Virtual Manager Series

Integrating Empathy Into Remote Management with Kelsey Mullaney

Kelsey Mullaney reminds us how critical it is to bring empathy into your management style - especially when working with a newly remote team.

Last updated on: 
August 11, 2023
The Pathlight Team
The Pathlight Team
June 22, 2020
6 min read
Integrating Empathy Into Remote Management with Kelsey Mullaney

The playbook for managing remote teams is rapidly evolving, and everyone is seeking the right tools to help them succeed. At Pathlight, we want to help every manager achieve their professional best, so we created the Virtual Manager Series.

In this series, we speak with real managers about their insights, tips, and tricks for successful management in this unprecedented time, so you can start implementing their best practices on your team tomorrow.

Introducing Kelsey Mullaney

Kelsey has been at Iterable since 2016. She joined the sales team when the company had less than 15 employees and now leads a full team of her own.

Keeping an eye on the numbers is important, but there is one key measure of success that can go overlooked in the new world of remote management — the well-being of employees. There are reps out there who are smashing their goals, out-performing their peers, and working harder than ever before… but are they happy?

A recent Gallup poll found that 15% of Americans believe that the coronavirus pandemic has had a “very negative effect” on their company/workplace. Another 56% said it had a “somewhat negative effect.” With 71% of Americans feeling worse off about their work situation, how can managers show up for their employees? Kelsey Mullaney has a few ideas.

Key Insights

Ask The Right Question

Mullaney says her number one struggle in adjusting to remote management has been gauging the actual emotions of her reps. Given that challenge, she has committed to never skipping one question during her one-on-ones. “I try to ask, ‘How are you actually doing?’ because it is so easy to put on a smile during a Zoom call,” Mullaney says.

“I try to ask, ‘How are you actually doing?’ because it is so easy to put on a smile during a Zoom call.”

Without offices and in-person interactions it can be easy to miss emotional cues. Mullaney believes it comes down to simply taking the time. “I designate ten minutes of every one-on-one to talk about how they’re actually doing,” she says. By creating the space for honest conversations, Mullaney can genuinely connect with her reps beyond work-related matters.

She says she learned the value of caring about her employees lives outside of work from her former manager. “He cared most about my happiness, which bleeds over into everything else.” Now, more than ever, the support that she offers her team goes beyond helping them make sales. “My goal is always to enable, empower, and grow the people I manage,” she says.

Redefine Winning (and Losing!)

Since her company began working from home, Mullaney says she has put a large focus on shifting how members of her team define “wins”, something her current manager, George Cerny, has been inspiring to do. She tells her reps, “The truth is — numbers look different right now. What are you going to be proud of?” It is important for sales orgs to adjust their mindset when the economy has drastically changed. Mullaney says that redefining what a win looks like helps her team stay motivated, and frankly, sane.

“The more comfortable your team feels with failing in front of you, the quicker they can improve.”

Mullaney takes an empathetic approach and says it’s crucial to always create an environment that promotes psychological safety. “The more comfortable your team feels with failing in front of you, the quicker they can improve,” Mullaney says. “If you do that right, things are much more efficient and the path to achieving goals can appear closer.”

Casual Connection

Mullaney’s team is super social and loves building relationships, but the lack of shared physical space has led to less social interaction and has impacted employee satisfaction. Mullaney says, “They miss that casual banter. So I asked myself, ‘How can I accommodate?” She answered the call by implementing a daily standup with her team that features a “temperature check question” to encourage everyone to share how they are feeling that day. “[It] has become a huge value add,” she says.

Standup also presents an opportunity for the banter that employees are craving. Mullaney throws in questions like, “If you could have coffee with anyone, dead or alive, who would it be?” The daily question is fun, light-hearted and creates space to form connections. Mullaney says. “It’s about the little things that take it beyond work to connect with people on that emotional level.”


Similar to her commitment to being there for her reps, Mullaney has also doubled down on her commitment to self-care. “When things get busy, block off calendar times for a ‘you break’ and force yourself to walk outside, listen to music or a podcast,” Mullaney says. She believes it is important, and actually better for long-term productivity, to respect when the work day and work week end.

“I schedule things in order to encourage myself to sign off. I also tell my reps I won’t be available so they know.”

This has become a bigger challenge now that the line between work and home is so blurred. For managers, it is especially hard to let go of being on top of everything. “I had to learn to allow myself to leave things at work,” Mullaney says. “The biggest challenge is struggling to turn it all off and not having everything blend over into one.” In order to prevent that burnout, Mullaney says, “I schedule things in order to encourage myself to sign off. I also tell my reps I won’t be available so they know.”

Tips and Tricks

What helps your team stay focused on their priorities?

“Every Monday we have a team meeting where each member of the team talks through their goals for the week. I write it down, and then I pin it in Slack as a reminder. Then we go back on Friday and we review how we did on our goals. If they did accomplish their goals I’ll ask ‘How did you get there? What can others learn from that?’ and if they didn’t accomplisht it I’ll ask, “What can we do next week to support you?’ I think it’s helpful to define the goals for the week and break it into smaller pieces, rather than for the whole quarter. Of course, we have our pipeline meetings and things like that, but I find that individualizing things holds people more accountable.”

How do you let your reps know you’re available to help?

“I do weekly office hours that are open to any rep in the sales org who wants to come and ask strategy questions.”

What is your formula for an effective 1:1?

“1:1s are always meant for the people I manage — whatever they need, we chat through it. In order to make it as effective as possible, I have a shared Google Doc where my reps fill out an agenda prior to the meeting so I can properly prep anything they need before. I designate ten minutes of every 1:1 to talk about how they are actually doing, and I always end them with asking what else they need from me, making sure they know I’m accessible and there to help.”

“Always create an environment that promotes psychological safety.”

What’s a mistake you made when you first started managing?

“I had to learn to overcome imposter syndrome. When I first started managing, I struggled with being myself and not trying to be someone I wasn’t. You have to remember you’re there for a reason.”

What’s the best advice you’ve ever received on managing a team?

“Always create an environment that promotes psychological safety — the more comfortable your team feels with failing in front of you the quicker they can improve and the path to growing is faster.”

Rapid Fire

One quality that every manager needs to develop?


What is a manager’s spirit animal?

Alpha of the wolfpack.

When you were an individual contributor, who is the best manager you’ve ever had and why?

“My previous manager Ian Brandon — I really enjoyed him as a leader, simply because he did a fantastic job empowering me and allowing me to make my own mistakes and learn from them.”

If you had to wear the same t-shirt for a year and had to choose a quote to put on it, what would it be?

“‘It’s All Good.’ It’s something my dad would always say to me when things would get hard. It’s a good reminder to take a step back and look at the bigger picture.”

Thank you to Kelsey for sharing her invaluable insights. If you’re looking for ways to manage your team effectively in this new environment, check out the other interviews in our Virtual Manager Series or try the Pathlight platform for free.

Want to see a custom demo of Pathlight or get help finding the right plan? We'd love to chat.

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