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Remote Career Development: Calendly’s Jeff Diana On How To Advance and Enhance Your Career When You Are Working Remotely

An Interview With David Liu

Be intentional: In a remote environment, you must be more intentional about being proactive and vocal when it comes to delivering or requesting feedback, recognizing successes, or helping people navigate career growth. This is what ultimately drives company innovation. It’s important to schedule recurring one-on-ones over Zoom, hold quarterly check-ins, and arrange project-based feedback cycles.

Career development is the ongoing process of choosing, improving, developing, and advancing your career. This involves learning, making decisions, collaboration with others and knowing yourself well enough to be able to continually assess your strengths and weaknesses. This can be challenging enough when you work in an office, but what if you work remotely? How does remote work affect your career development? How do you nurture and advance your career when you are working from home and away from other colleagues? How can you help your employees do this? To address these questions, we started an interview series called “How To Advance and Enhance Your Career When You Are Working Remotely”. As a part of this interview series, I had the pleasure of interviewing Jeff Diana.

As Chief People Officer at Calendly, a scheduling automation company with 10M+ users, Jeff Diana is responsible for the company’s people and workplace operations teams including engagement, operations, talent acquisition, learning and development, performance management, total rewards, and more. He’s passionate about cultivating the next generation of leaders in the workplace, helping people identify and lean into their talents, and showing the impact teams can have on organizational growth and success.

Thank you so much for doing this with us! Before we dig in, our readers would love to get to know you a bit better. What is your “backstory”?

After three years on Calendly’s board of advisors, I decided to join the company as Chief People Officer in September 2020. I was attracted to the company’s mission, leadership, people, culture, and our product, all of which are second to none. What excites me most about my role is that Calendly is at such a critical moment in its history where we are growing exponentially, hiring quickly, and innovating rapidly, which means there’s significant opportunity for the people function to help shape the culture of the business, people’s roles and careers, and the processes and programs we implement to drive team collaboration.

If you go back further, you could say my beginnings in the HR space began nearly 25 years ago after I earned dual Master of Arts degrees in Sociology and HR Management from the University of South Carolina. I went on to become the Chief People Officer at SuccessFactors, then the Chief People Officer at Atlassian. Prior to joining Calendly, I was a strategic consultant to several high-growth global software companies to help them scale their businesses and HR programs. I’ve also held various HR leadership roles at Microsoft, General Electric, and Bell South.

Can you share the most interesting story that happened to you since you started your career?

I don’t necessarily have a single story in mind, but I do have a realization I came to early on that led me to pursue a career in tech. That realization is an appreciation for the power of software when it comes to driving innovation and change. I’ve had the privilege of partnering with influential business and tech leaders from around the globe, across industries, and in various company stages. The incredible impact of the entrepreneurial mindset never ceases to amaze me.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

The funniest mistake I made was when I first started my career at BellSouth, an Atlanta-based telecommunications company. After winning a prestigious company-wide HR award, my manager and I were invited to a celebration lunch with the CHRO and other C-level executives. When it came time to order drinks, nearly everyone ordered lemonade or iced tea, while I ordered a glass of wine. I was young, new to the professional world, and light-hearted jokes were made about my choice of beverage. As an Italian American, I grew up with wine commonly being served or enjoyed at meals so I didn’t think anything of it. To this day when I see that CHRO, she laughs and says, “Do you remember the time you…”. What I learned from this situation was the importance of balancing reading the room and navigating workplace and cultural norms with bringing your authentic self to work. I learned to spend time reading and empathizing with my audience, consider the dynamics and perspectives involved in each situation, and uphold values to motivate people to want to come to work and contribute to the mission of the company. One of my big focuses as a chief people officer today is to cultivate a culture where each individual feels respected and supported to bring their whole self to work while being celebrated and embraced. This is how people feel empowered to do the best work of their lives.

What advice would you give to other business leaders to help their employees thrive and avoid burnout?

There are three key actions every leader can take to best support their people and company.

  1. Start by learning the core drivers of your people: Evaluate what makes your people tick, determine what matters most to them, and look to build a career experience that centers around these factors. By focusing on intrinsic motivators, you have a legitimate chance at tapping into the engagement drivers for each individual.
  2. Discover each person’s super power: We all have them. What is it that each person excels at based on their specific skill set and how do you set each person up to thrive and fully leverage that strength to add value to their team, the business, and your customers.
  3. Focus on forging strong relationships: Ask for feedback, listen intently, and show you care by the actions you take. We have adopted this strategy at Calendly by building a culture of feedback and giving permission to our people to voice their feelings, concerns, and ideas. This is the cornerstone of one of our values at Calendly, “Start with human.”

You may consider other tangible initiatives, many of which we apply at Calendly — such as redefining your performance feedback process to be one of equality (i.e. bi-directional feedback and reflection by both the manager and the team member) — to reach success through partnership. We’ve also partnered with a wellness coach to offer mental health classes during the workday and encourage everyone to enjoy our unlimited time off benefit to reset and recharge. We recently announced new company-wide vacation days beginning in 2022, including two days for Mental Health Awareness Month in May.

Ok, let’s jump to the core of our interview. Working remotely can be very different than working with a team that is in front of you. This provides great opportunity but it can also create unique challenges. To begin, can you articulate for our readers a few of the main benefits and opportunities of working remotely?

What we learned during the last 19 months of the pandemic is that work can happen from anywhere. The pandemic and the demand for flexibility at work has required companies of all sizes to re-evaluate their operations, infrastructure, and how work gets done. For example, we decided to permanently shift to a remote-first, but not remote-only model as of July 2021, which meant closing our Atlanta site, setting up everyone to work from home, and granting WeWork memberships to each team member.

Some of the many benefits we’ve observed from remote work:

Flexible working: Not everyone enjoys or feels productive working in an office. Some hate having a commute, while others have small children, pets, or elderly family members to take care of. Working remotely provides space for flexible, asynchronous work so people can work in ways that fit with their schedules and personal priorities.

Wider access to talent: With remote work, you have more hiring freedoms. Rather than being limited to a specific region, you can find the best people across the nation. There is flexibility to expand your recruitment efforts and hire in more geographies, a benefit for both companies and job-seekers.

An equitable experience: With a company working fully remote, everyone has equal opportunity to contribute and collaborate. In this way, sometimes people feel more inspired to reach outside their comfort zones and raise their hand. Simply put, the playing field and opportunities to have impact are the same for everyone. This was the core principle our founder and CEO Tope Awotona challenged us to build our strategy around, and it is working really well.

Can you articulate for our readers what the five main challenges are regarding working remotely?

Creating immediate connection: Working remotely can be challenging for new team members. When you are onboarding, virtually meeting peers for the first time, and learning about the company’s set of processes and tools, it can be confusing and overwhelming. It’s also likely to take longer for those team members to feel comfortable with contributing or reaching out proactively with a question because they have to take extra initiative with little to no physical queues or context.

Maintaining connection: It can be much more difficult to create organic connections and build relationships when not in a physical office. People may feel less inclined to reach out to others outside their team and it can feel like technology becomes a replacement for a conversation.

Strategic alignment: Ensuring everyone at the organization has a shared understanding of the company’s mission, vision, and the path to success in a remote environment can prove tricky. In an office environment, there is typically a natural sense of physical community and an energy that binds everyone together to collaborate in pursuit of a common goal.

Continuous learning, development, and feedback: In a remote environment, you must be more intentional about being proactive and vocal when it comes to delivering or requesting feedback, recognizing successes or failure as teaching moments, or connecting people with growth opportunities.

Meeting fatigue: It’s no surprise we’re in more meetings than ever to make up for a lack of face time. People can become disengaged after being on camera so frequently on top of the pile of work they have waiting. To get a better grasp on this at Calendly, we created meeting best practices and instituted “core meeting hours”, or designated hours for internal meetings from 12–5pm ET, to help our people spread across multiple time zones set personal and professional boundaries.

Based on your experience, what can one do to address or redress each of those challenges? Can you give a story or example for each?

Roll out the virtual welcoming wagon: Everyone at the company has an opportunity to contribute to the experience new team members have in a remote setting. It almost levels the playing field when it comes to access and forming relationships. To help new team members feel connected at the start, send them a one-pager listing out all the tools the company uses, assign each new person a mentor or buddy as their go-to for any ad hoc questions and to enjoy lunch with their first week, and something we do at Calendly — establish cohorts of team members located in the same city to encourage them to meet up for social gatherings or shared days at their local WeWork. Ask new hires for feedback on the onboarding process after weeks one and four.

Carve out a place for relationships: Leaders and managers should put in additional time and effort into sustaining and building a remote-first company culture, otherwise your people won’t feel motivated about their work, their teams, or the company. Find ways to recreate the watercooler conversations to build in social interactions among teams. At Calendly, we use the Slack Donut app to randomly pair team members for a virtual coffee chat to get to know one another. The participation and response has been great. People seem to really enjoy it.

Overcommunicate and explore new channels for reaching your people: As a leader, ask yourself what you can do beyond holding virtual monthly all-hands meetings to convey company updates or strategic plans. While these are obvious company-wide moments for checking in and being transparent about the state of the business, it doesn’t make up for the lack of physical desk drive-bys or organic coffee chats in the hallways we once had. Think about the different channels and tools your people are already using to help with temperature checks and showing them how their work contributes to the organization’s greater success. We use Loom somewhat frequently to visually communicate company-wide updates, for leadership team intros, and more.

Be intentional: In a remote environment, you must be more intentional about being proactive and vocal when it comes to delivering or requesting feedback, recognizing successes, or helping people navigate career growth. This is what ultimately drives company innovation. It’s important to schedule recurring one-on-ones over Zoom, hold quarterly check-ins, and arrange project-based feedback cycles.

Take it offline: Think about ways to make meetings more engaging, whether it’s starting with a fun icebreaker question at the start of each one or taking the conversation off camera or Zoom. While we’re now a remote-first company and continue to have virtual all-hands meetings every month, we still believe that in-person interaction and relationship building is irreplaceable and vital to an organization’s success. In 2022 we will be adding two in-person all-company gatherings each year to come together for business and social activity.

Do you have any suggestions specifically for people who work at home? What are a few ways to be most productive when you work at home?

Set defined working hours: It can be easy to let home and work activities blend when working remote or on the hand, forgetting to unplug. Communicate and set boundaries based on what priorities you have at work and in your personal life, and stick with them. At Calendly, we have set 5 hours of the day as core hours. These are the only hours in which it is acceptable to schedule meetings. This allows our people to have dedicated time in their work day to recharge, work offline, or do other things as they see fit.

Have better meetings: Meetings aren’t necessarily bad, it’s that they’re broken. Have more productive meetings by always creating an agenda, clearly dictate the purpose of the meeting, and be clear on deliverables and action items following it. Platforms like Calendly were built to support this universal challenge we all face at work. Take advantage of some of the platform’s features like Buffers to avoid back-to-back meetings or Workflows to automate reminders and thank yous to attendees.

Take advantage of collaboration technologies: Consider interactive technologies like Loom for sharing updates or Slack for asynchronous communications. Our team created a designated Slack async emoji for our people to use when reaching out to a colleague with a non-urgent request that signifies it doesn’t need reading until the recipient’s morning.

Can you share any suggestions for teams who are used to working together on location but are forced to work remotely due to the pandemic? Are there potential obstacles one should avoid with a team that is just getting used to working remotely?

We talked about so many of those obstacles earlier in this conversion. Like any transition, moving from a shared location to a remote setting can be shocking. The biggest necessity for helping teams adapt is to remind them that they are not alone in this shift and that leaders, managers, and team members are here to act as a sounding board and resource along the way. We’re all still navigating what this new remote and hybrid environment looks like so patience, flexibility, and communication will be the best way forward for everyone.

What do you suggest can be done to create an empowering work culture and team culture with a team that is remote and not physically together?

Think about the organization as a living, breathing, dynamic organism made up of people, experiences, and its history and future. To drive a positive, empowering remote team culture, you have to think about how to influence people and create a high-touch environment. One way is to lean into your company’s values to drive a level of commitment and purpose among each individual to ultimately drive organizational performance. Another way is asking your people to share their voice. We have an internal engagement survey done in partnership with Glint to measure and improve engagement and overall company performance. The ultimate goal is to create a stronger organization. Finally, give your people the tools they need to drive the ultimate collaboration.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

I would love to reinvent our education system. It is too disconnected from the critical skills people need in life and in the workplace. For example, skills like budgeting, negotiation, time management, and how to work effectively in teams aren’t actively taught in education. These skills are essential for forming human connections in a world where we’re inundated by a plethora of technologies at our disposal. Author and TED Talk Speaker Simon Sinek has covered this issue masterfully. By reimagining the ways we educate people, not only will we help people increase their chances for achieving success in life, but we’ll also arm them with the raw skills and capabilities needed to thrive in the modern workplace so they can achieve their career aspirations. Organizations also benefit from having consistent access to a strong group of talent to achieve their bold missions. When I retire from CHRO work, this is the mission I plan to embark upon next.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

I am not a person who commonly refers to quotes, but there is one that always struck me by Rose Kennedy: “Life is not a matter of milestones, but memories.” It reminds me to focus on what truly matters in life and helps me find balance. I was a very goal-oriented, driven person at a young age who outlined a path with clear milestones identified. I had specific markers for measuring success for myself. For example, graduate college and buy my first house by age X, have kids by age Y, and achieve different career goals, such as becoming a CHRO, by age Z. This quote helped me realize that the things that fulfill me most are the little moments and interactions with other people. We need to cherish them, be present, and never take them for granted. Life is about the journey, not the destination. This perspective has enabled me to ensure I make time for my kids, my family, and my friends as opposed to getting lost in what can become an all-encompassing and lonely life as an executive if you aren’t mindful.

How can our readers further follow your work online?

Feel free to say hello at my LinkedIn at, or stay up to date with the latest Calendly news via our blog at

Thank you for these great insights! We wish you continued success.




In-depth Interviews with Authorities in Business, Pop Culture, Wellness, Social Impact, and Tech. We use interviews to draw out stories that are both empowering and actionable.

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David Liu

David Liu

David is the founder and CEO of Deltapath, a unified communications company that liberates organizations from the barriers of effective communication

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