It shouldn’t be a surprise that the outlook for many tech companies in 2023 is not rosy. With layoffs across the industry, we’re all going through a challenging time - whether you’re a dev or not.

The last 14 years have been an unprecedented boom time - but economic conditions will eventually challenge all companies. How do we, as leaders, handle these challenges? 
I sat down with Michael Stahkne, VP of platform at Circle CI; Lewis Tuff, VP of engineering at Blockchain.com; Carolyn Vo, partner & head of engineering at Oliver Wyman, for a panel at Dev Interrupted's conference to answer that exact question. Here’s how these leaders described what effective leadership looks like in uncertain times.

1. Increase the quality and frequency of communication

Some people will see this as counterintuitive. If times are tough, don’t you need more time to get work done? However, stellar communication is one critical way to lead effectively in both prosperous  times and times of crisis.

Michael had a strong viewpoint on this: in an async remote world, he will communicate when he needs to, and he expects his colleagues to share when they need time back. They have tools with settings to mute communications and get notifications as they see fit, and they can choose when to respond. 

Why meeting communication matters

It’s important to acknowledge that part of communicating well involves meetings (gasp!). It’s common to hear engineers complain about meetings. Yes, it’s good to streamline meeting schedules to reduce synchronous status updates that force context-switching. There are, however, ways to have effective meetings—and some are essential. Many meetings are crucial working sessions where you can collaborate with your colleagues.

Yet not all communication is formal. Informal signaling is also key. For example,  Carolyn shared  how she jokingly refers to herself as “Jr. Probationary Intern” to break down the artificial separation between you and your teammates as you become more senior. You can’t get rid of the power dynamic completely, but you don’t want your new people to be scared of you, and you need to have their trust to understand people’s motivations. Carolyn chooses to try to lower that separation through humor and direct acknowledgment.

You can't let this happen:

2. Connect motivation to business results

Understanding your team’s motivation is also essential. When things are uncertain, you must determine what motivates each team member. They’ll have questions like “Will I get to write the code I like?” And you have to answer immediately, “Yes, you will,” or “Yes, but you’re going to be reallocated to this new group.”

Michael also noted an often underrated motivating factor: How is your company oriented?

If your company is customer-oriented, if you’re focused on what they’re trying to achieve and are helping them do that—it softens the blows that land on your own company in tough times. Cutting back on your bets and focusing on your high-impact projects can also help with this and is sometimes necessary; sadly, this is often seen in layoffs or “reductions in workforce”.

Instill excitement through experimentation

Once you understand people’s motivations, you can help bring joy by providing space for teams to have fun.

When valuations are going up and to the right, it’s a lot easier to have work feel fun - so in an uncertain period, it’s imperative to get teams excited when you can. It lets people stop focusing on the downturn and instead on things that excite them.

Everyone can define “fun” differently, but knowing your team’s motivation can help you find the right ways to provide some levity and keep everyone aligned. You can bring fun in simple ways, like sharing something interesting you learned at the start of a meeting or, in Michael’s case, by throwing in emojis on Slack and shooting memes at a high rate per day.

For Lewis, teammates can find fun by having space to experiment and try new things with little pressure. Even if you disagree with your direct report’s decisions, part of providing space to experiment is still advocating for them and letting their choices play out—even if what they’re making feels like something you’ve seen before. Even then, the variables can be different, and it could turn out entirely differently. Whatever you do, don’t tell everyone you disagree with your team member’s idea. 

3. Have the tough conversations

One way to understand how much fun a team can have is to understand your tolerance for failure, which can get stricter as things get uncertain. But being transparent about this tolerance will continue to give team members the space to enjoy their work.

There is a myth that you must filter lousy news and hard decisions as a leader. But being transparent helps people understand the context behind why things are happening and helps ensure people aren’t being shocked. If you end up filtering news, you breed rumors and speculations, which can produce resentment.

Blame is a communication killer

Another pitfall to avoid with tough communication is blame. One example of blameful leadership is when a team member asks for a raise, and the leader says, “I want to give you one, but my boss won’t let me.” This type of blaming irks leaders like Michael, partly because it comes off as inauthentic. Authenticity is an integral part of being transparent and conducting successful challenging communication. There are a lot of discussions you can have during tough conversations beyond finding someone else to blame. Plus, people who own messaging are more likely to get promoted.

What to avoid when providing critical feedback

Providing harsh feedback can be challenging, particularly across cultural boundaries where how tough feedback is communicated can vary wildly. Like Carolyn, this is an area of improvement I see for myself as a leader, and somewhere, I’ve made mistakes. One example: I had to communicate critical feedback to a team member and thought I was writing a thorough and fair review by simply writing extensive feedback and including positives and negatives.

However, I didn’t spend enough time thinking about how to communicate that critical feedback: I started by addressing an area of concern and initially shared the feedback in writing vs. having a conversation with them. In some cultures, such as the Netherlands, this might have been perfectly acceptable--but in working with a US-based team member who was seeing layoffs at other companies, it backfired. Instead of helping provide feedback to initiate improvement, I’d caused them to worry that their job was at risk. 

In the end, I had to assuage this team member's worries--and acknowledge my own failure in how I communicated the criticism; I lacked context and empathy in my communication. When sharing critical feedback, I needed to remember the old US business adage of two positives to one negative.

4. Remove team roadblocks but track team progress

While communication is crucial for leadership, particularly in tough times, it isn’t the only thing. It’s also important to buckle down and ask yourself, “How can we as leaders remove roadblocks?”

If we want our team members to direct how they want to progress, we need to figure out how to support that and track it. By tracking this for your reports, you can align how you feel they progressed with how they feel while tailoring things to the individual. For engineering leaders, understanding the health of your team - without being a data-driven tyrant - is a crucial first step. 

A helpful next step is to find the individuals who are driving the company's principles and have them mentor teammates. Leadership can come from every seat but often requires effort to foster culturally and enable team members' progression.

Leading teams in uncertain times

Leading in uncertain times hinges on communication, transparency, and understanding motivation. You can’t treat everyone the same, as everyone has different goals and ideas for fun. The more you tailor to your individuals, the more you can help your team thrive in uncertainty. 

Watch my whole conversation with Carolyn, Michael, and Lewis on our YouTube 👇

“Treating devs like human beings” may sound like it should be an obvious idea. Yet we see the opposite happening on a regular basis - developers measured on lines of code, managers who expect engineers to act like automatons, and too many practices that sacrifice developer happiness and decay teams for short-term delivery.

To discuss how to fix these negative practices that too often damage our industry, I was joined by 3 experts in making the transition from churn and burn software development to more successful, human-centric development. 

Here are the 6 major takeaways from my conversation with Kelly Vaughn, Director of Engineering at Spot AI; engineering leadership coach Lena Reinhard and VP of Engineering at Range, Jean Hsu.

1. Humanize Interviews

Sometimes, we must remind each other that developers are knowledge workers, not robots. During our conversation, Kelly shared her view on one of the roots of this problem: the belief that engineers shouldn’t be required to code as part of the interview process. 

Her reason? Such tests don’t reflect actual working conditions. After all, when was the last time anyone stood over your shoulder at work and watched you code? Instead, she advocates for more problem-oriented system-design interviews that showcase how candidates think. 

Jean aligned with this, saying interviews should focus more on what it’s like to work with a person instead of how technically strong they are. However, humanizing interviews starts before the interview itself -  it means thinking about what your job descriptions and interviews cater to: Do they support people who have kids? People who already have a second job? Or do they hone in on “super passionate” developers who often have more free time?

2. API for Humans

Beyond interviews, Jean thinks that treating your working developers as humans is one of the industry’s biggest gaps. People moving into leadership and management roles are not trained to communicate and figure out, “Hey, what’s important to this other human?” She recalls one communication workshop where a person shared the takeaway “I feel like I just learned an API for humans.” 

Kelly Vaughn brings a unique perspective to this discussion - that of a  trained therapist. She leverages this training to monitor behavior and patterns of speech to see when interventions are needed and to understand the needs of her developers. It’s interesting to compare this approach to other managers who don’t get the same in-depth training in communication and in improving their emotional intelligence. So many times we promote developers to managers and actually set them up for failure. As a leader, it’s crucial to view developers not just as resources but as complex humans so that you can help them understand what they really want and how to create mutual value as part of the team. If we solely focus on the value to the business - and not the developer experience in building that business value - we sacrifice for short-term productivity bursts and decrease retention rates, causing major issues and costing the business money in the longterm.

One of my favorite examples of how to approach this dichotomy comes from Jean - one of her engineers told her they were having challenges balancing full-time work with other goals. This engineer was talented and a valuable member of the team, so Jean worked with them to transition them into a part-time role that let them have more time back for personal projects and more closely fit what they were looking for. This kind of relationship is challenging to develop, but when done right can both deliver for the business's needs and recognize each human's unique challenges. 

3. Can a Dev Manager Be Non-Technical?

With this focus on communication and humanization vs. technical skills, the natural next question is whether or not developers need to be led by managers with technical skills. From Lena’s experience, many great engineering managers are people who haven’t been developers and likely never will. It doesn’t take someone from a technical background to enjoy working in tech and understand the motivations of their developers. Yet we continue to see companies where leaders seem to think that the way to fill gaps is pattern matching their engineers. They’re making people leaders who have similar skills or behaviors to their subordinates or who excelled as an individual contributor without necessarily having leadership skills. This contributes to engineers who struggle or burn out in poorly-fitting roles.

Part of the joy of engineering leadership is seeing your engineers grow. Part of letting them grow is to stop fixing for them and start coaching them to do the solving themselves. And when you come from a non-technical background, that temptation is less, which is part of why many great managers are not from a technical background.

4. Bringing Your Full Self to Work

Our panelists views one-on-ones not as a place to give performance advice, but as a place for engineers to share their dreams, personal endeavors, and concerns. Kelly, Lena and Jean all felt that one-on-ones were a powerful tool for leaders to break through the dehumanizing barriers of software development as production line. In fact, because of Kelly’s background as a trained therapist, she views a successfull one-on-one as something close to the therapy, though she cautions this approach doesn’t fit everyone.

However, just like a therapy session, a good one-on-one should be individualized, confidential, difficult to cancel and devoid of surprises. A leader also needs to bring their whole self to the meeting, or the employee won’t bring their whole self. 

Lena resonated deeply with this. It can be tricky for people to bring their whole selves due to culture, and a leader should figure out what their employees’ boundaries are between personal and work life. It’s also important to recognizes that it’s not just regional or company culture, but also generational culture that affects those boundaries. At Range, Jean’s team report their mood for the day as well as what they’re working on during check-ins. She shared a story where she was explaining this process to another older engineering leader and that that  person laughed in surprise that people would want to share something like mood in the workplace. 

Jean feels strongly that the way a company talks is really representative of how they view their employees. For example, consider when companies call it “resource allocation” instead of “how employees spend their time.” In a higher-level position, you need to watch the way you talk and how you’re feeling about the people who work for you.

5. Metrics

Kelly had a great example of humanizing vs. dehumanizing metrics: time to close a ticket vs. the impact of closing a ticket. The latter is much more powerful and speaks more to the nuance of what’s going on with a team. Metrics shouldn’t just track information, but also give people something to look forward to. People want to be doing their best work and as I’ve written, we can use metrics to improve productivity without sacrificing developer experience

You can get a feel for how humanizing - or dehumanizing - a company is by what metrics they use when measuring their devs. For example, lines of code is a dehumanizing metric because it’s meaningless to the actual value a developer can bring. One key to humanizing metrics is making sure the metric is something that a developer is aware of and has direct influence over. Kelly had a great example of humanizing vs. dehumanizing metrics: time to close a ticket vs. the impact of closing a ticket. The latter is much more powerful and speaks more to the nuance of what’s going on with a team. 

As we talk about ad naseum at LinearB, metrics should focus more on team performance than individual performance. Metrics shouldn’t just track information, but also give people something to look forward to. People want to be doing their best work and as I’ve written, we can use metrics to improve productivity without sacrificing developer experience

6. Burnout

Another crucial challenge that stops people from doing their best work is burnout. Jean shared about a time when her company shut down for a short break and people were hoping everyone would come back from the break refreshed. But the break was amid the COVID-19 pandemic, and instead of returning refreshed, she came back tired. During a morning check-in, she shared how tired she still felt and how the short break didn’t make up for months of pandemic stress. One of her direct reports told her later how relieved they were that Jean shared, because they felt the same way! Acknowledging the elephants in the room is crucial as a leader; everything can’t always be rosy and your team wants to feel seen in the challenges you share.

Another important thing to understand about burnout is that it’s not just something you need to accept: Kelly pointed out that burnout is recognized as a mental health syndrome. Knowing that, leaders must be aware that cultural influences impact people’s willingness to talk about mental health, including regional and national cultural considerations. Your team members may not want to talk about it, so you have to look for signs before the burnout hits full force. Address these signs as soon as you can, and give the employee the time and the space they need to heal from it. 

You’ve also got to manage upwards around burnout: When the pandemic hit, many companies said, “We care about you,” but didn’t take action. Instead of reducing capacity to 80% and telling people they could be less productive during that time, they tightened goals. They worried more about their performance than their employees’ humanity. As a leader within your organization, you need to raise your voice in leadership discussions and challenge the organization's negative actions by showing that there is a better way to lead.

Humanizing Means Performance

Humanizing developers is critical and isn’t divorced from performance. As Jean says, it’s not like you can say, “Let’s just get the team running; then we can focus on caring about them.” Caring about your team allows them to perform with great results! 

Watch my whole conversation with Jean, Kelly, and Lena on our YouTube 👇


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As an engineer, you might have learned the basics from textbooks or watching a series of tutorials. 

Managing engineers is different and isn’t something that can be mastered from simply reading a book. 

In my experience, the only proven way to learn is by plugging into the collective wisdom of smart people who have done the hard work of actually managing engineering teams.

That’s why I was so happy to speak with Ian Nowland of Datadog.

With 20 years of engineering industry experience — 10 of which have been in management positions — Ian developed a unique approach toward engineering management, encapsulated in seven categories. 

These seven categories of engineering management are based on his own software-engineering experience, which includes 10 years at Amazon and are designed to help managers successfully direct, satisfy and retain employees, as well as maintain a healthy company culture. 

Some of the central components of Ian’s framework include taking the ego out of mistakes, developing a learning mindset towards management, and building social capital between teams.

We’ll dig into this more below. 

Using the 7 Categories of Engineering Management 

People often refer to the three P’s when it comes to management: 1) People; 2) Process; and 3) Product. 

But Ian believes that’s limiting when you’re thinking about management in engineering and doesn’t account for the full range of engineering activity.

Instead, Ian believes it’s more helpful to consider the following: 

  1. People: Are people happy and growing in what is being built? 
  2. Engineering: How are things being built? This is about focusing on how your engineers get stuff done and how well those processes work — like the efficacy of a team’s code-review process. 
  3. Product: Are customers satisfied by what’s being built? Ian also refers to this category as “portfolio management.” It’s about communicating with an engineering team about their roadmap, what milestones they plan to explore in that year or quarter, and what story they want to tell through their work. 
  4. Partners: Do your partners understand and agree with all of the above? It’s important to foster healthy relationships between teams and any affiliated groups across the company. 
  5. Execution: How are things getting built? Managers have to think about what has to be done and how they should organize teams to meet annual milestones. 
  6. Operations: Once your product/org is built, is it going to keep running? Operational processes, like scrums or sprints, are crucial to the success of a software engineering project, so it’s important that managers ensure these processes are effective and efficient. 
  7. Company: Does the company align with all these answers? It’s every engineering manager’s responsibility to reflect their company’s culture. A manager’s actions (or inactions) will set a precedent for their teams and direct reports. 

The “Miss” Approach For Managing Engineers 

Ian believes that when you’re managing engineers, there’s a lot to oversee. There are tons of opportunities for mistakes along the way — they can and will happen. But Ian’s found that it’s through making mistakes — or “misses” — that everyone gets to improve. 

A “miss” occurs whenever something goes wrong that could’ve been prevented. But here’s the key: Don’t think of a miss as a mistake — it’s a teaching moment. 

It’s a subtle mindset shift. Instead of focusing on the mistake (which can be damaging to a person’s ego), view it as an opportunity for growth.

Managing by Missing from Ian Nowland

When you start thinking in terms of misses, it becomes easier to digest. It’s like: That’s okay, I’ll get it next time. Ian found this especially effective for people with perfectionist tendencies (and I’m the first to admit I definitely fall into that category). 

Using a Miss To Build Social Capital (aka Get What You Want)

Ian provided a beautiful example to illustrate what he was talking about.

Let’s get specific. Looking at the categories, here’s a miss I experienced in a previous job when dealing with partners at the company. 

At the time, I was managing a software team that was in charge of a network device. A previous manager had made the decision to use a different vendor, and the network team basically said: we’re out. As you can probably tell, there was some friction between the two teams. By the time I started working with this group of software engineers, it was clear they were in over their heads. 

I went to the woman who was the head of the network device team to ask if we could turn this over to her team — after all, software engineers have no business running networking devices. Since we were using our own vendor and her team was busy, she didn’t agree. 

At an earlier point in my career, I would have felt frustrated and left it at that. But past misses (and the seven categories!) have taught me to look at the bigger picture. In this case, she’s well-intentioned and doing the best she can. 

Considering the importance of building good relationships between teams, I focused on that. At one point, I even volunteered one of my engineers to help her with a software project to build goodwill. 

About a year later, I approached her again to ask about taking over this particular network device. This time the answer was yes. 

What changed? We’d built up some trust. We’d taken opportunities to show her that we were trying to do the right thing for the company (by helping her out), and so we’d established the social capital to get a positive response when we made an ask. 

Want to hear what Ian learned from other misses? Listen in at 11:50 to hear about a miss in execution and how he came back from a project that went off the rails. 

Does It Work? Measuring Success 

When it comes to measuring impact, Ian doesn’t believe there’s a universal measure of success — it’ll change according to the situation. 

Engineering leader Michael Lopp has written about management in terms of “organics and mechanics.” Ian tends to sway toward being an “organic,” which is essentially intuition-driven. 

In his current role, Ian oversees a lot of managers. One of the main things he looks at is whether the managers are surfacing misses early — before they feel like a surprise. 

When you manage a lot of different people, your job is to delegate well. The number of surprises is a good indicator of whether everyone is on top of what they’re responsible for — if there are few surprises, you don’t need to get too involved and that things are going well. 

When measuring operations and delivery goals, these are areas where it makes sense to apply different standards. For example, objectives and key results (OKRs) are helpful the higher up you go on the organizational chart. When evaluating managers, Ian wants to know: Did they accomplish what they set out to do? If not, why didn’t it work out as expected? 

Ian says you wouldn’t expect a team lead to care about OKRs; a team lead should be more concerned with measuring scrum.

Engagement surveys can be helpful for surfacing sentiment. But Ian doesn’t find them helpful for differentiating between a teams’ level of happiness versus its level of impact.

One-On-One Meetings Should Be Fluid and Unique

There’s much written about one-on-one meetings between managers and their employees, and rightfully so. It’s an important interaction for any coaching relationship. But a by-the-book approach to one-on-one meetings isn’t always a recipe for success. 

The thing to keep in mind is that there’s no one-size-fits-all approach to these meetings. One-on-ones should be about helping engineers find unique solutions to their unique problems, rather than trying to present a milquetoast solution. At times, you might need to play the role of advisor, listener or coach. A fluid approach that is authentically yours is best. 

Ian also recommends managers use open-ended questions to guide these conversations. For example, he’ll start a one-on-one meeting with something like, “Hey, someone else has this opinion about something that you are or aren’t doing, what do you think?” 

This opens up the conversation so that they don’t think that you’re attacking or trapping them. Instead, it helps them gain different perspectives on their career path or a work-related problem. 

How To Avoid Burnout Among Engineers and Managers

Lots of engineers tend to burn out in their twenties. But for Ian, it took a lot longer. It wasn’t until Ian was mid-career when he realized that his workload was no longer sustainable. 

He was taking on too much work, and was such a perfectionist that he couldn’t and wouldn’t delegate that work to other people. He had been working way too hard for too long. He felt a sense of powerlessness: Ian went from eager and motivated to unmotivated and uninspired.  

Eventually Ian realized that he had to slow down and find a solution to being overworked because he was, in fact, burned out. 

For managers, the best advice for avoiding burnout is to first focus on delegating as much as you can. This will free up more time for you to focus on avoiding misses. 

People grow through delegation — so you want to enable your direct reports to make the mistakes for themselves so that they can anticipate and avoid them next time (and hopefully not burn out in the process of learning this all). This article is based on an episode of Dev Interrupted, featuring expert guests from around the world to explore strategy and day-to-day topics ranging from dev team metrics to accelerating delivery.

Hear the full talk

This advice only scratches the surface of how organizations can make their business more efficient and productive. You can find out much more about the team-of-teams model and how it applies to business by listening to our podcast.

Learning to code doesn’t mean you have to become a programmer. Coding is one of those professions with a lot of transferable skills: logic, clear thinking, problem solving, and attention to detail, to name just a few. So learning a programming language can open up a whole range of opportunities, even if you decide to veer away from becoming a developer.

We spoke with Peter Bell, founder and CTO at CTO connection, on our podcast to see what avenues are open to those that learn how to program. Here’s what he said.

Be an individual contributor

If you enjoy programming, but don’t enjoy the management side of the role, then you’ll want to look into becoming an individual contributor (IC). An IC is someone who focuses on the actual programming, without any of the management responsibilities. In the past, this wasn’t a viable career path. But things have changed.

“It always used to be like: Hey, if you want to make more money and, you know, make your parents proud, then you've got to go become a manager and stop doing the thing you're actually good at. Which is writing code,” Peter explains. “So it's good that we've got the dual-track career path, now.”

-On the Dev Interrupted Podcast at 04:43

Now, if you want to focus solely on being a programmer, that’s a viable option.

Get into management

The fact that we now have a dual-track career path means that if you’re particularly extroverted or enjoy training others up, you can choose to head in that direction. Sure, you won’t be coding as much. But your coding knowledge will help make sure that you can train up your team, and understand what they need to work on.

On a similar vein, it’s worth considering overseeing an entire product. This is where you can take that extra step away and really think about the user experience. What makes the best sense for them? How should this piece of software work? How do all these pieces fit together? A product manager needs the skills of any manager, but also needs to be able to think about the actual experience.

“Somebody who has a solid technical background who moves into product, it's another way of scaling your impact, because now you can think about the user experience and the flows without having to be like: Dammit, I got the semi-colon in the wrong place,” Peter explains. “So you get what the geeks are talking about, but you can actually focus on the impact for the users... You can still talk thoughtfully about, you know, how are we going to run this in a Kubernetes cluster and how are we going to think about, you know, real time stream queries against the data source?” 

-On the Dev Interrupted Podcast at 05:06

Being able to take a step back away from the day-to-day coding can be great for those that enjoy reviewing code and looking for errors. When developing products, you won’t spend as much time writing new code, but you’ll get to think through the problems at a more abstract level.

Train or consults others

Another role, which can suit those that prefer the freelance life, is to move into training or consultancy. Companies are always looking to teach their staff about new techniques and languages. So if you have a knack for passing on your skills, you’ll be in high demand. In fact, Peter described on the podcast how he started off by writing blogs about ColdFusion. 

“I started presenting a technical conference around the US and around the world, and then I realized, once I got to a certain point, that people would pay me to do this,” Peter says. “I've been on the other side where I'm paying someone to come in and talk about Redis or whatever. And I'm always saying to myself: This is really expensive, but we're still paying for it.”

-On the Dev Interrupted Podcast at 06:36

Being able to pick up a new language or technology quickly is a skill that not many have. So if you can do it, you can easily go into consultancy or training and earn a substantial salary. For example, Peter explains that large companies will often pay between $10,000 and $15,000 for a single day training 30 engineers. If you can pull it off, and leave those engineers with the right skills, you only need a few jobs to make a good living.

Try being a sales engineer

If you’re someone who enjoys working with people and thinking about the overall architecture of a project, rather than the fiddly details, then you might have more impact if you become a sales engineer. This role is all about understanding a product inside and out, giving demos and presenting the facts. The best sales engineers are the knowledgeable ones.

“It’s this intersection between understanding computers and being able to speak to a human. And it’s a relatively rare trait,” Peter says. “It seems engineering is awesome because what you do is you get to go and hang out with other geeks, and understand their problems.”

-On the Dev Interrupted Podcast at 13:20

So rather than focusing on coding, then coming back in six months with a finished product, you get to have those high-level talks. What are your big pain points? What are the issues with your engineering flows? How might this tool or product reduce cycle time? Which can often be a lot more rewarding and enjoyable.

Check out the podcast

These are just some of the jobs that are available to you, once you know how to code. But if you’d like to hear more about what Peter talked about, listen to our podcast.

Starved for top-level software engineering content? Need some good tips on how to manage your team? This article is inspired by Dev Interrupted - the go-to podcast for engineering leaders.

Dev Interrupted features expert guests from around the world to explore strategy and day-to-day topics ranging from dev team metrics to accelerating delivery. With new guests every week from Google to small startups, the Dev Interrupted Podcast is a fresh look at the world of software engineering and engineering management.

Listen and subscribe on your streaming service of choice today.

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Over the last ten years, technology has become more sophisticated. Faster. Smaller. More powerful. But it isn’t just our technology that’s evolving at a rapid pace. Our culture, attitudes and politics are all changing, too.

So what could the next ten years look like? How might businesses change to keep up with technology? We spoke with Jason Warner, managing director at Redpoint Ventures, to get his thoughts on the matter.

“Ten years is an interestingly long, but also short time horizon,” Jason explained. “It’s likely we’ll see a complete company cycle, maybe two macroeconomic cycles.”

-On the Dev Interrupted Podcast at 10:29

1. Organizations will invest more in compliance and security

There have been a lot of large changes in recent years. People are working from home. Political tensions are high. And almost every device collects data about us. In all these cases, security is important. Securing our businesses, our national secrets, and our private lives.

It all leads to an inevitable conclusion. Jason believes that chief compliance officers will become commonplace, even in small companies. Protecting data is going to become a primary concern, for governments, businesses and people. Because, as the world gets more digital, we’re going to see more and more cyber attacks.

“Trends that I see happening are an increased awareness and investment in things like compliance and security. I think that if companies don’t have a chief compliance officer now, they likely will in the future,” Jason said. “I think it’s interesting when you see the geopolitical environment of how we might have to invest in more sophisticated tooling for national security. But more than that, it’s like understanding that we’re no longer a single micro-geo unit called the United States.”

- On the Dev Interrupted Podcast at 11:03

2. Companies will focus on loyalty and subscriptions over one-off sales

The standard business model is outdated. In the past, technology companies sold software, they gave customers the software and that was the end of the transaction. But now, it’s more about building communities and regular interaction with your customers. It’s about subscriptions, regular payments or even donation models, seen on popular platforms like Twitch. Software isn’t a product any more. It’s a service.

But almost every company these days is a technology company. Just look at what’s happened to the taxi industry. The model has completely changed, simply because the technology has evolved. The old model won’t completely disappear, but we’ll see more and more industries move into a subscription model as new technology takes over.

“Selling is about adoption first and selling second. Someone’s got to reach for you first,” Jason explained. “Then, they’re going to find a value problem, then they’re going to want to give you money if they’re finding utility out of you.”

- On the Dev Interrupted Podcast at 11:21

3. Hardware is, and always will be, just as important as software

With every new innovation, we place more demands on the hardware we’re using. The more advanced our software becomes, the more powerful our hardware must be. But right now, most  companies rely on international trade to build key components. With tensions rising, it’s likely that we’ll see companies begin to bring these resources closer to home, securing their supply chain in the process.

“There’s interestingly a lot more emphasis on investing in hardware again,” Jason said. “And America in particular owning its hardware manufacturing, which I think is obviously good.”

-On the Dev Interrupted Podcast 11:41

Watch the full interview

If you’re interested in what else Jason had to say about the next ten years, and what challenges society faces, you can watch the full podcast on our site.

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Chaos Engineering might sound like a buzzword - but take it from someone who used to joke his job title was Chief Chaos Engineer (more on that later) it is much more than buzz or a passing fad - it’s a practice. 

The world can be a scary place and more and more companies are beginning to turn to Chaos Engineering to proactively poke and prod their systems and in doing so are improving their reliability and guarding against unexpected failures in production and unplanned downtime. 

During my career I dealt with my fair share of outages, including one that caught me mid-song during a bout of karaoke and far too many that woke me up at 02:00. As the co-founder and CTO at Gremlin, I do my best to make sure no other engineers have to suffer sleepless nights worrying about their product. 

But the question remains, what is Chaos Engineering and where did it come from?

A Short History

The spiritual predecessor to Chaos Engineering is often called by a much more widely recognized name - disaster recovery. The focus when this practice was introduced is much the same as today: proactively suss out production problems by injecting failure. 

Netflix’s Chaos Monkey is probably the most well publicized Chaos Engineering tool as it arguably kickstarted the adoption of Chaos Engineering outside of large companies, but this has led to the erroneous belief that Netflix invented the practice. In fact, the practice was already widely in use amongst the titans of technology. 

Over a decade ago during my time as a Lead Software Engineer at Amazon, we implemented several crude practices designed to inject failure into our systems. The most rudimentary of which was employed by a man called Jesse Robbins, who earned the nickname “Master of Disaster” by running through data centers pulling out cables. 

Let’s just say the practice has evolved a lot since those early days and your data center cables are much safer these days.

What is Chaos Engineering?

“What Chaos Engineering really is, is the art, if you want to call it that, of introducing controlled chaos.”

- 2:16 on the Dev Interrupted podcast

At its core, Chaos Engineering is a disciplined approach of identifying potential failures before they have an opportunity to become customer facing outages. 

It is a practice that lets you safely test your assumption about how your systems will behave under duress by actually exercising resilient mechanisms in a controlled fashion. You literally "break things on purpose" to validate and build resiliency. The end goal of Chaos Engineering is not to inject arbitrary failure into a system, but rather to strategically inject turbulence to enhance the stability and resiliency of your systems.

How Chaotic is Chaos Engineering?

I always tell people that Chaos Engineering is a bit of a misnomer because it’s actually as far from chaotic as you can get. When performed correctly everything is in control of the operator. That mentality is the reason our core product principles at Gremlin are: safety, simplicity and security. True chaos can be daunting and can cause harm. But controlled chaos fosters confidence in the resilience of systems and allows for operators to sleep a little easier knowing they’ve tested their assumptions. After all, the laws of entropy guarantee the world will consistently keep throwing randomness at you and your systems. You shouldn’t have to help with that.

How do I Start?

One of the most common questions I receive is: “I want to get started with Chaos Engineering, where do I begin?” There is no one size fits all answer unfortunately. You could start by validating your observability tooling, ensuring auto-scaling works, testing failover conditions, or one of a myriad of other use cases. The one thing that does apply across all of these use cases is start slow, but do not be slow to start.

What I mean by this is to start testing across just a few nodes versus impacting your entire fleet. We refer to the impacted area as the “blast radius” and we highly recommend starting with a small blast radius (the number of systems impacted) and increasing it over time.

By starting small you allow yourself to gain confidence in both the experiments you are running and your systems. Of course your risk tolerance is also a factor of how large a blast radius your organization will use. 

For instance, a large banking institution with millions of customers has a much lower risk tolerance than a tech startup with a couple hundred customers. In that case, they would want to run experiments in a programmatic way and would need to be very explicit about communicating to the rest of the organization what tests are going to be run and when to avoid any unplanned 2am or 3am disasters. 

Eventually you want to get to the point where all of this is automated, a process we refer to as “continuous chaos.” Starting small with automation could be something as simple as taking out a single node; then taking out five nodes; then ten; and so on. Eventually you automate the process at a level you are comfortable with.  

“Ultimately you want to be able to handle any of this random chaos being thrown at you, because that's what the world is, it's entropy, it's degradation”

- 7:35 on the Dev Interrupted podcast

No Tolerance for Downtime

When I founded Gremlin, it was just myself and my co-founder developing the first iteration of the product. The business looked very different then and I jokingly referred to myself as the “Chief Chaos Engineer” responsible for implementing code that was mostly used by enterprise companies. Many of these companies came to us because they had reliance thrust upon them by the US government or they had top-down reliability standards and they wanted a tool to help them shore up their systems. 

As the company began to evolve, so did the customer base. These days it’s not just Fortune 500 companies that care about reliability, it’s everybody. Planned downtime is a relic of days gone by. It is no longer acceptable to espouse planned maintenance windows as part of development lifecycles and customers don’t have the patience for products they rely upon to spend any time unavailable. Companies recognize this dynamic - and it’s not a hard one to miss. 

Seemingly our appetite for technology has gone up exponentially while our ability to stomach downtime has drastically decreased. Customers expect that your product is always working, always running. If your product is down because of outages then there are ten other similar products waiting in the wings to take their money. 

Making Lives Better

Visibility is high these days and companies don’t need the publicity that comes with making any unforced errors, let alone to be subject to errors not of their making. No one wants to be blown up on Twitter because their product isn’t working or because one of their downstream dependencies or their cloud provider had an unexpected outage. 

By preparing for the worst, we can be at our best as an industry and can be prepared when disaster eventually comes knocking. That’s why when an unexpected outage occurs or there is a production failure customers will never even know it happened. 

I often joke that we are the engineers’ engineers because many of us know that feeling of being jolted from a dream at 03:00 by our pagers, groggily wiping our eyes and whipping out the laptop to go dig through a sea of monitoring dashboards and logs. It’s not fun and it’s exactly why I founded Gremlin. Because there is a better way to approach operations than merely sitting back on our haunches and waiting for the next outage. Chaos Engineering not only helps to protect against the randomness of the world, but also teaches people how to build more reliable software. And if enough people build more reliable software, we build a more reliable internet.


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Continuous Delivery isn’t about how fast you can deliver, it’s about the outcome your delivery achieves. Bryan Finster, author of the 5-minute DevOps series and founder of the DevOps Dojo, joined our Dev Interrupted Discord community to answer your questions about outcome-based development, continuous delivery, and why failing small is better than failing fast. 

Bryan is currently a Distinguished Engineer at Defense Unicorns but has also worked for Walmart as a systems analyst and eventually became a staff software engineer for Walmart Labs. He had previously appeared on the Dev Interrupted Podcast to further talk about these subjects as well as the most common pitfalls dev teams find when trying to optimize their delivery process. Listen to the episode here:

This Community AMA took place on January 8, 2021 on the Dev Interrupted Discord.

Necco-LB: 📢📢 Community AMA📢📢   @everyone 

Topic: Outcome-based Development with @BryanF (Bryan Finster)

Bryan, thanks for joining us today!

Bryan Finster: Thanks for having me!

col: Bryan... great quote. "A developer is a business expert who solves problems with code." Thank you. Tremendous concept.

Bryan Finster: Thanks. That's who we are. We aren't Java spewing legos. If we don't understand the business, the code won't.

Rocco Seyboth: YES!! @col Love it. @oriker says "a business decision is made with every line of code"

Bryan: Exactly. How does this change improve the bottom line. Even more, how does it improve the lives of our customers?

Necco-LB: We really enjoyed having you on the podcast to talk about Outcome-based development and what continuous delivery should be trying to achieve. I was hoping you could explain to use what Outcome-based development means?

Bryan: It's just focusing on the outcomes. It's pointless to focus on how we do things if the outcomes are poor. It's also about Hypothesis Driven Development. The act of defining the expected value before we attempt to deliver it and then measuring for that value. Instrumenting the application to see how close we get so we can adjust. I frequently see people just being feature factories, pounding out changes that no one needs. That just costs money and increases support. We should be deliberate about what we do and say "no" when the value isn't obvious.

Cocco: When it comes to delivering value to the customer sooner, what things do you commonly see teams worrying about that they perhaps shouldn't (or not worry about, when they should?)

Bryan: "I can't release this! It's not feature complete!" No, get the incomplete change out there and make sure it doesn't break anything.

Necco-LB: You mentioned during the podcast that Pride is the best metric ever. Can you explain that a little bit?

Bryan: If I own the business problem, own the solution, own how to make it better, own the outcomes and see people getting value from my work, then I have pride in what I do. I want it to be good. I want it to be secure and stable and I want to continuously improve it.

Necco-LB: When you talk about outcome-based development you often talk about the things that need to happen before hands touch the keyboard. What are some of those things?

Bryan: We need to understand the value we are trying to deliver and we need to define how we expect to deliver that value at the detail level. It's not enough to write a vague user story. We need testable outcomes that we agree should deliver that value. Behavior Driven Development is the most effective tool I've found for that. We also need to make sure we aren't trying to deliver ALL of the value at once. What if we are wrong? We usually are, statistically. So, what is the smallest, highest value thing we can deliver to find out? Sometimes the right answer is to stop at that point. Invest in the outcomes, not the plan or the work.


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Dev Interrupted Discord, the new faces of engineering leadership

Cocco: What patterns/trends do you see in teams who can deliver the outcomes they want? (Are there common factors in teams you've seen that move from struggling -> successful?)

Bryan: Yes. Actual continuous delivery and product ownership. They can deliver small changes daily and they have ownership of what those changes are. They have the safety to challenge things without fear and they are not pushed so hard that there is no time to think of better ideas. Software development is a mental activity, not typing.

Necco-LB: You work with a lot of different teams at the DevOps Dojo. What are some of the most common pitfalls preventing a team from optimizing their delivery process?

Bryan: They are given the wrong problems to solve. They are asked to solve stupid problems like "how many changes did you make today?", "How many stories did you complete this sprint?", They don't know how to work as teams because they are incentivized to work in silos. So, requirements are poorly defined, testing suffers, speed suffers. They need to be solving the business problem. What is measured will change. Be careful what and how you measure.

Necco-LB: What are some first steps a team can take if they want to become more outcome focused?

Bryan: Focus on the business problem and get close to the user. Empathize with them and what value they need. This really applies to anything. If you don't respect your customer, you won't need to worry about them for very long.

Necco-LB: What is the role/responsibility of the developer in this outcome-based development model?

Bryan: On a good development team you have engineers and product ownership. Engineers ship working solutions. They know they are working because they tested them, delivered, them and observed that their tests were accurate.

Rocco Seyboth: In 5 Minute DevOps you talk about observing what high performing teams do then modeling other teams to the same process and behavior... how do you reconcile that with the belief that every team is different and should have the flexibility to do things their own way?

Bryan: Actually, I advocate against cookie cutter templating of teams in that post. We should standardize on improving outcomes.

Necco-LB: Friends, that's just about the top of the hour. Bryan has a real job that needs to get done, but feel free to keep the questions coming asynchronously throughout the day - he'll be popping in and out to answer them. Bryan - thank you so much for joining our community today and answering our questions!

Bryan: Just some contact links to leave and I want to thank everyone for the conversation. I love talking about these topics.
https://www.linkedin.com/in/bryan-finster/

https://bdfinst.medium.com/


Starved for top-level software engineering content? Need some good tips on how to manage your team? This article is inspired by Dev Interrupted - the go-to podcast for engineering leaders.

Dev Interrupted features expert guests from around the world to explore strategy and day-to-day topics ranging from dev team metrics to accelerating delivery. With new guests every week from Google to small startups, the Dev Interrupted Podcast is a fresh look at the world of software engineering and engineering management.

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Putting employees and your community first should be a crucial priority for every organization, and it shouldn’t exist only in principle - it must exist as an actionable goal. Fostering a community within your team creates a foundation for high-performance, but it only works if you lead people-first.

At Stack Overflow, the level of collaboration between engineers is a step above any other organization I have seen. It takes conscious effort on the part of leadership to foster a work environment that puts employees first. Managers should choose to put people first, because it’s the right thing to do, not just a vague claim to a cliche. 

Thankfully, we live in a world where the data demonstrates that caring for people first is also the economic thing to do. No one has ever done a better job because they were scared, stressed, or worried about their future; especially in jobs centered around creativity and problem solving such as software development.

This commitment to people is the leadership philosophy behind Stack and helps guide our decision-making and our workplace culture. It also helped us to create Collectives™ on Stack Overflow. To get there, we needed a successful engineering team and culture - here’s how we built it. 

Indicators of team health

Common metrics that organizations tend to follow are often a symptom of a team’s performance, but not necessarily the whole story. Velocity, predictability, bug rate, etc should be viewed as an indicator of team health, not as a goal to be achieved; sometimes the best indicators to follow are subjective, and relative to the people and teams. 

After all, what does success look like? If people are getting what they need, agreed upon expectations are being met, and team morale is high, that’s real success. If this kind of people-driven success is occurring, you’ll start to notice that things like velocity time and predictability will naturally improve and not the other way around.

For the record, predictability should never be the goal. The end goal should always be to create value for your customers and/or your community. Any team - or manager for that matter - can make predictability look good if they are making sure that they never fail a given estimate on paper, but that’s not an indicator of good product creation.

If you're actually producing value, and you have a well run team, predictability will follow. It's a side effect, a symptom of good team health. 

Servant Leadership

At Stack Overflow, we’ve had long talks about what metrics we feel provide valuable feedback and those we believe are valuable to track. Numbers are important and should not be ignored, but again, they should not be the standalone goal. Tracking the right metrics should facilitate introspection for your organization and leaders would do well to keep this in mind. If we have a bad sprint, it tends to trigger us to think, “what went wrong?” and “how can we improve this for next time?” instead of thinking this was a failure of certain individuals.

For instance, if you had a sprint where you achieved a really high velocity, you should celebrate that success. But at the same time, you should be asking yourself what led to that success. Was there a behavior that changed? Not everything is internal. Sometimes external factors, a pandemic as an apropos example, influence successful team metrics just as much as internal ones do. Remember to look behind the metrics to see what’s impacting team members.


As far as following specific methodologies is concerned, try not to get hung up on the little things; analysis paralysis occurs is often a huge drain on performance and focus of the team. Time spent sitting around and arguing about whether something is a three point or a four point story is not productive. Call it a four and keep moving. Good leaders should keep their developers developing, while removing any hindrances to their performance, ideally before it is even on their radar.

Building a team and your product

If you’ve been around software development long enough, I’m sure you’ve had the experience of joining an organization where everything is dictated in a top-down approach. This kind of “my way or the highway” thinking ultimately undermines your teams and makes your organization rigid in an industry that is far more creative than some like to admit. 

A good manager will do their best to accommodate their teams, even if that means allowing a team to communicate or operate in a way that is not established within an organization. Recently, one of my most productive teams started to struggle after the project we were working on started to shift. A lot of the QA and code review work associated with the stories became large and unwieldy and the common practice was to have that wrapped in with the dev story. That makes sense after all, the former can’t ship without the later. Eventually we just tried separating out the more cumbersome tasks into their own stories. The immediate and biggest reaction was from folks overly invested in the metrics: we just doubled our stories and made it appear that story cycle time virtually doubled. The instinct was to say “this is a step backward. Undo it all,” but that would be ignoring what's going on behind the metrics: more work was getting done, and the bug count dropped. As those were saying we need to go back because the metrics showed team health was bad, my response was to just change the metrics to accurately reflect our healthier team that chose their own workflow.

Adopting this mindset as a manager provides huge returns for your organization. People are happier when they are not being forced into something that doesn't fit. With team members that control how they work, on their own and especially with each other, comes higher value creation.

Work-life Balance

I have never met anyone that works better when they’re worried about what’s going on in their personal life. I’ve found this over and over in my career as a developer and eventually a manager inspired me to write about it. People who are under stress feel strained to come up with strong solutions and tend to generate less errors. Those people who say “this person just works well under pressure” are really just saying “This person's performance doesn’t fold as much as others once emergencies happen.” That's a good quality for them, sure, but nothing an team should brag about; that should be embarrassing that it happened enough that some people have reputations around crises.

Work-life balance is not something a company sacrifices, that’s zero sum thinking. It’s been shown time and again that the opposite is true. Providing people with things like leave, and an investment in their mental health has more for an organization’s productivity than filling out timesheets ever will. At Stack we have a policy of unlimited sick days, no questions asked. If you need a day, we trust you to be able to take care of yourself. 

When you take care of people they will work better and faster - that’s also what they want to do. Regardless of the stereotypes people will often hear from naysayers who balk at the idea of unlimited sick time, the folks who just want to phone it in and game the system are the minority. So much so, that spending the effort considering how to manage the time a person takes a sick day when they aren’t sick is probably more of a time sink than how much it will happen. 

By choosing to be invested in your people’s health, an organization chooses to be a place that values its employees. When you avoid zero sum thinking, getting trapped in the idea that if employees are benefiting the company must be losing, you begin to realize that working with, instead of against, those you represent leads to happier people and a better bottom line. 

We took all these leadership principles and applied them to Collectives

At Stack Overflow, we’re quite a flat company. And I don’t mean this by measuring the number of levels between an engineer and the CEO (it’s 4, for the record), but people of all levels have a voice in product decisions. Engineers are heavily involved in what we build and how it is built. Being a company built for engineers and driven by engineers is a huge part of why Stack Overflow is successful. 

This success has allowed a beautiful community to thrive on our public platform, but we are always looking at how best we can give back to that community. How do we help our community grow? How do we make those experiences more meaningful? Those are the questions that guide us at Stack. 

“Anything that fosters our users’ ability to help each other and to benefit from it. That's always a homerun.”

- from the Dev Interrupted Podcast at 34:54

With that in mind, we’ve launched Collectives, a new way for the community to interact with the maintainers of the technology they use most. 

As I discussed on the Dev Interrupted Podcast, Collectives are dedicated spaces on Stack Overflow where you can find the resources (including questions and technical articles) and trusted answers you need, faster, by centralizing that content and connecting you with the product experts and trusted users. For instance, if you have questions about Google Go, you can get answers directly from those who help maintain the language.


I am extremely proud of the work that went into this, and the work that we continue to do to make it something our users can enjoy. Like all new adventures, there is a constant feedback loop we work through to try and keep making Collectives, and Stack Overflow, a better and more welcoming place. 

It is still the Stack Overflow you know and love

The Beta release of Collectives was a huge success. We’ve seen over 20,000 users join Collectives on Stack Overflow and start collaborating since the launch in June. That said, we know we don’t have a Collective for everyone (yet). For users that don't want to take part, or haven't found a Collective that they're excited about yet, their Stack Overflow experience is not going to change.

For instance, we're not changing accepted answers, whether it comes from Google (our new partner) or not. If people don't vote for an answer, it doesn't get accepted. Content moderation will be treated the same way. Moderators will interact with content from sponsored users just like they would anyone else. 

“I think the most positive thing about it is that people aren't losing the site that they love, and that we're really proud of.”

- from the Dev Interrupted Podcast at 33:22

With our community update, organizations will be able to improve the visibility and detail of content being created around their technologies, and users will be able to find more relevant and accurate answers they can put to use solving problems while being better recognized for their contributions. Ultimately providing both organizations and users with more actionable insights. 

These efforts allow Stack to build better communities because after all that’s really what we do: we are in the business of building communities. 

Collectives do just that. 


Starved for top-level software engineering content? Need some good tips on how to manage your team? This article is inspired by Dev Interrupted - the go-to podcast for engineering leaders.

Dev Interrupted features expert guests from around the world to explore strategy and day-to-day topics ranging from dev team metrics to accelerating delivery. With new guests every week from Google to small startups, the Dev Interrupted Podcast is a fresh look at the world of software engineering and engineering management.

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Grammarly has a simple but ambitious mission: to improve lives by improving communication. Every day, our AI-powered writing assistance helps 30,000 teams and 30 million people communicate clearly and effectively wherever they write.

But behind our technology is a team of engineers. Until recently, our engineers focused exclusively on building a product for consumers. When I came aboard to lead new initiatives as the Director of Engineering for Grammarly Business and Grammarly for Developers (expanding our product to support teams, organizations, and third-party developers), it was clear Grammarly approached full-on hypergrowth.  

Then the pandemic changed everything. Suddenly, we found ourselves transitioning to a remote-first organization amid hypergrowth hiring and onboarding. The company doubled in the past year to over 500 team members, and my teams have grown even faster. 

To be successful, we needed to spearhead initiatives that solved two problems. The first involved people: How could we successfully maintain a culture reflecting Grammarly’s EAGER values in a remote world? The second was technical: What tools and practices would enable our team members to thrive? 

Transitioning to remote

Historically, Grammarly has had an in-person culture. We have four hubs—in Kyiv, San Francisco, Vancouver, and New York. But when I joined in July 2020, everyone was remote. Few assumed it would stay that way, but the “return to normal” kept getting pushed further back. Eventually, Grammarly adopted a remote-first hybrid model

With “remote-first,” Grammarly team members work primarily from home. However, we continue to believe in-person interaction builds trusting relationships and a supportive culture that fosters innovation. So our offices became collaboration hubs where face-to-face meetups will also take place each quarter.  We made this decision based on our progression as a company; because we felt we’d learned how to communicate and collaborate effectively and saw advantages to the remote-first model.

Keeping it personal 

I look forward to meeting people in person at our first team-based meetup next year, but with my quickly growing team split between Kyiv and North America, we need to constantly build and maintain personal connections.

“I've onboarded fully remotely. I've only met four of my coworkers in person.”

- Dev Interrupted podcast at 19:33

Thus, we’ve tried our best to foster a thoughtful approach to team bonding at Grammarly—which signals that breaks and fun are important, too. 

Some example approaches: 

Our events motivate people to break from work and connect with each other. Activities range from educational to creative and silly, including an Indian cooking class during Diwali, a graffiti workshop, a cocktail class, a Halloween costume competition, and Grammarly’s twelfth-anniversary talent show. This personable approach also translates to how we chose the tools for remote collaboration.

Finding the proper tools

Setting hypergrowth teams up for success requires investing in the right tools and processes. As often as possible, we try to implement asynchronous communication and development best practices. Proper tools that facilitate organizational transparency are critical for alignment in a remote-first company.

Fewer people are required in Zoom calls because we share recordings and notes in open Slack channels. For collaboration and stakeholder alignment, our Engineering teams use Confluence for documentation, Jira for issue tracking, and Figma for collaborative interface design. Architecture and whiteboard sessions occur in Miro, while team retrospectives happen in Parabol

The archival component of these tools is invaluable; new and old team members alike can discover information through Glean, which gives us aggregated search across all our tools and content. 

Embracing the talent diversity potential of remote work 

One of the most exciting opportunities with remote work is in finding hidden talent in overlooked geographies. Silicon Valley gets all the attention, but it’s not the only region with great software engineers. There’s plenty of talent out there just waiting to be found. 

“Genius is evenly distributed by Zip Code, but opportunity is not”

- Mitch Kapor, Kapor Capital

Finding talent in other locations also leads to more organizational diversity. Whether that diversity is racial, ethnic, socioeconomic, or generational, diverse teams are going to improve your product. I’m a huge believer in diverse teams for two reasons: 

  1. Better problem-solving than homogenous teams: I’ve witnessed this in my career, and it’s been proven with studies. Creativity naturally flows from visible and invisible diversity. Companies embracing differences will achieve better outcomes because the ensuing creative conflict helps you innovate and build better products. 
  2. Stronger empathy for the customer: In Grammarly’s case, building writing assistance for the world’s 1 billion English speakers makes diversity in engineering critical. For example, those speaking English as a second language often visualize the language differently, leading to feature ideas that wouldn’t occur to primary English speakers. 

You need a diverse team to build the right product for a broad audience. We’re excited to use recruiting tools like SeekOut and partner with organizations like Elpha and AfroTech to help us connect with and hire engineers from underrepresented groups. 

Onboarding

But hiring isn’t enough! Many organizations are too focused on hiring, at the cost of onboarding. How we onboard folks and make them feel welcome is critical to their long-term success at Grammarly. 

A small test of our onboarding process is whether new engineers can push code in the first week. If they can, it’s a signal the dev environment is well documented and has minimal friction. The faster people can be productive, the more confident they feel, which ultimately boosts team morale. 

That said, onboarding is about more than pushing code. Engineers are encouraged to meet people and learn the product before they feel pressure to deliver. New engineers have a Getting Started Guide that includes who to meet and links to resources. Managers check in daily to answer questions. They also pair with a non-engineering Culture Buddy plus a mentor from their team so they can get to know all aspects of Grammarly life. 

Thoughtful onboarding during hypergrowth helps new team members build connections, which leads to better team health in the long term. 

Staying Grounded 

My advice to any organization about to engage in hypergrowth is to remain thoughtful. Think about hiring, onboarding, your processes, how you measure success, and how you want your employees to feel when they join your team.

Remember, too, that diversity is more than a checkmark or an abstract goal. Diverse teams will be your strongest asset. They will push creative boundaries—and in doing so will build the best possible product with the best possible outcomes. 

_

Want to join us in helping 30,000 teams at thousands of companies succeed through effective communication? We’re currently hiring for roles across the Grammarly Business and Grammarly for Developers teams.

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Dev Interrupted Discord, the new faces of engineering leadership

There is very little formal guidance for new engineering managers. When I first moved from an individual contributor (IC) to an engineering manager (EM), I found myself struggling to find training resources. 

I want to change that - and I hope this article will serve as a small start in that direction. As an engineering leader at Mark43, I do a lot of mentorship and coaching for engineers who aspire to move to engineering management and early-tenure engineering leaders. Here are a couple of initial focus areas that a first time EM can build upon.

Focus Area 1: Trust, Collaboration and Communication

As a new engineering manager, your first 90 days are crucial. You quickly realize the need to gain trust while rapidly building relationships and rapport -- not only with your colleagues and your direct reports, but also with all the other discipline stakeholders. As an engineer, you spend 80% of your time with your engineering team, focusing on the engineering aspects of your role. But in a management position, you spend perhaps 50% of your time with your fellow engineers. The other 50% of your time is spent with people who are stakeholders representing cross-functional disciplines such as product, design + UX or the QA department if there is one. 

In addition, there are other teams like people ops, recruiting, platform, customer support, customer success and deployments. Hence, you need to build relationships early on because to achieve collective success your team needs each discipline aligned to a common goal.

Focus Area 2: Information collection, compartmentalization and sharing

As an engineering leader, the amount of cross-communication and information that will be made available to you will rise exponentially. Whether that is pre-set routine meetings, ad-hoc situations or some form of change management – there will be a plethora of details that you will hear, will need to act upon or will need to pass around within your team. These new job duties  will become your day-to-day reality as an engineering manager.

To succeed, you should have a structured way to capture all the information that you are going to be exposed to throughout the day. Unlike pre-COVID times when in-person collaboration allowed us to get away with not thinking about some collaborative processes, you now need to be intentional about your remote organizational design to drive collaboration and communication. So for example, if you are in a one-on-one and you hear something of interest, you need to be able to make the connection that maybe this is something that I should bring to the wider group, or this is a follow-up item for me to take action upon later. You need to make sure that you are staying on  top of all your conversations.

 The takeaway here is that becoming an active listener is a crucial skill for an engineering manager. Being a good listener is not enough because the role of an EM is to surface key information both from your team and for your team. 

Being situationally aware is also important. This skill will help your future self when you need to recall something a day or week later. There are so many different people and so many different topics of conversation that occur everyday that it can be difficult to keep everything straight. I recommend keeping some sort of documentation or making an immediate action item list. This simple habit will pay dividends with time. There are lots of different note and action item taking systems - find the one that works for you.

To wrap things up, here is my simple 3-item checklist to improve your first 90 days as an EM:

  1. Observe and adapt vs be rigid and impose
  2. Build connections and gain trust early on
  3. Stay technical but do not spend a lot of time implementing technical solutions

If you keep this checklist in the front of your mind as well as keeping your eyes and your ears open, you will excel at being an EM. A good EM understands that their measure of personal success is their ability to foster team success - and team success is only possible with trust, collaboration and communication. 

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Dev Interrupted Discord, the new faces of engineering leadership