SimpleLeadership Podcast

What are the challenges that accompany being a woman leader in technology? How can you be an ally for women in your workplace? How do you overcome imposter syndrome? These are just a few of the questions Christine Awad—the Director of Engineering at Facebook—so kindly answers in this episode of Simple Leadership.

How do you build an engineering team of A-players? What does a well-rounded high-performing team look like? Why is engineering for impact more important than solving hard problems? In a world where engineers are looking to pad their resume and solve cutting-edge problems, Ashish Aggarwal shares the one thing that is far more important: solving your customer’s problems. In this episode of Simple Leadership, he walks through building high-performing teams, solving customer problems, and the best way to maintain technical excellence. Do not miss this one. Ashish Aggarwal is the Co-Founder and CTO of enterprise SaaS management platform, Productiv. Prior to founding Productiv, Ashish was the VP of Engineering at Postmates, where he built and led a team of over 130 engineers to develop all technology for the food delivery marketplace. Before Postmates, Ashish led product and engineering teams at Amazon, where he helped build and launch Amazon’s own Freight Transportation Network in North America, Europe, India, and China. Ashish has also held senior leadership roles at eBay, where he built the e-commerce platform’s checkout experience, and at Microsoft, where he built the enterprise conferencing solution, Skype for Business. Ashish holds a Bachelors in Computer Science from the Indian Institute of Technology, Delhi. Outline of This Episode What Ashish has learned from years in management Ashish notes that he made the typical mistake of not letting go. He struggled to trust that his team could take control. He admits that he needed to let go of the notion that he was the smartest person in the room. Once he realized that he needed to let things go, he stopped reviewing every document from the last line of the design to every line of code. What led to his change of heart? One of his coaches told him, “You know, your team can run much, much faster than this and we understand you're new, but let go. We understand it's hard, but try it. See what your team does when you just let them be. Give them the problem and let them come with the solution. They might just surprise you.” Ashish notes that it was eye-opening. He can now say, "Hey, I will let my team solve this problem—even though I have good ideas about it—I can give input, but let me give up control." What does a well-rounded high-performing team look like? Ashish states that the obvious thing that you must look for is competence and skill. You can't have a high performing team without core capabilities. But beyond that, you need a team that is passionate. You want to build a team of self-motivated players who see a problem that needs to be solved and will solve it. Ashish emphasizes that taking ownership is a culmination of all of this. He wants engineers that are constantly asking, “What is the next big problem I can solve?” Ashish doesn’t assign problems to his team members. Instead, he points them in a certain direction and they identify the problem. They identify the solution. They know what success looks like, and they are diving in to get that done. When an entire team is the problem identifier and the problem solver, you naturally start thinking more long-term. High performing teams take ownership of solving the customer’s problem and do. Ashish has seen teams where the culture of collaboration is not there. Competition is there. Cutthroat culture is there. So the question must be asked—is the management defining the vision? Are they letting their team members solve the problem? Find what is broken by talking to the team. Solve high-impact problems—not hard problems Ashish emphasizes that high-performing teams don't work on the hardest problems. High-performing teams work on the most impactful problems. High-performing teams take ownership of the customer's problem. The solution may be pretty low tech. Maybe the solution doesn't add to their resume. That doesn’t matter if the impact on the customer is there. High-performing doesn't mean that their performance...

Jon Thornton worked at some small companies in NYC before he ended up at Squarespace. He’s been able to build a new product and new team—their email marketing product. He launched that and has since been supporting other products. Throughout his career, he’s learned how to manage technical debt. What is the difference between technical debt and good technical debt? What is a framework for using technical debt? Listen to this episode of Simple Leadership for Jon’s advice on managing technical debt. Jon has been solving problems with software for over 20 years and leading engineering teams for 10. Along the way, he's parked millions of cars, improved textbooks with AI, reduced the price of prescription medication, and sent billions of emails. Currently, he's an engineering director at Squarespace in New York City. Though Jon's day job is mostly meetings and documents, he still gets his coding kicks in by maintaining a mildly popular jQuery plugin in his free time. Outline of This Episode How technical debt compares to financial debt The common definition of technical debt is that it’s code that you don’t like and you’ll need to fix or change later. But Jon applies a more narrow definition: It’s work that he expects to have to do in the future. It’s not necessarily code that he doesn’t like. Jon points out that financial debt is a commonly accepted occurrence. Someone that takes out a mortgage to buy a house and is congratulated. It’s a “responsible” use of debt. You can use technical debt to get value now and then you can pay it down over time. It’s a tool. It allows you to reorder when they value and the payment happens—you just have to use it responsibly. People want to have perfect code from the moment of conception, but it isn’t always worthwhile from an ROI standpoint. If it doesn’t make more money or provide more value, it can be shelved for later. How to manage technical debt When you think about starting a new engineering project, it starts with estimates: “How much is this project going to cost us?” It typically refers to man-hours or engineering week. The cost of the project is how long the team will spend building it. If you’re following the financial debt analogy, you are taking out a tech debt mortgage. You’re borrowing time that will be paid back later. You’re doing it in a way that creates more value now. The main reason engineers exist is to provide value—to shareholders, your company, and the users of your product. If a manager takes over a team from another company, they’re immediately taking on technical debt or risk that has accumulated. How do you walk through that? How do you evaluate that? According to Jon, you can talk to people or read commit history to understand how you ended up with the system you have. The next step is to assess the kind of technical debt you’re dealing with. What technical debt is actively accruing interest? Are you spending time on it with bug fixes? Is it growing larger? There may be an API with design issues. If you keep building on top of it, it will be harder to evolve later. Other kinds of debt may be a scaling issue where performance is okay now, but your database can’t support it later. You have more time to put that technical debt aside and address it later. Assess and establish urgency. Good technical debt is intentional During his initial Squarespace project, Jon used an access control list where only certain people had access to certain features. The right way to build it is to have a database table and management UI that makes it easy to add people. But the list didn’t change frequently. It would be easier to have a hard-coded list of IDs in their code-base. To give someone access, they’d make a new commit and deploy it. It was fine for the first two years of the project. They’d instead spend their time on things that immediately impacted the project they were working on. They could go in and make the list more dynamic down the road. Jon recommends that...

Being in a management position in any industry can often leave you overwhelmed. Striking a balance between your work and personal life is already difficult. So how does a manager take parental leave? Matt Newkirk—the engineering lead for Etsy’s International Customer Experience initiative—has worked out some of the kinks. I’m the father of three girls. During their birth, I was fully involved in startups and was never able to take parental leave. Not only did I miss out, but as a manager I feel I can’t help my team plan a successful leave because I never experienced it. So in this episode of Simple Leadership, Matt shares how to plan and prepare for parental leave. Anyone in leadership can benefit from his experiences. Outline of This Episode How can a manager take parental leave? Matt has two children, a 4-year-old son and a 2-year-old girl. He started at Etsy when his son was 7 weeks old. He was fortunate to receive some parental leave, but there was an odd tension. He was just forming relationships with his team and it felt strange to disappear. So he took that leave very sporadically, almost as if he was taking vacations here and there. Most of the decisions were made before or after that. Very little true delegation had to happen. But when his daughter was born, he wanted to take his full leave. He’s very fortunate that Etsy provides 6 months of parental leave. It was a great opportunity to reconnect with his family and disengage from work. When anyone in leadership takes time off, its news. But it is possible. You want to role model that it’s okay to take parental leave. It shouldn’t just be a benefit on paper that no one uses. How can taking parental leave empower your employees? Listen to hear Matt’s take. You HAVE to plan your leave When possible, you have to build out a plan for your parental leave. Matt was managing many different teams with different scenarios. He notes that sometimes it’s as easy as delegating one person to carry out a task. But it needs to be clear to stakeholders and delegates who is taking on what responsibility. It took him 2–3 months to iron out the details for his leave. He recommends to try and have this done at least one month before you take leave—in case your baby comes early. When should you start planning? Around the time you’re comfortable telling your boss. These plans don’t expire. So if you wrap up a project earlier than you thought, it’s great. Before you leave, Matt says “I think your job before that happens is to make sure that your reports trust you enough, that they don't have to wonder what's going to happen.” You don’t have to think about missing out on opportunities or ask: “Am I going to lose my job? Am I going to get reassigned? Am I going to get the side-eye for the next six months?” Your job is to make sure that none of those things happen. You need to have a reintegration plan A reintegration plan is just as important as planning your leave. In Matt’s case, he knew he was coming back to a reorganization and a new boss. He wasn’t sure how the units would fit together. So the first thing he did was contact his new boss and let him know when he was coming back. Then he thought about how he’d spend his time. He took some strategies from the book “The First 90 Days” and planned to spend the first 30 days figuring stuff out, listening to his team, and understanding perceived problems. Then he spent the next 30 days building hypotheses, testing them with new data, etc. In the last 30 days, you begin to act on that research. He emphasizes that it all comes down to communicating effectively. Matt also talks about how the transition back isn’t always smooth and shares how he adjusted to his role in a very changed company. How a manager should support their team’s parental leave Matt notes when someone tells you they’re going out on leave, your one job is to make them feel at ease. Let them know you’re there to support them. Then figure out when they’re going to...

If you’re an engineer in a leadership role where you’re dealt with the task of developing teams, the hiring process can be daunting. Do you hire junior engineers that you can shape and mold? Or senior engineers who are experienced, but come with baggage? And how do you throw boot camp graduates into the mix? Johnny Ray Austin joins me to lend his thoughts on the hiring process, including what he looks for in an engineer. Don’t miss it! Johnny is an experienced engineering executive and international public speaker. Johnny claims he got into leadership by sheer luck—but he ended up taking the leadership position and never looked back. He’s now the VP of engineering and CTO at Till, a company that helps people pay, stay, and thrive in their homes. Outline of This Episode “The Death of the Full Stack Developer” Johnny’s talk, “The Death of the Full Stack Developer”, was a culmination of what he's seen developing in the industry. He’s seen an evolution of people switching engineering midway through other careers. The people who are switching have a more difficult time because of the expectations that are placed on engineers to know it all. Catching up to everything that’s happened struck Johnny as silly. He can’t keep up with all of the new stuff out there. It also depends on our definition of “the stack” (It’s typically short-hand for front-end and back-end experience). 80% of people land on their website from a mobile device—but no one talks about mobile devices when they talk about the stack. The full stack encompasses a lot more than what we mean when we use the phrase. When you look at it that way, it’s unreasonable to expect someone to be an expert in the entire stack. The true full stack developer is dead and gone. Johnny is quick to point out that that doesn’t mean you can’t be good in multiple areas. But you have to recognize that there are specialties. While you do want as much bang for your buck as possible when hiring, you can't burn people out. You have to set expectations accordingly. How do engineering leaders stay on top of new technology? Keep listening to hear our discussion. Hire engineers for their strengths—not lack of weaknesses Johnny points out that—as an industry—we assume that one hiring process is going to work for every company out there. But it’s up to you to find a process that works for you and your team. You have to take into account questions like: Can they grow into what I might need in a year? Or 18 months? Does your company align with their future goals? The paradox is that you need to stop hiring for the now—and hire for tomorrow—while still solving today’s problems. John screens a potential team member’s ability and willingness to grow with the company from the first phone call. He talks about their ambitions as a business and asks if the potential engineer can see themselves growing with that vision. Are they interested in leadership? Are they willing to mentor other engineers? What is their mindset regarding operational excellence? He’s honest about his expectations moving forward. Hiring engineers is a risky endeavor. Bringing on the wrong person can damage the team. Johnny emphasizes that you should hire engineers based on their strengths. Then, you can hire other engineers to fill in the gaps. They can learn from each other while complementing each other. Where are they really strong? What are their interests? Some people are good at cranking things out. Some people are great at communications. You want your engineers to work on the things that allow them to thrive. You need to build teams that are diverse because together you have something greater. Junior engineer, senior engineer, or boot camp grad: which is better? Johnny points out that if you hire a senior engineer, you reap the benefit of their experience and track record. So there’s less training involved—but they often come with baggage. They’ve done things a certain way their entire career and tend to be resistant...

Today’s guest—Emad Georgy—is passionate about technology leadership. He’s a CTO Consultant and the Founder and CTO of Georgy Technology Leadership. Emad has been in the tech industry for over 25 years. His hybrid approach to technology management—focusing on both the practical and cultural elements of leadership—makes Emad a trusted and valued partner helping both domestic startups and global enterprises scale and grow. In this episode of Simple Leadership, we chat about what cultivating leaders looks like. Sometimes, it involves making difficult decisions for your team. You must also embrace your values and lead your team by example. Listen to learn some steps to help you grow and mature as an individual and as a leader. Outline of This Episode [1:24] Emad Georgy joins me in this episode[3:23] Making difficult decisions for your team[6:01] Tips for leaders starting a management position[7:49] What is the concept of leadership debt?[10:38] Traits it’s important for technology leaders to possess[14:40] Embrace the engineering mindset[18:38] Develop a deliberate “people strategy”[22:33] Embrace problems as a tech leader and CTO[25:13] How to improve your team’s customer focus[29:31] How to become a process ninja[32:56] The importance of resilience in engineering leaders[35:26] Leading through times of crisis What is the concept of leadership debt? According to Emad, if tech leaders really want to solve the root cause of technical debt, they have to start talking about leadership debt. It’s the concept that the decisions you make as a leader results in hidden costs that build over time. He points out that “It's our responsibility as technologists to bring [those decisions] to the surface, make [them] transparent, hold them and go, "Are we making decisions that enable the durability of the company and/or architecture?". You don’t wake up one morning and decide to rewrite your whole platform or application—the decision is based on little decisions and mistakes that occur over time. Having knowledge of how leadership debt works helps you make better decisions along the way. Technology leadership development begins with these traits Emad points out a key trait: embracing the concept of ownership. A leader “Must have a collective sense of responsibility—not just about his or her actions—but about the actions of their team and the organization”. It’s about leading by example. You need to be problem-solvers, not problem-reporters. Emad has learned that pointing fingers only serves to create dissension among your team. It isn’t about who’s at fault, it’s about how you got there. So when something goes wrong, you step up and take ownership—then help your team find and fix the problem. Emad points out that as the leader, you get to manage the company culture. He defines culture as “the stories you tell every day”. If you spend every day complaining and moaning about the work you’re doing—that’s your culture. That is your contribution to the culture. But you can easily change that. Keep listening as Emad shares some other traits and processes he believes are key to your success. Technology leaders need a deliberate people strategy Emad gets frustrated when leaders claim that they’re “all about their people”, but when it comes down to it they focus less than 20% of their time on their team. He believes it is essential to apply a tangible growth path to your team. Where do you want to see the team go in a year? What will you do for the company in that time? What do you expect from each individual? Are you helping them determine their career path and managing their growth? Anywhere Emad has migrated in his career, he embraces a people-first approach. He’ll spend his first couple weeks—or month, if necessary—having one-on-ones with his team members. Getting to know your team speaks volumes about who you are as a leader. You need to take the time to show them that you actually care and hear their needs and concerns. Emad points out...

Transitioning an engineering leadership position to a work-from-home model can be a challenge. For some engineers, working remotely is the norm. For others, such as those working for Shopify, being forced to work from home because of the Coronavirus is a whole new ballgame. In this episode of Simple Leadership, Farhan Thawar joins me to chat about his transition into working from home and how Shopify has made the process manageable. We talk about the benefits of coding in pairs, whether or not managers should still code, and what he looks for when hiring engineering leaders. Farhan became the VP of Engineering at Shopify after the company acquired Helpful.com, where he was co-founder and CTO. He is an avid writer and speaker and was named one of Toronto's 25 most powerful people. Farhan has held senior technical positions at Achievers, Microsoft, Celestica, and Trilogy. Farhan completed his MBA in Financial Engineering at Rotman and Computer Science/EE at Waterloo. Listen to this episode for a glimpse into his expertise. Outline of This Episode How Farhan has been impacted by COVID-19 Shopify sent all of their employees home to work remotely at the beginning of the COVID-19 outbreak. They also supplied each employee $1,000 to make the transition a smooth process—for necessary equipment such as webcams, ergonomic chairs or mats, and office supplies. They knew they wanted to be proactive in protecting their team and those around them. Farhan much prefers in-person communication and interaction. Since working from home, he has made a concerted effort to focus on communication that includes Google Hangouts, Zoom calls, audio, and asynchronous video—all before defaulting to text. His goal is to connect and converse with fellow employees about their lives and remember to have non-work-related conversations like they would if they were in the office. How to take your management to the next level Something new managers often struggle with is whether or not they continue to code once they assume a leadership role. Should they work on company projects? Practice coding on the weekend? Farhan incorporates coding into his schedule every Thursday morning as a way to “go deeper” and stay on top of his skills. Something that Shopify implements is what is called a “studio week” in which executive-level team members take a week to deep-dive into their craft to continue learning and perfect their skills. It takes their skillset to the next level, gives more context to how their team operates and helps them stay on top of the right questions to be asking their team. How pair programming can make a positive impact Pairing with someone is a great way to learn a new environment and language. It’s also a great way to learn something new that you’re not as familiar with. You can lend your technical expertise and architectural ideas to the team. You work to help each other stay focused and intense—and add to the intellect and velocity of the team. Shopify allows their teams to set up pair programming hours—they simply open space in their schedules for others to sign up. They even supply special rooms specifically for the practice. Farhan shares that it’s set up with two monitors, two keyboards, with a long desk so you can sit and pair for a long period. Others prefer to work on pair programming in the comfort of their own pods (work areas). While Shopify employees are practicing social distancing and following COVID-19 “shelter at home” protocols, they use a nifty tool called Tuple, a remote pair programming app. Listen to the whole episode as Farhan explains the importance of this practice. How to hire engineering leaders Farhan doesn’t believe your typical interview style is particularly effective in choosing the right engineering leader. They like to find a way to immerse the potential hire into a situation they’d likely be solving and observe how they’d behave. It’s far more effective than asking questions. However, they do implement...

If you’re in a leadership position in the engineering industry and have suddenly been thrust into working remotely, it may feel like your world has been turned upside down. In this episode of Simple Leadership, Dana Lawson and I discuss a few tips to help you manage remote teams. You want your team to thrive and be successful during a time of great uncertainty. Dana describes herself as an atypical engineer. She wanted to attend college to be an artist but soon realized the ‘starving artist’ lifestyle wasn’t going to cut it. She took the ASVAB test when she joined the military and scored high in engineering categories. In the last 20 years, she’s worked in every tech position possible—most recently, she is the VP of Engineering at GitHub. Listen to hear her unique story! Outline of This Episode You have to embrace a leadership mindset Dana states that “Anybody can be a leader, it’s just how much you wanna unlock it”. She believes it’s an attribute that’s been ingrained in her personality. She’s naturally an A-Type and has never been afraid to speak her mind. In whatever capacity she was working in, she always took the initiative to move the ball forward. You don’t have to have a management title to be a leader. She just believes that some of us gravitate towards being a leader more than others—but that we all have the calling to lead in some way. Dana argues, “Anybody has the ability to go influence change and bring up the people around them to do great things”. Tips and strategies to manage remote teams Dana shared some tips she’s learned from a managerial role: Write it down.Form a daily structure foryour teamandyourselfTake advantage of ALL the communication tools available to youInvest in some camera gear: To keep things light-hearted—though partially serious—Dana points out that you have be on-point with your emoji game. There’s verbal communication, non-verbal, and emoji verbal. Humans have reverted to Egyptian Hieroglyphs. Oddly enough, each company has its own set of social norms with emojis—so learn quickly. These aren’t just transactional relationships Don’t forget there are humans on the other side of your communication. How would you interact with someone in the office? What about pleasantries like “Hey, good morning!” or “How are you today?”. Dana points out you can ask about your team’s families, learn about their dog, and keep apprised of their life like you would in the office. A distributed workforce still needs to feel like they’re part of the office family. Dana points out that you want to build empathy even when you won't have the physical contact that you would in an office setting. Especially now, with many people working from home due to the Coronavirus, people are anxious. They’re worried about their jobs and their livelihood. As a manager, you’ll have to learn how to empathize with them and how to quell their fears. You’ll likely have to help them focus on the projects at-hand and iterate that you are in this together. Above all, Dana recommends being realistic about your deadlines. Transitioning into working remotely won’t be 100% smooth and you have to have grace through the process. How to onboard a new hire 100% remotely Dana believes the easiest way to onboard remotely is to be completely intentional with everything you do. Schedule every onboarding task and learning opportunity into their calendar Direct them to all of the tools and processes they’ll need. Email them with links to training documents, with a schedule of when to go through them. Dana points out this is a great time to record training videos. It helps break up written policies and gives new hires a face and voice to connect to. Communication is key during the onboarding process and needs to be even more emphasized with a remote workforce. You can’t just tell them, “Connect with me if you have questions” or “Tell me if you have a problem”. As the manager, it is your job to consistently check-in, ask how they’re...

A management role in software development can be difficult to navigate. You need to keep a high-level perspective on projects while making sure they go smoothly. Eric Elliott, today’s guest on the show, believes that you need to implement coding quality practices such as test-driven development. In this episode, we talk about why software development processes such test-driven development makes an impact and why it’s important to remove bugs. We’ll also talk about how to train developers and keep them happy—and why it’s inherently important not to rush the process. Eric Elliott has been in software development for the better part of his life. He co-founded EricElliottJS.com and DevAnywhere.io, which aim to teach developers essential software development skills. He is also the author of the books, “Composing Software” and “Programming JavaScript Applications” He builds and advises development teams for crypto projects, and has contributed to software experiences for Adobe Systems, Zumba Fitness, The Wall Street Journal, ESPN, BBC, and top recording artists including Usher, Frank Ocean, Metallica, and many more. Outline of This Episode What are the tangible benefits to reducing bugs? If you are able to reduce bugs on the front end, you spend less time fighting fires. According to Eric, “Fixing bugs is not work that’s delivering direct value to your customers—it’s rework”. Customers don’t look at your software and think being “bug-free” is a benefit. They just assume that it’s a given that there will be no bugs. Secondly, Eric points out that you will lose customers if you produce buggy software. Struggling client retention and turnover means you’ll have to increase your marketing budget in order to attract new business. It is the most expensive and time consuming part of producing software. But it is imperative to deliver a stellar product on the front end. Because, per Eric, “Every hour spent in code review saves 33 hours of maintenance”. The hardest part is understanding that this process takes time and cannot be rushed, but it is well worth it in the end. What happens when you try to rush your engineers? Those in leadership positions often have to deal with pressure from higher-ups to rush a project or push a timeline. This is the worst thing that could happen, and you’ll start to see significant negative results of rushing your developers. Eric points out that bugs will pile up, testing will get skipped, and communication will suffer. Your team will feel like they don’t have adequate time to mentor each other, and knowledge sharing is left behind. Productivity levels will plummet. Even worse, your developers can reach the point of burnout—with effects that can be long-lasting. The Japanese struggle with a culture of over-working to the point that they have a coined term for people who die because of overworking—”Karoshi”. While this is an extreme example, it’s something you want to steer clear of. Pushing your team to rush will bring to fruition the opposite of what you intend. What is your role as a manager/leader? Eric uses a manufacturing analogy to drive this point home: “ There's a floor manager who is usually perched up high above a factory floor so they can see everything happening on the factory floor. They can see where things are piling up. So on an assembly line work comes in one end of a line and goes out the other end of the line, but then all these different processes thrown in the middle that take different amounts of time to complete. Optimizing that process is the job of the floor manager”. The moment a manager steps in and gets themselves involved in the work they lose perspective of the overall process. No one is doing quality control. The assembly line will start to have pile-ups with no one able to step in and smooth the process. It’s a manager’s role to ensure the process is slow and smooth, but efficient. The key is proper communication—If you show your superiors that progress is being...

If you are transitioning into an executive or leadership role in an organization, you can find yourself dealing with incredible loneliness. You also deal with a change in power dynamics, gaps in information, and a lack of support systems. It is difficult to prepare for the change from “getting work done” to being an “influencer”. As a former COO, today’s guest, Suzan Bond, understands the struggle of the transition. She joins me today to share some ways you can combat loneliness and ease the transition. ​​Suzan is an executive coach and organizational strategist who has spent over a decade in technology. She's a regular contributor to Fast Company where she writes for the Work-Life section—covering leadership, personal effectiveness, and productivity. She has an educational background in psychology, organizational behavior, and community organizing. She received her coach certification from the Coaches Training Institute. Outline of This Episode The difficulty of a transition into leadership Suzan points out that many managers and leaders aren’t prepared for the transition into an executive role. They go from deriving their value from the work they’re able to complete and suddenly have no direct impact. Instead, they must learn how to influence others, essentially working through other people. This process can lead to a struggle, a feeling of a loss of control or perceived power as they’re pushed outside of their comfort zone. Suzan believes that you must acknowledge that you are making a significant transition—and you cannot underestimate the mindset shift you must make. On a basic level, you may be gaining autonomy or a pay raise. But you’ll also likely deal with long hours and significant demands on your time. You will be changing how you operate on many levels and must be mentally prepared. ‘Gaps in Information’ and the connection to loneliness Our culture has made a large shift towards being transparent and open about everything from how money is spent to sharing how much executives in a company make. But finding the right balance of transparency is a delicate balance—and often keeps leaders up at night. They question themselves: “Am I being open enough? Am I giving enough context”? On a more complex level, they may desire transparency but be unable to give it due to legal issues or simply protecting employee privacy. Leaders are often criticized and misunderstood because they cannot share all of the reasons behind the changes they implement. It leads to a feeling of awkwardness as a leader. People think you’re incompetent or label you as uncaring—and you simply can’t defend yourself. Whatever the reason, there are times you can’t share all of the information you have. All of this can exacerbate the loneliness you feel. To overcome this dichotomy, you must rely heavily on building a foundation of trust with your team. The interplay between trust, vulnerability, and confidence As a leader, you have to actively work to build trust so when there are times you have to fall back on “trust me”—they do. It must be prioritized above “proving yourself” and implementing new strategies. Suzan recommends spending time doing a “listening tour”—actively engaging with people in your company to gather information and gain insight—and lend a listening ear. It helps you build a foundation of trust and learn how to connect within your organization. With the high demand for openness and vulnerability, you must learn to find a middle ground. We are expected to be vulnerable while still projecting confidence, which is a delicate balance. Suzan and I agree that showing your humanity goes a long way—you don’t have to pretend to be superhuman when you’re not. She shares some simple ways you can project vulnerability in conversations, so be sure to listen. How do you combat loneliness in leadership? Suzan shares some tips she believes will help ease the transition and combat the loneliness of the new role: 1. Establish a morning...

Effectively leading a team through an acquisition or merger can be shaky ground to navigate. You aren’t just dealing with merging teams, tech stack, and processes—but also a culture. Your team needs leadership that is open, honest, and transparent about the process. If your company is going through a merger or acquisition and you want to arm yourself with some tools to manage your team efficiently through the process, learn from the expertise of today’s guest, Loïc Houssier. In this episode of Simple Leadership, Loïc and I discuss what he’s learned about leadership, what his mistakes have taught him, and how he managed his team through multiple mergers. With a background in Mathematics and Cryptography, Loic launched his career as a security researcher in France. As his career evolved, he took on management roles in Software Engineering—focusing on Critical Infrastructure of European Administrations—for Orange, Thales, and Naval Group. He joined a startup, OpenTrust, to help with its growth and organize the teams and eventually became the CTO. Loïc joined DocuSign via the acquisition of OpenTrust 4 years ago and is now the VP of Engineering and based in San Francisco. His role is leading the Docusign effort on Mobile, eCommerce and Billing systems. Outline of This Episode Operating in different industries help you become a better leader With Loïc’s background as a research engineer in the field of security, he was used to being the voice of expertise in a room. As he moved through different organizations and moved into managerial roles, he worked in areas where he was not the technical expert. It was an eye-opening experience for him. Loïc had to learn to put his ego aside and find other ways to get his teams to listen to him. PerLoïc, “You don’t have to be the best technical person in the room to make a decision”. Armed with the knowledge that he wasn’t always going to be the expert, he sought to find ways to learn to listen to his team. Even without the technical knowledge, he could help solve their problems and make decisions. Loïc encourages you to try something completely different than your area of expertise for the humbling experience—and learning lessons—you’ll get. The higher up you move the more you have to rely on your non-technical skills to influence, communicate and get things done. Mistakes can be a catalyst for growth When you take on a management role you quickly learn that everyone is gifted differently. Some people, like Loïc, are more outspoken and on-task go-getters. Other people can be quiet and painstakingly detail-oriented. Loïc experienced this firsthand with a team he was assigned to for a government project. He assigned a team-member a task that he expected to take a couple of days. But it took almost 4 weeks for him to submit the requested document—after being asked for it multiple times. Loïc went to his superior, fuming, stating there’s no way he could continue to work with someone who wasted his time. After explaining the situation to his boss, his manager flat-out told him that the mistake was his. He had assigned the wrong task to the wrong person. Loïc learned that as a manager, his role was “Not to change people, but to understand how people are efficient in their own way and give them the work where they will be successful.'' The team member that he struggled to understand? Loïc placed him in a role that was a much better fit—managing configuration management. He excelled in the role and did amazingly well. Loïc learned you can’t be quick to judge people who are different. Instead, you must take a step back and approach the situation through a different lens. You may yield unexpected results. What Loïc learned about managing people through a merger When a company is acquired and your team is about to be integrated into a new culture, it can be disruptive. If you’re in a leadership role, it can be difficult to navigate the changes while keeping your team calm and collected. Loïc...

Cultivating diversity in the workplace is at the forefront of challenges that starts-ups face. Creating diversity in race, ethnicity, gender, and even opinions and skill sets is something every business must implement. You need to build a team with diverse perspectives in different backgrounds. Tess Hatch from Bessemer Venture Partners and Jess Mink with Auth0 lend me their expertise in today’s episode of Simple Leadership. We’ll cover everything from hiring the right people, what investors wished managers knew more of, and being an ally and sponsor. Tess Hatch earned a bachelor’s degree in aerospace engineering from the University of Michigan. She went on to earn a master’s degree in aeronautics and astronautics engineering from Stanford. She started her career as the head of product and mission management at SpaceX. She is now a venture capitalist specializing in frontier tech and serves on the board for many businesses in the industry. Jess Mink holds a bachelor’s degree in computer science from Carnegie Mellon University. She’s worked at Amazon as a software development engineer and has worked with various startups over the last 26 years. She is now the Sr. Direction of Engineering at Auth0. Her goal is to help build teams who empower their employees and solve real-world problems. Outline of This Episode Creating company culture begins with hiring the right people When you’re looking at forming a company you need to be mindful of hiring people around you to complement your skillset. If you’re the ‘tech person’—hire someone who is business-minded. Your goal is to build a team that has deep expertise and understanding of the market. Of course, how you fill out your team depends on the industry you’re in. You are cultivating the right—or wrong—culture with every person you hire. Every single person you add to the mix needs to be carefully selected. You need to balance technological expertise with communication skills and emotional development. It’s important to define and create guidelines for your company culture from day one. This provides you a clear definition of the type of people who will fit and enhance your culture. Keep listening as we discuss issues startups need to address, scaling your business, learning what your customers want, and managing engineers. Create a professional board of advisors—for yourself Are you ready to be a better manager and leader? As a leader in your organization or industry striving to build healthy teams, you also need to take advantage of mentorship and learning opportunities. Work with a high-level executive coach. Be a part of a CEO group. It’s a difficult and lonely job, and these groups know the issues you face. You can help each other through challenging team dynamics amongst other problems to solve. Tess recommends building a personal team of advisors—specific people you reach out to for guidance in specific areas. Find 3-6 people you look up to as mentors in the industry (maybe even past professors, previous employers, etc.) and specifically ask them to be a mentor for you. Build yourself a network that you can lean on as you continue to learn about your industry and the struggles you face. Jess gives a sage piece of advice—know the struggle you may face before entering a particular position. Go to slack channels or online forums about the problems people in management face and what their solutions are. As you begin your management position, you’re already aware of some of the challenges you’ll face—and equipped to deal with them. Cultivating diversity in the workplace Not only do you need to balance different perspectives and skill sets in your senior leadership slots, but you need to build a diverse workplace. You will destroy your company if you call up your friends and build a team with similar interests and mindsets. You must be sure to encourage different voices to speak up. Make inclusion and diversity a metric that you track. Jess and Tess agree that the...

Being an effective leader is about more than just managing people efficiently. Krister Ungerböck (unger-bahk) joins us today to talk about why being a leader is about changing the language you use. Krister is a keynote speaker, CEO Coach, and global expert in The Language of Leadership. Prior to retiring at age 42, Krister was the award-winning CEO of one of the largest family-owned software companies in the world. His expertise in the Language of Leadership is based upon his unique experience as a global CEO leading teams in three languages while observing and doing business with executives in over 40 countries, building businesses in six and living in three. As a corporate keynote speaker, Krister is passionate about sharing the secrets that his team used to win 5 consecutive Top Workplace awards and achieve remarkable employee engagement levels of 99.3%. His upcoming book, The Language of Leadership: Words to Transform How We Lead, Live and Love, will launch on Bosses Day, Oct. 16 Outline of This Episode The language of an effective leader Are you in a leadership position, but often find yourself floundering, unsure of your role? Do people find you domineering or hard to work for? Krister sought to write a book to help you develop and embody a leadership style that isn’t only effective in the workplace, but in your personal relationships as well. A crucial element of effective leadership is the language you use. Krister shares a story on this episode about a woman who stayed loyal to her company—despite the fact they forgot to pay her multiple times. Would your best employee stay if you were unable to pay them? Does your leadership elicit that kind of loyalty? You’ll want to listen as Krister and I discuss the language of requests and why it’s important to be a leader, not a manager. Why the ‘language of expertise’ doesn’t work Why do you think most people get promoted? It is usually because they have proven their expertise in whatever field they’re working in. They’re simply good at what they do. But does being an expert qualify you to be a good leader? Obviously, it’s a great quality to have, but Krister talks about why you do not want to lead from a place of expertise. It puts you in a position where you are constantly required to give people answers. When you find yourself leading anywhere from 10-30 people, this is no longer a feasible option. There is not enough time in your day to constantly answer questions. Instead of giving answers, you want to equip your staff to be able to answer some of the tough questions and come to their own conclusions. Your goal as a leader is to attract and retain great people and build a company full of top-performers. You definitely want to listen to the full episode—Krister and I cover the key to employee engagement—you don’t want to miss it! The importance of asking better questions Effective leadership requires the ability to ask better questions to get better responses. One way Krister puts this into practice is asking permission to give someone feedback. He does this for a couple of reasons. Firstly, it gives the person the opportunity to be honest and state they’re not in the right headspace. Secondly, you want them to be engaged, interacting with you, and be moving towards a solution. One of Krister’s favorite ways to phrase a question is “On a scale of 1-10 how open are you for feedback?” Or, “What do you think are the top 5 things you need to work on?” You need to ask a question to engage your employee that doesn’t elicit a simple yes or no answer. When someone answers with a number, it gives you the opportunity to follow up with “What can we do to make that seven a nine?” It’s a great tool for better engagement and communication. Emotional Intelligence: Leading from a place of empathy I think many leaders struggle with the idea of emotional intelligence and leading from a place of vulnerability. But think about it—you are more connected to people when you...

What does it take to up your game and improve your management skills? Do you need to read better books or get around the right environment? Here to help us dig in and understand some key aspects of an effective manger is, Jocelyn Goldfein. Jocelyn is a technology executive and investor. She is the managing director and a general partner at venture capital firm Zetta Venture Partners. Previously she was a director of engineering at Facebook and vice president of engineering at VMware. Jocelyn is passionate about scaling products, teams, and companies, and she cares deeply about STEM education. In our conversation, Jocelyn talks about the lessons she learned as a manager, how to create a positive work culture, advice for leaders, how to encourage diversity, and much more. You’ll want to listen closely to the helpful insights that Jocelyn has to share! Outline of This Episode Lessons learned How do you go from zero management or leadership experience and expect to hit the ground running? The truth is - you can’t! Most people thrust into a sudden leadership role will struggle at first; no one is born with solid management skills. It is your responsibility to be flexible and learn as you go. Unfortunately, in most situations, someone won’t come along and hold your hand, showing you exactly what you need to do. If you can find a mentor or a peer who has also been thrust into a new area of responsibility, then learn from them. Leadership is often lonely, but it doesn’t have to be. Motivation is a manager’s superpower Did you know that motivation is a manager’s secret superpower? It’s true! While some managers will try to dangle carrots or get their team members to perform with sticks, good managers will search for a deeper motivation. Remember, people are not systems or machines; they don’t always respond in predictable or logical ways. If you want to improve your management skills, you need to focus on praise and encouragement. Don’t be so quick to jump to financial incentives - most people just need to feel like they are moving in a positive direction and accomplishing their goals. How to create a healthy culture What does a healthy culture in an organization look like? Does it all come down to putting the right words on the wall or the right onboarding video? Culture starts from the top. Jocelyn Goldfein’s definition of culture is the behavior you reward and punish. What behavior does your organization reward and punish? If your successful leaders embody the vision and values of the organization, then you are headed in the right direction. You can learn more about Jocelyn’s perspective on building a healthy work culture by reading her blog post located in the resources section at the end of this post. Diversity in the workplace One of the key aspects of improving your management skills is learning to pay attention to the level of diversity in your workplace. Diversity is a critical component, especially when it comes to the technology sector. If you want to see your team’s potential increase - then pay attention to the level of diversity! There is a massive opportunity right now for tech companies to tap into underrepresented groups in the workforce. Don’t be afraid or worried about diversity - embrace it. Start with an assessment - where is your organization at, right now? Is there a sufficient level of diversity and inclusion, or is there room to grow? To learn more about improving your management skills by focusing on diversity and other helpful topics, make sure to catch my full conversation with Jocelyn on this episode of Simple Leadership - you don’t want to miss it! Resources & People Mentioned Influence: The Psychology of PersuasionDebugging the Development Process Connect with Jocelyn Goldfein Jocelyn Goldfein - Los Altos, California | Professional Profile | LinkedInJocelyngoldfeinJocelyn Goldfein – MediumJocelyn Goldfein | AngelListJocelyn Goldfein (@jgoldfein) · TwitterJocelyn Goldfein -...

What does it look like to create a work environment where employees can succeed and thrive? Are there steps you can take as a leader to encourage and support your team members in a meaningful way? Here to help us understand what makes Asana a, “Top 5 Best Place to Work” is my guest, Scott Carleton. Scott is currently the Site Lead of Asana’s NYC office, dedicated to enabling all teams to collaborate effortlessly. Previously, Scott was the VP of Technology at Andela, empowering engineering talent across Africa. Scott co-founded Artsicle as CTO, building a global community of visual artists now featuring over 6000 creators in 100 countries. His work on Artsicle's discovery engine, which was able to create a personalized experience for passive users, earned NYER's "Best Use of Technology" award in 2013. Scott also built the first internal engineering team at Teachers Pay Teachers from 0 to 12, while integrating a high functioning remote team. In our conversation, Scott talks about his journey to management, lessons he has learned along the way, the value of transparency, why an empowering work environment is so important and much more. You’ll need pen and paper for this one - Scott has a ton of helpful insights to share. Outline of This Episode The value of transparency Throughout your career, are there any values or principles that stand out to you as “Must-haves” to create an empowering work environment? Maybe for you, it’s integrity or competency. For Scott Carleton and the folks at Asana, one of the top values is transparency. Transparency is crucial, especially for a distributed company like Asana. Scott says that the value of transparency is constantly top-of-mind for him as he engages with his team and works to build consistency and collaboration at Asana. Hand-in-hand with transparency is Scott’s goal to make as much of their processes and systems as clear and understandable as possible. While this is no easy task, Scott is proud of the ground they’ve been able to cover thus far. How to empower your team members Any good manager worth their salt focuses not only on their team members’ productivity but also looks for ways to encourage and empower them as individuals. Can you think of a manager who has empowered you at critical moments in your career? What did they do that made their efforts stand out? From his time at Andela, Scott learned the value of providing his team members with applicable growth opportunities - not just any growth opportunity but - applicable ones. The difference here is key - while it might be a good experience for someone on your team to level up on JavaScript - if it doesn’t apply to the work they are currently engaged in it’s not really that helpful. How do you empower your team members? What growth opportunities do you provide them? Creating a healthy work environment At some point in their career - just about everyone encounters a dysfunctional and unhealthy work environment. How can leaders like you ensure that the environment you are building is a healthy and empowering one? One of the primary reasons Scott joined Asana is their relentless commitment to organizational health. They’ve created clear and concise pathways that encourage their managers and team members to reflect on and learn from projects that were successful and unsuccessful. It is of paramount importance to Asana as an organization that everyone understands how their tasks directly contribute to the overall mission of the company. To hear more about how this plays out at Asana - from Scott’s perspective - make sure to listen to this episode of Simple Leadership. What it takes to be an effective manager Let’s face it; life as a manager is not for the faint of heart. Yes, you get a lot of great opportunities to influence your team and make great strides for your organization, but there is also a fair share of challenges and obstacles that come with the territory. How do you navigate those challenges and serve as an...

As the economy and various business sectors continue to evolve, many leaders are looking at how transitioning to a distributed company might be the best option going forward. I had the pleasure of sitting down with Zapier’s Bryan Helmig to discuss all the benefits and some of the challenges involved with running a distributed company. Bryan co-founded Zapier in late 2011 with his friends Mike and Wade, and they were soon admitted to Y Combinator’s YCS12 batch. Zapier is a web automation application, with Zapier you can build Zaps which can automate parts of your business or life. A Zap is a blueprint for a task you want to do over and over. In our conversation, Bryan and I discuss the crucial role of hiring, what that process looks like at Zapier, the three ingredients for running a successful distributed company, lessons he has learned along the way, and much more. I can’t wait for you to dive in and learn from Bryan’s fascinating perspective! Outline of This Episode [1:45] Guest Bryan Helmig shares his background and why he started Zapier.[5:20] Why hiring is one of the most critical aspects of a startup.[8:50] What does Bryan look for when hiring Engineering Managers and remote employees?[13:20] Three ingredients for running a successful distributed company.[16:50] The benefits of a fully distributed company.[21:30] Bryan describes the challenges he has faced with running a distributed company.[25:00] How does Zapier optimize their hiring process?[31:00] What does the Zapier on-boarding process look like?[36:00] Change is the only constant.[39:30] Why you need to keep an eye on the mental health of your remote employees.[43:00] Tools and resources that Bryan recommends.[44:30] Why people should consider working at Zapier. Why you need to pay attention to your hiring process. What would you identify as the number one area that business leaders should focus on as they work to take their business to the next level of growth? Should they focus on big-picture strategies or less sexy aspects like their hiring process? Looking back at the growth of Zapier, Bryan Helmig says that the hiring process is the most important area for businesses in general and startups, in particular, to focus on. Hiring can be even more complicated for a distributed company but, in Bryan’s view, it doesn’t have to be. At the end of the day, it all comes down to relationships - the people who you hire and trust are critical to your business’ health. Learn more about Bryan’s approach to the hiring process at Zapier by listening to this episode. 3 ingredients for running a successful distributed company. Let’s face it, running a successful business is hard enough but the challenges can increase tenfold when you are operating as a distributed company. Thankfully, leaders like Bryan Helmig are leading the way and paving a path forward. In our conversation, Bryan was kind enough to share his three ingredients for running a successful distributed company. Team - Focus on less “poster values” and emphasize behavior values like, “Default to action.”Tools - Don’t be a robot; build a robot. Tools drive how your organization works.Process - Be willing to revisit and change your processes as you go. Which aspect of Bryan’s three ingredients resonates the most with you? Make sure to catch my full conversation with Bryan as he expands on these three ingredients and much more. The advantages of a distributed company. What is your knee-jerk reaction when you think of a distributed company? Do you have a positive impression or a negative one? Don’t assume you know all of the relevant information, get it from the source! One of the unique advantages of a distributed company is the limitless opportunities it provides when seeking talent. You don’t have to limit your talent search to those in your geographical area; you can choose from qualified candidates all over the world. Connected to this unique advantage is another advantage - diversified points of view....

There’s good news for all you tech leaders who feel you got thrown into management without much preparation - leadership can be learned. My guests on this episode of SimpleLeadership are Johnathan and Melissa Nightingale, the founders of Raw Signal Group - a company with a simple promise, “We Build Better Bosses.” They are also best-selling authors of the book, “How F*cked Up Is Your Management?: An Uncomfortable Conversation About Modern Leadership.” I can't think of two people better suited to talk to about the challenges of tech leadership. Prior to founding Raw Signal Group, Johnathan and Melissa were both tech execs who spent their careers running large parts of companies (product, engineering, data, design, marketing, PR, etc.). It’s honestly hard to find a role that one of them has not taken on. Through their work with Raw Signal Group, they've helped thousands of leaders understand their roles, build their skills, and be better bosses. Join us for this great conversation and learn how great leadership can be learned. Outline of This Episode [1:50] The winding path that brought Johnathan and Melissa to their current roles[7:18] Leadership skills can be learned across disciplines[13:19] The point Johnathan and Melissa realized a gap existed in tech leadership[16:56] What are the mistakes that happen over and over in tech leadership?[24:35] The most important thing for new managers to focus on the first 90 days[36:00] Leadership is not about good intentions[40:40] How can managers contribute more to family planning and maternity leave issues?[43:15] How Raw Signal Group can build better bosses for tech companies The same management leadership issues exist across disciplines and industries There is a strange belief that exists among those who are in tech management roles - they think that leading engineers is somehow different than what other leaders within their organization deal with. It’s true that engineers can be a bit unique, but there is much more that can be learned from other leaders in different areas of your organization than you think. Even leaders in entirely different industries have something valuable to offer. Johnathan and Melissa speak to the issue by pointing out how significantly tech leaders can be helped when they learn to humbly approach others they see doing things well to simply ask for insight into how they do it. Listen to hear how they coach leaders to build cohorts of help within their own organizations, across departments. Have you identified the leadership skills you want to steal? When it comes to learning leadership skills, every leader needs to be on the lookout for the things the leaders around them do well. It’s one way you can see things in others you admire and develop a list of leadership qualities or skills that you want to improve in yourself. Melissa refers to it as the “leadership skills you want to steal.” But the truth is that you don’t really have to steal anything. Most leaders are eager to help others understand the things they do well. But it requires that you have the bravery to approach them to ask for help. There are no natural leaders. You can learn good leadership We’ve all heard someone described as a “natural born leader.” While we understand what is meant by the phrase, Johnathan and Melissa push back against the notion that some people are born with the skills needed to be leaders and others are not. Even casual observation proves it not to be true. None of us naturally know the critical skill of leading teams, having effective one on ones, conducting effective meetings, or firing someone. If that’s the case, then how did those who do those things well get that way? They learned the skill over time. Melissa and Johnathan developed their company, Raw Signal Group after years of observing the terrible leadership practices being carried out in the tech industry. They felt that not only did they have a responsibility to ensure that their personal leadership...

Steph is the Head of Publications at Toptal, a serial maker, and a supporter of women in technology. Outside of leading a remote team of a few dozen, she is a self-taught developer that builds projects related to women in technology, remote work, and self-improvement. She’s launched products that have hit #1 on Product Hunt, articles that have trended the top of Hacker News, and was nominated for Maker of the Year in 2018. She actively supports women in technology by speaking about the psychology behind inclusion and through building resources like FeMake and is a judge for the Toptal Women’s Scholarship. On today's episode we discuss some of the best practices for managing remote teams based on her recent blog post."Managing Remote Teams: A Psychological Perspective." Continue on for a great discussion with Steph. Contact Info: Personal website: https://stephsmith.io Twitter: >?q=https://twitter.com/stephsmithio&source=gmail&ust=1554743123782000&usg=AFQjCNFW2gh0QlgMfBOjUSeqUQrZvcDJbw">https://twitter.com/stephsmithio LinkedIn: https://www.linkedin.com/in/stephaniesmith93/ Show Notes: Steph's Awesome Book List Best Practices for Managing Remote Teams: A Psychological Perspective Thanks for the Feedback Radical Candor Algorithms to Live By: The Computer Science of Human Decisions Give and Take: Why Helping Others Drives Our Success The Four Tendencies: The Indispensable Personality Profiles That Reveal How to Make Your Life Better (and Other People's Lives Better, Too)

Patrick has spent his career applying his engineering talents to the healthcare industry. In that time he’s focused on learning and growing as an engineer, a teammate, team lead, and more recently as an engineering manager. He considers himself a people gardener and coalition builder and believes in people-first leadership. Patrick loves teaching and tackling people and process opportunities to help teams and individuals grow. On today's show we discuss communication, psychology, having a growth mindset and his upcoming conference talk. Contact Info: twitter: patrickjpena medium: https://medium.com/@patrick.pena linkedin: https://www.linkedin.com/in/patrickjpena/ Show Notes: Crucial Conversations The LeadDeveloper Conference Calibrate Conference BiFrost Conference San Francisco Engineering Leadership Community

Jason Wong is a proven engineering leader, diversity & inclusion consultant, and doughnut enthusiast. With almost two decades of experience in building and scaling web applications, he has worked in a range of industries from academia to online media and e-commerce. He helped establish web development and administrative computing at Columbia College, led development of premium video streaming services at Yahoo! Sports, and spent seven years at Etsy leading their Infrastructure Engineering team. He currently works with engineering leaders to improve their engineering management practices and establish inclusive cultures. Contact Info: JWong Works Website Twitter: https://twitter.com/attackgecko Show Notes: NCWIT Women in tech report Etsy’s recommended reading list for allies Why Women Leave Tech Maleallies.com Lara Hogan’s Ally Resources Geek Feminism – Feminism 101 Project Include