AlchemistX: Innovator Inside

E.07 - Cindy Alvarez: Discovering Customers

Published on

April 15, 2021

Cindy is the author of Lean Customer Development and the Director of Customer Research for GitHub where she works to understand what helps developers collaborate to build effective solutions and drive change within their organizations. She came to GitHub and Microsoft from Yammer where she was Director of User Experience. And today, she's on our show!

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Show Notes & References

Links:
@cindyalvarez — Cindy’s twitter
CindyAlvarez.com — Cindy’s website
Lean Customer Development — Cindy’s book
INPRO — A book Rachel finds applicable to this episode’s subject matter is thinks is a mind-blowing read
Mint.com — Finance website Cindy referred to
GitHub — Software development website Cindy is involved with
Yodlee — A software company Cindy was employed at
Simon Sinek — author of Start With Why
Karl Popper — British philosopher Rachel referred to
Paradox of tolerance — article by Karl Popper
8chan — online message board Rachel brought up
Donut — A Slack plugin GitHub uses that allows for watercooler talk, anywhere.
The Four Steps to the Epiphany — a book Cindy read that inspired her to write her own book
Hiten Shah of Kissmetrics — a person Cindy met who inspired her to write her book
PAL — An Alchemist portfolio company that empowers Humans with Problem Centric Innovations — Inspired by Autism in the family of the founder.
Intro and Outro music composed by: www.PatrickSimpsonmusic.com



Rachel Chalmers:

Today, it's my privilege and pleasure to welcome Cindy Alvarez, author of Lean Customer Development published in 2014. A book that I use and recommend in every single accelerator program that I run. Cindy is the Director of Customer Research for GitHub where she works to understand what helps developers collaborate to build effective solutions and drive change within their organizations. She came to GitHub and Microsoft from Yammer where she was Director of User Experience. Cindy's passionate about diversity and inclusion; supporting women, black, Latino, and girls in tech. 
Cindy, I have to tell you that when I get folks to take your advice seriously, to get outside of the building and talk to their customers, the results are absolutely transformative. So thank you for that book. 

Cindy Alvarez:

Of course, great! I'm always glad to hear that. 

Rachel Chalmers:

You are a leading voice in customer development at this point in history where even the largest corporations are trying to remake themselves to be more customer-centric. Can you talk about the challenges of taking customer development beyond the software industry - to banks, airlines, manufacturing companies - places like that?

Cindy Alvarez:

I think one of the things we see is that there's an assumption that software has an advantage because it's faster to develop than a lot of other industries. I actually think that's not quite the nuance. It's that it's much easier to control the delivery and to have more insight into how it's being used - because you can look at actual metrics. You've got an app, you can see who downloads it, you can see how often they use it. If you've instrumented it well you can see what features they use. In other industries, you're crossing so many more processes and people that it's much harder to look at the impact of what happens when you make a change. What people do is respond as they try and put a lot of metrics on humans. We've seen a ton of places where that actually works terribly. I think Wells Fargo is kind of the classic example of “if you incentivize humans to open accounts, they'll open accounts” but that's not actually what you want to do. 

Rachel Chalmers:

That whole, “You make what you measure.” problem.

Cindy Alvarez:

Exactly. I think there's this statement as a customer at the end of the day - I just want this thing done. The reality is that it's very difficult in a lot of scenarios because as a customer - even I, someone who's worked with Microsoft and seeing how many systems come together - I assume that companies have their act together. Surely they can just look something up in a database and they know all the information about me. If I stop and think, I know that's not actually the case. For most folks, it almost feels like a personal insult if you call your bank and they ask you who you are three times. We try and think - at the end of the day I just want my balance, at the end of the day I just want my bills paid. It's very difficult to figure out how we would enable that in a world where we're not just dealing with software, we are dealing with processes. I think one of the other challenges here is that in order to do that, you need to let people use their judgment and to reach beyond what their specific job is and help someone else. That's a very difficult thing to model and to train people on. I think it's what other industries are going to have to embrace. It's such a huge change from this notion of “you've got one person who is authorized to do this level of work and to do anything else, you need to go to a manager and that manager needs to go to a manager.” You're undoing how companies have been managed.

Rachel Chalmers:

That command and control structure came into the world for a reason. It was a way to have visibility into what everyone was doing. But we do work with more and more companies where that has outlived its usefulness. In order to survive and in particular, in order to compete with digital companies, these corporations have to somehow empower folks to do that reach outside of their box and to take care of the fundamental tasks. Not just the tasks that are written down for them. But that's so difficult because we have generations of workers who are acculturated to stay inside their boxes.  

Cindy Alvarez:

I think it's also the way that we've managed folks. They’re used to being told how instead of why. Even in very well-meaning corporations who have really tried to embrace an employee empowerment culture, it's very easy to default to telling someone “do this” as opposed to “do this because”. If you understand that because you have something a lot easier to work with. 
For example, if I'm trying to get some information on a customer and I go to our privacy counsel and say “Can I do this?” It's her job to say no if it has any risk of infringing on a customer's privacy. If I go and say “Here's why I want to do this thing.” I've empowered this person to say, “Well you can't do X or Y but you could do Z and that would be legal and I would feel comfortable with that. Does that meet your needs?” Then you can have a conversation. But that is not something that we've seen modeled. That's something that people have to invent for themselves. I think in software companies, you've got this - we're changing the world ethos - which for good or bad sometimes, that doesn't go as well as it should. You do more often see that model and I think that's where, in other companies, what they haven't gotten to yet is - how do we model that behavior? A couple of years ago, there was a big trend of having these Innovation centers within companies where we basically said, “Let's take a bunch of smart people and free them from the bureaucracy and let them work.” In some cases launching satellite businesses, great things happened. What you didn't have is modeling to everyone else. You'd see this resentment built like, “Oh you get to go have the fun job and be far away from the rules.” Meanwhile the rest of us just keep slogging along and you think if you take in that effort and invest it - everyone is going to learn how to form an experiment, form a hypothesis, try something new. In a very small scoped manner, where even if it goes totally awry, it'll be okay. 
That's the energy that we have to bring to larger corporations to say, “We've got to start small, we've got to figure out how we can let this ticket agent do something a little bit different. How we can let this wait person do something a little bit different.” Then actually collect that result and limit the damage if there is damage.

Rachel Chalmers:

It takes tremendous energy because there is this sense of damage control at that individual level. There is this sense of - if I stay within my lane, then I won't break anything and no one will yell at me. I see a lot of learned helplessness in folks at large organizations where the aversion to taking any kind of risk, even to help the customer, is deeply ingrained. When you look back on all the work that you've done, what are you proudest of?

Cindy Alvarez:

I think the thing that makes me incredibly proud is seeing - and I get to see the most of it across Microsoft -  seeing people frame questions in a way that will get them actual answers. I see a lot fewer yes-no questions. I see scenario based questions - “Tell me about this.” I'll hear people in their interviews or I’ll see things in internal blogs where people are asking open-ended questions or saying “Tell me about a time when...” or “How does this impact” instead of “Does this”. I think that's just amazing. A lot of people that are not necessarily in a workshop with me or talking to me, but have made these little subtle language changes that allow them to get so much more out of people and understand what's really going on.

Rachel Chalmers:

That's fascinating. It is so interesting that even these small changes in how you phrase speculation can point to these deep changes. I think Microsoft is one of the great success stories of transformation. From a company that at the turn of the millennium was allergic to open source and very much a command-and-control structure. To the company you see now which is one of the leading voices in open-source. Can you talk a little bit about what it's been like to live through that transformation?

Cindy Alvarez:

It is very funny because Yammer was acquired by Microsoft towards the very end of Ballmer’s tenure. I feel like someone being based in San Francisco who would go up to Redmond at these points of punctuated equilibrium, I could tell the difference between the first timers going up. There were co-workers of mine at Yammer who were told to cover up the Apple logo on their laptop. There was a lot of “We don't do that here.” And “That's not the way It's been done.” Or “Who are you, little startup - to tell us things?” As the CEO transition happened, you got a lot less of that. I will always remember there was an all hands where Satya Nadella was up there and he was talking about some app. I don't even remember what it was. He pulls out an iPhone and he's like, “This!” He was talking about a very specific user interaction, a workflow. “This is the sort of thing we need to do!” But the fact that he would cite Apple in front of everyone. I mean, I think for Old-Timers that was just a transformative moment. 

Rachel Chalmers:

It is a genuine case study in American corporate history because Ballmer was very much that generation of East Coast who came from a financial background. That kind of community where he was very attuned to what was happening on Wall Street. Whereas Satya comes up through engineering, and was super connected with the developer, and with the customer. Being a man of color and someone who has a disabled kid - being sensitive to points of view and in that sense as well. It's been really wonderful to watch the change, I have to say.

Cindy Alvarez:

Like I said, living it from a little bit of a remove - it's fascinating watching that difference. When I think - as the CEO - you have very little impact on people's day-to-day activities. You can say experimenter, you can say whatever your command to control is, but people will do what their direct managers incentivize. What you can really control is the tone and the top-down tone immediately becomes - like you said - multiple points of view. There are multiple right answers. We can learn more by asking, we can learn more by reading. We are not the people who are going to tell our customers what they need. I think there was a time at which Microsoft did that and that was perhaps the correct thing. In the early stages of computer software, customers didn't know what they wanted and didn't even know it was possible. But now we're at an age where even though most people don't understand how their iPhones work, they understand that there's a lot of things that are possible. So, we have to go in with that humility and say look if you're not going to give me engineering specs, but you can tell me a lot of detail about the thing in your life that's bothering you - that's holding you back from something. 

Rachel Chalmers:

It's interesting that you should mention reading as one of the key inputs because Microsoft has always been a very curious company and I'm one of the people who surprised myself. Because five years ago I wouldn't have believed that I would be waiting anxiously for Bill Gates' letter about what he read this year. But that curiosity is already there. I wonder if Satya tapped into that in a way that allowed it to come into a new expression. 

Cindy Alvarez:

The thing I said when I first joined Microsoft is that everyone here is just really earnest. They all believe that they are doing the right thing and some of them there have been people that I have deeply disagreed with. Some people that I found very unpleasant, of course as you would in any large population. 
Someone is doing this thing because when you open Microsoft Word, they want that button to work the way you expect it to work or because they fundamentally believe that this is the way an SQL Server should work. If you take this population of people who are very smart and very curious and very earnest you can kind of shape that river to say “We're going to flow this way now. We're going to listen a little bit more.” The job is still to do the best thing and to do what you think is right. We're just going to open our minds to more of those sources of what might be right.

Rachel Chalmers:

If you had one do-over in your career, what would you do differently? 

Cindy Alvarez:

This one is very hard to say because I think the biggest career mistake I made was also the one that laid the foundation for where I am. I had been at a software company called Yodlee which a lot of people know as being what powered mint.com I had a great time there and when the time came for me to move to another company, I chose poorly. I chose a startup that was not great. It didn't have a very solid mission, the founders were very happy about being Founders, but didn't really have a good sense of what they wanted to do. I judged badly and I got there and I was like, “This is a mistake.” 
I didn’t have a lot of options at the moment. It was a little bit of a downturn. I was very frustrated to be in a place where I felt like I couldn’t make a change. At that time, since I didn't know what I wanted, I should have gone to a larger company where I had more people to learn from. This was also a time when I was making the move from user experience to product management. The ideal thing to do would have been to go find a company with a culture of strong product management and go learn from people there. I had a little bit of an ego about wanting to be a director of product management at startup and that's what I did. On the other hand being in a company where I fundamentally felt like no matter what I do, this company is going to go down. It allowed for other things.
I participated in Google groups, someone had started this Google group called Lean Startup Circle that was kind of interesting. I read The Four Steps to the Epiphany. I started tweeting and blogging more. I met Hiten Shah of Kissmetrics. That's what led to me writing the book because of the things in “Four Steps” and “The Lean Startup”. What really stood out to me was this notion of customer development, of knowing your customers. It was something that I had done in past jobs without having a name for and suddenly I had a name for this. On the one hand I wouldn't have taken that job, on the other hand, who knows where I would be today. 

Rachel Chalmers:

That's a fascinating story and it points to one of the challenges that corporations have. Which is that you do need a certain amount of cognitive surplus to take on that exploratory spirit and to expand your horizons in a way to be able to ask open-ended questions. You have to come from a place of feeling that your basic needs are satisfied. Or if not, at least you know for now so that you can spend some time doing something else. 

Cindy Alvarez:

I love that phrase, “cognitive surplus”. I feel like that's one of the reasons that I've been incredibly happy to be at Microsoft. About 25 years ago I never would have believed I would be waiting for something Microsoft related. I've been an Apple die-hard all my computing life. Microsoft is a company that was not 25 years ago a place where I ever would have envisioned myself. But in today's Microsoft, that's changed. Secondly, as such a large company - there is a lot of room for people to take that cognitive surplus time to be someone who could invest in learning and teaching. 
When I was at Yammer, that part of my job was just going up to Microsoft and figuring out which teams were ready to adopt some of the engineering practices that we had adopted. Which teams were ready to do customer development, to think experimentally and that's continued to be part of my purview. Even GitHub as a standalone company. I still have relationships with teams within Microsoft. There's still that sense of, you have your job and also if you can invest 10% of your time in making some other teams smarter as a company, we will reap the benefits of that overall. Google’s ‘20% time’ is this kind of mythical thing that people praise and that a lot of Googlers say it doesn't quite exist. I don't think that as a notion, everyone gets 20%, makes any sense. But as a company and as a team, recognizing that there are times when, if you let someone invest this 20% it will bring you back tremendous returns. Having that faith will lead to really great things.

Rachel Chalmers:

It does take a certain cognitive surplus on the part of leadership as well. There has to be self-confidence in their own leadership. There has to be confidence in the team, that the non-directed time they’ve invested will pay off. So it's a privilege I think that belongs to companies that aren't under imminent financial stress. It's much harder to carve out that space when a company is in an industry that's extremely competitive or that's undergoing a lot of transition. 

Cindy Alvarez:

Yeah. 

Rachel Chalmers:

We've talked about a few things but is there anything else you think contributes to how difficult corporate innovation is? I've talked about it being the highest difficulty level of playing the Innovation game.

Cindy Alvarez:

It is absolutely. I think what makes it so difficult is that there are so many - I've talked before about the people and process piece and how the downstream effects are not always visible to you. So, if you're in a small company and you decide you're going to do something different and in doing so you have inadvertently made life much harder for your product marketing team - they sit a few cubicles over. Maybe in today's era they are one Zoom call away, but you know them by name and they know who you are. 
They know who to come to and say, “Hey this change you made is killing us. Why did you do it? How can we work this out?” In a corporation, a change you make is often invisible. You don't know who that person is that it's impacting downstream. Again learned helplessness. You mentioned that phrase. It's another thing that I talk about a lot - if it's hard for you to find who to talk to, if it's hard for you to figure out what questions to ask - you often won't. Because humans fundamentally hate feeling dumb. We just will do anything to prevent it. That is where cognitive bias comes in. That's where a lot of people being really mindlessly cruel comes in. We just really don't want to feel foolish. In that small company you can do these kinds of micro explorations where if I have an idea, I can kind of say “Hey, what do you think about this thing?” to my neighbor over the cubicle or that I've got on slack DM. 
I can wait and see - do they immediately shoot it down? Do they ask a question? Do they give me kind of a polite demerol? Based on that, I can decide what I want to do to build up this idea a little bit more and polish it and share it to another person. In a corporation you still have your work buddy, the person who can actually tell you if this is a good idea or not. You might not know who they are. Or you might know who they are but not have that relationship where you can ask for 15 minutes of your day and not have anything in return for them. It can be very awkward.

Rachel Chalmers:

Awkwardness is almost worse than feeling dumb - that social hesitance. But there is this real need for the ability to reach across hierarchical lines. Where in a corporation, a lot of the teams have formed this defensive posture where they bond over saying “Oh, well that's an IT problem - those idiots down in IT they don't know what they're talking about.”

Cindy Alvarez:

It is a very defensive “us versus them.”
I talked about modeling before. This is another place where it is very difficult and it feels almost silly - like common sense. Like, “You shouldn't have to do this.” But you absolutely do. What does it look like to cold outreach to another team that you don't know and ask a question? How do you frame it so that it feels like less of a burden to them? So it feels non-threatening. How do you set up this expectation that they will respond to you? I think even pre-Satya, Microsoft had a culture of informational interviews where it was basically expected that if someone asked you for 30 minutes to find out about your team or about what you were working on - that you would grant it. Because the expectation was that you’d be there for a lifetime. 
That's another thing that big companies have. There are people who are there for a long time and so they know that any investment they have paid out, they'll get back. On a micro level, GitHub uses a slack plug-in called Donut. It's this little thing that facilitates chats between random people who have joined a Slack channel. What that does at this level is basically normalize having a 20-minute conversation with someone you don't know. It gives you a prompt that reminds you to set up the time. Everyone's opted-in because they've joined the Slack channel. It’s a  model that helps to talk to someone you don't already know. When you think about a company, how many of those you could do in a way that would facilitate this communication. How do you disagree with the manager? How do you politely say “I don't know why you suggested that it doesn't make any sense to me? Maybe you've got context I don't.” There's a way to say that at work where you actually come across in good faith and you get that answer. There's a way where you're told, “Stay within your lines and go back to work.” I think that knowledge - we assume it exists, but it really doesn't. It's like if you're a kid who lives in a remote area. You don't necessarily have the skills to make friends built-in. You don't necessarily have the skills for disagreeing across team lines or asking a manager why they've proposed this crazy thing. That's really fundamental to all of this. If you're going to trust someone you have to give them the tools to do something. You wouldn't send someone out to chop down a tree with a rusty knife. How do we bring customer development? How do we bring customer-centricity into a company? The first thing you have to recognize is that your first line of customers is internal. 

Rachel Chalmers:

It's not enough just to have a visionary Innovative leader. There's this layer underneath the c-suite that has the responsibility for executing. If those folks are just  hunkering down and waiting for this new leader to fail and for the old regime to reassert itself, then no matter how inspired people are at the individual contributor layer, they run into this wall of resistance from management that is death to any Innovation project.

Cindy Alvarez:

Things like, is this an expectation or a trade-off? Because whenever change comes, you can't just add it on top of what you are already doing. Most people's jobs are pretty full up. If you say, do all the stuff you've been doing and then spend 10% of time on Innovation, that's going to be the first thing to go. It's last on first off. 
If instead you say, let's look at what everyone's doing today and throw out these things that no longer serve us well. Every company, no matter if it is a startup or a giant company, you have things that you started doing at the time, they were the right solution and they're no longer serving you well. 
You can slash them off your task list. If you're very honest about saying, “Let's stop doing the things that are not making a difference.” then you free up some time. At a leadership level, the CEO is not going to do that. But someone a couple levels down needs to be saying in order to do this, we've got to take some things off. So let's think about what things we can take off the stack. Having that conversation at multiple levels helps facilitate that. It helps make everyone feel more confident. “I can do this because I'm not doing some other thing.” 
A lot of the times that stuff that we shouldn't be doing, people are happy to get rid of.. Most humans at any level recognize when something they're doing is pointless and it's kind of a relief to say. “Oh thank goodness. I never understood why we were doing this in the first place, let’s stop.”

Rachel Chalmers:

I have seen the unfortunate converse situation where people are incredibly invested in their zombie project. People have tried to kill the zombie projects, but they keep coming back up out of the earth and it's very very difficult to build consensus for stopping doing something in a large corporation. It’s this cargo cult belief that if we just keep on “doing”, things will be okay.

Cindy Alvarez:

Again, that's another modeling behavior. Have you ever seen a thing killed where people got a reward afterwards? It feels like leadership has to pick something to be the sacrificial lamb that you can then praise. They say, “I had this project, it was really great, I launched it, everyone told me I was fantastic. I'm going to get a promotion.” Then we've seen the reverse of “Oh, someone was working on the project, and the project got killed, and some people got laid off.” Another thing that can happen is that some people who were leading the project are now non-leaders on some other thing that they didn't want to do. Those are bad endings. I think we can actually orchestrate happy endings where you can look for something and kill it. Then talk about how great it is that this thing was not yielding the results we wanted - it was in fact wasting people's time. So, we've killed it and we've taken everyone who has worked on it and we have let them do their pet project or we have put them on this new shining thing that is the hope of the company. It doesn't have to be a major release. But even small things such as a team pointing out that the way they were doing this meeting wasn't serving them very well. They've taken on a new way of doing this meeting or keeping track of this customer thing and everyone is happier now.

Rachel Chalmers:

It's a great idea to start with meetings because there is no gift to anyone more beautiful than “We're going to cancel this meeting and give you back your time in perpetuity.”

Cindy Alvarez:

Meetings are such short term things that I think a lot of times - I had the notion of permanent change is terrifying. While the notion of an experiment, even if you hate the experiment, is a lot more bearable. Because at some level even if you're a skeptic who doesn't want change, you're thinking, “Well in three weeks, I will be proven right.” And that allows you to go along with this. You think, “We're going to try it for three weeks and see what everyone thinks.” That's a very short term experiment. People will sign on to that more readily than they will to “From now on we are making this change.”

Rachel Chalmers:

Cindy you've had so much amazing experience across so many Industries. How would you distill all of this into two or three lessons for our listeners? 

Cindy Alvarez:

Oh gosh, let's see. I think the first thing to mention is Start with Why. It’s a great book by Simon Sinek that goes into this in detail. It asks questions like, “Why are we doing this?” Aiming to make it normalized for anyone to ask ‘why’. 
Again this is where having a formal set of words can help because blurting out “Why?” often comes across as kind of accusatory. But instead to say, “Hey in this company, we always want to make sure we understand why we're doing things.” 
If you're ever in a room where you don't understand why, it is okay to say, “Hang on a sec, can we take a step back? I want to make sure I understand why we're doing this.” Everyone in the room should respond with good grace. Starting with that gets you so far. There's so many times I've come into a room - someone asks ‘why’, and everyone realizes “Oh, we're not really sure. or “We started out on this path and we've made some changes and we're not sure that we ever relined.” 
So starting with ‘why’ and making it okay for everyone to ask ‘why’. The other thing is always thinking about the customer saying, “” - so anything you're doing, whether it's an internal change around process So what?” Think about that stakeholder who hasn't put the time and effort into planning it. All they're seeing is the end result and they're thinking to themselves, “So what? Why do I care?” It's like if you make something five percent better, that is an improvement. And also the customer is probably thinking, “I guess it's a little faster, what's the big deal?” And sometimes that means that maybe you shouldn't invest in making something 5% better. 
That sounds terrible on its face, but honestly, there's probably something with a much higher yield that you could do. You could take away a feature that allows someone to more confidently make a choice because now there's not that “Wait, should I choose that option?” Maybe it's streamlining a process, maybe it's taking a completely new track. Taking that and always thinking about it from the eye of the skeptic. 
A lot of times that's helpful to do within yourself. While you should always get outside of the building and listen to other people. It's a lot faster when you can train yourself to say, “Okay, I'm going to ‘so what’ this.” The best tool I found for that is reading things out loud. Anything you've written, anything you plan to say, say it out loud and you will notice like, “Wow that sounds like weird corporate jargon and everyone who hears it is going to agree. Okay, let me rewrite this.” 
Finally, the improv, ‘yes and’. ‘But’ makes people defensive. It makes people close-up. ‘Yes and’ is magical when you can stop and say, “Yes, and also here's one of the things that makes that difficult but how might it still work.” or “Yes, even if... blah blah.” “Yes, I hear you and then the details.” Because then people keep listening and when someone suggests something and maybe it's not a possibility or a good idea, everything goes more smoothly when they come to that realization themselves. “Yes and” is such a powerful tool for getting people to that realization themselves. Or getting you to say, “Yes, and oh actually that's a great idea. It wasn't my idea which is why I immediately rejected it - I'm a human - it wasn't my idea. But now that I've said ‘yes and’ and thought about it actually yeah, you're right we should do that.” I think when we have those, when we practice those, magic things happen.

Rachel Chalmers:

These are fabulous lessons, but what's striking to me about all four of them is that they're drawing on history, context, and rhetoric of theater. The things you’re talking about are soft skills that come from the liberal arts. I don't know whether you saw that the creator of 8chan was saying, “As a 19-year old building a software service, I sure wish I'd known who Karl Popper was and what the Paradox of tolerance was. 

Cindy Alvarez:

Yeah! 

Rachel Chalmers:

How do you think the pandemic might affect corporations in the long term? 

Cindy Alvarez:

It's very interesting the degree to which the FaceTime myth has crumbled. I think to some degree there will be people who can't wait to get back to offices. I personally can't wait to have a space when I'm not going to be interrupted with a request for mac and cheese or whatever else.

Rachel Chalmers:

Lighting a candle for all of the parents of young kids at this time. Thank you for your service. 

Cindy Alvarez:

I think there's this myth that having people in the same space all the time is necessary. There's been a ton of really good collaboration. I think a lot where - because time has bled into evenings and weekends - and that part is not great - things are more amorphous. What I've seen happen is that instead of a decision getting made at the end of a 60 minute meeting because everyone's going to shuffle off to their next meeting. Instead, there wasn't the right amount of information or maybe the loudest voice in the room just made it. I've seen things where a decision gets left open-ended and then someone trickles back in at 8 p.m. and is like “Hey, I was thinking about it more and I wonder if we could do this thing instead.” I think the freedom to set work down and go do something else and come back to it is tremendous. 
Right now it's not under the greatest circumstance because when you set your work down what you’re going to do is some laundry, feed a kid, or watch Netflix to ward off the crushing existential doom. That notion that intellectual work should be nine to five, always seemed odd to me. If you look at - again going back to history - you look at great inventors. They were not sitting in their workshop from nine to five. They were getting up late and thinking about something or going out and wandering outside and seeing an apple fall from a tree or a bird flying in the air and they're like, “Oh that is a principle I can bring back into my work.” I think the notion of “Let's let people work at the time when they're most able to work is very powerful.” I would expect to see a lot more flexibility in terms of - sure we have this office, maybe you come into the office a couple days a week. The other time you work in a way that's more constructive to you. 

Rachel Chalmers:

Yeah, I think we need to have a little conversation about work-life balance because the quid pro quo to being on Slack at eight p.m. means you have to have downtime at three p.m. That has to be understood. The Union worked for eight hours for work, eight hours for sleep and eight hours for what you will. We've lost sight of that basic human need for open-ended non-directed time. 

Cindy Alvarez:

Yeah. I think that's one of the things I've tried really hard to model. In my Slack profile at work, it has a very clear link to my work schedule. I go offline from three to nine, that is non-negotiable - I have kids. I get up early but I'm off at these times. In the past it was a different middle of the day chunk. Nope not going to do it. You can't schedule me for meetings, I will decline them. As a leader I want to do that and normalize it. Yes, I might be working on a Sunday one day, but that's because I was homeschooling a kid from twelve to four or that's because I took this time off. I mean again, it comes down to trusting people. If you have people who are interested in something and they understand why they're doing it, they understand the importance of it - most of them will get it done. 

Rachel Chalmers:

It's a fundamental philosophical point though. I mean some people believe people are basically well-meaning and hardworking and that they will contribute and build something even if you're not coercing them 24/7. Other people just genuinely don't believe that, they believe people are lazy. If you're not surveilling them, they won't do anything and it's very hard to persuade those people to take a risk and trust their folks. 

Cindy Alvarez:

Why can't it be both? We are human, we are fundamentally lazy. There are times when we don't want to do things. I would say - okay, well when that's true, let's look at that. Yeah, I'm not going to discount that, there will always be some people who are just never motivated in the same way that there will always be some people who are incredibly motivated. Who works 16-hour days or you know, are constantly thinking. Let's say okay if we have times when workers are being lazy and the only way to get them to do something is to watch them and crack the whip, then why is that - talk to them, figure it out. Why is that? Is it because the work they're doing doesn't make sense to them. Is it because they'd rather be doing something else? Is it because they don't understand why this thing is important? You can never solve for everything but you can solve for so much by understanding why this thing doesn't make sense. When I was at Yammer, I remember we did some research on retail workers for whatever reason. People who worked in mall retail. They would talk about their jobs and they were pretty much clock-watching from 9-5. Like, “I have this job because it pays the rent and that's it.” In talking about parts of their job that they enjoyed and didn't enjoy, the parts that they were like, “Oh, I hate this” didn't make sense. They were things that were, “Oh, well, I have to do this thing this way with this equipment... blah blah blah.” When I would ask why they do it, they would say, “Well, I don't actually know. All the time I've been here no one has ever explained it. It doesn't make any sense to me. It doesn't seem like it's doing any good. All I know is if I don't check this box, someone yells at me.” I wouldn’t be super eager to do that either. It was also that, “If I do a good job at this, I don't get any praise. If I don't do it, I get yelled at and also if I do it half-heartedly, it doesn't seem to make a difference - so why wouldn't I just do it half-heartedly?” That's exactly what I would do.

Rachel Chalmers:

50 years of research into animal training and we've clearly established negative reinforcement doesn't work but it hasn't trickled through to human management. 

Cindy Alvarez:

Yeah, I know. These people are being lazy and they won't do what you've tasked them with unless you threaten them. Let's understand why that makes sense. Is there another model?

Rachel Chalmers:

How do you personally avoid burnout? 

Cindy Alvarez:

I have children and that means that I have no option to work too much. Especially now, they will physically pull me away from that. I have always worked better as a bursty sort of person. While I don't like being in my house all the time, the pandemic is actually kind of aligned with my work style. Some days I will get a ton done, it'll be a huge step forward. Some days I'm like, “I don't really know what I accomplished here.” That happens on the week scale as well. So, if I am not being productive then I just won't work. I do the meetings that are absolutely necessary. I'll do what my team needs to keep going and then I'll just call a mulligan on today because I know there's no point. And again, I'm glad that I have the freedom to do that. I wish more teams and leaders would recognize that tendency in humans. If you have a job where you've got to change someone's IV medicine or if you got to sell the tickets, then you've got to do it. But when you have intellectual work, you're not always going to have good intellectual days. Sitting there and trying to make it happen is just burning out something that we don't have an endless capacity for. It's like burning out this energy that is not boundless. You're not doing great work today, forget it, go for a walk. We should all do that more. 

Rachel Chalmers:

It's such a pleasure to hear you talk about the kids because I really felt that my career kicked into high gear when I had children. I was working fewer hours, but they were way more directed because I really just wanted to get back to the kids. Everything I was doing had this much more visceral point to it, it was helping to build my children's future

Cindy Alvarez:

It made me ask ‘why’ about everything I did. I wonder why am I doing this, is this important? If I don't do this will bad things happen? I removed so many senseless things from my list because I was like, this is not actually the most valuable thing I could be doing. 

Rachel Chalmers:

Yeah, you don't work as performatively anymore. You're just like, “Is this more important than reading a bedtime story? It is not.”

Cindy Alvarez:

There's actually really interesting research about this that peers average your accomplishments. If you've done an amazing thing and another amazing thing and two like middling things, you actually seem less impressive than someone who just did two amazing things. There's been really interesting research in people's resumes around this. Like if you've got the great bullet points and then the meh bullet point, it drags you down. I think the same thing is true in an intellectual way. 
Doing those middle things actually doesn't make you seem better. If anything it's hurting you. What we really should be incentivized to do is the best things and the most important things. That doesn't mean they're always going to be the things we like. There's certainly things I do where I'm like, “I don't think this makes any sense but my boss is really big on it.” But if I'm going to do that thing, I'm going to do it in the best way that I know and I'm going to think as much about the outcome as I can. “I don't think this makes sense, but I think the desired outcome is this and so I'm going to work as hard as possible to get that desired outcome so that I can cross this off my list.” Then get back to, doing things with the kids or whatever else is my priority. 

Rachel Chalmers:

I sometimes think that being middle class is just all about internalizing deferred gratification. If we can just pay this mortgage for 30 years then we will own the house free and clear. If we can just put in the work now, then there will be a payoff later. 
What is the best way for our listeners to connect or follow your work? 

Cindy Alvarez:

I tweet pretty regularly on Twitter @cindyalvarez. I have to admit the blogging has fallen off a bit since I've been in quarantine. You can also just email me. I get random questions - people reach out to LinkedIn or at CindyAlvarez.com and I do actually really enjoy hearing from people about what they're trying to do. Honestly if someone comes to me and says, “Here's my problem, I'm trying to ask this of customers. It doesn't seem to be working.” I really love diagnosing those because it's like it's a short thing where I've seen the pattern so many times that I probably know what you should try. I'm happy to share that wisdom! A lot of times people are a little bit shy about contacting folks who have done a lot of work in an area like, “Oh this is going to be seen as free consulting or they're probably too busy.” But the truth is that problems that we've solved a lot of times are very satisfying because I can solve it quickly for you. Whatever else I have facing me in my days is probably more complex. So, somebody sends me a review of a customer development script and I'm like, “Oh, okay! These are the three things you need to fix - boom, boom, boom.” I can rattle that off and send it and I feel like, “Wow I did this thing in 90 seconds, and I probably saved that person three weeks worth of work.” 

Rachel Chalmers:

Is there going to be a new edition of Lean Customer Development

Cindy Alvarez:

I don't know that there's much I would change. It's one of those things where in 2014 my personal bias is if I see a textbook that's more than three years old, I don't trust it. I've read it at three-year intervals to see if it holds up.I think it's so fundamentally about how humans behave that with the exception of things like, no you probably can't recruit people off craigslist effectively. Otherwise it's pretty solid. I don't know what I would put in a second edition. I do think there's probably another book in me about some of those generalizations - so here's how you talk to your customers. A lot of your customers are your co-workers. It's your manager. It's the people on your team. It's that team over there that always seems like they don't get it. If you can work with these folks you can apply some of the same techniques - they know where you work. 
But how can you take some of these questions you'd ask of customers and apply them internally? Whether it's a tiny project or a large scale enterprise change project. I think that's really the direction I'm heading in now - you're using a lot of the same questions and a lot of the same principles, but there are nuances. I think being within Microsoft - even GitHub is a pretty good sized company. It's taking those questions and applying them with the right nuance to use them internally.  

Rachel Chalmers:

That one sounds really powerful. I will definitely preorder it. Okay, now I'm going to give you a magic wand and you get to dictate what happens in the next 10 years. In 10 years time the industry will be - the software industry let's say - is exactly as you would like it to be. What does it look like? 

Cindy Alvarez:

Ah, that's a good magic wand question. Okay. Let's see. So the software industry has gained a lot of humility. We still have incredibly smart people who have a great reality distortion field impact. But a lot of the source of - what are the problems - is coming from outside. I think if there's been one thing that's been frustrating to watch, it’s the immense amounts of talent thrown at problems that are not that useful. That doesn't have that much impact or that has an impact on a very specialized population. I recognize I'm one of the beneficiaries of this population  - being someone who lives in a city with a high income and very tech-savvy. There are so many things that serve me but there's so much more out there and I think the notion of wanting that ‘so what’ to be bigger and more impactful over just glamorizing the technology.I think that's where I would want things to be. 
That software has an incredibly democratic entry point, anyone can learn to code. Anyone can learn low code or no code solutions. Embracing people who've come from non-traditional backgrounds - means that the flow of problems coming in is not so constrained. You've got people coming from, “My dad is running a dental office that's barely scraping by. This is how the solution I built has made his business better.” And “I grew up in a family with eight kids and we were always running out of things and here's a solution I found that makes this better.” Or “I have a brother with autism and here's something that made his life better.” Bringing in that wider scope of solutions and recognizing that while there are some things that require vast amounts of computing complexity, like the way that Google Maps knows how fast the speed limit is exactly where I'm driving. Tons of engineering went into that, amazing! Also something that makes a glorified air table for a busy parent or a school administrator who's trying to educate kids with different needs -so much more impact. 
I would love to see that more voices are building solutions and more voices talking about what the problems are. Along with a recognition that that's a more glamorized thing. And I think what comes along with that is probably a change in Venture Capital. Because it rewards the hundred X return. I don't think that's ever going to go away. But if I had my magic wand and I could make things be a way, it would be that there is a larger bank of investors who say “Hey a 5x investment is pretty great. And I'm going to invest in more things that are mission driven because I'm not actually making my fortune off this.” Maybe I'm a software person and I'm an angel investor and I have more information and more access to say - this is a solution that's after my own heart. Even if it makes 2x returns, I'm going to be happier that it's in the world and I will have created jobs and I will end up richer. I think that's what opens the door for so many things. Because there's so many businesses that are never going to be a hundred X and yet they can make so many people's lives better. 

Rachel Chalmers:

That sounds like an awesome software industry, I would like to work there. For listeners who may not be aware - that startup that was started by a founder whose brother has autism is real and it's one of the Alchemist portfolio companies. (PAL)

Cindy Alvarez:

So excellent!

Rachel Chalmers:

Did you know that Cindy? 

Cindy Alvarez:

I did not. It's a use case of something that is - if you live it. I don't have anyone close to me with autism, but obviously I have a lot of co-workers, Microsoft tech industry in general. It's like so many things if you live it, you know the complexities in and out and if you have figured out the thing that works - and I would generalize that to parenting too. If you have a kid with a weird quirk and you have figured out this thing that works, then it makes such a huge difference. If you can band together these little tribes of people with a very specific problem and solve that for them - it's just life-changing what you can do. I'm glad though that actually exists. 

Rachel Chalmers:

Is there anything else that I should have asked you that we didn't already cover?

Cindy Alvarez:

Let's see...I got to answer a magic wand question. I got to talk about, ‘yes, and.’ I'm not sure, I think this is actually pretty good. 

Rachel Chalmers:

That's high praise coming from you Cindy. Thank you so much. It’s been such a delight to have you on the show. It's so great to spend time with another badass Mom making waves. Thank you so much for your time. I really appreciate it and I'm sure our listeners will as well. 

Cindy Alvarez:

Thank you so much for having me!

Get to know the Team

E.08 - Alan Boehme: Next Stop, Space!

April 15, 2021

"You want to keep them motivated, you want to keep them moving forward, but at the same time you want to make sure that they understand that there are lessons to be learned and they should listen. People get too close to what they're passionate about and sometimes ignore all the facts." - Alan Boehme

Play Episode

E.07 - Cindy Alvarez: Discovering Customers

April 15, 2021

"When you have intellectual work, you're not always going to have good intellectual days. Sitting there and trying to make it happen is just burning out something that we don't have an endless capacity for. If you're not doing great work today, forget it, go for a walk." - Cindy Alvarez

Play Episode

E.06 - Sam Ramji: Seeds of Change

April 15, 2021

"We will slowly uncover what is actually special about being people. I think that's our ability to love, it's our ability to create, our ability to connect with each other." - Sam Ramji

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E.05 - Christi Zuber: Innovation by Design

April 9, 2021

"There is purpose in all sorts of things that we do. If you can make someone's job easier, if you can help someone sleep better at night, or whatever it is. Reach out and have those conversations. Understand the context of the people that interact with those products and services." - Christi Zuber

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E.04 - Corbett Gilliam: Advancing Technology

April 9, 2021

"I think a big piece of working with enterprises is, everybody knows they need some type of Innovation. And a lot of them think that they are innovating when they're really not." - Corbett Gilliam

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E.03 - Louis Stewart: Mr. Innovation City

April 9, 2021

"Everybody has different needs in order to be successful. So trust your gut. If a door opens, give it a shot. Go ahead and take a look inside the door and see if there's something in there that you can learn from." - Louis Stewart

Play Episode

E.02 - Jeanne Morain: Transformation Pioneer

April 9, 2021

"It's important that you find those change agents. Because they exist. In every pocket, in every group. There's always those that aspire for a little bit more." - Jeanne Morain

Play Episode

E.01 - Mike Dolbec: Venture Industrialist

April 9, 2021

"You can't believe everything you read, see, or hear at first glance. Just because we're pattern-matching animals doesn't mean that your conclusion is accurate. It just means you matched some pattern. That pattern may or may not be useful at all." - Mike Dolbec

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