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Michael Shane began his career as a classical musician, and now he’s Director of Digital Strategy at Postlight. This week, Michael takes Paul and Rich on his journey from the orchestra to the land of tech. He shares what he’s learned along the way from what makes a great digital strategist to why strategy isn’t the same as sales — and gives tips on how to write a proposal that will win over any audience.


Michael Shane You know you can write WinNuke in one line of Perl. Google it. [Rich & Paul laugh] Anyway my— [music ramps up, plays alone, fades out] 

Paul Ford Rich, Rich, Rich, we’re back. 

Rich Ziade We’re back where Paul?

PF In the office couple days a week, you and me.

RZ Is that why you’re an ultra 8K resolution right now in front of me?

PF Incredibly high resolution. Yeah, no, and just vertically horizontally just very present. Yeah, it’s pretty exciting.

RZ In any case, speaking of 3d. Guess who’s here in 3d? 

PF Who’s here? 

RZ Michael Shane.

MS Hi, guys!

PF Michael Shane from Postlight. 

MS We’re in the same room. 

PF We are. The acoustics are pretty good, frankly.

RZ He is Director of Digital Strategy at Postlight.

PF That’s right. Michael joined us.

MS For a little bit. Yeah.

PF During the pandemic. 

RZ Yes. 

PF And now we’re now you’re here in the flesh. There’s also clients in the office. 

RZ What? 

PF Yeah, I know, it’s really exciting. Two clients are coming by today.

RZ I’m finding that people want to get the hell out of their house.

PF Oh, my God.

RZ I think that’s happening. 

PF Well, they want to work together and get their stuff done. They want to see people, they like to collaborate. It is what it is. 

RZ Michael, welcome to the podcast. 

PF Welcome to the podcast!

MS Thank you. 

RZ Wonderful to have you here.

MS A pleasure to be back. You know, it’s been four years since my last podcast appearance? 

PF That’s right, Michael was on four years ago as a client.

RZ Yes.

PF Relationships are complicated with agencies.

RZ It was a different, it was a collaboration. He was at Bloomberg at the time and actually less of a client. Bloomberg, I wish they would have been more generous with the fees. But it is what it is. [Michael laughs] But boy, was it fruitful. It was a great project. 

MS It’s one of my favourite things I’ve ever done.

RZ It was really cool. 

PF To be fair, we squeezed a good case study out of that.

RZ Boy did we.

PF We keep squeezing it. 

RZ No more juice left. [Rich laughs]

MS You had to take my quote off the website when you hired me!

PF We had Michael as an endorsement and we had to pull him because once they’re employed here, you can’t have them.

RZ This is true. This is true.

PF Anyway, so we didn’t actually and we never would, we don’t hire people directly from our clients. But Michael left Bloomberg, went to another agency, and is now with us. So, good to have you here. I mean, just so people understand. You’re Director of Digital Strategy. 

MS That’s right. 

PF Those are three words that mean absolutely nothing. So why don’t you tell people a little bit about what you do?

MS Sure. Absolutely. So, Strategy at Postlight exists to look after the health of our relationships with clients, and to be thoughtful about how the agency grows, how we operationalize the things that have intuitively gotten Postlight to the amazing place where it is today. We’re really there to work with clients to answer the big, gnarly, nasty questions that often come before product requirements. 

PF Well, I’ll give you an example would be a well actually, we did some work with the MTA. And when we went into the MTA, they were like, “We’re going to use this system. What do you think?” Where people come to us and they say things like, Hey, we want to build some CRM tools, should we use Salesforce? And we actually, strategy is in a funny way to me that the job of going “You could absolutely do that. But what does it mean?”

MS Yeah, let’s take a breath.

PF Yeah. Why? The strategy is just why over and over again.

RZ Yeah, and you know, strategy is, it’s one of those words. [Rich laughs]

PF Well it’s dangerous, everybody, everybody feels they should be a strategist.

RZ They do. And if you look at, you know, Postlight’s young history, the word strategy, we used to orbit entirely around product. In fact, product strategy, the word strategy lived inside of product in Postlight for the first I’d say three years, but if you strip it, of all other words, and just say, strategy, it’s advice.

PF Department of advice would be wonderful.

RZ It’s advice, ideally, devoid of your own interests as an agency, because my advice will always be well, obviously, you need the $10 million solution, not the $2 million version in front of you!

PF That’s right. That’s right.

RZ But people, their antennas are up anyway. So Michael, I want to ask you what you’re not.

MS I’m not a salesperson. 

RZ Oh, my God! That’s the question I was gonna ask!

PF Mmmm!

MS We don’t have a sales department here. 

RZ Explain that. 

MS Well, we just don’t. [Rich laughs] We don’t have business development. I have never had a sales job in my life. I mean, everybody in the Strategy Group at Postlight is essentially a practitioner.

PF Yeah, it’s almost a criticism when you say it, but it’s not right. It’s like—

MS No! It’s just how we do things here. It’s not a criticism at all!

PF We’re okay right? We’re a good company? [Paul laughs]

MS I mean, there’s this very delicate space that Postlight has managed to construct where I feel no pressure whatsoever to sell things or, or inflate things or make things expensive.

PF No, you don’t, you aren’t under that pressure.

MS Exactly. It just doesn’t exist. 

PF We will occasionally be like, “what if we charge more?”

MS Right but nonetheless, somehow still lots of businesses flows through the door just by virtue of us trying to be helpful.

PF The deal for sales at Postlight and the deal for how we grow is to just be helpful. That is like, this will be useful. Sometimes it’s a little disappointing and we try to avoid the situations and I feel we’re pretty good. We’ve gotten better at filtering out the ones where it’s like, “I’m gonna get 20 people to respond to my RFP, and then I’ll make the best decision based on how much they sing and dance” like unless we look for people, because it’s those are unwinnable situations.

RZ Well, I think it speaks to, and I would love to tell you this was part of the master plan. But it wasn’t. Maybe I should just start saying this was part of the master plan. 

PF Let’s imagine, let’s start acting like we’ve actually planned every single thing that’s ever happened the whole time.

RZ As we thought about what Postlight wanted to be when it grows up, there was “I’m going to fulfill your needs that you are very explicit about.” And then there is “I want to hear about what you’re struggling with and help you craft what you need.” Right. And that distinction, I think, has defined Postlight, because there are plenty of services companies out in the world that are fulfilling needs, right? And we play, I’m not going to say we’re too arrogant, and we don’t want to go and compete in those arenas. We do. We respond to RFPs sometimes.

MS We get lots of briefs that are very prescriptive. 

RZ Very prescriptive.

MS With that they think they need.

RZ And we don’t toss them aside. Definitely not. But we we have put enormous energy into cultivating an outreach culture that is driven by dialogue, conversation, generosity, I mean—

MS We’re insanely generous. Can I just say that? 

RZ Are we?

PF Yeah, cuz I mean, you’re coming from another world. So we just, we’ve just figured, for me, I always feel bad that money is even in the picture. 

RZ Oh lord. 

PF I feel that in a just—

RZ CEO, comma, Postlight. Here we go.

PF In a just society—you know what broke my heart? There’s a not for profit transit oriented organization. I just think it’s great. Like, you know, let’s all ride bikes kind of place came by and they had $42. And I’m like, I just want to help you!

RZ Paul Ford on the earnings call.

PF Oh it’s terrible.

RZ Not good. [Michael laughs]

PF If we’re ever public. [Rich laughs]

RZ Listen. Listen, guys. It was a really hot summer this year. 

PF I want to give you some guidance. We landed over 200 projects valued at $44 each. [Rich laughs]

MS It felt really great. 

PF But luckily, Rich is here.

RZ Yeah. Explain generosity. Explain what you mean by that.

MS We put a nonzero amount of effort in trying to help every legitimate inquiry that comes to us, get some kind of benefit of having gotten in contact.

PF Everybody leaves with something valuable. We actually, we have, we keep trying to build the list of other agencies that we think are good that we can send people to a smaller shop.

MS And to be clear, like you said, we’re protective of our time, we’re conscientious but like life is too short, to not be nice to people.

PF The job of growth at Postlight is to always be making friends. That’s it, like not just like, not networking, making friends by being helpful.

MS Because why not? 

PF That’s it! You know how hard that is to communicate to the world? Like, it’s just everyone just assumes it’s predatory capitalism. Like that we wake up—

RZ It’s also a longer game. 

PF It is.

RZ Because it may not come through for whatever reasons, budget or whatever. But there is an impression that’s left there. And people have colleagues and people are in the industry. And people are, have lines and those things bear fruit later on. And we’ve seen it.

MS We’re working with a client right now that first talked to us something like two years ago, and it wasn’t a fit for budget reasons, because we have to keep the lights on, but now they’re here and they’re working with us on something else. And it’s great. 

PF Just being helpful, feels wrong, right? Like in a lot of orgs. I think like who are you giving your time to? What are you doing? How are you using it? But you actually don’t have to do that much more in order to get the business. As long as you can do the work. You have to be able to do the work on the other side.

MS Well, it’s easy to give people permission to do that when you sort of set your business up to be about outcomes and not about hours in a spreadsheet. 

PF That’s right.

RZ So to clarify that. I mean, we are not about logging hours. 

PF Yeah, we don’t have any time cards, never did. 

RZ We never have had time cards at Postlight. We’re proud of that fact. It speaks to the kind of culture we’ve cultivated within the company across the disciplines, right. I think we’re giving you know it through all this chatter, a really good piece of advice, which is if you want sincerity, as you reach out to people out in the world—

PF Well you got to pay a lot of money for that.

RZ That’s tier one.

MS It’s a very, extremely scarce resource.

PF You know, sincerity is just like woof, boy, that’s a premium.

RZ I admire salespeople. I’ll tell you why. When you meet someone at a party or in a bar, and they say I’m in sales, it’s just laid bare. They’re not hiding it. I’m here to take money from you for this thing I’m trying to get you to buy. And I actually, I envy that a little bit because we’ve gone to such great lengths here to A) not create that environment where you are that exposed and sort of very blatant about what you’re doing. Obviously, we’re a successful, profitable agency. But we’ve nurtured strategists, not out of a culture of sales, but out of a culture of practitioners.

MS Well, you said one word Paul and you said one word Rich. They both start with C, Paul said the word capitalism. And rich said the word culture, right?

RZ That’s how it’s supposed to go. That’s how it’s supposed to go! [Rich laughs] Finally! Finally!

PF I lost it!

RZ Paul, tell me about capitalism. 

PF It’s your company now. You know what? I actually just wrote about this for Wired. I figured capitalism out. 

RZ Oh, you did? 

PF Yeah I did. You ready?

RZ Yeah. 

PF It’s about money. [Michael laughs]

MS No, this is the hard part. And I tell this to everyone who interviews and has never worked at an agency before. I tell it to friends and family who asked about what I do, because as we mentioned, job titles at agencies mean very little. Working at an agency can be hard, because essentially, our job is to commoditize and merchandise, creative work. It’s hard.

PF They’re all mercenary. We aren’t aligned with your mission, we’re aligned with our own.

MS And at the end of the day, accountants have to accountant. And rent has to be paid and salaries have to be paid. But that’s why the other C word culture exists. And the culture that you build from the inside is 100% what clients or prospective clients or friends are going to experience sure outside and it starts there.

PF That can align right? And so you know, what’s critical with what you’re talking about, and why we don’t have like a salesy sales culture. Well, first of all, the only people who really thrive here tend to be people who are genuinely excited about the subject. Like, you can sit there and show Rich or I you, Michael, a piece of software as a service, you know, software as a service platform and be like, I think this and the other and we are genuinely interested, like not like, okay, it’s my job to be interested. But like, what did you get up to? Oh, my God, what platform did you build this on? Where are you? Who’s using it? For whatever defect of my personality, I kind of can’t get enough of that. I just want to understand how that world works. And I think like when people feel that enthusiasm on the other side, and they they realize after a couple conversations, that it’s genuine, I wasn’t just putting them on. And we want to know how it all works. They realize we can connect at that level. And so like, that is very different. Because it’s it’s a lot different than like, “I’m going to tell you about the future of the digital, you know, which is that everything is going to be moving at a higher velocity. And you’re going to get left behind.”

MS Innovation!

PF Yeah. Exactly and we barely say the word innovation.

MS I have not said the word innovation professionally since I started working here.

PF No, and you don’t have to.

MS I mean, literally.

PF No, no craft and discipline, and we’ll get you a really good thing.

RZ Yeah. I mean, it’s a ton of listening early on. And that first meeting I’m doing, you know, the team is growing now. And we’re—

PF That’s a lesson I learned from you. Because I used to come in and be like, I got to convince them I’m okay. And then it’s actually, all they need to know is that they’re heard, like, that’s the start of the relationship.

RZ And it’s what I need, because I am constructing a reaction to the current setting that we’re in, that they’re in, the circumstance. And I don’t know that yet. And it turns out, people love to tell you what they’re going through. 

MS They just want to be heard!

RZ They just want to be heard, right?

PF Nobody’s calling us because it’s all going incredibly well the way they wanted to. They’re calling because they want to do something different.

RZ Michael, let me ask you this. We don’t have a big sales gong. You know, when you land the deals.

MS There’s no gong. 

PF There’s no gong so far. [Rich laughs]

RZ It’ll be digital, it’ll be a bot.

PF This firm is growing, our culture is changing. And there might be a time for a gong.

RZ This has been all very mushy, this conversation has been very touchy, feely, it’s been about culture. So like success metrics, echo effect, right? How do I know you’re doing well, and you’re a leader at Postlight. And you have teams that are out there servicing these clients. How do they know they’re doing well? It’s one of the things that I think we’ve had to work on is to build that bridge between the interface team, the Strategy Team, and the teams that are delivering the goods, right? So talk to me about—

PF Work in progress. Work in progress. That is something we work on.

RZ Yeah, it is something we work on, and it takes work. React to that, I guess, what is success for you? And how do you convey success to others? 

MS Sure. So when we’re talking about projects that are up and running, where we’re working with clients, the ideal situation to me ongoing success is when our team and the team of people that we’re working with at the client are sort of mirroring each other emotionally, spiritually, intellectually, as in, are we the same level of stressed or concerned? Are we the same level of happy, excited, hopeful, whatever it might be? 

RZ They’re aligned.

MS They’re aligned. When things are misaligned, or things are wildly different, even if—

RZ Adversarial, yeah.

MS You’ve got problems. Because then you have surprises. And there are always surprises in client service work. 

PF Sure.

RZ Who’s fault is it when a surprise kicks in between a vendor and a client? Always. Always. [Michael laughs]

MS I mean, it’s quite an implication there. [Rich laughs]

PF No no. It’s the vendors fault. 

MS Yes. 

PF Yeah. It’s the vendor. 

RZ When in doubt. And that’s what they pay for.

MS That’s right! I mean, we are in a client service business. And that’s cool! That’s, that’s what we’re here to do. Like, yes, we make great software, we ship great software. But it is all part of collaborating with clients to help them do the things that they want to do. 

PF And I mean, Rich, you and I are, I’m the CEO, you’re the President, you’re never done right? There are times when I am explaining things to a client, and they look at me and they go, “I just don’t know why we would do that” [Rich laughs] And I realize I’m going to be crawling up the mountain for the next six hours.

MS Well, that’s part of the reason we don’t have a sales team, right? Even when we get a brief that is totally prescriptive in terms of product requirements. And maybe they the client has done great research and diligence. And that’s the thing that should be built. And so we’re gonna go and we’re gonna help them build it. Great products change organizations, when they’re new. You bring a new product or a new capability into an organization, all of a sudden, they realize, oh, crap, we need this data and analytics person to really understand if we’re succeeding or not, we need this kind of technology to really take the next step. And so even if we start with an engagement that is extremely prescriptive, that’s how we grow. We grow because when we do our jobs right, the things that we make with our clients, change their organizations, and so on and so forth.

RZ Building goodwill. I want to share another observation about Postlight that is a point of pride. I’ve always been a believer that the business of like the Foresters and the Gartner’s of the world is to seed anxiety. 

PF Oh, sure. But that’s the job of the media. That’s the job of like, most 90% of what is produced in the world in terms of words, music, pictures, and business communication is just there to make you feel bad. 

MS I don’t want to get too radical, but like, literally, capitalism exists to keep you and keep us all uncomfortable. 

RZ God I wallow in that discomfort though. [Rich laughs]

PF Yeah, that’s the thing.

MS Discomfort breeds commerce. 

RZ Title of the podcast!

MS Don’t get me wrong! I love money! But yeah, let’s be real. And that’s the tension.

PF You have to be broken to thrive in this in this world. That’s true.

RZ It taps into personal ambition and taps into aspiration. I don’t think we need to apologize for it. I think we are hopeful beings and I think capitalism is a way to keep score that. So first off, I represent culture at Postlight, the CEO probably has more to say about the capitalist side of things.

PF It’s about money. [Michael & Rich laugh] 

RZ We tend to bring like, we don’t wag the finger and say, “well, you’re not on top of Internet of Things” we actually tend to bring the temperature down. A lot of people are like, hey, you’re behind here, you need to get these six initiatives going. And if you don’t, then everybody else is going to talk to their Alexa and your service won’t work with it. 

PF Well you know what it is? People love innovation, and they love to bundle it up. And they like to buy it because it doesn’t require any commitment. And then you look at who succeeds. And it’s, we needed a new CRM, and we rolled out a good CRM solution.

MS We consolidated four legacy systems.

PF Now and what it all comes down to over and over and over again, is we enhanced our ability to communicate and collaborate in a way that lets us make better decisions more quickly.

RZ That is not what Gartner’s writing about right now. Because it’s boring.

PF No, of course, they’re writing about Cloud Service integration partners. And you know, I’m going to do that—people would much rather make things out of Legos then talk to their neighbor. 

RZ This is true.

PF It is true right? One of the services the agencies provide and in especially management consultant types of stuff is they will go talk to the neighbor, they’ll go talk to all the people on the floor, who you really can’t make eye contact with after five years for whatever reason, and they’ll just be like, well, you know—

RZ We’ll talk for months. 

PF Oh, marketing needs this and you know, ops needs this. You’re gonna have to reorg over here and they will have the difficult conversations for you.

MS So many billable hours. 

PF That’s right! Well actually talk a little bit about, you don’t have a traditional consulting background.

MS Thank god. [Rich & Paul laugh] No offence! Sorry. 

RZ It’s why you’re here. 

MS I went to music school. I’ve already had a career as a classical musician. Playing in orchestras. I was a clarinet player.

PF Aw man, you should have brought it in!

RZ Yeah, we could’ve kicked off the podcast with a smooth—

MS Not for my first first visit as an employee. Maybe next one.

PF God, Postlight talent show is ruined. Like and here’s Michael a professional classical clarinetist.

MS Yeah, but yes, classical music but before that, when I was you know, young, I taught myself HTML. I tried to write a personal banking app in Perl, failed miserably. I’ve always loved technology. Yeah, but so while I was in music school, my first job job was working for Apple Retail. Right? Apple Retail, no commissions, never has been, never will be. And that was really my first exposure to customer service while being incentivized in the right way. I mean, it sounds really wishy washy.

PF No but come on in and buy an iMac. Were these like the candy colored ones? The big plastic ones?

MS This was right after that.

PF One generation after. The lampshade?

MS I started—no, after that. I started in 2006, the year before the iPhone came out.

PF Okay okay.

MS And I learned things there like assume positive intent that served me to this day, I learned that on my first day there and I use it every single day. And the whole culture of selling quote unquote “selling” at Apple was you need to become an expert in everything Apple so that if someone comes in and said, You know, I love taking pictures of my grandkids, I love sharing them with my family, you can walk up to a computer and you can show them how they can do all of this in one place. From a place of knowledge as a practitioner. 

PF So become a good practitioner with the products.

MS And everything takes care of itself. 

PF You communicate how the products work, you’ve now completed the transaction.

MS That’s it. Care about the outcome for the person who’s standing in front of you.

PF Did you get a discount? 

MS Yes.

PF Okay, well, actually, it’s kind of cool. I wish Postlight could get a discount on frickin Apple products. 

MS So, so my background is weird as my career in classical music went down, that’s when I met Josh Topolsky and accidentally found myself working in digital publishing in 2011 when things really started to blow up. Vox media, The Verge, I was sort of at the very beginning of The Verge. Happy 10th anniversary later this year.

RZ One of the things you’re saying is you don’t need the log the three to five years in that particular profession, to go towards digital strategy.

MS No, to be a good strategist, you have to be a good learner. I’m really good at learning things.

PF First of all, I think the good learners are the people who are comfortable with the fact that they don’t know anything. 

RZ Humility.

PF It’s actually a big part of it. And then you have to be relatively positive about that so that people are comfortable. Like, I’m not an expert, but I’m really good at these things. So let’s bring these worlds together.

MS I’ve spent a tremendous amount of my life in a room alone being bad at things until I get really, really good at them.

RZ That motivates you. 

MS I mean, it motivates me, it has sort of shaped the way I see myself, at least, in the world. I mean, the beginning of every single project or every proposal, you have to become an expert in the industry, the client, that particular technology that you’re dealing with.

PF There’s actually a great book, Ogilvy on Advertising by David Ogilvy, and it’s go learn everything you can about the client, go figure out everything. And again, if you have that positive enthusiasm, it’s actually really fun. Because to me, the agency, the part about agencies, a lot of people don’t like agencies for reasons I understand. But I love being thrown into yet another banana cakes part of capitalism. And then you realize, you know, nothing. You’re like, Oh, this is how it actually works. I learned on Twitter that this was something different. But actually, it turns out that there’s a pipeline that animal fats go through.

MS I mean, the shortest description of my job, I think is one, develop expertise. Two, apply creativity and prior experience. Three, open a seltzer. That’s the job.

RZ I’m going to add a four. I think you have you have a trait that I think many don’t, which is there’s a humility and a positivity that you’re bringing. People love to teach you about what they’re experts at.

PF Oh, God, yeah.

RZ They love to tell you about it, and they want to educate you on it.

MS Because they want you to care about what they care about. 

RZ They want you to care about what they care about.

MS They’re just looking for connection, man!

RZ Well, it’s also like, I’m here, because I have a problem. People come to Postlight because they have a problem. But you’re gonna give me the first 15 minutes to tell you about what I’ve achieved and my expertise. Before I tell you about the problem. You are now building something bigger, that transcends the project.

PF Well, let’s now let’s play out how that would actually go. Right. So let’s say let’s be the bad salespeople, you walk in, and you say, “I have a new insurance product I want to build I don’t know if my company’s really down with this. And but I’ve been actually told by the CEO to go get it done. And it needs to work on mobile, and it’s gonna do five different things” right? Now, I know this about you, and you walk in the door. And if my first 15 minutes are telling you how great I am, you’re gonna, it’s not even that you’ll get turned off, you’re just gonna be bored. Because that’s not why you’re here. You’re not here to find out that you’ve already gone to the effort to walk in.

RZ I’m in the room. 

PF Yep. So the only real function of being in the room is that we’re going to turn around your inner space. It’s actually where we have the most power and control. And we’re saying come on in here because these are where the tools are. And this is where the things are to help you solve your problem. First of all, we need to understand your problem. Being in a situation active note taker, actually, to me is one of the most important things I can do to signal listening like I loved it. You know, for a while I just used graph paper eventually went to an iPad.

RZ I notice that, you’re a scribbler, even when you’re thinking and you’re and I looked down and I just see like, you know.

PF I got that reMarkable 2, reMarkable 2 is really good.

RZ Product plug! reMarkable 2, I have one of those. They are fun.

MS Do you guys have a promo code? Just kidding.

PF No, I wish I did.

RZ I want to, I wanted to zoom in on one of the things you said, which is, you’re listening not only to the problem, what I like to do is I also want to hear about what they’re good at, like, what is going well, I want to understand their world. I don’t want to just understand the problem space that they’ve come to us with right?

MS You can’t help them if you can also understand what’s what success looks like in this world, not only in the industry, but in their organization. You can’t focus only on the calamity.

RZ So I mean, I’m gonna make an assumption here. And you correct Tell me if I’m overreaching? Like you’re talking about very particular soft skills. Obviously, a love of tech and appreciation for what can be achieved is really cool. But anybody can do this. I mean, if you—

MS You have to have a set of passions that can keep you interested in excited for at least for 40 hours a week while you’re doing the work. 

RZ Do you have to like people?

MS I think you have, I mean—

PF You gotta like people.

MS You gotta like people. I’m a little bit as I’ve gotten older, I’m in my I’m entering my late 30s, I think I’ve become more introverted over time. But you know, and I sometimes like to exaggerate the extent to which I’m a misanthrope, but generally, yeah, I like people. 

PF I like seeing what people get up to, you know, what this does raise this is what we’ve been talking about more and more as we grow. People worry a lot about like, you know, if the monster party of governance came in and was like, we need you to raise more monsters from the deep, would we take that work? And it’s like, you know, we’re open for business. And we have a lot of different kinds of people here. But ultimately, if there’s not like a kind of values alignment, we’re not going to be in a position where we can really help you out. 

MS Yeah, definitely. 

PF So it’s like, no, probably not. And those kind of they naturally fade away, it’s actually less of a there’s less filter that you need, then you’d think in terms of business ethics, if you communicate outward in a certain way.

MS Rich, let me put it this way, there is no General Assembly course for what I do. 

PF That’s a good brag. I’m gonna say that.

RZ And there never will be!

PF Let me tell you, no flat iron school, nothing.

MS But look, even if you go and you take the product management course at General Assembly or whatever, that’s not going to prepare you to be a product manager here, right? Or I think at any good agency. Being a product manager in house where you own one slice of one product in micro for like three years. And your job is to move the needle one basis point. That’s different than Product Management at an agency or the product owner or leader at an agency.

RZ To help the the audience here, you took a leap, you’re using product management interchangeably with with digital strategy.

MS Well, they’re they’re very related, especially here if I was slight, right, but yeah, digital strategy, Product Management, Product Management, they mean different things to different places. And I guess the point I’m making is that if you want to be good at anything approximating either of them in an agency setting, at least, your run of the mill product management course, yes. A nice little add on, right, but you absolutely don’t need it, right. You know, a lot of the smartest people I know with the title, Product Strategist or something like that have widely varying backgrounds. Because you’re looking for markers of curiosity, creativity, personality, personality, the ability to sort of generate velocity for yourself and for a team. Sure. Let’s put it this way. I’ve been working in agencies for, I guess, the last four years or so. I have not written a single JIRA ticket. Ever.

RZ Nothing against people who write JIRA tickets.

MS Nothing again that! Just to be clear. Yeah, I’ve just focused on different things and lots of our product managers at Postlight because we ship so often, yes, there are tickets being written and tickets being moved. And that’s a critical part of the job. Anybody can learn to do that.

PF What makes a good proposal? 

MS Ohhh.

PF Because this is I mean, a lot of our work. Yeah, you took a lot of work off of Rich and me, that’s worth noting, and off of Gina and Chris.

MS You’re welcome. 

PF Thank you, you know, we are appreciative. You took a lot of work on taking and writing the proposals and communicating with clients in the early days of the relationship, right. So you create a lot of artifacts when you do that. What makes a good proposal in your head?

MS There’s a couple of different categories. Let’s start with the easy stuff. First, the easy stuff is that it has to be polished. You know, we’re a New York City agency. By and large, right, we’ve always had at least a third of the company remote, but like, we have New York City overhead, we’re expensive, we’re world class, and every single thing that leaves the door and is going to be put in front of a client or a prospective client or a friend has to look up to snuff it has to match what we strive to do here.

RZ I always say it has to feel expensive.

MS Polish is about removing distraction. Let me use a music analogy here. When I listen to an orchestra or a soloist or something, if they’re not playing in tune, which can mean many different things, but let’s keep it simple, but if they’re not playing in tune, game over, I’m out. Because sure I cannot get to whatever it is they trying to tell me, they can’t meet a baseline level of quality and competency. And so a good proposal out of the gate has to have no distractions from the story that it is trying to deliver to you. Because ultimately, that’s the other side of it. 

PF So we’re telling a quality story. And so this thing needs to look and feel quality right away.

MS Right, so that it gets out of its own way, so that you can be as efficient as possible in your storytelling. And then the other side of it is you have to demonstrate very quickly and succinctly and forcefully that you have not only read the brief, but that you understand the problem, which means you have to go beyond the surface layer, you have to say I’ve listened to you, we’ve been on the phone, we’ve had meetings.

RZ Don’t just regurgitate.

MS Exactly, I’ve read your RFP, I’ve listened to what you’ve told me. But here are the implications of what you’re telling me, here’s how we understand what’s going on. And therefore this is where we would begin. And this is why and then you go from there,  you have to go beyond the surface level.

RZ We go to great lengths to actually restate in our own words, what they’re struggling with. 

PF I mean, the way I think about this is unless you’re drawing the platform that they’re going to build and like unless they can see that you’ve internalized that and turned it into your world, you’re you probably haven’t gone far enough. You should be able to if somebody asked you something, you should be able to say, here are the pieces of the solution, not how every single thing is going to work. You’re not going to do the work for them. But like, this is how we’re going to approach it. Yeah, these are the boxes. Here’s the components.

MS I would also say and I’m gonna go out on a limb a little bit here. Hopefully, none of our clients end up proving me wrong, but I think a good proposal should contain at least one thing in there that surprises the reader. That they didn’t know. An insight about their business, about their industry.

RZ Interesting.

MS A different way of looking at their problem.

PF I love a good fun fact. I used to literally put Fun Fact colon into proposals with cool imagery. 

RZ Yeah, an aside, just like dry—

MS That’s, that’s another good point. A good proposal should also connote enthusiasm. Otherwise, it’s an invoice in advance. You know what I mean?

RZ We love invoices! Have you met our CEO?

PF He’s such a capitalist. That is really true, which is that most people are so working backwards from that number with such intensity, that they forget that they forget the conversational aspect and maybe layered it. And that is the difference between like, the serious, long term consulting partner.

MS If we’ve done our job as generous consultative potential friend, collaborators, then they already know, our clients already know the ballpark of price that they’re headed towards. Yeah, that’s the lat it’s literally the last thing on our proposals, which I think is probably pretty common. But by the time we send the proposal, assuming it’s not a highly procurement driven RFP, or something like that, if we had been able to have a relationship with them, they know what’s coming with the cost. The proposal is what makes the cost an after thought.

PF You know, it’s weird. RFPs are really tricky, because you do have to reply to them. You do have to take them very seriously. But there’s also there’s a rule in government, especially, which is who’s gonna win the work? Well, who wrote the RFP, right? Like it’s they bring people in to consult those people write the RFP, and then they get awarded the work after going out, We’ve been on both sides of that. And like, when we are told, and this happens, like where we’ve issued a request for proposals, and then you’re like, I’d love to talk to you. And then I would talk now can do no talk. It’s like that dog and the meme, or it’s just like, no, no talk, only reply.

RZ We’ve had clients say, “You’re great. We love you. Goodbye” for a while. [Rich laughs] Yeah, we have to go silent now to let the process play out, which is I get it, I totally get it.

PF If there is no conversation, it’s awfully hard to get the work.

MS Those are the least fun proposals to work on. When you are not allowed to build a relationship.

RZ Sometimes they don’t respond, we’re not talking to anyone. We’re keeping it vague. You know, you’re moving forward. If after you’ve set the proposal, like, you know what, let’s chat.

PF I will say we just received a an RFP from a large, a not for profit related to kind of government stuff, just a really nice organization. And it was the nicest letter. They’re just like, here’s the budget.

MS Fantastic. 

PF It was one of the best I’ve ever seen.

MS Lots of clapping on our end.

PF Oh, it was so good. Because it was just like, here’s what we got. It’s not even the highest budget, but it was just like, Okay, this is very clear. That’s our max, this is where we’d like to go, this is what we’d like to do. We’re here. Now, here’s what success would look like, here are the risks from previous projects.

RZ That’s rare.

PF Oh my god, I just wanted to hug him, ready to do it for free.

RZ Well, you’re the CEO, keep in mind who you are and what you represent.

MS That brief came in and we read it, we’re like, wow, I really want to work with these people. And just like the proposals, the budget is at the end of the brief, and people were saying, oh, this, this is great. This is great. We got to do this. Before the budget number was even on the screen.

PF The number one tell actually is when they say they’ll send it to you like June 7th, and they’re like responses are due May 25th. Yeah, you didn’t get it together and now they’re now there’s gonna be the update about what to actually due. And you reply like, it seems like it’s May 25th, but it is June 7th today.

MS I checked in with the space time continuum.

PF I love how a good conversation about proposals turned into complaints about RFPs, which is very real.

RZ This is great. Just nuggets. Like a basket of nuggets of advice that’s been put forward. I think it’s the Paul and Michael show going forward.

MS Nahhh! [Rich laughs]

PF No, no, it’s fun to have you on and it’s you’ve you have taken on a part of this org. It’s pretty cool. 

MS I’m really happy to be here. 

PF Well, we’re learning we’re learning to give up control and it’s pretty exciting for us too. are

RZ We are aggressively hiring towards all the ways until the end of time. 

PF It’s true. If you think Michael be a nice person to work alongside. Great time to get in touch with Postlight.

RZ If you don’t call yourself a digital strategist and this conversation resonates for you and you think you carry a lot of those qualities. We’d love to talk to you. Michael, thank you for coming on. This was great. 

MS Can’t wait to come back. 

PF Oh, woof, see, good sales. Can you guys get your calendars out? Let’s schedule the next one.

RZ Check us out

MS Guys, what are the next steps here?  [Rich laughs]

RZ What’s the follow up? 

PF We’re gonna be back in touch with you in about a week!

RZ Reach out. We love to talk. I mean, you’ve just heard it through this whole podcast. We’re very generous and we love to give advice. 

PF We’re like angels.

RZ Just angels that also send invoices. [Paul and Michael laugh] Hit us up at 

MS That’s the title! Angels Who Send Invoices. That’s the title.

PF Good work, everybody. 

RZ Have a lovely week everyone.

MS Thanks guys. 

PF Bye! Back to work in the office. [music ramps up, plays alone, ends]