.
Speaker:You would not believe the behavioral
Speaker:change you see in our product
Speaker:organization.
Speaker:That happens when suddenly
Speaker:the bonus is tied to Net Promoter
Speaker:score, right? It's tied to exit RR
Speaker:It just drives alignment.
Speaker:Now that is sort of the
Speaker:stick approach of how you
Speaker:go about it.
Speaker:I also think there's a lot of just
Speaker:kind of qualitative changes that you
Speaker:can encourage of the team as well.
Speaker:So for instance, I would say, you
Speaker:know, if you're an executive, you're
Speaker:probably doing one on ones with
Speaker:every single one of your functional
Speaker:direct reports every single week.
Speaker:What's your cadence with your peers
Speaker:on the first team?
Speaker:I don't think you need to be with
Speaker:them once a week, but at a minimum,
Speaker:I would expect you to meet with them
Speaker:once a month, right, that you're
Speaker:sitting down and getting aligned.
Speaker:So I do think it's on
Speaker:everybody to give
Speaker:that team the same priority
Speaker:and weight that they would.
Speaker:Right. The people who report to them
Speaker:that they're sort of growing and
Speaker:fostering. But I strongly
Speaker:believe that the fastest
Speaker:way to get there is to make sure
Speaker:that the incentives are extremely
Speaker:aligned.
Speaker:I agree to the extent that
Speaker:whenever I join a company
Speaker:and I am presented with my bonus,
Speaker:I just like, Is this how everybody
Speaker:else on the leadership team is paid?
Speaker:And if the answer is no, I
Speaker:said, Well, no, we're going to have
Speaker:to work on that. I'm not going to
Speaker:join where we're not paid in the
Speaker:same way because it doesn't work
Speaker:otherwise. And you're all pulling in
Speaker:different directions.
Speaker:The other way that I've helped
Speaker:foster this team is
Speaker:to talk about it as
Speaker:it's an element of development
Speaker:and it's like you're almost not
Speaker:ready for the next one if you can't
Speaker:sync across the company
Speaker:and you can only think in your swim
Speaker:lane and that will keep you
Speaker:from actually getting promoted or
Speaker:retaining that top table
Speaker:role.
Speaker:And that for me became very clear.
Speaker:When you hear people talk about
Speaker:it's X's fault, like, you know,
Speaker:marketing won't do what I need
Speaker:marketing to do,
Speaker:piece won't do what I need
Speaker:to do, What can I do?
Speaker:I am just here in sales
Speaker:and that is not
Speaker:a top team table mentality.
Speaker:Your job is how
Speaker:do I fix upstream?
Speaker:How do I fix downstream where
Speaker:a connected system, how
Speaker:do we fix this together?
Speaker:And that is
Speaker:how you get promoted and stay
Speaker:promoted.
Speaker:And I think one of the areas of
Speaker:pushback that I've had historically
Speaker:is that you all like a functional
Speaker:leader. And I'm suggesting
Speaker:to them around this, you know, first
Speaker:team mindset, this is the attitude
Speaker:that we should have. And their first
Speaker:reaction is, well, that's a
Speaker:whole bunch more activity in
Speaker:meetings that you're asking for
Speaker:that I don't have time for.
Speaker:So when you have that kind of reaction,
Speaker:you know what I suggested back to
Speaker:that person, this example, this was
Speaker:kind of what Bethany had said, which
Speaker:is, you know, when you think about
Speaker:your career development, you think
Speaker:about the next step for yourself.
Speaker:The next step literally, is you
Speaker:having to work on the business, not
Speaker:in the business.
Speaker:And on the business means A, B and
Speaker:C, And if you have no experience
Speaker:doing that, it's going to make it
Speaker:that much more difficult for you to
Speaker:make that jump and to be successful
Speaker:when you make that jump.
Speaker:So we have this back and forth and
Speaker:eventually we came to the right
Speaker:place. But this question of pushback
Speaker:around a whole bigger swath
Speaker:of meetings, what do you do with
Speaker:that?
Speaker:So maybe a two part answer.
Speaker:I agree with everything YouTube said
Speaker:right around like fundamentally, the
Speaker:job changes when you're an
Speaker:executive. And someone said to me
Speaker:many years ago that the more
Speaker:senior you become in an
Speaker:organization, the more all roles
Speaker:converge and your job is just
Speaker:people. Management are running the
Speaker:business right, and you might do it
Speaker:over product that ends.
Speaker:You might do it over sales and see
Speaker:what the jobs are all the same.
Speaker:And that really resonated with
Speaker:me. And one message I'll often say
Speaker:to up and comers is like, you have
Speaker:to choose if that's the path for
Speaker:you. Right?
Speaker:I think a lot of times people, they
Speaker:falsely conflate
Speaker:people management with leadership,
Speaker:right? Like the only way I can be a
Speaker:leader in this organization is if I
Speaker:have a bigger team and I run the
Speaker:function. That's actually not the
Speaker:job for everybody, right?
Speaker:There are many other ways to be
Speaker:standout leaders at an organization
Speaker:and to contribute, and I think
Speaker:naming that for people is super
Speaker:important to being very real about
Speaker:what the job it's as you climb
Speaker:through the ranks, right?
Speaker:Like everything is a people problem.
Speaker:When you're running a large
Speaker:organization, Like that's your job,
Speaker:that's what you're doing all day
Speaker:long. That said, Brendan, you know,
Speaker:to your point, I do think you have
Speaker:to be very disciplined in terms of
Speaker:meeting hygiene, right?
Speaker:Challenging norms.
Speaker:I feel like as I've been part of
Speaker:growing companies in the past, we've
Speaker:just had to commit ourselves
Speaker:to iterating and challenging the
Speaker:status quo, right.
Speaker:Every couple of months on what we
Speaker:were doing. So to give you an
Speaker:example, for the past life, we
Speaker:had a very tight quarterly business
Speaker:review process by every function.
Speaker:And it just became like the
Speaker:preparation for the quarterly
Speaker:business reviews just became totally
Speaker:daunting and probably not the best
Speaker:use of time. But we said, why don't
Speaker:we switch into more of kind of an
Speaker:Amazonian memo
Speaker:format, right?
Speaker:To put that together, give a free
Speaker:read. So I think there are ways that
Speaker:you can kind of shortcut or short
Speaker:circuit some of the meeting fatigue
Speaker:and prep, etc., that every
Speaker:organization just has to be very
Speaker:disciplined about saying like,
Speaker:is this an energy drain?
Speaker:And if so, what small adjustments
Speaker:could we make to make that, you
Speaker:know, more accommodating or
Speaker:appealing to the participants?
Speaker:So this is a challenge that I've
Speaker:recognized recently.
Speaker:I'm trying to get people to
Speaker:communicate with more
Speaker:empathy to
Speaker:their listeners. And what I don't
Speaker:mean is being kind or how are people
Speaker:going to feel, but
Speaker:what do people need to know
Speaker:to do their jobs better
Speaker:rather than sharing with people
Speaker:what I've been doing to justify
Speaker:why I have a job?
Speaker:I think it's very well said.
Speaker:It's really hard to make
Speaker:that transition and it's something
Speaker:like every meeting I'm just like,
Speaker:how do we get people to think about
Speaker:the information? And it's amazing
Speaker:because we share so much information
Speaker:that nobody consumes it.
Speaker:And then I go to a meeting and say
Speaker:something and half the room have no
Speaker:idea of like the one most important
Speaker:thing because it's hidden in all
Speaker:of the justification
Speaker:of jobs.
Speaker:Have you figure out ways to make
Speaker:this happen?
Speaker:I think it's really hard
Speaker:to your point, but one framing
Speaker:that I frequently think about many
Speaker:years ago, someone use this
Speaker:acronym and I was like, What's this
Speaker:acronym? An acronym was Weafer or
Speaker:the what's in it for me?
Speaker:I share that acronym now because I
Speaker:do think as you're working with
Speaker:different audiences, you have to
Speaker:approach it from the frame of what's
Speaker:in it for them, right?
Speaker:Like they are thinking about it that
Speaker:way. So to your point,
Speaker:it's not that you're coming
Speaker:to say, Hey, I need you
Speaker:to go do a ton of customer case
Speaker:studies, right?
Speaker:Because we don't have a it's hey,
Speaker:your goal is the marketing team,
Speaker:right? Is aligned.
Speaker:Do you know ultimately the number
Speaker:of influence closed one deals more
Speaker:of these case studies are going to
Speaker:help us get it done time and time
Speaker:again. We get that aspect, but it's
Speaker:really making it real for them
Speaker:based on their success metrics,
Speaker:which is why I think it becomes
Speaker:easier if everyone has the same
Speaker:success metrics, right?
Speaker:So that you don't have to politic
Speaker:that message in different places,
Speaker:but you have to preempt
Speaker:the question and sort of see the
Speaker:so what for people when you're
Speaker:talking with them or making that ask
Speaker:of them. I also just think there's a
Speaker:huge win to be had with
Speaker:just reinforce positive
Speaker:reinforcement when things work,
Speaker:right? So I think it's like very
Speaker:frequent. You know, you talk about
Speaker:customer feedback or problems or
Speaker:requests, but you know, oftentimes
Speaker:like customer wins are just thrown
Speaker:into a Slack channel and never
Speaker:really talked about like bringing
Speaker:a customer into regular
Speaker:all hands meetings, right?
Speaker:Giving the engineering team one
Speaker:approach that worked really well for
Speaker:me in the past was to bring in the
Speaker:technical stakeholder from different
Speaker:customers and have them sit down
Speaker:with the spread teams who built the
Speaker:product that they implemented.
Speaker:Because the engineers, like I
Speaker:was telling the CMO, is they didn't
Speaker:like necessarily really want to
Speaker:listen to what the CMO economic
Speaker:buyer had to say, but they loved
Speaker:getting the technical feedback
Speaker:right. I like the API flexibility,
Speaker:so I think it's meeting
Speaker:kind of your internal stakeholders
Speaker:where they are right with positive
Speaker:reinforcement aligned to the goals
Speaker:can be a strong path as well.
Speaker:When it comes to kind
Speaker:of cadences and the number of hours
Speaker:that you spend with your first team.
Speaker:Can you give us a bit of a and
Speaker:around that in terms of on a weekly
Speaker:basis, monthly basis, quarterly
Speaker:basis? Like what is a.
Speaker:A good mixture of things, do you
Speaker:think?
Speaker:Yeah. So and I'm not going to
Speaker:claim to take credit for this.
Speaker:I actually think a lot of my own
Speaker:learning on this came
Speaker:directly out of frameworks like
Speaker:those that are presented in the
Speaker:advantage and elsewhere.
Speaker:Right. But the general approach
Speaker:that I've seen worked really well.
Speaker:As you know, you have your weekly
Speaker:leadership team meeting, right,
Speaker:which is usually probably minimum an
Speaker:hour and a half, right.
Speaker:Kind of growing and scaling
Speaker:companies.
Speaker:I really like this idea of
Speaker:once a quarter for a day.
Speaker:You're taking that first team off
Speaker:site somewhere, right?
Speaker:To wrestle some larger
Speaker:business plan discussion.
Speaker:Right. Or talk about what the
Speaker:operating plan for the back half of
Speaker:the year is going to look like,
Speaker:etc..
Speaker:But I also like this idea of
Speaker:holding time once a month
Speaker:for ad hoc strategic topics
Speaker:that come up that can't wait until
Speaker:the next quarterly offsite.
Speaker:The trick with that, going back to
Speaker:your previous question, Brandon,
Speaker:about needing fatigue is like, if
Speaker:you don't need the meeting, just
Speaker:cancel it.
Speaker:Right. Which I think people are
Speaker:often afraid to do.
Speaker:But you hold the space, so it isn't
Speaker:like this crazy fire drill
Speaker:at the last minute to find 90
Speaker:minutes. And everyone's annoyed
Speaker:because you're disrupting their
Speaker:weekly workflow. So I like
Speaker:the dedicated weekly
Speaker:meeting and I want to come back to
Speaker:that because I think the format and
Speaker:what's done there is really, really
Speaker:important.
Speaker:This holding space once a month for
Speaker:an hour, hour and a half for a
Speaker:deeper dive topic, and then the
Speaker:quarterly data gather offsite and
Speaker:maybe once a year that's even longer
Speaker:right than the one that you're doing
Speaker:that for a longer period of time.
Speaker:Now that's the full team together.
Speaker:As I said earlier, there's also
Speaker:these monthly cadences around
Speaker:the table, right?
Speaker:So if I'm the zero, I'm probably
Speaker:going to have another five or
Speaker:so meetings, right, with the other
Speaker:kind of key CEOs around the table
Speaker:just to make sure we're sort of
Speaker:building that report, etc..
Speaker:And that monthly
Speaker:meeting is a good stopgap.
Speaker:But I also think it's like great
Speaker:executives go way above and beyond
Speaker:that. The quick comment I'll make
Speaker:just on the weekly cadence is I
Speaker:think a lot of times those meetings
Speaker:can just be highly dysfunctional,
Speaker:right. Where it's sort of a free for
Speaker:all what the agenda is.
Speaker:I do think there are some best
Speaker:practices that companies can follow
Speaker:around. Okay.
Speaker:We always start with the numbers,
Speaker:right? Number one, because we're
Speaker:working on the business right at the
Speaker:end of the day. It's amazing to me
Speaker:that I sometimes shadow
Speaker:leadership team meetings and I'm
Speaker:like, Where are the numbers again,
Speaker:this meeting, right?
Speaker:We're not just here to talk about
Speaker:how we're feeling or what the
Speaker:weather is looking like.
Speaker:So that's number one.
Speaker:Number two is the CEO
Speaker:is the boss.
Speaker:Right. So how do you let
Speaker:the CEO set the agenda for any
Speaker:given week? So in the past, I've
Speaker:like these approaches where, you
Speaker:know, the senior executives can
Speaker:propose topics, but ultimately
Speaker:the CEO curates
Speaker:the agenda from week to week around
Speaker:the places where they do or don't
Speaker:want to dig in.
Speaker:I love that talk about the
Speaker:CEO being the boss and the agenda,
Speaker:because then also
Speaker:you're the boss of your functional
Speaker:lead and you're doing the same.
Speaker:And that was one of the things that
Speaker:happened when I first became
Speaker:CEO and had basically
Speaker:all of the customer functions.
Speaker:So so is marketing, sales,
Speaker:data science, customer success.
Speaker:So we have like quite a few.
Speaker:And then like my
Speaker:job became basically
Speaker:an events organizer.
Speaker:I felt like I'm getting paid really
Speaker:a lot of money to organize
Speaker:meetings, but that is
Speaker:actually a large part of your job
Speaker:is to think about how to have
Speaker:good meetings and how to have
Speaker:meetings where people can talk
Speaker:and how you can get to the issues.
Speaker:And it was just such a weird moment
Speaker:for me.
Speaker:I also think it's like it's that and
Speaker:it's what's happening
Speaker:in those meetings is how you
Speaker:communicate, right?
Speaker:And how you drive clarity for
Speaker:people.
Speaker:Yeah, because when you think about
Speaker:it, you've got the 6 or 7 most
Speaker:expensive people in the company
Speaker:meeting on a weekly basis.
Speaker:And if that meeting is a shit show,
Speaker:you're kind of like wasting that
Speaker:money, number one. And the number
Speaker:two, the amplification.
Speaker:What comes out of that meeting, if
Speaker:it's been a terrible meeting and
Speaker:it's divisive or whatever,
Speaker:the impact on the rest of the
Speaker:company is, ripple effect is also
Speaker:potentially quite negative as well.
Speaker:I completely agree.
Speaker:And I think to that point, Brendan,
Speaker:like it is worthwhile at the end
Speaker:of executive meetings, particularly
Speaker:like the meatier monthly meetings or
Speaker:the quarterlies, but you can
Speaker:certainly do it with the week is
Speaker:aligning on what you are or are
Speaker:not going to cascade like
Speaker:what is off limits?
Speaker:And if it's not off limits, then
Speaker:you should feel empowered to go into
Speaker:your functional lane and cascade
Speaker:those mitigations. I think it's
Speaker:ridiculously important when you're
Speaker:going offsite because invariably
Speaker:when you take seven really expensive
Speaker:senior leaders of the company
Speaker:offsite, you know what's happening
Speaker:on the ground, right? Everyone's
Speaker:like, what's going on? What are they
Speaker:talking about is going to be layoffs
Speaker:are going to be this. So I do think
Speaker:being as open as possible with that
Speaker:is great. And you can really
Speaker:prioritize doing that week to week.
Speaker:We do that because I've noticed
Speaker:that there's an inconsistency
Speaker:of ability to communicate
Speaker:or an inconsistency of what is
Speaker:communicated. And so I introduced
Speaker:that, but I'm not sure
Speaker:we still always take the time.
Speaker:Like sometimes you have meetings.
Speaker:Because we meet twice a week.
Speaker:It's set for an hour. Sometimes it's
Speaker:a full hour. But like, as you said,
Speaker:sometimes it's 15 minutes because
Speaker:all we have is 15 minutes worth of
Speaker:stuff. But we have the two.
Speaker:And sometimes it's really clear that
Speaker:we need to talk about what we
Speaker:cascade. And other times it's like
Speaker:we just talked about random
Speaker:shit. Like, do we need to cascade
Speaker:this or not?
Speaker:And at first I was like, no, there's
Speaker:nothing to cascade. And it's like,
Speaker:No, that's not the point.
Speaker:It's not what should we it's
Speaker:what shouldn't we?
Speaker:And so it's like we just talked
Speaker:about random things.
Speaker:All of that is fine to share.
Speaker:If you think it's relevant for your
Speaker:team, it's much more important to
Speaker:identify the things that you
Speaker:actively shouldn't share.
Speaker:And then that frees up people
Speaker:to share more,
Speaker:because I think the default is with
Speaker:fear, they share less.
Speaker:I think related to that and your
Speaker:point about there's just such
Speaker:varying degrees of comfort with
Speaker:how people communicate, I
Speaker:think leaders almost have to force
Speaker:themselves into accountability.
Speaker:So I mentioned earlier when I was on
Speaker:the operating side, I sent this note
Speaker:every Monday night for years
Speaker:and years and years.
Speaker:And like I couldn't.
Speaker:Not do that note.
Speaker:So it just held me accountable.
Speaker:And I wrote the note over the course
Speaker:of the week.
Speaker:Okay, what do I want to include?
Speaker:I came out of the leadership meeting
Speaker:today. What am I going to put it
Speaker:from that in terms of takeaways in
Speaker:this note versus what am I not?
Speaker:My functional leaders knew they
Speaker:could send me stuff that they wanted
Speaker:in there, but it was just this
Speaker:forcing function for making sure
Speaker:I was communicating so
Speaker:it doesn't have to be once a week.
Speaker:It could be, Hey, look, I'm going to
Speaker:have a monthly engineering all hands
Speaker:and these are the things I'm always
Speaker:going to commit to talking about in
Speaker:that all hands. Meeting, right, is
Speaker:find what works for you.
Speaker:But I think you have
Speaker:to have some degree of
Speaker:accountability in like what the
Speaker:mechanism is for how and when you
Speaker:share.
Speaker:What do you do? In the case of the
Speaker:functional leader, that is obvious
Speaker:skating.
Speaker:Yeah. I mean, I think that really
Speaker:healthy teams have healthy conflict
Speaker:and it starts with the CEO.
Speaker:Do I mean in terms of making people
Speaker:comfortable, challenging each other
Speaker:very directly.
Speaker:And so I think what becomes hard is
Speaker:if you're in one of those meetings
Speaker:where silently everybody knows
Speaker:you're sort of an elephant in the
Speaker:room of what's going on and the CEO
Speaker:isn't willing to directly challenge.
Speaker:No one around the table is going to
Speaker:do it right. It starts it's all like
Speaker:the classic norming of the team.
Speaker:And this is why my earlier
Speaker:point about building trust, right,
Speaker:and kind of going out of your way to
Speaker:do that conflict is so much easier,
Speaker:right, when you have that trust in
Speaker:the first place because you can
Speaker:assume positive intent versus
Speaker:if you don't have that right,
Speaker:everything kind of goes haywire.
Speaker:And so I do think it's how do you
Speaker:get into the company rhythms of
Speaker:just naming it in the
Speaker:meeting? Going back to that earlier
Speaker:definition that I shared around
Speaker:politics, right, of saying different
Speaker:things to different audiences, this
Speaker:is where that shows up.
Speaker:It's like we can't talk about it in
Speaker:a group format.
Speaker:But then I'm going to go back and
Speaker:have a sidebar conversation with my
Speaker:CTO about the CMO.
Speaker:my gosh, what the hell are they
Speaker:doing all day long?
Speaker:And there's a polite and
Speaker:constructive way to do it and frame
Speaker:it right in the meeting.
Speaker:But I do think
Speaker:really strong companies
Speaker:kind of have that public
Speaker:display of challenge
Speaker:questioning, etc., But it's in
Speaker:the name of doing what's best for
Speaker:the business.
Speaker:I just thought it'd be interesting
Speaker:to take the change topic a little
Speaker:bit back to the first
Speaker:team. And
Speaker:are there universal
Speaker:skills that make
Speaker:for a great executive that
Speaker:we could almost just then lift as a
Speaker:leadership framework that we use
Speaker:when evaluating ourselves and our
Speaker:other leaders?
Speaker:Absolutely. So one is like,
Speaker:as we've just talked about analogy,
Speaker:I'm like embracing this leadership
Speaker:mentality, right?
Speaker:Where you do put your team
Speaker:number one first, but the second
Speaker:is just strong pencil
Speaker:command and fluency.
Speaker:And I think this is unfortunately
Speaker:very often lacking in senior
Speaker:executives. And so what do I mean
Speaker:by that?
Speaker:If you're a chief customer officer,
Speaker:you need to be well-versed
Speaker:in like the margin drivers of
Speaker:the business. Right?
Speaker:Because so much of what you're doing
Speaker:is is servicing
Speaker:the customers. Right?
Speaker:And you really have to understand
Speaker:what follows above the line, below
Speaker:the line and how you help advance
Speaker:the ball on that.
Speaker:And I think a lot of leaders
Speaker:have a hard time connecting
Speaker:their day to day work to the top and
Speaker:bottom lines of the company.
Speaker:So I think that's a good place to
Speaker:start. And, you know, people
Speaker:frequently say to me, well, you
Speaker:know, how do I go about doing that?
Speaker:I didn't go to business school.
Speaker:I didn't do X, Y or Z.
Speaker:My number one suggestion
Speaker:to them is take your CFO
Speaker:to lunch. This is like a branded
Speaker:campaign. I think I want to launch
Speaker:for 2025 or when I say CFO,
Speaker:it could be the VP
Speaker:of FCPA takes someone in the finance
Speaker:function at lunch because let's be
Speaker:honest, no one's inviting our
Speaker:finance colleagues to lunch right
Speaker:there in the bottom of the invite
Speaker:list, sitting down and saying,
Speaker:Hey, could you walk me top to bottom
Speaker:through our companies now?
Speaker:And the things that you're thinking
Speaker:about in advance of the next minute.
Speaker:The finance leaders love it when
Speaker:functional people come and ask them
Speaker:that question. So I think that's a
Speaker:really easy so I think first
Speaker:team piano fluency,
Speaker:I think the two other things that
Speaker:I'll highlight, one is just a
Speaker:command for what's going on in the
Speaker:market.
Speaker:So this is going to sound crazy, but
Speaker:I frequently say to people like, do
Speaker:you read the news?
Speaker:Right. Do you have a point of view
Speaker:on what's going on?
Speaker:Right. Particularly in this era of
Speaker:AI. Right.
Speaker:It's you have to have
Speaker:a perspective and you don't need to
Speaker:read that much news.
Speaker:But, you know, I always say, look,
Speaker:right now I invest in software
Speaker:companies. Many of them are A.I.
Speaker:native companies at this point.
Speaker:There is a lot of industry chatter
Speaker:around is everybody just
Speaker:experimenting with A.I.
Speaker:software are going to churn off of
Speaker:it. So if I'm talking to a C.
Speaker:S leader, I want them to come in
Speaker:with the point of view on what's
Speaker:going on in the market, right.
Speaker:And how they're thinking about that.
Speaker:And the final thing I'll mention and
Speaker:this this basically going back to
Speaker:that word you and I, that I do think
Speaker:is is more acute with women than men
Speaker:is just having a strategic network
Speaker:and making the space for that
Speaker:outside of your company.
Speaker:You may not want to copy
Speaker:verbatim what another business is
Speaker:doing, but every time I talk to
Speaker:leaders of other companies, they say
Speaker:something that just get my gears
Speaker:turning a little bit differently.
Speaker:Right. And I think this is
Speaker:particularly important in the era of
Speaker:remote work.
Speaker:I understand remote work can work
Speaker:really well for various companies,
Speaker:but if you're not going to be in an
Speaker:office every day, you have to work
Speaker:that much harder, right at
Speaker:how am I going to cultivate the
Speaker:strategic network if I'm not hosting
Speaker:people at the office, if I'm not
Speaker:meeting with clients in person
Speaker:regularly? So I just think people
Speaker:have to be deliberate about it, but
Speaker:that's probably at risk of gross
Speaker:oversimplification.
Speaker:But I think if you do those four
Speaker:things really, really well,
Speaker:right, In addition to the brass
Speaker:tacks stuff we talked about, about
Speaker:like communicating, etc.,
Speaker:which I think comes back, I think
Speaker:that's a recipe for success.
Speaker:But I would put that communication
Speaker:stuff in that first team
Speaker:bucket is kind of, you know, just
Speaker:being part and parcel with it.
Speaker:So speaking of seeing
Speaker:things in the news, did you see
Speaker:the video from the Nvidia
Speaker:CEO how he
Speaker:has 60 direct reports,
Speaker:No one to ones.
Speaker:I would just love to hear your
Speaker:thoughts on that.
Speaker:That was a talk of our office right
Speaker:when we saw that. And you probably
Speaker:also saw that was right around
Speaker:the time of the whole founder mode
Speaker:article that came out.
Speaker:And I thought the founder a piece.
Speaker:The interesting challenge that was
Speaker:put out there is our founders is
Speaker:going to use this as a convenient
Speaker:excuse to do whatever they want.
Speaker:And I think my take is
Speaker:100%.
Speaker:We had a line when I was at the
Speaker:operating site where we sometimes
Speaker:call things founder itis, right
Speaker:where they were just kind of happening
Speaker:in the business. But don't miss
Speaker:here. I think founders are
Speaker:incredible. Right? And this really
Speaker:breakout category, defining
Speaker:companies are who they are because
Speaker:of that founder DNA right off
Speaker:of what those founders do.
Speaker:I think that is probably
Speaker:not aligned with my personal
Speaker:approach about how it goes about
Speaker:clearly they're doing something
Speaker:right and it's working well for
Speaker:them. I just read a statistic on the
Speaker:number of video employees who are
Speaker:billionaires at this point, and it's
Speaker:absolutely insane in terms of
Speaker:the enterprise value that they've
Speaker:built. But I do think
Speaker:that is probably like an outlier
Speaker:exception case and
Speaker:it gets dangerous, right when we're
Speaker:out in the news talking about these
Speaker:amazingly highly performant
Speaker:companies and how they do work
Speaker:because the vast majority of
Speaker:companies can't operate
Speaker:that way.
Speaker:Right. So I think it's you have to
Speaker:have the creative license as a
Speaker:founder and CEO of what
Speaker:is going to work best for your
Speaker:company.
Speaker:But as you are getting started on
Speaker:that journey, I don't think you need
Speaker:to recreate the wheel.
Speaker:I think there are some tried and
Speaker:true best practices that you can
Speaker:throw up in flames, right, if
Speaker:they're not working for you.
Speaker:But I think orienting
Speaker:my fear is people see these crazy
Speaker:one off outliers.
Speaker:They're like, well, I'm going to go
Speaker:do it that way. But fundamentally,
Speaker:that's like a 1 in 1,000,000
Speaker:company, right?
Speaker:So getting back to your original
Speaker:fluency comment, you know, it's
Speaker:interesting. I just think about this
Speaker:in my head as you were speaking
Speaker:about when I joined companies as
Speaker:the CEO, I have like a real
Speaker:interest in piano fluency and being
Speaker:able to partner with the finance
Speaker:leader to ensure that we have
Speaker:forecast models that make sense and
Speaker:so on. And I end up spending a
Speaker:disproportionate amount of my time
Speaker:with that finance leader to really
Speaker:understand the models at a certain
Speaker:level of detail and to be able to
Speaker:communicate that effectively to
Speaker:investors or for fundraising or for
Speaker:the company or for the other leaders
Speaker:or whatever.
Speaker:So I end up playing this weird proxy
Speaker:role, like filling that gap or
Speaker:showing that hole in a way where the
Speaker:finance leader can't quite
Speaker:do it. So I step in as the
Speaker:communicator, but I have more of the
Speaker:understanding of the business in
Speaker:totality as opposed to the finance
Speaker:leader. So I end up being that
Speaker:person to represent, I guess in some
Speaker:sense. But I also feel like I maybe
Speaker:it's a bit of like what you said,
Speaker:Bethany, which is I'm filling a
Speaker:hole and legitimately the other
Speaker:functional leaders that are actually
Speaker:running their functions at the
Speaker:company should have my knowledge,
Speaker:as opposed to Brandon being the
Speaker:proxy.
Speaker:So for our portfolio companies, that
Speaker:primary I interview a lot
Speaker:of like very late stage
Speaker:sales, marketing, customer success
Speaker:candidates. And time and time again
Speaker:I am shocked that these people who
Speaker:are in VP level roles
Speaker:cannot clearly articulate to
Speaker:me. Joining me and this is exactly
Speaker:what the air our journey look like
Speaker:or this is exactly what the margin
Speaker:journey looks like.
Speaker:And so I think to your point,
Speaker:sometimes you're forced into it when
Speaker:you're in the executive leadership
Speaker:team because you're in the board
Speaker:meetings and you're in the air and
Speaker:you have no choice. So if you are
Speaker:listening, you have to learn some of
Speaker:this by absorption.
Speaker:But the next level down, I think,
Speaker:is. Really acutely at risk sometimes
Speaker:and needs. If they're going to think
Speaker:about C-suite readiness, they need
Speaker:to be able to go and do that.
Speaker:And I tell people like probably
Speaker:of all of those interviews, I do,
Speaker:and I mean, it's dozens if not over
Speaker:a hundred a year.
Speaker:90% of the candidates will not pass
Speaker:my interview. And I'm not like a
Speaker:crazy interviewer.
Speaker:I think these are reasonable
Speaker:questions and expectations, you
Speaker:know, for someone who's coming into
Speaker:the job. And so I just think,
Speaker:you know, people that the
Speaker:opportunity is ripe for folks to
Speaker:focus on leveling up their.
Speaker:I interviewed someone yesterday, a
Speaker:senior candidate who literally
Speaker:didn't mention one number in a 40
Speaker:minute interview.
Speaker:If our listeners
Speaker:can only remember one thing from our
Speaker:conversation today, what is that one
Speaker:thing?
Speaker:The importance of alignment.
Speaker:I think aligned teams are successful
Speaker:teams, and as I said earlier, I
Speaker:think the number one way to do it is
Speaker:to align compensation, but I think
Speaker:are in a way that is what separates
Speaker:good from great innovation teams.
Speaker:This is where I think
Speaker:communication matters and why it's
Speaker:not part of top team, but its own
Speaker:skill is
Speaker:alignment is communication, because
Speaker:communication is talking
Speaker:and listening, like you said in the
Speaker:beginning, because you're a good
Speaker:sales leader.
Speaker:Communication is the means to the
Speaker:end, right?
Speaker:Exactly. To your point, that's how
Speaker:do you drive alignment.
Speaker:You need clarity and you need
Speaker:communication and you need to
Speaker:reinforce that clarity over and
Speaker:over and over again.
Speaker:But I think also the listening
Speaker:cultivates the alignment because you
Speaker:need to listen to what people are
Speaker:actually saying to understand
Speaker:whether or not they're aligned
Speaker:completely agreed.
Speaker:And I do think that's where
Speaker:practices like the quarterly
Speaker:business reviews are huge.
Speaker:And in a prior organization
Speaker:I heard an executive complaining to
Speaker:the CEO that he had to sit in
Speaker:all of the different functional
Speaker:covers.
Speaker:And going back to our point about
Speaker:what makes a great executive like
Speaker:that is the most naive
Speaker:comment I have ever heard.
Speaker:Because for you to be a great
Speaker:executive, for you to know how this
Speaker:business operates, you need to know
Speaker:what's going on here to our earlier
Speaker:conversation.
Speaker:You have to be willing to challenge,
Speaker:right? If it doesn't make sense, ask
Speaker:the question.
Speaker:Because when you don't challenge it,
Speaker:when you end up in the blame game 90
Speaker:days later. Right.
Speaker:That no one ever question, how
Speaker:are we going to find our pipeline
Speaker:over 90 days, whatever it may be
Speaker:like?
Speaker:Do you read the news?
Speaker:Come on, man, let's go.
Speaker:So on that note, thank you, Cassie,
Speaker:for joining us on the operations
Speaker:room. If you like what you hear,
Speaker:please leave us a comment or
Speaker:subscribe and we will see you next
Speaker:week.
