Sunday, June 28, 2015

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.

Tuesday, June 2, 2015

The Trials and Temptations of the New Leader: "Cool Factor"

Being a new leader at a startup is hard for many reasons. You think you're good at a lot of things, only to discover that you're not. You were fooled by success gained inside of a company with hidden structures that helped you succeed, the invisible backpack of big(ger) company privilege.

One very common area of weakness is recruiting. When I started to lead engineering at Rent the Runway I fancied myself pretty good at recruiting. After all I had done it well in prior gigs, I was friendly and engaging in interviews, so I'd be fine! Of course I quickly realized that startup recruiting is enormously different than at a company with a whole recruiting department sourcing candidates, making sure the process goes relatively smoothly, and of course, paying them fat industry++ salaries. Outside of this structure you experience a world where you reach out to so many people and get nothing but silence, blank stares, or polite dismissals. Your CEO tells you that you've gotta sell, and asks for your sales pitch. And often, faced with a string of failures and pressure to grow, you land on the need to do something "cool" with technology to up your "cool factor."

You know what I mean. Chase the buzzwords: microservices, Go, big data, event-driven, reactive, functional, etc etc etc. The only way engineers will want to come work for me on my relatively straight-forward application development is if I give them the carrot of Cool New Technology!

I have learned a few things over the years, and one of those things is that usually engineers that are only interested in Cool New Technology are not going to stick with your Boring Business Problem for long enough to be worthwhile, or worse, they'll stick with it long enough to leave a trail of one-off solutions that no one else on the team understands before they walk away and leave you holding the bag.

If you're tempted to reach for Cool Tech, then I'm going to guess that you're not at a company where the primary challenge is purely technical or scaling. Instead, the interesting problem that your company is solving is almost certainly a combination of a) figuring out how your business, possibly the first of its kind, is going to survive, and b) growing, changing, and evolving to create a functioning organization. Once your company is successful, many of the problems that seemed trivial become surprisingly challenging to solve at scale, but in the early days oversolving with cool tech only leads to distraction from tackling the real challenges.

So resist the urge to adopt any technology for the cool factor of recruiting. Instead, look for people who want to own big parts of the system, who are interested in the business, who are really passionate about the customers you're serving, who are looking for leadership opportunities. Don't undersell the opportunity you have just because it isn't Cool New Technology. Be honest with yourself about the real problems that make you excited about the business that you're in, and that's where you'll find your best sales pitch.

Thursday, May 21, 2015

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)

Saturday, March 21, 2015

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.

Sunday, February 8, 2015

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.

Tuesday, January 13, 2015

A Letter to My Team for Review Season

I wrote this email to my team and sent it yesterday. It covers some of my thinking about reviews, a perennially controversial topic everywhere. Even though I believe that it is not a perfect exercise, I think that the benefits can outweigh the downsides, and I cover some of my thinking here.

Team,

As you all know performance review season is beginning. I thought I would take this time to talk to you about the goals of the review process, why I personally believe in it despite its many downsides and inconveniences, and what I hope that you can all get out of it.

Why performance reviews?

The first purpose is to give everyone a time to reflect on the past year, the accomplishments and growth that we have each individually achieved, and to celebrate that. Yes, celebrate it. Take the time to think about not just what didn't go so well, but what went really well. Part of the training your managers receive is to dwell on the positive parts of the review. Many of us want to skip over that and get to the "areas for improvement", but there is as much value in knowing what you are good at and what others appreciate in you as there is in knowing what to change. We celebrate accomplishments throughout the year, but it's also important to take the time to sum them up. Learning happens when we study our successes as well as our failures.

Speaking of successes, spend time yourself accounting for them. Self-promotion feels bad to some people, but it is important to learn the skill enough to write about your accomplishments. Even if your current manager is excellent at tracking the things you have done and the skills you bring to the table, you will have many managers throughout your career and they will not always have this ability. We can work to change the world so that self-promotion isn't so important, but it is good for you to be armed with the basics for your future career. If you need help with this, talk to your manager, or feel free to stop by my office hours.

You will also get a chance to write and see a summation of areas for improvement. Hopefully you will take the act of writing this for your peers and manager seriously. This isn't the time to be petty but it is the time to be thoughtful and honest. Feedback for areas to improve is something that you hopefully hear as needed (and not just once a year), but we don't often have the time to take in the entirety of observed habits and behaviors throughout the year and comment on trends. I have gotten some of the most valuable feedback of my career throughout this process; if you're curious ask me about the time I got review feedback that told me I was creating a "culture of fear."

One of the most important goals of this exercise is for us to think about our company values and to reinforce those values throughout the team. You've all seen the list of company values over and over again. We celebrate them in team meetings and we talk about them in reviews because the values are what bind everyone in the company together. We can all exhibit them through the lens of our individual roles and skills. You were hired partially because we believe that you share many of these values and thinking about the great things you've done as expressions of these values helps us all remember what we stand for as a company.

Finally, there is the goal setting section. Goal setting is hard, and there's no reason it must be tied to the review, but this is a good opportunity to check in with your manager about what you like about your current job and where you want to change and grow. Do you want to speak at conferences? Become a tech lead? Move into mobile development? Start managing people? Maybe the answer is just "I want to keep getting better at what I'm doing now" which is totally fine. This is an opportunity to start making a plan with your manager about how you're going to achieve what you want.

I promise that your manager will put in effort to give you a thoughtful review and help you grow, and I hope that you will put in the effort to write thoughtful reviews for others. The prose is less important than the content, a bulleted list that says something meaningful is fine if that is your style.

When this is all done I welcome feedback from all of you as to how we can make the process better. I have gotten a lot of value out of my reviews over the years, above and beyond regular feedback, and I believe we can make this process worthwhile for all of us.

Happy writing!
Camille

Saturday, January 3, 2015

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.