Fireside Chat w./ Prakash Raman

By Josh Jones-Dilworth

Ed. Note. Every time Prakash and I get together, the conversation just flows. For this piece, we sat down for a fireside chat, which has been transcribed for your reading pleasure. Prakash is one of the deepest thinkers I know about what makes humans tick and what we need to be great at work together.

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Prakash Raman serves as a high-performance coach to CEOs and executives at leading public and private Silicon Valley companies. Prior to coaching, Prakash worked on Wall Street (Merrill Lynch), a non-profit (focused on corporate diversity), brand management (Kraft), a failed startup (Miso) and big tech (LinkedIn). At LinkedIn, he spent 5 years in Executive Development where he coached and facilitated for LinkedIn’s senior executives.

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Josh:

Hello and welcome! So, to get us started, here’s the frame. I think what’s so interesting about coaches is you all work with these ultra high capacity leaders and you see patterns. And most leaders, I think, feel pretty lonely and out alone. Being part of a pattern is actually soothing. Being placed in time and in a trajectory is soothing. You’re not alone.

Prakash:

Totally, totally. That’s a great way to put it.

Josh:

Prakash, you and I were on a walk the other day and really we were talking about polarization and we were talking about how on some level the workplace is the one place where we can all still get along, but it seems like even the workplace has been infiltrated by politics and culture wars, and it’s getting harder and harder to have real, authentic, additive conversations.

Prakash:

In my sphere of work and working with leaders, like you said, I’m finding so much of the same thing applied to leadership. And more specifically, I think one thing that’s becoming clear is we all have certain mental models and those mental models create some level of certainty, right? So we cling to them.

Josh:

Right!

Prakash:

Versus, “Huh, maybe I could learn more. Huh, maybe actually there isn’t a complete right answer, but there are trade-offs.”

It could be how to hire, for example, and someone can have a very right or wrong way of being, for that hire, based on their match to our idea of the complete right hire. And I think the dangerous thing comes in how we orient ourselves towards people and what new, unexpected things they might bring. These days, we’re closed off to the unexpected. And we keep trying to force our expectations onto reality. Usually reality doesn’t cooperate.

This happens a lot with engineering and sales hire in particular, where the templates or expectations are intense, and in those domains, it’s common to see folks deploying a set of stereotypes that are absolute in nature.

These leaders are not, as one would say, the human-first. They’re relying on sets of pre-judgments about who is right for th0 ejob. Now, I’m not saying we shouldn’t have judgments. I think humans have to have judgment. And we can have expectations. But when that judgment becomes a good or bad or some absolute is where I find we start to fall apart.

Josh:

Agreed 100%. I sometimes talk about this as a procurement approach to hiring, or to anything else — going out and procuring the thing that matches my reality, instead of letting my reality be shaped by what (or who) shows up on a given day.

For me, it’s inseparable from speed, because when we’re trying to move so fast, we start to rely on heuristics and templates and these sort of cliches or these assumptions that are really, ultimately I think, a product of going too fast to notice or to choose the right vocabulary or to realize the conversation you’re not having.

Or, even to do the difficult work of holding things in tension.

My friend Jay Brenneman uses this awesome word all the time. Polarity is two sides that are in tension, but the idea of polarities is they’re not supposed to be resolved. They’re supposed to be held in tension and the tension is productive. The tension is energetic. The tension is something you surf.

Prakash:

Yeah, I’m seeing this a lot, Josh, too, it’s hard for us to hold tension. There are enough tensions in our life, so holding more tensions without certainty, especially in a data driven world, it’s hard and getting harder.

Josh:

Yeah. I think a big part of it is exhaustion, basically. So if we’re in a permanently VUCA world, I’ve been using that term VUCA and not everyone knows the acronym. It stands for: volatile, uncertain, complex and ambiguous, or VUCA. Maybe add a P at the end — we’re polarized, too.

And we’re tired. I know a lot of leaders, look, they have their wits about them and I think they understand the things that we’re saying and yet, when you’re exhausted, it can get the better of you or you can get a little lazy, or you can not be quite as meticulous as you want to be. I think that’s what’s so hard is the cumulative exhaustion.

I was on a hike in Jackson Hole a couple of weeks ago and at the top of the mountain the wind seemed to be blowing like wind has never blown before. If you lifted your arms, you might have flown off the mountain and it just felt really good. I just kind of just started to let COVID blow off me, let 2020 blow off me, and it wasn’t instantaneous but I had this incredible physiological sensation of letting go.

I think we’re also all holding onto the last year, the last 15 months, the last 18 months pretty tightly and I understand why and I’ve plenty of empathy for why, and none of us had the same experience, but I do also think we need to just start setting our 2020 baggage down on the table a little bit, putting it in its right place so we can walk forward.

Prakash:

Yeah, what do you think makes that so hard?

Josh:

Oh, I just think like, we’ve talked about this before, you and I, and I think I was even encouraging you to write a book on this topic and maybe we’ll get the book done one day!

I think that at least a lot of the leaders I know and work with and am friends with and share war stories with — we’re just very stuck in the present tense. And not in a mindful way. There’s hyper-vigilance — that would be my word, about right now — and what’s coming immediately next. Hyper-vigilance. It’s that sense of foreboding.

And I think it’s harder than ever to live or be in the future for spells as a leader because the present moment is so demanding. This is the very nature of crisis, and being in crisis.

Prakash:

Yeah, that makes a lot of sense. I know one of the things we talked about was, how do you help people reframe, right?

I have a lot of empathy for leaders that are moving a mile a minute, like yourself, and as you said, it’s hard to be mindful. You’re also not taught to.

Think about this. You go through school and somebody says, “Getting X grades gives you a big kudos and Y grades don’t. And then get into X college and then obtain Z job.” We’re conditioned to be outcome-driven, from an early age, so everything that we are talking about goes against our cultural training. And it is important that we keep talking about this dynamic, because it colors almost everything.

When you and I introduce each other, or if we introduce others, how do we introduce them, do I ever say, “Hey, Josh. This is my buddy Josh, he just gives a great effort all the time and he’s just very kind and compassionate and he just likes to put his all. He has a growth mindset?”

Josh:

No. We live in America so we talk about the outcome that we’re each going to get from the transaction, baby!

Prakash:

Right. So it’s very easy then, to say you become a leader and you’re maybe leading a few or a lot of people, and what do you do? It goes back to the outcome because that is what you find is measurable. So two things I think can be really helpful for us to maybe let go of that. One is acknowledging feelings and that we have feelings. We have feelings! They are real! And they factor into our lives and businesses!

Josh:

A radical idea. Ha.

Prakash:

A friend of mine, Marc Brackett, wrote a book called Permission to Feel. And it’s a beautiful book because it’s not something we’re taught.

The second thing, I think, is actually taking stock of those feelings and writing out what’s driving them. We’re all spending a lot of time doing a whole bunch of things, and if you were to ask any of us why we’re doing them, I don’t know that a lot of us have a solid, intrinsic answer.

Josh:

Yup. I love that. I absolutely love that. There’s a project that is ultimately being targeted at high school or early college age kids that immediately comes up for me when you’re talking about that, because I don’t think we can escape the fact that this stuff is baked into us pretty early.

It’s called the Mastery Transcript Consortium, which started out of a very innovative independent school called Hawken in Cleveland.

It is a collaboration amongst a whole bunch of top colleges and universities and a whole bunch of high schools. And what the colleges have said is, “Hey, we actually don’t like letter grades. We don’t like the transcripts you give us. They don’t give us the shape of kid in a way that helps us make good admission decisions. So we would like to move to a different model.”

So the consortium is a group of colleges and high schools who have been prototyping what it looks like to have a mastery-based transcript, a sort of evidence-based transcript, not of grades or outcomes but of work done and progress made — a multi-dimensional portfolio, in essence.

Such a transcript would articulate the shape of your work, the shape of your interests, how rare those pursuits are at the school, and would give examples of what it’s looked like in the real world.

I think getting rid of letter grades is a very controversial thing to folks who think, “Oh, that means we might be getting soft or somehow more permissive of middle performance.”

But I think actually mastery and mastery transcript concepts are more hardcore, in a lot of different ways. So that’s a really interesting idea that I think is secretly a fulcrum in some interesting ways for the conversation we’re having now.

Getting away from outcomes often produces better outcomes!

Prakash:

Yeah, well think about this, Josh. Let’s push it even further. I love that point of mastery. Think about this, if you’re a leader or a student, why have mastery? Why do you want it? Do you know why it matters to you to have mastery?

Especially as a leader, do you really know? If you were to ask a leader, “Hey, what does leading effectively look like to you and why would that matter to you?” they are likely to have a hard time. These are hard questions, right?

Josh:

It’s a really hard set of questions. Yeah, totally.

I think most people would immediately tie it back to the thing that they already hold dear, which is “I want mastery because I want to win.” Or, “I want mastery because it will allow me to get promoted or make my number.” Or, whatever it is. And I think you’re totally right. There has to be baked in to that idea of a mastery project, or mastery in any domain, the “why of why” you’re pursuing the mastery in the first place.

One cool thing, related, that a mastery transcript will effect in high schools and colleges, I think, is more thoughtfulness around one’s gifting and one’s calling. Because the letter grades are no longer there to serve as surrogates.

For me personally, for the record, when I think about how to answer your questions, it’s mostly because the pursuit of mastery gives me energy and makes me happy. And I always like to feel out and find where the edges are and I always like to be in that place where discipline is evolving in real time all around you. That feels like progress and evolution and that’s exhilarating and I’m sure that mastery has been good for me in my career, but I pursue it for fun.

Prakash:

Well, my experience of you, Josh, is that things like evolution, you said the word, things like being on the edge, those are actually aligned with your values. That is my experience of you.

When I think of my role as an executive coach, often a CEO is doing a whole bunch of things and wanting to improve on a whole bunch of things. A lot of my role, I think, is helping someone understand why. Why does it matter to them to do those things? If we get that part right, the rest comes along fast. The inner work is the hard part — the why.

Josh:

The inner work is extra hard. I love the Latin term telos, which means the “ultimate aim.” There are goals, and then there are goals!

Your telos is sort of your why, your theory of change, your vision, how you’re going to leave the world a better place and sort of what you really intend by your life, and I think you’re totally right, that inner work is really intimidating. And in the face of that intimidation, it’s really easy to just do the tactics of coaching and the tactics of leadership and the tactics of self-improvement.

A lot of leaders are not clear on their telos. I’m not clear on my telos, I’ll admit that right now.

Prakash:

Yes. The work you are describing is is a lot harder than the day-to-day challenges we face. We know how to execute things. Everyone you’re speaking with, all of the clients, all of your friends, super senior leaders, these are people who know how to get things done and getting things done. But are you getting the right things done?

Josh:

Love it. Okay, let me do the devil’s advocate version.

Let’s say I’m a casual observer of this conversation and I think:

“Well, Josh, you’re a high performer. You work with a lot of high performing teams. Prakash, gosh you coach and work with a lot of high performers and some crazy high performing teams. You guys are talking about a bunch of soft skills that sound to me a little bit like reducing ambition or taking it easy or not pushing so hard.”

The devil’s advocate worries we went soft and hippie. So how do you reconcile this emphasis with why and reframing, and slowing down, with high performance?

If I follow your advice, Prakash, is this going to result in me not hitting my numbers? Is this going to result in me not getting what I want? Is it going to result in poorer economic outcomes?

Reconcile the two with me, if you would, because I think that’s the pushback I’m most familiar with when I have this conversation with folks.

Prakash:

Right. “Hey, it all sounds nice and dandy. Understand your why. But how does that ensure I’m going to get the outcomes I want?”

Josh:

That’s it.

Prakash:

Yeah. It’s a great question.

I think it’s helpful to take stock of what your mindset is to begin with.

Are you doing this and taking the perspective that you are learning to get better? To your point of mastery, mastery comes in the form of excellence. You will hit your outcomes.

But if your mindset is, “I just have to hit the outcome,” you may actually not gain mastery. You may not build the capacity necessary to sustain high performance.

You and I know people who have short term, done very well. But they haven’t gained true mastery, or true excellence, and therefore it’s hurt them in the longer run. They were penny-wise, and pound-foolish, when it came to their own development, and it shows.

And, you’d be surprised how many folks I know and work with are doing things every day that work against the outcomes they actually want. Being so-outcomes-focused doesn’t have a clear correlation with achieving those outcomes, I promise you.

Josh:

I 100% agree.

Prakash:

If you believe that it’s just better for you to grind away, not know your why, and you’ll have the same energy and gumption with your customers, for example, even when you’re not sure of your why, if you believe that, okay. That’s fine. You just have to learn the hard way!

I had a client who, some of his challenges are in hiring. This is a pretty simple example, but it’s accessible and common. He wasn’t consistently hiring the right people, and there was a lot of turnover. And so much of his mindset was like “I’m looking for a person in the seat” and “I’m just not seeing the right candidates.”

The issue behind the issue was that he was scared. He was like, “Well, what do I do if I’m not executing every day?” He was self-sabotaging because he was unclear on what this hire meant for him, and why he was really making it in the first place. He was getting in the way of his stated desired outcome because he wasn’t inwardly clear about what happens next. He was just trying to fill the seat because he thought he was supposed to fill the seat.

One element of his eventual breakthrough was getting excited about what he would have energy and time for if he made the right hire. And part of it was about culture too — hiring is obviously the most direct way to build the culture you really want.

But most importantly, when he began to put hires in the context of achieving the mission of his company, and his mission as a human, he had a pretty dramatic mindset shift.

I want to add one other thing, though. Some of it is about faith, too. Faith forward. I bet you can find multiple examples in your life where you have said, “You know, I feel good directionally about where I’m going. I don’t know what the exact outcome is going to be, but I have a little bit of faith.” People who have kids do the same thing all the time, right?

I think having some faith forward is really useful, next to pursuing and relating back to why. And look, outcomes are real, outcomes are important. They’re important for a whole host of things. But we have to take a leap sometimes, too. I think a little faith forward is a key ingredient in generating the outcomes you want.

Josh:

Totally! I love that.

Prakash:

We’re not conditioned to these things so I don’t necessarily blame any of us. You, me or any of our clients or friends, it’s something we haven’t been conditioned to do but it takes some un-wiring. I know I’m still on the journey of it, as I imagine everyone else is.

Josh:

I’d love just for our audience to hear a little bit about the frontier of your practice, how your practice as a coach is evolving. Where are the borders or the barriers? Where are you thinking aloud from the edge? How is your work evolving right now?

Prakash:

I’m finding my practice is much more holistic now. The kinds of things that I’m working with people on is much more than “how do you lead your company.”

Because if you think about it, all of this is intertwined, including your nutrition, and your exercise, and your mental health. I think I was telling you the other day about how Johnson & Johnson did this thing at what they call the Human Performance Institute, where they would do things like take blood tests of executives, better understand their baseline, just like an athlete.

Josh:

I love it.

Prakash:

And ultimately helped that person be healthier in order to also help their performance. So I think my world is much more intertwined now. It’s no longer simply “how to you inspire a group of people?” or, “Hey, how do we reflect a mirror back on why you’re doing what you’re doing?”

I also find myself going back to the eulogy exercise. You write your eulogy. What do you want people to say? And then what are you doing now that serves that?

And, “where are our attachments getting in the way of our ability to lead ourselves and lead others?” Stoic philosophy is very trendy right now!

But in that way, I’m also spending a lot more time in what can seem abstract, or heady, especially looking at ancient texts, and I’m trying to make that much more tangible and practical in the everyday.

Josh:

I love the idea of getting blood work as part of leadership coaching — that’s provocative. Behind every obesity problem, for example, is a mental health problem. The medical word for that is comorbidity. Most of our challenges are multi-dimensional.

Behind a lot of leadership challenges are body mind connection challenges, and so forth. It’s kind of unnatural to have separated the two, and it’s exciting to think about you collaborating with a clinician or what it might actually look like to be coached in a holistic, integrated way.

And I do find that I talk with my coach about my body and my health far more often, certainly as we get older, but more than I ever expected. And obviously it’s all connected. No other coach I know is really thinking about it that way.

We’re actually right now designing a new curriculum for the emerging leaders at my firm. We’ve been talking to leaders and coaches and asking for their advice. Body, brain, health, and wellness keep coming up over and over. I predict that coaching is going to become more and more a clinical practice over time.

One last question for you. What is one message you would get out to leaders right now, if we could just put it in the water instantaneously?

Prakash:

I would go to awareness of self.

That includes why you’re doing something, and when you’re doing something that’s misaligned from your values, so awareness of self would be, “What do you truly value? What do you actually want and why?”

And: “Do you have the courage to actually go do it?” I think that awareness of those three things would be really powerful for everyone, if I could just snap my fingers and make it true.

Josh:

This was an awesome conversation. I really appreciate you.

Prakash:

I appreciate you, too!

Josh:

It’s quite jarring to zoom out and consider some of the questions that you’re talking about. I have not been very self-aware of late.

Prakash:

It’s hard!

Josh:

I have been in fight or flight mode. And in fight or flight mode, one of the things that goes right out the door is self-awareness.

Prakash:

But hey — this is crazy important — chipping away is not a bad thing. Chipping away is a good thing.

Josh:

I love that point, that chipping away is not a bad… I love that. Slow and steady.

Prakash:

Like, whatever happened to that?

Josh:

There’s a degree to which we want the shortcut, we want to overachieve — now! We want to get there early and chipping away is not sexy.

Prakash:

Yeah, it’s not sexy.

One thing I didn’t mention is that I’m finding in some of my work a worryingly prevalent attitude of like: “we are not willing to chip away.” Or: “Oh, instead of taking a two mile run today, let me take seven miles.”

Is that necessary? If you did two miles, 3 times, that’s better.

Josh:

That’s a great reframe.

Prakash:

Another important reframe is thinking about why we’re getting so polarized. I think it has a lot to do with the fact that folks are desperate to feel heard. So we’re kind of like, “What’s the most shocking thing I can say to feel heard?”

Josh:

I agree. The key success factor to reversing polarization is doing the best listening of your life. The best active listening ever.

You want to crush something, you over-achiever, you? Crush listening. You want to be an overachiever about something? You want to be outcomes driven? Be outcomes driven around being an insanely good, world-class listener. That’s what we need more of.

Prakash:

Totally. I love that.

Josh:

Of course, it’s hard as hell to actually listen to stuff you disagree with. But your reminder is the right one that I think, one that can help keep us all motivated to keep listening.

Folks want to be heard more than anything else. And what they’re saying can be read as an increasingly desperate attempt to get what they need.

We kept going by accident! I so appreciate you. I’m glad to have you in my life.

Prakash:

Thanks for having me, and let’s do it again soon.

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