Thursday, January 28, 2016

Qualitative or Quantitative but always Analytical

I did a panel at Etsy's engineering leadership offsite today, which was amusing. One of the topics of the panel was:
Challenges of balancing data-light product bets vs purely data driven incremental improvements.

All three of the panelists agreed, although each of us phrased it a different way. The first panelist (Dan McKinley) spoke about the need, even for products that are not purely A/B test driven, to drill down on the goals and try to find something to measure about how a project will actually achieve a goal. If the project is part of a larger goal to increase revenue by 25% this year, what way is it contributing to that? How do we measure its success? Even when you are driving decisions by "vision" there is some quantitative goal you are trying to achieve, so state what it is.

The second panelist (Albert Wenger) spoke of the importance of balancing the quantitative with the qualitative. Some things cannot be purely quantitatively measured, and there are qualitative measures that are incredibly valuable to the process of discovering product market fit. User testing, user research, watching how people actually engage with a product are all essential to creating something great, beyond simply finding numbers to measure and trying to increase them.

My perspective on the issue is that qualitative methods are important, but qualitative is still analytical. You may not be able to use data-driven reasoning because you're starting something new, and there are no numbers. It is hard to do quantitative analysis without data, and new things only have secondary data about potential and markets, they do not have primary data about the actual user engagement with the unbuilt product that you can measure. Furthermore, even when the thing is released, you probably have nothing but "small" data for a while. If you only have a thousand people engaging with something, it is hard to do interesting and statistically significant A/B tests unless you change things drastically and cause massive behavioral changes.

So, instinct and guesses are necessary. But we needn't lose our analytical approach just because we don't have data. When you build something, you have a hypothesis about the person you are building it for. You have a guess as to what they will like, and most of the time you have a reason for that guess. When you're trying to build a business, you need a chain of events that you expect could happen that would indicate a product is successful. You have a sense of what to start measuring once the thing is released that will show whether it is working. Answering the questions of who is my customer, why would she use this, and what will signs of interest and engagement look like is essential to going from vague instinct to thoughtful first product.

Data can't make all our decisions for us because data isn't there to get us from 0->1. We have to use our powers of observation, of empathy with our customers, and of deduction, to create smart hypothesis in a qualitative way. Qualitative analysis will always have a role in product development, and customer empathy is likely to drive us more quickly to great products than simply relying on numbers alone.

Thanks to Etsy for hosting and my apologies to my fellow panelists if I misrepresented your views!

Monday, January 25, 2016

Hiring Engineering Managers: Screening for Potential

I have been in many discussions on the best way to interview and hire engineering managers. Here are my thoughts, having done this both successfully and less successfully, including some things that I have looked for in the past when being interviewed. 

First: Be thoughtful about what you are looking for. There are people out there who are looking for the opportunity to go into management. Lots of them, in my experience. These are good people to hire, because many of them will turn out to be good, thoughtful managers. Most of the time I hired this sort of person into a senior engineering role that quickly became a tech lead role. I was explicit at hiring that we didn't have a team to give them immediately but that I would be expecting that as the overall team grew they would move into such a role when it became available.

Now, I should be clear, this exchange requires a lot of trust on both parties, as well as the possibly unspoken assumption that they still have to prove themselves capable of doing the job once on the team. I have turned down jobs that asked me to make this bet, and I would not hold it against anyone who felt that it was too risky. But on the flip side, if you really want to grow your management from within, hiring people who both want to be eventually moving to leadership roles but are comfortable coming in as individual contributors first is pretty essential to making that work. If you want to grow management from within but don't bother to look for people who want to grow into management roles when you're hiring, you may end up with mostly people who just want to code, and that is not good for anyone.

OK, so you're hiring a specific management position. What do you look for?

There are two camps here. The first camp is that you look for incredibly smart tech lead-level developers who may have had limited management experience and put them in the role. They will easily pass whatever technical screens you put in front of them, but hiring is a risk because they may not really be good managers. If this is the way you want to go about hiring managers, you need to spend a good deal of time focused on screening for management potential. Screening for potential is different than screening for experience. Right now, I'm going to talk about screening for potential; in part 2, I'll talk about experience.

Questions to tease out potential: 

Tell me about a project where you have acted as the tech lead. What was your role like, as tech lead? What were things you did that were different from the rest of the team? How did you ensure that the project was successful?

What you are looking for: Someone who answers with more than just "I designed the architecture, chose the libraries, and wrote the most technically challenging pieces of the code." They should have taken an active role in the project management, even if there was another person explicitly or implicitly in that role. They should have contributed to predicting problems with the delivery and working with the people on the team or cross-team to ensure success.

When you bring a new team member onto your team, what kinds of things do you personally do as part of their onboarding? Have you ever been a mentor to a new hire or intern? What was that like, what did you learn from it?

What you are looking for: Someone who is actively engaged in the work of bringing on new people, and thoughtful about making that process better. Someone who respected the work of mentoring, who isn't just trying to shed human interactions quickly to get back to code.

Tell me about some things you have done to make the process of writing or delivering code in your organization better.

What you are looking for: Some strong examples of seeing process/people/systems problems and raising their hand to suggest improvements.

One suggestion I have heard, but not tried, is to do a role-playing exercise with the candidate. Set up a circumstance that might happen, such as, an employee is unhappy that they did not get promoted. Provide an overview to the candidate and give the interviewer some details that may include information that the manager doesn't necessarily know. Have a third party observe the interaction, and then at the end of the role play all three talk about what went well and didn't. This could be an interesting tool for hiring either the experienced manager or the potential-driven manager, but I also suspect it is easy on the flip side for it to go poorly if the interviewer isn't good at guiding the roleplay and knowing what to look for. (Credit to Marc Hedlund for this idea!)

Finally, when hiring this type of candidate, you are probably going to get (and maybe even should be intentionally seeking out) someone who is going to not only manage people but drive technical decision-making. Make sure that the people who currently drive technical direction (if they exist) are aligned on that front with the candidate. If the candidate is gung-ho about functional programming and microservices and you are happy in a more conservative technical space, you may end up with someone who wants to make big technical changes that you might not agree with. The team should feel a general alignment to their technical perspective, and ideally people are excited about working for this person because they feel that they will learn something, but don't just hire them as a manager because people are excited about their technical chops.

Overall, when screening for potential, look for signs of stepping up, caring about the people on the team, and thoughtfulness about the processes. In general you should also be looking for excellent communication skills, and everyone who interviews the person should feel pretty comfortable with the idea of working for them. Be wise to potential bias here. The best managers are often overlooked because they don't pattern match to certain characteristics, whether they are "tall and male" or "forceful personality" or whatever. Talk to the team before the interview and give them examples of great managers who sit outside of those stereotypes to reset their stereotype bias a little bit.

When you mishire on potential, it tends to come from overvaluing technical skills + pattern matching on "what a leader looks like", and the failure mode is managers who just don't deliver coherent teams and/or can't deliver projects effectively. Never ever hire a person you feel is overly ego-driven.

One final word on this candidate: If you hire someone for potential, be prepared to train them. They are going to need help. Whether it is formal training or a lot of mentorship from you or a mix of both, no one is born knowing how to manage. I think it is worth sometimes taking a risk on people like this (I'm glad someone did that for me once!) but they will struggle if they have to do it all alone.

Thursday, December 31, 2015

What is a Technology Company, Really?

I have been thinking a lot about what I want in my next job, and part of that thinking has been asking the question of what, exactly, it means to have “technology” as a core cultural value of a company.

Let’s quickly put away the idea that a “technology” company is one that produces bits, and that any company that produces bits is a technology company. By some definitions of technology that is true, but equally by some definitions of technology pretty much every modern company is a technology company, and so it dilutes into meaninglessness. Certainly, I do not think the product being produced is the interesting element for me personally. It’s likely I will always be involved in producing software of some sort, but that doesn’t say much of anything about the values of the company I produce it in. So, the production of software is certainly insufficient for a company to hold “technology” as a core cultural value, and furthermore it is silly to think that a company must ONLY produce bits to hold “technology” as a core cultural value.

As part of this thinking I started to ask myself the question, What the hell does technology mean, anyway?, and I came across the fascinating Ursula Franklin. She wrote a book called The Real World of Technology, in which she differentiates technology practices into two types: holistic and prescriptive. The holistic practice has control of the production in the hands of one person or group involved from start to finish, from determining the product, sourcing of materials, to crafting of parts, to finishing. The prescriptive process, on the other hand, is more of the assembly-line model. The steps to create the final product are broken into discrete, standardized steps that can be accomplished by different people in stages.

What does this have to do with “technology” as a company value? Well, perhaps the company value we are interested in is not in fact technology, but it is the valuing of holistic technology. As industries and practices mature, they tend to become prescriptive, whether or not it produces the “best” outcomes. Prescriptive application of technology (“technology” here being the techniques for achieving some outcome) allows for control over the process, predictability of the outcomes, and surveillance. Decisions can be made by the manager, passed down to the workers, and enforced.

However, the process of writing code is rarely completely prescriptive. Because of the difficulty in predicting what will need to change and the compounding impacts of choices made in the past, as well as the necessity for constant support and evolution that most business expect from their software these days, strong engineering teams tend to run somewhat more holistically. You may be given a discrete task (or “ticket”), but there can be a great deal of freedom in how it is implemented, depending on the size and scope, and there will almost always be need for work that cannot be easily scoped into a simple discrete task. Software has so far rebuffed efforts to fully turn it into a prescriptive style of work over long periods of time. If you are a working engineer you may think I’m joking, but while senior engineering leaders may be expected to talk a big game about “velocity” of the teams and all the measures they use to determine engineering efficiency, in reality, vanishingly few feel comfortable in the tools out there available to monitor such a vague concept, and most of us instead go by gut instinct and secondary measures like release volume and defect frequency.

So, let’s go a step further and talk about startups. In a young startup, most work is holistic. Whether you are in engineering, marketing, even some parts of finance, there are so few people that you are often given full control over your process. You are allowed to do things differently, no one is watching, there is no prescriber to tell you that you must send that marketing email on Wednesday instead of Tuesday. So early startups behave in a holistic-driven way, whether or not they hold that as a core value, because they must. However, as the startup grows, it will start to experience some need for prescriptive processes, and here then becomes the question: Can a startup that does not value fundamentally holistic technology be a “tech” startup, in the modern sense?


Most startups claim to be “tech companies”, but what do they value?


If you value “technology”, you might be saying that you value the ability to see a problem and make the changes necessary to address that problem, at a speed that would not be possible if you were having to change the behavior of humans instead of the behavior of bits. For this to happen, though, the person or group who sees the problem needs to be able to go in and do the fix. They need to be able to access the information that lets them see the problem holistically to identify that solution. This becomes relatively difficult in a prescriptive implementation, because each individual may only understand their part of the task, and only perhaps the manager or overseer understands the whole. In complex software, it is likely that no individual understands the whole, but that the group must get together and act holistically to address and solve problems. Furthermore, because of the difficulty for any one individual to see all problems, members of the group must be empowered to raise problems to the overall group, communication as peers across hierarchy and function needs to be supported and encouraged. Thus the tech company common value of “transparency.”

Or, perhaps you are saying that you value the ability for a small number of people to do work that impacts a huge number of people due to the relatively low physical footprint of software and the ease of scaling it relative to physical goods and services. The flip side is that a few people can also negatively impact huge numbers of people by making a mistake, releasing a bad feature, taking down a system. In the case of unknown and ever-changing complexity (due to ever-changing and evolving systems), you can only mitigate this by placing a high value on learning from those mistakes, and evolving your tools and practices. Because almost any member of the team has the potential to cause these problems, all members must be part of the learning process. Thus the tech company common value of “learning.”

You may just be saying that you value a type of thinking that is a combination of creative about seeing possibilities, scientific enough to quantify those possibilities, and forward-thinking enough to actually enable the ideas to thrive beyond conception. A type of thinking, furthermore, that is comfortable with change, and pushes for change as needed. This sort of thinking doesn’t generally happen in a windowless room, where people have no creative freedom and must execute the tasks handed down to them in the way they were handed down. Some companies value this but only in certain classes of people, “research” or “creative”, for example. I think that a company that places value on holistic technology will encourage this in all types of employees, and this value may be expressed as the tech company values of “data-driven”, having a “focus on impact”, and “embracing and driving change.”


And then there’s the “tech company” that isn’t


Some companies claim to be tech companies because they view technology as the company’s competitive advantage. This is the easiest, but slipperiest definition. To value it as a competitive advantage, intellectual property that forms a moat around your business, without valuing the common shared cultural values of engineers themselves, is insincere and hollow. This is the value of someone who would happily turn their engineering team into robots who produce exactly what they are asked to produce, when asked. The “value” is entirely in the difficulty of accessing the skills to turn these ideas into reality, and therefore it is only as high as the cost of acquiring those skills. This, to me, is not therefore a “technology” company. It is a company that needs technology, but does not fundamentally value it.


What does this all mean?


These are just some idle thoughts I’ve had while considering my next move. I know that I want to work somewhere that values itself not as a tech company for the intellectual property, but as a tech company for the values that I believe great engineering teams embrace. As you look around at your companies and your own values, I hope this will help you consider what it might mean for your career and future as well.

Cross-posted from Medium

Wednesday, December 2, 2015

Reorgs Happen

Yesterday I gave a talk at the NYC CTO Summit on Reorgs (slides). Here's a rough summary of the content, prior to the video release.

The general theme of this summit was "Driving Change." When I came across that theme, I immediately decided to talk about the process of reorganizations. In particular, the process of being a leader of a team involved in a large top-down reorganization. I have been in the leadership team through three of those over the past four years or so, and I have had many conversations with friends at other companies over the years who were in the middle of them, either leading them or as a person swept up in them.

My first point about reorgs is that fundamentally, in companies big and small, they happen. They are disruptive and stressful, but I personally think they are often a necessary evil, the "full GC" of organizational structure change. You can get a lot of value having smaller parts of the organization morph and change as needed, but sometimes a higher-level view of the business drives the need for larger and more top-down change.

I happened to see a tweet that led me indirectly to this blog post, and in particular, the following structure:
This is a great structure for talking about a reorganization, and in particular, your role as a leader in a reorganization.

Vision: The Vision is the "why" of what is happening. You may not be the initiator of the "why", it might be your CEO or someone else in the leadership team, but you must understand it and focus it. Usually the reasons leading to a reorg are one or more of:

  • Inefficient communication and collaboration between teams
  • Adding or removing major products or focus areas
  • Change in the size or makeup of the team

These are all well and good as a root cause, but you need to provide a lot more nuance to make this something that people buy into and want to follow. Especially when a reorg is in response to strategic change of focus. You're the leader of tech, so first make sure you understand and are on-board with the why, and then think about the way to communicate it to the rest of the engineering team in a way that makes sense. Without a clear vision, people will be confused as to why this is happening, even if what they are supposed to do when and how makes sense.

Skills: Do you have the skills to actually make the change happen? You may think that a reorg shouldn't require a lot of skills you don't already possess as a manager, but I disagree. There are many details to be ironed out in a reorg, many steps to follow, especially in a large team.

The first reorg I helped with moved our tech team from functional teams (frontend/storefront, backend) to what we called "pods", cross-functional teams with tech and product and high-level business goals. It was driven by both inefficient communication and a growing team. This was probably the easiest reorg that I led because the team was pretty small, and the lesson here is important: things that are practically free for a 20-25 person team are much more complicated when you're dealing with 60 people, let alone hundreds. The reasons were clear, we didn't need a ton of planning or incentives for people to do it, we just needed to clearly communicate what was happening why and move it through.

The most important skill for you as the leader of a large team through a reorg is communication. (In general, this is the most important skill that leaders need for pretty much everything). When reorgs go bad, one of the ways they go bad is that the reason for the change is not communicated well to the whole team, and the timing of communication is not coordinated, so some people know what's happening, others don't, and thus starts the rumor mill and the anxiety skyrockets. You are the leader. Write down exactly what the purpose is, the nuance behind it. If you need to write versions for your managers and versions for the whole team, do so. Think about your communication, and plan it as best you can.

Incentives: Why should people play along? What are they going to get out of it? You need to advocate for your team, and make sure they are going to be eager to embrace this. This is not selfish but rather sensible. If your team doesn't buy in, the reorg won't go as well, and the company will suffer for it.

Resources: Do you have available now what you need to make this happen? In the case of a reorg, that usually means time and focus. If your whole team is pushing out a major release of your mobile app, or focused on some other new launch, are you really going to distract them right now with the turmoil of a structure change? I hope not. Yes, a reorg may very well mean things need to slow down for a period of time while you figure it out and get the new teams formed, and gelled.

Of course, the other element of resources is in the new organizational structure you create. This brings us to the story of my second reorg. We had good success with the "pod" structure, but we saw that the focus for the pods was too high-level and we wanted to really get a focus on certain business strategies. We also wanted to expand the teams beyond tech/product to include other areas of the business who would be involved in the business strategies such as marketing, customer service, finance, operations. So we created what we called "strategic pillars". These were somewhat like business units, with a general manager who was responsible for the strategy of the cross-functional team (although not the people management), and members from technology, product, and the business.

Both incentives and resources were a big part of this reorg. On the initial list of candidates for general manager we did not have anyone from engineering, and I pushed to make sure that we did end up with a general manager chosen from the tech team. This was to ensure that engineering continued to be seen as an important strategic partner in the overall company, instead of an execution arm for product and business leaders. We also created a specific tech lead role for each pillar, who served as part of the pillar leadership.

As for the issue of resources, one of the mistakes I believe of the initial pillar list was creating one more pillar than we had adequate staff to support. Instead of spreading the team too thin, we simply did not staff that pillar with tech, saying that it would start out with more business analysis and research and as we came up with concrete plans we would hire into it. We ended up never getting the staffing the pillar needed to be successful, and eliminating it, which in turn was a big disappointment for the people who had been on that pillar. If you put people into leadership opportunities and then take them away, even if it is a good business decision and not an indictment of the person, they will still see it as a loss and you are very likely to lose them over it.

It's a cliché that every "Yes" you say implies a "no" to something else, but saying "no" to stretching your team too thin in a reorg is an essential part of making it successful.

Finally, the action plan. Without a clear action plan, you end up trying to start, realizing you're not ready, stopping, and starting again, sometimes many times over. You may not be the right person to make the entire action plan yourself, I know that is not my personal skill set. But you will still be involved in the planning process. If your reorg is intended to help focus people on new business strategies and goals, take your analytical mind and scrutinize those goals. Do they make sense? Are teams going to be able to work on their goals without negatively impacting other teams? If you have multiple teams with conflicting goals, you will quite possibly end up with turf wars.

This was one of the major elements of the final reorg I worked through. We had a nuanced set of goals that we wanted the teams to accomplish, and it took us several rounds of revisions to get to teams with goals that were productively aligned, independent enough to allow separate measurement without being in conflict. This process was necessary, but we suffered the downside of lacking a clear action plan, false starts, while we ironed it out. The team knew changes were coming, and they tried to tie up loose ends and finish up their work to be ready to move with the new organization. But we took longer to get the new organization together than anyone expected. With better planning earlier, we may have been able to avoid this period of uncertainty.

All of the reorgs I went through helped to move the company towards a more healthy, productive and focused structure, and I believe they were generally good for us. My final two pieces of advice for anyone managing a large team in a reorg are to remember that you don't have to do it alone, and that in the end you have to let go. Work closely with your peers to plan this, and expect that you will do some negotiating and have some outcomes that you like and some that you hate. Then, when it's out, let go. The teams will take a while to fully gel, the goals will probably shake out even more as they go through the actual process of planning on the teams. Some people will be happy with their new place, others will be unhappy and may even quit.

So, vision + skills + incentives + resources + action plan = success, right? Hopefully! However:

Reorgs are unlikely to solve all of your problems overnight. They are not a magic bullet exercise that fixes cultural issues or a lack of business strategy. If you aren't careful, your reorg will feel like rearranging deck chairs on the Titanic, a pointless waste of time for everyone involved. So don't be afraid to do them as necessary, but be realistic. This is a major disruption that impacts everyone, don't just do it for fun.

Friday, November 27, 2015

The Manager as Debugger

I have observed that the best engineering managers I know are often also great debuggers. Why would this be? What is it about these two tasks that has such an overlapping skill set?

A great debugger is relentless in their pursuit of the “why” for a bug. This is simple when we are looking for errors in application logic, but we all know that bugs can go many layers deep, particularly in complex systems that involve many separate parts operating over time-delayed networks. A sign of a poor debugger is a person who, when they add a log statement to a piece of concurrent code to attempt to find an error and see that the error can’t be reproduced, assumes that they have therefore fixed the problem. It’s a lazy habit but a common one. Sometimes there are problems that seem impossible to determine, and many people don’t have the patience to dig through layers of code, theirs and others’, log files, system settings, and whatever else is needed to get to the bottom of something that only happened once. I can’t blame them. Obsessive debugging of one-off issues is not always a great use of your time, but it does show a mind that cannot be satisfied with the unknown, especially when that unknown might cause them to be paged at two o’clock in the morning.

What does this have to do with management? Managing teams is a series of complex, black boxes interacting with other complex, black boxes. These black boxes have inputs and outputs that can be observed, but when the outputs aren’t as expected, figuring out why requires trying to open up the black box and see what is going on inside. And, just as sometimes you don’t have the source code, or the source code is in a language you don’t understand, or the log files aren’t readable, the black boxes of teams can resist yielding their inner workings. 

Teams also share the characteristic of another famous box, the one containing Schrödinger’s Cat. The point of that experiment is to show that the act of observing changes the outcome, or rather, causes an outcome to happen. You can’t go into a team and not change the behavior of that team by being around them, sitting in their meetings, watching their standups. Your presence changes the team behavior and may hide the problem you are trying to find, in the same way that a log statement can cause a concurrency issue to be magically erased, at least for some time.

To debug a system properly you have to be able to have a reasonable hypothesis that explains how the system got into the failed state, preferably one that you can reproduce, so that you can fix the bug (or at least prevent it from happening in the future). To debug a team, you also want to attempt to get a hypothesis for why the team was having problems. You want to do this in as minimally-invasive way as possible, to prevent your meddling from obscuring the problems. You have the added challenge of team problems not generally being single failures but more like performance issues, the system is running but it seems to slow down from time to time, the machines are ok except occasionally they crash, people seem happy but attrition is too high. 

Let’s work through an example. We have a team that feels slow. You have heard complaints from their business partners and product manager that they are slow, and you agree that the team just seems to lack the same energy as your other teams. How do we figure this out?

Debugging this deserves the same rigor you would apply to debugging a serious systems issue. When I debug a systems issue, the first thing I look at is generally log files and any other record of system state from the time of the incident. When talking about a team that is not producing work fast enough, look at the records. Look at the team chats and emails, look at the tickets, look at the repository code reviews and checkins. What do you see? Are there production incidents happening that are taking too much time? Are a bunch of people sick? Are they bickering over coding style constantly in their code review comments? Are the tickets that are being written vague, too big, too small? Does the team seem upbeat in their communication style, sharing fun things as well as important work in chat, or are they purely business? Look at their calendars. Is the team spending many hours a week in meetings? Is their manager doing 1-1s? None of these things is necessarily a smoking gun, but they may point to an area to address.

Perhaps everything seems ok in all of these indicators, but the team still just is not performing as well as you believe they should. You know the talent is there, the team is happy, they’re not overburdened by production support. What is happening? Now is the time to start doing some potentially destructive investigations. Sit in their meetings. Are they boring to you? Is the team bored? Who is speaking most of the time? Are there regular meetings with the whole team where the vast majority of the time is spent listening to the manager or product lead talk? Boring meetings are a sign. They may be a sign of inefficient planning on the part of the organizers. There may be too many meetings happening for the information covered. They may be a sign that the team members don’t feel that they can actually help set the direction of the team, choose the work that will happen. Boring meetings are a sure sign of time wasted, if not bigger leadership problems.

Ask the team what their goals are, can they tell you? Do they understand why those are the goals? If they don’t understand the goals of their work, their leaders (manager, tech lead, product manager) are not doing a good job engaging the team in the purpose of the work. In almost every model of motivation, people need to feel an understanding and connection with the purpose of their work. Who are they building these systems for, what is the potential impact on the customer, the business, the team? Did they have any part in deciding these goals, and the projects that they’re doing to achieve them? If not, why not? When you see a team spending all of their time on engineering-sponsored projects and neglecting product/business projects, it’s likely that the team does not appreciate or understand the value of the product/business projects that they are supposed to be working on, and therefore they are lacking in motivation to tackle them.

Finally, you might take a look at the actual team dynamics. Do people like each other? Are they friendly? Do they collaborate on projects or is every person working on something independently? Is there banter in the chat room, in emails? Do they have a good working relationship with other adjacent departments, and with their product managers? These are little things but even very professional groups tend to have a degree of personal connection between the members. A bunch of people who never talk to each other and are always working on independent projects are not really working as a team. There would be nothing wrong with that, if the team were performing well, but given that they are not, this may be contributing to your problem.

Sometimes managers of managers choose to take such problems as something that the manager of the team just needs to fix. You measure the manager on the output of their team, after all, and it is their responsibility to fix it if things are not going well. This is true, but just as I sometimes jump in and help debug complex system outages even though I rarely write code, it is ok to jump in and help debug team issues as you see them, particularly when the manager in question is struggling. It can be an opportunity to teach the manager and help them grow. It can also reveal more foundational problems with the organization, such as a lack of senior business leadership that even the best managers can’t identify or resolve alone. 


The pursuit of why when it comes to organizational problems is the thing that gives you patterns to match on, and lessons to lead with. We get better at debugging by doing it often, and learn which areas tend to break first and which indicators provide the most value for understanding issues. We become better leaders by pushing ourselves and our management teams to really get to the bottom of organizational issues, searching for why so that we can more quickly resolve such issues in the future. Without the drive to understand why, we rely on charm and luck to see us through our management career, we hire and fire based on charm and luck, and we have a huge blindspot when it comes to truly learning from our mistakes.

Friday, November 6, 2015

Truth and Consequences of the Technical Track

About a year ago, Dan McKinley aka McFunley wrote a bit on the technical track. The piece has stuck in the back of my mind for quite a while, and continues to influence certain points I make when discussing career progressions of engineers. Let's get them out.

I think that Dan's take is cynical, but not entirely incorrect. We need managers. As companies grow, at some point, you need people whose job it is to organize other people. I think the idealistic goal of management is to help teams live up to their talent potential. The realistic experience of management is often an abstraction layer between upstream and downstream, to help flow information, each layer helping to make a finer-grained set of decisions and adjustments to keep the overall company moving in the right direction.

Let's talk first about why I personally went into management. I was successfully performing in one of those technical track positions, at a company where I felt pretty confident I would be able to continue to be promoted in the technical track positions up to the highest level if I put the work in and continued to perform well. I was working on interesting things, paid very well, and on paper, everything was perfect. And yet, I quit to move to a smaller company and go into a management position. Why?

I realized pretty clearly that the scope of my ambitions was greater than the scope of my ability to produce things independently. I could not write enough code alone to achieve the kind of impact that I wanted to achieve on the company I was working for. Even with a small team, I felt that my ability to make a difference would be limited. I would have to make extremely good choices as to what to guide the team to do, and my effectiveness would always be limited by what I now realize is actually "product market fit." If I made a great product that no one else in engineering wanted to use (I was working in infrastructure engineering at the time), I would not have much of an impact.

So, instead, I gave up some degree of hands-on technical time in order to have a broader ability to focus people on projects where I felt their impact would make the most difference on the company. Ultimately, that is a core part of any technical leadership job, not doing all of the work yourself, but helping to both see what needs to be done and focus people on getting it done in the right way.

Now, you can imagine a situation where you have an engineering manager who deals with all the "people" side of things, paired with a technical specialist who makes all the decisions about what needs to be done and how it should be done, as per their technical expertise. Why doesn't this situation exist? Well, imagine putting yourself into the shoes of the engineering manager. You are basically a glorified project manager with little decision-making power. Except... all of the people report to you. You have hiring and firing power. You write their reviews. Do you really have no decision-making power? If you disagree with the technical specialist about what needs to be done, why would the technical specialist have final say? It is unrealistic to believe that the person with management authority over the people would have no influence over what they do, even with best intentions assumed.

The technical specialist, with no management authority, is limited. They are limited in what they can produce by the scope of resources (people, time, support from other departments, computers, etc) they have available to them. A people manager may give them a team to focus on their ideas, but that will always be balanced by their ability to produce valuable output as defined by whatever that people manager is being measured on. Miss an alignment with whatever the manager (or THEIR manager more likely) sees as valuable, and you risk losing those resources or having them siphoned off for "more important/pressing" work.

If a company has mostly reluctant/unhappy managers who would truly rather be coding, they have created a culture where code is more valued than management. Think about that. I created a team where the managers, by and large, were happy to be managing, and in the few times when they were not happy to be doing it, they went back to technical focus and we adjusted the teams. I was accused at least once of undervaluing technical contribution, so you should feel free to take this with a grain of salt, but reluctant management is a sign of a broken system, not a necessary an expected outcome of a growing engineering organization.

Dan mentions in his piece that one solution is that we could be promoting people more aggressively on the technical track. I agree with this, if the problem we are solving is giving productive individual contributors more money/bigger titles. Here is the alternate cynical perspective: the technical track exists so that we won't lose people who do good work and have valuable institutional knowledge, but the impact that those people have is often not equivalent to the impact that managers have (for good and for evil). Most companies don't actually need nearly as many people at senior levels of the technical track. We don't want to lose all of them, but there are diminishing returns for people who are possibly just incrementally better at building software. That's why you start to see language about scope of impact in staff engineering job ladders. As leaders, we want to encourage people to actually show results at broader scopes before we promote them. This just takes longer if you have to do it alone or with a small team. At a functional company, people aren't usually promoted as managers until they have shown they can do the next job by managing larger teams and actually doing the work to show the results. Why should the technical track be any different?

What about superpowers that could be given to technical specialists to make up for the authority given to managers? I would personally observe that often, senior technical staff work less hard than senior managers. The superpower of a senior technical staffer is that they get to work on harder intellectual problems and/or more speculative work, they get the luxury of a calendar that is far freer of obligatory meetings and tasks, and they are pressured far less than management for results on tight timelines. In short, by taking the technical path, they have traded off getting to continue to focus on what many engineers consider to be the fun stuff in exchange for a lot less clarity on how to progress and make an outsized meaningful difference. They don't have to work as hard as managers, they often don't work as hard, but on the flip side when they want to work harder to accomplish more it's less clear where to put that effort to gain value.

We all make tradeoffs. Engineering managers are making the tradeoff of getting farther away from the immediate reward (and, I will note, general tech cultural cachet) of day-to-day coding, as well as giving up control of their time, for a clearer career path and possibly more authority. Those who choose to stay technical should expect a likely slower career progression, and they will have to put in the difficult work to learn how to influence without management authority, but they should have more freedom from other people's demands and more control over when they put in the hard work to grow. Make no mistake, growth is hard no matter which way you go. You may have a clearer workout plan as a manager, but you still have to hit the gym and get sore. If you're not a little uncomfortable, what makes you think you're really growing into a new role?

Thursday, October 22, 2015

Open Source Culture

One of the biggest achievements of my career to date, one of the biggest impacts that I have made so far, happened almost as an after-thought. On March 26th of 2015, I released publicly the engineering ladder that the team created for Rent the Runway. I want to reflect on that for a moment because I keep hearing more and more people refer to this ladder.

Why has the Rent the Runway ladder been so viral? I've been told that companies from Kickstarter to Slack to Lyft and beyond have used it to inspire discussion and serve as a starting point. Why now?

We are in a point of rapid evolution in startup culture. A few years ago, everyone was obsessed with flat organizations, zero-process anarchy. And then we all started to live through the consequences of that, and many of us realized that it wasn't the utopia we were promised. Suddenly we saw that having no title didn't actually mean that every voice in the organization was heard equally, it often just meant that the loudest voices were the only voices heard at all. People began to push back on this.

We have become aware of unconscious biases and the challenges presented there. There's a huge temptation to have a very lightweight, low-detail engineering ladder. Unfortunately, that gives people only a vague idea of how to move forward. As we become more aware of the impact of bias on human decision-making, we attempt to provide more clarity to combat this bias. I realize that no amount of ink spilled can ensure a perfectly quantifiable process that takes all human bias out of it, but I also think there's little harm in trying for more clarity. And it turns out that many people appreciate it, and not just the people most affected by unconscious bias.

The devil is in the details. But putting in those details is hard, so providing a thoughtful starting point is better than providing a basic outline. Just as you only use the features of open source software that you actually need, you only need to take the details from open source culture that you want. Companies can (and often have) taken out details from this ladder that they don't like, but it's much harder to take a basic outline and flesh out all of the details yourself.

People want to know what they are getting themselves into. A recruiter commented to me once that the public engineering ladder was a massively useful tool for recruiting. Candidates knew what the structure of the org looked like, what the potential paths forward from a career growth perspective were available to them, and what we were looking for at a given level. It gave them more clarity into the workings of the organization in a way that most companies at the time were not providing.

This has gone beyond hiring people. Leaders of other companies who have adopted the ladder tell me that the process of getting the ladder done and adopted internally has gone smoothly partly because they started with a known, widely-adopted ladder that their teams already felt comfortable with. People are getting used to the idea of an engineering ladder as a tool to help them progress in their career, not a tool to stifle them or create unnecessary hierarchy.

Engineers like to share and learn from each other. The veil of secrecy around HR-related issues has existed without questioning for a long time. Let's question it! When I proposed publishing the ladder, no one in HR batted an eye. We're all comfortable with sharing our source code, and we might blog or speak about the processes for running our teams, but few of us have ever shared the core documents for running our organizations. It is awesome to see Clef share their entire handbook on GitHub, and I hope to see more organizations share not only the processes that they use to run their companies, but the actual documents they rely on for core policies, procedures, and standards.

Open source culture requires you to openly care about culture. You can't open source what you haven't created or modified. I'm excited to see people truly caring about the craft of creating healthy organizational cultures, processes, and documents, and sharing them with the world. I'm excited that people are proud to show that they care about making the culture of the technical workplace better in tangible ways. This is the best of techno-optimism. We can share ideas, and make things better for the whole tech community and the workplace as a whole. I'm proud to be an early adopter of open source culture, and I hope many others will continue to join in the movement.