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Remote Career Development: McKenna Sweazey Of Marketing Truthset On How To Advance and Enhance Your Career When You Are Working Remotely

An Interview With David Liu

Connection. In a remote workspace, strengthening the bonds between people is inherently more complex. But this is where the fun comes in! Creating a calendar of team-building activities that work for developing emotional intimacy and interjecting fun into work lives is critical. You want a variety of activities, some mandatory, some not, to meet people’s differing social needs. Educational activities, like public speaking training, should be mixed with more “exciting” activities, like an at-home cocktail-making class.

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 McKenna Sweazey.

McKenna Sweazey is a remote and hybrid management author and coach. She has spent years working in global organizations, from corporates to start-ups, managing remote teams around the world and is currently the VP of marketing at a tech start-up. McKenna has spent her career refining her management skills to be as effective in person as from 6,000 miles away. Her passion is helping people harness empathy to better connect with their colleagues to drive 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 getting my MBA at INSEAD, I went to work for a rapidly growing tech start-up with offices around the world. While I was based in London, I was working with and managing people around the globe. This gave me my first taste of building connections primarily using the digital tools at our disposal, mostly Skype chat and phone at the time! Subsequent roles had me managing larger global teams, and that’s when I doubled down on a framework for being a great remote manager.

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

In my first job out of business school, I saw my manager just once in my first year. I hadn’t really thought about this when I took the position. Aside from my interview before getting hired, we just had one twenty-four-hour business trip at the same time in New York together in my first 12 months on the job. That was it for me to get an idea of who this man was, what he wanted, and how I was supposed to help him. In a fast-paced start-up, there wasn’t much time for coaching or formal learning; we had things to do!

Thankfully, it’s my nature to try to read people, and I paid careful attention on that trip, knowing that my success at the company depended on our relationship. Later, in our primarily digital relationship, I kept paying attention: I parsed tone in emails. Read body language from video streams of conference rooms. Gleaned insights from other coworkers into his behavior. If he reads this, he’ll probably also note that I made liberal, possibly TOO liberal, use of emojis in our frequent Skype chats.

But it worked. Over our time together, we forged a strong, warm bond, where I knew what he wanted and why, often before he said it. This surprisingly effective but mostly remote relationship made me realize what it took to form strong digital bonds. This experience laid the foundation for my book, How To Win Friends and Influence People Remotely.

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?

I was in my first email marketing role, and I was about to send a major update to all of our clients and partners. In a classic global organization fashion, the way teams around the world used the CRM was different, so that some people’s personal contacts were also included on our list to be emailed. Including people’s moms and dentists would’ve been a funny blooper if I hadn’t made a tiny mistake in the code to send the email seven times overnight to everyone. Funny in retrospect, absolutely terrifying at the time.

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

Jump and the net will appear. I love this idea, having faith that everything will work out. In reality, this is so not me. I’m a worrier, an over-planner, who has a spreadsheet for everything. I definitely have to be reminded to have faith in the universe and to believe things will work out, so the idea has stuck with me.

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

Check in systematically. It’s great when we know our team so well we can tell that something is up in their personal life just by a change in their apparel or voice tone on a video call. But not everyone can harness their empathy skills to pick up those changes. Great managers need to be systematic about checking in with their employees’ mental health. This can be as simple as a monthly reminder: have you asked everyone on your team how they REALLY are this month? Some people won’t be able to articulate if they are heading towards burnout, but creating a repeating moment to think about where they are and what they need gives you both the opportunity to catch negative trends and avoid the consequences.

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 opportunities 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?

For me, there are two key benefits to remote work, flexibility and diversity. Flexibility is clear. Workers don’t need to be tied to a strict 9 to 5 day to get great work done. This new schedule allows for so many benefits. I love the idea that we can work to our natural rhythms, with night owls typing away furiously at 10 pm or mothers of young children working during school hours. Remote work can also lead to diversity. Without being tied geographically or temporally to a traditional office setup, we can open our pool of possible candidates for any role. Diverse candidates, who might not have been eligible for a position previously, can now bring their unique talents and perspectives to companies.

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

Knowledge distribution. Without watercooler moments, full team in-person meetings, and passive information transition in an open-plan office, it can be hard to ensure that knowledge flows in the most comprehensive way around an organization.

Synchronicity. The downside of flexibility is that people are online at all different times, making communication occasionally stilted or hampered.

Boundaries. Without a way to “leave” the office at the end of the day, many employees find it hard to keep their work commitments from bleeding into their personal time. For those working flexible hours, how much work is enough work?

Communication. Building authentic relationships with coworkers makes it easier to communicate and achieve goals. These authentic connections take more effort to build virtually. If you don’t feel safe or trusting in your work environment, you aren’t as emotionally generous with communication. Assumptions are made, negative emotions are presumed, and people rely on stereotypes instead of getting to know each other.

Connection. While some people love the efficiency of working from home, many others find it lonely to only chat with colleagues sporadically and virtually. It’s harder to build friendships, to share hardships, and to feel a human connection if all of your interaction is through a screen.

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?

Knowledge distribution. Create a framework for the team’s communications that allows respectful, open, and comprehensive communications. Consider all your mediums for distributing knowledge, from the asynchronous, like email, to the synchronous, like meetings, and give your team a guide to the primary use case and expected behavior for each. Maybe meetings are only for large debates and Slack is for all weekly updates. Or maybe you want to have meetings for all monthly updates. Each organization is different. But defining your use cases should give you an idea of what tools you have and what tools you need to transmit and store information that needs to be accessed by everyone. The pandemic has driven amazing innovations in remote work tools, for creativity, for knowledge distribution, and for communication. Being clear about expectations and etiquette makes it easy for colleagues to communicate as seamlessly as possible.

Synchronicity. Using cognitive empathy can help, trying to think about the recipients’ reaction to your messages. What do they need to do their work without coming back with questions? All communications should be comprehensive enough that others can work off them without needing additional back and forth. It’s also useful for many teams to have core working hours or days to make it easier to have synchronous communications. For asynchronous communications, being explicit about expected response times can take away some of the frustrations of asynchronous communications.

Boundaries. Managers should set a good example for starting and ending the workday in a committed fashion. They should be reminding their teams that rest and fun outside of the workday are critical to bringing your best self to your career. Having core working hours can also help set expectations for when turnaround times should be quick and when they can be a little slower, e.g., weekends.

Communication. People who feel safe and trusting within their work environment approach communication in a positive way, assuming the best in their colleagues and helping to translate their meaning via virtual channels to meet others needs. Knowing your coworkers comes from seeing them in different scenarios and understanding their various reactions, so you can feel comfortable with how they will react in the future. Team building activities are a great place to start to build more intimate connections with people so their communications can flow more effectively. You want activities that show off different aspects of colleagues’ personalities, so some competitive, like a virtual escape room, some creative, like an at-home art class, and some emotional, like a Life Mapping exercise, create a mix of scenarios that lead to real understanding between colleagues.

Connection. In a remote workspace, strengthening the bonds between people is inherently more complex. But this is where the fun comes in! Creating a calendar of team-building activities that work for developing emotional intimacy and interjecting fun into work lives is critical. You want a variety of activities, some mandatory, some not, to meet people’s differing social needs. Educational activities, like public speaking training, should be mixed with more “exciting” activities, like an at-home cocktail-making class.

Let’s talk about Career Development. Can you share a few ideas about how you can nurture and advance your career when you are working from home and away from other colleagues?

Everyone needs to be more explicit in a remote workforce. For career development, that means discussing your ambitions with your manager and making a concrete plan with them for how you can achieve the necessary goals to get there. It also means making sure your accomplishments are known. It’s a fine line between over-sharing, which can be seen as bragging, and sharing valuable updates that others across your organization will be interested in. But it’s a good rule of thumb that if you want to get ahead, the projects you should be most proud of should also be those others are most interested in as well. Lastly, remote work has broken down all of these barriers, meaning you can easily reach out to others in your organization or outside of it to hear more about career progression or different roles. Don’t be afraid to get in touch with people whose experience you admire; you never know what pearls of wisdom they might have or possible introductions they might make.

Can you share a few ideas about how employers or managers can help their team with career development?

The most important thing a manager can do is be transparent about goals, from the company’s perspective, the team’s, and the individual’s. Spelling out what success looks like and how everyone in your organization can concretely contribute to this success is critical in remote management. Because you don’t get as much passive information transfer, active information transfer, such as transparent OKRs (Objectives and Key Results) or KPIs (Key Performance Indicators), give your direct reports a north star to follow when they are working alone in their home.

As a manager, you should also acknowledge that your team will grow and move on. That’s a sign of a good manager, that you are growing your team. Don’t be afraid of those discussions, be excited for them. The more transparency you have, the easier it is to hang on to their talents, either in a progression of their current role or in a new one within your organization.

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 wish all schools and employers would teach cognitive empathy and how to improve it. Studies show our ability to understand each other’s emotions and perspectives is malleable. Acting classes, reading fiction, taking time out from social media, all of these actions are proven to improve your ability to understand your fellow humans. If we were all just a little more able to take each other’s perspectives, imagine the pain we could avoid and the amazing things we could build.

How can our readers further follow your work online?

Check out my blog at

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



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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