Ahead in the Cloud: Don Weinstein of ADP

In this new episode of Ahead in the Cloud, we hear from Don Weinstein, the Corporate Vice President for Global Product and Technology at ADP. Interestingly, by the nature of his business, Don is able to see workplace trends not only in his organization but in those of ADP’s many customers. I’m sure you’ll enjoy reading about his “graveyard of old technologies!”

– Mark

What’s the coolest thing you’re working on?

The world of work is going through a transformation, where companies are re-thinking the structure of their workforce, embracing more agile, flexible labor models and taking new approaches to performance management. In addition, workers themselves are switching from traditional careers to more freelance opportunities where they can curate their own work experience – they are taking charge of their own careers, work assignments, growth and development and financial needs.

In response, we are redefining people management by building the next generation of technology that is aligned with where work actually gets done and by whom – in agile, team-based organizations with a dynamic and flexible workforce. We are ushering in a new era of “mass personalization” in the workplace, including the personalization of pay on demand – the ability to get paid in real-time, in a way that fits your individual needs.

Where do you see yourself in 3 years?

That is a hard question, because had you asked me that 3 years ago, I wouldn’t have imagined being in my present role. Instead of focusing too much on the future, my philosophy has always been to do my best possible work in the present, and somehow interesting opportunities and roles always seem to materialize.

Share someone who has been a mentor to you along the way, and the best lesson you learned from them.

I have been very fortunate throughout my career to have had many mentors, and took something away from every single one of them, but let me go deep into my past and offer something a little offbeat. When I was still in college, I took a job one summer working as an assistant in the maintenance department of a large building. Now, I wasn’t very handy back then, and still am not to this day, so whenever I was unlucky enough to pick up a particularly tricky maintenance ticket I would go to the supervisor and ask him to assign it to someone else. Invariably he would never do so, but instead give me a couple of quick tips and send me back out there while saying “You can do it, I have confidence in you.” And while not quite perfect, I was able to accomplish a whole lot more than I ever would have thought on my own. That’s a leadership lesson that has stuck with me to this day in trying to bring out the best in others.

What’s your favorite Amazon leadership principle and why?

They are all very good and broadly applicable, but if I had to pick just one, it would be that Leaders Hire and Develop the Best. Running a very large organization such as ADP’s Global Product and Technology team makes me keenly aware that all of the actual work gets done by the people on the team, and if you don’t have great people, the rest of the principles won’t really matter.

How do you learn about new technology and its potential impact on your business?

By looking beyond the boundaries of our current industry and staying curious about what is happening in technology in every part of the world, from consumer to enterprise, software to hardware and beyond. In most industries, competitors spend so much time studying each other that their offerings tend to converge into a giant sea of sameness. Only by looking for reference models in other parts of the world, and testing their applicability back to our business and our customers, can we stay differentiated. One way I like to do that is by joining a number of diverse, cross-industry, technology advisory boards and networks, where I can meet up with peers who are the heads of technology across a vast and wide-ranging array of businesses.

How do you decide on where to prioritize your technology investments?

This is one of the toughest challenges of my role, especially with so many competing demands. Recently, we have broadly adopted the popular OKR framework, and spend much time aligning upfront on our business-wide objectives. Whenever we do a good job of that, the technology prioritization problem becomes much easier. However, it is not always easy to get our business partners to align on their over-arching objectives and key results.

What’s the most interesting thing on your desk right now?

One item that grabs attention are the tombstones we issue to commemorate every time we sunset a legacy application, which has been a key part of our technology modernization. In fact, we’ve been making so much progress that I have a whole shelf above my desk dedicated to these tombstones, so many that it resembles a graveyard of old tech.

What does your morning routine look like?

I’m an early riser. I try to go to the gym first thing in the morning every single day. It’s a great way to start the day by clearing my head and doing something good for myself before the whirlwind of each day’s work takes over.

What are your top 3 book recommendations (personal or professional)?

• Moneyball (Lewis)…I still consider this the best business book ever written, and for me personally it opened my eyes to the potential for Big Data to impact just about every single industry, from Baseball to Wall Street.  It has had a major influence on our product strategy at ADP, by leveraging our treasure trove of data to derive fact-based, data-driven insights about the world of work.
• Leonardo da Vinci (Isaacson)…everyone in the world of product development can apply lessons from perhaps the world’s all-time greatest inventor and creative genius, such as his insatiable curiosity and incredibly high standards for excellence.
• Sapiens (Harari)…how do you package the entire history of humanity into a single book? With great writing!