Get on Track

Introduction

Idon’t understand the difference between program management and engineering management so I don’t see why we need this at Zendesk," said Morten Primdahl, cofounder and then CTO of Zendesk, during my second round of interviews for the role of creating a Program Management Office ( PMO ) for the product development organization. His comments were an auspicious start to say the least!

A year and a half later, Morten and I were walking along a street in Copenhagen, Denmark, where Zendesk was originally founded, having a very different conversation. She’s awesome! exclaimed Morten, speaking about my (then) lead program manager for product development. When I pressed for details, he opened up:

She’s effective because she just blends into meetings, becoming part of the team. She’s respectful about what’s going on but keeps bringing up questions and picking up dropped balls in a very nonintrusive fashion. The team was struggling with how to move forward on developing a very broad new set of services and she helped us break down the work into meaningful parts with a timeline that made sense. Her tone is always pleasant, and her demeanor just makes it a pleasure to work with her. In my past experience with project managers—the closest I’ve been to working with a program manager—that was just not the case. She’s very much the exact kind of person I hope Zendesk can attract to help us keep things good while growing.

What a difference eighteen months can make.

Several months later, Morten visited the San Francisco headquarters of Zendesk. He stopped by to say hello and asked me how things were going, so I told him how the PMO had expanded and was continuing to grow. He marveled at the growth and the value the PMO brought to the company and encouraged me to write a book that would tell people how to do what I had done. Well, Morten, thanks for the encouragement! My goal with Get on Track is to offer information and guidance to companies and executives who are interested in creating a PMO, as well as individuals who are interested in becoming effective program managers or want to hone their best practices.

At its core, program management is all about strategic execution. A company has a vision for what it wants to become. That vision provides the foundation for a long-term strategy, and then a set of annual goals and desired outcomes to move that strategy forward. Program managers put in place programs to drive successfully to those outcomes ensuring that the work done by the teams they support is derived from those company goals (p. 11).

In contrast to project management, which is more vertically focused and more domain specific, program management is focused on broader strategic goals. Successful program management drives alignment between several organizations in one company—for example, engineering, product management, marketing, and sales—toward a common goal. That goal might be the release of a new software product or service, implementing support for the General Data Protection Regulation (GDPR), or rebranding the company.

When I started out in the industry, working in program management wasn’t a career goal. I had no idea the discipline even existed when I was studying computer science in college. I’ve spent the majority of my career working in Silicon Valley with the exception of a three-year stint in France. Over my career, I’ve worked at small-, medium-, and large-sized companies and held roles in software development, product management, operations, technical support, and localization. Those experiences gave me a rich understanding of how software is designed, built, deployed, and supported and how companies of all sizes are run. It’s worth noting here that although all my experience in program management is in the software industry, program managers are found in governments and across many industries, such as biotech and aeronautics. The skills required for a program manager in any industry are generally the same. What varies is their subject matter expertise.

I first became exposed to the role of program manager when I was working in France. At that point in my career, I had worked as a software engineer, product manager, and technical support engineer and also spoke both French and English. I was asked to take on the role of technical program manager that required me to guide the delivery of product features from initiation to launch, collaborating as needed across product areas, functions, and regions. It was a perfect blend of my skill sets. When you have a room full of people each with their own motivations and differing views about how to approach a problem, it’s good to know what is motivating that product manager, or what the engineering lead is thinking, as I did. I also knew that smart people don’t like to be told what to do; that influencing without authority is the way forward. I’ve seen firsthand the importance of bringing the localization lead into the conversation early because this can be painful for global customers if localization isn’t considered until late in the software development process.

Working in France also gave me experience navigating cultural differences. Language barriers are challenging and even more so when they occur across thousands of miles and in several time zones. Working in a remote office in Paris, France, far from the Silicon Valley headquarters, I experienced the entitlement present in the home office and the subtle expectation that the remote office should be the one adjusting working hours to the Pacific time zone. I watched as Californian slang was thrown around with abandon, confusing the heck out of the non–native English speakers, and throwing me into the stressful (and sometimes humorous) role of interpreter as I also tried to pay attention to what was being said in the meeting!

All my career experience folded neatly into my new life as a program manager, but it’s my deep belief that the most important abilities for this role are people skills. An exceptional program manager needs a solid understanding of the business together with strong planning and scheduling skills and the abilities to break down complex processes into meaningful sections, effectively communicate program status, and successfully mitigate issues and risks. But it’s people skills that make all the difference in this role. As a program manager, you need to build relationships with your team members and stakeholders and be empathetic to the team’s needs and concerns. But you must also remain objective throughout the lifecycle of a program by keeping its goal(s) in the forefront and leading the team to make the right decisions for the business. Over time, that objectivity builds trust, which comes in handy when you need to nudge people in the direction required for program success. And finally you have to be likable, because even with all the other practical skills in your tool belt, if you can’t get along with everyone (and I mean everyone), you simply won’t be successful at driving programs forward.

Since my time in France, I’ve held program management roles and honed my craft in a variety of software companies. I learned the value of taking a proactive approach by getting to know the team and the business, building relationships, learning what keeps them up at night so risks can be mitigated and programs stay on track, establishing trusted partnerships with stakeholders, all with the objective of moving the needle on company goals. Done well, the role of the program manager has a huge impact on a business and also results in great job satisfaction for the program manager. Now, imagine a whole team of these talented, like-minded individuals centralized in a services function, collaborating effectively and building bridges across the company to deftly move the company strategy forward. This type of organization can be transformative!

When I worked at Adobe, other program management teams often asked me what the secret to my success was. Why were the program managers on my team creating so much positive impact on the teams they supported? At Zendesk, people often said things to me like, We couldn’t have done this without program management, or, My team literally wouldn’t exist without your support. As people left Adobe and Zendesk for companies around Silicon Valley, they realized I had built something unique and came calling for advice. I’ve distilled all that advice into this book.

Get on Track is designed to take you step by step through the process of creating a Program Management Office (PMO). Parts One and Two are about building and running a PMO. Part Three is about program managers who make up the PMO and how they can level up their game so that the teams they support will make the same transition Morten did—from skeptic to enthusiastic supporter of program management. At the back of the book I’ve created a roadmap (p. 226) for you to explore as you build out your own PMO, but please feel free to refer to the topics most useful for your own situation.

In this rapidly growing field, it probably comes as no surprise that there are several books that provide information on the standards and principles of good program management. But what is missing is a book about how to create and nurture a PMO in companies currently operating without one. This book is for the business leaders I’ve spoken with over coffee in recent years who want to build a top-notch PMO, and for the program managers who want to know how to make program management work best in their company and what kind of people they’ll need to make that dream a reality. It represents all the effort I’ve put into developing the best practices that I still use today. So, please consume it with gusto and feel free to contact me at paula@pauladieli.com if you would like to know more.

1

What Is Program Management?

In the introduction, I referred to program management as strategic execution. The programs we put in place and drive forward are based on an understanding of the company vision, long-term strategy, and annual plan. But when I describe program management to businesspeople who might not be familiar with how it works within a company, I like to use a metaphor of a train to describe it—the sleek high-speed train (in French it’s called the TGV or train à grande vitesse) that whisks you into Paris. And on that speedy train, program managers are the train conductors.

When you are a train conductor, you are bound to ask and answer a lot of questions. For example, if the train is going from San Francisco to New York, you might be asked by a passenger how soon you’ll arrive at your destination and what stops the train will make along the journey. The conductor needs to know what the train’s route is, what the schedule looks like, how many passengers and staff will be on board at each stop, and who is responsible for tickets, meals, and repairs, as well as what to do when things get snarled. You’ll pass out passenger surveys at your train’s final destination to measure the success of your service.

Similarly, when a businessperson tells me they need a program manager, there are things I need to know to help them arrive at their destination on track. I need to know where the business is trying to go and how quickly. How will this program move the needle on the overall company strategy? Have commitments been made already? Is there a plan in place and who is involved? And what’s the driving factor behind the program? This could be something like releasing a product feature as quickly as possible or making sure the product meets the needs of the customer. Then we develop a plan that includes goals, timelines, resourcing, roles and responsibilities, and measures of success. I’ll talk more about that planning process later in Chapter Four.

Once the train starts moving, communication is a monumental part of what program managers do. Passengers like and need to know what’s happening along the way. In program management, formal communication takes place during cross-functional program team meetings (or program meetings for short): we align everyone on the next several milestones, make decisions to enable progress, communicate and discuss plans that have cross-functional ramifications (such as pricing or launch plans), and resolve any issues that may have cropped up. Status reporting is another type of formal communication in which we communicate program status, usually via email. But informal communication is equally, if not more, important than formal communication. When you drop by someone’s desk, hang out near the team you support, have coffee with key program team members, or build relationships with stakeholders—these are the times when the program manager learns what’s really going on.

Like a train conductor, a program manager is focused on cross-functional coordination. They bring in the various program team members at the right time. Some team members, such as those in engineering, might be along for the whole ride. But other teams, such as the legal department, may not need to get on the train until later, when marketing content needs their review. It’s important that the program manager can count on each program team member to do their job, but they won’t get into their business unless there’s an issue. This is just like the train conductor who doesn’t get involved in what the menu looks like but needs to know the food supplier will be at the station in the right place and at the right time.

Program managers need to be proactive. They need to know what the next few milestones (or train stops) are and to understand and mitigate risk. For instance, if the train is traveling through the Rocky Mountains in November when winter storms kick up, a good train conductor will call the track maintenance team ahead of time to ensure the branches overhanging the tracks are cut down before the train comes barreling through. They’ve taken this route before and know that if a branch or tree were to fall and block the tracks, it could slow down the train or, worse yet, bring it to a screeching halt. They know who their stakeholders are, who they can count on to deliver, and who or what has been problematic in the past. Similarly, if the program manager misses something that slows the program down or even halts it in its tracks, they’ll address the issue to get it moving forward again. Good, proactive program managers are always mitigating risk. They’re always thinking about what could go wrong and putting things in place to ensure they don’t.

Train conductors need to balance the needs of the train’s personnel and its passengers, especially if there is an issue like a delay or a missed stop. To do this effectively requires a cool head. Likewise, program managers must work objectively. The people working on a program often have diverse opinions, and it’s the program managers who facilitate conversations without taking sides and drive everyone to the decision that ensures the program’s goals are being met. Objectivity builds trust. When there is trust, program team members or stakeholders will alert the program manager to a risk (ideally before it becomes an issue), knowing that the program manager will solve it objectively in the best interests of the program.

Finally, a good train conductor is always checking in on the progress of the train’s journey and making sure the goals for the trip will be met. Program managers typically use retrospectives at the end of a program but often also upon completion of key phases, or legs of the trip, so they can make improvements along the way. A well-executed program ensures that the business runs as effectively as possible and that passengers are likely to return.

Now that you know how program management