What do I do with my time?

Question:

I'm a new manager, new to both the company I work for and to management. When I joined this company there were several fires for me to help put out, and every day I was busy dealing with one urgent task or another. But now I'm drifting. My boss doesn't have time to tell me what to do, I don't have any features that I am responsible for, and no one is urgently requesting my time. What is my job, now that things are no longer on fire?

Ah, yes. One of the challenges of management that we don't often talk about is those times when you have no clear urgent tasks. Engineers deal with uncertainty in relatively bounded forms, such as, how should I break down this big project into smaller chunks, how should I architect this system, who should I talk to for information about this feature, what library should I choose? These are enough to stymie some, but usually by the time you've been working for a few years you know how to get started on these types of problems.

Management, however, is a different beast. Management is like being in operations. Operations engineers must balance a series of ad hoc needs (system configurations or permission granting, say), with fires (outages), and long-term strategic projects (moving to a new data center, upgrading a major piece of critical infrastructure). As a manager you also have regular ad hoc needs (1-1s, meetings, small decisions) and fires (hiring, firing, projects in trouble, outages). And you have long-term strategic projects (planning for the team growth, thinking about the next quarter's goals, anticipating future obstacles). Like operations engineers, many managers get really good at the ad hoc and the fires, and really bad at the long-term strategic projects. It's much easier to do things right in front of you than it is to think abstractly about unclear topics.

When faced with the blank slate of empty time and no obvious deliverables, what can a manager do to make the best use of that time?

As a new manager to a new company, downtime is a good chance to learn the existing systems. Learning things that you aren't actually working on can be really challenging, so if it's feasible you might find small bugs to fix or minor improvements to build, things that aren't urgent (in case another fire crops up) but that will give you the feel for working in these systems. You can also use the downtime to meet with other teams that your team works with, learn about their projects and challenges, look at what they're busy with. Lend a hand to their managers, or help your boss fill that gap if they don't have one.

At some point, though, you will have gotten comfortable with the teams, the code, the projects, and you'll still find yourself with downtime. This is the chance to flex your strategic thinking. Take a bigger-picture look. What are you not doing that is important, but not urgent? Maybe it's planning for reviews next month, setting up a team dinner, doing some proactive outreach to candidates you may want to hire in six months, or finishing that presentation that you have promised to give on testing but keep putting off. What are the recurring problems your team is having? What is not going smoothly? What could you be doing to resolve that? Remember, part of your job now is to define what work needs to be done. Your boss won't always be able to tell you what to do, and she probably expects you to tell her what needs to be done. Use this time to answer that question.

Sometimes we put downtime to use in bad ways, and I don't mean procrastination. There are times when the best thing you can do with downtime is take a breath, check in on the internet, watch a talk you have been meaning to see. All of that is better than using downtime as an excuse to make work for other people, which can happen if you're not thoughtful. If you use your downtime to half-bake a feature and throw it into prod for your team to support, that is harmful. If you use your downtime to wander around and interrupt your engineers who are busy working, that is harmful (and yes, I'm guilty of that sometimes!).

You are responsible for finding productive uses of downtime, and part of that is resisting the urge to meddle, micromanage, and distract your team just because you don't know what else to do. Is everything going ok? Are your teams productive, getting things done, working on the right stuff? Great! Use your time to think about the future, write a blog post, catch up on small unfinished errands. Don't worry, there will be another meeting, another fire soon enough. Enjoy it while it lasts.

Vision and Trust: External and Internal Leadership

Fred Wilson recently wrote a post where he defined leadership as this:

It is charisma, it is strength, it is communication, it is vision, it is listening, it is being there, it is calm, it is connecting, it is trust, faith, and belief

Trust, faith, and belief. These are all words for the same thing, right? Well, not exactly.

I have observed that many leaders, especially the ones called visionary, are often evaluated in the court of public opinion on the following subset of those qualities:

Charisma, strength, communication, vision, connecting, faith, and belief

Listen to them talk to a crowd and they will blow you away with the clarity and strength of their vision, with their ability to connect with their customer. This in turn translates to a level of faith in that vision and belief in the overall direction that they are guiding their company towards. Awesome. Literally, awe-inspiring to witness. These are the public qualities of leadership that show up in the media, that the whole company can see in an all-hands, that you can see firsthand when they speak at a conference. These are the qualities that the board members see, that the venture capitalists invest in, and it is pretty hard to get into the position of successful startup founder without them.

So where do the rest come in? Listening, being there, calm, trust. These qualities are more difficult to evaluate based on an interview or a presentation, these are the “internal” signs of leadership.

Trust is a contract between two people. You are constantly creating and building trust in a long-term relationship with everyone around you. When you listen, and are there for people, and are calm when interacting with them, you build trust. But without that listening, without “being there” in a way that lets people feel the ground beneath their feet, without calm, trust is fragile or non-existent. Trust is regularly tested and negotiated based on our ability to show up. I would say that these more private qualities, these relationship qualities, are the qualities of management that every great leader must possess. Managers know the value of steadiness, of showing up for that 1-1 every week, of reacting slowly and listening to the people around them.

So even great external-facing leaders need some management skills. What about the managers?

Managers fail when they lack communication, connecting, and strength. A manager who can’t communicate with their team cannot execute effectively. A great manager connects with their employees as human beings (without turning into full-time therapist), and has the strength to shoulder the challenges of making hard calls in the trenches with their teams, the firings, the resignations, the projects being cut and the delivery or missing of deadlines. The day-to-day pains are very real for the manager and without strength it is almost impossible to do the job well.

But what about vision? We think that vision is the realm of the strategist, but vision also has a place in the manager's skill set. Instead of business strategy or architectural future, the manager’s vision sees what their organization looks like in 2 years, what their team can grow to be capable of accomplishing, what the successful day to day looks and feels like for the employees on their team.

As a final data point, my former CTO coach and one of his partners wrote about the Management/Leadership split in their new version of The Art Of Scalability, excerpted here. Between these three sentiments, perhaps you can triangulate your own path to being a great leader who manages enough, a great manager who leads enough, or whatever the situation calls for.

Entrepreneurial Gap

I recently came across a blog post that mentioned an intriguing concept, the "entrepreneurial gap." The idea is straightforward: give people more accountability than they have the direct resources to accomplish.

In many organizations employees are generally held accountable only for things fully within their control. So while the CEO has both all the resources of the company and the ability to make decisions that cause major tradeoffs (sacrificing profit for growth, for example), a manager of a team is only given projects big enough for that team to accomplish and goals big enough for that team to meet.

The entrepreneurial gap comes in when you give people bigger accountability than they have the direct ability to execute against. This is in many ways the classic startup move. You hire people and give them enough freedom to accomplish whatever they can manage to accomplish. Because early startup employees tend to be very entrepreneurial they often find a way to do just that, to gather support from other people in the organization and align efforts to produce outsized results. I think this is an important element of a growth business, something that inspires great people to work for a company, and produces a really fun culture to work in.

But, there's a trap.

The entrepreneurial gap works incredibly well when you give teams aligned goals. If you read the first case studies in the paper, you will see that in all of the examples the CEOs focused the company on a few goals, and in fact in all three examples there was a very strong emphasis on the customer. In companies where everyone is working ultimately towards the same goals, the entrepreneurial gap is awesome because it encourages people to work together and identify opportunities and efficiencies, especially cross-functionally, that may otherwise be lost.

Unfortunately, it is just as common to see companies put in place both an entrepreneurial gap and too many or misaligned goals. When you are in direct competition with your peers for scarce resources and you are not going to be graded on the same outcomes, the entrepreneurial gap produces a toxic environment of politics and power plays. Perhaps the best idea sometimes wins in these situations, but more often the best political players rule the day.

So what do we take away from this?

Organizational alignment is important because it lets you successfully ask more from people than the resources they have at hand. Without organizational alignment, you get political maneuvering. Without stretching people beyond their direct control, you get a lack of collaboration and creative cross-functional engagement. Set the right priorities and give people the freedom to stretch to them, and you will see the full potential of your organization come to life.

(The paper again: The Entrepreneurial Gap: How Managers Adjust Span of Accountability and Span of Control to Implement Business Strategy)

Get Curious

The best advice I’ve gotten in recent years is simple. Get Curious. For those of you who don’t know me personally, I can be rather aggressive, especially with things I don’t trust. Whether by virtue of personality or experience, my instincts always lead me to attack and take apart the unknown. This is in some ways a good trait in an engineer, after all, the unknown is what causes you to get paged at 2am. Unfortunately, when it comes to interpersonal interactions, aggressively looking for flaws in things you don’t understand looks less like smart defensive behavior and more like obnoxious trolling.

So how can one honor the need for clarity without attacking and picking apart things in a way that causes others to get defensive? The tactic I’m using is “Get curious.” Instead of assuming that the other party hasn’t thought of your objections, try to understand deeply the context in which they are making their statements. Why do they seem to want to do something that may sound illogical to me? What is their perspective on the circumstances? What have they tried to do already?

A few years ago I wrote about “Yes, and...” I won’t lie; I still struggle to this day with “yes, and”. For me, “get curious” is a bigger picture version of "yes, and," one that I find easier to keep in mind. If you’re always curious and looking for the context, you’re open to the possibilities that are out there. The possibility that you’re missing something important. And that openness makes people want to work with you.

“Get curious” could be the mantra for the learning organization. Curiosity in the face of failure, instead of blame, leads to a safe environment for people to fail, and lets us discuss our failures. Curiosity leaves us open to new ideas. Curiosity enables us to recognize our differences and embrace them to create a stronger whole.

So for those of you who are quick to blame and judge and want to get out of this habit, get curious. For those of you who feel like your team is afraid to take chances and fail, get curious. Even for those of you who are afraid that you’re being too nice and are not challenging your team or colleagues enough, instead of getting mean or aggressive, get more curious. You’ll be surprised at how much more effectively you can create change when you approach situations with open curiosity.

On the role of CTO

I get asked frequently to define the role of CTO, and I thought I would share some of my thoughts.

First, let's start by talking about what a CTO is not.

1) CTO is not an engineering role. CTO is not the top of the technical ladder, it is not the natural progression for engineers over the course of their careers to strive to achieve. It's not a role most people who love coding, architecture, and deep technical design would enjoy doing.

2) From 1, it follows that the CTO is not necessarily the best engineer in the company.

Now, with that out of the way, what is a CTO, if not the best writer of code and natural conclusion of the engineering ladder?

The challenge with defining CTO is that if you look across the folks who hold that title you will see many different manifestations. Some are the technical cofounders. Others were the best of the early engineers. Some started at the company with the title, while others such as myself were promoted into it over time. Some became CTO after holding the title of VP of Engineering. Some focus on the people and processes of engineering, hiring/recruiting. Others focus on the technical architecture, or the product roadmap. Some are the face of the company to the outside technical world. Some CTOs have no direct reports, others manage the entire engineering organization.

In looking at these examples the best definition that we can make is that the CTO is the technical leader the company has in its current stage of evolution. To me, that is rather unsatisfying, and missing the hardest part of the job. I believe instead that the CTO should be the strategic technical executive the company needs in its current stage of evolution.

Strategic: Thinking about the longer-term, and helping to plan the future of the business and the elements that make that possible

Executive: Taking that strategic thinking and helping to make it real and operational by breaking down the problem and directing people to execute against it

So, what does a CTO actually DO?

First and foremost, a CTO must care about and understand the business, and have the ability to shape business strategy through the lens of technology. The CTO is an executive first, a technologist second. If the CTO does not have a seat at the executive table and does not understand the business challenges the company is facing, there is no way the CTO can guide the technology to solve those problems. The CTO may identify areas where technology can be used to create new or bigger lines of business for the company that align with the overall company strategies. Or the CTO may simply ensure that the technology is always evolving to anticipate and enable the potential futures of the business and product roadmap.

No matter what, the CTO must understand where the biggest technical opportunities and risks for the business are and focus on capitalizing on them. When you see a CTO focused on recruiting, retention, process and people management, that is because it is the most important thing for the technology team to focus on at the time.

Strong CTOs also have significant management responsibility and influence. This does not always mean that they are deeply involved in the day to day management, but part of maintaining your ability to shape the direction of the business and the business strategy is the ability to put people behind solving the problems you believe will impact the business. Other executives will have ideas and needs for technology. The CTO must protect the technology team from becoming a pure execution arm for ideas without tending to its own needs and its own ideas.

Things get tricky when the team grows to be very large, and the CTO starts to hire VPs to manage all the people. Many CTOs give up all of their management responsibilities to their VPs, sometimes going so far as to not even have the VPs reporting to them. It is incredibly difficult to maintain influence and effectiveness as an executive with no reporting power.

I saw this clearly at my previous employer, where the most senior members of the technical staff in large business areas would often hold the title of CTO for that area. These people were always highly respected and technically capable. They understood the business and the technical challenges for the business, and were often called upon to help inspire the engineering team and help with recruiting.

Their downfall was that they often lacked the direct management oversight of any teams, and because technology was frequently viewed as an execution arm, they did not have much strategic influence.

If you are a leader with no power over business strategy and no ability to allocate people to important tasks, you are at best at the mercy of your influence with other executives and managers, and at worst a figurehead. You cannot give up the responsibility of management without giving up the power that comes with it.

The CTO who does not also have the authority of management must be able to get things done purely by influencing the organization. If the managers won't actually give people and time to work on the areas that the CTO believes are important, the CTO is rendered effectively powerless.  If you give up management, you're giving up the most important power you ever had over the business strategy, and you effectively have nothing but your organizational goodwill and your own two hands. Hope you're really a 10X engineer!

My advice for aspiring CTOs is to remember that it's a business strategy job, first and foremost. It's also a management job. If you don't care about the business your company is running, if you're not willing to take ultimate responsibility for having a large team of people effectively attacking that business, then CTO is not the job for you.

Special thanks to my editors Amanda Peyton, Cate Huston and EIC ChrisK.

Meaningful 2014: Everybody Hurts (notes on SparkCamp)

It is valuable to get out of your own head, and see what others are thinking.

It is even more valuable to get out of your own industry and see what others are struggling with.

This summer, I had the privilege of attending Spark Camp: Visionaries, Leaders, and Managers. Spark Camp is a gathering focused on media and newsroom folks that also pulls from external areas including the arts and technology, and I was invited to attend as a representative outside of media.

To be honest, on the first day I was rather intimidated. I am not a creative. I am not a writer, a media luminary. Everyone there had done so much. Here was the choreographer of a famous musical! There was the editor in chief of a major magazine! The mayor of a city! The writer of a blog I love and admire! The head curator of my favorite art museum! (hello, impostor syndrome)

The sessions started, and we talked about problems we faced as managers. The challenges of performance reviews. Managing people from different generations. Some of the notes I took include:
"Performance reviews as a measure of culture"
"Vulnerability inspires investment. Management is not performance art."
"Designers and engineers both define themselves often by their process"
"Conversation's role in creativity"
"Victim vs Player: Teaching folks how to be players" (more on this some other time)

My biggest takeaway was that we in tech think we are dealing with a special situation, a special workforce. Knowledge workers who have options, who can strike out on their own, who are temperamental and amazing and can change the world or give us migraines. We are not alone. In fact, people in the media industry (and beyond) deal with the same thing. Writers and artists are not all starving, and the talented ones have as many options as talented engineers.

Similarly, I'm not alone in feeling creatively stifled by the challenges of management. People with backgrounds in the creative arts discover themselves with leadership positions that offer little time, space, or appropriate opportunity for creativity. Finding that creative outlet is a universal leadership struggle.

I'm grateful for the opportunity to get some perspective on my own battles, and share my experiences with a diverse group of leaders. We often see writing on "impostor syndrome" and tricks for combatting it. Here's my trick: say yes to situations, and try to handle them with grace even when you feel completely out of your depth. Because under the surface we all struggle, and we all doubt, and sharing those struggles and doubts with strangers is sometimes the best way to free yourself from them.

The Best Decision I Made in 2014

Many people think that the role of leadership is decision-making. The desire to be the one who makes the calls drives some to climb the ladder so that they can become "The Decider."

I'm sorry to disappoint those who want this to be true, but in my experience the role of leadership is in fact to make as few decisions as possible, and to make the decisions that you are forced to make utterly mundane. Here are some of the mundane decisions I've made this year:
The first pass of a seating chart
Perfunctory approvals around uncontroversial hiring
Rubber stamping of well-thought-out architectural decisions
Signoff on budgets for vendor products we clearly need

I set up a lot of policies over the past few years. Some of them I've blogged about, for example, promotion committees. But I've also created policies around how new languages and frameworks are introduced, on-call rotations, even how we buy office equipment (oh the glamorous job of a CTO!). The goal of pretty much all of these policies is to make future decisions easier, and to empower various people on my team to make decisions without me.

So, I don't believe that good leadership is heavy on decision-making. That being said, you can't be a leader without occasionally setting a direction, which leads me to The Best Decision I Made in 2014. It started with a twitter conversation about continuous delivery, on January 3. I have been thinking about continuous delivery forever, and trying to move Rent the Runway in that direction for as long as I've been running engineering. At the end of 2013, we created a task force to make our deployments, then-weekly and taking up to 6 hours to do, faster and less painful. The team was well on their way to success by January 3. And so, inspired by my conversation, I sent this email:

Starting in Feb

---

Camille Fournier	Sat, Jan 4, 2014 at 9:40 AM
To: tuskforce
I want the one ring to release every day. Even if there's no user visible changes. Even if there's traffic. Even if it means we break things

That's it. I held my breath to see the responses. And as they rolled in, one by one, all of the engineers agreed. They were excited, even! So I started to tell others. Our Head of Product. My CEO. I told them "this might cause some pain, the first couple of weeks, as we figure out how to do this safely, but it's important." 

And so, come February, we began releasing every work day. And it was glorious. 

What made this decision so successful? What did I learn from this?

A great decision is often not a revolutionary move. We were doing the technical work to enable this already. The team wanted to be deploying more frequently. All I did was provide the push, to raise the bar just a little bit higher and express my confidence that we would easily clear it. 

The thing I learned from making this call wasn't anything about the decision itself. It was about the process that got me there. You see, this came about right after new year's, when things were quiet at work and I had some time to sit alone and think (or, in this case, tweet). All the sudden, I had ideas again! And it hit me: I need regular time alone, away from meetings and people, in a quiet room with a whiteboard. 

So I started blocking my calendar every Wednesday afternoon, and things started to change for me. In those Wednesday afternoons, I thought through the next evolution of our architecture. I thought through our engineering ladder, and our promotions process. I thought about problems I was having with people and how I could make those relationships better. I did some of the foundational work to create the 7 completely new talks that I wrote and delivered in 2014. I made time for the important but not urgent. In short, I grew from a head of engineering focused on the day-to-day into a CTO who thought a lot about the future.

The best decision I made in 2014 wasn't, actually, to tell my team to release every day. That's just the story I've been telling myself all year. The best decision, really, was to make time to think.

"Meritocracy" and the Tyranny of Structurelessness

Engineers like to believe in the idea of meritocracy. We want to believe that the best idea wins, that the person who produces the most value is rewarded, that we judge only on what a person brings to the table and nothing more.

Nothing could be further from the truth, of course, because we are ultimately human, and humans are biased in many ways both subtle and not. This post is not going to attempt to educate you on human bias. If you're unfamiliar with this concept, I'd welcome you to watch this talk put together by Google on the realities of bias in the workplace and efforts you can take to combat this.

Now, all that being said, I love the idea of meritocracy. After all, I am a CTO, surely I am here mostly due to my merit! OK, even ignoring my own position, I would really like to create an organization that does behave in a meritocratic fashion. I don't want to say that someone has to have X years of experience to do something, or Y arbitrary title. I want to reward people who show up, take on big tasks, and produce great results.

The most common way that people at startups attempt to create meritocratic environments, to avoid this title-driven fake hierarchy, is to eschew titles entirely. Eschew titles, have "flat" organizations. Removing the trappings of hierarchy will mean that we are all equals, and will create a place where the best idea wins, right?

Yeah, right.

Removing titles and pretending that the hierarchy doesn't exist does exactly the opposite of creating a meritocracy. It most often creates a self-reinforcing system where shadow hierarchies rule the day and those outside the in-group have even less opportunity to see their ideas come to life. It frustrates newcomers, and alienates diverse opinions. It is, in short, the enemy of meritocracy.

What is a poor meritocratic-seeking engineering leader to do?

The only answer I have found is echoed in the video I linked above. Far from eschewing titles and pretending no hierarchy exist, you must acknowledge this reality. And, furthermore, you need to be really, really explicit about what it means to actually be working at the level indicated by these titles. You need to first, make it really clear to yourself what is required at every level, and then make it really clear to your team what it means to be at every level. 

This is not easy to do. My greatest fear in implementing this has been the fear that people will come to me and try to "lawyerball" me into promoting them to a level that I don't feel they are working at. Or that people will become obsessed with their title and constantly be trying to get promoted and treating each other differently due to titles.

To point 1, though, if a person truly is meeting everything I have laid out as being necessary for working at a level, why would I not want to promote them to that level? It either means that I haven't really articulated the level clearly enough to really encompass the responsibilities, or in fact, they really deserve to be promoted and I am letting my bias get in the way of evaluating merit.

To point 2, if I lay out levels that I believe are genuinely increasing in impact and responsibility and have high bars to clear, why would I be upset if people strive and work hard to grow into them? "Meritocracy" doesn't mean "Only reward people who are naturally gifted at what I value." That's the thing I'm trying to stop doing!

On treating each other differently due to titles, well, that's a two part problem. The first part is this: creating a culture where ideas are welcome from anywhere requires cultivation with or without titles. The second is that generally people get promoted because they have shown bigger impact and influence on the organization, and so it's not that surprising that they will have bigger voices. I'm not sure that is a terrible thing, if those people are living up to the high standards that come with that influence.

Finally, of course, to get a group to embrace this is tough. So why not take the decision-making power to promote people out of the hands of managers? That is what we have done in my team. We now use promotion committees, composed of engineers at a level or two above the person trying to get promoted. Now the whole team is bought into the idea that promoting someone is not a gift bestowed by management but an acknowledgement by a group of peers that one should join their ranks. 

This is not going to be perfect, and it is a lot of work for me to implement. But in my experience taking the time to establish clarity in anything is a worthwhile exercise, and creates a better and ultimately more efficient organization. 

Revisiting ideas: Promotion from Within

Ages ago a friend of mine wrote a rather seminal post on "promotion from within". It is interesting to go back and read this post through the lens of hiring and leading a team for a few years. It is a great post, but I think that one major point often gets overlooked, and this point causes many companies who follow its advice to fail. That point is this:

2) Using either the few experienced managers you've been able to internally promote or failing that, outside executive coaches, intensely mentor your more inexperienced managers to develop their skills. Typically, because many of your management candidates were less than fully-qualified, they will demonstrate potential but still be unsure in their new roles. Until they are comfortable and practiced in their roles, both they, their peers, and their teams will exist in a state of some distress. 

This is problem I have seen both at my own company and also observed at others': We promote from within, but provide no mentoring or guidance to those so promoted. Great managers are truly not born. They are made, and usually made through both being sat down and patiently taught the ways to effectively lead projects and people, but also through observing both successes and failures.  They are also made by being called to task on their own personal failures, something that many startups are unwilling or unable to do. The cult of personality around founders and early employees can work against the one thing necessary to make "promote from within" successful: some form of external help.

Most of us in the startup world are working amongst people that have very little experience managing. And we've taken these ideas that Yishan so eloquently voiced, that culture is paramount, and elevated them to high status, while forgetting that there is a lot to learn to be a successful manager. I know that I came into this job two years ago thinking that given my natural willingness to be in charge and my strong technical skills I would be a great manager. Haha! Truthfully I'm only now getting to the point where I have an inkling of all the things I don't know, and a large part of that is thanks to a ton of coaching. I would not be able to lead my team successfully without coaching, and even with my own coach, I need a coach to help the managers that report to me.

So, promote from within. But don't cheap out on the process by forgetting that these new managers and leaders need help, need training, need to be held responsible for both the good and the bad that they will inevitably produce in their first months and years as managers. Otherwise you might as well hire experienced external managers, because my hunch is that the payoff is actually equivalent, risking culture vs risking unguided learning.

Getting From Here to There

As part of my work to make myself a better leader, I'm reading the book "What Got You Here Won't Get You There." The phrase itself resonates with me strongly now as I'm in reviews season and writing reviews for a number of senior engineers and engineering managers. One of the standard refrains I see in self-review "areas for improvement" is the desire to improve something very technology specific. A manager might say "I want to jump in more to the code so I can help take problems off my team." A senior engineer looking to grow to the staff engineer level might say something like "I want to get better at understanding distributed systems." Heck, even I am tempted to put "I want to spend more time in the early phases of architecture design so that I can help improve our overall technology stack." We're all falling victim to the problem of "what got us here won't get us there."

Engineers should spend their first several years on the job getting better at technology. I consider that a given and don't love to see that goal in reviews even for junior engineers, unless the technology named is very specific. Of course you're getting better at technology, programming, engineering, that's your job. You are a junior individual contributor, and your contribution is additive. You take tasks off of a team's list, get them done, create value by doing, and work on getting better at doing more and more. You got here because you put this coding time in.

After a certain point, it is more important to focus on what will make you a multiplier on the team. Very very few engineers write code of such volume and complexity that simply by writing code they enhance the entire organization. For most of us, even those in individual contributor roles, the value comes through our work across the team, teaching junior engineers, improving processes, working on the architecture and strategy so that we simply don't write as much code to begin with. There is a certain level of technical expertise that is necessary to get to this multiplier stage. As an individual contributor, a lot of that expertise is in knowing what you don't know. What do you need to research to make this project successful? You don't have to be a distributed systems expert but you should know when you're wading into CAP theorem territory.

It's harder for managers. Every time you switch jobs, you're interviewed with an eye towards the question, "can this person write code?" We don't trust managers that can't code, we worry that they're paper-pushers, out of touch. But when you hire an engineering manager, you often don't want them writing code. Managers that stubbornly hold onto the idea that they must write a lot of code are often either overworked, bottlenecks, or both. The further up you go in the management chain, the less time you will have to write code in your day job. The lesson here is not "managers should carve out lots of time to write code". It is, instead, don't get pushed into management until you've spent enough time coding that it is second nature. If you think that writing more code is the unlock for you to manage your team better, to grow as a better leader, you're going backwards. The way forward into true team leadership is not through writing more code and doing the team's scutwork programming. It is through taking a step back, observing what is working, what is not working, and helping your team fix it from a macro level. You're not going to code your team out of crunch mode by yourself, so spend your time preventing them from getting into crunch mode in the first place.

Coding is how you got here, engineering is what we do. But growing to levels of leadership requires more than just engineering. You've gotta go beyond what got you where you are, and get out of your comfort zone. Work on what makes you a multiplier, and you'll get there.

Moneyball

The first thing they always do is quiz you. When big tech companies look for employee prospects, the first test is always basic knowledge. The Googles of the world have a checklist. "Coverage Areas" is what they call the talents they're checking for in a candidate. The big three are Coding, Algorithms and Analysis, Systems Design. Maybe they will also care about Communication skills, and Cultural Fit. They put you through the paces. Can she code? Does she know her Big-O analysis, her data structures? Can she design a distributed system to mimic Twitter? Tick, tick, tick. Pass enough of the checkboxes, and they'll make an offer. Nice salary, great benefits, the chance to work on big problems with these intimidatingly smart folks. When it comes to the deep pockets and well-oiled recruiting machine of a big tech company, it can be hard for a startup to compete for talent. 

I was thinking about this a lot as I watched Moneyball last night. It got me thinking. I wish there was a sabermetrics for developers. After all, what is a startup but a cash-strapped team trying to win against the Yankees? This is an imperfect analogy, but let me break it down.

First a step back for those of you that haven't watched the movie and don't give a flip about baseball. Sabermetrics is basically a system that tries to predict, through past performance, how well a player will do in the future on certain metrics. In contrast to tests of basic skills (running, throwing, fielding, hitting, power) that talent scouts look for, sabermetrics focuses on the statistics of a player's actual game performance. Instead of going broke on a couple of big-name players, as many teams would, or gambling on hyped up fresh "potential", the Oakland As used this system to draft cheap players that together ended up forming a competitive team against the A-list roster of the New York Yankees.

The thing about baseball that makes it a useful analogy for many startups is that baseball is a team sport where the size of the team is fixed and the potential of the team in aggregate matters. The same is true for a tech team. We see so many stories about how you should only hire "A" players, that they attract other A players, and they out-perform other developers 10-1 (or 50-1 or 100-1 depending on how grandiose you're feeling). But how do you find these A players? The Derek Jeters are probably settled, and cost more than you can afford. Google and its kin have deep enough pockets to hire anyone that ticks off all the "Coverage Areas", know that they will get lucky and find some natural As in that bunch, train up some more, and the rest will be good enough to take on the mountains of other work needed at such a huge company.

The thing that Google intentionally neglects, and the thing you absolutely can't afford to ignore, is past performance in the game. What is the tech equivalent of on-base percentage? Product shipped. This is why everyone drools over open source developers as hiring potential. You can see their work, you can know that they've shipped. Teasing this out of others is a tough process. We don't have visibility into the work that most people have done. Writing code for you proves that they have the tools to deliver, and is an essential part of the interview process, but it's not enough to show that they actually have delivered. All we can do is ask them, as a detailed part of their interview, what they have done. 

I realize that relying on reports of past experience as part of the hiring process is fraught. I would never suggest you neglect technical vetting in favor of experience. It's easy to get burned by someone whose personality you like and who sounds smart, only to find out they don't have the basic skills to succeed. And even with the best interviewers in the world, it's always possible that you will still hire someone that chokes at the plate. In the case where you find yourself with a player that isn't shipping, you have to take to heart the other thing that you can do more easily than Google: get rid of underperformers. It sucks, and no one enjoys letting people go, but a startup cannot afford to keep people that aren't delivering.

Will this result in your team being full of A-list all stars? Maybe. Or you may find yourself with a team where few people are exceptional standouts, but everyone delivers. When everyone in your roster can reliably get on base, you're winning. You're shipping. And that's what the game is about.

Code Reviews, Code Stories

Code reviews are a tool that incites a lot of strong emotions from developers. Those who love them write tweets like 

Code review is hard - both reviewing and being reviewed make people cranky. But I know of no better way to make great software. -- @yminsky

This tweet, even in its adoration, still captures some of what people hate about code reviews. They make people cranky, to put it mildly. I personally don't like code reviews very much. In my experience, they are just as likely used to bully, score points, or waste time on pedantic style notes as they are to produce great software. In fact, I think code reviews are absolutely necessary only in three kinds of situations:

1) You don't have good automated testing practices in place to catch most errors at or before checkin.
2) You work on a big project with a very geographically distant team of developers (most open source).
3) You work in a company of many developers and huge code bases where strict style conformity is very important.

In my company, we have one team that falls into slot number 1, and they do code reviews for all checkins. The rest of the team does ad-hoc code reviews and occasional code walkthroughs, and we rely on the heavy use of testing to ensure quality. In general I feel that this enables a good mix of code correctness and checkin velocity.

The one thing this misses, though, is the required opportunity for developers to learn from each other. I like pair programming, and encourage my developers to do it when they are first starting projects or figuring out tricky bugs. But a lot of the time my developers are working in parallel on different code bases, and I felt that we were missing that learning moment that code reviews and pairing can provide. So I started asking people in interviews how they encouraged their team to work together and learn from each other, and I got a great suggestion: encourage the developers to show off work that they're proud of to other team members. Thus the Power Hour was born.

"Power Hour" is an hour that we do every Friday morning with my team and our sister team of warehouse developers. In that hour every developer pairs up with someone else and they take turns sharing something they did that week. Show off something you're proud of, ask for help with a problem you're stuck on, or get feedback on the way something was or is being designed. The power and choice of what to show lies in the hands of the person showing it, which takes away the punitive nature of code reviews; all they are required to do is to share some code. Show off, get help/feedback, and then switch. It's not about code review, that line-by-line analysis and search for errors big and small. It's about code stories, whether they are war stories, success stories, or stories still being written.

There are a lot of features of code review that this Power Hour doesn't satisfy. It's not a quiet opportunity to evaluate someone else's code without them looking over your shoulder. It's driven by the person that wrote the code and they are encouraged to highlight the good parts and maybe even completely bypass the ugly parts. It's not possible for the other person to fully judge the quality of what they're seeing, because judging isn't the point at all. Power Hour is a learning and sharing opportunity, and it is explicitly not an occasion for judging.

This has turned out to be a smashing success. It's amazing how much you can teach and learn in a concentrated hour of working with another person. Last week I showed off a new Redis-based caching implementation I wrote, and got to see all the code and a demo of a new Shiro authentication and entitlement system. I caught a few things I still needed to clean up in the process of explaining my work, and so did my partner. If you, like me, shun formal code reviews, I encourage you to try out a weekly turn at code stories. It's a great way to build up teamwork, encourage excellence, and produce great software, without the crankiness.

Process Debt and Team Scalability

Most of us in tech spend time thinking about technical debt. Whether it's a short-term loan or a massive mortgage, we've all seen the benefits and costs of managing and planning a code base with technical debt, and we are generally familiar with ways to identify, measure and eliminate this debt.

What about process debt? Process debt is a lot like technical debt, in that it can be a hack or a lack. The lack of process as debt is pretty easy to see. For example, never bothering to create an automated continuous build for your project. That's a fine piece of process to avoid when you have only one or two developers working on a code base, but as your team grows, your lack of process will start to take its toll in broken code and wasted developer time.

There are also plenty of ugly process hacks. Take for example the problem of a team of varying skill levels, and a code base that is increasingly polluted by poorly formatted, totally unreadable code. When faced with this problem you may be tempted to institute a rule where every line of code must be reviewed by a teammate. Later you discover that the two people with the worst style are reviewing each other, and things still aren't improving enough. So you declare that everyone must have their code reviewed by one of the senior developers that you have appointed. Now you have better style, but at the cost of everyone's productivity, especially your senior developers.

Adding code reviews was the easiest path to take. You just hacked in some process instead of paying up front to think about what the best process would be. But process, once added, is hard to remove. This is especially true for process intended to alleviate risk. Maybe you realize after a few months that the folks with questionable style have learned the ropes, and you remove the rule. But what if you added code reviews not to fix a style problem, but to act as a risk mitigant? I've done this myself in the case of a code base with very little automated testing and a string of bad releases. I'm now paying for my technical debt (a lack of automated testing) by taking out a loan on process.

An easy way to identify process debt is to ask yourself the following question: Will this solution still work when I have twice as many developers? What about ten times as many? A hundred? Process debt, like technical debt, makes scaling very difficult. If every decision requires several meetings and a sign-off, if every git pull is a roll of the dice for your continued productivity, or if you have to hire three project managers for every five developers just to keep track of the task list, you're drowning yourself in process debt.

Developers are wary of process because we too often experience process debt of the hack sort. I believe that both a lack of process and an excess of process can cause problems, but if we begin to look at process debt with the same awareness and calculations that we apply to technical debt, we can refactor our playbook the way we refactor our code and end up with something functional, simple, and maybe even elegant.

Debug Your Career: Ask for Advice

One of the most powerful relationship-building tools I have found in my career is the simple act of asking for advice. It's also something that I don't see a lot of people take advantage of, especially in tech. In some cases, it's an ego thing. What if they think I'm weak for not knowing, for not figuring this out on my own? Sometimes, it's a desire not to be a bother to the other person. Sometimes it just doesn't occur to you to seek outside help. But when you don't ever ask others for real advice (more than simply, "how does this code work anyway?", or, "what was that cool hack you cooked up the other day?") you leave a lot of potential on the table.

It shows you respect the other person's opinion (and thus, the other person)
We all want to believe that our opinion is important, and when you are actually asked for your opinion it is a token of respect for you as a person. You've heard that people like those that like them back? People tend to respect those that respect them back. After all, you have such good judgement in respecting them!
This really comes to play when you ask people that work for you or are junior to you for their advice, especially when you follow it or use it to open a dialogue on a bigger topic. As a technical leader this will usually come in the form of advice about technology, and let's be honest: none of us has the time to be a true expert in all of the technologies we use in our job. Why would you hoard the decision making on all technical matters? Your employees probably come to you with suggestions and opinions already, but taking care to specifically ask them for their advice is an important way to ensure they know that you respect them and the knowledge they posses.

It makes them a partner in your success
Think about a time when you've helped someone solve a particularly hard bug they were facing. A bug that was meaty and fun and made you think and also made you feel awesome and smart for being involved in solving it. Afterwards, did you feel some ownership stake in the success of that project? This is the feeling you give people when you ask them for their advice, especially when you take it and turn it into success.
Now think about a time when you've hit a bug in someone else's code and they have ignored your attempts to help them debug it, or worse, totally ignored your patches and pull requests. You probably feel a bit more animosity towards the project, and if it fails, perhaps it deserves to fail.
This set of feelings is analogous to proactively going to your manager and asking for advice on how to grown in an area, versus having to be told by your manager that you are failing. In the first scenario, you make your manager a partner in your success, and they feel pride and sense of ownership when you succeed. In the second case, you are at best an area for improvement and a worst a burden or even a write-off. 

It forces you to think about the problem you really have
You shouldn't ask someone for advice without knowing what you're looking for. Just as you're not likely to get much help debugging if all you know is that the program crashes, simply asking someone "Hey, any advice?" will probably get you little better than a cliche like... "ask for advice". Really valuable advice doesn't come from emailing Kevin Systrom and asking how you can get a billion dollars by putting your Hadoop cluster in a Cray-1. It's delivered when you tell your boss you're struggling with the challenge of managing a team and writing code at the same time, and how does he manage to keep an eye on everyone without micromanaging or spending every waking hour watching GitHub and Jira?


Of course, this comes with some stipulations. The act loses its power if you're just doing it for the sake of doing it. You have to be willing to at least consider taking the advice you are given, and you don't want to waste people's time. But if you take the time to truly think about areas where you'd like to improve, and go to people honestly asking for advice on how to do so, you may find that an extra set of eyeballs makes the bugs in your career shallow.

Yes, and...

I have a terrible habit. When confronted with a new idea, any idea, my knee-jerk instinct is to find its flaws. Or, to put it more succinctly, I'm a "no, wait!" kind of person. You want to add a new feature into my library? No, wait! That won't maintain API backwards-compatibility! No, wait! No one but you really needs that, why should we put it in a library used by everyone? No, wait! The work that will take us to review overwhelms it's worth as a new feature.

There is a well-trod school of thought that says to maintain creative collaboration, anytime you want to say "no, wait!", "no, but" or even just "but", you should instead start the conversation with "Yes, and". Want to add a new feature into my library? Yes, and we will have to think about how to add it without breaking API backwards-compatibility. Yes, and we should see what other community members think about the usefulness of the feature. Yes, and we'll have to evaluate the work that it will take to correctly implement and review.

"Yes, and" is a great baby step on the path to thought leadership and productive collaboration. But let's face it, it's easy to get a bit snarky with our yeses. Yes, and six months later, we'll have another release. Yes, and you can be on hand to fix the bugs that come in. Yes, and why don't we rewrite the whole thing in Scala while we're at it? (Watch Peggy struggle with this on Mad Men[16:50], when Megan shows her work)

So how do you really take "yes, and" to heart? My boss, who is a natural at this sort of thing, taught me one of his favorite tactics. It's not just saying yes. When a new idea is presented, find at least one positive thing to say about it, and praise that quality first.

 "That is an interesting idea. People using our service to do complex state maintenance could really use this feature, it would save them having to write a lot of code themselves."

The goal of this exercise is not only to keep the flow of positive collaboration going. It is also to force yourself to acknowledge the problem that the idea is trying to solve. You may not think the problem is worth solving, but this is something that your collaborator wants to explore, perhaps because it is causing them pain, perhaps because they have a different set of priorities than you, perhaps because they're simply trying to contribute to the discussion.

I will admit that despite knowing this is the right thing to do, I am absolutely terrible at following this advice in person. My knee-jerk nerd comes out and she is very into scoring points by pointing out flaws. Among the tech community, I'm hardly unique. Read the comments on almost any Hacker News thread if you don't believe me. And yet, the easiest place to start with this is online. You have time to think before you hit send on that email, submit on that comment, post on that tweet. Why not take the time to acknowledge the idea fully before pointing out its downsides? Just because you didn't think of it doesn't mean you lose by making it better.

Three Reasons You Should Be Training Your Successor

It's Friday afternoon of a long week. Despite wanting to pack up your bag and go home, you know you need to review the new hire's code. It's their first week so inevitably it will be some scary stuff for you to untangle. When you get in there, it is scary. But not in the way you expected. Instead of causing more bugs than they fixed, they've actually managed to fix every bug you gave them and in the process redesign a hairy part of the system into something rather... elegant. You want to find fault somewhere, but you can't. They're really good, so good that you're feeling threatened. I want to convince you that this threat is an opportunity. When you find that up-and-comer on your team, instead of trying to prove that you are better than them, train them to replace you. Why? Here are three major reasons:

1) Career Growth 
It's hard to grow yourself and your career within a company if you hoard the knowledge or ownership of a particular project. The people that succeed the best at growing into bigger roles are those that can point to a protégé waiting in the wings to fill the position they are leaving behind. This applies to us tech types that may not want to grow into managers, but want the freedom to move into new projects. It's easy to get stuck on the same codebase when you're the only expert in the area. Training other smart developers on the team lets you move on to new and exciting things as the opportunity arises, and with no guilt about leaving people in the lurch.
Even if you prefer to switch companies every few years, it is always great to be able show a track record of several successful projects per company, and it gives you the opportunity to get a good breadth of experience.

2) Guru Points
Teaching and mentoring others makes us learn what we know even better. I always find that any time I have to give a teaching talk on a topic, I learn that topic a little bit more. Explaining things to others formalizes what you know, and in watching them learn they will almost always teach you something as well. Do you want to grow into the guru of your team or company? Mentor others and teach them all you know, and before long you may find yourself the most trusted advisor of the team.

3) A Stronger Network
Helping others grows your network, and provides you a pool of talent that you can draw on throughout your career. In a big company, knowing people on other teams that trust and respect you makes cross-company collaboration much more effective. If you are the sort to move between small companies every few years, it's likely you will need to hire talent to work with you and make those companies successful, and who better than your former mentees? And if one of those that you mentor grows to become a great success? They are not likely to forget the people that helped to get them where they are, and can be a very valuable part of your professional network.

This post is dedicated to my mentor Mike, who taught me this rule and practically every other useful thing I know. Please leave a comment here or on twitter!