If you’ve made it this far into 2020 with your business intact, congratulations. There’s maybe never been a harder time in modern history to run a company than right now.
Between environmental disasters, civil and political unrest, the COVID-19 pandemic, the economic fallout of said pandemic, and more, there’s a lot going on at the moment—and few opportunities to disconnect from it all. Not when millions of us are still stuck at home.
How is an organizational leader supposed to manage it all? How do you make sure your employees feel motivated, connected to each other, and aligned with your values in these—ahem—unprecedented times?
To find out, we spoke to one of our very own executives: Rebecca Grimes, Ruby’s Chief Marketing Officer.
Rebecca is our resident expert in building and leading teams. She’s successfully navigated and grown organizations throughout periods of change and uncertainty, keeping people connected across functional, business, and geographic boundaries. She does it all with a human-first approach, a perspective rooted in small business, and an unwavering commitment to give back and serve the community.
We spoke to Rebecca about being an executive in the COVID era, how she’s keeping Ruby’s team together across distances, what it means to lead with vulnerability, her preferred caffeine delivery method, and more.
This interview has been edited for clarity.
RUBY: How have you kept Ruby’s employees engaged and connected throughout the various crises and disruptions we’ve seen in 2020?
REBECCA: At Ruby, our leadership team believes in leading with vulnerability. We want our message and tone to match where our people are in their lives—what they’re feeling and dealing with right now. That means we need to communicate frequently and authentically.
Communication is all about active listening. I mean, just a question like “How are you doing today?” has become really loaded. Instead of shying away from it, we actively listen and let the conversation go sideways if it needs to. We then act on what we learn. We want to hear what people are actually thinking and going through, and take whatever opportunity we can to make their lives easier.
For example, during the recent wildfires on the West Coast, we did a pulse check. We asked people if there was anything they needed, any way we could help. One team member remarked that she was immunocompromised and half-jokingly mourned that with the pandemic and smoke, she didn’t know when she would have a chance to leave the house and get coffee again—she had just put her last Nespresso cup in the coffee maker. We figured out a way to get coffee to her house.
Earlier in the year, when people were hoarding things like toilet paper, another one of our employees mentioned he was having trouble finding basic essentials, so we made sure to get him what he needed to reduce his anxiety. These aren’t things I thought I’d be doing a year ago, but that’s life right now. We’ve adapted in order to take care of our people
What does vulnerability mean to you?
In a lot of cases, it means saying “I don’t know.” As a leader, you’re expected to have all the answers. Well, we don’t have all the answers right now.
When the pandemic hit, we had to figure out how to pivot and be there for our employees and the people we serve. We had to discard our assumptions and think carefully about what our team members and customers actually needed. And we were surprised by the solutions people were able to come up with.
It’s so easy to say, ‘here’s what we should do.’ It’s much harder to ask people, ‘What do you think we should do?’
We determined that in terms of what we do for our customers, it isn’t about growing our business—sure, if there’s a need, we have a solution to offer—but more about making sure they have the resources they require. Take home services companies—professionals like plumbers, electricians, and cleaners are super busy right now, because everyone’s stuck at home and everything’s breaking. For us, it was natural to say, “How can we help you, home services companies?”
We wouldn’t be able to figure these kinds of things out if we didn’t work together. When you’re in a leadership position, you surround yourself with smart people, but empowering and trusting those people is ultimately what matters. It’s so easy to say, “here’s what we should do.” It’s much harder to ask people, “What do you think we should do?” But that’s the only way to access innovation and ideas, and to maintain camaraderie.
How do you go about communicating with employees and making sure everyone gets heard?
It’s intentional. You have to be intentional about the way you check in on people. You have to reach out and listen, because you can’t always see when someone is having a hard time.
We do this in several different ways. We have an internal executive AMA [ask me anything] channel, as well as regular Q&A video sessions, which we did daily earlier in the year, when things were more chaotic, but now happen on a weekly schedule. Then there’s live chat, optional team lunches—communication has evolved so much, and you don’t have the luxury of grabbing someone for coffee when you’re miles apart.
We also do formal one-on-ones every week with employees. I do skip levels and speak to my direct reports’ direct reports. It’s non-intrusive. It’s not meant to invalidate anyone’s authority and experience, but to provide access to me and allow people to raise concerns safely.
You have to reach out and listen, because you can’t always see when someone is having a hard time.
Our executives run these meetings without agendas of our own. If there is an agenda, the other person is driving it. This is a fundamental shift in terms of strategy, but leaders need to make the change, especially right now.
We were doing a lot of this before 2020, but the conversations have become much more fluid this year. It’s often just about letting people vent. This morning, I was talking to someone who’s missing the office and social interaction. We both know it’s not a great idea to return to the office right now, but this person appreciated having the ability to just talk about it.
So many working professionals are stuck at home right now, dealing with bad news, crises, and unclear boundaries between their work and lives. It seems like a perfect recipe for burnout and disengagement. How are you making sure Ruby’s employees take care of themselves?
We want people to know it’s okay to not be okay right now. It’s okay to be distracted. Work is always going to be there, and there are a lot of things pulling us away from work right now. The goal isn’t to eliminate the distractions, but make it easy for people to come back to work, get centered, and stay focused.
Those of us in positions of leadership can model this. I was in a recent meeting and my five-year-old daughter was logging into school at the same time. I helped her get online—I muted myself but didn’t hide it. I wanted to let people see me and know it was okay, that work isn’t the only important thing. The lines are so blurry. There is no start and end to people’s workdays.
It’s okay to not be okay right now.
Our responsibility is to provide compassion and trust when people are struggling or distracted. If we don’t, we’ll breed a continued divide that’s harmful both personally and professionally.
At Ruby, we’re fortunate that our executive team has led through transparency and integrity from the very beginning—starting with Jill Nelson when she founded the company nearly two decades ago, and continues today under CEO Kate Winkler’s leadership.
Has it been challenging to keep the lines of communication open when the future is so uncertain?
I think times like right now are when communication is most important. We may not always have good news, but we need to keep listening and talking to our employees. Earlier in the year was especially difficult. People were nervous. They were seeing their friends and family members get laid off. We stayed committed to remaining transparent. Our top priority is always making sure everyone stays employed, and to do that means that we had hard choices to make—and our people needed to know about that.
Communication builds trust. It’s what makes us rally together when we need to. As an organization, we’ve helped people affected by fires, people who have lost their houses. None of that would have happened if people weren’t talking to people. It’s evolved into a fire relief fund, and now a Ruby disaster relief fund. After all, we’ve seen that fires—along with other equally traumatic crises—can strike at any time.
As executives, we’re always tuned in and listening. You have to be there for your employees. You have to be there for conversations, including the hard conversations like the ones around equity, diversity, and inclusion. How do we listen to our BIPOC community? How can we look out for everyone on our team? There isn’t always a perfect answer. The conversation can raise really hard topics that should be discussed.
A lot of companies say they have an open-door policy, but that door isn’t open in practice. What makes Ruby different?
When we say we have an open-door policy, we really mean it. Every Ruby executive blocks out three hours in the middle of the week for office hours, in which anyone can schedule a 15-min meeting and talk to us about anything.
This also serves as an opportunity to get to know people, and as a bonus, you might learn about some untapped skills they might have. Maybe someone’s interested in blogging, or doing some graphic design. You don’t know unless you talk to them.
It’s so easy to be human. It costs no money.
I’m fortunate to have like-minded people in leadership roles at Ruby. Our CEO, Kate; our COO, Stephanie; Jace, our CFO; Katherine, our Chief Product and Technology Officer—everyone shares the same commitment to transparency and humanity.
Honestly, I find it baffling that so many companies don’t lead with the same values. It’s so easy to be human. It’s so easy to respect the humanity of employees, customers, and the community. It’s the easiest thing in the world, and it costs no money. Our alignment and commitment to foundational leadership values are some things I do not take for granted.
How can organizations handle social justice issues without alienating employees who see them as “too political” or fundamentally disagree with the protestors?
Conventional wisdom is that you should never discuss politics at work, but this year it’s been impossible not to. There’s so much going on in the United States and around the world, and people feel a lot more open talking about it. But you don’t want to offend or isolate someone on the team, of course.
Frankly, there’s no easy solution. There’s no way to keep politics out of work entirely. Everything is a political issue right now—even masks! We need to talk about it but talk about it carefully, in a way that sparks more conversations rather than causing people to self-isolate. Sure, we’re making mistakes as we go through it, but we need to remain open and willing to listen.
This isn’t about politics, but about humanity.
There’s a lot leadership can do to help their employees navigate these conversations. At Ruby, we have an employee experience team that works with people to draw boundaries for themselves and stay connected to what our company is about; namely, creating and building community.
For us, this is more than a political conversation. We’re aligned to things that are human. We want to be on the right side of equity and racial justice—not to score points, but because we care about people and the communities we serve.
In June, during the height of the protests, we sent out an email stating that this isn’t about politics, but about humanity, and that we have to stand up for people who don’t have a voice.
This email was met with different opinions from both inside of the company and outside of the company. I’m okay with that. I’m okay with disagreements. It’s not like every decision we’ve made has been met with the approval of 100% of the company.
For me, navigating these issues effectively is about connecting them back to our values. It’s explaining the why of the decisions. When people understand the context, we can agree to disagree rather than engage in hostility. This isn’t just a work lesson, but also a life lesson.
How do you avoid over-communicating or over-promising?
There are ways to share within an organization that give people enough information without veering into irrelevance or uncertainty. We trust in our company framework to make sure everyone knows what they need to know as soon as possible. We have an extended leadership team, then people managers, who deliver information further down the organization, while other messages are controlled and distributed from the very top—CEO videos, for example.
That said, I’m not sure that overcommunication is something to worry about. Is everyone watching every video we sent out? Probably not, but people do respond. I’d rather err on the side of overcommunication rather than trying to decide what information people need/want to hear.
It’s like any relationship. My husband and I tell our kids, “We’re not going to be mad if you tell us the truth.” We’d rather know everything because dishonesty only makes a situation worse.
With a workforce, it’s a little more complicated, but the goal is the same. You have to match people where they’re at and give them multiple communication options. Wherever they’re at, they should feel comfortable sharing what’s on their mind and motivated to do so. It allows us to get to the point where people don’t feel repercussions—then people stay positive when the world is literally on fire.
This is especially important in our line of work. When we’re taking calls from customers, what would normally be a three on the emotion scale is a ten because of the pandemic. We have to be the calming, professional face for these businesses that are also at a 10, worrying about payroll, how to keep up with the long list of things they are juggling and also staying safe while they do it.
What would normally be a three on the emotion scale is a ten because of the pandemic.
It’s up to those of us in leadership to set the tone. People will follow you if you lead with sincerity. Keeping people engaged and motivated means being compassionate, listening, and providing solutions when you can. Any form of help and humanity makes a difference.
For example, we recently created a community for parents on staff. We offer videos for working parents—you can park your kid here for an hour with colored pencils and paper, so you can take calls distraction-free. That only applies to a segment of the employee population with children of a certain age, but it really helps those employees. Sure, maybe that’s technically not our problem to solve, but why not help parents who might be struggling right now?
You mentioned a few other examples of helping and supporting employees in specific, personalized ways—coffee, basic essentials, fire relief, and so on. What’s the value of doing this versus sending everyone a general gift basket or care package full of snacks and herbal teas?
WOWism is one of our core values. We define it as using every opportunity to anticipate people’s needs and delighting them with solutions before they even ask for them. We do it for our customers, so why not for our people?
This is one of the core tenets of effective leadership. You don’t treat customers differently than you treat your people. You don’t ask of others what you wouldn’t do yourself. Why would you ask your team to go above and beyond for your customers and not do the same for them? These values actually predate our current leadership team. They started with Jill back in 2003.
Back to the personalized touches. A generic gift basket is okay—the intention is there, but the execution might be off because leadership isn’t paying attention. I can imagine someone receiving a bunch of tea bags right now and thinking, “Really? Why don’t you take that $30 you’d spend and give it to the ACLU instead?”
I think about how I would want to be treated. I don’t drink tea. I don’t drink coffee. Anyone who knows me knows my source of caffeine is a can of Diet Pepsi. If you knew me, you’d deliver a case of super cold Diet Pepsi to my house. That’s what would make me happy.
It’s so easy to find those details if you listen and pay attention. It’s not like people hide who they are. All you need to do is listen, take mental notes, and connect dots. And then, when someone is having a bad day or needs support, taking care of them is as simple as can be.
We’ve talked a lot about taking care of other people. How do you take care of yourself?
[Laughs] My lines are very blurry. I’m in Chicago working for a company based in Portland, Oregon. The hours are long. I often miss dinner with my family. But when I have pockets of time to sneak out and connect with family, I take them. Work is important and so is family. And when I decide I’m shutting down for the night, I shut down for the night.
My balance comes in many ways. It’s fluid and agile—no two days are the same.
Sometimes, I have to make difficult decisions and compromises. My mom sometimes helps out with my kids—in a socially distanced way, of course. If one of my kids asks, “Can we walk to Nana’s?” I might think, ugh, today’s a bad day, but you have to prioritize family. I make it work. You have to prioritize what matters to you to be present at work.
And at work, it’s not just about the work. I’ve been doing walking one-on-ones with team members recently. We connect in a personal way, without the pressure to look at a project.
Prioritizing the important things also means creating boundaries and honoring those boundaries. It’s okay to change a meeting from video to audio if you need to do something around the house or just don’t feel like showing up on camera that day.
My balance comes in many ways. It’s fluid and agile—no two days are the same.
What are some other fun, non-work-related things you’ve been doing at Ruby?
We do company trivia every three weeks as a team. It started with a template I found online. I ran it once, and Michelle [Ruby’s VP of Partner & Strategic Marketing] was like, “I’ll do it next time.” She’s run it ever since and taken it way beyond what I could have. The trivia is a mix of personal and professional information, and it goes deep. For example, she’ll show photos of cities, and you have to name the city and which Ruby team member was born there. I’m thinking, how would anyone even know that? [Laughs]
In other circumstances, we’d be doing a happy hour, but this is a fantastic alternative. It’s so nice to see people laughing and having a good time. Not everyone shows up, but for those who can, it’s so much fun to come together and talk smack. In fact, I’m proud to say I won the most recent one. I showed up this morning showing off my crown.
I don’t want to say the pandemic has any benefits, but this kind of activity has been a powerful and unexpected boost for our team dynamics. We’re coming together in new, exciting ways. Something like trivia wouldn’t have happened if we weren’t forced to think differently. I can honestly say our team is stronger and more innovative because of what we’ve gone through together.