The Startup CTO's Handbook, a book covering leadership, management and technical topics for leaders of software engineering teams - ZachGoldberg/Startup-CTO-Handbook
leadership
Leadership isn’t about a title or position — it’s about generosity, says organizational expert Joe Davis. Drawing on his extensive experience as a people manager, he shares three essential tips for leaders to unlock the potential of their teams by listening generously, embracing vulnerability and leading with humanity — and shows how it's possible to both earn trust and drive results.
Extensive research has indicated the benefits of showing gratitude to those around you, including your colleagues or employees. However, a new study suggests that the timing of these expressions can make a big difference. Through two experiments and an analysis of a top hospital’s intensive care units, researchers found that when you express gratitude to others before they engage in a distressing task it helps counteract some of the negative emotions associated with the task. Expressing gratitude early also makes employees more likely to persist through difficulty and bounce back and be resilient following failure. The authors suggests ways to show gratitude meaningfully and create a culture where your employees feel their work is seen, supported, and valued.
Crossbeam CEO and co-founder Bob Moore shares his tools for quashing biases in pursuit of the truth at every stage of company building.
The way we work has changed — and so has leadership. Leaders are under new pressures to perform at higher levels and adapt quickly to changing demands. In this article, the author shares advice from three leadership experts and outlines the six skills leaders need to succeed: 1) emotional aperture; 2) adaptive communication; 3) flexible thinking; 4) perspective seeking, taking, and coordinating; 5) strategic disruption skills; and 6) resilient self-awareness. Developing these six key leadership skills isn’t just about your personal growth, it’s about shaping the future of work and inspiring those around you.
These two principles are equally powerful and critical to manage behavior, but the order matters.
Research suggests that the most effective leaders adapt their style to different circumstances — be it a change in setting, a shift in organizational dynamics, or a turn in the business cycle. But what if you feel like you’re not equipped to take on a new and different leadership style — let alone more than one? In this article, the author outlines the six leadership styles Daniel Goleman first introduced in his 2000 HBR article, “Leadership That Gets Results,” and explains when to use each one. The good news is that personality is not destiny. Even if you’re naturally introverted or you tend to be driven by data and analysis rather than emotion, you can still learn how to adapt different leadership styles to organize, motivate, and direct your team.
When you’re part of a company’s management structure, there will be moments when you’ll have to represent a decision your bosses made that you don’t agree with to your team. Carrying the proverbial flag on behalf of the powers-that-be won’t feel good, but that’s part of the job. Barring a decision or action that is immoral, illegal, or unethical, standing behind decisions that don’t go your way is one of the most challenging things you’ll have to do as a leader. Doing so effectively requires thoughtful preparation. Here are six strategies to use when you have to convey a decision you don’t agree with.
Discover the power of examples in shaping our lives. Explore quotes on example and how they inspire us to reach new heights.
A theme in my practice is the leader who's seeking to increase employee motivation. In this context it's important to bear in mind the work of Frederick Herzberg, a 20th century psychologist who had a profound influence on our understanding...
Storytelling is an important leadership skill, and executives who want to succeed should master five types of narrative: Vision stories, which inspire a shared one; values stories that model the way; action stories that spark progress and change; teaching stories that transmit knowledge and skills to others; and trust stories that help people understand, connect with, and believe in you.
When you have to communicate a difficult organizational decision to employees, it’s hard to know how much information to provide when you can’t be fully transparent yet. Saying nothing can undermine people’s trust in your motives and compassion, whereas saying too much can leave people feeling overwhelmed and vulnerable as they struggle to process the information and implications. Striking the right balance between these two extremes is a tricky exercise for leaders. The author presents five strategies to help you figure out what to say and do when you can’t yet be fully transparent with your employees.
Many of my discussions with product leaders (CPOs, VPs and others who manage teams of product folks) are about the substance of product management: portfolios, competing stakeholders, pricing & packaging, tarot cards as a revenue forecasting model. Last week, though, in my product leadership workshop, we had an extended discussion about
3 tips for coaching people, from a former military psychologist
Industrial genius Carl Braun believed that clear thinking and clear communication go hand in hand. Here the guide on writing productively to get things done.
Some coaching transitions do the unthinkable, like Sonny Dykes and TCU. Others flounder, like Scott Frost and Nebraska. How, and why?
What exactly is psychological safety? It’s a term that’s used a lot but is often misunderstood. In this piece, the author answers the following questions with input from Harvard Business School professor Amy Edmondson, who coined the phrase “team psychological safety”: 1) What is psychological safety? 2) Why is psychological safety important? 3) How has the idea evolved? 4) How do you know if your team has it? 5) How do you create psychological safety? 6) What are common misconceptions?
How should you manage a team that is trying to achieve results out of the ordinary?
A curated and opinionated list of resources for Chief Technology Officers, with the emphasis on startups - kuchin/awesome-cto
Mochary Method Curriculum ⭐Interested in coaching or software to help implement the Mochary Method at your company? Please fill out our interest form here. Make a copy of this curriculum for yourself. After reading a sub-doc, please write on this main doc your answers to the following questio...
Transformational leaders are exceptional communicators. In this piece, the author outlines four communication strategies to help motivate and inspire your team: 1) Use short words to talk about hard things. 2) Choose sticky metaphors to reinforce key concepts. 3) Humanize data to create value. 4). Make mission your mantra to align teams.
Whether it’s caused by culture clash, cultural inertia, or total toxic collapse, broken culture syndrome can sink an organization. But there’s a way out.
Far too often, team members expect to be given downward feedback, but unless they’re explicitly invited to offer upward feedback, they won’t know that it’s even an option. As a manager, it’s your job to ask your employees for feedback on your own performance. How else will you know what you should keep doing and what you should be doing differently? Nevertheless, you might find that your direct reports are reluctant to give you the feedback you need to improve, or even sustain, what’s working. This article addresses five common barriers that managers face in getting helpful feedback from direct reports, and how to address them so that you can gain the insights you need.
Today, Zapier automates work by connecting with over 5,000 apps. The company has been profitable since 2014 and is valued at $5B – with 700 employees working remotely. Wade, Zapier CEO, shared his learnings growing into the role of a growth-stage CEO.
Corporate leadership today is more public than ever before thanks to digital communication and the web. The status quo has been upended by the ease with
Have you ever wondered about internal organization dynamics and why some groups of people (who aren’t on the same team) are more successful than others? Why different “tribes” inside the organization seem to be at war with one another lowering performance in increasing politics? Why certain groups of people never seem to do anything? Or why …
Former Google SVP of Products Jonathan Rosenberg on the quintessential lessons every leader needs to learn.
The reality is that you will never prioritize the CEO’s "great" new idea. Here's how to let your strategy say "no" for you.
Russ Laraway wades through all of the competing opinions, complex frameworks and advice out there on how to be a better manager, creating a simple, data-backed leadership toolkit.
Editor’s note: Scott Weiss is a partner at Andreessen Horowitz and the former co-founder and CEO of IronPort Systems, which was acquired by Cisco in 2007. An approachable and authentic CEO is essential to fostering a high-performance, open communications culture.
U.S. Army Engineer School Commandant’s Reading List
How to minimize the drama and keep your team on track.
I’ve found the following to be common (and not easily taught) in people whose product skills I admire.
John Farrell took his team from the bottom of their division last year to the 2013 World Series with a set of tactics every manager should learn.
“I’ve probably revised this investor pitch deck 200 times,” a founder told me recently. She’d met with more than 50 potential investors before closing a seed round last month. This might sound excessive to some, but her experience is not unusual. Entrepreneurs often spend hundreds of hours raising funds from angel and venture capital investors. While these activities are clearly important, analysis of new data on startups suggests that founders should also dedicate significant time to something that many people overlook: recruiting great mentors. This simple strategy can increase a company’s odds of success more than almost anything else.
Awesome List of resources on leading people and being a manager. Geared toward tech, but potentially useful to anyone. - LappleApple/awesome-leading-and-managing
The home of Process Excellence covers topics from Business Process Management (BPM) to Robotic Process Automation (RPA), AI, Lean Six Sigma and more. Latest news, freshest insight and upcoming events and webinars.
Apple is famous for not engaging in the focus-grouping that defines most business product and marketing strategy. Which is partly why Apples products and advertising are so insanely great. They have the courage of their own convictions, instead of the opinions of everyone else’s whims. On the subject, Steve Jobs loves to quote Henry Ford […]
Leadership Now is a leading source for leadership development and analysis. We believe that anyone can make a difference by leading from where they are.
"The success of your startup is determined before you ship a single line of code." Okay, you’re right, Sun Tzu, the ancient Chinese war general and author
We all know that leaders need vision and energy, but after an exhaustive review of the most influential theories on leadership–as well as workshops with thousands of leaders and aspiring leaders–the authors learned that great leaders also share four unexpected qualities. The first quality of exceptional leaders is that they selectively reveal their weaknesses (weaknesses, not fatal flaws). Doing so lets employees see that they are approachable. It builds an atmosphere of trust and helps galvanize commitment. The second quality of inspirational leaders is their heavy reliance on intuition to gauge the appropriate timing and course of their actions. Such leaders are good “situation sensors”–they can sense what’s going on without having things spelled out for them. Managing employees with “tough empathy” is the third quality of exceptional leadership. Tough empathy means giving people what they need, not what they want. Leaders must empathize passionately and realistically with employees, care intensely about the work they do, and be straightforward with them. The fourth quality of top-notch leaders is that they capitalize on their differences. They use what’s unique about themselves to create a social distance and to signal separateness, which in turn motivates employees to perform better. All four qualities are necessary for inspirational leadership, but they cannot be used mechanically; they must be mixed and matched to meet the demands of particular situations. Most important, however, is that the qualities encourage authenticity among leaders. To be a true leader, the authors advise, “Be yourself–more–with skill.”
A company study found that a manager’s technical skills were far less valued by employees than people skills.
Fight the Good Fight The probability that we may fall in the struggle ought not to deter us from the support of a cause we believe to be just. Try Honey Before Vinegar If you would win a man to your cause, first convince him that you are his sincere friend. On the contrary … …
The Ten Golden Rules of Leadership explores the classical figures to determine the ten crucial axioms of leadership. Rule 1. Know Theyself. Rule 2 ...
In response to yesterday’s post on management design patterns, many readers asked for examples of best practices. So I’m going to write about the management best practices I have been taught and I have observed in startups. This is the first post of that series. The first management technique is called Situational Management, one that my wife, a terrific manager at Google, taught me. A manager’s most important function in a startup is to motivate employees to accomplish the business’s goal.
In the least surprising news of 2016, Yahoo is selling its core business to Verizon for a sad $5 billion. Everyone knew this was coming — but for some reason, the headlines keep blaming Marissa.
On Sunday, I was fortunate enough to give a talk at the 9th annual Harvard Business School Entrepreneurship Conference. I’m trying to be better about posting the slides from these talks as t…
The ability to get issues on the table and work through them constructively is critical to having a healthy culture. Managers can normalize productive conflict on your team by using an exercise to map out the unique value of each role and the tensions that should exist among them. Draw a circle and divide that circle into enough wedges to represent each role on your team. For each role, ask: What is the unique value of this role on this team? On which stakeholders is this role focused? What is the most common tension this role puts on team discussions? Answer those questions for each member of the team, filling in the wedges with the answers. As you go, emphasize how the different roles are supposed to be in tension with one another. With heightened awareness and a shared language, your team will start to realize that much of what they have been interpreting as interpersonal friction has actually been perfectly healthy role-based tension.
Leadership has traditionally been taught as a set of larger actions, such as having a difficult conversation or coaching someone. In reality, leading well is an integrated activity, in which one is doing many things simultaneously. One way to learn to do this better is to think about leadership as a series of small actions that are practiced, then carefully sequenced and interwoven during interactions. For instance, instead of thinking of something as a “difficult conversation,” a leader might aim to disarm, then show appreciation, then appeal to values. Research identifies 25 such actions, and learning to implement them in the right circumstances can help one become a better leader.
This is the legendary presentation about cross-functional teams from Ken Norton that made donuts and product management synonymous.
Fuel success by linking a company’s strategic goals to the reasons people are proud to work there.
Employee well-being and happiness are surprisingly powerful predictors of performance.
If you’re worried that your employees are eyeing the door, it’s time to start having some important career-defining conversations. In this piece, executive coach Susan Peppercorn outlines five questions to start asking your direct reports so that you can get a better sense of how they’re feeling about their positions: 1) How would you like to grow within this organization? 2) Do you feel a sense of purpose in your job? 3) What do you need from me to do your best work? 4) What are we currently not doing as a company that you feel we should do? 5) Do you have the opportunity to do what you do best every day? When managers make checking in with these five questions a regular part of how they interact with their employees, it helps ensure that people feel seen and valued. And when managers help individuals on their teams feel that way, they’re more likely to be rewarded by employees who become advocates for the department and organization, no matter how long they stay.
Web magazine about user experience matters, providing insights and inspiration for the user experience community
The traditional corporate approach to motivating people has been a combination of carrots and sticks: a system of financial incentives designed to mobilize everyone around a plan designed by a few smart people at the top. Multiple studies have confirmed that, for any work involving cognitive or creative skills, financial rewards do not drive motivation and performance. So, what does? According to former Best Buy CEO Hubert Joly, it takes several mutually reinforcing elements to create an environment that unleashes the kind of human magic necessary for a company purpose to take root and flourish. He presents six ingredients to create your company’s unique recipe for human magic.
If you want to help people, don’t give them advice. Do this instead.
Every company makes decisions based on the highest paid person's opinion. It turns out it's just a hypothesis. Here's how to tame it.
Front's CEO and co-founder Mathilde Collin shares why a founder’s discipline matters more than vision, unveiling her own best practices and templates for communication, time management, fundraising and team building.
Molly Graham helped forge a work culture at Facebook that's withstood huge amounts of growth. Today, she's something of a rapid scaling expert. Here's the key to doing it right, she says.
Building effective organisations is a remarkably useful, if rare, skill. This is what it looks like, what it consists of, and how to tell if someone has it.
Frustrated with your Executive team meetings? We tapped 25 top leaders from the startup C-Suite to share their tested tips, from getting started with an executive team to crafting the agenda and tracking success. Whether you're a first-time CEO or seasoned startup leader, there are plenty of new ideas to try from folks at Superhuman, Lattice, Asana and more.
“We are dangerous when we are not conscious of our responsibility for how we behave, think, and feel.”―Marshall Rosenberg, As a founder, my biggest regrets revolve around not having difficu…
It’s important to understand that when you, as a leader, communicate with your team, using weaker words weakens your message and blunts your ability to inspire people. It’s not enough to just throw thoughts out there and hope for the best. You need to actively recommend ideas and assert their worthiness in all of your communications. For example, consider these “power words”: “I’m proposing (not “sharing”) an idea that will make our process more efficient.” “I’m suggesting (not “sharing”) a new logo that better conveys our brand message.” “I’m recommending (not “sharing”) a campaign to make our workplace more diverse.” Ultimately, audiences respond more actively to big points than to small words, but thoughtful leaders need to assess both, knowing that the more powerfully they come across — even in small ways — the greater impact they have on the people they hope to inspire.
Senior leaders, particularly CEOs, confront a central paradox in their work: They generally have access to more lines of communication than anybody else, but the information that flows to them is suspect and compromised. Warning signals are tamped down. Key facts are omitted. Data sets are given a positive spin. All of it isolates leaders in a dangerous information bubble. But they can escape that bubble, the authors argue, by working actively to create a more expansive “listening ecosystem.” They first have to learn how to listen actively themselves, without distraction or judgment, purely for comprehension; then they have to create systems and processes all around them that elevate listening to a constant state of hypervigilance. This sort of sustained attention to listening allows leaders to pick up on early signs of both danger and opportunity—and that, in turn, allows them to do their jobs and serve their organizations better. The authors conclude this piece by sharing advice—gleaned from interviews and personal experience—about how leaders can learn to listen better.
I learned from bosses & peers, including some famous peeps like Reed Hastings, Patty McCord, and Dan Rosensweig. But mainly I learned by doing, supercharged by feedback from many "Friends of Gib."
Industrial genius Carl Braun believed that clear thinking and clear communication go hand in hand. Here the guide on writing productively to get things done.
I've worked at various tech companies: from "traditional" shops and consultancies, through an investment bank, to high-growth tech firms. I've also talked with software engineers working at startups, banking, automotive, big tech, and more "traditional" companies. This mix had a healthy sample of Silicon-Valley companies and ones headquartered outside this
"Unconscious leadership happens when we aren't self-aware, which puts fear in the driver's seat."
Leadership Now is a leading source for leadership development and analysis. We believe that anyone can make a difference by leading from where they are.
Sometimes, deciding what to do is the easiest part of a decision. Being decisive on an issue you hate is a whole different ballgame.
How the Silicon Valley veteran transformed the e-signature pioneer Into a $37 billion powerhouse
The pandemic has forced leaders of hospitals around the world to adopt new practices as they have struggled to contend with the crisis. In this article, the senior leaders of two emergency field hospitals in the United kingdom and the United States — the NHS Nightingale and Boston Hope — share 10 lessons that they learned as they led their clinical staffs during the crisis. These lessons will help hospitals provide better care during the continuing pandemic and after it has ended.
As the crises of 2020 wear on, the unique skills of our country’s Special Operations Forces (SOF) are becoming more and more valuable in the private sector. Their adaptability, excellent judgment, and wide range of training and experience makes SOF veterans well suited to lead in tumultuous times. Companies that want to succeed amid ongoing volatility should take example from the SOF community by seeking to be flexible, de-siloed, and focused on hiring for hard-to-teach skills like emotional intelligence. Interviews with some 20 veterans and coaches revealed the skills that this elite community can bring to American businesses.
Lead Yourself First: Inspiring Leadership Through Solitude [Kethledge, Raymond M., Erwin, Michael S., Collins, Jim] on Amazon.com. *FREE* shipping on qualifying offers. Lead Yourself First: Inspiring Leadership Through Solitude
The military's toughest training challenges have a lot in common with outdoor sufferfests like the Barkley Marathons and the Leadville Trail 100: you have to be fit and motivated to make the starting line, but your mind and spirit are what carry you to the end. A Ranger graduate breaks down an ordeal that shapes some of the nation's finest soldiers.
If you’re looking for a primer on many of the responsibilities of being a startup CEO, read The Great CEO Within. Matt Mochary wrote the book. He founded a company which he sold to MCI and now coaches startup CEOs, amongst other philanthropic efforts. The best part of this book is that it combines descriptions of the key jobs to be done and the frameworks to accomplish them. As CEOs grow their teams and their companies, their calendars densify with meetings until there’s no space to work.
Leadership Now is a leading source for leadership development and analysis. We believe that anyone can make a difference by leading from where they are.
If you work with someone who’s gone too long without feedback and want to help them grow, you’ll need to take an empathetic approach to the conversation. Start by asking questions to clarify their motives. If a leader is constantly forcing their ideas on others, for example, you might start with a question like, “How were you hoping the team would respond to your idea?” Once you are aware of your colleague’s intentions, you need to separate them from their actions in order to have a productive discussion. Acknowledge their original intent, but follow up by stating the negative impact their action actually had on you. Pointing out the gap between what they meant to do and what happened, will help them recognize patterns of unwanted behaviors. Remember that the feedback will be hard to hear — so give them space to feel upset, remind them you are telling them to help them grow, and encourage them to focus on the future.
Airline pilot Alfred Haynes and other leaders who’ve saved lives show that modest people can achieve miracles under pressure.
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Grant said he separates workers along two axes: givers and takers, and agreeable and disagreeable.
Mark Twain once said that the two most important days in your life are the day you are born, and the day that you discover why. My goal for writing this article is to share an approach to discover (or in my case, rediscover) your “why”.
The chairman and CEO of China’s e-commerce giant describes Alibaba’s approach to innovation and how he balances analytics and instinct to push himself to spot hidden opportunities.
Remember that the essence of authority is that people willingly follow your lead. That is what the following strategies are designed to do.
If you want others to follow, learn to be alone with your thoughts
Why do issues remain open secrets in organizations, where multiple employees know about a problem or a concern, but no one publicly brings it up? Researchers recently explored this in a set of studies. They found that as issues become more common knowledge among frontline employees, the willingness of any individual employee to bring those issues to the attention of the top-management decreased. Instead of speaking up, what they observed among their participants was something like the bystander effect, a psychological phenomena describing how people stay on the sidelines as passive bystanders, waiting for others to act rather than do something themselves. If managers want to avoid the bystander effect so that problems don’t go unresolved, they should tell employees that their voices are not redundant and that they need to share their opinions even if others have the same information.
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This is taking your leadership to a whole new level, again.
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One of the most difficult transitions for leaders to make is the shift from doing to leading . As a new manager you can get away with holding on to work. Peers and bosses may even admire your willingness to keep “rolling up your sleeves” to execute tactical assignments. But as your responsibilities become more complex, the difference between an effective leader and a super-sized individual contributor with a leader’s title is painfully evident. To raise the ceiling of your leadership potential, you need to extend your presence through the actions of others, engaging people so that they contribute their best work to your shared priorities. To set the table for effective delegation, make sure you express why something is important to you, confirm that your expectations for the work have been clearly communicated, ask how much of your involvement they need, and practice saying no. Don’t let a focus on execution hold you back from the big-picture work of leading. If you delegate with these principles in mind, the work will get done, because the right people will be focused on the right tasks.
As I focus on becoming a better manager of engineers, I have been reflecting more and more on the advice that produced a 10X boost in my…
Plus how to actually do it—with sample scripts
Big ideas, strong-willed characters, impossible deadlines and close quarters — if you wrote out a recipe for conflict, it might bear an uncanny resemblance to the high-stakes, pressure-cooker environment of a startup. We spoke with top engineers, seasoned managers and experts in human behavior to share their experience-tested wisdom on conflict mediation and management in rapidly scaling companies.
Business leaders make countless decisions that affect employees, customers, shareholders, communities, and even society as a whole. Traditionally, there have been two important traits that leaders need to have: intellect (IQ) and emotional intelligence (EQ). Today, however, they also need a third: decency. Having decency means a leader not only has empathy for employees and colleagues but also has the genuine desire to care for them. It means wanting something positive for everyone in the workplace and ensuring everyone feels respected and valued. It’s evident in daily interactions with others, and implies a focus on doing right by them. As trust in business erodes, this type of triple-threat leadership is vital: Intellect and emotional intelligence are important, but it’s decency that ensures IQ and EQ are used to benefit society, not tear it down.
Leadership Now is a leading source for leadership development and analysis. We believe that anyone can make a difference by leading from where they are.
As leader of the team, you have significant influence over your team
Based on data from 597 people, the best ways to build trust as a leader aren’t what you think they are. How do you build trust as a leader? The answer seems intuitive enough. For many of us, …
Thoughtful, empathetic language can make or break your business relationships
Explore a glimpse into how M. Seibel thinks about leadership attributes and some contrarian views that may be at the heart of how he picks great companies.
For the first eight years of my career I was in the U.S.
“There’s no difference between a pessimist who says, ‘Oh, it’s hopeless, so don’t bother doing anything,’ and an optimist who says, ‘Don’t bother doing anything, it’s going to turn out […]
Most bosses live in fear that their best employees will leave, so it might seem to be a bad idea to encourage your stars to consider outside offers. But in fact, it sends employees a clear signal that you really care about their learning and development. Openness allows for an honest conversation between you and each employee about their future career path. If they do decide to leave, they’ll be more likely to recommend you as a great boss, and also more likely to return at some future point.
Reducing injuries brings down your worker’s compensation costs, but that’s not what’s should drive companies to examine their rate of serious injury. Instead, leaders should do so because they care about the people who work for them. Doug Conant, former CEO of Campbell’s Soup Company, writes about what he learned by watching David White, Global VP of Supply Chain, lead with his heart first.
Whether you're an experienced tech manager, a newbie, or an engineer who wants ...
The most successful outlaws live by a code, and in many ways John Perry Barlow was an archetypal American outlaw all of his life.
We use our Leadership Principles every day, whether we’re discussing ideas for new projects or deciding on the best way to solve a problem. It’s just one of the things that makes Amazon peculiar.
Retired Army general and special forces commander Stanley McChrystal shares his insights about adaptable teams and organizations.
My earliest memories of delegation involve elementary school group projects in which my classmates didn’t take the assignment seriously. More often than not, this left me in the undesirable position…