culture

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)

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?


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.