Jordan Scott of Cobble on How To Communicate With Your Team Effectively Even If You Are Rarely In The Same Physical Space

Have face-to-face interaction that isn’t about work. When you don’t have little moments of random, spontaneous conversation like you normally would in an office, you need to find ways to manufacture that. For us, we like to use Gatheround (previously known as Icebreaker) to play games and have one-on-ones with team members we might not normally interact with.

Weare living in a new world in which offices are becoming obsolete. How can teams effectively communicate if they are never together? Zoom and Slack are excellent tools, but they don’t replicate all the advantages of being together. What strategies, tools and techniques work to be a highly effective communicator, even if you are not in the same space?

In this interview series, we are interviewing business leaders who share the strategies, tools and techniques they use to effectively and efficiently communicate with their team who may be spread out across the world. As a part of this series, I had the pleasure of interviewing Jordan Scott.

Jordan Scott is a decision-making entrepreneur and content creator. She is the founder, CEO and Chief Editor of Cobble, an app designed to help people make better, faster decisions together. Jordan graduated from NYU’s Gallatin School of Individualized Study in 2015. She began her career as a news associate at CBS This Morning before launching her startup.

To date, she has raised $3 million in seed funding, with thousands of users who have swiped over 495k times on dates and experiences and is quickly expanding Cobble’s offerings to new cities adapting to culture. Jordan has been profiled in ForbesFOX 5 Good Day New York, and more.

In 2017, Jordan created idk tonight, a website and newsletter that provides NYC couples with curated date night plans to help couples answer the timeless question: “What do you want to do tonight?”. After winning NYU x New York Jets No Huddle Challenge and Entrepreneur Magazine’s LIVE 5-minute pitch competition, Jordan launched Cobble, the first app that supports couples in “life after the swipe.


Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

Igraduated from NYU’s Gallatin School of Individualized Study in 2015 and began my career as a news associate at CBS This Morning before launching my startup.

In 2017, I created idk tonight, a website and newsletter that provides NYC couples with curated date night plans to help couples answer the timeless question: “What do you want to do tonight?”. After winning NYU x New York Jets No Huddle Challenge and Entrepreneur Magazine’s LIVE 5-minute pitch competition, I decided to officially launch our app concept, Cobble. In June of 2020 (in the craziness of the pandemic) we launched, raised $3M and hired 20 people.

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

Having a “male-sounding” name has led to some pretty interesting interactions. Due to the nature of our startup, we often go out around New York trying new restaurants, experiences, etc. in order to decide what’s worth being on the app for other users. We do these “date night ride-a-longs” on our Instagram Story and they’re super entertaining. My husband and I walk in, and every once in a while, the manager/owner will walk right up to Nick and say “Hi Jordan, thank you so much for coming.” It’s always awkward that within seconds, everyone involved understands what assumption was just made. That the CEO and founder of a tech startup must be this male standing in front of me, and not his little blonde date. Nick very much enjoys pointing at me and saying, “Nope, actually she’s Jordan.”

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

I love the quote “What you seek is seeking you ” by Rumi. If you’re passionate about something, you think about it constantly, and you love daydreaming about what it could become, it’s already on its way to you.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

My mom has always made me feel entirely capable of whatever it is I wanted to do. Whether it was voice lessons, drum lessons, getting into NYU or quitting my job and starting a company — she basically said if I wanted to do it, I could probably do it successfully. Even though becoming a famous performer didn’t pan out, I’m grateful for her unwavering belief in me. And in a way, pitching your startup is some form of performance — just with a way better payoff than applause.

Ok wonderful. Let’s now shift to the main focus of our interview. The pandemic has changed so many things about the way we behave. One of them, of course, is how we work and how we communicate in our work. Many teams have started working remotely. Working remotely can be very different than working with a team that is in front of you. This provides great opportunity but it can also create unique challenges. To begin, can you articulate for our readers a few of the main benefits of having a team physically together?

I am unique in that I actually launched Cobble and hired my entire team during the pandemic, so I’ve never experienced having a team all together in a physical space! In the past, I would say that the energy when you’re actually in the room together is palpable and runs through everyone. However, I think we’ve done a great job of bringing that energy through Zoom through several tactics.

On the flip side, can you articulate for our readers a few of the main challenges that arise when a team is not in the same space?

For Cobble, we’re not dealing with just virtual issues but also time zone issues! The beauty of hiring remotely is that you have access to the greatest talent all over the world. Our team spans from London to Paris to Chicago to LA to New York and more. Sometimes you wish you could just get everyone in a room, lock the door and iron out challenges over pizza and beer. That sounds like a dream and one day I think we’ll be there again.

Fantastic. Here is the main question of our interview. Based on your experience, what can one do to address or redress each of those challenges? What are your “5 Things You Need To Know To Communicate With Your Team Effectively Even If You Are Rarely In The Same Physical Space ? (Please share a story or example for each.)

  1. Have face-to-face interaction that isn’t about work. When you don’t have little moments of random, spontaneous conversation like you normally would in an office, you need to find ways to manufacture that. For us, we like to use Gatheround (previously known as Icebreaker) to play games and have one-on-ones with team members we might not normally interact with.
  2. Don’t let Slack create miscommunications. If someone sends a Slack that is not abundantly clear, I like to hop right on a Zoom and chat about it — even if it’s a 2-minute video call, it’s better than wasting any time going in the wrong direction.
  3. Give out weekly Emoji Awards. Every Friday our team awards different emojis for people who really shined that week. They’re called the Values Unicorn, Twerking Llama and Screaming Goat. I discovered this through a Tweet — here it is. It’s really been a fun morale booster at the end of the week!
  4. Don’t skip the small talk. And I don’t mean the weather. Before diving into each call, have actual human interaction and ask each other about how their day is going — if they took a cool midday workout, or tried a new coffee shop. Ask them what their plans are for later that night. Getting straight to business everytime can feel exhausting.
  5. Pick a day each week to have absolutely zero Zooms. That day for us is Thursday. And Thursday is a beautiful day where everyone gets unlimited focus time. I highly recommend it!

Has your company experienced communication challenges with your workforce working from home during the pandemic? For example, does your company allow employees to use their own cell phones or do they use the company’s phone lines for work? Can you share any other issues that came up?

The only rule is there are no rules. Just kidding. But really, Cobble takes the approach of working when you feel most motivated to work (and of course, showing up to any scheduled meetings and work hangs). It’s one of the beautiful perks of working from home and working remotely — if you prefer to sleep in, do it. If you prefer to stop working at 3 p.m., do it. Our team is respectful of each other’s schedules and that has worked for us so far.

Let’s zoom in a bit. Many tools have been developed to help teams coordinate and communicate with each other. In your personal experiences which tools have been most effective in helping to replicate the benefits of being together in the same space?

Gatheround/Ice Breaker is great for team building. It’s casual, fun and held on a bi-weekly basis.

If you could design the perfect communication feature or system to help your business, what would it be?

Based on our actual Zoom conversations, it’d be great if a voice recognition technology and smart bot could understand what the actual to-do’s are for each person and automatically create detailed tickets in Notion.

My particular expertise and interest is in Unified Communications. Has the pandemic changed the need or appeal for unified communications technology requirements? Can you explain?

If anything, I think the pandemic has highlighted which channels work (fast, human-powered live chat) and which ones do not (press 8 to speak to a human which is really still a robot for 20 more minutes!). Even if the world goes back to normal, I’d like to see a continued shift away from what does not work.

The technology is rapidly evolving and new tools like VR, AR, and Mixed Reality are being developed to help bring remote teams together in a shared virtual space. Is there any technology coming down the pipeline that excites you?

Nothing excites me more than bringing everyone together in the same physical space. I’m good with our current tools (as long as wifi holds up).

Is there a part of this future vision that concerns you? Can you explain?

Cobble is rooted in experiencing the world with the people you care about. If we’re experiencing the world through a screen, that feels a bit disappointing to me. I don’t think the world will ever fully be in Ready Player One mode.

So far we have discussed communication within a team. How has the pandemic changed the way you interact and engage your customers? How much of your interactions have moved to digital such as chatbots, messaging apps, phone, or video calls?

We quickly expanded our content offering to include movies, TV shows, recipes, virtual events and more. We made sure our product could serve couples and meet them where they were. Whether that’s in their bedroom or on a hike upstate. We’ve done plenty of Zoom user feedback interviews, which has been really fun!

In my experience, one of the trickiest parts of working with a remote team is giving honest feedback, in a way that doesn’t come across as too harsh. If someone is in front of you much of the nuance can be picked up in facial expressions and body language. But not when someone is remote. Can you give a few suggestions about how to best give constructive criticism to a remote team member?

There’s no good way to give feedback over Zoom that I wouldn’t say the same for in real life. I would recommend that you do not throw a mystery meeting on someone’s calendar without Slacking them about what your intention is with the call — you don’t want to be giving someone anxiety all day long.

Can you give any specific ideas about how to create a sense of camaraderie and team cohesion when you are not physically together?

  • Gatheround — fun games, meet people you wouldn’t normally interact with.
  • Work Club — a large chunk of time (usually 3–4 hours) where everyone is on Zoom and muted. If you need someone, you can flag them. Trying to create a fake in-office experience! Totally optional.

Ok wonderful. We are nearly done. Here is our last “meaty” question. 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. 🙂

Be impeccable with your word. One of the four agreements by Don Miguel Ruiz. Don’t gossip. Speak with integrity. Say only what you mean.

How can our readers further follow your work online?

TryCobble.com and @CobbleApp on Instagram

Thank you so much for the time you spent doing this interview. This was very inspirational, and we wish you continued success.


About The Interviewer: David Liu is the founder and CEO of Deltapath, an award-winning unified communications company that liberates organizations from the barriers of effective communication. Liu is known for his visionary leadership, organic growth strategies, and future-forward technology. Liu is highly committed to achieving a greater purpose with technology. Liu’s business insights are regularly featured in Forbes, Entrepreneur Magazine, Tech Crunch, and more.

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