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December 9, 2019 · 16 min read

Interview with Shauni Deshmukh, CTO at Tettra

In this episode, Shauni Deshmukh, CTO at Tettra, joins the pod to share her insights on transparency, building your team, and her knowledge gained throughout her career working in both the software engineering seat and CTO seat.

Shauni Deshmukh

CTO at Tettra

Shauni Deshmukh is CTO at Tettra, a wiki for growing companies. Shauni believes that a culture of learning and transparency, enabled by documentation, helps teams scale efficiently and deliver excellent products and services. She’s passionate about building thoughtful and inclusive engineering teams. Prior to Tettra, Shauni held engineering roles at companies of all shapes and sizes, including Twitter and the U.S. Digital Service, a technology team within the White House. 

Read transcript

Ledge: Hi, Shauni. Good to have you on.

Shauni: Great to have you! Great to be here.

Ledge: It is great to have me. I often tell people the same thing.

If you don’t mind, would you just give maybe a two or three minute introduction of yourself and your work, how you got here and what you’re doing?

Shauni: Sure. I’m CTO at Tettra. We build a knowledge management system for high performance teams. We integrate with all the tools that you’re already using, like GitHub and Slack and Google Drive. We try to be the hub for where you store all the knowledge.

Before Tettra, I was at U.S. Digital Service, which is a tech team inside The White House that consults on critical government infrastructure and projects. It’s often called ‘Peace Corps for Nerds’. It was born out of the crisis, and I did a little bit of everything there – from consulting on website monitoring and metrics to coaching on how to do agile development. It was a really interesting experience.

Before USDS I was at Twitter, and I think that’s where I learned what software engineering at scale looks like. I’ve been at organizations of all shapes and sizes – from the tiny startup that I’m at now at Tettra, to everything from the federal government – and I really think that transparency is relevant no matter what kind of company you’re at.

The mechanics will be different whether you’re a five-person company or 5,000-person company but the principles are the same . I think it really enables a team to work on the right things and work much faster.

What I love about the role that I have now is that I get to do a little bit of everything. I spend time pretty hands-on in code, solving engineering problems, but I also get to think about how to build a thoughtful culture that’s inclusive, and I think transparency plays into that as well.

Ledge: Absolutely. There’s a lot of places to go with transparency.

You talked about the principles, I guess, of transparency. I wonder, if I asked 50 people if they would all come up with the same principles.

What are yours, and what are the ones that have anchored you and been successful when you think about transparency in an organization?

Shauni: Sure. To me, I think transparency is about two things. It’s about accountability and it’s about trust.

The accountability side of it is, are the leaders working on the right things? Are they making the right decisions? When the entire company has access to almost all of the same data, it’s much easier to justify why you’re making certain decisions and you’re not just making them off of I’m the boss and that’s why I’m doing it.

That kind of behavior also builds trust among your team because they see that you’re doing things for the right reasons, and they are more likely to want to also help in achieving those goals.

Ledge: Have you experienced cultures on both sides of that? It sounds like maybe transparency would not be transparency unless you’ve experienced the opposite. Where you didn’t have it and you wondered about, hey, why is the ship going this way? Now you have a chance to be a leader and build something else.

I’ve found in my career, and I talk to a lot of people that say, hey, I took notes along the way and it generally turns out that the list of things you’re going to do is shorter than the list of things that you’re not going to do. Right?

What’s the story back there?

Shauni: Yeah. I think this is most apparent in larger organizations and in the government. I think that what often happens – and this is not just in government, in lots of teams – is that there’s sort of a fear around exposing too much information, because by being open you become vulnerable.

This comes into play in all sorts of situations. One is job security. If only one person knows how to handle a certain system, how it works, and there’s no documentation around it, there’s a lot of fear around what happens if that person leaves, or we can’t fire that person.

There’s decisions around how you build your teams. It shouldn’t come down to fear. It should be you love working with those people and they’re good at their job, not because they’re the only ones in the world who know how to do something.

On the other side, I think a lot of people shy away from transparency because it’s the job of management in a lot of companies to curate and distil what relevant information is for their team. I think the reason they do that is because having too much information can be a distraction. I hear that a lot from other companies, especially around things like salary transparency. Worrying about things that are not immediately relevant to the job at hand can make you lose focus.

I think what we try to do at Tettra is, instead of dictating what information we should have access to, we try to create information as self-serve. The way we keep everyone aligned and focused on the right things it to keep hammering on, these are our goals, let’s stay aligned on this is what we’re trying to achieve. It’s up to each individual teammate to figure out, okay, is this data or information that I’m seeing actionable? Is this relevant? Do I need to engage with it? Or can I just let it go for now?

Ledge: Absolutely. It makes me think that you guys have this cool meta experience of being like, let’s all get together and figure out what transparency is or isn’t or ought to be or ought not to be, and then build a product around it.

How do you think that you’ve taken the next step in that? We talked a little bit off-mike going way back to the first beta PHP wiki that I could get off GitHub way back in the day. Everybody was like, “This is amazing. I can edit a web page.” It was really cool. You could link things together.

Then there was sort of half decent versions of that, like Google sites or something like that. Then you have your enterprise systems, like a Confluence or Sharepoint.

What’s the next level of innovation there? Is it the connectivity between systems, or lack of duplicating entry? How are you handling all that?

Shauni: One thing that we try to do is we try to make the default in Tettra super sensible. One principle we have is Open by Default. So, any page that you create in Tettra is visible to your entire team. We really think that, for most pieces of information that is the right default.

That doesn’t mean that you’re constantly looking at every single page, or you’re being spammed by updates to those pages. It just means that if you need to look it up it’s available to you.

I think part of achieving transparency is having that access to information with minimal barriers.

On the other side of things, because everything is Open by Default, we have to be very careful about how we present that information. Not everything is relevant to you at a certain moment, so making sure that notifications are super targeted to what you care about at that moment. Whether that’s only things from the department that you’re in, or only things that mention you. Even though you have access to everything, what you’re engaging with day to day is the subset that is relevant to you.

I think we’ve done a pretty good job of building the product around those principles for teams that are around 15 people to 150.

We’ve figured out that 15 is sort of the number where if you don’t write stuff down you get into trouble. You’re not all sitting around one table, and you can’t just ask your teammate where to get access to something. Then, bigger than 150 it gets to a point where you don’t know everybody on your team personally, and so that Open by Default principle starts to get a little scarier.

You have to have your tools be even more configurable to make sure that you are sharing the right things without too much meta work and mental overwork of, oh, who is going to see this? Can I make sure that everybody who should see this did see this? Those kinds of things.

Ledge: Right. Yet you’re solving a problem, or attempting to solve a problem, that has been part of every organization since the dawn of time. That, this is in a sense new approaches to old problems.

You probably looked at a bunch of existing systems and kind of went, well, it doesn’t exactly do what we had hoped for. It’s a crowded world with knowledge management. This goes all the way back to shared drives and calendars and email.

There’s all kinds of stuff and ways that people have tried to – poorly – address this problem. You can see it with Slack. It tries to integrate everything so you never go anywhere else. It’s like a whole collection of stuff, but it doesn’t necessarily capture an enduring view of the knowledge, or ultimately intelligence, of the organization.

How are you addressing that challenge in a different way?

Shauni: We have three tenets as part of the product. One is that it’s super simple. I’ve used Confluence and Sharepoint in previous jobs, and I became a Confluence power user, but it’s quite difficult to get to that point. If you’re not an engineer and you’re not used to writing in Wiki syntax for markdown, it can be daunting. I think Confluence is the type of system that you also need an administrator role who sets up all the spaces and the users and things like that.

What we try to do is just have something out-of-the-box that everyone feels comfortable contributing to. Everybody knows how to access. That you can access it straight from Slack if that’s already where you’re interacting with your teammates. It’s really easy to contribute information, so it’s not just like one or two people who are the experts. It’s everybody on the team has something that they can share with the team.

Ledge: Absolutely. I’ve experienced it as, you needed someone to always step up and be the librarian. Someone had to try to at least curate the indexes. Or like, how do I even remotely make this useful as it starts, because you want to collect everything. There’s good reasons to collect everything.

Along with that, what I experience with knowledge management implementations is, with any technology, it’s all about the adoption. I found that, growing out of Wiki to 500 or 1000 people that you had to change the way questions were asked. You had to change the way answers were given. It came to be like, “Well, don’t ask Ledge a question because it may affect the Wiki.” Right?

Shauni: Right.

Ledge: If the answer isn’t there, the answer ought to be written down and a link ought to be provided to the [anchor 00:14:12]. Then, if the [00:14:14 ] is wrong, you should go and change it. What do you mean I should change it? No, really, just click the Edit button.

Has that changed? Have you actually gotten past that?

Shauni: Definitely. Basically, what we try to do is encode exactly that workflow that you just described into the product.

So, if somebody asked a question on Slack and we have a slash command integration that you can just find whether that question is already documented in Tettra. If it’s not, we have an in-app action that creates that as a ticket – it’s called a suggestion in Tettra. You can assign it to whoever you think is the best person to answer that question. Then they’ll have this task as a little blue dot in the app, and gentle nudges every once in a while to be like, hey, you should document this thing because somebody in your team needs to know. Other people can give it a +1 if they also need to know and they’re looking for it and it hasn’t been answered yet.

Then, once you do answer it, as a person who’s writing down this information, you get a little bit of congratulations at the end because people can thumbs up your page. You get notified, oh, your page had 5 viewers, and the fact that something that you wrote down definitely helped a teammate. So that’s a big part of it.

Another thing around just keeping things simple of what we’ve done is, we’ve really stripped away almost all of the permissioning. Part of that is, one of the most frustrating things I found about using Sharepoint is that, even if something was there, knowing it was there was half the battle because your view of Sharepoint is completely different from another user’s view of Sharepoint.

So, to the extent possible, we’re trying to make it so that if I can seen in Tettra you should be able to see it in Tettra too.

Ledge: So you’ve gone all the way up through a bunch of kinds of organizations, software engineering, the whole thing. Now CTO. Talk about that journey. A journey that some people, I should say engineers, don’t even want to make.

How did you make it, and what was important in making the decisions to get there, where it felt comfortable and it didn’t feel like I’m not an engineer anymore?

Shauni: I think being part of this tiny team was the right middle step. I’m spending a lot of the time hands-on, building things. I would say 80% of the time I’m writing code or looking at pull requests. Then 20% of the time I get to do what is, to me still a little bit scary but also fun, of learning how to grow a team and how to mentor the new engineers that are joining my team. But also how to build an engineering culture that ships frequently, ships quality code, is proud of what they’re working on and knows what they’re working on is helping a customer.

Ledge: You get to set out and actually do those things. I don’t know how long that journey has been there, but what have you done to create that culture? The ship often and all that.

Shauni: I think I have a little bit of a chip on my shoulder from earlier in my career where I got a lot of, hey, you’re just a lowly engineer, you can just stay in this backroom and write code and you’re not ready to talk to customers.

I thought that was a very demotivating and limiting belief, for somebody else to be telling you what you are allowed to do and not allowed to do.

I think that plays a lot into how I think about building my team around making information self-serve and also [00:18:45]. One of the things that would have been helpful for me to know earlier in my career, but I was too afraid to ask and trying to make those kinds of things accessible to the team and making it okay to talk about those things.

I think that’s one of the decisions that went into Tettra deciding to do salary transparency – which was a super scary thing for us to do. We didn’t really have a lot of models of how it was done in other places. But so far it’s worked out great in that, when we bring on a candidate, when we give them an offer, we say, “Here’s your salary and here’s your equity breakdown, and here’s the spreadsheet of what everybody else in the company is making. So you can see your offer in context and evaluate it and ask us any questions about why you’re slotting in where you are.”

The tough thing for us deciding to do salary transparency is that, we are such a small team and we don’t have somebody in every single role. We don’t have a full fleshed out engineering career ladder. We’re figuring it out as it goes along. But I think it’s really empowering for the team to be part of that decision, I think.

Ledge: Absolutely. What happened with salary transparency that you both expected and kind of didn’t expect? What worked and what didn’t?

Shauni: I think the thing that’s unexpected is that it’s made our hiring process much smoother. We didn’t explicitly say, oh we’re not going to negotiate when we make this offer. We left that possibility open because we had no idea how it was going to go, and all of the candidates we’ve brought in thus far have not negotiated – which I found super surprising. It goes to show that, once you have all the information in context and it makes sense, you don’t have to fight against it. That process, I think it just aligns expectations super early on. “here’s the overall context of the team, and we’re super transparent about our revenue and our financials. So that has been really surprising to me, that everyone we’ve brought on has been very cool with the whole process.

I think the thing that is hard, and is going to continue to be hard, is as we grow, to have to constantly recalibrate. What if we’re not financially in a spot to do raises, or we’d figure out that somebody is super out of whack and we made the wrong decision, like we decided to pay them too much and there’s somebody else on the team who’s doing similar work who’s being paid less and we have to re-level and we’re not financially in a situation to do that. How do we make that kind of hard decision out in the open. Being vulnerable to the entire team to own up to a mistake that we made.

Ledge: Well, that will be interesting. We’ll have to do that in another episode. The firefighting episode.

This is awesome. Really cool. I’d definitely encourage everybody to check out Tettra, which is T-E-T-T-R-A. Is that right?

Shauni: That’s right.

Ledge: Dot co.

Awesome. So last thing, totally unrelated but fun, I have the lightening round for you. These critically important questions.

Star Wars or Star Trek?

Shauni: Star Trek.

Ledge: Wow. All right.

What are you reading right now?

Shauni: I’m reading a book called ‘Crudo’ which I picked up because I really like the food, but it’s just a novel.

Ledge: What can’t you live without?

Shauni: Comfortable pants – like yoga pants.

Ledge: Yoga pants. All right. Right on. What is the last thing you Googled for work?

Shauni: Probably how to do logging configuration for PHP.

Ledge: Not what I Googled, but okay.

I don’t know if you’re an Office fan, but there’s a classic episode where Jim is messing with Dwight. Jim always messes with Dwight. He is sending him faxes from future Dwight.

It got me thinking, if I gave you one piece of paper and one of those big, thick Sharpies and said you can fax yourself 10 years ago, what would you write on the paper?

Shauni: I guess, “You’re gonna do great.”

Ledge: Nice. Most people say, “Don’t open that door.”

Shauni: I think…

Ledge: No, it’s great. I love that positive outlook. Why did that come to your head.

Shauni: I think there was a lot of uncertainty. I graduate in ’08, just around the financial crisis. A lot of my friends had job offers that disappeared by the time they graduated. It was kind of an uncertain time and I wasn’t sure that I’d picked the right major.

A lot of that worked itself out. I think just having somebody on the other side saying that you’re going to be fine probably would’ve been really nice.


Ledge: You’d be a great mentor for yourself.

Shauni: thanks so much for having me. This was really fun.

Ledge: Well, Shauni, super fun to have you on. I totally appreciate it.

David is a Managing Partner at Add1Zero where his team provides lead-to-close sales execution for tech-enabled B2B services companies ready to leap from 6 to 7 digits of revenue. He is also a co-host of the Leaders of B2B podcast. When David isn’t working, he spends time with his five kids and frequently travels between Dallas and Nashville to keep his interstate marriage alive.