448- The Examined Leader Retires the Old Playbook w/Rajvir Madan

Phil Howard & Rajvir Madan

448- The Examined Leader Retires the Old Playbook w/Rajvir Madan

THE IT LEADERSHIP PODCAST
EPISODE 448

448- The Examined Leader Retires the Old Playbook w/Rajvir Madan

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Short Clips

Episode Highlights

Rajvir Madan

GUEST BIO

In this episode of You've Been Heard, Phil Howard speaks with Rajvir Madan, SVP and Chief Digital and Information Technology Officer at Arcutis Biotherapeutics, about the habits that widen the gap between a transformation plan and the result it delivers. Rajvir starts with the examined leader: someone willing to separate personal worth from project outcomes, question a familiar playbook, and prepare for the effects of a decision before rollout.

The conversation moves from personal patterns to culture and operations. Rajvir explains why values need operating principles, why activity counts can hide weak outcomes, why a strategy must say what the organization will stop doing, and how metrics shape incentives. He also makes the case that missing data deserves analysis, because the people who do not respond can tell leaders something the submitted answers cannot.

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Show Notes

Episode Show Notes

Navigate through key moments in this episode with timestamped highlights, from initial introductions to deep dives into real-world use cases and implementation strategies.

[05:33] Rajvir explains how grades and project outcomes became tied to personal worth, and why leaders need to separate worth from work.

[08:52] He frames the transformation failure gap through three areas: looking inward, organizational culture, and operations.

[13:18] Rajvir introduces pattern recognition and asks whether an old playbook fits the context of a new organization.

[15:31] He explains why leaders need people around them who will challenge a familiar pattern and debate its fit.

[17:24] A failed AI drive-through order becomes a lesson in testing decisions under real-world conditions.

[22:52] Rajvir adds two inward-looking tests: prepare for unintended consequences and examine the history you bring into the room.

[27:24] He shows how values become useful only when leaders turn them into specific operating principles.

[31:55] The conversation replaces pilot counts and activity reports with questions about customer, employee, and business outcomes.

[33:12] Rajvir describes feedback loops that let frontline employees and customers signal friction before a rollout causes more damage.

[34:48] He argues that strategy requires a clear statement about what the organization will stop doing.

[37:43] Rajvir explains how measures shape incentives and turn teams toward activity or outcomes.

[40:13] He closes the data discussion by showing why survey non-response is part of the evidence.

KEY TAKEAWAYS

Leaders make better calls when they separate personal worth from project outcomes and test familiar playbooks against the current context.
Culture can absorb change when values become specific operating principles and people have safe feedback loops for reporting friction.
Operations improve when strategy states what will stop, initiatives connect to business outcomes, and measures reward value instead of activity.
448- The Examined Leader Retires the Old Playbook w/Rajvir Madan
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TRANSCRIPT

448-Rajvir Madan

Host: Phil Howard

Guest: Rajvir Madan

Phil Howard: Welcome to You've Been Heard. You've been on the show before, but

what's the update in your life? What has changed in; I don't know. However long

it's been a year or two years, let's just go down; how much can change in

someone's life in a couple of years?

Rajvir Madan: Yeah. So first of all, you gotta start with the family man. So the

kids are, growing up, And, I took a trip to India with, my eight year old

earlier this year, and It was fantastic to get him to experience the culture in

India, get him to meet the extended family. I think that was awesome.

Phil Howard: So he got completely taken care of the entire time he was there and

got to see, literally another world. How does the culture differ just from a

business culture? Just curious, here and in India, or it doesn't even have to

just be business. you've seen both sides. So what's, profound to you or what do

you see that's different? I mean, obviously a lot of things are the same. We're

all humans everywhere. And that's probably one of the first things that people

realize. But, what's different?

Rajvir Madan: Yeah. I think what's different is from a business culture

perspective, I would say that, the American culture and the American business

culture tends to be extremely direct. and, at least in my opinion, I think it's

extremely direct and, feedback is welcome. in most sort of settings that I've

been in, I would say that, it's completely okay to have that debate, to have

that dialogue, to have that discussion before you sort of get to, an important

decision. and, I find the Indian business culture to be extremely, hospitable. I

don't know if you've ever, traveled to India. and it's a very hospitable

culture. It's a very sort of community based, culture, for instance. and that

has its implications on how you deal in a business context there.

Phil Howard: I haven't traveled to India. I have many friends from India,

Pakistan, Bangladesh, Morocco, all of the Middle East. And what I've noticed,

and I don't know if there's any, parallels to this that I've noticed when you

get outside of the United States, depending on what country you're in. There's

definitely more. I don't know if I want to say political decisions that come

into play or a lot more of, kind of who you know matters. I think competency

matters, I think degrees. I think people in foreign countries tend to be very

degree heavy. I think that matters a lot more. In America, I think degrees

matter, but I think competency and your ability to do something and more prove

it by the numbers matters. I think hardcore numbers in America, but I find that

other countries degree heavy, who you know matters. And I don't know if that's

kind of reading between the lines of, maybe more welcoming. I think probably

what I said sounds negative, but maybe you can shed a positive light on it.

Rajvir Madan: Yeah, no, actually I would agree with you. I think, growing up in

India, at least I went through sort of a British educational system and I would

say grades really mattered. Education really mattered. Degree really mattered. I

think the last time I was on the show, I actually spoke to you about this

internal competition that I've had with my siblings over the years about who has

the most degrees and that was, something that was embedded, in our upbringing,

with my dad and he always instilled the value of education. So I totally agree

with you on that. and yeah, I would also say that, this.

Phil Howard: Discipline, the disciplinary system over there might not be as

controlled as America as well. There might be some harsher discipline. I'm just

imagining, I don't know, like if you didn't, if you came home with a bad grade

or something, I just can imagine.

Rajvir Madan: I think what's important is, growing up, I would say that one of

the things that was embedded in me was, sort of my worth and my value came from

the grades that I got. and, as we get into the podcast today, I think this one

concept that I want to sort of talk about is this notion of the examined leader.

and it's about how you create sort of self-awareness. and a lot of that

self-awareness that I've created for myself has been, based on sort of, going

through therapy for the last ten years. And there's been reasons why I've gone

through that. And one of the big sort of revelations that I had therapy was this

notion of, I need to separate my worth from my work, from my grades. and I think

I've been caught up in situations at work where, if there's a project that's

failed, for instance, I've sort of taken it as a personal failure. then I've

often sort of told myself, oh, I don't want this project to fail. So we'll keep

going with this project. We'll keep trying to implement the system, for

instance, and you have to step back and think about why you do that. Because in

a lot of cases, what you're unable to separate is this notion that you need to

sort of separate your work from your work. And, I've had to sort of tell myself

that this is not a reflection of my work. this is, not a reflection of my worth.

And what I need to do is sort of, make the right call for the organization. And

sometimes the right call for the organization might be stopping that project,

killing that system or whatever it is. Right. And I think that, when you're not

able to separate the two, you sort of get into making decisions that

unfortunately might not be the right decisions for the organization.

Phil Howard: I love it. It's selfless. And I think from a selfish or a personal

perspective, I think your self-worth is going to come from me. Right. So we

could spend a lot of time. And I'm just saying this because a lot of us and just

being an American, like, yeah, our self-worth is our career and all these

different things. And meanwhile, our family suffers. So, with that being said,

what you just said from a team perspective and from a company vision perspective

or from a, I guess, a culture, I think it would be more of a culture perspective

is that, team wins. It's not just about, self and, how you grow and I think what

you said is so important because high achievers, overachievers don't want to

give up. They really don't want to have a project that fails. But with that

being said, how do we close the failure gap in an industry where most projects

go twenty percent, over budget? So many Black Swan ERP projects, so many things

not delivered on time. shadow IT, shadow AI. I guess, how do we stop? Or how do

we figure out where it breaks down and how do we close the gap? Because I would

love everyone to listen to this and all the failures to end.

Rajvir Madan: Yeah. And I think let me sort of set the context. Phil, I just

read a statistic not too long ago that said about seventy five percent of

transformation projects, actually do not end up delivering the outcomes that

they intended. So let's sit with that just for a second, right? This is not sort

of underperform a little. This isn't five percent, fifteen percent, even fifty

percent. This is seventy five percent. So, seventy five percent of them do not

deliver the change that they promised within the organization. Right. So,

clearly there is this sort of gap between what your intention is and then what

you've actually, delivered in terms of outcomes for the organization. Right. And

I sort of look at that gap, I've sort of been doing this now for a little over

twenty six years and I've been leading a lot of transformations. and I think for

me, it sort of comes down to three big things. The first thing that it comes

down to is sort of looking inward. I think as leaders, we have a set of

fallacies that, we need to work on. and I'll get into some of those in just a

second. I think that a good strategy or a good decision, doesn't always sort of

land the outcomes that it's supposed to land. And, as leaders, we need to think

about how we can contribute to closing that gap, closing that divide. Let's say.

I think the second, sort of pillar of how to close that gap is really around the

culture, of an organization. And I think that for me is, you have to think about

the culture of an organization and whether it's actually going to be ready to

absorb, the transformation and the change that you're looking to roll out. and

is the culture of the organization going to embrace it? Is it going to tolerate

it? Is it going to throw that change out? and how are people going to react when

that sort of change lands on them. Right? So that's the second piece of it. And

the third piece of it is really around sort of the operations, right? So, how do

you spend your time? How do you spend your money? How is data used? and if you

think about things in those three buckets, and we can get into more detail

around those, I think that's how you really start closing that seventy five

percent gap that sort of currently exists today.

Phil Howard: First of all, looking inward to ourselves to see where our own

blockers are. We've got, a cultural challenges. I guess the culture piece too,

though, is like, even if once we look inward and we find our own problems

ourselves and you're saying, okay, what are the problems of the culture now?

What would be preventing that? I guess my question to you is just challenge you

just based on what you said earlier, is you've looked inward to see what your

issues are, but whatever that change is. Why essentially, should the change or

even the spark or the spark of change even, where is that coming from to begin

with? Is it coming from you? Right. So like, how are we even coming about to

that? We even want to do any type of change or transformation to begin with? And

should the idea really be coming from you, or are you gathering this from all

different types of things?

Rajvir Madan: Yeah. So when we think about change sort of in general terms,

everything around us is changing. I mean, think about the impact that AI is

having on each one of our companies. And that's driving us to change how we

think about our organizations, how we think about, generating incremental

revenue, how we think about generating cost savings and productivity

improvements, right? so change is the only constant. There's always change

that's hitting us. I would argue that over the last couple of years, the speed

or the rate of change has gone up exponentially with everything that's happening

related to AI. and as leaders, if we're not ready to sort of, embrace that

change and to become change agents for our organizations, we're not going to

have that leadership seat anymore. I mean, there's already companies out there

like, there's Walmart, there's Adobe. I can get into a couple other companies

that have pushed out leaders within their organizations because those leaders

were operating from a previous playbook that wasn't ready for how change needs

to be thought about and how transformation needs to be thought about in, this AI

era that we've just kicked off over the last couple of years.

Phil Howard: So true. Okay, let's just start on your first three to five bullet

points on how to look inward for people that like, because we only see what we

see. We only know what we know. We don't know what we don't know. It's basically

kind of a really shallow way of looking at it. But how can we self-diagnose or

do we need someone else to do that?

Rajvir Madan: Yeah. So let's, start sort of looking inward, right? And I'll give

you, the first sort of tool that I want to sort of think about is this notion of

what's called pattern recognition. And it's not sort of the statistical or

mathematical definition of pattern recognition. So at times, your brain can

almost be, manipulated, consciously or subconsciously to focus on a pattern that

you have seen before. Right? And as leaders, often what we do is we walk into

organizations and we try to apply a previous pattern to that new organization

without sort of recognizing that the new organization that we're in has a

completely different context. we think that an old pattern can work in a new

environment, let's say. Right? So what works for Lockheed Martin is not going to

be what works for SpaceX, for instance, right? Two very different contexts. So

our brain has this tendency to sort of go on autopilot, and take previous

patterns and start to apply them. even though the context is very different and

this is one of the tools that I think about quite often, which is, is the

previous pattern is the previous playbook really applicable in the context that

I'm in? and if it's not, don't apply it. and this is what I call the

anti-pattern. So sometimes you have to sort of leave the old pattern in place

and almost think about what the pattern for the new organizations needs to be,

which is the anti-pattern. That's one thing that I think about that leaders sort

of constantly have to do and constantly have to sort of think about as they're

operating in new organizations. So that's one of the tools that I think about.

Phil Howard: There's a lot of challenges and problems that come up with that.

One, they might only have one pattern, Two, they might not be bold enough or

believe enough in themselves, or be creative enough to even be able to realize

and see something doesn't feel right here. And I think that that's what it

really is, is I think that sometimes people get fooled and then that's how we

end up buying things that that's how we end up buying shiny objects. Yeah.

Because someone comes in and they're like, this is it. This is the solution. And

this is how we end up with a tool first.

Rajvir Madan: And I think, what's important in sort of situations like that is

to really, surround yourself with people that will tell you that, this is a

pattern that needs to be applied with caution in this instance and why it needs

to be applied with caution. Right? And I think what good leaders do is, they

surround themselves with people that are going to, give them that feedback that

are going to give them that coaching and say, this might actually not work here

or yes, it might work here, but this is what you have to think about. And I

think, that sort of notion of feedback and that notion of sort of robust debate

that comes with surrounding yourself with people that are not going to just say

yes to you, I think is really important because I've seen a lot of

transformations fail because leaders did not want to listen to feedback from

other individuals around them.

Phil Howard: One of the most effective things, or one of the best pieces of

advice I actually got was along that line kind of the opposite. But I think it's

the same. And that is basically trust your instincts. Like just because AI says

something or just because so and so said it, or because the director of sales at

Salesforce said it, or because this program used this or this guru said that.

Yeah. you kind of have like a good feeling when you're in your environment, you

understand your culture really well and you understand your people well, you

kind of have this like little feeling that's like, something's not right here.

It doesn't fit. Like that needs to be changed. Like don't use that. Even though

the prompt popped this out, like maybe eighty percent of it's good. But the

other twenty percent, I think a lot of times people might doubt their own

instincts. I don't know if that's in line with what you're saying, but sometimes

I really needed someone to tell me, that doesn't work here. And you're right,

actually. Like that won't work in this situation. It works in ninety nine

percent of the situations, but your instinct that it's not going to work here is

correct.

Rajvir Madan: Yeah. And, I think part of it is like, you need a mechanism to

test some of your decisions, with groups of people or with individuals. Right.

and this is, example from not too long ago, I think it's been about a year or

so. I drove up to a Taco Bell and, it was about ten minutes before I needed to

pick up my kids and I was hungry, let's say. and there was a little sign outside

the drive thru that said, AI is lending a hand. and, there was a part of me that

was super excited about it, given the work that I do, and there was a part of me

that was like scared about what was about to happen. it was a rainy day. It was

a windy day. And, I sort of gave it my order and, I just wanted a crunchwrap

Supreme and that's what I told it and it, didn't really understand what I was

saying, because of the rain, because of the wind. And, next thing I know, it

finalized a twenty five dollar order for me, with four different items in the

bag. I was late to pick up my kids, but I was sort of asking myself the

question. I'm like, that's like, how was this tested? Like a decision was made

to roll out AI. But, was it really tested around conditions like, wind and rain

really bad. and there's actually a lot of, sort of media around this, they

actually accepted that. and I think the comment that their chief technology

officer made was sometimes AI works and sometimes it doesn't. Well, I don't

think you want to roll it out when it doesn't work.

Phil Howard: Seventy percent of the time AI works in, in a tested like in a very

intensive environment. I actually had a really good AI experience the other day.

Really, really good. And I've reached out to the CTO and I think I need to keep

saying this over and over again until he decides to come on the show. And they

did really, really good on booking my appointment, following up, listening to

me, making sure I was heard and not a single human touched it. MM. I went to

their website. I like really vibed into this like little chat bar. Like I just

hit like transcription. Right? I was like, look, my air handler is not working.

I already, turned it on and off. I already went to the breaker panel. I shut off

all the breakers. I pulled out all the main like plugs at each unit outside. I

checked for dead mice. I like went through the whole thing like I took the front

panel off. There's no lights, the panel. There's no power going to this. I was

like, just this whole long paragraph send I get back like, Phil it sounds like

you've been pretty thorough with what you've checked already. Let me make sure I

understand you correctly. You've done this, this, this, this and this and all of

this. So definitely a technician needs to come out this Tuesday at ten o'clock

work or would Wednesday at three pm work better. And I was like Tuesday at ten

o'clock. And I was like, okay, we've sent you a meeting reminder. You'll get a

text message reminder as well. And we'll make sure someone from the office on

Monday follows up right away. This is Sunday night, right? I was like, blown

away. That's awesome. And service Titan, whoever you are, service Titan, I need

you and I called him, I was like, what do you guys use? They're like service

Titan. I was like, we're on like a beta. And I was like, of course you're on a

beta because it's an AI thing. Like, of course you're on beta, whoever you are,

service Titan, CTO, CIO, director of, development or something, please. Come on

You've Been Heard. We're giving you a shout out right now. It's free. You don't

even have to pay for this. And we're telling you that you're awesome and you're

actually using AI correctly in a world where ninety five percent of all AI

projects fail, according to the MIT study that was released over a year ago. And

hopefully we're better right now. They all become black swan projects. They all

fail, and people spend a ton of money. And this should be an advertisement that

someone pays me for. So and I immediately called my other Hvac friend Hvac. You

gotta say it like that down in Philly. And I was like, dude, you gotta use this

because how many other guys are up in the ceiling? they answer a phone call.

Then they're like, yeah, I'll be there tomorrow or, and then they forget because

they just can't do all this. They need service Titan.

Rajvir Madan: Yeah.

Phil Howard: That's awesome. Okay. Why do they fail? So we've looked inward. Do

we have like some five bullet points, like some questions we could ask

ourselves? But, what bullet points should we have? Or should we be asking

ourselves when we want to look inward?

Rajvir Madan: Yeah. So I would say the first bullet point is really around this

notion of pattern and anti-patterns. So really asking yourself whether a

previous pattern applies in the context that you're in and why it might apply or

why it might not apply. Right? So I think that's one of the things I think the

second.

Phil Howard: About patterns of just issues, like every time this happens, I gain

twenty pounds and start eating again. How about bad patterns like that? Or every

time this happens, I seem to go start looking for a vendor first instead of

talking to my end users first. Are there patterns like that?

Rajvir Madan: There's patterns like that. And I think that, to your point,

there's good patterns that you want to reapply. and I think you have to ask

yourself whether you can reapply that pattern or not. and then there's bad

patterns that hopefully we've learned, never to apply because they just lead to

bad outcomes. But I think your point is a good one, which is we have to learn

that there's good patterns and bad patterns and good patterns don't always get

applied. Bad patterns, should probably never get applied because they normally

do not work in most situations.

Phil Howard: What do I habitually do? Also, I think a lot of people will

overanalyze or paralysis by Overanalysis. I think there's some people that might

get into that.

Rajvir Madan: Let me give you a couple more bullet points, please. When you're

making a decision. I think you have to sort of not only ask yourself, did we

make a smart decision? And as leaders, we are trained to make good decisions.

there's a million books out there that teach you how to make good decisions.

There's all these decision making frameworks, there's Raci, there's Di, I can

name a few of them. Right. But the question you have to really ask yourself is,

are we ready for what will come from this decision? Right. And I think that gets

you to think about the unintended consequences of that decision and how that

decision is going to land on people, on your customers, on your consumers, on

the culture of the organization, on systems. How is it going to impact

processes? Right? So thinking about the ripple effect of a decision is one of

the other tools that I sort of, get leaders to sort of think about in this sort

of inward context, let's say. and then the other thing I would say is that, this

notion of sort of self-awareness, which I have gained through a lot of work I've

done on myself, including therapy. I think that really gets you to sort of think

about your upbringing. It gets you to think about your cultural context. It gets

you to think about your fears and your ambitions and what causes you anxiety and

doesn't cause you anxiety, for instance. Right? Because guess what? When we show

up in a meeting, when we show up at work, we are bringing all of that with us.

We are bringing our upbringing with us. We're bringing our cultural context with

us. We are bringing our fears, our ambitions, our anxiety with us. Right? So

that shows up in the room that is in the room, whether you like it or not. And

having that level of self-awareness is really important.

Phil Howard: Any suggestions or books or methods or anything like that?

Rajvir Madan: Find a great therapist. I've tried to find a good book on it, and

I think a lot of books that are out there go over interesting frameworks. They

give you interesting tools. But, I think the process of engaging with a

therapist, that therapist is going to ask you a series of questions that are

going to get you to think. And that way dialogue is really, really important. A

book is not going to give you a two way dialogue. And I would say that's where

sort of actually having that human interaction is going to be really, really

important. this is one of those things I wouldn't use ChatGPT for or an AI. No,

no. I think a lot of people use ChatGPT for therapy. And, the kinds of questions

a good therapist will ask you, ChatGPT is not going to be able to ask you those

questions.

Phil Howard: I think a good resource is Psychology Today. I think the articles

there are like, first of all, I think you could find a good therapist there too.

I think there's probably some kind of like finding tool or something like that,

but the articles and stuff really bring up kind of like some in depth, like

topics and understanding of how humans operate. I think I went to a therapist

when I was like under a lot of stress as a business manager and had like, an

insane staff and really, really strict budget and a very, very high achieving,

senior executive manager. And even though I was like one of the best, right. and

I was performing like highly performing. And I found out later on that this

person told me I was like one of the best. I thought I was the worst. like when

you're the best and you come into work every day and you feel like you could do

one thing and get fired, that's a problem. Yeah. And it's just like, that level

of stress is like, I don't ever want to experience ever again in my life.

Rajvir Madan: That's a good segue into culture, right? And I think that's part

of what going through a process of self-awareness and therapy sometimes is about

right. we all have a work history attached to us unless you've just, you know,

graduated from college or high school or whatever it is. I think we all have a

work history. attached to us. And we also have a notion of work sometimes that

we've seen, from people or, around us, whether it's our parents, whether it's

our uncles and aunts or whatever it is. And I think again, that is part of our,

upbringing and those are things that we really have to dissect as we go through

this process of becoming much more self-aware.

Phil Howard: You were thinking culture can tolerate change. So what we're

supposed to be talking about is closing the failure gap here. So and we might

have to have some kind of concrete example here to kind of try and make some of

this come clear. In other words, I don't know whether it be an ERP change or

some typical thing that everyone goes through, it's like, okay, first of all, we

already looked inwardly. we know that maybe my recipe for success at every

company is not going to apply here to this one. And we can't just use SAP

everywhere in the world or whatever it is. I don't know. can my culture tolerate

it?

Rajvir Madan: Yeah. So one thing that I think about related to culture often,

and I think this is where sort of culture either, expands the failure gap or

actually shrinks. It is this notion of, we've all worked at companies that have

values. and they post it on the walls and, on the hallways and all of that good

stuff. Right. And then I see, behaviors within that organization that actually

are very counter to those values. Right. I've seen like, a value around respect,

for instance. And then, the company tolerates individuals that are not

respectful to each other. and I think when you start to see this misalignment

between a value and the actual behaviors that occur within that organization,

that to me is a telltale sign of the fact that, this culture is not ready for

change. because on one hand, you're preaching something and on the other hand,

you're practicing something very different. The other thing that I sort of think

about, I think coming back to sort of, recipe and let's stay on this, topic of

values is I find values to be important, but at times they're very lofty, for

instance. Right. And they're not specific enough to actually guide some of your

decisions and guide some of your behaviors. And let me give you an example of

something. I think if you have a value that, says that the customer is always

king or queen or the customer comes first, let's say, right? Let's say that's

your value. you might end up making decisions that are counter to your business

strategy. that might put the customer first, right? But this is where this

notion of operating principles comes in where you say, yes, our value is that,

the customer is first, however, we always, in a situation where, and, a staff

member or a team member or an employee has to go and do something that is

unethical to satisfy the customer, we will not do it right. And I think that

gives you clear guidelines around how to apply those values and specific best

practices and or principles around, how far those values should go and how far

those values should not go. And I think this is where I've seen organizations

either succeed or not succeed, which is they really distill those values down

into operating principles. and I think those operating principles really gets

you to sort of, make sure that you're aligned with how you think about that

value and how you sort of, actually show up in terms of, how that value sort of

shows up within the organization. So that's one piece of it around sort of

values and operating principles. I think the other piece that I sort of think

about is in a lot of organizations, and I think this is a great example, maybe

one, we can talk about related to sort of ERP, but I think it applies more

widely speaking, is this notion of sort of activity versus outcomes, right? I

think historically we have been very fixated on measuring activity. Right. How

many meetings, how many initiatives, I think even with like AI transformations,

for instance, I think a lot of leaders go to their boards and, their senior

management. And instead of talking about the value that those AI initiatives are

generating in terms of dollars or productivity improvements or whatever it is,

they talk about the number of pilots they're running, for instance. Right. and I

think there has to be this shift between sort of thinking about how busy we are

as teams versus thinking about what outcomes and value that team is actually

generating and what impact it's having on the business. And I think that is a

cultural shift that not many organizations sort of often, make. And then I think

one of the other things. And there's many more that we can get into.

Phil Howard: But one of the other let me just make sure I understand it

correctly, though, because I think a lot of the summary of that is, when it

comes to values or when it comes to activity, for example, is that we're being

specific and then we're aligning whatever specific activity to an actual

outcome. That's right. And I mean, for the thirty projects that might get thrown

at any IT leader, how many of those thirty actually deliver to the bottom line

or are helping alleviate the number one challenge that's holding the business

back from scaling?

Rajvir Madan: Exactly.

Phil Howard: Questions we can ask to make sure, should we be measuring the

activity versus the outcome here? Or questions we should be asking around

measurement?

Rajvir Madan: Yeah. The questions we should be asking is what changed for the

customer? What improved for employees? What measurable outcomes are we actually

going to see? Those are the questions you should be asking. Not how many pilots

you're actually running within the organization.

Phil Howard: Where's the disconnect for a lot of these people? What's the number

one thing they should be measuring an activity up to or like, is there just like

some basics that we can just like make it third grade for that everybody to me

it is because I stayed back in first grade. So to me, like business has to be

that simple or I wouldn't be successful.

Rajvir Madan: I think the simple question is like, this activity is in service

of what business goal or what business outcome. And if you're not able to draw

that connection between an activity and a business outcome, you might want to

tell yourself to stop that activity because it's not resulting in a, well,

either stop the activity or ask someone the question that says, I'm struggling

to connect this between like, connect.

Phil Howard: The dots, drill down, be specific, drill down and be specific.

Okay. Super awesome. where do we want to go next? Because honestly, we could

talk about all the stuff that we need to talk about, probably over a series of

ten shows. Psychology alone is like, the psychology of, should we go see a

therapist? And what's the actual state of it? Leaders in general is like a whole

podcast.

Rajvir Madan: It is, and maybe I'll wrap up the culture section by saying, I

think another sort of sign for me of a healthy culture is feedback loops as to

whether they exist or not exist within an organization, right? So, do frontline

employees feel safe telling you when something isn't working. do customers have

a way to signal friction that actually gets heard? do you review unintended

consequences regularly? when you're sort of rolling out a new initiative, let's

go back to our Taco Bell example. Like did someone think about what the

unintended consequences were? And in a lot of cases, I bet, I've seen this in a

lot of organizations. I think there are actually people that know what the

unintended consequences are going to be. And sometimes they don't have a voice,

or they're not talking about what the unintended consequences are likely going

to be or how to figure those out. and I think that's not a sign of a good

culture because you want to hear about these problems. Actually, before,

Phil Howard: The Taco Bell thing is laughable, to be honest with you. Yeah. what

that tells me is that there is someone that was like, AI is going to make us

rich. Yeah. We're going to be able to to cut back, one hourly employee per, or

whatever per thing. I'm okay with the self-checkout at Walmart. I really am

because it works. Yeah. But for some reason, when I go to stop and shop, yeah,

it's everything I ring up is like, beep. The light goes on. Someone's got to

come over and like, check the thing. So I get so frustrated and like, I go to

the one person that's a live line, like a live person and they're like, we can

go over to self checkout, I can show you. And I was like, no thanks.

Rajvir Madan: Yeah. So I think let's maybe shift gears a little bit towards the

operational side of it. And I think sort of good operations actually helps you

close that gap as well. And when I think about operations, I sort of think about

three different areas. I think one is sort of how time and money are spent. And

this gets into this conversation about prioritization, right. and I think, you

really have to ask yourself, are we investing time and decisions with the

biggest blast radius that are actually going to have the most impact for the

organization, our customers, our consumers, our employees? Right. are we

allocating our resources, where it matters the most? and I think most

importantly, a strategy professor of mine once told me, he said a good strategy

is, knowing what to say yes to, but equally importantly, knowing what to say no

to. Right. and I have seen a lot of strategy work done, a lot of strategy decks

put together, and very few of them actually have a clear statement around, this

is what we are going to say no to. and I think that for me, prioritization

struggles often at companies because you don't know what to say no to. what to

say yes to in a lot of cases. But when you don't know what to say no to, people

work on the wrong things. So I think that's about.

Phil Howard: Just one point to that, one point to that every great coach that

I've had and I've spent a lot of money on this stuff. Every single one has said

it's about what we're taking off your plate.

Rajvir Madan: Exactly.

Phil Howard: It's about what you're not doing. then my right hand man, Greg Le

Dall, the Frenchman, he knows. No, Phil, we're not doing the info tech better

than info tech IT leadership, score card, app that we're going to build and give

away for free. Like, no, we're not doing that right now, but it's awesome.

Rajvir Madan: I know.

Phil Howard: And look what I've, coded and look at all the research that I did.

And, but Infotech shouldn't be charging for that. It's ridiculous. We can give

it away for free. No, Phil.

Rajvir Madan: Awesome ness doesn't equate to business value. Right. Some of the

things that are not awesome are actually quite simple to do, actually generate

more business.

Phil Howard: I could not agree more. Yeah. The most boring things in the world

make great money, and you have to show up every day and grudgingly do this thing

and you will make money. I try to tell my kids that all the time, whatever that

book is, it's like, do what you love and you'll never work. Another day in your

life is a load of crap. It is.

Rajvir Madan: And by the way, follow your passion, I think applies when you've

made enough money in life. Then I would say go follow your passion. Otherwise,

in a lot of cases, there's some hard decisions sometimes you have to make with

sort of, sustaining yourself and your family versus, what your passion, allows

you to do.

Phil Howard: Agreed. One hundred percent. What are we ending with? You got the

final.

Rajvir Madan: I'm going to end with two final thoughts. I think the two final

thoughts I'm going to end with is when I think about operations, I think about

data. We haven't talked about data at all today, but I think data is sort of

very, interesting, I have some principles around how I think about data. I think

one of my sort of interesting principles around data is what you measure, you

become. And often the measurement follows the incentives, right? So, I think

that in a lot of companies I work for, if you measure, the number of tickets

that your IT team or your service desk is actually solving for, then that's what

you become, you become a very activity driven organization, versus measuring the

outcomes that those tickets are actually generating, for instance. Right. and

then, if you have a measurement around, and I've often seen this with like sales

reps, for instance, like, in previous lives, let's say sales reps were measured

by the number of calls they made or the number of stops they made at sort of,

doctor's offices, let's say. Right.

Phil Howard: Activity, activity, activity.

Rajvir Madan: Activity, activity, activity. But more importantly, they told

themselves that they're incentivized to drive activity, but they're not

incentivized to drive revenue. And, your measurement dictates often what the

incentives are, for you. and that can create a misalignment for you as an

organization. And that again, creates a wider gap.

Phil Howard: Yes, we're measuring answers to questions. Mhm. we're definitely

measuring podcasts done with the right people. Mhm. And when I say measuring the

questions, one of the questions that we ask a lot is when it comes to your CSP,

VAR, MSP, the seeds of the world, what's your single biggest frustration,

problem or concern? Mhm. And surprise, surprise, what we find is that we feel

like people are pushing boxes. They're just trying to push a product. They get

paid an extra few points on. We don't like the people that are the Swiss Army

knife, vendor to everything because they don't do anything well, but they do

everything kind of mediocre. We'd rather have people tell us what they really,

really do well. And if we measure that, we really, really find out what matters

most. Yeah. We also find out who the real IT leaders are. We actually find out

that people are that actually have a seat at the executive round table and are

heard. And so we measure a lot of things. but it's amazing. You can measure,

believe it or not, human language and there's models and patterns to it.

Rajvir Madan: The other thing that I find really interesting is sometimes a lack

of data is data itself. like think about employee surveys just for a second,

right? Yeah. if seventy percent of the employees respond to a survey and thirty

percent of people don't, there's data in why thirty percent did not respond to

that survey. So lack of data is also data. And a lot of people analyze the data

that they got, but they don't analyze the data that they did not get.

Phil Howard: You just made me have a leap in faith in the data mind blowing

thing, because we talk about it every day, like data is everything. It's the

gold, it's the new whatever we talk about that. But, I think you just helped me

hit like even just a new level of, mind blowing thought when it comes to data.

Now, as far as AI though, and all of the things that we've kind of been poo

pooing a little bit. Yeah, I do think there is an option here. Yeah. You should

build along with your philosophy of, I think there's a potential I t a I

psychologist agent that could actually help you look inward, ask questions,

break patterns, ask you if you're, culture is ready to tolerate the change that

is coming up. And then make sure that you say no to whatever that is because

it's just going to screw up the budget anyways. So the first thing it's going to

do is ask you this question. It should just say no first. First of all, no, it

should say no to you. Throw this project away fifty times. And then if you keep

coming back like, okay, what pattern do you want to throw at this? And can your

culture even handle it? Maybe. Might even want to go backwards. We might want to

say no first, then hit the culture. And then is the culture ready for you? And

are you going to screw it all up and break the culture anyways? Because you come

in with some crazy pattern that's just not going to work.

Rajvir Madan: Yeah. And you know what? You hit on a really interesting point,

which is around sort of operations. One of the other things I think about is

like how resources are allocated. And I specifically think about human resources

here. Often I have seen like when you start a transformation, you like, you hire

like tons and tons of people within the organization to actually drive that

transformation forward. But you haven't really defined what their roles and

responsibilities are and what they're going to do. And then those people end up

creating busy work for themselves and for the rest of the organization. And that

actually deviates from the mission of the transformation because instead of

actually focusing on what the organization needs. You're creating busy work.

just to validate your existence within that organization.

Phil Howard: Yes, yes, yes. it's so true. Setting clear expectations, making

sure that we communicate the job's not easy. you make it. Look, I guess I would

like to say easy, but I guess it's probably a career full of, failing forward

and a lot of mistakes and hard earned battles won. So, Rajvir, it's been a

pleasure having you, having you on You've Been Heard and You've Been Heard.

Rajvir Madan: Thank you. Thank you Phil for having me today.


448-Rajvir Madan

Host: Phil Howard

Guest: Rajvir Madan

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