Host Intro (Gene Kim)

Up next we have Jason Yip, Senior Manager, Product Engineering at Grainger.

I first met Jason in 2019 when he was at Spotify, and so you probably know him from all the work that he did there. You've probably seen his talks. Before that he was at ThoughtWorks. Since then, he has joined Grainger, a leading broadline distributor of maintenance, repair, and operating products in North America. It was founded nearly a hundred years ago and now has over $15 billion in revenue.

In his talk, he talked about his new mission at Grainger to help achieve the CEO's new strategy of technology-enabled market share growth. He talked about many things, but he had so many great pieces of advice.

Jason, how are you doing? Thank you so much for being here today.

Maybe change Zoom source. How about now? Oh, yes. Looking good, looking good. Sound good?

Thank you for joining us today. I'm so excited that you and Claire will be talking about experience reports about the fantastic work that you've done in your respective organizations. Thank you for that amazing presentation that you gave on day three at the conference in August. Can you share what you talked about and maybe what you hoped people would walk away from it with?

Q&A (Gene Kim and Jason Yip)

Jason Yip: Yeah. I was talking about a way to think about larger transformations to create focus, and to focus on a few specific things that I came up with to go through that. If I would say the overall idea, it is just whatever problem you're looking at, you want to find these key points of leverage. You don't want to spread out your efforts, which tends not to work that well.

Gene Kim: In fact, one of the provocative claims that you had made is that having these transformation efforts was a magnet for everyone else's problems, which actually results in not great outcomes. Can you say more about that?

Jason Yip: Sorry, it just broke down a bit.

Gene Kim: One of the provocative claims that you made was that transformation efforts often become the magnet for everyone else's problems, which makes your work much more difficult to move the needle on important things. Can you talk more about that?

Jason Yip: Yeah. The general idea was when you do something of importance in an organization, everyone shows up to deal with their problem, because it could be the only opportunity for them to solve something. It's not like they're bad people. It's just an opportunity and they take it.

Now, the issue though is, from an organizational perspective, you don't necessarily want to spread your focus so far. I think even during the conference we talked about this. I think you made the comment, actually, that this isn't just for transformation; it would be for AI, whatever people want to do for everything. You really could say, "Hey, where do I want to find leverage?"

Gene Kim: And so what did you do about it, Jason?

Jason Yip: Some of this was just to say, if we step back from this idea of transformation, what are the actual key problems to solve? The first one was saying, "Hey, we want to move quickly, but we want to keep it safe." So let's look at: we're going to do stuff. How do I keep it safe? Don't talk about all the things that are associated, but just have that shared idea that you could then link things to so that we can create focus.

There are some other things too, but I'm thinking right now a lot about safety, because that one has repeatedly come up as a way to frame how to create focus with things.

Gene Kim: I am such an admirer of the work that you did at Spotify. It was always so thoughtful, so cerebral. Can you talk about what your role is at Grainger and specifically where you fit in the organization? One of the things that we plan on doing going forward is having everyone show their org chart. One of the key aha moments for me working on Wiring the Winning Organization is that the sociotechnical, social circuitry is the predominant predictor of performance. So everyone should show their wiring. Tell us how you're organized. Where do you fit in and who are your customers?

Jason Yip: This is actually a nice example of maybe the stereotypical issue of: there used to be a business side of things and a technology side of things. Then it eventually shifted. So now there's a product side of things as well as an engineering side of things, which helped a little bit at the time. But now they're trying to come together.

Doing that come-together thing is primarily what I'm trying to help with. But then there are some other areas underneath engineering, like reliability, and your standard: how do you shift pretty much every group to think not just, "Hey, I'm doing a service and I'm producing tickets or whatever," but to say, "Hey, I have customers, and we're in this chain that produces value to a customer." It's almost like the standard value stream thing.

My role is, I'm just kind of in the middle of that. I used to report to the engineering leadership; now I think they allocated me more to the platform area. But it is still this boundary-crossing. Even just a discussion of org design is like: there is what it looks like on paper, then what actually has to happen in practice to make producing customer value, which is always a little bit messier.

Gene Kim: It sounds like, both at Spotify and here, you are really an internal consultant. You're on staff to help, ideally, senior leaders solve important problems, and you measure your success by whether you can help your clients succeed. Did I capture that correctly?

Jason Yip: Yeah, I would say so. I think sometimes it's almost trying to role model what you want leaders to be doing. I think a lot of times, when we do these kinds of shifts, it's not like people don't want to do it. They just don't know what it looks like. It's difficult to, I don't know, say almost unfair to expect someone to just jump to a different way of working.

Gene Kim: Maybe a fraught question: you've often described yourself as a coach, and yet in this technology community coaches sometimes get a bad rap for various reasons. When you look around the industry, what are the things that great coaches do versus coaches that give coaches a bad name?

Jason Yip: I think there is some aspect when people say coach, they're thinking of it like a life coach type scenario. I don't want to say there is no value in that; it's just that's not really the problem we're trying to solve.

It's not entirely correct either, but I would almost lean more towards, if you think about coach as in more like athletics, professional sports type stuff, where we're in this game that we're trying to win. You're still trying to help people succeed, but it's not, "Hey, maybe they'll find it within themselves to win." There is still some aspect of skills development and partnership there. I think that's the difference.

Gene Kim: One of the stories we talked about, maybe attributed or not attributed, is we had a friend who was in a meeting and this person said, "Did you really hear what the CEO said? The CEO asked, what do I get out of this?" This person had to say, "I'm not sure if you really understood the question. Basically what this person is asking is, what am I getting for my money?" That should trigger you into an anxious state. Can you talk about that?

Jason Yip: Yeah. There are two aspects to this. One is the emotional intelligence aspect of just saying: people say stuff, but then depending on their cultural background, they may not actually say it; they're just hinting at it. You have to be able to interpret that.

The other one is: why are you able to read that? It's because you understand the larger game. The larger game is: we are an organization, we have costs, we have benefits, where the trade-off is happening. I expect the CEO to be thinking about stuff like that. So when they say something, I'm using that frame to go, "Oh, wait a minute. Okay." Because if you were in that position, you would be having the same thought, which allows you to do that interpretation.

It's almost like if you're trying to help develop a leader to understand, you need to understand that role, so you know when he or she says that, that's why they're saying that. It's within that context. It's not just an offhand comment. Some people, they're almost like, "Oh, I'm thinking of it as if I were just a team member." They're not thinking, "If I were CEO, why would I say that?"

Gene Kim: Can you connect the dots forward a little bit? Once that person has the realization that that's actually a question fraught with importance, what can I do to better respond to that? If even being asked that question is a red flag, how do I not get there in the future?

Jason Yip: I think it comes down to this: when we talk about accountability for outcomes or accountability for impact, part of the reason why people emphasize that so much is because that answers that question.

If you can imagine, even if you're a leader of a large organization, if you could say, "Every team or every department I'm responsible for is going to come to me already with: this is how much it costs for me to do my work, and this is the level of impact I'm providing for the company," then that makes the job easy. That's the idea: if every layer there is doing that, it becomes an easy back and forth. I shouldn't say it's easy; other things show up. But you start to get this more mature, useful interaction.

I almost think that is the response. It's not like you're in trouble. It's just more: this is now how you fit. There is less friction now in terms of what we're all working towards.

Gene Kim: Another question I've been dying to ask you since your presentation in Vegas is: you're in this coach role, a staff role, where you don't have the line of responsibility. You're in a position where you're supposed to help people in line-responsibility roles. Where do you find other good coaches? Where do they come from? Do you seek them out? Do they seek you? What's the criteria you use to establish whether someone is going to be a good coach or not?

Jason Yip: Do you mean internally or externally?

Gene Kim: Either, both.

Jason Yip: Internally, the way I think about it is: who within the organization is trying to make something happen? I don't really care what title or role it is. You're trying to make something happen, and you get together and try to do that.

There are also some roles, somewhat obviously people in the more senior leadership roles, as well as what we call the staff-plus engineers. People where the expectation is that you are doing that type of stuff. You're trying to recruit people like that.

Externally, I guess it's somewhat similar. I don't even look for the background. It's more like, if you have that kind of intention to make something happen, whatever that happens to be. "I'm going to learn whatever skill, make whatever relationship, because I want to create the impact." I think that's what distinguishes.

Gene Kim: Could you say more about the staff-plus type roles? What does that person look like? What are the signals that you look for?

Jason Yip: That's just the formal structure. Most technology companies have this thing where you start as an engineer, you're working on team stuff, and then you graduate up. Grainger has these numbers, but I just say they're kind of staff, because you use different names. Staff engineer is a typical thing, but it's where you're no longer just on a team. You're now looking at a broader system, and you build that up: all systems related to an area of stuff, and then broader than that, and so on and so forth.

The thing is, the level of ambiguity starts increasing. A typical thing is if you go, "Here is a specific problem, and I want the details before I work on it," versus, "I have a general vague sense of a thing," and you go, "The person who's supposed to turn that vague sense of thing into a very specific thing, that's you now. It's not someone else. It's you." That's the step up, and then it keeps escalating in terms of ambiguity.

Gene Kim: You are a systems thinker. When you look at the landscape of these very qualified, very talented staff-plus people who are great at ambiguity, at what point do you start asking questions like: is their highest and best use in the organization that's doing the work, or do they belong in this internal bench of consultants? Do you care? How do you determine?

Jason Yip: I think there are different things. Will Larson wrote a book called Staff Engineer, and he talks about different archetypes. When you get larger, there is not just one problem. There are some things where I need someone in the field. But then there is also the meta problem. Then there's the, "Oh, we have some weird cross-boundary spanning problem," where there is no one. Okay, that's probably you.

A lot of times, too, I need a partner to other roles, like product or business people, but I need someone who has this technical capability and can actually talk there. All these problems exist simultaneously.

The only thing I would say is, unless that single team is incredibly important, they probably shouldn't be just on one team. Depending on the business, most of the time I say that's a very rare event.

Gene Kim: This is a community of technology leaders, and leaders not just as measured by title on the org chart and number of people in their responsibility, but also individual contributors. What advice would you give to technology leaders who are on the individual contributor track?

Jason Yip: The advice almost ends up being somewhat similar. The only difference between an individual contributor versus someone with people management is that even an individual contributor, as you increase impact, you start mentoring and supporting development of people; they just don't report to you.

That sometimes even helps because you have to recognize you can't just force them to learn something. Generally, I would prefer the people manager to do the similar thing. So the criteria is very similar.

The individual contributor may, even when they get bigger, also tend to attend more meetings too. So it just ends up being maybe a slight leaning toward how deep you get into some of the details. But the idea of increasing impact through relationship, through understanding context, developing people, all that — that game is the same. It's just more, you don't have to sign off on time sheets, I guess.

Gene Kim: Your presentation was so great to see, not just in the unicorn Spotify context but also in the Grainger context. Can you tell us what you're working on these days and any help you're looking for?

Jason Yip: Randomly, I'm helping with a migration. You have old stuff, you have to make it into new stuff. That problem itself is an ongoing thing, so it's worth trying to frame that correctly.

In terms of help, generally other people who are doing this kind of older organization turning into a newer organization, that transition. It's always useful to hear what other people have seen in that space, and if what I'm doing makes sense or is ridiculous.

Gene Kim: In order for people to act on that, I think they just need 10 more words of what type of migration.

Jason Yip: The biggest part, in my opinion, is not so much the technology. It's shifting to more of this product operating model.

Gene Kim: Very good. Jason, thank you so much for joining us today. I look forward to future adventures ahead.

Thank you so much, Jason. Right on.