Paul Murphy of Toucan: “Be human”

Be human. Our most important piece of advice when it comes to remote work is: remember that your co-workers are human beings. It’s easy to forget that. In an office environment, it’s easy to notice when someone is unhappy or overwhelmed. You can see it in their face. When we work remotely it’s much more […]

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Be human. Our most important piece of advice when it comes to remote work is: remember that your co-workers are human beings. It’s easy to forget that. In an office environment, it’s easy to notice when someone is unhappy or overwhelmed. You can see it in their face. When we work remotely it’s much more difficult to read those signals. Sure, some people are very dramatic, even on camera, but a lot of us aren’t. We have impassive video-conferencing mannerisms and it’s impossible to tell how we feel. This is even more true if communication is primarily over Slack or email.

A few months ago one of our colleagues’ mother-in-law died. He was out for a week helping his wife and father-in-law with cremation, etc. When he came back he seemed to be in reasonably good spirits considering what he’d just gone through, and we all picked up where we left off. The following week he seemed a little down, but nobody asked him about it. I later found out that his mother had died over the weekend and that because of travel restrictions he’d had to attend her funeral on Zoom. We collectively failed him. Even though we knew he was in a fragile state, none of us had asked him how he was doing. Looking after each other is so basic, but it’s easy to forget. We shouldn’t. It’s important to remember that we are working with other human beings, especially when we are all remote.


We are 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 Paul Murphy, co-founder of Toucan, a new, social-first video platform. He is a serial entrepreneur, having built 6 previous startups with 3 successful exits. He has technical management experience working across the United States, Latin America, Europe, and Asia. He attended Columbia College.


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?

Hi, I’m Paul Murphy, one of the founders of Toucan, a social-first video platform. As part of the executive team, I work with our CEO Antonia Hellman every day but, funnily enough, we have never met in person.

Antonia and her brother Ethan were Stanford students whose life was upended by the Covid crisis. They were sent home last March. Antonia wasn’t many credits from graduating; Ethan hadn’t finished his freshman year.

Not the college grand finale Antonia anticipated. Not the college experience Ethan expected.

I was a student a long time ago. My life was also upended by the crisis. I was on a business trip to New York and London when I realized what was happening. I phoned my wife in Bangkok — where we lived — and suggested she and our daughter meet me in Rome. I assumed that the Italian government’s reaction to the virus would be more benign than the Thai government’s. We’ve now been in Italy for a year. I arrived with a carry-on suitcase. Everything else we own is in a warehouse in Bangkok.

Not the two-week business trip I anticipated.

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

I lived and worked in New York writing software for big banks. One day my building shook so hard that a painting fell off the wall. I thought a truck had run into the building. When I looked out the window I couldn’t see a truck, but I noticed smoke and paper pouring out of one of the World Trade Center buildings.

That morning changed my life. The project I was working on was shut down, and the US economy ground to a halt. I moved to London, which is where I met Antonia’s dad.

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

Sorry, I don’t do life lesson quotes! Too reductionist. I get inspiration from stories, and the stories that interest me change over time.

At the moment I’m listening to a lot of recordings of Offenbach’s Tales of Hoffmann. I’m particularly interested in the first tale in which Hoffmann falls in love with an automaton. That seemed far-fetched in the 19th Century, but VR and AIs are getting us closer to the day in which that will start to happen, if it hasn’t already.

I guess that’s more disquieting than inspiring. If you ask me next month I bet it’ll be something else.

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?

Oddly enough, it was a neighbor I spoke to by chance.

He was working on his Harley. I told him I thought it was beautiful. After chatting a while I discovered that he was ex-Navy and that he liked to run. He ran marathons. I’d never run a mile. I was bookish and believed that exercise could lead to no good. My mother encouraged this and had our family doctor write a note saying that I had a heart condition. Needless to say, I never attended a gym class in school.

After our chat, I thought I should give running a try. The next day I ran with my neighbor and threw up after a mile and a half. Angry that I was so weak, I made two impulsive decisions. I decided to quit smoking and I told my neighbor I’d run the next marathon with him. Even though he’d just seen me finish my first run in style, he didn’t laugh. Instead, he said he thought I could do it with the right training.

Six months later, when I crossed the finish line of the NYC marathon with my now very good friend, I understood that I could do anything with enough preparation.

Difficult never scared me again.

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?

Having a team physically together is wonderful.

It’s much easier to explore ideas and solve problems when people are in the same room. No online collaboration tool comes close to replicating a room with a whiteboard, paper, and markers. The space matters, and the artifacts matter. We’ve evolved to communicate face to face, to build things together. When working in person we benefit from body language, which conveys so much information. The way someone sits, stands, and moves tells us if the person is thinking, distracted, confused, annoyed, engaged, and so on.

It’s easier to get to know people when we’re physically together. Working through a hard problem and walking to grab a sandwich can take place almost simultaneously. An off-the-cuff comment while waiting for a coffee can be more revealing than months of online dialogue. It’s the nature of in-person contact, the highest bandwidth interaction we can have with another human being.

In a large organization, it’s easier to form relationships with people outside your reporting structure. The last time I worked in an office I learned a lot about inbound sales because I met the salespeople in the kitchen. Had that company been virtual I would never have met them, and I’d be poorer for it.

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?

The three biggest challenges are coordinating work, avoiding distractions, and minimizing misunderstandings.

Without shared artifacts, whiteboards, kanban boards, and even desks covered in paper, it’s difficult to coordinate work. We do our best to reproduce these online but humans are tactile creatures. A post-it on a calendar can be far more motivating than an entry in an electronic to-do list. Physical artifacts tend to be simple. We don’t write and rewrite ideas on a whiteboard. We get close enough to the essence and leave it alone. Digital documents allow us to futz around with ideas far longer than necessary, often without benefit.

Our computers are pits of distraction. Trying to focus while processing email and notifications is difficult. Any work that requires concentration suffers in that context. Even one-on-one video meetings suffer because of these distractions. I try to counter this by always running our conferencing software in full-screen mode, but who hasn’t checked email when the discussion flags?

Siblings misunderstand each other. Husbands and wives misunderstand each other. Naturally, colleagues misunderstand each other. It’s so easy. Even when we share a background, we don’t share all our assumptions.

In a physical context, misunderstandings are minimized by all of the information conveyed by presence. A turn of the shoulder, a half-smile, or a hand gesture can take the sting out of a phrase in a way that allows the listener to hear what the speaker intended. Those are mostly missing online, so we have to be very, very careful about how we say and hear each other. I try hard to avoid offending or upsetting people, but I manage to with great frequency.

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. No one can read our minds.

This is the most important thing to remember in any relationship. It’s just as important in a marriage as in a business.

It’s easy to assume that we’re all working from the same assumptions but that is rarely the case. We all have different backgrounds, different knowledge, and different feelings. When speaking or writing in a business context it is critical to always explicitly state both base assumptions and developmental logic. There’s no better way to cause misunderstanding than to assume that someone else knows what you know, or can connect the unseen dots the way you do. Always, always, always be explicit!

My favorite example of different backgrounds leading two people to completely different conclusions happened to me when I lived in New York, a long time ago. I was friendly with one of the mechanics at a garage near my house. One day in early September I was buying gas and he called over: “Where have you been?” “I’ve been away.” “What for?” “I was at my camp in Maine for the summer.” He looked at me completely confused for a second and then said: “Oh, I thought you’d been in jail.”

That day I learned that “being away” is a euphemism for “being in jail”, at least in New York.

I can think of many examples in which different knowledge, in the absence of mindreading, has led to misunderstanding. In my case, those almost always involve computing. Last week, I was talking to my brother, who’s a chef, and told him to just do something in Google Docs. Long silence. “What’s Google Docs?” Don’t worry, that doesn’t make me feel smart. Conversations with him usually leave me feeling like I know nothing. I’ll complain about some dried beans my wife bought and he’ll say something like, “Well, you can either plan ahead, get your mirepoix going, and throw them in after parboiling them, or you could fast-soak them and do whatever you want.” Are there instructions in a Google Doc?

2. Be explicit

When working remote, time-to-feedback can be much longer than in centralized working. When working on a project with someone who is busy, 24 to 48 hours could easily elapse between conversations. If instructions are vague, this could mean a lot of lost time.

We’ve all experienced the “bring me a rock” problem.

Boss: “Bring me a rock.”

Us: “This one OK?”

Boss: “No! Not that one. Too big.”

Us: “This one?”

Boss: “Too small!”

You get the picture. If every exchange is separated by 24 hours, it’s going to take a long time to come up with the rock the boss really wants!

“Bring me a rock” is of course a problem in centralized environments. It’s a waste of time. But in a distributed environment, that lack of clarity can be much, much worse.

Bottom line: be explicit!

3. Be more organized than you think you need to be

We’re all organized. Sort of. We know where we store our documents, we know where the latest version is, and we know what we’ve changed. We may know, but will someone else be able to figure it out?

Universal search has made us lazy when it comes to digital organization. We assume we’ll be able to find something simply by searching. That doesn’t always work out.

Last week we were gathering materials for an investor. We needed the most recent budget. A quick search through our Google Drive turned up 9 documents named “Budget” 😱. Realizing our mistake we looked in the “Finance” folder and found:

  • Budget.WIP
  • Budget.2021
  • Budget.final

So “Budget.final” must be it, right? Well, maybe not. It was the oldest of the three. By this point, our Finance Director had gone to bed. She lives in a completely different timezone. Our response to the investor had to wait till she woke up.

You didn’t ask for tips, but these are the ones we try to follow:

  • Always file documents in a predictable place.
  • If a document could theoretically live in more than one place, either drop a README file that points to the canonical location or take advantage of Shortcuts (in the case of Google Drive).
  • Either delete or stash old versions. We create a directory called OLD in just about every directory of our shared drive and move things in there. Why? Because people — especially me — are anxious about throwing out old versions of documents. This way we don’t get rid of them, but they can’t confuse anyone.

Being organized is both explicit and anti-mind-reading. It’s important when we’re all together, but critical when we’re working from different locations. It can be time-consuming in the short term, but in the long run this can save everyone time and prevent embarrassing mistakes.

4. Communicate top-down.

Keeping an organization moving in the same direction is difficult no matter the circumstances. Slight changes of direction at the top can be amplified as they move down the organization.

Here’s an example.

The CEO decides to change one of the company values from “brave” to “measured”. Small change. Doesn’t affect Legal, Finance, HR or, Product. But somewhere in Marketing, a team is spending weeks putting together a social media campaign about bravery. Three weeks later they ask the CMO for approval to launch and discover the change.

In an office, this sort of thing happens, but there’s a natural mechanism that tends to dampen its impact. By that of course, I mean gossip. Gossip sounds pejorative, but it’s just informal communication. In the above example, any one of the people in the meeting in which it was decided to change “brave” to “measured” might have mentioned it in the coffee room, or at lunch with colleagues. They might in turn have mentioned it to their friends and colleagues. Even in a big organization, gossip travels quickly, so it’s likely that someone working on the social media campaign would have caught wind of it long before launch.

Working remotely minimizes gossip. Sometimes that’s a good thing, but gossip has its place. Without it, we need efficient top-down communication to keep the organization moving in the same direction and to prevent unnecessary work.

5. Be human.

Our most important piece of advice when it comes to remote work is: remember that your co-workers are human beings. It’s easy to forget that.

In an office environment, it’s easy to notice when someone is unhappy or overwhelmed. You can see it in their face. When we work remotely it’s much more difficult to read those signals. Sure, some people are very dramatic, even on camera, but a lot of us aren’t. We have impassive video-conferencing mannerisms and it’s impossible to tell how we feel. This is even more true if communication is primarily over Slack or email.

A few months ago one of our colleagues’ mother-in-law died. He was out for a week helping his wife and father-in-law with cremation, etc. When he came back he seemed to be in reasonably good spirits considering what he’d just gone through, and we all picked up where we left off. The following week he seemed a little down, but nobody asked him about it. I later found out that his mother had died over the weekend and that because of travel restrictions he’d had to attend her funeral on Zoom. We collectively failed him. Even though we knew he was in a fragile state, none of us had asked him how he was doing. Looking after each other is so basic, but it’s easy to forget. We shouldn’t. It’s important to remember that we are working with other human beings, especially when we are all remote.

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?

Do people still use phones? I’m kidding. Well, half kidding. I don’t remember the last time I called someone.

All of my communication — internal and external — is over text, audio, and video, using a ridiculously long list of apps: Slack, WhatsApp, Line, Telegram, Signal, iMessage/FaceTime, Zoom, Teams, Whereby, and, of course, Toucan. I think I forgot email.

It’s honestly exhausting to keep up with all of these communication channels, and everyone has their own way of dealing with them. The younger ones among us are good at juggling and dealing with multiple synchronous communication channels. The older ones tend to rely on asynchronous communication — email, contextual comments in written materials — and shut off the real-time channels to get work done.

Needless to say, this inconsistency causes all sorts of headaches. It’s taken us a long time to develop habits that respect the characteristics of each channel, and we’re not there yet!

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?

Toucan is at the top of my list. Being able to get together in both a work and social context on the same platform is critical.

We make very heavy use of Google Docs which eliminates the friction of emailing documents around and keeping track of which is the “official” version. Well, most of the time. Google Docs takes the place of communal whiteboards. They’re different, better in some regards and worse in others. We’ve tried virtual whiteboards and haven’t liked any of them. They seem forced, trying too hard to replicate something physical, and awkward to use. We’ve all been putting pencil to paper since we were two. It’s difficult to replicate that flow with a mouse.

For development we primarily coordinate our work through git, today’s default. It works well.

We’ve tried a lot of other SaaS tools to coordinate and do work, but most fall by the wayside. Simplicity and predictability always win over a couple of cool features.

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

I would focus on size. To replicate in-person interactions the tools need to be human-sized. I would like to see my colleagues life-size in my office. And if we’re going to have virtual whiteboards I want them to be as big as real whiteboards. These require hardware that is somewhat outside our budget, but that will change. The challenge then will be having a big enough home office to install it all.

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?

UC hasn’t evolved the way I thought it would. We’ve just been through an extreme unbundling. The incomplete list of communication tools I mentioned earlier is proof of that. I have a feeling a backlash is coming and what I think of as “traditional” UC, i.e., all-in-one tools that make it easy to change modality, will come roaring back. It hasn’t happened yet because no one’s nailed all the modalities well enough. Also, decentralization has made it harder. When everyone shows up with their own devices you need extremely flexible UC infrastructure and endpoints.

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?

When you asked earlier about a perfect communication system, mixed reality was on the tip of my tongue, but I didn’t bring it up to avoid seeming like a wild-eyed futurist. Now that you’ve mentioned it though…

I don’t think there’s any doubt that mixed reality in some form is the future of our working infrastructure. With the right glasses, we won’t need the giant screens I mentioned earlier. And a virtual environment will give infinite space to store artifacts. That’s very exciting.

It’s also a little scary of course. Surveillance is going to be a concern. Also, we’re going to have to design things that make moving in and out of mixed reality feel natural. Our work at Toucan makes it clear that this isn’t an easy thing to do.

If you’ve ever spent time in VR you know it can be a tough transition. I can’t imagine spending an eight-hour workday in VR and then having to reconnect to my physical environment. Mixed reality is much simpler from that perspective. After all, software on our computers and telephones are a form of mixed reality. AR with a headset is just the next step.

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

As I just mentioned, VR is problematic. I can easily imagine people preferring a virtual environment to their physical environment. That’s weird enough, but what happens when we all interact with each other as avatars that don’t look anything like us and maybe have completely different physical characteristics and abilities? If most of our time is spent in VR, those avatars will become more real to us than our bodies.

I know science fiction writers have been writing about these problems for a while, but we seem to be getting close to the edge of the future scenarios they can conjure. Once we can plug ourselves into the Matrix I’m afraid science fiction writers are going to have to find another profession.

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’re in a funny situation because we’re building the tools that our customers use to communicate with us. We mostly meet our customers in Toucan. We’re keenly aware that many of them are facing the same internal communication challenges we are, so we spend a lot of time talking to them to understand their particular problems so we can address them.

Since we started the company just as the pandemic was hitting the US, we haven’t had to make any specific pandemic adjustments.

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?

You’re right. This is a big problem with being remote. Bandwidth matters. To that end, we try very hard to use as much as possible when dealing with sensitive issues.

It’s easy to misunderstand a Slack message, especially when dealing with multiple cultures. Emails aren’t much better unless you put a lot of effort into being clear, and who does that with email?

One of my CS professors, an old French guy, used to constantly complain about emojis. “Flaubert didn’t need emojis!” he’d yell at us. I bet Flaubert would have loved emojis, but I never dared say that to my prof. Emojis go a long way to softening the edge of potential written misunderstandings. People should use them more than they do.

Sorry, that was a total tangent. You asked a serious question. How do we give constructive criticism? We use Toucan, first because video is as close to real-life bandwidth as we’re going to get, and second because Toucan is less formal than platforms like Zoom and Teams. We’ve put a lot of work into making Toucan as comfortable as possible. We work with psychologists to figure some things out. Seems a bit extreme but it’s paying dividends. We constantly hear from customers that they feel more relaxed on Toucan than on any other video platform.

No matter the platform, talking “face to face” is critical. Delivering constructive criticism via email is too dangerous. It’s too easy for the recipient to misunderstand the feedback, or worse, get upset about it.

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

You’re making this too easy. To create a sense of camaraderie and cohesion you need to use a social-first video platform. And I happen to know a good one.

Seriously, using Toucan is a good start, but it’s just a tool. Once you have the tool to socialize virtually you need to figure out how to use it. I’m going to give you two examples that seem unrelated, but I can promise you they’ve both made a huge difference to our internal sense of camaraderie. The first is playing games, and the second is eating in front of each other.

Our CEO, Antonia, is endlessly creative. She’s also competitive, and likes to play games. Last November she decided that we should invite outsiders to our weekly social and play a game of Jeopardy. She put the whole thing together, and it was magical. Everyone loved it. I think the first blog post I wrote for Toucan was about that night. Since then we’ve played lots of Jeopardy together — tip, if you ever come to one of our games, be on Antonia’s team if she’s not MC’ing — and I know Antonia is working on a few others.

Now, let’s talk about food or, rather, eating.

I’ve always thought it was rude to eat during a conference call. I think most people do.

Why is it rude? Because we’ve been holding formal meetings on video platforms for a decade and during formal meetings, you don’t eat. You pay attention and take notes. This is well-known video-conferencing etiquette.

But the pandemic and fully-distributed work is changing that.

My wife works for a distributed recruiting company. A year ago she’d lock herself in her office when she had meetings. She didn’t want the dogs or our three-year-old making any kind of noise her colleagues or clients could hear. That’s changed completely. Home life encroaching on professional life is accepted now.

If a toddler interrupting an important discussion is acceptable, maybe eating lunch should be too. I think we’re getting there. At Toucan we work in seven time zones. It’s always someone’s mealtime. Why make it awkward for them? I have a very high metabolism. My mealtimes aren’t very elastic. When I need to eat, I really need to eat! My colleagues know that. I used to always turn off my video when I ate, now I do it less and less.

Last week I was having an informal chat with our CEO and another colleague. She was starving, got a snack and said: “I really like these meetings because I don’t feel bad eating while we have them.” That comment surprised me and I’ve been thinking about it ever since. Why should we feel bad about eating in front of other people online? We do it when we’re physically together. I think the acceptance of that behavior is changing.

Summing up the answer to your question “What has created a sense of camaraderie and cohesion at Toucan?”: games and breaking convention by eating in front of each other. It’s possible we’re a somewhat quirky company. Not sure how well this will translate to other institutions.

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. 🙂

If you follow my blog posts you know that my latest obsession is digital etiquette. I’m not going to go into all the details, but a few things are worth mentioning.

Eating or not eating on video calls is a matter of etiquette. Until the pandemic, it was considered rude, but as I said, I think that’s changing. One of the wonderful things about etiquette is that it evolves with society. I think we’re witnessing a very obvious case. Which makes me think I should probably write a blog post about it!

This is a trivial example, but it’s important in a bigger context.

Our transition from real-life interactions to virtual interactions happened in the blink of an eye in evolutionary terms. We haven’t adapted yet, and etiquette hasn’t caught up. Because of that, we’ve had to introduce coercive and oftentimes arbitrary replacements. “Rules of conduct”, content censorship, and platform banishment are the big ones. I argue that they are a very poor substitute for etiquette. We need to make a concerted effort to re-introduce etiquette into our digital life. That will solve a lot of problems that are currently causing such tension in our societies.

So if there’s anything I can do to inspire a digital etiquette movement, I will! As luck would have it I’m helping build a virtual social platform, so I have an extraordinary opportunity to work on this problem every single day. I hope your readers will spend some time thinking about this too.

How can our readers further follow your work online?

They should definitely give Toucan a try. I’m biased of course, but it’s an awesome platform!

I’m a pretty dedicated blogger and I write about a lot of random things, not just etiquette. My most recent posts can be found at https://toucan.events. I’m always open to feedback. Best ways to get in touch are email ([email protected]) and Twitter (@prmurphy), unless I say something stupid and get canceled!

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


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