Knowledge shared by our community

A Delegation Disaster

While working as a Director of Infrastructure Security Consulting, the author delegated authority to one of the consultants on the team while they were away on a 7-hour flight. When they returned, the project was in disarray and the client was talking about firing them. The author learned that while they could delegate authority, they could not delegate responsibility and ultimately they were accountable. They gathered the team and explained the situation, taking responsibility and not passing the buck. This instilled confidence in the team and reminded the author to be careful when delegating.

Handling Stressful Situations

In a high-stress security incident, a consultant was able to help the team leader by providing a plan and delegating tasks. This helped to reduce stress and inspire confidence in the leader, showing that projecting confidence and competence is essential when leading a response effort.

Helping Engineers On Their Career Path

This engineering manager held a one-on-one with a team member who felt overlooked for promotions. The manager encouraged the team member to step up and be seen, and developed an official plan for his career path. The manager then gave the team member a challenging project to take leadership over, and after it was completed, the team member was able to write a follow-up paragraph to get visibility. This was a lesson for the manager that it is their role to help their team move up in their career, and that they should work for the team instead of the other way around.

Improving at One-on-ones

After being promoted to team lead, an introvert struggled to lead one-on-one meetings. Initially, the conversations were always technical, but after reflecting on a disagreement with the team, the lead decided to be more direct and focus on personal topics. This allowed them to gain insight into the team's health and address issues before they became bigger problems.

Establishing Credibility In A New Team

When starting as Director of Engineering at Datadog, the author had to quickly learn the systems and architecture of the company. To do this, they set up the environment locally, read development guides and wiki pages, read code, and looked at monitors and errors. They also took a personal approach by setting up one-on-ones to get to know the team and understand what motivated them. The author learned that it is important to get to know the people working for you as well as the code.

Cross-Team Project Cooperation

Cross-team projects can be difficult to manage, but by assigning specific tasks to people on both teams, allowing them to make decisions, and trusting engineers to do the right thing, projects can be successful. Clear goals should be set from the start and ownership should be established to ensure the project is a priority.

From BFF To Boss

When the author was promoted to team lead at Buzzfeed, they had to learn how to manage people who had previously been their peers. They realized they needed to be direct and transparent about the change in their relationship, and to understand what motivated their engineers. Through this process, they learned how to make the right decisions to maintain positive relationships with their team.

How I Reduced Silos And Increased Team Productivity

When the author took over WorldGaming in 2015, the team was siloed and process-driven. The author restructured the team, growing it to 26 people, and implemented a self-managing (holacrazy) team. This approach was successful, with the team launching 14 major features and pushing to production 100 times in a year. However, managing 26 people directly was challenging and time management was crucial. The author learned that if a manager can't manage their own time well, they should not use this model of management, but if they can, it can be very effective.

Building An Engineering Career Ladder

This article discusses the process of creating a career ladder for engineers in a growing company. It outlines the steps taken to understand what creates value for the business, to talk to managers and individual contributors to understand what traits they look for, and to look at other companies to provide a framework for the rubric. It also emphasizes the importance of involving everyone in the process and investing early to get it right.

More Methodical, More Efficient

A software engineer working on an email system encountered a bug that they couldn't fix. Their manager taught them to look at the source code to understand the technology and the bug, rather than just trying to guess solutions. This was a valuable lesson in patience and understanding, which the engineer was able to pass on to their own engineers.

Starting and growing a team in a new city

When expanding a business to a new city, it is important to ensure that the culture of the original office is honored. This can be done by visiting the main office regularly, having explicit conversations about the company culture, and creating virtual company meetings to maintain the connection between offices. It is also important to be aware of the potential for "echo chambers" of subjective realities, and to encourage open communication between offices to avoid any issues.

Gaining the trust of non-technical leaders

Leaders often fail due to a lack of empathy and active listening, which can be difficult to teach. To address this, organizations should focus on a user-centered design approach and leaders should focus on actively listening and repeating what they hear. This will help build trust and understanding between leaders and their teams.

Going from no testing to full QA automation

As an engineering team grows, it is important to maintain a QA-to-engineering ratio to ensure that there is always a third party testing the code. Manual testing is a great way to start, but automation is key to catching bugs quickly. Regressions must be treated with high priority to maintain user trust.

Being an engaging speaker and presenter

As an engineering manager, it can be difficult to engage employees in topics that may be uninteresting to them. To overcome this, one can use a "method acting" approach to emotionally connect to the material, as well as "acting hacks" such as pregnant pauses, volume levels, humor, and eye contact. Additionally, being vulnerable with the audience can help to generate trust and focus.

Managing toxic employees and atmospheres

This article discusses the problem of hiring false positives and false negatives, and the actions taken to address two toxic employees. In the first case, swift and constructive feedback was given, and the employee was eventually let go. In the second case, the employee was talented but slow, and it was necessary to let them go in order to unblock other employees and the organization. The lesson learned is to listen to gut feelings and act swiftly when an environment feels toxic, even if it means taking on legal risk.

Resolving severe personality conflicts

Through personal therapy and psychology training, I have developed a set of techniques to help address personality conflicts between two individuals. By facilitating 1-on-1s with a third party present, the technique encourages each person to speak openly and be heard. This has been successful in transforming relationships, and has led to me being called the "Chief Therapy Officer" at my company. The lesson learned is that organizations can survive with dysfunctions, but those that can have employees listening to each other with empathy until they are truly heard are more likely to function without excessive bureaucracy.

Peacefully managing out low-performing employees

Firing people is a difficult and potentially legally risky task for managers. To ensure the process is done well, managers should have regular 1-on-1s with employees to discuss performance and create a Success Plan with clear goals. If an employee is not happy, managers should have an open conversation to identify what would make them happy, even if it's not in their current role. Quarterly performance reviews should also be held to record detailed information on performance.

Growing and mentoring managers of managers

This article discusses how to combat the perception that management is the only path of growth for engineers. It suggests proactively communicating that there are two separate tracks, both of which are equally respected and deserving of the same levels of compensation and seniority. Additionally, it suggests having mentorship and lead positions, management training options, and enabling autonomy and trust by not having "skip level" 1-on-1's. Finally, it suggests having managers of managers audit their teams and engage with those affected by the team's work.

Enabling a Pro-Diversity Culture

In order to create a pro-diversity culture, it is important for the executive team to be vocal and open about their stance. This requires individuals to bring their whole selves to work and be open about their unique backgrounds. Additionally, trainings should be embraced as a way to educate employees about unconscious bias and microaggressions. By practicing empathy and taking these issues seriously, organizations can create a diverse and safe environment for all employees.

Measuring & Communicating Team Success

In order to measure the success of the Product and Engineering organization, a "Monthly Report" was created to provide measurable data and qualitative content to the executive team and CEO. This report includes an executive summary, highlights and goals, capital expenses, performance & uptime, product development & quality, and visual charts and graphs. This report has been a great way to communicate progress and keep on top of what is going well or not well with the team.

A Delegation Disaster

While working as a Director of Infrastructure Security Consulting, the author delegated authority to one of the consultants on the team while they were away on a 7-hour flight. When they returned, the project was in disarray and the client was talking about firing them. The author learned that while they could delegate authority, they could not delegate responsibility and ultimately they were accountable. They gathered the team and explained the situation, taking responsibility and not passing the buck. This instilled confidence in the team and reminded the author to be careful when delegating.

Handling Stressful Situations

In a high-stress security incident, a consultant was able to help the team leader by providing a plan and delegating tasks. This helped to reduce stress and inspire confidence in the leader, showing that projecting confidence and competence is essential when leading a response effort.

Helping Engineers On Their Career Path

This engineering manager held a one-on-one with a team member who felt overlooked for promotions. The manager encouraged the team member to step up and be seen, and developed an official plan for his career path. The manager then gave the team member a challenging project to take leadership over, and after it was completed, the team member was able to write a follow-up paragraph to get visibility. This was a lesson for the manager that it is their role to help their team move up in their career, and that they should work for the team instead of the other way around.

Improving at One-on-ones

After being promoted to team lead, an introvert struggled to lead one-on-one meetings. Initially, the conversations were always technical, but after reflecting on a disagreement with the team, the lead decided to be more direct and focus on personal topics. This allowed them to gain insight into the team's health and address issues before they became bigger problems.

Establishing Credibility In A New Team

When starting as Director of Engineering at Datadog, the author had to quickly learn the systems and architecture of the company. To do this, they set up the environment locally, read development guides and wiki pages, read code, and looked at monitors and errors. They also took a personal approach by setting up one-on-ones to get to know the team and understand what motivated them. The author learned that it is important to get to know the people working for you as well as the code.

Cross-Team Project Cooperation

Cross-team projects can be difficult to manage, but by assigning specific tasks to people on both teams, allowing them to make decisions, and trusting engineers to do the right thing, projects can be successful. Clear goals should be set from the start and ownership should be established to ensure the project is a priority.

From BFF To Boss

When the author was promoted to team lead at Buzzfeed, they had to learn how to manage people who had previously been their peers. They realized they needed to be direct and transparent about the change in their relationship, and to understand what motivated their engineers. Through this process, they learned how to make the right decisions to maintain positive relationships with their team.

How I Reduced Silos And Increased Team Productivity

When the author took over WorldGaming in 2015, the team was siloed and process-driven. The author restructured the team, growing it to 26 people, and implemented a self-managing (holacrazy) team. This approach was successful, with the team launching 14 major features and pushing to production 100 times in a year. However, managing 26 people directly was challenging and time management was crucial. The author learned that if a manager can't manage their own time well, they should not use this model of management, but if they can, it can be very effective.

Building An Engineering Career Ladder

This article discusses the process of creating a career ladder for engineers in a growing company. It outlines the steps taken to understand what creates value for the business, to talk to managers and individual contributors to understand what traits they look for, and to look at other companies to provide a framework for the rubric. It also emphasizes the importance of involving everyone in the process and investing early to get it right.

More Methodical, More Efficient

A software engineer working on an email system encountered a bug that they couldn't fix. Their manager taught them to look at the source code to understand the technology and the bug, rather than just trying to guess solutions. This was a valuable lesson in patience and understanding, which the engineer was able to pass on to their own engineers.

Starting and growing a team in a new city

When expanding a business to a new city, it is important to ensure that the culture of the original office is honored. This can be done by visiting the main office regularly, having explicit conversations about the company culture, and creating virtual company meetings to maintain the connection between offices. It is also important to be aware of the potential for "echo chambers" of subjective realities, and to encourage open communication between offices to avoid any issues.

Gaining the trust of non-technical leaders

Leaders often fail due to a lack of empathy and active listening, which can be difficult to teach. To address this, organizations should focus on a user-centered design approach and leaders should focus on actively listening and repeating what they hear. This will help build trust and understanding between leaders and their teams.

Going from no testing to full QA automation

As an engineering team grows, it is important to maintain a QA-to-engineering ratio to ensure that there is always a third party testing the code. Manual testing is a great way to start, but automation is key to catching bugs quickly. Regressions must be treated with high priority to maintain user trust.

Being an engaging speaker and presenter

As an engineering manager, it can be difficult to engage employees in topics that may be uninteresting to them. To overcome this, one can use a "method acting" approach to emotionally connect to the material, as well as "acting hacks" such as pregnant pauses, volume levels, humor, and eye contact. Additionally, being vulnerable with the audience can help to generate trust and focus.

Managing toxic employees and atmospheres

This article discusses the problem of hiring false positives and false negatives, and the actions taken to address two toxic employees. In the first case, swift and constructive feedback was given, and the employee was eventually let go. In the second case, the employee was talented but slow, and it was necessary to let them go in order to unblock other employees and the organization. The lesson learned is to listen to gut feelings and act swiftly when an environment feels toxic, even if it means taking on legal risk.

Resolving severe personality conflicts

Through personal therapy and psychology training, I have developed a set of techniques to help address personality conflicts between two individuals. By facilitating 1-on-1s with a third party present, the technique encourages each person to speak openly and be heard. This has been successful in transforming relationships, and has led to me being called the "Chief Therapy Officer" at my company. The lesson learned is that organizations can survive with dysfunctions, but those that can have employees listening to each other with empathy until they are truly heard are more likely to function without excessive bureaucracy.

Peacefully managing out low-performing employees

Firing people is a difficult and potentially legally risky task for managers. To ensure the process is done well, managers should have regular 1-on-1s with employees to discuss performance and create a Success Plan with clear goals. If an employee is not happy, managers should have an open conversation to identify what would make them happy, even if it's not in their current role. Quarterly performance reviews should also be held to record detailed information on performance.

Growing and mentoring managers of managers

This article discusses how to combat the perception that management is the only path of growth for engineers. It suggests proactively communicating that there are two separate tracks, both of which are equally respected and deserving of the same levels of compensation and seniority. Additionally, it suggests having mentorship and lead positions, management training options, and enabling autonomy and trust by not having "skip level" 1-on-1's. Finally, it suggests having managers of managers audit their teams and engage with those affected by the team's work.

Enabling a Pro-Diversity Culture

In order to create a pro-diversity culture, it is important for the executive team to be vocal and open about their stance. This requires individuals to bring their whole selves to work and be open about their unique backgrounds. Additionally, trainings should be embraced as a way to educate employees about unconscious bias and microaggressions. By practicing empathy and taking these issues seriously, organizations can create a diverse and safe environment for all employees.

Measuring & Communicating Team Success

In order to measure the success of the Product and Engineering organization, a "Monthly Report" was created to provide measurable data and qualitative content to the executive team and CEO. This report includes an executive summary, highlights and goals, capital expenses, performance & uptime, product development & quality, and visual charts and graphs. This report has been a great way to communicate progress and keep on top of what is going well or not well with the team.

A Delegation Disaster

While working as a Director of Infrastructure Security Consulting, the author delegated authority to one of the consultants on the team while they were away on a 7-hour flight. When they returned, the project was in disarray and the client was talking about firing them. The author learned that while they could delegate authority, they could not delegate responsibility and ultimately they were accountable. They gathered the team and explained the situation, taking responsibility and not passing the buck. This instilled confidence in the team and reminded the author to be careful when delegating.

Handling Stressful Situations

In a high-stress security incident, a consultant was able to help the team leader by providing a plan and delegating tasks. This helped to reduce stress and inspire confidence in the leader, showing that projecting confidence and competence is essential when leading a response effort.

Helping Engineers On Their Career Path

This engineering manager held a one-on-one with a team member who felt overlooked for promotions. The manager encouraged the team member to step up and be seen, and developed an official plan for his career path. The manager then gave the team member a challenging project to take leadership over, and after it was completed, the team member was able to write a follow-up paragraph to get visibility. This was a lesson for the manager that it is their role to help their team move up in their career, and that they should work for the team instead of the other way around.

Improving at One-on-ones

After being promoted to team lead, an introvert struggled to lead one-on-one meetings. Initially, the conversations were always technical, but after reflecting on a disagreement with the team, the lead decided to be more direct and focus on personal topics. This allowed them to gain insight into the team's health and address issues before they became bigger problems.

Establishing Credibility In A New Team

When starting as Director of Engineering at Datadog, the author had to quickly learn the systems and architecture of the company. To do this, they set up the environment locally, read development guides and wiki pages, read code, and looked at monitors and errors. They also took a personal approach by setting up one-on-ones to get to know the team and understand what motivated them. The author learned that it is important to get to know the people working for you as well as the code.

Cross-Team Project Cooperation

Cross-team projects can be difficult to manage, but by assigning specific tasks to people on both teams, allowing them to make decisions, and trusting engineers to do the right thing, projects can be successful. Clear goals should be set from the start and ownership should be established to ensure the project is a priority.

From BFF To Boss

When the author was promoted to team lead at Buzzfeed, they had to learn how to manage people who had previously been their peers. They realized they needed to be direct and transparent about the change in their relationship, and to understand what motivated their engineers. Through this process, they learned how to make the right decisions to maintain positive relationships with their team.

How I Reduced Silos And Increased Team Productivity

When the author took over WorldGaming in 2015, the team was siloed and process-driven. The author restructured the team, growing it to 26 people, and implemented a self-managing (holacrazy) team. This approach was successful, with the team launching 14 major features and pushing to production 100 times in a year. However, managing 26 people directly was challenging and time management was crucial. The author learned that if a manager can't manage their own time well, they should not use this model of management, but if they can, it can be very effective.

Building An Engineering Career Ladder

This article discusses the process of creating a career ladder for engineers in a growing company. It outlines the steps taken to understand what creates value for the business, to talk to managers and individual contributors to understand what traits they look for, and to look at other companies to provide a framework for the rubric. It also emphasizes the importance of involving everyone in the process and investing early to get it right.

More Methodical, More Efficient

A software engineer working on an email system encountered a bug that they couldn't fix. Their manager taught them to look at the source code to understand the technology and the bug, rather than just trying to guess solutions. This was a valuable lesson in patience and understanding, which the engineer was able to pass on to their own engineers.

Starting and growing a team in a new city

When expanding a business to a new city, it is important to ensure that the culture of the original office is honored. This can be done by visiting the main office regularly, having explicit conversations about the company culture, and creating virtual company meetings to maintain the connection between offices. It is also important to be aware of the potential for "echo chambers" of subjective realities, and to encourage open communication between offices to avoid any issues.

Gaining the trust of non-technical leaders

Leaders often fail due to a lack of empathy and active listening, which can be difficult to teach. To address this, organizations should focus on a user-centered design approach and leaders should focus on actively listening and repeating what they hear. This will help build trust and understanding between leaders and their teams.

Going from no testing to full QA automation

As an engineering team grows, it is important to maintain a QA-to-engineering ratio to ensure that there is always a third party testing the code. Manual testing is a great way to start, but automation is key to catching bugs quickly. Regressions must be treated with high priority to maintain user trust.

Being an engaging speaker and presenter

As an engineering manager, it can be difficult to engage employees in topics that may be uninteresting to them. To overcome this, one can use a "method acting" approach to emotionally connect to the material, as well as "acting hacks" such as pregnant pauses, volume levels, humor, and eye contact. Additionally, being vulnerable with the audience can help to generate trust and focus.

Managing toxic employees and atmospheres

This article discusses the problem of hiring false positives and false negatives, and the actions taken to address two toxic employees. In the first case, swift and constructive feedback was given, and the employee was eventually let go. In the second case, the employee was talented but slow, and it was necessary to let them go in order to unblock other employees and the organization. The lesson learned is to listen to gut feelings and act swiftly when an environment feels toxic, even if it means taking on legal risk.

Resolving severe personality conflicts

Through personal therapy and psychology training, I have developed a set of techniques to help address personality conflicts between two individuals. By facilitating 1-on-1s with a third party present, the technique encourages each person to speak openly and be heard. This has been successful in transforming relationships, and has led to me being called the "Chief Therapy Officer" at my company. The lesson learned is that organizations can survive with dysfunctions, but those that can have employees listening to each other with empathy until they are truly heard are more likely to function without excessive bureaucracy.

Peacefully managing out low-performing employees

Firing people is a difficult and potentially legally risky task for managers. To ensure the process is done well, managers should have regular 1-on-1s with employees to discuss performance and create a Success Plan with clear goals. If an employee is not happy, managers should have an open conversation to identify what would make them happy, even if it's not in their current role. Quarterly performance reviews should also be held to record detailed information on performance.

Growing and mentoring managers of managers

This article discusses how to combat the perception that management is the only path of growth for engineers. It suggests proactively communicating that there are two separate tracks, both of which are equally respected and deserving of the same levels of compensation and seniority. Additionally, it suggests having mentorship and lead positions, management training options, and enabling autonomy and trust by not having "skip level" 1-on-1's. Finally, it suggests having managers of managers audit their teams and engage with those affected by the team's work.

Enabling a Pro-Diversity Culture

In order to create a pro-diversity culture, it is important for the executive team to be vocal and open about their stance. This requires individuals to bring their whole selves to work and be open about their unique backgrounds. Additionally, trainings should be embraced as a way to educate employees about unconscious bias and microaggressions. By practicing empathy and taking these issues seriously, organizations can create a diverse and safe environment for all employees.

Measuring & Communicating Team Success

In order to measure the success of the Product and Engineering organization, a "Monthly Report" was created to provide measurable data and qualitative content to the executive team and CEO. This report includes an executive summary, highlights and goals, capital expenses, performance & uptime, product development & quality, and visual charts and graphs. This report has been a great way to communicate progress and keep on top of what is going well or not well with the team.

A Delegation Disaster

While working as a Director of Infrastructure Security Consulting, the author delegated authority to one of the consultants on the team while they were away on a 7-hour flight. When they returned, the project was in disarray and the client was talking about firing them. The author learned that while they could delegate authority, they could not delegate responsibility and ultimately they were accountable. They gathered the team and explained the situation, taking responsibility and not passing the buck. This instilled confidence in the team and reminded the author to be careful when delegating.

Handling Stressful Situations

In a high-stress security incident, a consultant was able to help the team leader by providing a plan and delegating tasks. This helped to reduce stress and inspire confidence in the leader, showing that projecting confidence and competence is essential when leading a response effort.

Helping Engineers On Their Career Path

This engineering manager held a one-on-one with a team member who felt overlooked for promotions. The manager encouraged the team member to step up and be seen, and developed an official plan for his career path. The manager then gave the team member a challenging project to take leadership over, and after it was completed, the team member was able to write a follow-up paragraph to get visibility. This was a lesson for the manager that it is their role to help their team move up in their career, and that they should work for the team instead of the other way around.

Improving at One-on-ones

After being promoted to team lead, an introvert struggled to lead one-on-one meetings. Initially, the conversations were always technical, but after reflecting on a disagreement with the team, the lead decided to be more direct and focus on personal topics. This allowed them to gain insight into the team's health and address issues before they became bigger problems.

Establishing Credibility In A New Team

When starting as Director of Engineering at Datadog, the author had to quickly learn the systems and architecture of the company. To do this, they set up the environment locally, read development guides and wiki pages, read code, and looked at monitors and errors. They also took a personal approach by setting up one-on-ones to get to know the team and understand what motivated them. The author learned that it is important to get to know the people working for you as well as the code.

Cross-Team Project Cooperation

Cross-team projects can be difficult to manage, but by assigning specific tasks to people on both teams, allowing them to make decisions, and trusting engineers to do the right thing, projects can be successful. Clear goals should be set from the start and ownership should be established to ensure the project is a priority.

From BFF To Boss

When the author was promoted to team lead at Buzzfeed, they had to learn how to manage people who had previously been their peers. They realized they needed to be direct and transparent about the change in their relationship, and to understand what motivated their engineers. Through this process, they learned how to make the right decisions to maintain positive relationships with their team.

How I Reduced Silos And Increased Team Productivity

When the author took over WorldGaming in 2015, the team was siloed and process-driven. The author restructured the team, growing it to 26 people, and implemented a self-managing (holacrazy) team. This approach was successful, with the team launching 14 major features and pushing to production 100 times in a year. However, managing 26 people directly was challenging and time management was crucial. The author learned that if a manager can't manage their own time well, they should not use this model of management, but if they can, it can be very effective.

Building An Engineering Career Ladder

This article discusses the process of creating a career ladder for engineers in a growing company. It outlines the steps taken to understand what creates value for the business, to talk to managers and individual contributors to understand what traits they look for, and to look at other companies to provide a framework for the rubric. It also emphasizes the importance of involving everyone in the process and investing early to get it right.

More Methodical, More Efficient

A software engineer working on an email system encountered a bug that they couldn't fix. Their manager taught them to look at the source code to understand the technology and the bug, rather than just trying to guess solutions. This was a valuable lesson in patience and understanding, which the engineer was able to pass on to their own engineers.

Starting and growing a team in a new city

When expanding a business to a new city, it is important to ensure that the culture of the original office is honored. This can be done by visiting the main office regularly, having explicit conversations about the company culture, and creating virtual company meetings to maintain the connection between offices. It is also important to be aware of the potential for "echo chambers" of subjective realities, and to encourage open communication between offices to avoid any issues.

Gaining the trust of non-technical leaders

Leaders often fail due to a lack of empathy and active listening, which can be difficult to teach. To address this, organizations should focus on a user-centered design approach and leaders should focus on actively listening and repeating what they hear. This will help build trust and understanding between leaders and their teams.

Going from no testing to full QA automation

As an engineering team grows, it is important to maintain a QA-to-engineering ratio to ensure that there is always a third party testing the code. Manual testing is a great way to start, but automation is key to catching bugs quickly. Regressions must be treated with high priority to maintain user trust.

Being an engaging speaker and presenter

As an engineering manager, it can be difficult to engage employees in topics that may be uninteresting to them. To overcome this, one can use a "method acting" approach to emotionally connect to the material, as well as "acting hacks" such as pregnant pauses, volume levels, humor, and eye contact. Additionally, being vulnerable with the audience can help to generate trust and focus.

Managing toxic employees and atmospheres

This article discusses the problem of hiring false positives and false negatives, and the actions taken to address two toxic employees. In the first case, swift and constructive feedback was given, and the employee was eventually let go. In the second case, the employee was talented but slow, and it was necessary to let them go in order to unblock other employees and the organization. The lesson learned is to listen to gut feelings and act swiftly when an environment feels toxic, even if it means taking on legal risk.

Resolving severe personality conflicts

Through personal therapy and psychology training, I have developed a set of techniques to help address personality conflicts between two individuals. By facilitating 1-on-1s with a third party present, the technique encourages each person to speak openly and be heard. This has been successful in transforming relationships, and has led to me being called the "Chief Therapy Officer" at my company. The lesson learned is that organizations can survive with dysfunctions, but those that can have employees listening to each other with empathy until they are truly heard are more likely to function without excessive bureaucracy.

Peacefully managing out low-performing employees

Firing people is a difficult and potentially legally risky task for managers. To ensure the process is done well, managers should have regular 1-on-1s with employees to discuss performance and create a Success Plan with clear goals. If an employee is not happy, managers should have an open conversation to identify what would make them happy, even if it's not in their current role. Quarterly performance reviews should also be held to record detailed information on performance.

Growing and mentoring managers of managers

This article discusses how to combat the perception that management is the only path of growth for engineers. It suggests proactively communicating that there are two separate tracks, both of which are equally respected and deserving of the same levels of compensation and seniority. Additionally, it suggests having mentorship and lead positions, management training options, and enabling autonomy and trust by not having "skip level" 1-on-1's. Finally, it suggests having managers of managers audit their teams and engage with those affected by the team's work.

Enabling a Pro-Diversity Culture

In order to create a pro-diversity culture, it is important for the executive team to be vocal and open about their stance. This requires individuals to bring their whole selves to work and be open about their unique backgrounds. Additionally, trainings should be embraced as a way to educate employees about unconscious bias and microaggressions. By practicing empathy and taking these issues seriously, organizations can create a diverse and safe environment for all employees.

Measuring & Communicating Team Success

In order to measure the success of the Product and Engineering organization, a "Monthly Report" was created to provide measurable data and qualitative content to the executive team and CEO. This report includes an executive summary, highlights and goals, capital expenses, performance & uptime, product development & quality, and visual charts and graphs. This report has been a great way to communicate progress and keep on top of what is going well or not well with the team.

A Delegation Disaster

While working as a Director of Infrastructure Security Consulting, the author delegated authority to one of the consultants on the team while they were away on a 7-hour flight. When they returned, the project was in disarray and the client was talking about firing them. The author learned that while they could delegate authority, they could not delegate responsibility and ultimately they were accountable. They gathered the team and explained the situation, taking responsibility and not passing the buck. This instilled confidence in the team and reminded the author to be careful when delegating.

Handling Stressful Situations

In a high-stress security incident, a consultant was able to help the team leader by providing a plan and delegating tasks. This helped to reduce stress and inspire confidence in the leader, showing that projecting confidence and competence is essential when leading a response effort.

Helping Engineers On Their Career Path

This engineering manager held a one-on-one with a team member who felt overlooked for promotions. The manager encouraged the team member to step up and be seen, and developed an official plan for his career path. The manager then gave the team member a challenging project to take leadership over, and after it was completed, the team member was able to write a follow-up paragraph to get visibility. This was a lesson for the manager that it is their role to help their team move up in their career, and that they should work for the team instead of the other way around.

Improving at One-on-ones

After being promoted to team lead, an introvert struggled to lead one-on-one meetings. Initially, the conversations were always technical, but after reflecting on a disagreement with the team, the lead decided to be more direct and focus on personal topics. This allowed them to gain insight into the team's health and address issues before they became bigger problems.

Establishing Credibility In A New Team

When starting as Director of Engineering at Datadog, the author had to quickly learn the systems and architecture of the company. To do this, they set up the environment locally, read development guides and wiki pages, read code, and looked at monitors and errors. They also took a personal approach by setting up one-on-ones to get to know the team and understand what motivated them. The author learned that it is important to get to know the people working for you as well as the code.

Cross-Team Project Cooperation

Cross-team projects can be difficult to manage, but by assigning specific tasks to people on both teams, allowing them to make decisions, and trusting engineers to do the right thing, projects can be successful. Clear goals should be set from the start and ownership should be established to ensure the project is a priority.

From BFF To Boss

When the author was promoted to team lead at Buzzfeed, they had to learn how to manage people who had previously been their peers. They realized they needed to be direct and transparent about the change in their relationship, and to understand what motivated their engineers. Through this process, they learned how to make the right decisions to maintain positive relationships with their team.

How I Reduced Silos And Increased Team Productivity

When the author took over WorldGaming in 2015, the team was siloed and process-driven. The author restructured the team, growing it to 26 people, and implemented a self-managing (holacrazy) team. This approach was successful, with the team launching 14 major features and pushing to production 100 times in a year. However, managing 26 people directly was challenging and time management was crucial. The author learned that if a manager can't manage their own time well, they should not use this model of management, but if they can, it can be very effective.

Building An Engineering Career Ladder

This article discusses the process of creating a career ladder for engineers in a growing company. It outlines the steps taken to understand what creates value for the business, to talk to managers and individual contributors to understand what traits they look for, and to look at other companies to provide a framework for the rubric. It also emphasizes the importance of involving everyone in the process and investing early to get it right.

More Methodical, More Efficient

A software engineer working on an email system encountered a bug that they couldn't fix. Their manager taught them to look at the source code to understand the technology and the bug, rather than just trying to guess solutions. This was a valuable lesson in patience and understanding, which the engineer was able to pass on to their own engineers.

Starting and growing a team in a new city

When expanding a business to a new city, it is important to ensure that the culture of the original office is honored. This can be done by visiting the main office regularly, having explicit conversations about the company culture, and creating virtual company meetings to maintain the connection between offices. It is also important to be aware of the potential for "echo chambers" of subjective realities, and to encourage open communication between offices to avoid any issues.

Gaining the trust of non-technical leaders

Leaders often fail due to a lack of empathy and active listening, which can be difficult to teach. To address this, organizations should focus on a user-centered design approach and leaders should focus on actively listening and repeating what they hear. This will help build trust and understanding between leaders and their teams.

Going from no testing to full QA automation

As an engineering team grows, it is important to maintain a QA-to-engineering ratio to ensure that there is always a third party testing the code. Manual testing is a great way to start, but automation is key to catching bugs quickly. Regressions must be treated with high priority to maintain user trust.

Being an engaging speaker and presenter

As an engineering manager, it can be difficult to engage employees in topics that may be uninteresting to them. To overcome this, one can use a "method acting" approach to emotionally connect to the material, as well as "acting hacks" such as pregnant pauses, volume levels, humor, and eye contact. Additionally, being vulnerable with the audience can help to generate trust and focus.

Managing toxic employees and atmospheres

This article discusses the problem of hiring false positives and false negatives, and the actions taken to address two toxic employees. In the first case, swift and constructive feedback was given, and the employee was eventually let go. In the second case, the employee was talented but slow, and it was necessary to let them go in order to unblock other employees and the organization. The lesson learned is to listen to gut feelings and act swiftly when an environment feels toxic, even if it means taking on legal risk.

Resolving severe personality conflicts

Through personal therapy and psychology training, I have developed a set of techniques to help address personality conflicts between two individuals. By facilitating 1-on-1s with a third party present, the technique encourages each person to speak openly and be heard. This has been successful in transforming relationships, and has led to me being called the "Chief Therapy Officer" at my company. The lesson learned is that organizations can survive with dysfunctions, but those that can have employees listening to each other with empathy until they are truly heard are more likely to function without excessive bureaucracy.

Peacefully managing out low-performing employees

Firing people is a difficult and potentially legally risky task for managers. To ensure the process is done well, managers should have regular 1-on-1s with employees to discuss performance and create a Success Plan with clear goals. If an employee is not happy, managers should have an open conversation to identify what would make them happy, even if it's not in their current role. Quarterly performance reviews should also be held to record detailed information on performance.

Growing and mentoring managers of managers

This article discusses how to combat the perception that management is the only path of growth for engineers. It suggests proactively communicating that there are two separate tracks, both of which are equally respected and deserving of the same levels of compensation and seniority. Additionally, it suggests having mentorship and lead positions, management training options, and enabling autonomy and trust by not having "skip level" 1-on-1's. Finally, it suggests having managers of managers audit their teams and engage with those affected by the team's work.

Enabling a Pro-Diversity Culture

In order to create a pro-diversity culture, it is important for the executive team to be vocal and open about their stance. This requires individuals to bring their whole selves to work and be open about their unique backgrounds. Additionally, trainings should be embraced as a way to educate employees about unconscious bias and microaggressions. By practicing empathy and taking these issues seriously, organizations can create a diverse and safe environment for all employees.

Measuring & Communicating Team Success

In order to measure the success of the Product and Engineering organization, a "Monthly Report" was created to provide measurable data and qualitative content to the executive team and CEO. This report includes an executive summary, highlights and goals, capital expenses, performance & uptime, product development & quality, and visual charts and graphs. This report has been a great way to communicate progress and keep on top of what is going well or not well with the team.

A Delegation Disaster

While working as a Director of Infrastructure Security Consulting, the author delegated authority to one of the consultants on the team while they were away on a 7-hour flight. When they returned, the project was in disarray and the client was talking about firing them. The author learned that while they could delegate authority, they could not delegate responsibility and ultimately they were accountable. They gathered the team and explained the situation, taking responsibility and not passing the buck. This instilled confidence in the team and reminded the author to be careful when delegating.

Handling Stressful Situations

In a high-stress security incident, a consultant was able to help the team leader by providing a plan and delegating tasks. This helped to reduce stress and inspire confidence in the leader, showing that projecting confidence and competence is essential when leading a response effort.

Helping Engineers On Their Career Path

This engineering manager held a one-on-one with a team member who felt overlooked for promotions. The manager encouraged the team member to step up and be seen, and developed an official plan for his career path. The manager then gave the team member a challenging project to take leadership over, and after it was completed, the team member was able to write a follow-up paragraph to get visibility. This was a lesson for the manager that it is their role to help their team move up in their career, and that they should work for the team instead of the other way around.

Improving at One-on-ones

After being promoted to team lead, an introvert struggled to lead one-on-one meetings. Initially, the conversations were always technical, but after reflecting on a disagreement with the team, the lead decided to be more direct and focus on personal topics. This allowed them to gain insight into the team's health and address issues before they became bigger problems.

Establishing Credibility In A New Team

When starting as Director of Engineering at Datadog, the author had to quickly learn the systems and architecture of the company. To do this, they set up the environment locally, read development guides and wiki pages, read code, and looked at monitors and errors. They also took a personal approach by setting up one-on-ones to get to know the team and understand what motivated them. The author learned that it is important to get to know the people working for you as well as the code.

Cross-Team Project Cooperation

Cross-team projects can be difficult to manage, but by assigning specific tasks to people on both teams, allowing them to make decisions, and trusting engineers to do the right thing, projects can be successful. Clear goals should be set from the start and ownership should be established to ensure the project is a priority.

From BFF To Boss

When the author was promoted to team lead at Buzzfeed, they had to learn how to manage people who had previously been their peers. They realized they needed to be direct and transparent about the change in their relationship, and to understand what motivated their engineers. Through this process, they learned how to make the right decisions to maintain positive relationships with their team.

How I Reduced Silos And Increased Team Productivity

When the author took over WorldGaming in 2015, the team was siloed and process-driven. The author restructured the team, growing it to 26 people, and implemented a self-managing (holacrazy) team. This approach was successful, with the team launching 14 major features and pushing to production 100 times in a year. However, managing 26 people directly was challenging and time management was crucial. The author learned that if a manager can't manage their own time well, they should not use this model of management, but if they can, it can be very effective.

Building An Engineering Career Ladder

This article discusses the process of creating a career ladder for engineers in a growing company. It outlines the steps taken to understand what creates value for the business, to talk to managers and individual contributors to understand what traits they look for, and to look at other companies to provide a framework for the rubric. It also emphasizes the importance of involving everyone in the process and investing early to get it right.

More Methodical, More Efficient

A software engineer working on an email system encountered a bug that they couldn't fix. Their manager taught them to look at the source code to understand the technology and the bug, rather than just trying to guess solutions. This was a valuable lesson in patience and understanding, which the engineer was able to pass on to their own engineers.

Starting and growing a team in a new city

When expanding a business to a new city, it is important to ensure that the culture of the original office is honored. This can be done by visiting the main office regularly, having explicit conversations about the company culture, and creating virtual company meetings to maintain the connection between offices. It is also important to be aware of the potential for "echo chambers" of subjective realities, and to encourage open communication between offices to avoid any issues.

Gaining the trust of non-technical leaders

Leaders often fail due to a lack of empathy and active listening, which can be difficult to teach. To address this, organizations should focus on a user-centered design approach and leaders should focus on actively listening and repeating what they hear. This will help build trust and understanding between leaders and their teams.

Going from no testing to full QA automation

As an engineering team grows, it is important to maintain a QA-to-engineering ratio to ensure that there is always a third party testing the code. Manual testing is a great way to start, but automation is key to catching bugs quickly. Regressions must be treated with high priority to maintain user trust.

Being an engaging speaker and presenter

As an engineering manager, it can be difficult to engage employees in topics that may be uninteresting to them. To overcome this, one can use a "method acting" approach to emotionally connect to the material, as well as "acting hacks" such as pregnant pauses, volume levels, humor, and eye contact. Additionally, being vulnerable with the audience can help to generate trust and focus.

Managing toxic employees and atmospheres

This article discusses the problem of hiring false positives and false negatives, and the actions taken to address two toxic employees. In the first case, swift and constructive feedback was given, and the employee was eventually let go. In the second case, the employee was talented but slow, and it was necessary to let them go in order to unblock other employees and the organization. The lesson learned is to listen to gut feelings and act swiftly when an environment feels toxic, even if it means taking on legal risk.

Resolving severe personality conflicts

Through personal therapy and psychology training, I have developed a set of techniques to help address personality conflicts between two individuals. By facilitating 1-on-1s with a third party present, the technique encourages each person to speak openly and be heard. This has been successful in transforming relationships, and has led to me being called the "Chief Therapy Officer" at my company. The lesson learned is that organizations can survive with dysfunctions, but those that can have employees listening to each other with empathy until they are truly heard are more likely to function without excessive bureaucracy.

Peacefully managing out low-performing employees

Firing people is a difficult and potentially legally risky task for managers. To ensure the process is done well, managers should have regular 1-on-1s with employees to discuss performance and create a Success Plan with clear goals. If an employee is not happy, managers should have an open conversation to identify what would make them happy, even if it's not in their current role. Quarterly performance reviews should also be held to record detailed information on performance.

Growing and mentoring managers of managers

This article discusses how to combat the perception that management is the only path of growth for engineers. It suggests proactively communicating that there are two separate tracks, both of which are equally respected and deserving of the same levels of compensation and seniority. Additionally, it suggests having mentorship and lead positions, management training options, and enabling autonomy and trust by not having "skip level" 1-on-1's. Finally, it suggests having managers of managers audit their teams and engage with those affected by the team's work.

Enabling a Pro-Diversity Culture

In order to create a pro-diversity culture, it is important for the executive team to be vocal and open about their stance. This requires individuals to bring their whole selves to work and be open about their unique backgrounds. Additionally, trainings should be embraced as a way to educate employees about unconscious bias and microaggressions. By practicing empathy and taking these issues seriously, organizations can create a diverse and safe environment for all employees.

Measuring & Communicating Team Success

In order to measure the success of the Product and Engineering organization, a "Monthly Report" was created to provide measurable data and qualitative content to the executive team and CEO. This report includes an executive summary, highlights and goals, capital expenses, performance & uptime, product development & quality, and visual charts and graphs. This report has been a great way to communicate progress and keep on top of what is going well or not well with the team.