Lesson: Cruel Empathy with Kim Malone Scott

Step #8 Case for Management: Management is the part of a startup that does not scale

I believe that great management is absolutely vital to an organization. And by the way, I hate the word “management,” so if anybody has a better word for it, I'm open to it, but we'll just use the word “management” for now.

I think that it's tempting to say that management doesn’t matter or is unimportant because it's the part that doesn't scale. I don't think you can manage more than a handful of people if you're going to really manage them well. It takes tremendous amount of time, it's incredibly personal, and it happens one-on-one. So it doesn't and can't scale. I think particularly in Silicon Valley, which is the land of scale, it's part of why people are ambivalent about management.

There are plenty of companies that have terrible management that are very successful. I would say it matters almost from an aesthetic or moral point of view. Do you want to create a place that is hellish to work? Or do you want to create a place where people love their work and can do the best work of their lives? For me, the difference between Dilbertville and the place where people love their work and do the best work of their lives is management.

What are the break points in size of company and how does that impact management? I personally have always tried to have only five direct reports, which I realize is crazy. So many people, especially in Silicon Valley, have 20 or 30. The reason is, I like to have a one hour, one-on-one every week with each of my direct reports and it's hard to spend more than five hours a week in one-on-ones unless you're a shrink or something. So five is, for me, a magic number.

It’s interesting, at Google there was a rule of seven. You couldn't be a manager unless you had seven direct reports. The reason for that was that they were trying to keep organization flat. That's not crazy. Five or seven, there's not a big difference. The problem though is that, especially in an organization that's growing fast, you often have a lot of new managers. I like to have a new manager have one or two direct reports because if they screw it up, then they're screwing up the lives of three people, not the lives of seven. There's debates on both sides of that.

I think that you don't need a lot of process up to about a hundred people. You can run things pretty informally. Once you get past a hundred you have to really start being very conscious of putting in place a process that doesn't destroy the magic, process that doesn't feel like process, and process that actually saves people time, and doesn't ruin people's lives. That's a really tricky thing to do.

Once you have offices in different time zones, or at least in different cities, even if it's not a different time zone, there are things you have to do that are harder. Some of them are around just having great video conferencing equipment, big screens everywhere, and that sort of thing. Being very conscious of how you conduct meetings, so that people who are coming in remotely can really participate is important. That's another break point.

Once you have different geographies, there's a regional functional dance you have to think through. When are you going to structure organization by function? When are you going to structure by region? There's no one right answer. No matter, it's definitely a “damned if you do, damned if you don't.” You just have to be aware of your poison, picking it, and then managing against it. Those are some things that spring to mind.

I think a flat org structure is a myth. A flat org structure means that every manager has 60 or 50 or 40 direct reports, which means they can't really manage. They can't take time to give people impromptu feedback. You can't give 60 people impromptu feedback very frequently. They can't take the time to provide direction. Provide direction is actually the wrong way to think about it. When you hire great people, the people tell you what to do. You don't tell them.

You can't listen to 60 people and figure out what they ought to be doing. You can't take the time to think about every person on your team. Who are the people you need to give the next growth opportunities to? Who are the people who are great at their job and you need to honor them for that, but you don't need to promote them? Who are the people who, for some reason, would appear to be stuck in the middle? How do you get them to either perform great or get them to go somewhere else where they will perform great?

How do you figure out who are those people that you have on your team who ought to be doing great but aren't? Is the problem you? Is the problem that you put them in the wrong job? Is the problem some sort of temporary thing? Or is the problem cultural fit? How do you figure out what you're going to do for those people?

How do you take the time to fire the people who are not doing well? Firing people takes a lot of time and if you don't do it, all of your top performers suffer. All of those things take time and to do them well you need to spend a lot of time with the people. It's important and it doesn't scale.

I believe that management can be learned. I believe that everything, almost, can be learned but management, in particular. I don't think there's any such thing as “people people” and people who are not “people people.” We’re all human beings.

I think the most important thing to being a great manager is not to want to be a manager, but to want to do the things that managers do. If you don't want to give feedback, if you hate giving feedback, can you learn to do it better? Yes. But should you do something that doesn't require you to do something you hate to do? Yes.

Can you learn how to listen to a group of people then help them set their own direction, and then make sure that gets communicated in a clear way? Yes. Anybody can learn how to do that. You don't have to have some sort of magical oratory skill. It's more about listening than communicating, actually. Can you learn how to assess talent on a team and figure out how to give different people different things so that they're growing in their careers? Yes. These are all things that can be learned.

One of the best managers I ever worked with in my career is a guy who's at Twitter. His name is Russ Laraway. He used to work at Google. He developed a training there that helped new managers learn how to have a get-to-know-you conversation with their employees. The truth of the matter is, everybody already knows how to get to know another human being. But for some reason, a lot of people think that when they're in the role of manager, it's no longer appropriate to get to know. It's more important than ever to get to know people. It would be like saying, “It's not appropriate to get to know your spouse.” I mean you have to get to know them.

The key of education is about educo. It's about pulling out of people what they already know. That's what Russ did for the managers on his team. He helped them use these talents, these skills that they already had developed, but for some reason weren't employing.

It's very interesting. Every company is very different. Every company that I've ever worked at has a very different ethos, a very different personality. The starkest difference and most interesting was the difference between Google and Apple. If Apple hires experts, Google hires general athletes. If Apple believes in focusing and only doing four things, Google does a lot of things. If Google says, “right,” Apple says, “left.”

The core fundamentals of management are very similar across organizations. There are organizations that are more direct, and cultures are more direct. There are cultures that are sort of “nicer.” Feedback is equally important at both of them. It's probably harder to teach the feedback at the nicer cultures than it is at the more direct cultures. I might put a different emphasis on one thing versus another thing in the two different cultures, but the problems are all the same.

I would say you would expect at the very direct culture there's going to be more problem of the jerks and you have to tame the jerks. I've never seen a place where that's true. The biggest problem everywhere is the problem of cruel empathy; the problem that people are pulling their punches. Even jerks pull their punches. Maybe they pull their punches for different reasons than truly kind people, but everybody tends to pull their punches. It's risky to tell people things they don't want to hear.

I think that feedback is important everywhere no matter what the culture is. You’ve got to build teams everywhere no matter what the culture is. You've got to make sure that people are lining up behind the direction no matter what the culture is. It's different.

At Apple, in a sense, it was easier because the way decisions were made were very clear. But still you had to line people up against the direction. At Google, even though it was more of a, “let a thousand flowers bloom,” kind of approach to innovation, you still had to do some things and not do other things. You had to line people up against a particular direction.