From Manager to Director and Beyond

hey there lead dev this is nick caldwell vp of engineering for twitter formerly vp of engineering at reddit chief product officer at looker general manager at microsoft happy to be here at the conference this year looks like a bunch of great content i've been really enjoying it my session is going to be about how you grow your career from manager to director this is one of the most important career inflection points that i think we all have to deal with one of the most challenging as well because what got you into your management role isn't what's going to make you successful at the director level okay first off what are we even talking about here you're thinking about getting into a director role what do directors do well directing is a middle management job congratulations you are now part of the machine um some negative things that will happen when you're a director first no one will tell you good job anymore right second you are very likely to lose your ability to code at the director level if you have to jump into the code base and start making urgent changes it probably is a sign that something has gone really really badly you have to build an organization that can get the job done without you getting your hands too dirty and for some people that's a really really tough transition to make third as a middle manager you have to interpret executive strategy and be able to explain and communicate it down into your organization as well as structure the organization to meet whatever those strategic goals are that's the essence of a middle management job right taking uh the strategy from the top interpreting it and building an organization to execute on that strategy now uh the cool thing about all this i think we talked about the negatives the cool thing about this is that at the director level you're gonna have unprecedented access to additional resources people you'll have much more authority and control over how strategy gets implemented you'll be able to contribute to some at some level to the development of that strategy as well the key thing here is it's a very different role from being an engineering manager you're going to have to learn how to think and operate differently at the director level and i thought i'd give you three three tips things that i've learned over the course of my career hopefully they will help you now the first lesson is you have to learn how to get off the floor and what does that mean exactly well if you think about your engineering team as being you know you being the head of a crew of line level engineers getting off the floor means that you have to kind of pop up get yourself off of working side by side with one team and think about how you're going to operate when you've got multiple teams to oversee at the same time now this is really tough it was really tough for me because being a line manager i i think is arguably one of the most fun things you can do you get to know every person on the team on an individual basis you think about how to map their wants and desires into the needs of what the organization is trying to accomplish you're responsible for the very fine details of day-to-day execution and success you know it can be really rewarding because you can see as a manager directly how your work and energy contributes into the happiness of individual people within the organization and i think that's a great starting point for every manager so a great manager needs to be all about empathizing with the people on the team and understanding their wants and desires and so forth and so on now a good director needs to remember what that was like but it's actually a very very different job at the director level you've got to think less about the individual one-to-one connection and much more about how the group as a whole operates because you're going to have multiple teams that you deal with i think for me uh this was a incredibly tough transition i up until i had around 30 reports i still did one-on-one uh meetings with all of them weekly weekly one-on-ones with 30 people it was getting to the point where my one-on-ones were essentially like 10 minute walking sessions would just go for a walk in the park so you know someone who loves that element of trying to get to know every person on the team this is something that you just can't do past a certain scale so what do you do instead you know when you've got to manage more and more people so at scale i think there's a couple different things you have to do differently when it comes to managing people first is how are you going to communicate what you want done you can't do one on ones and weekly meetings as much as you as you did in the past but maybe replace that with a better written communication in terms of newsletters or if you want to be modern think about doing maybe a weekly podcast we did that at looker and it was really really successful additionally you need to think more about how you're going to track progress at scale you know if you've got a small team one-on-ones you can or one kanban board you can pretty much you know keep on top of everything but when you're talking about managing three four teams at the same time you're gonna have to come up with a more systemic way to hold your teams and your your people accountable so for me i like to use at that scale okrs or other mechanisms where you still make it clear what you want accomplished all right but you're passing the responsibility for tracking the day-to-day execution toward those goals down into your engineering management level all right so that's tip number one people and how you manage your organizations are going to change you've got to get off the floor lesson number two is how you manage the shape and structure and resources within an organization the way this was put to me a couple years ago was was from a manager who i work for named kevin i really respected him quite a bit and he said nick when you're an engineering manager think about it as you're tending a single garden and you can carefully pot and plant water every individual flower at scale though when you're managing multiple teams it's more like you're in charge of parks and rec like you have to control the entire landscape you have to decide which hills exist or whether or not a path is going to or river is going to flow between certain neighborhoods it becomes much more about terraforming it's a real shift in mindset about how you think about the people on your team and and what you have at your disposal to get jobs done so this lesson is that when you become a director you have to ask yourself the question well what do i direct well when i was a manager i managed people and when i'm a director i'm directing resources and those resources are people funds contractors vendors all the different things that a company has at its disposal now become yours to configure and deploy to get work done and this can be a huge challenge because you've now shifted into a mode where you're popping up a level and thinking about how do i deploy this pool of resources to accomplish different tasks it's a very very different approach to solving problems because you're one level removed so some things that change here when you become a director first you've now got to think about your responsibility towards shifting people around or put another way reorganizing them i would claim that you can't really be a successful director until you've managed a reorganization and more to the point you might have to manage a reorganization that doesn't directly benefit you before you can claim the title of being a good director second you have to learn to work within the resources that have been granted you so when you're an engineering manager at least one of my favorite things to do was to always complain that i didn't have enough headcount and you might be able to get away with that to a certain extent when you're a director but part of the challenge when you're a director is learning how to work within the resources that you already have at your disposal and only until only until after you've really thought through how you're going to configure your team or deploy budget do you get the opportunity to go back to your executive team and say hey look i'm really tapped out i want more head count so it's a mark of a junior director to constantly be asking for more people it's a mark of a more seasoned director to be working within resources building a case for how the organization needs to grow and expand over time and then making that case if more resources are are needed i would say super advanced director maybe even knows when to give up resources and pair back in order to support other people uh or other teams within the organization as a whole a quick story about how i had to learn this lesson back at microsoft i had a team which was building a mobile business and intelligence application it was my favorite team it was the first mobile team that had ever inherited i grew it from about seven people to 20 people we had a blast i loved working with that organization the the challenge was they were building uh windows mobile applications and shortly thereafter uh you know the team or the organization decided that we weren't going to support windows mobile we're going to shift over to ios and android development and i had to take that team and break it apart and redistribute it and its members throughout the rest of the organization and it was one of the most painful things uh i had to do first time i ever had to do an organization that large and cut a project which i'd spent more than a year on but pretty obvious in retrospect that that was the right thing to do not only for the people but for the business strategy itself so lesson number two when you become a director you do have to think about managing a pool of resources and distributing them in the way that's most appropriate to achieve your business goals finally lesson number three this is your approach to problem solving and this was a a quote that one of my better managers gave me uh several years ago he said nick sometimes you've got to know when you need a bucket of water and sometimes you need to know when you've got to build a fire department now another way to put this is that when you're a director you think about pro solving problems with systems okay so you don't dive in and start coding or if you do something's gone really haywire within your organization instead you have to kind of hang back look at the situation and how your teams are operating the broader business context and you have to decide what systems you're going to create and deploy in order to meet business challenges over time all right so one of the cool things about this is that it gives you an opportunity to learn and experiment with many different ways of developing software when i was a director i remember the first year i got to have a team working in kanban another team which was doing a more scrum you know formal scrum methodology we had some teams with none of the above and for me that was an incredible learning experience because i got to understand that there are many many ways to approach software development and that at large at large scale it's less about being fixated on any one particular system and much more about developing a toolkit so that as new challenges arise you can reach into your toolkit pick the right approach or maybe adjust it slightly for the current situation and then move ahead with some confident that you've seen and operated using this system before and it's very likely that it will work in whatever new challenge that you're trying to address now i suppose it would be remiss of me if i didn't give you a warning here as you become a director you can't uh you can't take your hands totally off the wheel it's important to know when to dive deep when to grab that bucket of water and go put a fire out and that means i would strongly advise you to think about ways to detect when stuff is going wrong within your organization you'll find that when you get very very large teams 50 plus it becomes harder and harder for your people to feel comfortable coming to you with with problems so you've got to set up systems to detect when things are going wrong that can be weekly execution reviews or or okr check-ins certainly do that for me i also try and use skip level on one to develop relationships with people deeper in the organization or i always have someone that i can go to who i can trust to give me the real skinny on what's happening within my organization always have some way to un to know when things are about to go off the rails if you want to stick with the fire department analogies you've got to set up some smoke detectors okay so that's it three tips first remember you have to learn how to get off the floor second you're going to have to learn how to manage pools of resources at the director level and then finally you're going to have to solve problems with systems if you'd like to learn more about this the number one resource i can recommend it's pretty hard to find but hopefully it's still out there it's a presentation called the fast track to vp of engineering done by a gentleman named wade chambers hopefully that'll be available online if you google for it and if you would like to learn more from me i'm nick caldwell at nickcald at twitter or you can reach me on my website nickcaldwell.com hope you learned something from this presentation good luck in your journey from management to director and then hopefully we'll see you at the executive level soon as well good luck out there

Channel: Nick Caldwell

Views: 477

Rating: 5 out of 5

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Id: uWI_JRMwjR8

Length: 15min 2sec (902 seconds)

Published: Wed Dec 30 2020