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What to take into account when choosing between technical debt and new features

Technical debt can be difficult to manage, and it can be hard to decide when to prioritize it. A team faced with the challenge of managing technical debt while also building new features found that they were unable to do either. This caused stability and scalability issues, and the team had to focus on firefighting instead of being proactive. The lesson learned is that technical debt should be prioritized, and it is important to consider the specific situation when making decisions.

How to scale a company?

Stripe's rapid growth led to an organizational structure that was no longer suitable, resulting in unclear ownership of projects, delayed work, and a lack of clear boundaries for each employee's tasks. To adapt to this growth, changes were implemented, but they started to irritate people. To remedy this, the focus was shifted to talking to people and gathering feedback, while preparing future managers for their positions. It is important to keep in mind that the organizational structure of a startup has to change as the company grows, and that the most important thing is to implement the process smoothly and to involve people in the changes.

Transitioning to dedicated agile coaches (scrum masters)

When the engineering team at a previous company grew to 35+ engineers, they encountered issues with agile coaching. To solve this, they decided to hire a freelance scrum master for a trial period, and then hired a full-time agile coach. This proved to be successful, and the team of agile coaches grew to five people. Benefits of having an in-house team of agile coaches include having experts who can own the process, having someone with team performance and improving methodology as their main metric and objective, and having no hierarchical relationship between scrum masters and EMs.

How to implement new work processes in a tech team?

When transitioning to a managerial role, the author found it necessary to introduce new processes and tools to optimize workloads and communication within the team. To ensure successful implementation of status reports, the author looked for well-designed tools, communicated the need for the process, and made sure the team felt they were part of the decision-making process. This ultimately resulted in a successful implementation of the status reports.

I helped a direct report get out of “Hero” mode

A "Hero" employee was struggling to get out of their default mode of solving any problem that arose. The manager took action by offering the employee opportunities to grow and fill the space left by them moving to a new team with new hires and training. The lesson learned was that most "Heroes" end up in these situations due to bad onboarding and insufficient training, and it is the manager's role to guide them out of it.

Handling someone who ignores company policies

When employees ignore company policies, the most effective way to handle the situation is to point it out directly. Coaching employees is not helpful and could be counterproductive. Before deciding on how to handle a problem with an employee, determine if it is a mindset or skill set problem.

How to detect a potential problem within your team

During a one-on-one, a direct report expressed concern that some people were not aware of the time requirements associated with a process. After further investigation, it was found that the problem was due to one person not being prompt in responding to others. To solve the problem, clearer, quantitative language was used to match everyone's expectations. This experience taught the importance of being alert during one-on-ones, digging deeper if there is a sense of frustration, and watching out for patterns in stories across time.

How to encourage people to make the most of retrospectives

A senior engineer on a team was initially skeptical of the value of sprint retrospectives, but eventually came to understand their importance. It is important to listen to team members, create a safe space for them to share, and be flexible and adjust when necessary. There are lots of activities available to help identify areas of improvement in retrospectives.

The Push to Production Process Not Respected

When errors were occurring during the push to production process, a checklist was created to help the developers. However, people started to bypass the checklist, so an "production push algorithm" was created instead. This algorithm was more explicit and efficient, and now it is used for tasks beyond just development.

How to handle tension caused by cultural differences

A team split between Buenos Aires and Dallas had a negative impression of an engineer in Dallas due to his lack of knowledge of industry standards and his direct, even mean, attitude towards the Argentinian engineers. After discussing cultural differences, the engineer changed his behavior and the team was able to work together. It is important to set expectations for different cultures to interact and to discuss cultural differences in order to prevent misunderstandings.

What to do with an employee who wants to step-up

A good engineer was interested in becoming a senior engineer, so the manager discussed the criteria for promotion with him line-by-line. They had several follow-up conversations and the manager made it clear that the promotion was up to the employee's work. This showed the importance of setting clear expectations when promoting an employee.

How I improved at giving negative feedback

This article discusses the importance of giving negative feedback, even to people you care about. It suggests starting with your top performers and emphasizes that feedback is a gift. It also highlights the importance of giving feedback early on, rather than waiting until someone is on a performance plan and in line to be dismissed.

I took too much time trying to detect the origin of a problem

When a new manager arrived in a team, they noticed that the tech lead was more concerned with political matters than the quality of the code shipped. After a long process of trying to help the tech lead boost their performance, they had to be let go. The manager learned that it was important to build a genuine relationship with the team to understand where problems are coming from.

Adjusting Best Practices as a Company Grows

The engineering manager at Blablacar held a weekly meeting with the engineering team, but as the team grew, the value of the meeting was not appreciated and it was eventually stopped. The author learned that when leading a meeting with a large team, it is better to suggest solutions rather than ask for them.

Coaching a recently hired engineer on their areas of improvement

A manager arrived to a team of high performers and noticed that one junior employee was not fitting in with the company culture. The manager took action by creating a relationship of trust and setting clear goals and expectations for the employee. Through coaching and setting measurable paths, the employee has improved in collaboration, accountability, and quality of work. The manager learned that it is important to help young employees work in an open and trusted environment, and to have career discussions on an ongoing basis.

Be agile in your processes

Scrum is the most popular agile software development methodology, but it is important to consider if it is the right approach for the product being built. Flexibility is key, as sprint duration, start and end times, and retrospectives should be tailored to the team and the business. Two-week sprints are a good compromise between too much time between projects and too much time spent in meetings. Mid-week sprint starts are preferable to avoid holidays and keep people energized. Sprint reviews should be used to adjust the product, and retrospectives to adjust the process.

The first time you have to let go of someone

A manager was faced with the difficult task of firing an underperforming employee. With the help of their manager and former manager, they were able to handle the situation and fire the employee. The manager learned the importance of being determined and giving constructive feedback before firing someone.

A team member struggling with working remotely

A team of engineers was managed remotely, and one member was performing poorly and inconsistently. After providing direct feedback and learning that it was her first remote job, the manager was unable to directly fire her and had to get authorization. Ultimately, the team member was fired and the manager learned that working remotely is not for everyone and that the team member needed more structure in her life to succeed.

Ensuring all your teams work together as a single unit

In this case study, the author was leading an engineering team that was performing well but felt burned out. After meeting with the leads of the other teams (Product Management, User Experience, Support, QA, Documentation, etc.), the author implemented design sessions that included all relevant teams and organized team lunches to restore trust. As a result, the product was well-received and the documentation was impeccable. The lesson learned is to always involve all teams in the organization, as each team has something to contribute.

The Importance of Gathering Honest Feedback

A co-founder of Box had difficulty with a back-end engineering manager and eventually decided to let him go. However, the day after, a bunch of back-end engineers were going to quit due to the co-founder's actions. To understand why, the co-founder sat down with each of the engineers and heard from lots of different people who said that they didn't like the job that he was doing. He realized that he had failed to be cognizant of the power dynamic between himself and the new engineers and hired a coach to get feedback on his performance. He worked hard to make improvements in his areas of weakness and started proactively asking for feedback. He learned that his title and status in the company can inhibit people from providing him with feedback and that he must be proactive in reaching out for it.

What to take into account when choosing between technical debt and new features

Technical debt can be difficult to manage, and it can be hard to decide when to prioritize it. A team faced with the challenge of managing technical debt while also building new features found that they were unable to do either. This caused stability and scalability issues, and the team had to focus on firefighting instead of being proactive. The lesson learned is that technical debt should be prioritized, and it is important to consider the specific situation when making decisions.

How to scale a company?

Stripe's rapid growth led to an organizational structure that was no longer suitable, resulting in unclear ownership of projects, delayed work, and a lack of clear boundaries for each employee's tasks. To adapt to this growth, changes were implemented, but they started to irritate people. To remedy this, the focus was shifted to talking to people and gathering feedback, while preparing future managers for their positions. It is important to keep in mind that the organizational structure of a startup has to change as the company grows, and that the most important thing is to implement the process smoothly and to involve people in the changes.

Transitioning to dedicated agile coaches (scrum masters)

When the engineering team at a previous company grew to 35+ engineers, they encountered issues with agile coaching. To solve this, they decided to hire a freelance scrum master for a trial period, and then hired a full-time agile coach. This proved to be successful, and the team of agile coaches grew to five people. Benefits of having an in-house team of agile coaches include having experts who can own the process, having someone with team performance and improving methodology as their main metric and objective, and having no hierarchical relationship between scrum masters and EMs.

How to implement new work processes in a tech team?

When transitioning to a managerial role, the author found it necessary to introduce new processes and tools to optimize workloads and communication within the team. To ensure successful implementation of status reports, the author looked for well-designed tools, communicated the need for the process, and made sure the team felt they were part of the decision-making process. This ultimately resulted in a successful implementation of the status reports.

I helped a direct report get out of “Hero” mode

A "Hero" employee was struggling to get out of their default mode of solving any problem that arose. The manager took action by offering the employee opportunities to grow and fill the space left by them moving to a new team with new hires and training. The lesson learned was that most "Heroes" end up in these situations due to bad onboarding and insufficient training, and it is the manager's role to guide them out of it.

Handling someone who ignores company policies

When employees ignore company policies, the most effective way to handle the situation is to point it out directly. Coaching employees is not helpful and could be counterproductive. Before deciding on how to handle a problem with an employee, determine if it is a mindset or skill set problem.

How to detect a potential problem within your team

During a one-on-one, a direct report expressed concern that some people were not aware of the time requirements associated with a process. After further investigation, it was found that the problem was due to one person not being prompt in responding to others. To solve the problem, clearer, quantitative language was used to match everyone's expectations. This experience taught the importance of being alert during one-on-ones, digging deeper if there is a sense of frustration, and watching out for patterns in stories across time.

How to encourage people to make the most of retrospectives

A senior engineer on a team was initially skeptical of the value of sprint retrospectives, but eventually came to understand their importance. It is important to listen to team members, create a safe space for them to share, and be flexible and adjust when necessary. There are lots of activities available to help identify areas of improvement in retrospectives.

The Push to Production Process Not Respected

When errors were occurring during the push to production process, a checklist was created to help the developers. However, people started to bypass the checklist, so an "production push algorithm" was created instead. This algorithm was more explicit and efficient, and now it is used for tasks beyond just development.

How to handle tension caused by cultural differences

A team split between Buenos Aires and Dallas had a negative impression of an engineer in Dallas due to his lack of knowledge of industry standards and his direct, even mean, attitude towards the Argentinian engineers. After discussing cultural differences, the engineer changed his behavior and the team was able to work together. It is important to set expectations for different cultures to interact and to discuss cultural differences in order to prevent misunderstandings.

What to do with an employee who wants to step-up

A good engineer was interested in becoming a senior engineer, so the manager discussed the criteria for promotion with him line-by-line. They had several follow-up conversations and the manager made it clear that the promotion was up to the employee's work. This showed the importance of setting clear expectations when promoting an employee.

How I improved at giving negative feedback

This article discusses the importance of giving negative feedback, even to people you care about. It suggests starting with your top performers and emphasizes that feedback is a gift. It also highlights the importance of giving feedback early on, rather than waiting until someone is on a performance plan and in line to be dismissed.

I took too much time trying to detect the origin of a problem

When a new manager arrived in a team, they noticed that the tech lead was more concerned with political matters than the quality of the code shipped. After a long process of trying to help the tech lead boost their performance, they had to be let go. The manager learned that it was important to build a genuine relationship with the team to understand where problems are coming from.

Adjusting Best Practices as a Company Grows

The engineering manager at Blablacar held a weekly meeting with the engineering team, but as the team grew, the value of the meeting was not appreciated and it was eventually stopped. The author learned that when leading a meeting with a large team, it is better to suggest solutions rather than ask for them.

Coaching a recently hired engineer on their areas of improvement

A manager arrived to a team of high performers and noticed that one junior employee was not fitting in with the company culture. The manager took action by creating a relationship of trust and setting clear goals and expectations for the employee. Through coaching and setting measurable paths, the employee has improved in collaboration, accountability, and quality of work. The manager learned that it is important to help young employees work in an open and trusted environment, and to have career discussions on an ongoing basis.

Be agile in your processes

Scrum is the most popular agile software development methodology, but it is important to consider if it is the right approach for the product being built. Flexibility is key, as sprint duration, start and end times, and retrospectives should be tailored to the team and the business. Two-week sprints are a good compromise between too much time between projects and too much time spent in meetings. Mid-week sprint starts are preferable to avoid holidays and keep people energized. Sprint reviews should be used to adjust the product, and retrospectives to adjust the process.

The first time you have to let go of someone

A manager was faced with the difficult task of firing an underperforming employee. With the help of their manager and former manager, they were able to handle the situation and fire the employee. The manager learned the importance of being determined and giving constructive feedback before firing someone.

A team member struggling with working remotely

A team of engineers was managed remotely, and one member was performing poorly and inconsistently. After providing direct feedback and learning that it was her first remote job, the manager was unable to directly fire her and had to get authorization. Ultimately, the team member was fired and the manager learned that working remotely is not for everyone and that the team member needed more structure in her life to succeed.

Ensuring all your teams work together as a single unit

In this case study, the author was leading an engineering team that was performing well but felt burned out. After meeting with the leads of the other teams (Product Management, User Experience, Support, QA, Documentation, etc.), the author implemented design sessions that included all relevant teams and organized team lunches to restore trust. As a result, the product was well-received and the documentation was impeccable. The lesson learned is to always involve all teams in the organization, as each team has something to contribute.

The Importance of Gathering Honest Feedback

A co-founder of Box had difficulty with a back-end engineering manager and eventually decided to let him go. However, the day after, a bunch of back-end engineers were going to quit due to the co-founder's actions. To understand why, the co-founder sat down with each of the engineers and heard from lots of different people who said that they didn't like the job that he was doing. He realized that he had failed to be cognizant of the power dynamic between himself and the new engineers and hired a coach to get feedback on his performance. He worked hard to make improvements in his areas of weakness and started proactively asking for feedback. He learned that his title and status in the company can inhibit people from providing him with feedback and that he must be proactive in reaching out for it.

What to take into account when choosing between technical debt and new features

Technical debt can be difficult to manage, and it can be hard to decide when to prioritize it. A team faced with the challenge of managing technical debt while also building new features found that they were unable to do either. This caused stability and scalability issues, and the team had to focus on firefighting instead of being proactive. The lesson learned is that technical debt should be prioritized, and it is important to consider the specific situation when making decisions.

How to scale a company?

Stripe's rapid growth led to an organizational structure that was no longer suitable, resulting in unclear ownership of projects, delayed work, and a lack of clear boundaries for each employee's tasks. To adapt to this growth, changes were implemented, but they started to irritate people. To remedy this, the focus was shifted to talking to people and gathering feedback, while preparing future managers for their positions. It is important to keep in mind that the organizational structure of a startup has to change as the company grows, and that the most important thing is to implement the process smoothly and to involve people in the changes.

Transitioning to dedicated agile coaches (scrum masters)

When the engineering team at a previous company grew to 35+ engineers, they encountered issues with agile coaching. To solve this, they decided to hire a freelance scrum master for a trial period, and then hired a full-time agile coach. This proved to be successful, and the team of agile coaches grew to five people. Benefits of having an in-house team of agile coaches include having experts who can own the process, having someone with team performance and improving methodology as their main metric and objective, and having no hierarchical relationship between scrum masters and EMs.

How to implement new work processes in a tech team?

When transitioning to a managerial role, the author found it necessary to introduce new processes and tools to optimize workloads and communication within the team. To ensure successful implementation of status reports, the author looked for well-designed tools, communicated the need for the process, and made sure the team felt they were part of the decision-making process. This ultimately resulted in a successful implementation of the status reports.

I helped a direct report get out of “Hero” mode

A "Hero" employee was struggling to get out of their default mode of solving any problem that arose. The manager took action by offering the employee opportunities to grow and fill the space left by them moving to a new team with new hires and training. The lesson learned was that most "Heroes" end up in these situations due to bad onboarding and insufficient training, and it is the manager's role to guide them out of it.

Handling someone who ignores company policies

When employees ignore company policies, the most effective way to handle the situation is to point it out directly. Coaching employees is not helpful and could be counterproductive. Before deciding on how to handle a problem with an employee, determine if it is a mindset or skill set problem.

How to detect a potential problem within your team

During a one-on-one, a direct report expressed concern that some people were not aware of the time requirements associated with a process. After further investigation, it was found that the problem was due to one person not being prompt in responding to others. To solve the problem, clearer, quantitative language was used to match everyone's expectations. This experience taught the importance of being alert during one-on-ones, digging deeper if there is a sense of frustration, and watching out for patterns in stories across time.

How to encourage people to make the most of retrospectives

A senior engineer on a team was initially skeptical of the value of sprint retrospectives, but eventually came to understand their importance. It is important to listen to team members, create a safe space for them to share, and be flexible and adjust when necessary. There are lots of activities available to help identify areas of improvement in retrospectives.

The Push to Production Process Not Respected

When errors were occurring during the push to production process, a checklist was created to help the developers. However, people started to bypass the checklist, so an "production push algorithm" was created instead. This algorithm was more explicit and efficient, and now it is used for tasks beyond just development.

How to handle tension caused by cultural differences

A team split between Buenos Aires and Dallas had a negative impression of an engineer in Dallas due to his lack of knowledge of industry standards and his direct, even mean, attitude towards the Argentinian engineers. After discussing cultural differences, the engineer changed his behavior and the team was able to work together. It is important to set expectations for different cultures to interact and to discuss cultural differences in order to prevent misunderstandings.

What to do with an employee who wants to step-up

A good engineer was interested in becoming a senior engineer, so the manager discussed the criteria for promotion with him line-by-line. They had several follow-up conversations and the manager made it clear that the promotion was up to the employee's work. This showed the importance of setting clear expectations when promoting an employee.

How I improved at giving negative feedback

This article discusses the importance of giving negative feedback, even to people you care about. It suggests starting with your top performers and emphasizes that feedback is a gift. It also highlights the importance of giving feedback early on, rather than waiting until someone is on a performance plan and in line to be dismissed.

I took too much time trying to detect the origin of a problem

When a new manager arrived in a team, they noticed that the tech lead was more concerned with political matters than the quality of the code shipped. After a long process of trying to help the tech lead boost their performance, they had to be let go. The manager learned that it was important to build a genuine relationship with the team to understand where problems are coming from.

Adjusting Best Practices as a Company Grows

The engineering manager at Blablacar held a weekly meeting with the engineering team, but as the team grew, the value of the meeting was not appreciated and it was eventually stopped. The author learned that when leading a meeting with a large team, it is better to suggest solutions rather than ask for them.

Coaching a recently hired engineer on their areas of improvement

A manager arrived to a team of high performers and noticed that one junior employee was not fitting in with the company culture. The manager took action by creating a relationship of trust and setting clear goals and expectations for the employee. Through coaching and setting measurable paths, the employee has improved in collaboration, accountability, and quality of work. The manager learned that it is important to help young employees work in an open and trusted environment, and to have career discussions on an ongoing basis.

Be agile in your processes

Scrum is the most popular agile software development methodology, but it is important to consider if it is the right approach for the product being built. Flexibility is key, as sprint duration, start and end times, and retrospectives should be tailored to the team and the business. Two-week sprints are a good compromise between too much time between projects and too much time spent in meetings. Mid-week sprint starts are preferable to avoid holidays and keep people energized. Sprint reviews should be used to adjust the product, and retrospectives to adjust the process.

The first time you have to let go of someone

A manager was faced with the difficult task of firing an underperforming employee. With the help of their manager and former manager, they were able to handle the situation and fire the employee. The manager learned the importance of being determined and giving constructive feedback before firing someone.

A team member struggling with working remotely

A team of engineers was managed remotely, and one member was performing poorly and inconsistently. After providing direct feedback and learning that it was her first remote job, the manager was unable to directly fire her and had to get authorization. Ultimately, the team member was fired and the manager learned that working remotely is not for everyone and that the team member needed more structure in her life to succeed.

Ensuring all your teams work together as a single unit

In this case study, the author was leading an engineering team that was performing well but felt burned out. After meeting with the leads of the other teams (Product Management, User Experience, Support, QA, Documentation, etc.), the author implemented design sessions that included all relevant teams and organized team lunches to restore trust. As a result, the product was well-received and the documentation was impeccable. The lesson learned is to always involve all teams in the organization, as each team has something to contribute.

The Importance of Gathering Honest Feedback

A co-founder of Box had difficulty with a back-end engineering manager and eventually decided to let him go. However, the day after, a bunch of back-end engineers were going to quit due to the co-founder's actions. To understand why, the co-founder sat down with each of the engineers and heard from lots of different people who said that they didn't like the job that he was doing. He realized that he had failed to be cognizant of the power dynamic between himself and the new engineers and hired a coach to get feedback on his performance. He worked hard to make improvements in his areas of weakness and started proactively asking for feedback. He learned that his title and status in the company can inhibit people from providing him with feedback and that he must be proactive in reaching out for it.

What to take into account when choosing between technical debt and new features

Technical debt can be difficult to manage, and it can be hard to decide when to prioritize it. A team faced with the challenge of managing technical debt while also building new features found that they were unable to do either. This caused stability and scalability issues, and the team had to focus on firefighting instead of being proactive. The lesson learned is that technical debt should be prioritized, and it is important to consider the specific situation when making decisions.

How to scale a company?

Stripe's rapid growth led to an organizational structure that was no longer suitable, resulting in unclear ownership of projects, delayed work, and a lack of clear boundaries for each employee's tasks. To adapt to this growth, changes were implemented, but they started to irritate people. To remedy this, the focus was shifted to talking to people and gathering feedback, while preparing future managers for their positions. It is important to keep in mind that the organizational structure of a startup has to change as the company grows, and that the most important thing is to implement the process smoothly and to involve people in the changes.

Transitioning to dedicated agile coaches (scrum masters)

When the engineering team at a previous company grew to 35+ engineers, they encountered issues with agile coaching. To solve this, they decided to hire a freelance scrum master for a trial period, and then hired a full-time agile coach. This proved to be successful, and the team of agile coaches grew to five people. Benefits of having an in-house team of agile coaches include having experts who can own the process, having someone with team performance and improving methodology as their main metric and objective, and having no hierarchical relationship between scrum masters and EMs.

How to implement new work processes in a tech team?

When transitioning to a managerial role, the author found it necessary to introduce new processes and tools to optimize workloads and communication within the team. To ensure successful implementation of status reports, the author looked for well-designed tools, communicated the need for the process, and made sure the team felt they were part of the decision-making process. This ultimately resulted in a successful implementation of the status reports.

I helped a direct report get out of “Hero” mode

A "Hero" employee was struggling to get out of their default mode of solving any problem that arose. The manager took action by offering the employee opportunities to grow and fill the space left by them moving to a new team with new hires and training. The lesson learned was that most "Heroes" end up in these situations due to bad onboarding and insufficient training, and it is the manager's role to guide them out of it.

Handling someone who ignores company policies

When employees ignore company policies, the most effective way to handle the situation is to point it out directly. Coaching employees is not helpful and could be counterproductive. Before deciding on how to handle a problem with an employee, determine if it is a mindset or skill set problem.

How to detect a potential problem within your team

During a one-on-one, a direct report expressed concern that some people were not aware of the time requirements associated with a process. After further investigation, it was found that the problem was due to one person not being prompt in responding to others. To solve the problem, clearer, quantitative language was used to match everyone's expectations. This experience taught the importance of being alert during one-on-ones, digging deeper if there is a sense of frustration, and watching out for patterns in stories across time.

How to encourage people to make the most of retrospectives

A senior engineer on a team was initially skeptical of the value of sprint retrospectives, but eventually came to understand their importance. It is important to listen to team members, create a safe space for them to share, and be flexible and adjust when necessary. There are lots of activities available to help identify areas of improvement in retrospectives.

The Push to Production Process Not Respected

When errors were occurring during the push to production process, a checklist was created to help the developers. However, people started to bypass the checklist, so an "production push algorithm" was created instead. This algorithm was more explicit and efficient, and now it is used for tasks beyond just development.

How to handle tension caused by cultural differences

A team split between Buenos Aires and Dallas had a negative impression of an engineer in Dallas due to his lack of knowledge of industry standards and his direct, even mean, attitude towards the Argentinian engineers. After discussing cultural differences, the engineer changed his behavior and the team was able to work together. It is important to set expectations for different cultures to interact and to discuss cultural differences in order to prevent misunderstandings.

What to do with an employee who wants to step-up

A good engineer was interested in becoming a senior engineer, so the manager discussed the criteria for promotion with him line-by-line. They had several follow-up conversations and the manager made it clear that the promotion was up to the employee's work. This showed the importance of setting clear expectations when promoting an employee.

How I improved at giving negative feedback

This article discusses the importance of giving negative feedback, even to people you care about. It suggests starting with your top performers and emphasizes that feedback is a gift. It also highlights the importance of giving feedback early on, rather than waiting until someone is on a performance plan and in line to be dismissed.

I took too much time trying to detect the origin of a problem

When a new manager arrived in a team, they noticed that the tech lead was more concerned with political matters than the quality of the code shipped. After a long process of trying to help the tech lead boost their performance, they had to be let go. The manager learned that it was important to build a genuine relationship with the team to understand where problems are coming from.

Adjusting Best Practices as a Company Grows

The engineering manager at Blablacar held a weekly meeting with the engineering team, but as the team grew, the value of the meeting was not appreciated and it was eventually stopped. The author learned that when leading a meeting with a large team, it is better to suggest solutions rather than ask for them.

Coaching a recently hired engineer on their areas of improvement

A manager arrived to a team of high performers and noticed that one junior employee was not fitting in with the company culture. The manager took action by creating a relationship of trust and setting clear goals and expectations for the employee. Through coaching and setting measurable paths, the employee has improved in collaboration, accountability, and quality of work. The manager learned that it is important to help young employees work in an open and trusted environment, and to have career discussions on an ongoing basis.

Be agile in your processes

Scrum is the most popular agile software development methodology, but it is important to consider if it is the right approach for the product being built. Flexibility is key, as sprint duration, start and end times, and retrospectives should be tailored to the team and the business. Two-week sprints are a good compromise between too much time between projects and too much time spent in meetings. Mid-week sprint starts are preferable to avoid holidays and keep people energized. Sprint reviews should be used to adjust the product, and retrospectives to adjust the process.

The first time you have to let go of someone

A manager was faced with the difficult task of firing an underperforming employee. With the help of their manager and former manager, they were able to handle the situation and fire the employee. The manager learned the importance of being determined and giving constructive feedback before firing someone.

A team member struggling with working remotely

A team of engineers was managed remotely, and one member was performing poorly and inconsistently. After providing direct feedback and learning that it was her first remote job, the manager was unable to directly fire her and had to get authorization. Ultimately, the team member was fired and the manager learned that working remotely is not for everyone and that the team member needed more structure in her life to succeed.

Ensuring all your teams work together as a single unit

In this case study, the author was leading an engineering team that was performing well but felt burned out. After meeting with the leads of the other teams (Product Management, User Experience, Support, QA, Documentation, etc.), the author implemented design sessions that included all relevant teams and organized team lunches to restore trust. As a result, the product was well-received and the documentation was impeccable. The lesson learned is to always involve all teams in the organization, as each team has something to contribute.

The Importance of Gathering Honest Feedback

A co-founder of Box had difficulty with a back-end engineering manager and eventually decided to let him go. However, the day after, a bunch of back-end engineers were going to quit due to the co-founder's actions. To understand why, the co-founder sat down with each of the engineers and heard from lots of different people who said that they didn't like the job that he was doing. He realized that he had failed to be cognizant of the power dynamic between himself and the new engineers and hired a coach to get feedback on his performance. He worked hard to make improvements in his areas of weakness and started proactively asking for feedback. He learned that his title and status in the company can inhibit people from providing him with feedback and that he must be proactive in reaching out for it.

What to take into account when choosing between technical debt and new features

Technical debt can be difficult to manage, and it can be hard to decide when to prioritize it. A team faced with the challenge of managing technical debt while also building new features found that they were unable to do either. This caused stability and scalability issues, and the team had to focus on firefighting instead of being proactive. The lesson learned is that technical debt should be prioritized, and it is important to consider the specific situation when making decisions.

How to scale a company?

Stripe's rapid growth led to an organizational structure that was no longer suitable, resulting in unclear ownership of projects, delayed work, and a lack of clear boundaries for each employee's tasks. To adapt to this growth, changes were implemented, but they started to irritate people. To remedy this, the focus was shifted to talking to people and gathering feedback, while preparing future managers for their positions. It is important to keep in mind that the organizational structure of a startup has to change as the company grows, and that the most important thing is to implement the process smoothly and to involve people in the changes.

Transitioning to dedicated agile coaches (scrum masters)

When the engineering team at a previous company grew to 35+ engineers, they encountered issues with agile coaching. To solve this, they decided to hire a freelance scrum master for a trial period, and then hired a full-time agile coach. This proved to be successful, and the team of agile coaches grew to five people. Benefits of having an in-house team of agile coaches include having experts who can own the process, having someone with team performance and improving methodology as their main metric and objective, and having no hierarchical relationship between scrum masters and EMs.

How to implement new work processes in a tech team?

When transitioning to a managerial role, the author found it necessary to introduce new processes and tools to optimize workloads and communication within the team. To ensure successful implementation of status reports, the author looked for well-designed tools, communicated the need for the process, and made sure the team felt they were part of the decision-making process. This ultimately resulted in a successful implementation of the status reports.

I helped a direct report get out of “Hero” mode

A "Hero" employee was struggling to get out of their default mode of solving any problem that arose. The manager took action by offering the employee opportunities to grow and fill the space left by them moving to a new team with new hires and training. The lesson learned was that most "Heroes" end up in these situations due to bad onboarding and insufficient training, and it is the manager's role to guide them out of it.

Handling someone who ignores company policies

When employees ignore company policies, the most effective way to handle the situation is to point it out directly. Coaching employees is not helpful and could be counterproductive. Before deciding on how to handle a problem with an employee, determine if it is a mindset or skill set problem.

How to detect a potential problem within your team

During a one-on-one, a direct report expressed concern that some people were not aware of the time requirements associated with a process. After further investigation, it was found that the problem was due to one person not being prompt in responding to others. To solve the problem, clearer, quantitative language was used to match everyone's expectations. This experience taught the importance of being alert during one-on-ones, digging deeper if there is a sense of frustration, and watching out for patterns in stories across time.

How to encourage people to make the most of retrospectives

A senior engineer on a team was initially skeptical of the value of sprint retrospectives, but eventually came to understand their importance. It is important to listen to team members, create a safe space for them to share, and be flexible and adjust when necessary. There are lots of activities available to help identify areas of improvement in retrospectives.

The Push to Production Process Not Respected

When errors were occurring during the push to production process, a checklist was created to help the developers. However, people started to bypass the checklist, so an "production push algorithm" was created instead. This algorithm was more explicit and efficient, and now it is used for tasks beyond just development.

How to handle tension caused by cultural differences

A team split between Buenos Aires and Dallas had a negative impression of an engineer in Dallas due to his lack of knowledge of industry standards and his direct, even mean, attitude towards the Argentinian engineers. After discussing cultural differences, the engineer changed his behavior and the team was able to work together. It is important to set expectations for different cultures to interact and to discuss cultural differences in order to prevent misunderstandings.

What to do with an employee who wants to step-up

A good engineer was interested in becoming a senior engineer, so the manager discussed the criteria for promotion with him line-by-line. They had several follow-up conversations and the manager made it clear that the promotion was up to the employee's work. This showed the importance of setting clear expectations when promoting an employee.

How I improved at giving negative feedback

This article discusses the importance of giving negative feedback, even to people you care about. It suggests starting with your top performers and emphasizes that feedback is a gift. It also highlights the importance of giving feedback early on, rather than waiting until someone is on a performance plan and in line to be dismissed.

I took too much time trying to detect the origin of a problem

When a new manager arrived in a team, they noticed that the tech lead was more concerned with political matters than the quality of the code shipped. After a long process of trying to help the tech lead boost their performance, they had to be let go. The manager learned that it was important to build a genuine relationship with the team to understand where problems are coming from.

Adjusting Best Practices as a Company Grows

The engineering manager at Blablacar held a weekly meeting with the engineering team, but as the team grew, the value of the meeting was not appreciated and it was eventually stopped. The author learned that when leading a meeting with a large team, it is better to suggest solutions rather than ask for them.

Coaching a recently hired engineer on their areas of improvement

A manager arrived to a team of high performers and noticed that one junior employee was not fitting in with the company culture. The manager took action by creating a relationship of trust and setting clear goals and expectations for the employee. Through coaching and setting measurable paths, the employee has improved in collaboration, accountability, and quality of work. The manager learned that it is important to help young employees work in an open and trusted environment, and to have career discussions on an ongoing basis.

Be agile in your processes

Scrum is the most popular agile software development methodology, but it is important to consider if it is the right approach for the product being built. Flexibility is key, as sprint duration, start and end times, and retrospectives should be tailored to the team and the business. Two-week sprints are a good compromise between too much time between projects and too much time spent in meetings. Mid-week sprint starts are preferable to avoid holidays and keep people energized. Sprint reviews should be used to adjust the product, and retrospectives to adjust the process.

The first time you have to let go of someone

A manager was faced with the difficult task of firing an underperforming employee. With the help of their manager and former manager, they were able to handle the situation and fire the employee. The manager learned the importance of being determined and giving constructive feedback before firing someone.

A team member struggling with working remotely

A team of engineers was managed remotely, and one member was performing poorly and inconsistently. After providing direct feedback and learning that it was her first remote job, the manager was unable to directly fire her and had to get authorization. Ultimately, the team member was fired and the manager learned that working remotely is not for everyone and that the team member needed more structure in her life to succeed.

Ensuring all your teams work together as a single unit

In this case study, the author was leading an engineering team that was performing well but felt burned out. After meeting with the leads of the other teams (Product Management, User Experience, Support, QA, Documentation, etc.), the author implemented design sessions that included all relevant teams and organized team lunches to restore trust. As a result, the product was well-received and the documentation was impeccable. The lesson learned is to always involve all teams in the organization, as each team has something to contribute.

The Importance of Gathering Honest Feedback

A co-founder of Box had difficulty with a back-end engineering manager and eventually decided to let him go. However, the day after, a bunch of back-end engineers were going to quit due to the co-founder's actions. To understand why, the co-founder sat down with each of the engineers and heard from lots of different people who said that they didn't like the job that he was doing. He realized that he had failed to be cognizant of the power dynamic between himself and the new engineers and hired a coach to get feedback on his performance. He worked hard to make improvements in his areas of weakness and started proactively asking for feedback. He learned that his title and status in the company can inhibit people from providing him with feedback and that he must be proactive in reaching out for it.

What to take into account when choosing between technical debt and new features

Technical debt can be difficult to manage, and it can be hard to decide when to prioritize it. A team faced with the challenge of managing technical debt while also building new features found that they were unable to do either. This caused stability and scalability issues, and the team had to focus on firefighting instead of being proactive. The lesson learned is that technical debt should be prioritized, and it is important to consider the specific situation when making decisions.

How to scale a company?

Stripe's rapid growth led to an organizational structure that was no longer suitable, resulting in unclear ownership of projects, delayed work, and a lack of clear boundaries for each employee's tasks. To adapt to this growth, changes were implemented, but they started to irritate people. To remedy this, the focus was shifted to talking to people and gathering feedback, while preparing future managers for their positions. It is important to keep in mind that the organizational structure of a startup has to change as the company grows, and that the most important thing is to implement the process smoothly and to involve people in the changes.

Transitioning to dedicated agile coaches (scrum masters)

When the engineering team at a previous company grew to 35+ engineers, they encountered issues with agile coaching. To solve this, they decided to hire a freelance scrum master for a trial period, and then hired a full-time agile coach. This proved to be successful, and the team of agile coaches grew to five people. Benefits of having an in-house team of agile coaches include having experts who can own the process, having someone with team performance and improving methodology as their main metric and objective, and having no hierarchical relationship between scrum masters and EMs.

How to implement new work processes in a tech team?

When transitioning to a managerial role, the author found it necessary to introduce new processes and tools to optimize workloads and communication within the team. To ensure successful implementation of status reports, the author looked for well-designed tools, communicated the need for the process, and made sure the team felt they were part of the decision-making process. This ultimately resulted in a successful implementation of the status reports.

I helped a direct report get out of “Hero” mode

A "Hero" employee was struggling to get out of their default mode of solving any problem that arose. The manager took action by offering the employee opportunities to grow and fill the space left by them moving to a new team with new hires and training. The lesson learned was that most "Heroes" end up in these situations due to bad onboarding and insufficient training, and it is the manager's role to guide them out of it.

Handling someone who ignores company policies

When employees ignore company policies, the most effective way to handle the situation is to point it out directly. Coaching employees is not helpful and could be counterproductive. Before deciding on how to handle a problem with an employee, determine if it is a mindset or skill set problem.

How to detect a potential problem within your team

During a one-on-one, a direct report expressed concern that some people were not aware of the time requirements associated with a process. After further investigation, it was found that the problem was due to one person not being prompt in responding to others. To solve the problem, clearer, quantitative language was used to match everyone's expectations. This experience taught the importance of being alert during one-on-ones, digging deeper if there is a sense of frustration, and watching out for patterns in stories across time.

How to encourage people to make the most of retrospectives

A senior engineer on a team was initially skeptical of the value of sprint retrospectives, but eventually came to understand their importance. It is important to listen to team members, create a safe space for them to share, and be flexible and adjust when necessary. There are lots of activities available to help identify areas of improvement in retrospectives.

The Push to Production Process Not Respected

When errors were occurring during the push to production process, a checklist was created to help the developers. However, people started to bypass the checklist, so an "production push algorithm" was created instead. This algorithm was more explicit and efficient, and now it is used for tasks beyond just development.

How to handle tension caused by cultural differences

A team split between Buenos Aires and Dallas had a negative impression of an engineer in Dallas due to his lack of knowledge of industry standards and his direct, even mean, attitude towards the Argentinian engineers. After discussing cultural differences, the engineer changed his behavior and the team was able to work together. It is important to set expectations for different cultures to interact and to discuss cultural differences in order to prevent misunderstandings.

What to do with an employee who wants to step-up

A good engineer was interested in becoming a senior engineer, so the manager discussed the criteria for promotion with him line-by-line. They had several follow-up conversations and the manager made it clear that the promotion was up to the employee's work. This showed the importance of setting clear expectations when promoting an employee.

How I improved at giving negative feedback

This article discusses the importance of giving negative feedback, even to people you care about. It suggests starting with your top performers and emphasizes that feedback is a gift. It also highlights the importance of giving feedback early on, rather than waiting until someone is on a performance plan and in line to be dismissed.

I took too much time trying to detect the origin of a problem

When a new manager arrived in a team, they noticed that the tech lead was more concerned with political matters than the quality of the code shipped. After a long process of trying to help the tech lead boost their performance, they had to be let go. The manager learned that it was important to build a genuine relationship with the team to understand where problems are coming from.

Adjusting Best Practices as a Company Grows

The engineering manager at Blablacar held a weekly meeting with the engineering team, but as the team grew, the value of the meeting was not appreciated and it was eventually stopped. The author learned that when leading a meeting with a large team, it is better to suggest solutions rather than ask for them.

Coaching a recently hired engineer on their areas of improvement

A manager arrived to a team of high performers and noticed that one junior employee was not fitting in with the company culture. The manager took action by creating a relationship of trust and setting clear goals and expectations for the employee. Through coaching and setting measurable paths, the employee has improved in collaboration, accountability, and quality of work. The manager learned that it is important to help young employees work in an open and trusted environment, and to have career discussions on an ongoing basis.

Be agile in your processes

Scrum is the most popular agile software development methodology, but it is important to consider if it is the right approach for the product being built. Flexibility is key, as sprint duration, start and end times, and retrospectives should be tailored to the team and the business. Two-week sprints are a good compromise between too much time between projects and too much time spent in meetings. Mid-week sprint starts are preferable to avoid holidays and keep people energized. Sprint reviews should be used to adjust the product, and retrospectives to adjust the process.

The first time you have to let go of someone

A manager was faced with the difficult task of firing an underperforming employee. With the help of their manager and former manager, they were able to handle the situation and fire the employee. The manager learned the importance of being determined and giving constructive feedback before firing someone.

A team member struggling with working remotely

A team of engineers was managed remotely, and one member was performing poorly and inconsistently. After providing direct feedback and learning that it was her first remote job, the manager was unable to directly fire her and had to get authorization. Ultimately, the team member was fired and the manager learned that working remotely is not for everyone and that the team member needed more structure in her life to succeed.

Ensuring all your teams work together as a single unit

In this case study, the author was leading an engineering team that was performing well but felt burned out. After meeting with the leads of the other teams (Product Management, User Experience, Support, QA, Documentation, etc.), the author implemented design sessions that included all relevant teams and organized team lunches to restore trust. As a result, the product was well-received and the documentation was impeccable. The lesson learned is to always involve all teams in the organization, as each team has something to contribute.

The Importance of Gathering Honest Feedback

A co-founder of Box had difficulty with a back-end engineering manager and eventually decided to let him go. However, the day after, a bunch of back-end engineers were going to quit due to the co-founder's actions. To understand why, the co-founder sat down with each of the engineers and heard from lots of different people who said that they didn't like the job that he was doing. He realized that he had failed to be cognizant of the power dynamic between himself and the new engineers and hired a coach to get feedback on his performance. He worked hard to make improvements in his areas of weakness and started proactively asking for feedback. He learned that his title and status in the company can inhibit people from providing him with feedback and that he must be proactive in reaching out for it.