Joe Giglio on making remote work, work for you

Pushpak Mundre

Hey guys, welcome back to another episode of Be remote podcast. I’m your host Pushpak for today’s episode we have with us Joe Giglio. Joe is the creator of Gold puppy, remote scorecard and remote work masterclass. He is the author of making ‘remote work’ work for you. And Currently he is working as an engineering manager at nomad health. Welcome to the show. Thank you for being on the podcast.

Joe 

Sure. Thanks for having me. pushpak, appreciate it.

Introduction

Pushpak Mundre

Awesome. So let us begin with your introduction about yourself.

Joe 

Sure, I’ve been in the internet space since the mid 90s. I started my career doing tech support for a dial up ISP if you remember what that is, not sure how old you are. Since then, I’ve worked for a bunch of startup. And my expertise is really in ticketing software, help desk software, call center CRM software. And I’ve worked remotely in some respect for most of my career. I’ve been a manager and director building support QE and engineering teams. And in my last role, I was the first hire for another startup named assist Lee. And we were one of Zen desks main competitors, and we got acquired by Salesforce. Stayed with Salesforce for about nine or 10 years, I stayed with them until the end of that project. And I ended up leaving Salesforce, the company was really not remote friendly at the time. And they really wanted leadership out on the West Coast of the US. They really wanted people in San Francisco. I was moved so we parted ways. And even though Salesforce really didn’t like remote work at the time, I had worked remotely for quite a while and I decided to publish a book and a video series on remote work. And I was starting to see a lot of traction online on Twitter, LinkedIn, a lot more people were becoming remote work advocates, there were a handful of companies out there that were building remote first cultures. They were publishing books, publishing blogs, and teaching other companies how to do it. So I decided I would try to do the same thing. Like I said, publish the book, publish the video series, I got into a little remote work consulting, and then I crippled patients to hopefully improve the remote work culture. Anybody who wants links to any of my projects, you can find them on Chief remote officer.com. And as you mentioned, next week, I’m starting a new role at Nomad health. And I’ll be starting there as an engineering manager.

Pushpak Mundre   

Awesome. Sounds amazing. So what made you build and you know, create these multiple products in your workspace? Like you’re the creator of the whole puppy and all these things?

 What made Joe to build products in remote space

Joe 

Sure. Yeah. The two projects that I recently built, one is called Remote scorecard the other one is called Gold puppy. And as someone who’s worked in challenging environments, I’m trying to create applications for vacation material to try to improve the remote work experience. I am yet to work for a company that is truly remote first. I’ve worked in companies that maybe didn’t really love remote work, but we had to make it work and I had my team scattered all over the country, if not all over the world. So I have a lot of experience building highly functional teams in environments where maybe remote is really not preferred, but I know how to make it work. So my book and in my masterclass video series, were really just a brain dump of all the knowledge I had picked up over the years in combination of some of the best practices from those great remote first companies companies like GitLab and Zapier and HelpScout and tax jar, these are companies that have have been publishing blogs on how to do remote first long before anybody else was doing it. Yeah. My other project was a remote scorecard. And the point of that project is that the remote work I’ve come to learn is really a spectrum. What I mean by that is to some companies, remote work might be that you work from home maybe a day or two week. Other companies, maybe you work remotely from a satellite office. Other companies really push you to the extreme and you have people backpacking across Europe or working from the rim of a volcano or living on cruise ships or living in RVs. And there’s people that are working and very productive in those environments. The point of remote work is, I found that the best remote companies follow about a dozen workflows and criteria to build a great remote culture. So if you go to a remote scorecard and add your company, there’s about 15 or so questions. You submit the form and an algorithm will give your company a remote score based on some of those key criteria and workflows. Okay, gold puppy is my other recent project. And what I’ve learned is it can be challenging for managers to build relationships and trust with their team members. This is especially true on remote teams, you might never meet your team, you might meet them maybe once or twice a year. And this is coming from somebody who has managed remotely and also had remote managers. So the point of gold Puppy is to work with your manager in your team to create your goals and collaborate and try to increase alignment and trust between management and the workers. And some of the challenges, typically faced by remote workers, are that they might feel like their career is stalled. Or they’re seeing a lack of advancements, lack of recognition, lack of relationships in the company. And when you’re a remote worker, sometimes you don’t really feel like part of a company. So you should work on goals that are time based, and work with your manager to collaborate to come up with goals that are clear. And time and date driven. That’s the point of gold pubby.

Pushpak Mundre  

Okay, awesome. So as we’re talking about, you know, building trust and building good relationships with employees, so how do as a manager, how do we build better relationships and trust with our employees.

Building trust and better relationship with employees

Joe

A lot of it really starts with proper onboarding. One of the things that I did while I was at Salesforce was I built part of the onboarding program for anybody that was joining the project I was working on. And this was a week long, deep dive into the company, company history, meet the key people meet product management, do system administration on our products, understand the product roadmap, work with the support team, and that really helped people to get a great foundation into what the company did, how the products worked, how customers use the product. And I think a good solid foundation like that really helps people feel like part of the company. A lot of times your heads down writing code, and you lose sight of what the company is really working on. I think a nice and immersive onboarding program like that will help set the foundation for your workers to make them feel like part of something and break them out of their bubble a little bit. I think that’s pretty important. I’m also an advocate of what I’ll call mentors and milestones. Again, part of that onboarding is to have a couple of mentors in the company, you have a couple of mentors, and the mentors will be people that are in the company that can help you get things done in the company. They might not be on your immediate team. It’s actually better if they’re not always on your immediate team. And these would be people that can help you navigate the company, figure out how to get things done. I think that’s pretty important. And having data driven milestones is also pretty important to build on that alignment.

Pushpak Mundre 

Right? It makes sense because I think I have observed this in a lot of companies like when someone new is joining. They are mostly clueless. They don’t know what to do, because of you know, this, they don’t most of the companies don’t have good onboarding process thats what i felt. Yeah.

Joe

So I’ve seen a lot of onboarding it basically, basically, a lot of onboarding is focused on just setting up your laptop and setting up your development environment. And that’s part of it, obviously. But the onboarding that I’ve seen work very effectively is more of a deep dive into the company, the culture and meeting more people. And that’s especially important, I think, for remote workers where, like I said, you might not ever get a chance to meet everybody or you might meet them once a year. So I think it’s very important to get that foundation set early. If you can.

Pushpak Mundre 

Yeah. So tell us about your book. So you have written this book in 2019, right that at the time pandemic, like was about to start or, you know, wasn’t started in West and other countries. So like, it wasn’t even that mainstream. So what made you come up with this book and tell us more about the book?

Joe’s book 

Joe  

Sure. I think the first edition, I believe, was published at the very end of 2019. After I left Salesforce, and like I mentioned, I was starting to see a lot of traction online, a lot more remote work advocacy, and a handful of companies that were really doing remote work the right way. Now, this was a brainstorm, like I mentioned earlier, of things that helped me build successful remote teams, and a combination of best practices from some really great remote first companies. So I published that in 2018, and then the pandemic hit. And you had a lot of companies that were forced into remote work situations and just trying to try to figure out how to survive. So I moved into trying to do more remote work, consulting, and then I moved into the companion video series called the remote work masterclass. And what I try to teach in the book in my masterclass is an honest assessment of remote work, the benefits and the challenges and there are some very real challenges. I go through that in my teachings. And I also said remote work spectrum, like I mentioned earlier. It’s very important, I think, for companies and job seekers to really be honest about what they’re offering in a remote role and what they want in a remote role. Are you okay, like I said, my examples before you work from home on Friday? Is that good enough? Maybe it is, it saves on your commute, saves on your mileage and gives you back a few hours a week? Or do you really want to push it to the opposite extreme and be a true digital nomad. You don’t know where you’re gonna. You don’t know where you’re gonna work from next week. And in some companies, it doesn’t matter, you work asynchronously. So where and when you work doesn’t matter, as long as you can continue to be productive and have your company’s support. So I also focus on that in my teachings, you need to be honest, how far you want to push remote work, and how supportive will your company be?

Pushpak Mundre  

Right. So as you mentioned about asynchronous communication, so let’s talk about it. But I do think it’s important and like why companies should adapt to it if they haven’t, like.

Asynchronous communication

Joe  

Like I always say, I really think it’s the only sane way to try to work across challenging time zones. One of the advantages of remote work is that you can really build a truly global team that works 24 hours a day. But communication is very challenging, obviously. You know, you don’t want people to have meetings in the middle of the night and have their days and nights constantly disrupted. So with asynchronous communication, it’s more documentation based, it’s not real time. And it really helps if you have a global team. And allows greater flexibility. And when you work as I mentioned before, depending on your role. You might be a true digital nomad and you might really not have a set home address and low asynchronous communication, you can actually support that and still be successful. I’ve heard it said that office environments reward people with the loudest voice. And asynchronous communication is a great equalizer and allows everyone to gather their votes and write them intelligently. And reading and writing are really remote work superpowers. So instead of just rewarding somebody that’s very comfortable speaking with a loud voice, and lets people digest that the document asked questions in the document, they’re really gathering their thoughts intelligently and put them in the dark. For companies that are looking to become successful, they should really have a policy where everybody works as if they are remote to try to level the playing field. You don’t want second class citizens on your team people that feel like they’re remote and they’re treated differently. That’s not a good situation to be in. If you’ve ever worked as a remote member of a team where everybody else is working from an office, there’s always side conversations in the conference room. And just advantages of people working together in a room. While you’re working remotely from zoom or a conference call, it’s just a different feel. So everybody should really work as if they are remote. I think that helps to build rapport. And like I said, level the playing field. I think a lot of established companies really struggle with this, because they have people, they have teams that have worked the old way. And it was fine for years, and now that they don’t want to take it all, they don’t want to sit in an office, for example, and take video calls at their desk when they’re used to being in a conference room. So companies and people really struggle with this. And even though I am obviously an advocate of asynchronous work, there are some roles that it doesn’t, it might or might not really work for. I’ve had some salespeople, for example, tell me that they really enjoy working from an office, they like to be with their team, they enjoy the energy and the buzz of the sales team. And you don’t get that obviously working with your headphones on for the support team, for example, the support team might need a protocol for operations. If they have something urgent that is burning, putting them in a dock and waiting a few hours might not be good enough. So you might have to have protocols for escalations. And asynchronous is obviously, it is it is slow, or it’s more deliberate. But I think because of that, it really lets people, like I said before, really gather their thoughts and their questions in this document. So if you do have something where time is of the essence, then set deadlines, and open the document for comments and q&a. And I think it’s important to remember that even if you are asynchronous first, it doesn’t mean some people get tripped. I never need meetings. I never need a call. That’s not true. And I don’t think it’ll ever really be true. You need the best protocol for the situation. Sometimes you need a phone call, sometimes you need a video call, sometimes you need to meet in person. Yeah, but you can default to asynchronous first and make an adjustment as needed. But but it’s not realistic to say, oh, we’ll never have any meetings. I don’t think that’s the case.

Pushpak Mundre   

Yeah, makes sense. So what advice would you give a startup? What challenges we’re facing in getting remote cultures. And I think a lot of companies are facing this challenge.

Advice on building remote culture

Joe   

I think some startups now are growing up during the COVID era, and they’ll have remote work in their DNA, they’ll have an advantage that they don’t have any expensive real estate. They don’t have any executives that they dont have to convince to get into remote work. So I think right now, I’ve seen small startups definitely have an advantage over longer established companies, when it comes to building remote culture. It’s important to try to put expectations around communication. A brand new company with a new product might need to be in constant communication. While companies with established products, maybe you’re fixing bugs, maybe you’re adding small features might not need to have that constant communication. So you can do more of the asynchronous first stuff, as opposed to needing a lot of meetings, making sure everybody’s in sync. I would say you also want to try to hire people that you know, maybe from previous remote roles that have been successful, or maybe those with an independent entrepreneurial spirit. I’ve heard it said from a couple of companies that you want to try to hire what they call managers of one. And that’s typically going to be people that don’t need a lot of handholding and don’t need a lot of guidance. They can just come in and do the work and be independent. And as you’re building your team, you want to keep that in mind. Also, keep in mind that some engineers are not great communicators. They might struggle with sync, they might struggle with documentation. So don’t hire only for technical skills if you really need them, if you need them to do more, especially as technology leaders in your company. I have found that a lot of engineers, like I said, might not be great communicators, but they are good developers Good engineers. As you look for tech leads, though, communication becomes very important. So you want to make sure that you’re hiring not just for tech skills, but also communication. And some of the top challenges that I keep seeing out there are, as we mentioned, challenges with time zones, and executive attitudes. Sometimes leadership just doesn’t want remote work. And if that’s the case, it’s a never ending challenge for remote work to ever be successful. And if you are hiring, you’ll find that north-south hiring is easier because of the timezone. So what I mean by that is, if you’re in the US, maybe you can expand your team maybe into Canada into Central and South America, because the time zones won’t be as bad as opposed to being into the US and maybe hiring into Europe or Australia, for example, some of those some of those time zones can be pretty challenging to navigate for a new company.

Pushpak Mundre 

So I actually wanted to ask you more about the book. So I kind of missed that. Like, how many days or months did it took you to write the book? And like, how was your entire experience of writing a book? And is it your first book, you have written more books earlier also?

Joe

Um, yeah, that was my first and only book, it was really more of a brainstorm than anything. It’s a Kindle book. So it’s self published, really not that not that intense, it probably took me probably took me a couple of weeks just to get all my thoughts down and try to get them try to get them arranged. That I was, was published as a Kindle book on Amazon.

Pushpak Mundre  

Awesome. So what are your top three learnings you had by building Gold puppy and remote scorecard?

Joe  

That’s a good question. Or what I’ve learned is that even with a good product, getting your earliest customers can take some time and be pretty frustrating. I think as engineers, we spend a lot of time on the code and we assume what customers want. And we obviously want to release a good product and then you release it takes a while to get any traction and to get any traffic and it can be pretty frustrating. So I think your network of people matters more than a polished product at first. So what I think a lot of people have learned now is before publishing the product, try to build anticipation for it on social media triggers and try to get an email list, try to get some followers that are interested in when you’re building . A lot of products, once they’re ready for launch, are re-launched on a site called Product Hunt. I don’t know if you’re familiar with that. Yeah, it’s important to get friendly with someone who has a following on Product Hunt, can call and hunt your product, which is basically an endorsement of your product. And try to get people interested in it that way. Because getting your initial batch of customers can be pretty slow going. Number two, I would say I think traffic and content matter more than a perfect UI. I know some people try to get each pixel perfect. And they really worry about the UI a lot more than the content and numbers on the site. I would say number three is trying not to get caught up with any long debates on technology languages, scalability, it’s really more important to build something even if it’s wrong, try to get feedback, validate what you’ve built, and then iterate on that. If you have scalability issues, maybe that’s good news. It validates your application and validates what you’ve written. And I think you can always work on those problems. I don’t think you should spend that much time initially trying to figure out scalability before your product before your product has ever been proven as an idea. Those would be my three things.

Pushpak Mundre  

Yeah. Amazing. So what are your top three favorite books which you would recommend to like people working remotely or that like in general?

Books recommended by Joe

Joe    

The first one I would say is a book called The year without pants. And this was published way back in 2013, which somehow is eight, nine years ago now. And this book documents Automatic, who are the creators of WordPress. And these are one of the grandparents of the modern remote work movement. Again, let’s remember how long ago this was. This company was letting people work remotely long before most companies were letting you take a half day to go to the doctor, for example. So in this book, they document automatics, automatics remote first culture, which was very for the time. And since then, obviously, a lot of companies have caught on, but for the time it was very innovative. The second book, I’d say, is not really related to remote work. But it’s the Rich Dad Poor Dad series. And I don’t know if you’ve ever read any of these, but they’re interesting books that really help get your head on straight about topics like money and business taxes and entrepreneurship. That’s grown into a whole series of books that I highly recommend to anybody that is interested in trying to take more control of your finances. Let’s say number three, there’s a series called Joel on software written by Joel Spolsky. And are about 15 years old now, which is pretty old in the technology world. But some of the advice in these books is pretty timeless on software development. He doesn’t write about remote work, but he was writing about back when everybody was spending a lot of money on offices. He was talking about embracing private offices giving everybody an office with the door and a lock, more privacy, less interruptions. This was again, innovative for the time when everybody was trying to push everybody to work from one big open room that was hot for several years. And he was pushing against that, because he was a believer that for anybody doing knowledge work, you need to as he says, get in the zone. And when you interrupt somebody, it takes quite a while to get back into the zone. So he was a big advocate for letting people have private time and private space to really do a deep dive on their work. So I’m a big believer in that. And then I would say the team from Basecamp, they have a couple of really good books, rework, remote, and it doesn’t have to be crazy at work, those were three other books. And they built Basecamp as a company that was always remote. And they preach building a company that’s bootstrapped. They never took investment money. They believe in a calm workplace. And they believe you can build a nice small company by just solving your own problems and make an application out of it. Sell for a reasonable price. And you’ll build a loyal customer base and an end sustainable income. And they say that business is not war. It doesn’t have to be that competitive. Everybody can eat. There’s room for everybody. And you don’t need growth at all costs. So they believe in building a calm, profitable company that doesn’t owe anything to anyone. And I think that’s a really solid approach.

Pushpak Mundre 

Yeah, this makes sense. I think this book seems like there’s so much to learn . Any folks in the remote work that you admire for their contribution to making remote work better for the world.

folks recommended by Joe

Joe  

And yeah, there are a couple of names out there. Chris Hurd. I don’t know if you follow him on Twitter or LinkedIn, but he’s a CEO of a company called first base. And he’s single minded in focus and very, very persistent in his messaging on remote work advocacy. Yeah, I think he’s been pushing the remote work message, probably stronger than anybody for the last two years. And he’s been pretty successful with it in the case of write ups and a couple of major publications as well. So I’d like to give a nod to him. Second would be Darrin Murph, I believe he’s the head of remote. He’s from GitLab. And he’s somebody else that always seems to be everywhere at once you always see his name and in articles and publications and GitLab is one of these companies that they recently became a public company, which means that you can buy stock in them. And I think they are the largest all remote public company out there. And they’re one of these companies that really preaches about asynchronous communication and everything should be documented. And they have a lot of public documentation on their site. And there you can always find Darrin Murph writing about their remote work culture, and they’re pretty interesting to follow. And then just want to give a nod again, to the leadership team, at Basecamp. Their books have been pretty, pretty eye opening on how to build a great remote culture. But not just remote culture, how to run a business that’s calm and sane. And I know Jason Freed has posted a couple of times, he’s posted a screenshot of his calendar. And I know a lot of executives and even non executives at work, a calendar that is just overflowing with meeting after meeting . He shows a screenshot of his calendar, and maybe he has one meeting a week. So this is a very successful company. And I really admire what they’ve built and what they’ve tried to teach the rest of us.

Pushpak Mundre

That’s nice. Like, oh, yeah, it might take a lot of effort to do that, like, as a leader and having one meeting a week that is, maybe work differs from company to company was maybe they have built this kind of things. Yeah. So what are you into outside of your work? What do you do when you’re not working?

Joe 

Oh,  I am into investing. I like to play the stock market, I’m into real estate investing. I can speak for a while about investing in stock options, calls and puts. I’m self taught and self taught in some years, obviously are better than others. But I find investing very interesting. I think people in the older generations were probably taught to save their money. And now I think what we’ve grown over the years is don’t save it because of inflation invested in building assets. And you know, I’ve been experimenting with that. I mean barbecue and grilling meat. That’s very interesting to me. To dogs, I love my dogs. I have three dogs right now. I also played the drums.

Pushpak Mundre    

Awesome. So thank you so much, Joe, it was really great talking to you. And I think we got a lot of insights about remote culture. Building remote teams are also about building remote projects and the recommended books that are recommended and the people that recommended like, they are like I think really important as they are also giving amazing insights and people should really follow them as well. And I think we can reach out to you on Twitter, right? Like our audience.

Joe 

Or you can find me on Twitter. My handle is Chief remote. You can find me on LinkedIn under Joe Giglio from North Carolina. And if you want an easy link to all my projects, you can find that on Chief remote officer.com. And there’s also a web form on there if you just wanted to send me an email. And I’m always looking to meet and collaborate with quality people so please reach out if you’d like to work on any project.

Pushpak Mundre  

Thank you so much. Thank you