Originally aired on February 5, 2021 @ 1:00 PM - 1:30 PM EDT
Cloudflare President of Field Operations, Chris Merritt, interviews Tech luminary and entrepreneur Rajiv Pant. Rajiv runs his own management practice focused on Product, Design, and Engineering. He was also a former CTO at the New York Times and CTO and CPO for The Wall Street Journal.
Don't miss Rajiv's blog, including his piece on 5 Productivity Tips for Executives in Leadership & Management Roles .
Hey, well, welcome Rajiv. Thank you for so much for taking the time to hang out with us today in Cloudflare TV It's been a while since we've seen each other in person. We were just catching up. It's great to see you Where are you right now? Great to see you. I'm here in Manhattan in New York City And you've been there the entire pandemic or? Yes, during the entire pandemic. I'm looking at snow outside here And I can literally open my door and grab some snow and make a snowball Although I don't have anyone nearby to throw it to Well, if you can do sort of a virtual, I guess it's this way you can throw it across the screen at me Just by way of background, I'll introduce you to the crew and the audience today So Rajiv, I've known you for almost a decade now Rajiv is a luminary, a real tech product design engineering leaders Well known in the digital media technology space From being a young global leader in the World Economic Forum Lots of accolades and recognition You've been in the media industry for a long time Starting off with Knight Ridder through Cox, Conde Nast, including Reddit New York Times Tribune You spent time with Ariane Hoppington on a Thrive property You worked at the Wall Street Journal for a number of years in the Dow Jones companies And more recently have gone and done advisory work Including with some of the largest, most well -respected advisory firms in the world Thank you for being here My pleasure, thank you I miss seeing you around the circuit Rajiv is on the circuit frequently And I'm sure you're on the Zoom circuit now, but it's not the same thing Yeah, no, it's not the same thing Oh, and one more thing I'm also a technical co-founder of Happio, a Silicon Valley startup That's aiming to change the way we work using behavioral science and machine learning I won't go too much into what we are doing But I can speak to the technologies besides those two And obviously we are going to be using Cloudflare in our products So that goes without saying Well, thank you for that plug And I don't want to It'd be great to have you sort of weave in what you're doing at Happio And if I step back, though, and start off with your career You have seen so much both sort of deep technical stack evolution But also the industry itself As you explain your career How do you talk about the arc and the different points along? Just maybe give a little bit of context for how you see it You know, so I would say certainly speaking of the arc And some things, you know, go one way and like a pendulum Then they swing back So, for example, you know, take a recent example on the technologies When the web began, it was all about static pages And then we moved to, you know, dynamic pages Meaning dynamic on the server side You added a database People created extremely complex things like EJVs That you needed a whole team of people to understand and run And then that led towards simplification of the stack And then more recently with things like Jamstack And, you know, client-side dynamic But server-side static becoming more popular And then using APIs, microservices to build out applications And particularly, you know, seeing products like Cloudflare pages Launch and go that direction So it's interesting how that on a technical end Some things have made a comeback Although it's not a comeback of the exact old thing But it's a better version of how the web began And you see this kind of a change also in organizations In the way they're organized If you look at, say, a big conglomerate They may be highly decentralized for a while And then they find that by being decentralized There is a lot of innovation in the company People feel a much closer connection to the products And to their customers But over time, you will find that there is a duplication of effort Costs pile up And then a company tends to centralize And then a company becomes highly centralized And they save a lot of money and costs go down But then the innovation goes down And revenues will suffer sometimes as a result So you see these companies also go in this pendulum fashion And I have seen both on the technology and on the management side These kind of changes happen over time And what I find particularly interesting And what I'm most passionate about Is how technology and management as a science come together And that's part of what we are also focused on With the Happier product But what happens is I'll give you some basic examples of how A lot of my friends, myself included When we first went from being a software engineer to a manager We didn't know exactly how to be a manager Sure, you learn about it in school You read all these books But there are basics There are things that people do Like, for example, if somebody is a lead software engineer And they get promoted to the role of a team manager Of a group of technical people And let's say their boss got promoted Or went to another job Now this person says, hey, what did my boss do before? Okay, she used to have a meeting of all of her direct reports Once a week And she would have That would go on for an hour And this is the format This is how she ran the meeting And then she used to have a one-on-one With each person in her team And talk to us about, you know First 10 minutes or so about personal stuff And make sure we are happy about our career And do these meetings So then they copy this behavior But they have never actually studied Whether that was effective Or why she did it What was her reasoning And if she made changes to that process For what reason they made the changes They just know that that's what my manager did And that's the behavior I'm going to copy And this goes in a lot of aspects Of becoming a manager or becoming a technologist And I've seen this People have, you know I've written a blog off and on And I've been working on my book Culture, Technology, Operations, CTO And the theme there is So a lot of times people will read my blog About technology and say Hey, I just got promoted to a CTO job I found your post very helpful I have a 90-day plan on my site For a CTO in a new job As well as various other things about You know, how to do this And what I find fascinating is that Even when engineers become managers They will often not approach management as a science They think it's this fuzzy thing That all touchy-feely, sensitive people do But there's also a science to management And one has to understand behavioral science Understand human psychology, social psychology And I think the more you apply that to your work The more effective one can be as a manager And for people in the technology field I think people in the business field Folks like yourself, management comes naturally Because in your field You're leading people You can just do that intuitively And you've also learned that throughout your career But if you're somebody like me Whose passion was to write code Or to build products or to design things And now suddenly you have to work with these people And the first thing you realize is that Every human being doesn't have the same API You have to interact with them in different ways And you also realize it's not like you can just Turn it off and turn it back on again So there are many of these things That fascinate me about management And that is the thing that I've been most passionate about in my career How can one be a more effective manager By understanding the science of it? First of all, you give me too much credit I've been taking notes here I'm like, wait a second I shouldn't just be pattern matching Against one-on -ones and staff meetings My staff is cringing Why are we doing this, Chris? They're going to ask me the hard questions And I'm going to say call Rajiv Let's go back to this for a second So if you unpack You are going through your career You are pattern matching And you're decomposing the problem along the way If you were to go back and give advice To your earlier self I want it to feel a little uncomfortable right now What were those things where you're like Oh, I did that so wrong And I wish that I had done this differently What are those moments that send the hairs on your neck up a little bit Or maybe make you sweat? You know, so, yes Some things, certainly I learned in my career Is that There is no easy substitute for experience It doesn't have to be your own experience But it can be the experience of others I've learned some lessons this way in my career One of them being back in the day When there was this job called a webmaster And you did everything from Running the systems The hardware There was no cloud back then, of course So we had installed these RAID drives And of course the theory was that In a RAID system You could pull out a drive from a live system While it's in production And things would all work Chaos Monkey wouldn't break it Yes, and Chaos Monkey wouldn't break it But of course We did pull out a drive like that And now in hindsight And of course, it crashed The entire system crashed It was a mess And the lesson I learned in that Was that, hey, even if you read something All the books, the blogs, everything says this is okay But there is a wisdom Had I been more mature at that point I would have thought, okay, yes Everything says it's okay, but I should be prepared for Murphy's Law So that's one thing The other thing A lesson that got reinforced to me Throughout my career was this That there are a lot of people who are not Programmers or technical people But they have really good ways of finding solutions To technical problems I remember one day, early on in my career When I worked at Nitrader and the Philadelphia Inquirer A colleague of mine and I Were pair programming together Building one of the earliest content management systems Around And we were struggling with this one particular technical problem And we were I think we had spent like six hours On this problem and we kept trying to figure it out And we were both very proud of ourselves As software engineers We thought, oh, we are these amazing great software engineers And that's what we thought And after a while One of the folks in our team who was a project manager And was a journalist Had a journalism background, had never really programmed or anything Came up behind us And asked, you know, you two seem very frustrated What's going on And of course my first reaction was to say Hey, you know, this technical, complicated software engineering stuff You wouldn't know it But I didn't say that And I turned around and perhaps You know, just out of frustration I explained to him in English What the problem in the Java programming language Was that we were facing And without even blinking In English, he gives us a solution for the problem And it worked And I was just blown away I was thinking, wait, he's not even a programmer Not a technical person And that showed me How when you translate Something technical And present it to somebody who's non-technical A, that's a very useful thing in your career And B, when you do that You will find innovations And solutions from people That you would have never got them from otherwise You would have never even thought to ask them So I made that a key part of my job From there on When I worked with journalists in the newsroom Whether it was my job at the New York Times At the Wall Street Journal Working in any of these jobs I would go talk about what I'm working on Whether it was Even if it was deeply technical With other people And not only did it interest them a lot In building these solutions I also got solutions to things from them Because they had a completely fresh perspective On these things So that was one lesson Another key lesson I learned in this Was to deeply involve the customer Or your client in building a product And that's something, of course, over time As agile development These things became more popular Has become more mainstream now But I found that When people are part of building a product They are far more engaged And invested in its success I remember two examples One is this story This was the early days of the web In the 90s We had built a publishing system for our newspapers And there was some issue And our CMS was crashing and having problems This is the forefront These are early days on the web Don't downplay this The media industry was at the leading edge Yes, it was very exciting We were building these sites then So one of my colleagues An editor from the newsroom Came up and was sitting with us While we were trying to solve this problem And we spent several hours Finally got everything back up And it was working And I was very down at that time I thought he must be so disappointed That our technical systems have crashed And so on Because that didn't happen in the printing press You always had the newspaper out But on the web there were these outages But to my surprise A few days later I found that when he was interviewed By a trade publication He talked about how great this system was And I was puzzled I thought, wait, he witnessed all these problems And why did he say that this was so great That he loved the system And all the capabilities it gave the newspaper And then I realized It was because it wasn't the tech team's problem He helped solve it He sat with us While we were troubleshooting the system And building it And taking care of these things So he completely understood And that was something I found Very helpful later on too And sometimes When we are hard on ourselves as engineers The more we have involved Whether we call it the business side The journalism side Or the other colleagues in the company It's one team Some companies have had a motto That no problem is somebody else's problem And the more you embrace that in a company It has mind-boggling effects I remember at one time I was on a vacation In Hawaii without much access to a phone And there was a message In my hotel room On the answering machine The blinking light Yeah, and it was from our CEO And I thought, oh my god I am fired Clearly there is something wrong Otherwise you don't get a call from your CEO During the vacation I think due to the time zone I couldn't call him back right then And I was thinking About all the problems That we had had over the last month Stressing about them And trying to say, oh my god, what is happening And then of course I call him And he says, hey, you and your team Have been nominated for the Knightrader Excellence Award For technology, for the same system It was for the same system That I thought had had all these problems And then again I found That the common theme was Because when we worked on the system The good and the bad We shared it with everybody else in the company And we were very transparent About how it was built, how it was developed And what the challenges And other things were So people appreciated it We didn't try to spin it in a positive light Or sell it for anything more than it was So these things Taught me the value of Not thinking that technology Is some other department It's a core part of the business And over time as I've Been in various CTO roles at companies I've focused on integrating At the very least, product design and engineering I often use this term I coin PDE to refer to Product design and engineering One unit, but not only that being One unit, but that being deeply integrated With the rest of the business And the more you do that, I would say The more successful a company is And speaking of these Outages and things we deal with I remember Cloudflare was a big Big help to us when I used to work at The New York Times Well I was going to bring that up Are you okay talking about that? Yes You're like the definition of collaboration Like co-labor, working together So much of what you've been talking about is How you work well with your teams With your peers and the functionals Across The New York Times I think the story you're referring to Is where we started working together And maybe just So what was the backdrop? Yes Our systems had been Attacked by a foreign adversary Who had caused havoc on our site By taking over certain DNS And other services That weren't even physically in our building Or in our direct control And just as a Connection to that I have been personally A paying customer of Cloudflare Since its early days for my personal blog and site Because I always felt as a CTO I need to have a robust solution Even for my personal stuff So in that process I had Gotten to know Matthew and Michelle And the Cloudflare team And we were not a customer Of Cloudflare at that time And we were sustaining This significant attack It was a bad day It was really complicated And I reached out to Matthew Saying hey can you help And it was incredible how he got So many people on the phone call Not only Cloudflare executives Cloudflare engineers, Cloudflare folks Working on the product But he pretty much called the who's who Of the cybersecurity industry in Silicon Valley for us And helped us Solve the problem, get rid of it And bring our systems Back to normal Get past all this hacking stuff And didn't charge us a penny We weren't a customer, didn't say anything But it was just to help out And I thought that Wow this is a really great company They helped us out because they care They cared about the New York Times They cared about us There was no thing that hey if we help you with this problem You have to sign up as a customer or you have to pay a fee There was nothing like that It was a complete willingness to go above and beyond To help us And that is one thing I've seen from your company Both when I In my jobs I've been a customer of Cloudflare And at times when I've not been a customer Of Cloudflare You folks have always been around to help And there are certain things when it comes to Scalability and security Where there are few companies in the world Who can do this Who have the technical ability And who have the industry connections to be able to solve Because a lot of times solving Complex technical problems Is both about technology But also being able to tap into A collective network of experts in multiple Different industries Whether it's legal, whether it's law enforcement All these things come into play when you're dealing with Cyber security things And I'm very thankful I blogged about it back then and I'm very thankful To all the people from Cloudflare As well as other Silicon Valley companies Who are friends of Cloudflare Stayed on the conference call to help us out That was an amazing experience That's really a testament To you as well You are somebody that in the industry People want to be helpful to And you're being humble as well I think you've helped a lot of other people We were talking on the side Just as a little bit of an aside We were talking about what right before we started this You've been spending time helping Others during the pandemic Which I'm a little bit ashamed To think I have not been doing enough Can you just say a little bit about what you've been doing To get outside the building And get some box weights That is interesting Outside of the technology work Technology management consulting work And the startup work I also decided during the pandemic To do some volunteering for New York Cares And frankly I had never done Physical manual labor like this before And part of the work Involves delivering food to elderly Disadvantaged New Yorkers Who are in their buildings and can't get out So I'm carrying these loads of food And some of it involves Early in the morning In the very cold weather Packing the food and giving it to people Who are waiting in a line outside And I would go start this work And I was first fascinated That I have to do all this manually And I would think as a technologist And as a process person I would think I could make this efficient this way And this way I could set up an algorithm To train itself On how these systems are running And do it more efficiently And I would think about Instead of pushing all these carts manually We could have a robot And then I snap out of it and tell myself Just shut up and keep pushing You are the robot It gave me a deep appreciation For these people Whose job it is Because there are many of us technologists And business people who go do this volunteering But we do it When we have the time available At our convenience There are other people who do this for a living And they work so hard So I learned A tremendous amount of respect For these people And how they have been resilient Because a lot of these food services and other things Were not designed to handle a pandemic In the past The people, the homeless folks who were coming there Could enter the building and take the food from there But now that cannot happen So all the food has to be outside And just understanding The entire supply chain process And all these things And of course my part in volunteering Is simply to lift weights and put things and move food around But I can't stop thinking About how you could Apply a lot of the things that we have used In the industry To help this kind of work Well you're Yeah It's not even the last mile It's the last three or five flights of stairs It's that problem Yes And The human touch aspect also matters I've seen As a CTO I took great pride In when I would come into the office Walk by a lot of the folks in the team Whether they are an engineer or an intern or anybody And ask them how they're doing Talk to them about their work And greet them And I found that also applies when you're doing this When I'm outside I felt it is not just part of my job To give them the food delivery But also ask them how they're doing Especially in these days when people Haven't had anybody to speak to Other than maybe when they come to pick up their food It's a very rewarding feeling And it's a It's a very different way of working Than being in a corporate management Other kind of job You're getting the It's not just this muscle you're flexing But it's also the heart And the muscles That I saw right behind you I could see the weights that I know That you've been religious about over the Pandemic So it's great to see you be able to do that Yeah, I have made that a habit as well For the last 11 months or so I've made it a principle To be able to work out every day in the morning And I even blogged about it And I've certainly Come to experience that if you do that Every day, it makes you more productive in your work Helps you with your focus, you sleep better And during a pandemic Where our social interactions are limited It is really good for the mind So I highly recommend Anyone who can and is able to work out As often as they can I was not expecting to get Such a ringing endorsement And healthy Both emotionally and physically Getting that The regimen improved But I'm taking notes It's great to see that We have a few minutes left And you have a really privileged position You have in your career that we talked about But you also, through the advisory work And the circles that you run in And I don't want to downplay this I actually want to give you credit If there's an interesting group of people Meeting to talk about hard subjects And hard problems Rajiv is very often involved in that When we were at Davos We were over in the corner Talking to Tim Berners-Lee About some of the problems on the web That just was happening in the corner So you have a very privileged lens And if you think about the things That are stimulating for you That are the hard problems Just pop your head open And maybe say a little bit about What the hard problems are That you think are interesting and worth solving right now So one thing I would certainly stress is The pandemic has revealed a lot about us As individuals As a society And there are of course Experts working on solving the problems During the pandemic Of the medical science And people being able to work remotely So those of course are very important And hard problems But I won't dwell on those Because there are already some of the world's best brains Working on that What I find is a hard problem And my favorite kind of hard problems To solve are the problems That apply both Human cognitive science And machine learning to solve problems And in that space I would say How do you implement public policy Or policy within organizations And other places To change human behavior To be more effective And more resilient In dealing with things like a pandemic We have challenges these days Where a number of people are unwilling to take vaccines A number of people Are unwilling to put on masks And what happens is There are a lot of people The people who by the way Are defiant about all this Would perceive them as elites Whose message they don't want to accept And what is the most effective way If somebody is refusing to Wear a mask Or somebody is refusing to Get a vaccine How do you actually change their behavior And I once tweeted about this I had an experience I was taking a train during the pandemic And there was a person who would not put on their mask In the train And they were in the same compartment as I was And I felt compelled to go speak to this person about it And I said Would you mind putting on your mask I wasn't rude, I was very polite And the first reaction was Hey go away And I decided instead of going away Just engage the person in a conversation Of course I was wearing a mask And I was careful enough But as we had a conversation I understood his perspective Instead of arguing with him Listen to him with an open mind And at the end of the conversation He not only put on his mask We had a really great conversation And this was several months ago And when we exited the train He gave me a piece of advice He said when you go back up on the street Try taking off your mask for a while And enjoy the weather And I said thank you, I will do that And it's about understanding the other person This is on an individual level And you can do this at an individual level But how do you apply technology To help people To change their minds About topics where You do think it is good for them And you are convinced There is overwhelming evidence that it is good for society And how can you apply behavioral science Amplified by technology To change human behavior So that the next pandemic Spreads less So that people are more careful Because most of the time It's system one in our brains that is taking over and running So how can Technology assist When system two shuts down in our brains And we are just following our instincts Well as you described earlier The APIs that we all And the set of rules And the parameters required They are inconsistent at best Between people And I know we only have a little bit more Than a minute left You You get to see These interesting problems You have the time and the head space To put your mind around What might be solved around that You write about things What's the best way to follow you And to track along And try to draft behind the interesting Work that you are doing Is that through your blog or where is that You know my blog Rajiv.com I was fortunate to be able to register that domain Long before domain names Were such a big thing So I have my blog And I occasionally tweet So those are certainly good ways And if anyone needs to get in touch My blog is a great way to reach me Well there's also I don't know if you still have it up Do you still have the one on personal productivity habits Sort of the easiest way That's like a seminal Rajiv post And we'll find a way to link to it In the show notes somehow That was one of the first things I actually read about you Rajiv it's always a pleasure to see you I can't wait to see you in person After the pandemic is done It's great to see you're keeping up with You know your health Mental, physical and also doing good In the world Thank you for spending time with us And thanks for being a part of the community I'll bid you a good rest of your day Thank you, you too Bye