Inspired Execution

Chet Kapoor:

Welcome back to the Inspired Execution Podcast. Each episode shares the experience and learnings of a world-class leader on their journey to success. The guests on this podcast are bold, brilliant, and not afraid to change. As you navigate your own path, we hope you feel inspired by the stories, lessons learned, and the vision of the future.

Jennifer Smith is CEO and co-founder of Scribe. As a consultant early in her career, Jennifer saw tons of organizations struggle to unlock knowledge across teams. So she started Scribe, a productivity tool that helps turn any process into a step-by-step guide. Today we discuss her path from consulting to leadership and the simple question she waited too long to ask herself, "What do I want?", how context plays an important role in knowledge sharing, and her top tips for managing the most precious resource: time.

So you're co-founder and CEO of Scribe. I have always believed that leading a team starts with leading yourself, and then you coach a set of people and then you coach coaches, right? These are hard transitions. You go from leading yourself as an individual contributor, you start coaching people, then you start coaching coaches, and you've had great path that you've taken. So give us a little bit about your personal journey and how your leadership style has changed over time.

Jennifer Smith:

I love what you said about that transition because I think it's so right, and I think a lot of times people will hear managing yourself or coaching yourself, and they kind of feel like it's a throwaway. Well, of course I know how to do that, but actually it's a very real skill and one that unless you intentionally cultivate, it's pretty easy to kind of skip behind.

So my quick background, I was at McKinsey for seven years as a consultant. I did mostly organization and operations work, which functionally meant flying around the country for 250 days a year and trying to figure out how to make operation centers better. As part of that, I would sit behind someone who's staring at six to 10 screens, alt tabbing across them every day, trying to hit their metrics and frantically figuring out how to get their work done with some pretty challenging software systems. And this was 15 years ago, so I'm going to date myself a little bit.

They'd pull out these really thick binders and they would say, "Here are all of the processes I was told to memorize." That's not how I actually do it. I do this instead. I found these shortcuts, these better ways. And my job as a consultant was often just to write that down in PowerPoint and then distribute that back to my client. And at the time, I always thought, "Gosh, there has to be some better way." If this person could have just created that PowerPoint themselves, maybe they would've gotten the million dollars in consulting fees and had big impact on this ops center. And I sort of said, "Well, that feels like an obvious one. Certainly, someone will solve that someday."

And I kind of went on with my life and found myself in venture capital I was living in the valley at the time, and just found myself really drawn to the entrepreneurial journey and people who were interested in building, they just felt like my tribe of people. And I've always followed people. And so to me, venture was sort of like a step in that direction where I said, "Let me hang out where these smart people come through my office doors every day and see what I can learn from them." And as part of that, I got really interested in why people buy software. We talk a lot in the valley, obviously about how to sell it, but less so about what's the experience on the other side? Who are all these people who are deciding to swipe a credit card or pay a pretty hefty invoice. What are the problems they're trying to solve? And so I interviewed over 1200 CIOs, CTO, CDO type folks to try to understand just what are the challenges you're trying to solve with your business? Where are you seeing your biggest pain points? Where do you wish you saw software being invested to solve problems?

And I kept hearing this theme coming up over and over again, which people would use very different words to describe it, but it would be along the lines of, I've invested in my workforce. I have all these really talented people. I've bought all of these software systems and tools, maybe a varying quality, but they are what they are. And people show up every day and they're nine to five fingers on keyboard trying to create value working across these systems. And I have no way to really capture any of the knowledge of how they do any of that. That still lives in people's heads. It's institutional know-how, and it walks out the door every day at 5:00 PM and I got to hope it comes back. And so I looked at that and said, "Well, gosh, software can solve that." I mean, what if software could just watch people, experts do what they know how to do and automatically capture that knowledge, automatically create documentation? What if you made it like digital exhaust, just a byproduct of someone doing what they normally would do?

And so that was the whole nexus idea behind Scribe, which was, let's let people do the things they do best, the things they're experts at, the things they enjoy doing, and let's just use software to make it sort of automatic behind the scenes in capturing that and enabling them to share that with others and making others better like them and doing it in a way that doesn't take any of their time and doesn't take them out of the flow of work. And to your question about what that's meant for my quote, unquote leadership journey or whatever you would like to call it, I think for me it's fundamentally come down to asking myself a very simple question, which took me 15 years in my career. I'm embarrassed to admit before I really did, but it's a powerful one. What do you want? What's important to you? What kind of impact do you want to see in the world?

And to me, the process of founding Scribe was really looking at what was important to me and what I wanted my legacy to be at the end of my career. And to me that was to be part of building something and ideally something that endured beyond me where I could see my fingerprints on it and say, "Gosh, this had a real impact on the world.

Chet:

That is so cool. One of the things that I talk a lot about is because I think manage is very much a concept from the manufacturing world. The manager is sitting in the top, the workers are down there on the shop floor, and you–

Jennifer:

Almost as a dirty connotation and knowledge work, right?

Chet:

Yeah. And so one the things– 

Jennifer:

Who wants to be managed?

Chet:

Yeah, one of the things I talk about is coach don't manage, right? Is that something that... How do you feel about those words? And secondly, how does it show up in how you are building software for people where you're capturing knowledge? You want to capture the purity of what you're trying to do from a software point of view, not necessarily the hierarchy in it, right? Does that make sense?

Jennifer:

Yes. I mean, I think about that as really the democratization of knowledge. And I believe everyone is an expert in something. It doesn't matter what you're doing, where you sit in the quote, unquote hierarchy within a company. You are an expert of something and that thing is valuable, otherwise you wouldn't be there. And so to me, the shift of what we see with usage for Scribe and the kind of change that we see in the world is this idea of the best ideas, best practices can literally come from anywhere in anyone because everyone's an expert in something. And what if we made the best of what everyone knows how to do available to everybody else?

In terms of how I think about my role on the team, I think as CEO, I really have only three jobs, which is one, I've got to set an inspiring vision for the change we want to see in the world. Why is what we're doing, why does it matter? Why should we bother doing this? Why do we get up every day? I need to hire really great people and rally them around that mission. And to me that means almost getting out of the way. If you tell people what you're trying to solve for and you have really great talent, the rest almost kind of takes care of itself. And so to me, that's almost the opposite of managing. That's sort of inspiring. And then the third part is maybe more the coaching part, which is in my role, I need to obsessively listen to customers and be constantly sort of guiding and adjusting the how, how we get to delivering on our why and what people are doing along the way. And so I didn't use any of the words manage there. I don't think the team would ever describe me as a manager in that.

Chet:

I'm going to double click on this a little bit because I love the fact that we're talking about Scribe and talking about you. And so clearly in the way you talk about your leadership style, the three things you do as a CEO, you didn't use the word context, but you were like, "I'm going to set up this vision. I'm going to hire great people, and then I'm going to listen to customers. I'm going to tweak the path that we take." A large portion of that is context, right? And how do you actually deliver context to the team, even to your customers, but the way you manifest all of that is through your product. And so how does Scribe do that? How does it make it easy for teams to find and share knowledge and get this context where you said everybody does something important and make it available to others?

Jennifer:

Yeah. I think it's so important that this happens within the flow and context of doing work. When you hear knowledge sharing, what's the first thing you think about? You probably think about a wiki.

Chet:

A total of some sort, right? Old school bullshit, right?

Jennifer:

Its own separate thing. That's a destination where you're like, "Okay, I'm going to stop what I'm doing and I'm going to go do this knowledge thing." Whether because my boss asked me to write a knowledge  page or I'm really confused and I'm desperate and I'm going to go try to search out this knowledge page. There's a whole bunch of problems with having that be an activity that's separated from work.

One of the big consequences of which being very little of the actual process, knowledge, expertise that exists within a team or company is written down anywhere because it takes a lot of time. You almost have to have the goodness of your heart. So I'm going to sit down for 30 to 90 to 120 minutes, however long it takes to write this, and then I'm going to chuck it in this portal and I'm going to hope that someone looks at it someday. And then you never hear from anyone who's looked at it, there's no feedback loops, you forget about it, so it goes stale, maybe it becomes outdated. And then people know I'm never going to go look in that portal because the one time I did, I found something that was two years old and it was dusty and no one had touched it. As you get this kind of downward spiral.

And so I believe it can't be a separate activity. It needs to be tied to actually doing the work, and it can't take you out of the flow of doing that. There's a huge cost to taking a knowledge worker out of the flow of doing work. And so for us, it was all about software being in service of the way that people are already working today. And so on the knowledge sharing side, we said, "This has got to be so low friction and simple," and we've gotten it down to two button clicks. So it's a desktop application or a browser extension when you're about to do the process that you want to document because someone's asking you how to do it because you think someone in the future will ask you how to do it because you're about to onboard a new employee, or you found a better way and you want to spread the gospel. You just click the record button and then you do your process.

Here's how we generate our quarterly reports in our Salesforce. So you click record, you do the thing you normally would do anyways, and then when you're done, you got your second button click, you hit stop record, and boom, it'll automatically generate step-by-step guide with screenshots and written instructions on how to generate a quarterly report in Salesforce. And then the person on the other side who has to go generate that quarterly report, I mean, I think we can all relate to that feeling when you go to do that task and you don't know exactly how to do it. So you probably procrastinated a little bit. It feels just kind of disempowering, and you're sitting there and your choices are, okay, let me phone a friend and see who can show me how to do this. Let me see if maybe there's some documentation somewhere. Let me see if I can Google it or what most people probably do is let me just try to muddle through it and see if I can figure it out myself.

Well, now imagine when you went to that CRM, it just automatically popped up and said, "Hey, it looks like you're about to generate a quarterly report. Chad, who is your local Salesforce expert has actually created a guide on how to do this? Do you want to see it?" And you click yes. And on the screen in the moment in the place where you're going to do that work, it shows you how to do it and walks you through it.

Chet:

How does all this generative AI and predictive AI stuff actually affect what you are delivering as a product?

Jennifer:

Yeah, I mean, it's incredibly exciting what's happening. I don't know how you feel about it, but as a technologist building right now in this time, it sometimes feels to me like these just gifts are falling from the sky and we just all of a sudden have way better tools to be able to deliver on what we talked about. I'm creating an onboarding guide for new salespeople and I've got to pull in five different scribes or 15 different scribes, but all the things that person needs to do, and then I'm going to put some text around it to explain to them what they're doing here and put it in context. And you could do that within our product before we called that pages, but you had to do it yourself, right? I mean, you had to manually put that together. And that sort of just was a technological constraint at the time when we started and it isn't now.

And so now we've been able to bring that magic moment to we created all these scribes like, what do you want to do? I want to create an onboarding guide for new salespeople on how to use Salesforce. And boom, it'll automatically write all of that text for you and pull in all of this scribes that you've created on using Salesforce and order them within this document. And maybe you go in and you add your own flavor to it, obviously and whatever, but you're never starting from that blank screen. I get really excited about thinking how can we use generative eye to make it so that when you show up every day at work, you're spending as much of your time on the thing you love to do, the thing you're special and great at, the thing that gives you energy.

Chet:

I am going to take a little bit of a turn and talk about you. You talked earlier about the thing that we have to control is time and energy, and our attention is being hijacked by so many different things a day. Can you share a couple of time management tips that have helped you or you've seen other people where it's actually helped them with some great outcomes?

Jennifer:

Yeah. I love this question because I talk a lot about what me and others call collaboration overload. We have built all of these really amazing communication technologies that make it so any one of your colleagues or anyone anywhere in the world can pinging you with any kind of question at any moment, at any time, and you instantly get a notification around that. What we've seen a bunch of people have done real studies on this is we now end up spending pretty significant part of our day is collaborating with others. And collaborating feels like motherhood and apple pie, right? It's a warm, fuzzy, good word. Oh, yes, I collaborated today. I was very collaborative.

But what does that actually look like? That looks like you coming home that night and whoever you share your house with saying like, "Hey, how was your day?" And you saying, "Well, oh my gosh, it was so busy. I was so busy." Well, what did you actually spend your time doing? Oh, well, I was in a bunch of Zoom meetings. We had our Zoom meeting here, and then I was answering these Slacks and then I had these emails. And what you find is you're spending so much of your time collaborating, which is great if it's in purpose and service of something. And so a lot of the communications that you're getting that are coming inbound are actually someone else's agenda. They're trying to solve a problem for themselves.

And so I think one of the most powerful things you can do, and this comes to sort of managing yourself, and it can come with how you manage your day, how you manage your week, how you manage your energy, how you manage your talents. It's asking yourself, "What do you want? What are you trying to achieve? What's most important for you to get done today?" And you ask yourself that question first thing when you're getting started that morning, that week, and write it out. So I have my team write, you only do two things this week, what are those two things? And that's it. Let's laser focus on that because as soon as you open your inbox, do you know what all your emails are? Someone else's to-do list that they're sending to you. The Slack messages that are coming out, someone else's to do list that they're sending to you. In some ways, it's almost about being a little more selfish, doing the harder work.

I think our brains can learn to become uncomfortable with quiet and silence and absence of something to do. Do you know that feeling when maybe a meeting ends and you've got 15 minutes before your next meeting and you get these mild panic for a second, like, oh my gosh, how am I going to spend the next 15 minutes? And then an email comes in and then your brain says, "Oh, shoot. Okay, I'm going to spend my time responding to this email. I know what I'm going to do." That's your brain being in reactive mode. And where you want to be putting it towards is, "Hey, I've got to get these five things done today that are most important. Oh, gosh, I've got 15 minutes. That's great. I already know how I'm going to use this time. Let me block one of these things off." It may sound subtle.

So a radically different way of thinking about approaching time management and energy management and really managing and coaching yourself. It all starts with the fundamental question, "What do you want? What are you trying to do? Why are you doing this?"

Chet:

That's awesome. You've said people, they do impossible tasks every day, and if you want to badly enough, it's possible. So for our listeners, what are some tips and tricks on how you have inspired people or inspired teams to do the impossible?

Jennifer:

Yeah, I think this is actually one of the most important and maybe difficult parts of my job, and really being at a startup, because when you get started, the odds are completely stacked against you and there's no reason that you should be successful in the thing that you're doing, right? And yet you see incredible companies get built all the time. And so what you have to do is inspire a team and make sure you first are hiring a team who have the capacity to hold this belief and then continue to reinforce it that that is possible and not just it's possible, that it will happen, and that you can simultaneously believe it will happen without knowing the how along the way yet and believing that you'll figure it out.

And so we've kind of formalized this at Scribe and one of our core company values is no limiting beliefs. It's literally no limiting beliefs. The way that we reinforce that is we constantly call it out every time that it's role modeled. And when you're in a hypergrowth environment, I think it's very easy, fortunately for us to be able to look at it and say, "Hey, guys, remember six months ago when we thought that it would be crazy to be adding 100,000 users a month? Well, guess what we just did?" And you keep role modeling that in small ways and in big ways, and it kind of starts to break down this mental model of like, "Oh, gosh, well, yeah, maybe I thought something was not possible before, but we just did it. Or I just saw someone else do it. And so, gosh, why would I think that we can't do that again?" And I can hold that belief without having to know exactly how we get there. And that's kind of a hard tension to hold as a human, to believe something is possible without seeing the path yet for how to get there. But that's exactly what you need to do and what you need to inspire people to do.

Chet:

That's awesome. Know that it's possible but don't know how to get there. And keeping those two beliefs, I mean, strongly, and then just taking one step in front of the other will get you there. Is that fair?

Jennifer:

Yeah, I mean, that's exactly right. I think you have to believe it's possible and believe that you'll figure it out and that the right things will come at the right time and then be willing to put your head down and do the real work.

Chet:

All right, we're going to move to the rapid fire section of the podcast. One thing you cannot go out of your house without?

Jennifer:

I'm going to be cheeky and say shoes. And the reason I say that is I think most people by default would say their cell phone or something like that. And I'm purposely not saying that because I will usually leave the house and go for a walk without it. And for me, it's a way to kind of disconnect. Usually, I'll bring my son with me, so you might say my son in that case.

Chet:

Favorite productivity tool besides Scribe?

Jennifer:

Most people probably wouldn't call this a productivity tool, but the thing I use the most is Siri. Despite complaints I might have about his varying level of quality, I can speak much faster than I can type. And so most of the messages that I send are voice dictated. To me, that's just a big time savings.

Chet:

If you could time travel, which historical period would you visit?

Jennifer:

I lived through it, but I would love to see it with my lens now, which was the period of the birth of the internet, because I think what's happening with generative AI has a lot of parallels and is at the same kind of level of impact on humanity. And I remember the first time I Googled something, I think I was in middle school, maybe high school, early high school around the time, and it just being the coolest feeling in the world, and I would love to revisit that now as an adult and a technologist and someone building software and kind of compare how much of that was me viewing it through 13 year old eyes versus now understanding what that actually means today.

Chet:

I was there, and I will tell you this is going to be far bigger and far faster. It's 5x bigger and 5x faster.

Jennifer:

Definitely going to be a lot faster. I think it's bigger too. The only reason I don't say it's bigger is it was a prerequisite for this, right?

Chet:

For sure.

Jennifer:

Like the invention of electricity. And we had to do those to get here. But in terms of how quickly it changes, the way that people work, definitely faster.

Chet:

You're a founder, CEO and a mother, what's one thing you've learned from your son?

Jennifer:

The thing that I continue to be most amazed by with my son is his just pure joy and zest for life in everything. He thinks everything is amazing and awesome, even things that we would find to be nuisances. So you and I were chatting before this, they're chopping down a tree in the backyard right now, and it's making a bunch of noise and branches are falling all over the place. And I'm like, "Oh, what a nuisance." He is laughing hysterically. I don't know why he thinks it's funny that branches are falling from the sky with really loud thuds, but he thinks it's amazing and he's delighting at it and finding joy in it.

And so I'll often ask myself, "That's the core basis of what it means to be human. Our purest sort of sense is to be in joy and wonder at the world, and are we just layering on all of these obligations, worries, cynicism, sarcasm on top of it?" And if so, that's a false adult invention. That's not the way that we are wired. And so I find myself trying to incorporate more of that wonder and gratitude that I've learned from him. And one of the things that I do with him is every night before we go to bed, we kind of do a gratitude practice. He's 18 months so it's one-sided, but I'll talk about the things we did that day and what we're thankful for. I'd like to think that he's kind of smiling and nodding as I'm going along and someday help participate in it.

Chet:

The unconditioned mind, which is great. What advice would you give your younger self?

Jennifer:

Ask yourself sooner what the heck you want. It sounds simple. It sounds crazy. I mean, I've had the privilege to study at and work at some pretty exceptional institutions, and I would say most of those places, that's not what people are, or at least at the time I was there, were doing, they were asking themselves, "What should I be doing? What would be prestigious? What do people like me tend to do? What does the path look like?" They're worried about the how, how do I get to where I want to go? Well, how do I get to where I have set for myself as a goal? And they're not asking themselves, "Is that what I intrinsically want?"

And I think so much value comes from really understanding yourself and what makes you tick and what motivates you, and then aligning the way that you spend your time and energy against that. And it's not just because you're going to have a way better experience along the way. I mean, it's a difference between pushing a boulder uphill and doing it in the hot baking sun painfully while you're being tortured or following a boulder that's flowing down the hill in this wonderful green countryside. It is a completely different experience. It also means you're going to be way better at it. You're just going to be more successful at something that you enjoy doing versus something you don't enjoy doing.

And so one of the biggest force multipliers you can have on your life is asking yourself, "What do I like doing? What do I want to get good at?" Okay, let me dedicate my rare talent, energy, and time towards getting good at that thing. And then let me trust that if I love it and I become excellent world-class at it, great things will come because I don't care what you choose to do. If you become world-class at something, you will be very successful. It doesn't matter what it is.

Chet:

No doubt. So the essence is what do you want?

Jennifer:

What do you want?

Chet:

Clear on what you want.

Jennifer:

What are you willing to commit to becoming world-class at.