Julie Remington Of R+R Learning: 5 Ways Empathy Will Affect Your Leadership

Thank you so much for joining us in this interview series. Before we dive into our discussion about empathy, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?

I found my career path after journeying through life with a profound resistance to any career path. 😉 I remember hearing “she’ll be a music teacher” before I even really knew the meaning of career path. When I graduated from high school, my rebellious pride boasted, “I’m going to be an aerospace engineer” to each person that predicted I’d be a music teacher. After a little zigzagging in college, I graduated with technical experience in the aerospace field and a math degree. That’s when I heard those rumblings again, but this time they said “…but don’t you want to be a math teacher?” My inner rebel continued to resist, but with more bills to pay, when I couldn’t find a job in actuarial science, I resigned to teach Math at a High School in Hawaii. For paradise, I would compromise.

I learned a lot during that time and had to super-speed-up my own leadership development to keep up with the many needs of the school and students. Although I knew public school teaching was not a good fit for me, I became curious about the business of education. This curiosity gracefully carried me to work in Test Prep and then Executive Education. This is when I realized my passion for facilitating adult learning. I noticed myself geeking out regularly as I watched people of all ages have light bulb moments and celebrate learning milestones in social adult learning environments.

From there, I jumped in feet first and started Learning & Development departments in two hyper-growth tech companies. Then I established R+R Learning to focus on reimagining work using tools that guide us toward a sustainable and successful balance. It’s a pleasure to find a career path that allows me to lean into the parts of Leadership & Learning Development that fuel my passion to improve workplace cultures by empowering people to acquire new skills, embrace change, and thrive in individually unique ways, together. I’m extremely thankful to the wandering road that brought me to this career path.

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

I think the most interesting part of my career is zooming out for a 30,000 ft view. I have the privilege of working with a lot of people. I hear a lot of stories. I talk with people about their styles, behaviors, conflicts, and values. We conversationally explore perspectives and ideas, then apply concepts to the world around us with the goal of finding ways to influence a better energetic balance for sustaining work, health, fun, family/friends, spirituality, and community contribution.

After working with 1200+ people, it’s strengthened my perspective of people in a few key ways.

• People intend well. Good intentions don’t always translate to positive impacts. Discuss intentions and impacts to discover where they did or did not align, like mini retrospectives. Try it out the next time you’re not sure how something landed.
• Conflict has an undeserved negative reputation. People who embrace healthy conflict fuel positive momentum while reducing stress.
• Like good recipes — discovering the various energetic formulas that support your humanity, values, and biology best is priceless. Get to know yourself as a changing being who thrives under certain conditions — not all conditions.
• It’s better to experiment, not to compare. For example, in comparison we may notice a desire for a trait someone else has and demonstrates well. Ask yourself, “What’s at the root of what I like about this idea/trait? How can I experiment with that idea/trait in my life?” You can think of it like a scientific experiment or a detailed clothes fitting. Is that my color? Tweak it so it is the color that compliments you best. What does that look like? Is it the best shape for me? Tweak it until it fits. Until you’ve figured out what about it works well for you and the way you want to show-up in the world.
• Practice out loud. No one can see through your eyes, to truly see your perspective, except you. The more you communicate clearly about the conditions that support you in staying out of stress, the more the world around you will meet your needs. Find ways to share what you’re learning along the way with teammates and people who are there to support you.

What do you think makes your company stand out? Can you share a story?

R+R Learning stands out because its goal is to reimagine work as a more balanced and sustainable part of our lives. It’s easy to default to traditional systems and company cultures that reward burnout. It’s difficult to tell your over-worked boss that you’re not interested in keeping the hyper-pace and would like to consider an alternative schedule that will allow you to show up at your best to work in the future. This is the gap that R+R Learning’s tools help people to bridge.

Imagine someone who experiments to find they thrive in environments that support expressiveness (a.k.a. communication), but they’re on a team where communication is sparse and expressing enthusiasm or frustration openly is perceived as a waste of time. This person may realize the discouragement they’re feeling isn’t a reflection of the work they’re doing, but rather stems from the fact they’re not getting much communication, feedback, or retrospective time with the team. Everyone’s pressed for time and adding meetings is frowned upon. Where does this person go from here?

I’ve worked with clients that bridged a gap similar to this — each in a way unique to their own needs, goals, and team values. One person who sat in a role of influence without authority, chose to take ~6 months to thoughtfully develop and roll out a new process that allowed their team to document communication clearly for one another in centralized asynchronous ways throughout a project. This allowed for less team meetings during a project cycle. Allowing for more focused work time it also opened up an opportunity for pre and post meetings to be added where everyone could practice sharing communication, feedback, and resetting before moving into the next project. Ultimately, they shifted the points and style of communication to be more efficient and effective overall. Through thoughtful process design, this client’s hard work and strength in seeing the importance of communication to team morale and success, helped the team to find a balance that worked well for their unique mix of direct and contextual communicators. It’s worth noting the client also spent a good month or more socializing the idea with the team, tweaking things for better alignment and growth opportunities in the team.

The joy of watching clients go from a place of discouragement to a place of empowerment and joy, while rippling it through their team makes me so thankful to be doing the R+R Learning work.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

Thank you for the compliment. It’s important to me to respect the fact that I cannot see through anyone else’s eyes but my own, especially as a leader. Therefore, the 3 traits I find myself using most as the leader I choose to be, include courage, care, and open-mindedness. These traits are extremely supportive of the work I do every day with people, personalities, behaviors, and relationships. I apply these traits to 1-on-1 coaching sessions and to working in teams and groups.

Let’s keep in mind, I’m not an expert on you — even if I have your personality assessment, answers to a handful of questions, and a slew of experience with other people you know — so I lean on courage to show up with curiosity, instead of answers. I lean on courage to say the hard things when no one else will, but without diminishing a person’s own position as expert of themself. I lean on courage to get up in front of groups and facilitate conversations that people carry away with them.

I genuinely care about the human experience, so I care that people are cared for and about. Whether it’s the random person I’m chatting with or a long-time coworker or client, I stop, focus, and actively listen. Honestly, I can’t help myself. I want to honor that I can’t know someone’s entire perspective of everything, so I enjoy slowing down to listen. It’s like reading a chapter of an autobiography, but with the opportunity to ask questions and say, “Is this what you mean by that?”

I turn to open-mindedness to receive what the person is saying and talk about it without judgement. Since I believe you are the expert on you, I don’t want to let my perspectives and experiences get in the way of you figuring out something amazing that works for you and your life. I’ve had to learn to be comfortable with discomfort at times to stay open-minded as someone who works with teams and communication. The more I invite everyone’s perspectives into a conversation, the more successful it ends up being, even if it gets a little uncomfortable here and there.

Leadership often entails making difficult decisions or hard choices between two apparently good paths. Can you share a story with us about a hard decision or choice you had to make as a leader? I’m curious to understand how these challenges have shaped your leadership.

When making difficult decisions between two apparently good paths, the tool I turn to most is Brené Brown’s 5C’s, from Dare to Lead™.

Not long ago, I had a difficult partnership decision to make. I was doing some workshops with an extremely talented colleague with a — more often than not — abrasive personality. I was super inspired by the work and the progress the participants were experiencing due to our collaboration. The money was sufficient, but the work could be energetically draining, so when partnership was proposed, I had a lot to think about. Choosing the partnership could benefit me by giving me more opportunities to become an expert in the specific content area, but not choosing it could allow me to take what I learned from the experience and apply it to other industries, audiences, or tools.

It was a big decision for me at the time, so I set aside an hour and gave myself some space to sit with a blank pad of paper, a pen, and Brené’s 5C’s: Color, Context, Connective Tissue, Cost, and Consequences.

Working with the tool helped me understand the partnership would bring me $1,000 less than my monthly goal and would energetically inhibit me from making up that cash in another area. It allowed me to go back to negotiate with clarity, kindness, and true understanding of my own perspective. I ended up choosing not to partner and instead experienced the opportunity to broaden my experience in a handful of similar, but different areas of work.

I’m extremely grateful for these kinds of challenging choices and for tools like Brené’s 5C’s to help me think it through. This kind of process allows me to recommit to my own energetic balance while finding better ways to communicate my values, goals, and boundaries.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. Let’s begin with a basic definition so that all of us are on the same page. How do you define empathy in a leadership context, and why do you believe it’s a vital trait for leaders to possess in today’s work environment?

I define empathy in leadership as the use of feeling in leadership. Since feelings signal the subjective world to me, let’s change the word feeling to the idea of the subjective realms of life. Subjective things are based on personal perspectives and preferences of a person. The definition becomes, the use of subjectivity in leadership. Now this gives us something to dig into!

Leaders need to be able to navigate from logic to feelings as it relates to the work, the employees, and the team/company culture. Leaning into subjective leadership allows for perspective taking and compassion — the feels. Leaning into objective leadership allows for decisive actions and practical results — the thinks. Every team is made up of a mix of styles and perspectives, so the more readily the leader addresses the entire spectrum from logic to feelings, objective to subjective in the team, the more they’ll be understood, trusted, and make progress as a team.

I believe it’s vital for leaders to cultivate a balance of subjective and objective leadership practices. Although, of the two styles, I also believe subjective or empathetic leadership practices have been the underdog for a while. It’s much easier to reward and uplift the objective things — we made the money, we solved the problem, we did the thing — especially in teams and groups. It’s much harder to reward and uplift subjective things. How would these statements fly in your organization? We really made the client feel heard. We shared our feelings openly and honestly with leadership. That imaginative approach really worked!

What’s your default leadership style — subjective or objective? A quick way to assess this is to consider what phrase you default to saying more often, “I think” or “I feel.”

I encourage teams to discover their default styles by using this simple observer game. It’s worth noting that default styles aren’t the whole story. I think of my default styles as the behaviors I go to when I’m not investing any energy or attention in them. When I’m not thinking about it — how do I show up? That’s a default style, IMO.

It goes like this:

• Set a week timeframe and use the time to observe who says, “I think” vs. “I feel” in your team or group.
• Keep a casual tally as you navigate through team meetings and daily tasks. Written and spoken words count. If you miss a couple — it’s no big deal. This is meant to be light and fun.
• Then host a team meeting after the observation time is over and ask the team:
• What did you observe about one another?
• Do we show up more objective or subjective, based on the results of the observations?
• Then have each individual answer:
• Where do you think/feel your strengths come from: the objective or subjective realm? How do you apply your strengths to the work? team? project? etc.
• Thank the person for sharing, then go on to the next person until everyone has shared their perspective.

The people who say “I think” more often will likely show up as more practical and eager to solve problems. These folks are likely the objective leaders in the team. They use facts, tangible elements, and emphasize action over thought. Objective Leadership strengths include giving practical answers, staying objective and detached, controlling their emotion, and being open to competition (w/objective rules, of course).

The leaders who say, “I feel” more often are likely the more empathetic leaders. They show up as leaders that are easy to confide in, who explore options thoroughly, and actively pursue new ideas and information. Subjective Leadership strengths include listening without offering answers, initiating subjective conversations, visualizing the completion before the beginning, and setting high expectations.

Some people will show-up more 50/50 — half the time they say, “I think” and half the time they say, “I feel.” These folks will likely bridge the gap in the team between the two perspectives. They’ll show up as empathetic or objective leaders under certain conditions. Think of them as people who walk ideas across a bridge of understanding, translating between “I think” and “I feel” statements. Often times these folks make great people leaders because they are aware of the two sides of this spectrum and how they can be used in compliment.

Can you share a personal experience where showing empathy as a leader significantly impacted a situation or relationship in your organization?

Well, since I work with people to uncover what’s not working and figure out what works better, I’ve always been a little bit more prone to lean towards empathy in my leadership of others. I show up for others with a suggestive style that allows people to play in their own perspective of things and choose their own path. So, the personal experience where showing empathy had a significant impact in my organization, was actually when I started using it in my self-leadership.

My self-leadership style leaned heavily towards command-and-control for a long time. The extreme self-pressure worked well enough for me, until it didn’t. I found myself giving others a lot of space to make mistakes, pause to reflect, and figure out what was worth learning at the moment, but not doing the same for myself, I knew it was time to revisit my approach. I observed myself to start and the wicked self-talk that occurred when I did the most minute things, was intolerable now that I was paying attention. Ugh. For example, I made an unrealistically long to-do list — everyday — and then didn’t accomplish it and would beat myself up for it until I’d do it again, the next day. If I was coaching someone with this behavior, we’d be working on understanding task time and being realistic about the energy we’re working with under certain conditions. Then we’d work on what that means about boundaries and having the ability to show-up for the time you do have to dedicate to your tasks and priorities.

It took a very challenging coaching conversation one day, after which I was reflecting on the conversation, sending love to the client for the difficult time they were going through and my inner voice started to bark orders about how I screwed it all up and could’ve done better had I just… fill in the blanks with all the “in an ideal world” things. And — thank goodness — it finally hit me! Why am I talking to myself like this? Even the most difficult coaching conversations I’ve had have been open, warm, and accepting without the need to bark orders or put tight controls in place. And I had the proof of having heard it from each source, that all of those conversations resulted in something positive. I had complete faith that my client would later find this bump in the road to be a diamond in the ruff of their career journey, as they did. I had the proof it worked and it still took me a while to realize I could apply it to myself. Doh.

I chose to intentionally start moving my self-leadership style from command-and-control toward empathy. I started by becoming a keen observer of my evil-twin-inner-voice. I found it popped up at the most ridiculous times. I observed that when I was most non-empathetic to myself was when I assumed I had control over something but didn’t in reality.

I started with the low-hanging-fruit, my to-do list, and the daily self-trauma I was causing due to my mismanagement and control issues with time. Instead of a daily to-do list, I started keeping a Big List of Ideas. It acts as a parking lot of tasks and ideas. I pick from the Big List to fill in time blocks in my calendar as I plan ahead. Not only can I better assess how much task time is in a day, but I find I’m forced to ask myself, how much time do I need to complete this to my satisfaction in one-sitting? “To my satisfaction.” That’s the empathetic/subjective part. Although my old command-and-control guard wants to jump in and say, “You’ve got to get it done in [some absurdly small amount of time] or you have no business running a business!”

At first, I had to be very deliberate about the mental leadership adjustment. Once I was able to suspend the self-judgement (sometimes it took a short walk outside or change of scenery), I let myself dream of an ideal world and asked, “In an ideal world, how much time would you spend doing this task?” I’d breathe deeply, staying focused on the question until a time frame bubbled up with a clear outcome. Most of the tasks in my list are stacked with a bunch of sub-task assumptions. My thinking would generally go something like this, “Draft the next online mini course you’ll publish. 8 hours would be ideal to draft the entire course, without recording.” When my window of opportunity was only 2 hours, but my ideal was 8 hours, I needed to suspend any judgement about that and ask, “Well, what can you get done in 2 hours? ¼ of the thing, so what’s that look like?” Once I got in the habit of doing my week-ahead design with more empathy, I saw one more area I could really infuse some more empathy. Now I also ask myself, “And what happens if you don’t get it done today? Any array of things could side-track you or need your attention, so how will you be kind to yourself if/when that happens?”

It’s like swapping between languages. I wanted to spell out my inner conversation in detail for anyone getting started on this journey of empathetic leadership. I’m a fan of sharing what I’m learning with people, so I also enlisted help of family and friends when I felt comfortable. The more you practice traversing styles and talking about it with others, the easier it becomes, and the more opportunities will arise for practicing.

When I started out on this development path to be a more empathetic self-leader, I did it thinking of me, not necessarily of its impact on others. I used others as my inspiration, but I was self-focused in where I was looking for improvements and benefits. Happily, it also ended up improving my relationships too! Without the hidden guilt and shame that was undoubtedly an undertone for me before, now I set boundaries confidently based on my priorities, timelines, and energetics. I could see people responding more positively than ever now that I can communicate these ideas with confidence and belief in myself! Whether you’re on a path to more empathetic self or other leadership it will inevitably have a positive ripple effect.

How do empathetic leaders strike a balance between understanding their team’s feelings and making tough decisions that might not be universally popular?

Lots of listening, learning together, and communication.

The wild thing about the subjective realm, is that sometimes all that’s needed is active listening. Get in the habit of acknowledging someone’s feelings by repeating back what you heard in your own words and asking the person if you understood correctly. It’s easy for someone who defaults to a more objective set of styles to think they need to do something to solve for the feeling, but that’s not what the subjective realm wants or needs. The subject realm is about expressing and being heard. The objective realm is about solving problems and doing things. The skill to hone here is the way you listen and repeat back to verify your understanding. Use this skill to actively listen to your team’s feelings, repeat back, and build trust.

I also suggest leaders really get to know themselves and their teams to find a good balance. I use an assessment and variety of activities and workshops with teams to help them get a deeper understanding of the makeup of their team’s behaviors and styles and how they individually fit into the tapestry that makes the magic happen. I find the more we normalize and develop a common language around these types of conversations in the workplace, the easier it is for people to bridge perspective and communication gaps without conflict.

You’ve heard this one before — leaders need to repeat, repeat, repeat what you’re saying until just a little past the time you’re extremely sick of hearing yourself say the same thing. You can also diversify your communication, so it’s hitting a variety of comprehension styles in the team. Likely, you’ll have some folks who will find written communication easier to digest, others will want to hear you say it out loud and be able to ask you questions, and others will respond best when something is phrased a certain way. I use a who, what, why, where/when tool to help work with teams to think through the various perspectives they need to address in communication and how they’ll repeat, repeat, repeat with ease.

I think a difficult part to bridging perspectives and decision making is accepting that there will never be a static set of rules or ways that makes your message hit every time. People are constantly changing and growing along with the work, so there can be a feeling that as soon as you figure out a listening, learning, communication style that works, building trust and compassion amongst the team, you might have to tweak it in the future, depending on the variables at play. Extract learning out of each experience, and you’ll be on the path to figuring out what works best for you and your team in all of those situations.

How would you differentiate between empathy and sympathy in leadership? Why is it important for leaders to distinguish between the two?

Empathy involves relating to what a person is feeling. Although I didn’t have the exact experience you did, I can relate to the feeling of stress, regret, or invisibility (as examples), because I felt it before in myself. So, when we’re doing empathy well, there will be a stronger connection because the person was able to be present for you and your pain (or vice versa) — without judgement or trying to fix it.

Sympathy is offering words of comfort. It’s used at an arms distance. Unlike empathy, which requires feeling together, sympathy does not. It takes a distant look at the feeling and finds words to convey a message of comfort. Done and said.

Empathy lingers. It has to because if you’re going to honestly connect with the feeling, it’s not going to be instantaneous. It may require you to go from your logical mind, into your subjective mind. From head to heart. If only for a few seconds, it must linger to allow for connecting to your feeling self so that you can be present for the person and what they’re feeling.

Empathy is a great inclusivity tool because it honors each of us are having our own experiences — you walk in your shoes and I’ll walk in mine, but we can certainly relate to a feeling. You be the expert on you, and I’ll be the expert on me, and we’ll connect over the emotional experience of being human.

What are some practical strategies or exercises that leaders can employ to cultivate and enhance their empathetic skills?

I highly suggest turning inward first and foremost. Really get to know your default styles, the energetic balance that allows you to show up empathetically and build the muscles that help you become more and more comfortable addressing things in thinking and feeling ways, even if its uncomfortable.

Practice by:

• Listening without offering answers — Cultivate a go-to list of open-ended questions and get comfortable with silence, even if the other person isn’t talking, if you wait long enough, they will. Practice non-judgement and listening to a story that doesn’t match your experiences and believing it anyway.
• Expressing your feelings — How we express our feelings can be as unique as we are. Do you express your feelings easily? Do you express your feelings often or not at all? What’s an appropriate balance? Do you have vocabulary that stretches beyond glad and sad to describe your feelings?
• Connecting with values — What parts of your team/company values address the subjective v. objective? How can you give attention to the subjective parts as much as the objective? How can values help you identify what subjective wins could be celebrated?

Experiment with these ideas IRL and reflect on your experiences w/a mentor or coach using the below questions:

• How does my approach help me?
• How may my approach be interpreted by others?
• How can I manage misinterpretations?
• How may my approach limit me?
• How is my approach helping me to get the results I want?
• How is my approach not helping me get the results you want?

How can empathy help leaders navigate the complexities of leading diverse teams and ensure inclusivity?

Ya know, I’ve never heard anyone say, that leader is WAY too empathetic. Have you? Food for thought, but back to the topic, if you want to ensure inclusivity, empathy is a good thing. It honors the subjective realm — the realm of perspectives, feelings, and expression. And what does a diverse team have in bulk? A variety of perspectives, feelings, and ways of expressing. Using empathetic leadership skills allows the diversity of perspectives and expressions to coexist inclusively while connecting to a shared purpose.