198 - How Can AI Enhance Marketing Efforts and Human Interactions with Redwood Software's Andy Sharma
24 May 2024 · 30 min
In this episode of Listening with Leaders, host Doug Noll interviews Andy Sharma, CIO and CISO of Redwood Software. Sharma shares his personal journey from a second‑generation Indian IT background—initially reluctant to code—to becoming a technology conduit who bridges business and engineering. He discusses Redwood’s mission to automate repetitive work so people can focus on creative, high‑value activities. Sharma frames AI as an equalizer and force multiplier, illustrating how it can cut the time marketers spend crafting messages from 50‑60% to 5‑10% and how a technical mentee used ChatGPT to improve email tone, turning a communication weakness into a strength. The conversation delves into leadership philosophy: fostering psychological safety through emotional listening, encouraging a "10% time" culture for experimentation, and hiring for cultural fit rather than pure technical skill. Sharma describes himself as a lifelong learner and problem‑solver, emphasizing reflective thinking and subconscious idea generation. He also reveals his "introverted extrovert" personality, explaining how he balances outward engagement with needed alone time. Throughout, the dialogue highlights the synergy between AI, automation, and human‑centric leadership in modern enterprises.
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Welcome to Listening with Leaders. I'm Doug Noll, lawyer turned peacemaker. I teach executive leaders how to listen to emotions rather than words so that they can become the leaders everyone wants to follow. And I teach those same leaders how to be authentically present, available, and connected to their families despite being insanely busy. I have learned that we are 98% emotional and only 2% rational. Learning how to listen to emotions is, in my experience, the foundational skill of life. Stick around to the end of the show and I'll reveal how you can be on our next guest in 15 to 20 minutes. So let's get started.
Andy Sharma, welcome to Listening with Leaders. You are the Chief Information Officer and Chief Information Security Officer of Redwood Software, found at redwood.com. Welcome to the show.
Thank you for having me here, Doug.
We were just talking a moment ago about your background. You were born from Indian parents. Your mother was Sikh and your father was, I presume, Hindi. And you speak both languages, Punjabi and Hindi. And of course, you're now working in the United States.
What a story.
Tell us a little bit about it.
So Doug, I'm a second-generation IT guy. And even before I knew what I wanted to do in my life and my career, I was gently getting nudged towards technology. So, you know, everybody has this wildly successful uncle or aunt that everybody in the next generation is trying to emulate too, right? I had, I had a story. I have, I have an uncle like that who was the top guy for Citibank in India and brought up the first ATM and the SWIFT transactions. And everybody in my generation was being steered towards IT. Now, I was good at programming, but was it something I really wanted to do growing up? That wasn't my passion. And as a matter of fact, I tried to run away from it as much as I could.
Well, just on that note, I learned how to code in 1969.
Wow. Yep. So, so again, To me, just sitting and coding, trying to solve technical problems was not enough. I, I wanted to do more. I wanted to do more in terms of interacting with people. That was something that was of interest to me, and that's the reason why my perception that technology only means sitting in one corner and coding was something that was holding me back from basically going and embracing a career in technology. But as luck would have it, I did my internship in an IT organization for a company that was implementing an ERP solution in the mid-'90s. And this was the first time I had a 360-degree view of what technology does for the success of a business. And one of the other things I realized pretty quickly on was that there is a big difference between people who talk technology and people who talk business, and they don't understand each other.
Totally get it.
So, so what I really found was that, that I had that ability to be a conduit, to understand what the business leaders want and then convert that into a technology speak for the technical folks. And connect the dots. And I would say this is something which has been my USP. So as I said, I started my career in the mid-'90s implementing ERP solutions and got an opportunity to come here to the US, work for some, some really big organizations. Dell, I was there for about 13 years, worked at Charles Schwab, worked at Santander, one of the large banks in, in Europe. And, and since 2014, I have been taking roles of Chief Technology Officer, Chief Information Officer, and Chief Information Security Officers in software companies. And currently I am with Redwood. And as you know, Redwood is, is a, a premier company into enterprise automation. And we believe in unleashing the human potential. And, and that is what we focus on. We believe that anything that can be automated should be automated so that people are able to focus on more important things in life, on creative things in life, and having a good life.
Good for you. I am curious about your thoughts about the emergence of AI.
Wow.
So AI and automation, they are to me a marriage made in heaven. Because, because both of them have the same goal, as I stated before, to, to make sure that we individually and collectively are able to attain the maximum potential that we have. Now, there are a lot of people that see AI as a threat. I, I don't belong to that process. I don't see AI as a threat, but, but to me, AI is more an enabler. It's, it's more of an equalizer, a force multiplier. Okay, let me unpack that statement a little bit. So imagine you are a marketer. And you spend about 50 to 60% of your time building a perfect message. Right? And then you try to figure out what kind of response you are going to get on that particular message, testing it. And it takes a very long time for you to come up with that perfect message that can go out. Now imagine with AI, you are able to create that perfect message spending maybe 5 to 10% of your time rather than spending 50 to 60% of your time. How many more messages could you write, right? How many more target audience you can reach, right? And AI can do that for you, right? Right. I'll give you an example. I have, I have a very— a mentee who is super technical, and, and from a technology perspective, it is hardly anybody who, who doesn't love him, right, for his technical skills. But in his peer group, people complain about him having, like, looking for the right word, pointy elbows.
Gets a little assertive and aggressive, huh?
Right. So, so in that particular scenario, what happens is even with coaching, it takes time for somebody to, to, to pick up and, and really become conversant. So I offered this person one piece of advice: write your email and then ask ChatGPT to make it collaborative before you send it out, right? And, and, uh, 2 months after we had this initial conversation, the feedback was, was great, right? So, so, so that's why I believe, like, okay, for a technology person who may not be great at human, human interactions this AI is acting as an equalizer, right? Creating an environment that, that you have the ability to, to play on your strengths, but also your weaknesses are not that huge anymore.
So since we're on the topic of AI, I didn't really mean to get into this with you, but you're an expert.
You are—
one of the things that you were a specialist in is information security, and AI is going to complicate that problem, isn't it?
It's going to help us solve a lot of problems.
Okay.
Different people in the organization, different people, even my direct reports, um, there is a very different thing that makes them tick. Right. There are some people who say, hey, give me a goal and then check back in a month.
Right, right.
And, and I love those kind of leaders where it's with that have the ability to independently deal with ambiguity. As a matter of fact, I, I am good at my craft because I have a team, solid team that supports me. But at the very same time, there are people who are learning to be a leader in which they have to essentially figure out how to let it go and let somebody else do it. And, and again, that gives me a lot more satisfaction as, as a leader and as a human being to try and see, try to help people around to become better leaders than they were, to become better people they were a day before.
For you, I mean, that to me is the essence of leadership. It's, it's taking the people that report to you and the people that report to your reports and training them and bringing them up and saying, who's going to replace me?
Yep, yep. And it is not just replacing it, it allows me to grow as well. Of course, right? If you, if you say one person who has the ability to wear a CIO hat and then a CISO hat, it's impossible to do it by yourself.
Yeah, no, absolutely. So what is it about yourself you think that is, that's unique about you that has made you as successful as you are? Because you said earlier before we started recording that you had wheels on your feet, you've been all over the place, lots of experience. What is it that you think that has been unique about you that makes, that makes you 2 things, 2 things that come to mind.
Uh, number 1, I, I'm a lifelong learner. I, I want to learn something new, whether it is through interacting with people, whether it is, let us say, listening to a podcast, watching a YouTube video, something that, that I want to learn. I'm just inquisitive by nature. So there are a lot of times when I hear about a word for the first time, I do not know anything about it. Rest assured, before I go to sleep, I would have done some research on it, tried to figure out what it meant. And, and one of the things that I realize is more you go deeper into something, you try to, to to see that, that everybody has various different levels of understanding of the same thing. And more you dive in, more you learn. And I think that's one of the things that, that I'm fascinated with. Wow. The second thing that I would say is I'm a problem solver at heart. So it started with trying to solve technical problems when I was coding. And right now, most of the problems I try to solve are people problems or strategy problems, but, but again, those are problems nonetheless. And I think those are the two things that, that really make me excited to, to come to work and do my best.
So you're a lifelong learner coupled with a problem solver.
Yes.
What could be more perfect than that, right? Because it's the lifelong learning that allows you to solve the problems and see the problems that maybe other people don't see, or maybe see, see potential solutions that other people don't see.
And yes to both. And most of the times when I look at a problem, I'm not trying to solve it right away. And, and what I do is I, I let it simmer and let my subconscious mind come up with ideas. I sleep with a pen and a paper notebook by my side. And there have been times when I wake up like 2 AM with an idea that I just want to write down before I sleep.
So yeah, interesting. What do you do in situations where people are not giving you all the information that you need because they're afraid repercussions because the information isn't what you want to hear or what you're hoping to hear?
So, so one of the things that I do is create a safe environment for my team, and it is not what I say but what I do, because of which the team members feel empowered to, to come to me and, and talk about about things that are not working, what the way they are feeling. Now, now, I, I really make sure that people have the ability to come in and talk to me about how they feel. Feeling is not something that you can, you can articulate very well or have data for, but, but opening up or creating an environment where people have the ability to come and share how they feel is, is very empowering.
It is. In fact, that's exactly what I teach. I teach leaders how to listen to emotions rather than to words, because when you do that, you create the environment you're talking about— emotional safety. And you may be aware of this massive study that came out of Google a couple of years ago that— where Google was trying to articulate what— why it was the top one 10th of 1% teams spectacular and everybody else was sort of average? And the answer was because the leaders are creating emotional safety on the teams.
Yes. And I, I am thankful to people that, that allowed me. Um, so growing up, I was, I was always more like an entrepreneurial person. I would take ideas that to, to my leaders that probably a lot of people would not think about. And, and they allowed me the opportunity to try those out. A lot of them failed, Doug. A lot of them failed. But again, the more important piece was having that ability to go in and try things out for yourself.
So you, you were actually fortunate to grow up in environments— grow up professionally in environments where Your supervisors allowed you to experiment, try out new ideas, and they were okay with you failing as long as you learned something. It didn't cost the company too much money.
So usually I saved company a lot of money.
There you go. Uh, and, and so that's kind of the philosophy that you have now with the people that report to you.
Yes. And, and one of the things that I tend to do, Doug, is 10% time. Sharpening the axe. So it is like spend time learning about new things which are happening in the environment, things that you are interested in learning. And then what I, what I have done in the past is to come up with a list of, hey, there are a list of 15, 20 things that we would like to make some kind of headway in. These are things not on the roadmap. But if there are ideas, if we can come up with a quick proof of concept, things of that nature, here are the ideas for you to consider as a part of your sharpen your axe time. So people take advantage of that and I've been surprised. This was one time at one of my old jobs where one of the guys came up with an idea of, product adjacent to our cash cow that we had been doing for a very long time. And the idea was such, we spent like $40,000 or so and we sold almost, almost 50 of those to our existing customers as a tag-on to our primary product even before we went live. Even before the new product was available in the market. So again, I think there is, there is a lot that you can do if you channelize this, this urge for people to learn and to do something new.
Interesting. So the show's called Listening with Leaders. We've talked a little bit, bit about listening and emotional safety. How did you learn about the importance of listening?
So it, it has been something that I learned over a period of time, and, and it was looking at others that were successful, how they carried themselves and, and how they work things. I, I learned more by observing people than by reading books. And, and that has been the mechanism for me to learn how, how have the successful people that I look up to handle things. And, and I'm just trying to emulate what they do.
So you're— it's kind of like learning by osmosis, I guess.
Yes.
Um, you've encountered— I'm sure you've encountered people who don't listen very well. What's been your experience with those people?
I was one of them.
Really?
Yeah. So, so I think you have to change your mindset from how to respond to what somebody is saying to, to truly try to see things from their point of view or see more from their shoes.
That's exactly right. And it's something even more than that. Not only from, from seeing it from their point of view, but making them feel like they've been heard. Like they— I call it listening from the speaker's frame of reference. So the speaker feels deeply heard. That's the secret. And that's a skill that not many people have.
Yeah, and I'm learning.
Yep, most of the time people are listening on their own agenda, the listener's agenda. I'm here to gather information, make my arguments, you know, do whatever I do, but I'm not too interested in validating what you're saying. And the true deep listening occurs when you can validate the speaker so the speaker feels deeply heard. And that's when you can— then you can problem solve after that, because until people feel heard they don't want to engage in problem solving. Yeah, there's a huge power in that that I've learned about, and that's, that's what I essentially teach to leaders, is how to do that so that you can get to the gist of a problem in a tenth of the time that you would otherwise take to get there, because you're meeting this very, very basic and deep need to be heard. So what do you do today when you encounter people who are not listening so well?
So sometimes put them on the spot.
Sharp elbows, huh?
Sometimes it's necessary, right? You have to interrupt, which may, which may not be, which may not always be something that you want to do, but, but interrupting and/or Let us say asking them to paraphrase. If you understood, what did you hear? What did you understand? What do you think the problem is? And what I've seen is that you do it once, the next time the thought process on their side changes and it becomes a little more listening.
They learn from being instructed a little bit about how to listen and reflect.
Yeah, initially it's more about try to do it more subtle. But yeah, if, if it gets to a point that somebody is not, not listening at all, it's, it's one thing that I have found that works. Interesting.
So you work at the— it— you work at the sort of the convergence of information technology and leadership, C-level leadership, and people. And I'm thinking that working with people who are engineering types or more technical people traditionally and stereotypically don't have the strongest communication and people skills that we might like. Has that been your experience?
Yep.
Pretty dramatic. Yep.
Yep.
Tell us about that.
Absolutely. And again, one of the things that I realized, the technology people that, that are, that are not great at communicating, more often than not, are very much more sound technologically. So, so I do want to make sure that, that I listen to them. Give them the opportunity, ask clarifying questions to understand where they are coming from. And then more often than not, it's, it's like, it's just that they were not able to communicate what they wanted to say, not that they did not have the right material to talk through, right?
So I, I was talking to a colleague of mine who's a consultant in leadership consult big-time leadership consultant in New York City. And he was talking to me about how people, he runs into people from that are in technology, particularly people from, he said, people from India and people from Southeast Asia. And these people were just describing what we just, you were talking about at the beginning of the show. Their parents are telling them, get educated, go to the US, make a lot of money. Right. And they totally focus on whatever technical skills they think they have to develop in order to make themselves an employable commodity in North America. And they, and they, they are built into this attitude that grades are important, but learning how to communicate and learning how to relate to people is, it's like, it's like being on the moon. It has no relevance to their lives. I'm curious, is that the kind of thing that you run across?
So, no. And I would say, yeah, I would, I would say that I wasn't scared to come to the U.S. It was, it was just luck that that happened.
It's not so much about being scared as much as it is people don't place importance on the kinds of skills we're talking about. They put a huge amount of importance on their technical skills and no importance on their people skills. And I'm just wondering what your perspective is on that, especially young people when they're—
I think education in India is growing in a big way. Like, we look at Harvard and say there is a 2%, 3% acceptance rate. The acceptance rate in, in, in an IIT is like maybe 1 in 100,000.
Yeah, I understand it's very difficult to get into.
So, so bottom line is you have to be really, really, really good at what you do. And, and you have to have the right material to be able to get that.
Right. And the, and the people at India Institute of Technology are looking for more than just technical skills. They're looking for the well-rounded person.
Initially, they may not look for a Bin-Raudy person, but more from a, from a material perspective. But again, people who are, who are, who have the ability to be in, in that range also have the ability to adapt.
There you go. I had thought about that. That's really interesting.
Huh.
Well, that's great. And how do you, when you're, when you're hiring people, what are the kinds of things you're looking for other than their experience and technical expertise?
So I rarely talk to them about their technical expertise. I have my team that, that basically vets them out. What I am really looking for is how are they going to fit into the team.
There we go.
Are they, are they the right fit for the culture? Are they the right fit for the team? Are they bringing in something which, which the team will, will benefit from in terms of growth? There are a couple of assessments that I like team members that are coming in to go through. And, and then if there are any kind of gaps that the assessment show, I try to focus a little bit more on those and, and try to see, gauge whether they will be a good fit. And so again, I am, I am more looking for fitness than, than technical jobs. From my, from my team members, they basically focus more on technology.
Interesting. So they don't even get to you unless they've got the technical skills first, and then you're looking for, all right, how well these people are going to fit in and what can they contribute beyond their technical skills, what they, what can they contribute to team cohesion and team problem solving, things like that.
Yep. And one of the other things I do is before I make the final decision to hire somebody, definitely make sure that I am doing some reference checks.
Oh, okay.
Well, of course, obviously talk to people, talk to their past managers, and I try to talk to them by myself. That way, what happens is instead of relying on an HR person talking, right, I want to talk to them because I know what I want to— I'm going to be getting into. Exactly.
Sounds like a good process for you. One more question, Andy, and then I'll let you go. What's one thing about yourself that we would never know about unless you revealed it to us?
Um, okay, I am an introverted extrovert.
You're an introvert extrovert?
Yes. So when people meet me, I am easy to talk to, and I can be in a party and I can be alive at that party, but at the very same time, I, I go into into my cocoon when I'm in my thinking mode, and I want my own me time. So most people, when they meet with me, talk to me, they will not realize that I would, I would be one of the people that would want to have some kind of me time or just reflecting internally.
Absolutely. I understand that because that's the way I am too. And I will tell you that of the 200+ interviews I've done on this show, I would say that 90% of the leaders that I've interviewed fit the description that you just helped. They're okay out talking with people, but they really get their energy from inside, not from being around other people. And they would rather have their own quiet time than go out and be in a big party or go to a big concert or do stuff with other people because it sucks energy out of them. They can be out there and outgoing when they have to, and they're good at it, but the, but the real power comes from within. Yeah, that's, that is, I'm gonna, I'm gonna, I hate to always overgeneralize, but I would say that that, that describes 90% of the leaders that I've interviewed on the show. So interesting. Yeah, and it describes you and me too. Well, thank you so much for joining me. This has been a great conversation, Andy. I really appreciated getting to know you.
Yeah, same here, Doug. All right, it was, it was great talking to you.
Take care.
Doug Noll here. Thank you so much for listening to Listening with Leaders. If you are a successful executive leader who would like to be on this program, please visit podcast.dougnull.com podcast. If you got something out of this interview, would you please share this episode on social media? Just do a quick screenshot with your phone and text it to a friend or post it on the socials. If you know someone that would be a great guest, tag them on the social media to let them know about the show and include the hashtag #ListeningWithLeaders. I love seeing your posts and guest suggestions. We are regularly putting out new episodes and content content. To make sure you don't miss any episodes, go ahead and subscribe. Your thumbs up ratings and reviews go a long way to help promote the show and mean a lot to me and my team.
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