215 FS Remote Work

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01:54 - Listener Request: Remote Work03:14 - Communication Technologies


PHILIP: Ugh. I remember seeing one of those hard disk drive, those removable disk packs. It was literally the size of a washing machine, like a US size washing machine to be clear. And if not, even a European size washing machine.

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CHUCK: Hey everybody and welcome to episode 215 of the Freelancers’ Show. This week on our panel, we have Jonathan Stark.


CHUCK: Philip Morgan.

PHILIP: Howdy.

CHUCK: Reuven Lerner.

REUVEN: Hi everyone!

CHUCK: I’m Charles Max Wood from Devchat.tv. This week, we’re going to be talking about working remotely.

We actually had a request for this from one of our listeners. His name’s Luca and I’m just going to read through this and then we can take it apart. He says basically, he wanted an episode on purely remote consulting where you perhaps never meet customers face to face. Then he was looking for communication technologies for meetings, chat and video conferencing, project management, day to day communication and software tools that you can expect customers to be familiar with and/or have installed. Then communication techniques on how to manage your clients’ expectations and discussion style, how to lead discussions, how to share impromptu drawings and sketches; how to make up for lack of non-verbal communication, how to [inaudible] communication pitfalls or [inaudible] or avoid in the first place and how to deal with time zone differences. Then he’s got a bunch of more questions here that he put under fundamentals.

So what about if what you’re selling is not a tangible product like software or plain communication like strategy consulting? How does that work? How do you do it? How do customers react if you suggest purely remote consulting? Can I use a random [inaudible] really expect to be sustainable or does it merely work for a lucky few consultants who are just so good or well-known to customers who accept this [inaudible]?

So let’s talk about – I think we should probably just start at the top because I think the communication technologies, we can list a few and I think those are probably the least interesting parts of this. I think mostly it’s the way that we deal with our clients since [inaudible] going to be the real kicker for those.

So I’m curious, what technologies do you use to communicate with remote clients?

REUVEN: Skype. Lots of Skype.

CHUCK: Yeah, I’m in the same boat. Skype. I also use Slack if I can but [crosstalk].

JONATHAN: Yeah, I use Slack extensively.

PHILIP: Yeah, I use Skype and there’s situations where – I guess I should say a lot of my clients are mentoring students and, say, it’s a group situation so I’ll use Google Hangouts because it’s so ubiquitous. I’ve recently started to become some enthusiastic about Zoom because it’s got a nice price point and it seems like they’ve figured out a lot of the simpler, lower hanging fruits stuff about how to actually make a video call, perform well in a variety of different bandwidth situations and so forth. And it lets – if someone can’t make a data connection, they can dial in with a plain old telephone connection which is nice.

CHUCK: Yeah. The other thing I like about Zoom in particular is that if you are sharing your screen, then you have a whole bunch of other tools you can use so you can draw pictures on your screen, circle different parts of your screen share and things like that. So it has some nice tooling that goes with that.

It’s not where everybody can draw on the screen but at least the presenter generally can. It tends to work really well. It’s my backup for everything else. For example, yesterday, I got on a call with Dave Thomas from Pragmatic Programmers because he’s speaking at a conference this week for me in Ruby Remote Conf and yeah, we just couldn’t get Crowdcast to work for whatever reason. So we hopped on Zoom then I’m like, okay, well at least we have an alternative. But yeah, it pretty much always works for me.

PHILIP: You bring up an interesting point; I think it is good. If you’re going to go all in on remote consulting which I have, it’s good to have a backup for pretty much anything that could fail. Of course you can reschedule and stuff because [inaudible] but I just like to have a backup. So if you’re on Skype, having some secondary way [inaudible] kind of fail back, Skype is not working, it’s a good idea.

REUVEN: I can tell you on that front that – so the Chinese chat program on your phone, WeChat, I found on many occasions when my Skype connection goes down, it’s more stable on the same network. And it does voice and video chats as well. You don’t need to know that Chinese use it, but it’s definitely worked with me into if you want to backup that works on your phone, that’s pretty darn reliable right now.

CHUCK: One other thing that I’ll just jump in with here as far as meetings and communication is that if I have just one person that I’m dealing with the client, [inaudible] two, a lot of times I’ll just push all of them in Skype – all of the calls, the meetings, the chatting, everything – I’ll just do it all in Skype.

If I’m dealing with a team of people or if there are a lot of people that tend to meet to know – at least know what’s going on, want to provide input and things like that, then I move in to these other options where it’s Zoom or Slack or things like that. But yeah, just one on one or one or two, I generally just go with Skype for [inaudible].

JONATHAN: I think that’s interesting – I don’t know if we’re making this distinction on purpose or by accident but I categorized all of my communication platforms into real time and not real time.

CHUCK: Yeah.

JONATHAN: So I’ve got text apps or platforms or whatever you want to say – the non-real time ones would include things like Slack or Basecamp but the real-time ones also would include Slack but not Basecamp.

REUVEN: I was going to ask you – I was going to ask if Slack is in the real-time or not real-time.

JONATHAN: Yeah, it’s both. It’s also in audio and it’s also – it’s not in video yet but Slack is really – it’s mainly text although they did recently add audio but it’s mainly text. Obviously, it’s good. People check into it and probably are using it already. But to Philip’s point, having a backup – probably have three of each of these categories so real-time, not real-time for text; real-time, not real-time for audio. Sometimes, we’ll switch in the middle of a call because one of them is just stinking. And video, also real-time, not real-time so like Crowdcast would be kind of both to do real-time, not real-time. Google Hangouts, Google Hangouts on the air or whatever that’s called. Whether or not you just share your screen’s a factor; you can do that with Skype, you can also do it with – join.me is another one I use all the time. Also screen shares or video, not real-time. Screenflow is a great recording tool, recording and editing tool very easily used.

I don’t know if we’re going to talk about non-real time stuff later but I probably have 30 apps that fall into one or more of these categories that I use more or less regularly.

CHUCK: We also haven’t brought up email which I think we just take for granted.

JONATHAN: Actually I was going to say, I specifically do not use email for client conversations.


JONATHAN: It’s too much of a mess.

CHUCK: I actually like – I think we’ve discussed this before and I think basically what we said was that if it’s not at Basecamp or something, it didn’t happen. Then I really like having that one canonical place that’s not the place for all of the other conversations that I have for everyone else.

JONATHAN: Exactly, yeah. It turns your inbox – it forces you to check your inbox constantly which is a disaster for your productivity.

REUVEN: Do you guys find that the quality of these real-time conversation systems or communication systems, the quality has anything to do with whether you’re paying for it or not because I definitely – I’m paying for Skype. I pay for it to [inaudible] a number in and then calls out. And I don’t feel like that I have a bunch of other experience than my friends who have the free plan.

PHILIP: I see no correlation except for this one weird edge case where I was on Skype saying – the pricing in the US is $2.99 a month and you can call any phone number in the US and Canada or North America. And I upgraded to get a number where people could reach me in [inaudible] via Skype has – my cellphone’s not the greatest where I live and the call quality got way worse, noticeably, dramatically worse. So in this case, there was an inverse relationship but that’s the edge case. I really see no correlation. It’s like there’s amazing free stuff and there’s paid stuff that’s mediocre, what [inaudible] you, go to webinar and do some of those conferencing [inaudible]. Super expensive and [crosstalk].

CHUCK: You are being so nice to them. [Chuckles] Mediocre? [Chuckles]

PHILIP: Anyway, yeah, I don’t see any relationship.

CHUCK: I guess they’re mediocre because they work. Yeah, I hate [inaudible] maybe go to webinar. I found that they’re just way too complicated and the quality just isn’t there. I get way better experience out of even Google Hangouts which is free.

PHILIP: Yeah. That’s the table stakes is that it works. Now, it’s all about making it easy and fluid to use.

CHUCK: But I find that generally, it sounds like all of our experience more or less lines up there.

PHILIP: I guess I’ll be the guy who is like kind of on the other side of the table from people who are really dogmatic about one tool. Because I feel like – the question here, the larger question is like working with people when you’re not physically there with them all the time or maybe ever. And if you’re being too dogmatic about tool choice which is something I personally was into five years ago – I was super dogmatic; I was like we’re going to find the best tool and we’re going to champion that tool; we’re going to persuade out clients to love that tool whether they can even use it or not, it was just – I felt like that was a very long-headed approach and it got in the way of effective collaboration at a distance which I feel like it’s what this larger discussion’s all about. How can you make that collaboration really effective?

So I will say that there’s so many choices that I feel like there’s no need to be dogmatic about it.

CHUCK: Oh I’m dogmatic about it. Whatever makes me work the least, I’m dogmatic about that.

PHILIP: Really? But if your client was like, “We really can only use this because our IT department has approved it.” What do you do in that case?

CHUCK: Yeah. [Inaudible] how much work it is. [Chuckles] I mean, really.

PHILIP: Yeah, sure. Of course, it depends.

CHUCK: So if it’s just not worth the effort to figure it out, then I’ll just tell him, “This is a pain in the butt and I’m going to – there’s a pain-in-the-butt premium to use it.”

PHILIP: Hm. What about the rest of you guys? What are you doing in that situation?

JONATHAN: When the customer – I can’t think of a time this has really happened. I recalled that it has happened to me so [inaudible]. I remember one person who wanted to use HipChat with me which is terrible on mobile which is where I mostly live and a little bit of a [inaudible] about that. But in general, I liked it when the customer imposes the platform on me because then if it stinks, it’s not my problem.

The other thing is I don’t charge by the hour so I don’t care if it’s [inaudible] or it’s like – I don’t have to worry about it. If they want me to use their conference line instead of Skype, fine; if they don’t want to do a video call for a big project kickoff, fine. No big deal.

CHUCK: Yeah, I can’t think of a time where somebody’s actually picked a tool and I was just. Well, I can but there were a bunch of other contractors working in the same contract [inaudible] delivering code using hourly [inaudible]. So it’s like okay, this is a pain in the butt, it’d cost you more because it’s taking more time to do.

REUVEN: I’m trying to remember – trying to think most of my clients, who am I doing development are kind of small startups. And so they’re using the same sort of technologies as I am. Recently, a few of them have said, “Oh, just put it on our Slack channel.” I’m thinking, “Wow, that’s great.” They’re really with it.

My big clients are basically where I’m doing training, so how much technology do I really need to use to interact with them? I go there and I plugin another projector. The only exception is perhaps that my new teaching for Cisco because they – online teaching for them because they own WebEx so they require that I use WebEx for my teaching. But you know what, I have actually grown fond of it. I don’t think it’s just Stockholm syndrome or something; I think it’s actually pretty good. [Chuckles]

CHUCK: It’s definitely Stockholm syndrome. No, I used WebEx for years so I don’t know.

REUVEN: No, it’s like if you know what you’re doing and you’re willing to learn – there’s still tons and tons of features and I have no idea what they do. But not a small number; that actually work pretty well.

CHUCK: Yup. So how do you use these tools then getting into the communication? Because we’ve kind of gone off this way a little bit; how do you set my expectations and discussions.

I’ll give you an example if you like; I did some work for a client and I was building them an internal social network kind of thing. I would leave my Slack signed in because I’ll just walk away from my computer when I’m not working and they got ticked off because I wasn’t there at ten o’clock in the evening when they tried to Slack me. Other times, they expect me to pick up my phone but it’s after when I generally work and so I just don’t answer it. So how do you set those expectations? I figured out that [inaudible] need to do some of that upfront but on an on-going basis, are there other expectations you have to set?

REUVEN: Let me step back for a moment from that question and just make it clear. Even though it’s probably really obvious to everyone listening, communication is probably the most important thing for you to have with your clients in general. If it is remote, then you’re going to have to work extra hard to make them know that you are there and know that you are working on things. It just won’t cut it for you to disappear for two weeks and come back and say, “Look, what an amazing feature!” unless they know that you’re going to be gone for two weeks. Let’s agree with them, that’s fine.

So using these tools is necessary so that they will have what’s known in the business – on a [inaudible], it’s like presence, a sense of presence. Are you around? Are you doing something? And if so, what are you doing for them? So that they’re not surprised. So I find that using a lot of these tools, whether there’s a task tracker, whether it’s chat, whether it’s something of [inaudible], whether it’s Basecamp or something, it’s just like the note ‘I have not forgotten you; I’m still working on your thing and I care’.

JONATHAN: I have a similar – sort of similar take on it which is definitely agree that communication is hugely important and even more important once remote. When I’ve got projects going, I try pretty hard to touch the project – I try to touch the client at least once a day. Since I’m not getting paid by the hour, it’s not like they care if the clock is ticking or not ticking but it’s like what you said, they just want to know that it didn’t fall off the map. They want a heartbeat coming from the other side of the internet that somebody’s still on it so they can chill. They’re not really worried about – for me, they’re not really worried about “Did he climb into a hole and he’s going to need 120 hours this week? That I wasn’t expecting.” Is it more like – it’s really for me like – to put their minds at ease, to decrease risk like, “Stark’s got it. We don’t have to worry about it. He’s on top of it. We’re good.”

CHUCK: So how often do you check in?

JONATHAN: I usually do – it depends on the gig. It depends on how crazy the gig is. When it’s coming up to delivery, it gets pretty – it can turn into a real flurry, a real-time chat, conference calls that we’ll just jump in and out of for [inaudible] to lead throughout the day. That’s usually just crunch time so usually, there’s just like [inaudible] where people need to get a little bit of extra handle at the beginning so they don’t have buyer’s remorse. They trust you. They can with me; it’s weird because I get paid in advanced. So they write the check, it disappears into the air and then they don’t want me to disappear; they want me to immediately be attentive. So usually a little bit more in holding at the beginning.

Then they’ll go through dry spells when half of their team goes on vacation or there’s some blocker from a third party or whatever and it’s quiet for a week or even two weeks. But usually, I try to check in on a daily basis; maybe at most two days go by but it really depends on the stage of the project.

CHUCK: Is that an email or is that also through Basecamp or whatever?

JONATHAN: Never an email; never ever. Always Basecamp or something more real-time. So if it’s something that – I’m working with this one client right now. They’re new to Basecamp, they’re new to Slack. They prefer old school telephone landline conference calls of those [inaudible] set on the table. So it’s – I’m the most active person in Basecamp and I’m not even in there that much but that’s where I do it.

I don’t know if they’re looking at it or not. I presume they are and we may have a weekly phone call or I catch them up on what’s going on.

CHUCK: Yeah, I just worry that mine would be a whole bunch of nothing to report, still waiting to hear back.

JONATHAN: Yeah, I wouldn’t do that. There’s usually something going on. I wouldn’t keep on saying – one thing I will do is – I’m not afraid to – so I’m coming [inaudible] outside as a consultant but I’m not doing any dev work. So I’m not afraid to not throw somebody under the bus but be like, “Okay, I posted this message for you,” I’ll post a message for somebody and they will get back to me for four days which is really no skin off my nose but the team, the upper management, might be a little ticked off by the time the next meeting goes around and nothing has moved forward. So I’ll say something like – and I’m not really a project manager but I will do something like try and ping the person on some other channel or I’ll ping the boss or comment all in Basecamp like, “Can everyone reply to this so I know that you’re getting the notifications?” Something like that. Like if it’s just totally dead and I’m not 100% sure that people are even getting the message. If I see no activity then that makes me a little nervous so I’ll try and stir up some.

PHILIP: I think there’s two aspects to this. One is there’s like a flow of information aspect and there’s also the fact that I think most of us wat our clients to feel good about having hired us so there’s like maintaining the emotional connection.

I think there are times when you would want to communicate even if there’s nothing to report or even if it’s all status quo. I think there’s reasons to communicate just to maintain the way people feel about a project that’s in progress. I think that’s where I, in the past, have fallen down a lot and I think a lot of people can do better. It’s just remembering that you want to keep the emotional temperature of the project positive. Not that you want to [inaudible] a paper over something that’s going wrong but that’s a big part of why people spend larger and larger amounts of money is because of how they feel about things.

REUVEN: I just spoke yesterday to a new potential client for development work. Someone calls me and says, “Well, we’re working with this company and they’ve been doing some software development. Maybe we’ll continue to work with them, maybe not but we’ve just lost all trust in their ability to work on the way we want.” I think to myself, clearly, they’re going to leave this company because why – if she says out loud that someone she just met on the phone ‘I don’t trust them’.

CHUCK: Yeah.

REUVEN: Right? It’s got to be bad. She’s telling me, “Oh, we spent this crazy amount of money for doing this little amount of development,” and on and on and on. So you don’t want it to get to that point where your clients are badmouthing you to other people saying, “Oh my god, I can’t trust them anymore,” that’s a bad situation to be in. I mean it’s good for me but it is bad for them.

So I found that having just a weekly phone meeting, even if it’s ten minutes, five minutes and they can find out what’s going on development-wise – but I can – almost an important practice or even more important is to tell them or to ask them what’s new with business? Where do you think we’re going now? And I find that now it doesn’t help me to look ahead and say, “Oh, they’re probably going to need X and Y and Z,” because the business is going in that direction. But it makes them feel like, “Wow, you actually care about the business and not just churning out code and getting this stuff.”

CHUCK: So I have to ask then because I ran into this problem with a couple of clients where I basically said, “I would like to have a call every week so we can go over what I’ve got going on and what you’ve got going on,” and I get a lukewarm response. Now, it’s kind of the best. [Chuckles] Some of them were just like, “Well, you’re in Slack and we’re in Slack so we’ll just Slack.” How do you get them to the point where it’s like, “Look, I want the face to face over Skype or the voice to voice over some other system so that we can actually talk.”

REUVEN: My experience is people – my clients at least realized that it’s a whole different kind of communication. It’s more effective; it’s more instantaneous. You’ve got a fuller emotional sense of what’s going on. You can exchange things faster. Slack is great, Skype is great. When you’re on Skype, I am on Skype.

PHILIP: Jonathan, I would love to hear your thoughts on this. As I have gotten older – and for the record, I will be 42 this August.


PHILIP: The number of times when I’ll get a long, written communicate of some sort and then starting – hit the reply button or start to craft the reply and then get about two words from it and then go “you know what” and I’ll just erase what I wrote and be like, “Hey, would you be – would you like to get on a call and discuss this?” The number of times that has happened has gone up dramatically and I don’t know if it’s just getting older. I used to hate when people did that to me because I’ll just be like, “Look, I’m busy. I want this to be asynchronous communication and now more and more, I’m defaulting to some form of synchronous communication because I feel like it’s more effective.

JONATHAN: I’m going to guess it’s less to do with [inaudible], more to do with the nature of the work.

PHILIP: Well I needed to ask an older man. [Chuckles]

JONATHAN: I am a fan of using the right communication medium for the job. So whenever we have a situation – the phone is great in a project context, the phone is great when you have a really fuzzy brainstorm that needs to happen with a – especially with a couple of – if there’s more than two people because that just doesn’t work in Slack.

PHILIP: And I think when you say phone, you just mean real-time voice.

JONATHAN: Real-time voice, yeah.

PHILIP: So whatever underlying [inaudible] is, doesn’t matter.

JONATHAN: Real-time voice, yeah. It could be Screenhero, it could be inside of Slack – whatever, but you can take a massive thread of five people talking over each other in a tech format and get the whole thing wrestled to the ground in ten minutes.


JONATHAN: In a conference call.


JONATHAN: It’s weird. It’s like – I guess it’s not weird, it’s just like different things are suited to different media. The thing that I hate about the phone is that you have to take tons of notes if you want to capture anything and then you’re the only one that has them. So then you have to put them into minutes like – okay, if the decision was made on the phone call, that drives me crazy.

PHILIP: You become the secretary, right?

JONATHAN: Yeah, so I try to catch that – it depends on the relationship. Sometimes I’ll be like, “Is somebody capturing this? [Inaudible] feel like it’s definitely not my responsibility but I try to stay away from that. It’s more like let’s just hash through this confusion like we just got into a snarl in some text thread. It was just – you click the phone button that’s staring at us and clarify what it is we’re talking about.

It’s usually when there’s a disconnect like people are talking to ask each other using the same work for different things, right?

PHILIP: Yeah, I think the reason I have that feeling like it might be associated with aging is because when I was in my 20’s, the people in their 40’s or 50’s who would always be like trying to get me on my phone instead of email, I just figured, “Oh, they didn’t grow up with email,” so it’s – like they’re technophobes, right?

REUVEN: Which might have been true at that time.

PHILIP: Could be but I think also, maybe they had the wisdom to understand when’s the right time to get on the stupid phone.

JONATHAN: Or maybe email just felt so impersonal that they couldn’t imagine how anyone would use it as a communication medium.

PHILIP: I will say that’s just – as I mature, as someone in the services business, I rely more and more on voice communication because I think if it’s used correctly, it can be so much more powerful.

CHUCK: What should I [inaudible] into with going on the phone though, especially off of like a text-based system whether it’s – any mail or Basecamp or whatever is that the second I say, “Well, why don’t we have a phone call because there’s a lot of information to communicate?” or because “I’m afraid that we’re missing something here in what we’re trying to say to each other.” Inevitably, it feels like – well not inevitably but about 70-80 percent of the time, the client gets on and just like, “What’s wrong?

JONATHAN: Trusting.

PHILIP: There’s the opposite problem of clients not being disciplined about respecting your time. That can happen and that’s why some people want to avoid getting on a phone call. I get that.

JONATHAN: That’s been more the keys with me is that someone who wants to bring it up, when you want to ask a question and they go off on a [inaudible] and you’re like, “Ugh, man.” I like to use a phone when it’s going to save time; that’s basically my thing. With a lot of the tools we’re mentioning, it’s so easy. Even in Gmail for crying out loud, there’s like a phone button. You can just – and inside Facebook messenger, there’s a phone button so pretty much anything. You can take pretty much any thread that’s going and just pull a rip cord and bring the other person’s device. So it’s pretty easy to switch back and forth between them.

But I think the big picture really is that you need – all of these are good for different things and you need to be pretty facile in switching between them. Maybe it takes a special skill; I never really thought about it like that but maybe the remote worker has a special skill that didn’t exist; to get off my lawn, a baby boomer group.

PHILIP: Chuck, to circle back, you had the question earlier, I assume you do want to have that real-time voice communication with the client. How do you make the case for it to them and – this is not some bullet-proof advice but if you frame it as – this is software development; there’s always going to be issues that come up. Let’s plan for a standing appointment every week to work through those issues or discuss them or keep your prize to the nuances. I feel like that might be one line of reasoning to use with someone who’s initially resistant to the idea, like a standing weekly meeting.

CHUCK: Yeah, I just put it to them as there are going to be [inaudible] in communication and the easiest way to clear it up is to get on the phone. Let’s just plan on being on the phone on a regular basis so that we make sure we’re communicating.

PHILIP: Yeah. It’s like an insurance policy against the misuse of asynchronous text.

CHUCK: Right, and here’s hoping that those calls aren’t that long because we’re actually doing well on the other [inaudible].

PHILIP: Yeah, I mean of course having an agenda. Maybe they need to see an agenda; maybe they are in assort of reactionary place of, “Oh god, please do not steal another 90 minutes of my day with your 45-minute meeting.” So having an agenda could work with that.

JONATHAN: One last thing I’ll say about voice calls – maybe not the last thing but one more thing is that it’s the most prone to frustration of all of them, like when the phone call’s going horribly just from a connection standpoint, [inaudible] dropping – you know what I mean, Reuven?

REUVEN: Yup. [Chuckles]

JONATHAN: People are [inaudible] it out or there’s a lag if we’re talking over each other; it is like keyboard-smashing fury so there’s that. It’s a much more emotional channel and there’s – I guess it’s touching on something that humans have been doing since BC. So there’s a million subtle cues and there’s so much more rich data in the channel that it’s a bad connection or things aren’t going perfectly then it can be a real drag.

I’m paying 1000 bucks a month to have an office so that I can sit somewhere quietly when I have to have phone calls because it doesn’t cut it from a Starbucks or whatever it is – the coffee grinder comes on and it’s like, “What? What?” [Chuckles]

CHUCK: Yeah.

REUVEN: Yeah. I have occasionally talked to clients from a train station – what a mistake. They’re like, “Oh, what’s that? Was that another train announcement? Was that your train? I just should not have done this.


CHUCK: So time zones. [Inaudible]


PHILIP: Yeah, I had a mentoring program participant who I persuaded to try moving from a completely 100% asynchronous text communication to a standing call with a client who is – he’s in the US, client’s in Asia so that’s a pretty dramatic time zone thing. Somebody’s got to get up earlier, stay up late to make that overlap happen and he had a lot of good things to say about it. He discovered – I think I remember it correctly – discovered one or two opportunities for on-going work that had not surfaced until we got on the phone with this client who was very happy with his work and they’ve been communicating successfully with asynchronous text but the phone call just added something extra.

I’m definitely on the side of talk to your clients real-time, regularly if you can. So I guess I’m also on the side of, yeah, if you’ve one day a week, if you got to not work until seven or eight but just maybe return to your workspace from Saturday or we’ll just go to a quiet place and have a phone call, it might be worth it. I think you should be considered. There’s plenty of other awesome thing about being freelance and working from home to offset that that I think it’s worth [inaudible] in the big picture. But I know it’s not always possible and it definitely complicates things.

REUVEN: I know this client in Chicago for years now and – so it’s an eight-hour time difference except for if one of us changes the clocks. And you know what, I got used to it and sometimes I would have late meetings with them and sometimes early. We always find a way that it would work. Also, that their morning is my afternoon or evening so it’s okay. And then, they added two more developers and two more marketing people. We all want to be on a weekly standup meeting or just a weekly update meeting. That was the killer, trying to find when everyone could make it.

So what we ended up doing was their 10 PM and my 6 AM and everyone’s unhappy but basically, we keep trying to find a better time and no one can think of one.

Other than that though, yeah, a little flexibility is not a bad thing. If I had to get up an extra hour earlier, go to sleep later to talk to people, not so bad. But that’s also because most of my communication with them will be asynchronous. So I can get away with once a week, once every two weeks talking real-time, and the rest being through email, IM, whatever.

JONATHAN: So clearly, a time zone – one major time zone thing is finding a time when everybody who needs to meet can meet but are there other – people have other time zone related issues that weren’t to do with asynchronous communication?

REUVEN: Emergencies. I sometimes had issues with emergencies and we were asleep, right? And I get up in the morning and see all these urgent email messages that came overnight. “Oh my god, oh my god, what’s wrong with the server?

CHUCK: [Chuckles] Yeah.

REUVEN: The better ones are, “Oh my god, what’s wrong with the server?” and then several minutes later, “Oh, everything’s fine now.” And I slept through the whole emergency and it corrected itself. That’s the best.

JONATHAN: Yes. Sometimes it’s [inaudible] makes things worst. What big tools do people use to prevent things like people missing meetings because of time zone confusion and that sort of thing?

CHUCK: I always send a calendar invite. In that way, when it shows up on the calendar and they accept, then I know that it’s an okay time for them. Then if I’ve got several people in different time zones, I don’t want to think about it, then I’ll just use [inaudible] Calendly or something because it’s pretty good about figuring out where time zones [inaudible] and then pick a time that does work for them, and then I just make the time available for that.

There was another one and I can’t remember the name of it but there are a bunch out there where you can actually just invite everybody to the same tool and it’s effectively a table with a bunch of times that are – that you’re available and then each person check offs the ones that they’re available. In that way, I’ll get support [inaudible].

REUVEN: Doodle?

PHILIP: Sounds like Doodle.

CHUCK: Yup, I think so.

PHILIP: Which I hate. Whoever thought a scrolling – infinitely right words for [inaudible]? [Chuckles]

CHUCK: I know, right?

PHILIP: [Inaudible] was a good idea but it does work and it’s useful. Actually, I have a coaching student who is this – one of these brilliant guys who just gets heads down in whatever he’s working on and the calendar invite pops up on his computer and he just doesn’t see it because he’s so focused. Like with him, I have started texting 30 minutes or 60 minutes before we meet which I know is kind of like from a power frame perspective sort of makes me the secretary. It’s not ideal from that perspective but from a larger perspective, I want a meeting to happen and I’m willing to do some ground work to make that happen so that’s – to me, that’s not out of balance. It’s just saying, “Look, if you guys can’t remember the meeting – I know that’s not really my problem but also, this meeting needs to happen so I’m going to remind you.”

REUVEN: I often, in order to avoid time zone issues, because especially when people are changing clocks in different countries, it can be a real pain to miss a meeting by an hour or show up an hour early because, oh, you change your clocks and I didn’t. So what I’ll often do is put a meeting in the calendar under their time zone. This way, I just say to people, “Oh, we’ll meet at 8 Eastern or meet at 9 Central,” and I’ll put it in my calendar as 9 Central. And my calendar then figures out wherever to have to be in the world and whatever time it happens to me. For me, it’ll tell me when that’s happening.

JONATHAN: Yeah, there’s a really good feature of Google Calendar that – it might be what you’re describing but it’s something that I use when I’m travelling. So next week, I’m going to be speaking at a conference in Las Vegas which is two or three hours earlier than where I live but I live and die by my calendar, like if that’s not in my calendar, I miss it. Let’s say my talk’s at 2:30 Central Time – what are they, Mountain Time?

CHUCK: Nevada is Pacific Time.

JONATHAN: Pacific Time, okay. So let’s say it’s at 2:30 Specific Time. [Chuckles]

CHUCK: Specific Time, I like it.

JONATHAN: You can put it in your calendar and then under the advanced settings of the appointment, you can change the time zone for it so that when I land there and my phone and everything updates to the local time zone, it’s at the right time. Because what I used to do is I’d be like, “Oh, I’m speaking at 2:30 in Las Vegas,” so I put it in a 2:30 Eastern Time and then I get there and it would bumble up to 7:30 PM and I would completely miss it or I would be in danger of missing it unless I paid [inaudible] time math which is everyone’s favorite.

PHILIP: On that note of time math, Fantastical is an app – it’s got a little feature that will transpose your entire calendar into whatever time zone you want so you could see it – like you’re over in [inaudible], you can see it in Specific Time. Makes it a lot easier to plan stuff. Anyway, I [inaudible] new but that’s a nice tool.

JONATHAN: [Inaudible]. Another thing I’ve gotten into the habit of doing is I use Calendly as well but when I – but that’s really a one-on-one. It’s hard for two people to pick a time in the calendar with Calendly but if I do have to send a time for something anywhere, I always include the time zone.


JONATHAN: Even if I know the people are in my time zone, I’ll say – and I don’t just say Tuesday, I’m very specific with it because it ends up – if you aren’t, it’s open for debate and [inaudible] but it’s potential for confusion. The benefit is that in Gmail at least – that’s what I use – if you put up full day and time in there, it will [inaudible] click on it and add it to your calendar. So the person on the other end potentially could just click it, see if – what their availability is in the sidebar and just accept it right there, like sent [inaudible] by. That’s a good thing, to always put the time zone so people know what you’re talking about.

REUVEN: Actually, I’m always saying “in your 12 or your one o’clock or your three o’clock”. And by the way, I always – I never say “next” like next Tuesday, next week. Always use a specific date. And I never say 12 AM or 12 PM, always 12 noon or 12 midnight.

JONATHAN: Yeah, me too. Totally. You can tell that [inaudible] deal with a lot of time zone. [Chuckles][inaudible] knew all that stuff.

CHUCK: Alright.

REUVEN: So just once you get burned by that and then you’re scarred for life.

CHUCK: So finally, his last question is basically what if you’re selling software or some kind of strategy consulting or something like that, do you do that completely remotely or do people react poorly to doing it entirely remotely or they’re going to want to meet you in person?

JONATHAN: Got a funny story there. Virtually all the work I do, my mobile business is strategy. Almost none of my clients are within a reasonable driving distance. I had one client recently who wanted to do a – we want small, [inaudible] thing. It was clear that I was not going. There was going to be no on-sights. They were a plane ride away and I wasn’t interested in doing that and I certainly didn’t price the gig that [inaudible]. So it came time to do the kickoff and they’re like, “You know, I think it would be better if we met in person for a two-day kickoff,” which I think was way more than we needed and was definitely out of bounds in terms of what I have priced like I said. So I said, “Yeah, I can’t make that happen but if you guys want to fly to me, I can make that happen,” [chuckles] to put in their mind, “Okay, that would cost us at least $15,000 to fly the team up to Providence.

Then I was like, “Well, if you really want me to come down there, I can give you a price for that. And I was trying to anchor high with their cost for flying to me. It was going to cost more than the whole gig; [inaudible] I was going to have to cancel a bunch of stuff, fly down from there. It would’ve been terrible. It was totally unnecessary but it is true that a lot of – it’s almost like the bigger check their writing, the more they want some kind of facetime, at least in the beginning. Frankly, sometimes I am open to flying to some place before I even have the job because I want to see the facility before I price it.

REUVEN: Oh, that’s smart.

JONATHAN: Yeah. So if it turns out – it could be [inaudible] with one company right now. It’s really hard to get a sense of how big they are, how big a project this is for them. It seems really big but I don’t want to way overprice it, give them a sticker shock because it would be a pretty cool gig but I definitely don’t want to underprice it. And I’m like it would probably only cost me a grand to fly there – plane ticket, overnight in a hotel, food and all that – it’ll be less than a thousand bucks. And this project could easily be way more – 50 times that so it’s worth jumping on a plane and – I guess what I’m getting at is sometimes it’s in your best interest to set up some face time rather than them forcing you to do it. Those are just anecdotes.

The bottom line is I barely have to see anybody in person and pretty much all I do is strategy so you really don’t need to do it. It’s just – I find that I can increase my fee somewhat by doing it if I feel like it, but you definitely do not need to actually be flying around all over the place or even driving around to be meeting with people in person.

CHUCK: I think another thing that’s a part of this is that if you can’t get them to trust you to work remotely, then you probably aren’t going to get them to – well, I guess you could but you’re not going to be able to get, in most cases anyway – my opinion and [inaudible] rambling – I don’t think you’re going to be able to trust them to drop the extra thousand, two thousand dollars for you to fly out and spend a day with them if they don’t trust you anyway. So really, what it comes down to is [inaudible], how are we structuring this? Do you trust me to get it done? Are you going to get a good value out of it? And I think if they see all of those things add up, then it won’t matter whether or not you’re remote.

And honestly, face-to-face over the computer is not the same as being in person but at the same time, for a lot of people, it’s good enough.

REUVEN: I declined where I worked with before. It must’ve been three or four years, all online, all on the phone. We spoke on the phone all the time and I was in the US at that time and then he says, “Tell you what, why don’t I fly you out here? Then we can get to know each other in person and strategize over the next few years of how the business is going.” That was a real turning point, a positive one in our relationship even though we’ve been talking on the phone everyday for years. It really cemented our relationship and gave us the chance to deepen it in many ways. So even if it’s just a one-time meeting, it doesn’t have to be the beginning even, it can definitely be worthwhile.

JONATHAN: Yeah. I just met for the first time in person, a retainer client that I have been working with for three years non-stop, continuously. It was a – exactly what you just said, Reuven, we’re close. We’re already close but it’s like that online close, when you actually go and have dinner with somebody, there’s just no – it takes a relationship to a level that is – it definitely did not get in Slack.

Is it necessary? No, but it’s really nice. If it’d make sense to do, it’s really nice.

CHUCK: I agree with what both of you are saying; I’m just saying I don’t know that anyone is more likely – I don’t know if a lot of people are more likely to hire you based on whether or not you’re going to fly out.

PHILIP: I think that it does something to a position you – has a little higher value, freelancer consultant, whatever – when it’s obvious to a client you could A, afford to fly to them without them having to pick up the bill and B, that you have enough control of your own schedule to arrange that. Most of those are going to be signals that this person is not scraping work from Upwork; they’re actually succeeding in what they’re doing. So in a sense – I guess I have to make an exception to even my own preference for doing everything remotely which is – it sends a real message when you can travel and it’s not a big deal for you to travel and you’re not like, “So who’s going to pay for this trip?”

JONATHAN: Yeah, totally. It’s a total power move. If you believe that there’s a real gig there, that it’s more – it’s a little bit of a gamble and it’s definitely no fun. I can’t stand traveling. I’m so sick of travelling. I’m fond of saying I will not get on a plane for less than $5,000 but I would, and I did just to a company that I just mentioned that maybe I would fly down there because this seems like a sweet gig. I think you get – these guys are not tired giggers and I’m going to be in competition with people who are players. Just casually saying, “You know, maybe I’ll just fly down there.”

I agree; Philip’s 100% right but it’s definitely a – it’s your ace card in your situation. It sounds like yeah – but I feel like it’s something that I worked up to. This isn’t something that I did starting out. I don’t want people to feel like you need to do this so that it’s some kind of strategy. It just naturally presents itself when you’re in this situation, you could benefit for it. You know what I mean? It’s like a tactful approach that I can apply in this case. I could just – be like, “Yeah, nevermind,” and not even worry about it but just has this whiff of a good – there’s something about it that seems like it’s going to be a really good project.

REUVEN: By the way, we’ve been with local clients here in Israel so I would often be willing to go and just meet them wherever for initial consultation. [Inaudible] going – and it’s a small country and most of these things were, say, half an hour away. But it’s half an hour there or an hour there and an hour back and it ends up taking half, three quarters of the day just to have this initial meeting.

At some point, my wife said to me, “You are the consultant. They want to meet with you. Why don’t you have them come meet with you at your house?” I was like, “Okay, I’ll try that.” And sure enough, people keep doing this. Most of my work is still training and everything but in the last month, I think I’ve had three different potential clients to come to my house and meet with me here. All I do was say, “Why don’t [inaudible] and meet?” They didn’t flinch at all. From their perspective, this was totally okay.

JONATHAN: I purposely chose to never have local clients because I live in a pretty small city and I don’t want to be running in them all the time. [Chuckles] So this is – for people who are listening, geez, 99% of my work over the last – since 2003 has been remote, completely remote. I have tons of clients I’ve never met so totally doable and now it’s easier than it ever has been because there’s just tools everywhere.

REUVEN: And it’s acceptable. I was in the newspaper when I came to [inaudible] and I was working remotely with a company in the US.  No one’s going to write a newspaper story about a telecommuter anymore. [Chuckles]

JONATHAN: That’s not even called that anymore, is it?

REUVEN: I don’t know what they – I think it’s [crosstalk] remote work – yes, yes [inaudible] myself once a year. [Chuckles]

PHILIP: That’s awesome.

JONATHAN: Put that in your positioning statement. [Chuckles]

REUVEN: I would say the hardest thing is being used to it if you’re not used to it. If you’ve been working in an office for a while and you’re going to work remotely from home with people all over, well, now you’re going to be used to not having office banter, not going and seeing a person, marketing online and everything. So it’s a whole lot of different skills and experiences but that doesn’t mean it’s impossible at all. On the contrary, it’s quite possible.

PHILIP: And I know that in some probably very few situations, depending on the culture of the client, you may be unable to influence them at a distance. If that’s important, then that may change some things because I know that that was a threat of discussion when [inaudible] was a new thing. People who would work remotely, we get passed over for promotions and that kind of thing. So I think some of this advice is certainly less applicable to remote contract workers or just remote FTEs.

CHUCK: Alright, well, let’s go ahead and get to picks. Jonathan, do you want to start us off with picks?

JONATHAN: Sure. We talked about a ton of tools today, so [inaudible] new tools this time and I’ve got two picks. One is a book by Michael Lewis called The Big Short which is about the banking crash in 2008. It is fascinating, it is horrifying and amazing that he was able to spin an interesting story out of a really confusing, just rat’s nest of yuck. Just numbers and – ugh, it’s wild.

So I listened to the audio book and big fan of that [inaudible]. It was really good and so0 I definitely recommend checking out The Big Short. It’s almost like a thriller but it’s a true story. And then I’m going to pick a self-promotional pick here. This morning as we’re recording this, I launched a book called Hourly Billing Is Nuts. I wanted to give the Freelancers’ Show audience a code for that which [inaudible] use – you can use any code I want like fs215. Is that crazy? We’ll go with that. FS215. So if you want to get 30% off my new book, you can go to hourlybillingisnuts.com and you can use fs215 to get 30% off.

CHUCK: How do you feel about hourly billing, Jonathan? [Chuckles]

JONATHAN: It’s a cancer on professional services and it is my mission in life to rid the earth of hourly billing. [Chuckles]

REUVEN: Let’s see if we’ll exchange your [inaudible] since I met you.

JONATHAN: [Chuckles] Got to be more clear.

CHUCK: Alright Philip, what are your picks?

PHILIP: Jonathan, did you know they made that book into a movie and the movie was also quite good.

JONATHAN: Yes. Hourly Billing Is Nuts – The Movie. [Chuckles]

CHUCK: How does that theme song go?

PHILIP: Somebody’s already bought the rights, huh? [Chuckles] Quick tool recommendation, I mentioned it during the show, Fantastical is a nice calendar app that I standardize on. It’s – people get religious about calendar apps. The thing I like about Fantastical is a natural language processing for adding new events. We just type in using plain English what is going to happen and it does a pretty good job of interpreting that and setting up all the parameters of a calendar event based on that.

The other thing it does that I mentioned is it lets you, at the click of a mouse, transpose your entire calendar into any other time zone which is awesome for people who work with clients who are all over the country or planet because if I’m curious what time my mentoring group meets in Germany, I can just transpose it into that time zone. That’s nice and it’s been pretty reliable. And it’s worth every penny of whatever they charge for it.

My second pick is if you are a – like I am, a fan of raunchy adolescent humor, this movie, The Brothers Grimsby is a must-watch. I watched it a couple of days ago and I’m still laughing about some of the absolutely disgusting, grossed out humor scenes. It’s a Sacha Baron Cohen production which, if you know what he gravitates towards in terms of his films, you know everything you need to know. It did not score that well in critic reviews but it was super hilarious.

If you need to laugh more like I do, maybe consider adding it to your list. That’s it.

CHUCK: Alright Reuven, what are your picks?

REUVEN: Okay. So my first pick is something I think I picked a long time ago on this show. So I do a lot of travelling; I’m [inaudible] vegetarian restaurants when possible, and so HappyCow – happycow.net, the website, and the app for your phone. Truly fantastic. I’ve been in numerous cities; I say to HappyCow, “Show me all the vegetarian restaurants and how far away they are,” and it will do that then I will [inaudible] with Google Maps or whatever. Definitely a fun little app, useful site and it does something simple and it does it well.

The other thing is I [inaudible] the last person who [inaudible] discovered, but it turns out The Office is a great show [chuckles] especially if you don’t work in one. I think I’m enjoying it for a different reason than most others. Most people watch the show and say, “Oh my god, this is exactly what my office is like. Thank goodness someone put this into a comedy.” I’m thinking, “Thank goodness, I don’t work in an office anymore and I can avoid this sort of nonsense.” But anyway, I am slowly but surely or probably not so slowly but surely going through the seasons and definitely enjoying it and relishing the fact that I don’t have to deal with a boss or other such things.

CHUCK: Are you watching the US version or the UK version?

REUVEN: The US version. Is the UK version better?

CHUCK: I haven’t watched the UK version but the US version I watched and I laughed my way through it. And my wife watch a couple of episodes with me and she’s like, “I don’t get it,” and I looked at her and I said, “I think it’s funny because I’ve worked with all of these people.”

REUVEN: [Chuckles] Right.

CHUCK: I had that boss. I’ve worked with all of these characters.

PHILIP: They’re both fantastic, both the US and UK versions.

CHUCK: Awesome.

REUVEN: And I guess I’ll also add to what Philip said which is not only The Big Short is a great book but the movie was terrific. And the fact that they were able to turn – you think the book is interesting? Michael Lewis is a gifted writer with fantastic stories, but you would think that it was already an amazing achievement turning such a dry subject into a great, interesting book. And it managed to turn a dry subject into a really great movie so [inaudible] for them.

CHUCK: Alright. So I’ve got a couple of picks. Last week, I was at podcast movement and while I was travelling, I was having some issues with the low bandwidth stuff on my laptop. And it turned out that I also just really wanted one so I bought an iPad Pro and I bought it with the smart keyboard and the Apple pencil. Why not, right? And it turns out that when you’re flying, if you’re using the web app with really low bandwidth or really bad connection, when you try and send an email or reply to somebody, it actually has to call back to the server in order to load up with the right information in the text box where you type. And if you’re using an app like the Gmail app on an iPad Pro, then it just works. You just get – you can watch it spin for a minute while it sends the email so I was super happy with that. It also got me touching the screen of my laptop while I was using it. Why isn’t this working? Oh, I can’t [inaudible] the screen on this thing. I really liked it.

The other thing I liked was with the Apple pencil. During some of the sessions, I could actually take notes by hand which for me is still a little bit faster and higher fidelity than typing just because I could draw the pictures, draw diagrams and arrows and all that stuff. I really liked it. The thing is I use an app – I think it was called GoodNote or GoodNotes. It’ll actually index your handwriting so you can do a text search on your hand written notes in it. That was also really nice because then I can just dig through it and go, “Okay, I’m looking for these kinds of factions that I can take. I’m looking for these kinds of ideas that I can just get a lot out of. I’m going to pick all that and we’ll go ahead and wrap up the show.

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