Change at Work

Going Remote Overnight: Day 10, with Rachel Kaplowitz

When one CEO took her team remote overnight, she quickly learned the importance of work rituals—as well as scheduled fun

Like many leaders, Rachel Kaplowitz, CEO of Honey, was forced to take her team remote in response to COVID-19. Here she shares lessons learned from her first 10 days as a remote team:

  • Set up your stack. In addition to her own tool, Honey, she also recommends Loom, ChartMogul, Clubhouse, StatusHero, and of course, Slack.
  • Establish rituals. At the beginning of each day, the team gathers to ask three questions: “What did you do yesterday? What are you doing today? Do you have any blockers?” At the end of the day, the team then checks in to see if they accomplished what they set out to do. In addition, every week, they hold a “State of the Company” meeting to encourage full transparency.
  • Take personal time. Encourage your team to take care of themselves, whether that’s taking a break to play with their children in the middle of the day, or stepping away from work at a reasonable hour in the evening.
  • Don’t forget to have fun. The team has virtual happy hours (complete with alcohol delivery from Drizly), hosts a Virtual Cafe in which they come together as a team and don’t discuss work, plays games, and more.

Read the Transcript

Jane Garza:

Next, we have Rachel, who is the CEO of Honey. I actually ran across Rachel on LinkedIn the day that we decided to do this conference, which was probably like 10 days ago, I think. But the amazing thing is that she had just had the whole company go remote overnight, like I think many of you have, and she was posting on LinkedIn daily updates of what she was trying. We thought immediately, “This would be an amazing case study. Let’s talk 10 days out from now and hear what the progress has been day over day.” She can share her insights with all of you, and so that you can get some perspectives between companies who have been remote from day one and have been remote for two years now with their entire population, versus are switching to remote suddenly and experiencing that transition. So I’m so excited to hand it over to Rachel to get started. Hi, Rachel.

Rachel Kaplowitz:

Thanks, Jane. Hey, everyone. As Jane said, I’m Rachel. I’m the CEO of Honey. I’ll tell you a little bit about it. You’ll actually see it, because that’s where my presentation is living today. But to caveat this whole thing, I am not an expert at remote work. We’ve been doing it literally for 10 days. A little insight into who I am as a person and who we are as a company. We all work together in a New York office, within arms distance of each other. We have a really close relationship on the team. We turn around and ask questions all day. We have lunch together every day. Being apart from each other is a very foreign thing for us.

A little bit about me. I’m the CEO of the company. I come from the sales business development side of things, not the engineering side, and we’ll talk a little bit about that as we go through our learnings. And as just a person, I’m a mom of two and share my home with my husband. So that’s been a really interesting factor, dealing with the working from home stuff. But I’m going to share my screen, because I have some tactical takeaways for you, some things that have worked, some things not so much. But I always like to walk away from these presentations with some examples.

Jane, is that coming through okay, you can see it as a NOBL presentation? Awesome. So I’m presenting, just for context, from Honey. So a little bit about my company. It’s really interesting. We are a company intranet, so we power internal communications for companies. And a lot of our clients are actually some of them fully remote, a lot of them global, and thinking about remote communications all the time. So this is a really interesting experience for us, the builders of this software, to experience what they’re experiencing firsthand. So it’s going to, I think, really impact the way we’re thinking about product, which is a really cool kind of side effect.

But I think for the sake of today, I’m going to talk to you a little bit about why we made the decision… we made it early, you can see we made it on March 5th… and then some of the things that we think about in this, which are bucketed into people, fun, wellness, productivity, and then some challenges I’d love feedback from you guys on. So to begin with, the reason why we started this. So, March 5th, that was over 10 days ago. This is day 10 of us working from our homes. This was two Thursdays ago, before the world decided, in New York, that we were going to be working from home.

I made the decision coming into work. I was canceling my flight to San Francisco. I was supposed to go out there for the big Sasser conference, which I’m sure a lot of you guys were going to also. And I was like, “You know what? I don’t want to find a San Francisco airport. I feel stressed, uncomfortable, unsure about what’s going on.” And I was realizing this and canceling my flights as I was taking New Jersey transit into Penn Station. It’s like, “If I’m uncomfortable flying into San Francisco, how can I be doing this day after day in New York with so much uncertainty?”

I mean, I knew that, “I’m in the position of being the CEO of the company. I can make decisions about how we operate, but if I’m feeling stressed like this, my team is surely feeling stressed about it, maybe not that specifically, but other things related.” And we are a people first company. I think that there are a lot of teams that create these values. They live on our website, they’re something we talk about at off-sites and retreats, but it’s so rare that you have such a specific time to be able to actually execute on them. I mean, our very first value here is people first, and so I realized that we are actually, in a really great way, set up to be remote.

We are a software company, so we are really privileged in that way that we can ship a lot of the what we do just to online. But why make people be stressed out getting to work just because we like to be with each other and because we’re expected to be in the physical same space? So I made the decision a little over two weeks ago to ask everyone to work from home. And the advantage that we had going into that was that we were able to prepare. So we took that Thursday and Friday to really think through what we wanted as a team.

I even was able to send them home with a care package on Friday before we left, filled with granola and some wellness snacks, some swag, so that everyone would have some of those creature comforts around them as they went into it. As Jane said, I’ve been documenting our experience on LinkedIn and Twitter since then. Every day I post in the morning and the afternoon a bit about what happens. So you can definitely follow me there, and I’ll show you how to do that later. But today’s presentation is just like a wrap up of some of the things that have been really good for us and some of the things that have still been challenging.

The first thing is starting with the tools that had been really helpful. Obviously, Honey. That’s what you’re looking at here. This is an intranet. This is how we house longterm information. So, company-wide updates, resources like sales collateral or templates, best practices, and then links to tools like this. Obviously, you just need a central repository, whether that’s a big Google Doc or something like Honey. It’s really great to have the whole team centralized around something.

Clubhouse. That has been awesome for our project management. This is where we host our product roadmap, do our Sprint planning. Having that visibility into what our engineering team is working on at all times has been amazing. And our support tickets have gone up so much at Honey, just because there are so many teams that are now shifting to remote and thinking about using our product in a different way. So as a result, we’re seeing more feature requests or questions about how to use the actual product. So being able to put that into Clubhouse and having really quick response that’s so transparent has been amazing.

Loom. I know everyone’s been talking about this probably all day. Got to love them. It’s a great short video recording tool. So if you want to just explain something that’s not really translating over Slack or in a Zoom conference, just take a quick video and share that, whether it’s with a customer or internally.

ChartMogul is a really great tool and really important right now. This is a great way to be transparent about your revenue, and your subscription analytics, if that’s relevant to your company. Right now it’s stressful and there’s a huge impact on economy, people have questions about viability of work, and so it’s our responsibility as leaders to make sure that everyone knows what’s going on and that everyone feels secure. ChartMogul does that for us in a really great way, so everyone has insight into the trends happening with revenue coming in.

We can see, are there customers who are doing layoffs and they’re decreasing their account size with us? What can we do to help them? Is there something that we can do to make it a little bit easier for them right now? Is there something that we can do to make working from home work for them, things that we’ve learned? We can reach out in that way. And on the other side, we have a lot of teams who are doubling down on Honey, because now communications is even more important, they’re involving contractors and people that weren’t part of their initial subscription, so it allows us to see it. So, highly recommend sharing that visibility with your team.

We have Status Hero, which is a great way to do automated standup. So it’s a quick way to see what everyone’s working on, what bottlenecks they’re seeing, what they completed yesterday, where they are in their progress. And obviously, Trello and Slack, popular tools always, not just work from home. Trello, this was actually recommended to me to use as an onboarding of new employee tool. We’re going to be hiring our first remote employee next week. She was supposed to be starting in the office, but that’s a change of plans. So we just completely redeveloped our onboarding process to live in Trello. We’re going to be able to move all of the things that she’s supposed to do in her first week or second week through that Trello board experience, which will be pretty cool.

Slack. Obviously, everyone knows Slack. I think what I would recommend here, it’s been good for us, is just having a remote update specific channel, so you have a designated place for everyone just to write, “Going to lunch. Doing some brainwork.” You don’t want that to be all over the place or in your general channel. Just have it there. It’s really helpful to understand where everyone is throughout their day.

We’d love to hear tools that you guys use. I know that the panel before me had some really great ones, especially around design, but just collecting them. I think Jane said in the last panel, every tool’s different for every company, so find what’s right for you and be creative with it. I’m being creative with Honey right now. It was never supposed to be used like this as a conference presentation tool, but it works. It’s what we got and it’s a really nice way to do it virtually. So, giving me some cool ideas for the product itself, of course.

The groups that I’m thinking about in terms of just bucketing information that we’ve been experiencing here. I’ll start with fun, because we all need a little bit of fun right now, some things that have been really fun for our team, which is really important to break up the day. Here are those care package that I told you about. It’s what I sent everyone home with on their last day. So it’s been really nice to have those. If you didn’t get that chance… like a lot of teams, they made the decision middle of the night and all of a sudden they were remote… we can still get things to people.

Last week, we did a virtual happy hour. Kat, if you’re watching this, thank you for your amazing photo. I surprised everyone on the team by sending them a bottle of wine through Drizzly so that we could all actually have a drink together during our happy hour, which was super fun. They all thought that it was like a phishing scam, though, because I didn’t tell them it was happening and they’re like, “I’m not clicking on this link.” So, really proud of our cybersecurity there.

Something else that’s been really fun, we do a Honey Virtual Cafe, which has been recommended to me by another team through one of my LinkedIn posts. It’s one day a week we get together as a team and we don’t talk about work at all. This is the first week. This was hosted by Jay, our head of client services, and he did the hot seat, is what he called it. So he asked everyone on the team a bunch of rapid fire questions. Everyone had 30 seconds to answer. Here’s some example questions here, like, “If your parents let you get a tattoo at 13, what would you have gotten?”

So we were able to learn a lot about each other. It was pretty hilarious and a lot of fun, like a much needed break in the middle of the day. And this past week, we did a game day. We played Quiplash, which is a really fun game. You can get it from Jackbox Games, costs about 10 bucks to download. You’ve got to rig it together with your phone and Zoom and the game itself, and you definitely need to be charging your computer. But it was also super fun.

Jumping from fun to productivity, some things that have been really helpful for us as a team and then for me personally. The meeting schedules, keeping them simple and routine have been really great. Every morning we start with an all hands meeting. Very simple. Three questions, “What did you do yesterday? What are you doing today? Do you have any blockers?” We all go around and say that. We write it down. So at the end of the day we do another all hands and we talk about, “Did we get it done?” So it’s a really nice way to keep us focused, make sure things are happening.

It’s also a really nice way to make sure we start and end the day. That’s really hard to do sometimes when you’re working from home, I’ve realized. I’m doing a really bad job. My team will tell you that I’m responding to them on Slack at 3:00 in the morning, which I really need to stop doing, but sometimes when the kids get in the way, that’s the time that I actually have time to read some of the stuff they’re sending over. But this is a nice way to just document the beginning and end of the days.

We also continue our weekly meeting that we’ve always done in the office. This is the state of things at the company. Again, transparency is so important across the company right now, as people have so many questions, both about, “When are we going back to the office?” and, “Are our customers okay and how can we help?” It’s very important to make sure that you have time for this. One-on-ones are more critical than ever, too. Everyone’s dealing with their stress in different ways. Maybe you have a roommate or maybe you’ve brought in a family member. Maybe you have two crazy kids downstairs, who are thankfully very quiet during this presentation.

But everyone is coping with this in a different way, and obviously, the “this” is really scary too. This is a global pandemic. This is affecting a lot of people in really hard ways, and it’s really hard to digest that. So making sure that we have that time and space to be there for each other in that way. And then we end every week with a Friday Retro. We ask the simple questions, “What worked? What didn’t? What should we try? What should we stop doing?” I think making quick changes that your team can see super transparently and quickly goes a long way when you’re working remote, and seeing that there is flexibility and we can make these changes happen.

Next topic, wellness. This is something that’s really important to me and this is something I fail at a lot now. My life was a lot easier when my kids were not at home and now it’s really impossible. Moving around is really key. I’m lucky I have some set up in my house. The mirror is amazing for home fitness. Peloton, obviously, everyone’s been talking about. If you don’t have the ability to have any of that accessible, just going outside and running around. It’s been really nice to do that with my kids. Playing soccer in the mud the other day and really not feeling guilty about it. If you can do this at 2:00 PM when you would normally be working, it’s okay. I think leaders communicating that to their team, sharing this very visibly, too, making sure that they know that they can step away from their computer, has been really helpful.

Personal time is also really important. This is a glimpse into my evening activities, lately. I’ve been doing Zoom Hangouts and playing Quiplash or another similar game with various groups of friends I haven’t seen in a long time. This is my group of friends from high school, a couple of nights ago. We all haven’t been together in the same space for like 15 years, so it was really nice for all of us to get together. And as I said before, eliminate guilt. It’s really, really hard for everyone. Share when they’re hard. I think that’s really helpful for everyone to hear when people are hitting those moments.

One day, I felt really guilty because I was with my kids and I wasn’t doing work for an entire afternoon. I was dealing with nap time and making sure that they were entertained. Another day, I was feeling really guilty because I was sitting here on the bathroom floor on a call and doing some Sprint planning while my kids were just having a meltdown, and I just prioritized that call over it. Sometimes you’re just like, that’s what you do. It’s not something that I’m the most proud of, but it’s the reality, for sure.

Jane Garza:

Yeah, I see some plus ones. I’m sure a lot of people are feeling that right now with kids not being in school and everyone’s trying to navigate how to balance it all.

Rachel Kaplowitz:

I’m glad to have that company. I’m sorry that you’re dealing with it, but I think it’s helpful just to say it and own it, and we’re all in it together.

Jane Garza:

Yeah. Especially for you as a leader to be modeling that, I think that’s so huge.

Rachel Kaplowitz:

Appreciate it.

Jane Garza:

I just want to jump in and say, we have about four minutes left. I’d love any questions from the audience for Rachel before we wrap up. I see one here. One is, just how did you set up those norms and who was part of setting up the conversation, that list of meetings that you showed? People really liked that. Everyone’s asking for a copy of it. They just want to know where did that start and how do you know who should be in those meetings?

Rachel Kaplowitz:

A lot of the meetings were just meetings that we were doing already. The kind of aggressive, every day, morning and evening all hands was not something we were doing. But everyone, I think, wanted that, because we just wanted that social interaction more than anything. Again, we had that day and a half to plan this before we went remote two weeks ago. So what I did, I just met with every head of each department and asked what would be most helpful for them, and they were able to chime in with their thoughts. And then actually I published our new working from home policy and agenda to our [inaudible 00:16:51] of Honey and asked for feedback before we all left for the weekend. We had a big happy hour and conversation before we left and were able to make the edits there.

Jane Garza:

Amazing. That’s great. I’d love any other questions from the group on what they’d like to hear. I see one here about onboarding. Do you have an image that you can show of that Trello? If it’s not readily available, that’s okay. I think what people are probably most curious about how has your hiring or onboarding changed now that you’re remote?

Rachel Kaplowitz:

Sure. I did have a copy of the Trello board somewhere. I’m trying to remember where I put it. It was actually not the one that we’re currently using because I’m still creating that. But it’s basically just set up, in the columns of every week there are specific checklists that they should be doing. So it’s obvious things, like, “Sign up for your Salesforce account or your Outreach account.” We’re onboarding an SDR right now, so very sales specific. And then there’s going to be things that are a little bit more role specific, like, “Understand the customer journey.” And in that situation they’re going to be paired with someone from our team, probably someone from client services or sales, to walk them through our typical client journey and making sure that those moments are paired with people from different teams.

So not only are they onboarding and understanding their technical role, but they’re onboarding to the culture and starting to get to know the people, not in these big all hand settings, but in these individual one-to-one scenarios. So I’m happy to share that. I’m actually happy to share all of this, if it’s helpful. I can even create a communal Honey organization here and we can continue adding resources and ideas here with each other. We’ll figure out the best way to get it around. The best thing that I’ve learned is that if you ask questions on LinkedIn and Twitter, I think the kind of good thing to come out of the social distancing stuff is that people are really craving interaction and people are really going out of their way to help and give their time.

I asked about onboarding the other day because I really want it to be a good experience for her, and someone reached out to me from Berlin and said that he would walk me through how they do this in Trello. So we spent 30 minutes together. He walked me through all of his notes in Trello, and Notion, where they keep all of their onboarding information, and really helped equip me with this. So, ask questions. People are really amazing right now and being really generous with their time. I’m happy to do it too, once I figure it out.

Jane Garza:

Yes. That’s what I’m just going to say. It’s so true, as are you, being so generous with your time joining today and talking through all of your practices and building this out specifically for this audience. I so appreciate everything. There’s so many smarts here. Rest assured that we will share out all of these resources. Any last parting thoughts or big learnings from these 10 days of going remote that you’d like to share before we start to switch over to our next session?

Rachel Kaplowitz:

Yeah. I think the thing that obviously has been the most helpful for me is how we met, Jane, is this public accountability. Every day on Twitter and LinkedIn, I post my agenda, what I do. This was a little bit over a week and a half ago on March 10th, before my kids were home and it was nice and clean in what I was doing, although still a little bit crazy. I thought it was hard then. And this is my agenda, I think, from last night, and now you can see that it’s moved to a spreadsheet, because I have to watch what my kids are doing, what I’m doing, and balancing my husband’s work schedule also. But I’m sharing some videos every morning, just about a question or something that I’ve learned that day. So if you want to keep that conversation going there, I’m happy to engage and continue the conversation.

Jane Garza:

Amazing. Thank you so much. I’m going to start to pivot to our next bit of sessions here. Thank you so much, Rachel. We so appreciate you joining us today.

Rachel Kaplowitz:

Thank you, everyone.

Jane Garza:

It’s been such a pleasure. Bye. Let me share my screen. Here we go. So, we are at our choose your own adventure portion of the day. We’re going to have four breakout rooms right now. They’re all about remote work, and four different topics. Kristen has just posted the links in the chat. If you were here earlier, you probably saw some shuffling of our Zoom links because we had a little problem earlier in the day. So we would recommend you use the links in the chat or refresh the conference page and it’ll have all of the updated links on our website, which is at the bottom of this slide right here,

Our first break out room is Hiring and Onboarding. It’s a perfect transition from this last conversation. How do we do that on a team that is 100% remote? And we’ll have Jordan Husney of Parabol walking us through that. Our second session, The Truth About Agile and Remote Working (It Can Work!) with Collin Lyons of UsTwo. Our third session, How Subject Matter Experts Can Adopt a Principles-based Approach To Flexible Work with Kate Rand of Beyond. And then our fourth session, Remote Work: Caregiving During Uncertain Times with Amy Matthews and Sarah Barnaby. You may have seen a little bit earlier in the day if you joined us for their earlier session. But what I’d love for you to do now is pick which place you want to go to, go ahead and click the link, and we’ll meet you over in that breakout room. Thank you all so much. See you shortly.

Published March 30, 2020

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