John Caplan, President of North America B2B at Alibaba Group has spent over 20 years in executive and leadership positions in business. Caplan talked to Thrive and shared his wisdom about everything from successful meetings to managing workplace stress to practicing better communication

Courtesy of John Caplan

Thrive Global: What is your morning routine?

John Caplan: I like to start my day around 5:00 to 6:00 a.m. I will frequently do a call with colleagues in China or Europe, and then head for a workout. I then cook breakfast for my daughter — I make a wicked good French toast — while we are all having family time before heading into work.

My mindset each morning is where I try to get centered on what’s important, what I feel grateful for, and how I can “start” the day open-minded to what will come. For me, it’s important that I try and earn the trust of our team, customers, and partners. I think that the best days are when I think through the framework of what is important and how it intersects with what is urgent. If I have clarity about these things, and can edit out the unimportant and not urgent, each day can be fun, productive, and I can learn something that can help us help our customers.

I travel frequently — I like to visit the SMBs that use our platform, we host events around the globe, and then I go to China many times a year — my routine in China mirrors what I do at home in N.Y.C.

TG: What is your company’s culture like?

JC: At Alibaba Group, the company is driven by a powerful set of values which guide and shape the culture of our teams. My two favorite values are:

  1. If not me, who? If not now, when?
  2. Trust makes everything simple.

The first value — “If not me, who? If not now, when?” — resonates with me, because although we are 8,000 miles away from headquarters in Hangzhou, China, we are transforming and growing The value emphasizes that every employee is empowered to drive healthy change and disruption, and our growth thus far would not have been possible if we had not cultivated an environment of change makers. I think of this as creating an environment where “healthy disruption” is possible, where people who have courage, commitment, and drive can reimagine how our business can better serve global small businesses. Companies make lots of noise about their culture, but there is something remarkable about how the Alibaba team cherishes them, talks about them, and tries to live them.  

The second value — “Trust makes everything simple” — is about creating a culture of trust for two parties — trust for small-and-medium-sized businesses to do business globally and trust within our company. With over 100,000 employees, it is impossible to know every person and his or her role. Although we don’t know everyone, we need to be able to trust one another’s work and values so that we can seamlessly achieve the same goals.

TG: How do you practice mindful communication at work? What are some ways managers can practice better communication?

JC: At, we foster an environment of open communication. This means we are fully transparent about the business, including strategy, business and personnel decisions, to ensure each employee feels 100% part of the business as well as the decision-making loop. We also host weekly town halls where employees communicate anything that’s on their mind.

I try and improve my communication by being transparent. Every day I’m asking myself how I can help everyone around me achieve their goals — personally and professionally. I run a monthly class with new employees to discuss best work practices, talk about how aligned we feel about what we’re working on, role play how to process failure, frustration, and disappointment, and discuss how we can best contribute, learn, and grow at our organization. It’s important to me that we are authentic about who we are, and at the same time share common goals. Our diversity and differences are the source of our strength, and our alignment is what drives our results. 

TG: What small steps do you use to accomplish your ultimate goal? How do you stay on track?

JC: Realistically, I think people can only achieve a few impactful things every week, month, quarter, etc. Therefore, I keep a short list on my desk of the high-impact goals I want to accomplish, narrowing my focus and eliminating any distractions. The more I edit, the better our results are.  I like to think about it this way — 50% of projects we work on will fail — so let’s only work on a small group of truly transformative initiatives.

To stay on track, I come to work every day with zero credit, and try and earn credit by the end of each day. It’s about humility and not being afraid to get things done, no matter what it takes.

TG: What is one small habit that has improved your life significantly?

JC: I try to get seven hours of sleep, which allows me to feel refreshed each day.

TG: How do you approach workplace stress?

JC: People often think that they need to hold in their workplace stress, especially while at work. I think it’s actually important to articulate your stress with colleagues so that together you can put the stress in perspective or solve the issue.

For me personally, it’s also important to compartmentalize work and personal stress because I do not want one dominating the other. Work stress is never as bad as in my imagination, and the more we’re able to articulate the stress we have, and are open about it, the more we’re able to contextualize and conquer it.

TG: What are three things that help you thrive outside the office? What about inside?

JC: The number one activity that helps me thrive outside of the office is spending time with my wife and children. I love sharing a meal, whether it’s cooking at home or discovering new restaurants. Taking long walks also plays a major factor in helping me thrive. I’m a New Yorker, born and raised, and I still find exploring the city fascinating. Being able to walk around and let my imagination run wild is restorative for me. I love going to the Museum of Modern Art — I find personal inspiration surrounded by magnificent works of art. I’m a dedicated Brooklyn Nets fan — I never miss a game.

I work with brilliant people and I love to collaborate, learn, and build with them. My notetaking keeps me organized. I roll up my sleeves. It takes thousands of hours for a company to be successful, and I’m all in.

TG: When you notice you’re getting too stressed, what do you do to course-correct?

JC: I look at the data. Talk to the team. Brainstorm solutions. Listen for the best ideas. Ask people what they believe. And ask them how I can help.

TG: What is one key piece of advice for someone newly entering a management role?

JC: It’s important for new managers to care about the people that they work with. Not fake care — actually be aware of and interested in the lives of the people you work with. And then, be aware of your impact on your team members’ success. To achieve the best results, managers should meet with their team once a week to discuss goals, progress, and any problems. I think the team is often better equipped to build than the manager – so ask “do you believe in what you’re doing? What’s the KPI? What are your obstacles? What help do you need?” These questions guide me — and if you ask, listen to the answers.  Managers also should not ask their team to do something if they would never do it themselves.

TG: What type of work environment do you thrive in? Why?

JC: I work best, and I’m happiest, when I’m surrounded by diverse and creative entrepreneurs who have an appetite to get things done.

TG: What are your travel tips for staying on track during long trips?

JC: Because I go on long trips to Asia, I stick with consistency to minimize the impact on my body and mind. This means that I take the same flights back and forth and stay in the same hotel because the predictability helps me manage my schedule effectively. To make sure I’m productive, I plan my schedule in advance so that I’m prepared for each meeting. Additionally, going to the gym and eating healthy is critical to ensure I’m not too exhausted with all the travels.

Work trips, however, should not just be work. It’s beneficial to go out with colleagues, whether it’s for a great meal or weekend trips. These outings will make work travel more enjoyable, in addition to more culturally immersive.

TG: With so many distractions and interruptions coming at us throughout the day, what are your tips to stay focused?

JC: The only way to eliminate distractions is to be disciplined on what matters. Tracking and measuring data will help decide what matters. If something cannot be tracked, then you likely shouldn’t do it.

TG: What is your favorite hobby? Do you have a certain tool or trick that helps you allocate time for your out of office interests?

JC: Long walks are my favorite hobby. I find it meditative to walk and let my imagination go wild, allowing my mind to relax. Rooting for the Nets. Spending time with my family. Building companies.

The best ways to allocate time for out-of-office interests are to make them a habit and always be true to yourself. Sustaining personal interests will help you thrive in all areas of life.

TG: What is your relationship with feedback? Do you ever struggle to give or receive feedback?

JC: At, we receive 360 feedback. We have bi-annual reviews with direct reports and weekly one-on-ones. My colleagues and I, however, have a partnership and transparent approach with feedback. If someone is doing awesome work, the partnership is quick to compliment. If someone is dropping the ball, we’re quick to help. Our approach is not punitive but supportive.

I have no problem providing and receiving feedback. I love telling others they’re doing a great job, and if they’re not delivering, they’re quick to say this isn’t working and ask for help. I ask for constructive feedback from my team and partners. I believe we can always improve, both personally and professionally.

TG: What are three things that make a successful meeting?

JC: To hold a successful meeting, a brief agenda should be sent around before the call. It’s important employees are discussing the materials instead of reading them during the meeting. It’s also essential to be completely direct during the meeting. The most important tip for a successful meeting is having an open environment. And to achieve that open environment, teams need to have a foundation of trust so they can comfortably share input or ask for help.

TG: What is your evening routine? How do you wind down after a long day?

JC: After a long day, I enjoy a really good glass of tequila and like to share a meal with friends and family.

It’s important to note that my work doesn’t feel like work. It’s complex, but I feel it’s a privilege to help businesses around the world. Time is too essential to work on something you don’t find meaningful. Each night, I come home with the same spirit I’ve always had — exhausted and excited at the same time.

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  • John Caplan

    President, North America B2B, Alibaba Group

    John joined Alibaba Group in 2018 to lead the growth of the B2B business in North America. John is leader with 20 years of experience as a Founder, CEO, and President/CMO. He is an entrepreneur and leader, with a track record of transformational innovation and results. Prior to joining Alibaba, John was Founder & CEO at OpenSky, responsible for building a world class ecommerce platform with a team that leveraged technology to unlock the growth potential of small businesses. Before OpenSky, John was CEO at Ford Models, the largest and most successful global fashion talent firm, with operations in 50 countries and across every aspect of the talent industry. He led the successful digital transformation and modernization of the fashion services industry and created the Ford Models Media business. Previously, John served as the CMO and President of John has a B.A. in English from the University of Rochester.