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We recently launched a huge project with New York’s public transit system, The MTA. Like the transit system the project was big and complex. This week we are joined by Product Manager Jojo Giltsoff who kept the MTA project running smoothly. She shares her tips and tools for managing big and busy teams and projects. She also teaches us how to find a healthy balance between being hypercritical and being an advocate for your team and explains why you should be writing down all the positive things people say about you. 


Rich Ziade People trust attractive things. [Jojo laughs] Don’t take that out of context. 

Paul Ford That’s why you and I are such effective salespeople. [music ramps up, plays alone for 14 seconds, fades out]

PF Rich!

RZ Paul, how are you?

PF I am doing quite well. Thank you for asking. So today is a good day because we have someone who isn’t you and me on the podcast. A gift to our listeners. 

RZ Well, it’s in addition to you and me, Paul, I think we’re great. I think this is a really good podcast. If you have a moment. Give us five stars on Apple Podcasts. I think that would be great. Write a review. 

PF God, is that still a thing? Is that what it’s called? It’s not called iTunes anyone?

RZ I think we’re still five stars, I think, I don’t know for sure. I haven’t looked in a while because I’m not as ego driven as you are. But I think we’re still five stars. But this isn’t about us, Paul.

PF No, it sure isn’t. Well, it is but it isn’t. So look, we have a very large project you’re you’re closer to it than I am on a day to day basis working for the Mass Transit Authority. 

RZ Yes, which is for the non New Yorkers. It’s the biggest transit system in the world. 

PF It’s the subway. It’s the buses. It’s a lot of other things too.  

RZ It’s the subway and the buses. It’s an amazing project, you can actually get the backstory at, and we have one of the leaders on the project Jojo, a product manager at Postlight with us on the podcast. Hello, Jojo, welcome to the Postlight Podcast. 

Jojo Glitsoff Hi, thanks for having me.

RZ I just want to say this statement out loud. The best product managers manage chaos very well. [Jojo laughs] Chaos comes from a bug that was unexpected. But most of the time chaos comes from humans, whether it be in a meeting with stakeholders or with designers or engineers. And so Jojo has A) wonderful ability a to make you feel like there is less money than there actually is, which is a skill, and also bring order. And that’s a big deal. And we want to talk with Jojo today about I guess some of the things she does that helps her do her job well. The proof is in the pudding. Do people still say that? The proof is in the pudding?

JG Yeah, definitely, especially as a British person like puddings a big deal. [Rich & Paul laugh]

PF He set that up for you beautifully. Really. 

RZ I really, I didn’t even mean it. But here we are. 

PF He didn’t know what he was doing. 

RZ I didn’t know what I was doing there. What I mean by proof is in the pudding is that it is a big, big success story for the MTA. And for us, it’s the we built the communication platform that allows the MTA to talk to its riders and talk to its customers all across New York City, Long Island and the tri-state area.

PF I’m a little more distanced from from this project on the daily basis as I said, I will, I’m going to make an observation about Jojo because it’s key for what we’re about to talk to. As a communicator, Jojo is essentially fearless. Like she looks you in the eye. And she says, What do you mean by that? And it’s very non confrontational, but also like, it’s kind of on you to get a little clarity into the room. And boy, is that a power tool? Because it’s not that it’s even disarming. It’s just sort of like, oh, okay, there’s not enough clarity, and it’s on me to provide it. And that’s a very fair thing to do. Right. But I think a lot of times when people are confused, or when there’s not clarity in the room, everybody just kind of keeps driving forward, because they don’t want to look like the person who doesn’t understand and what do you mean by that? What were you know, just sort of like a where’s that coming?

RZ Break it down for me. Yeah.

PF I think, advocate of clarity. And that is her talking to you looking looking in the eye. And then there’s a piece wrote for the Insight section on our website. And it’s called Level Ip by Writing Things Down, and I want her to talk about it and sort of what motivated her to write it. But there’s a really interesting moment as we’re growing and what I’m seeing more and more is we have to write more things down as a small firm you can communicate person to person you and I most of what we do is still talking, Rich, when we’re talking about the company, we’re literally speaking what we’re thinking. And yet more and more as the company grows, I’m writing one pager is everybody’s writing things down. And so Jojo, as you’re opening this piece, like you realized when you got on the MTA project that you were going to need some new communication skills. So I think walk us through what you learned and sort of the steps you had to take.

JG Yeah, that’s super accurate. Before I was at Postlight, I have managed teams of like three people and I’ve managed teams of 45 people, like it’s been a huge breath of like different team sizes. But there’s just some things that don’t scale when there’s more than four or five people working on a project. You have to share information, you have to over communicate, you have to celebrate people because especially on a big team, it’s very easy for people to get lost in their like exceptional work that they’re doing because they’re always providing they’re always building and they’re just like on to the next thing. They’re not even like basking in the glory of having built something fantastic. They are, you know, they’re focused on the next PR. They’re focused on the next design. So what I found when I joined the MTA team, I was like, Oh, this is a bunch of people and like a bunch of really smart people. I can’t, I can’t let us down by not communicating well, I’ve got to make sure that people have the information that they need, and that they know where they can turn to if they don’t have the information they need and be super approachable in that respect.

RZ So it’s worth framing for those that don’t know how big was the team and what was the team made up of?

JG At the largest point, at one point in time, we had 12 engineers on the project, three to four designers in the project. An engagement lead, myself and Chris LoSacco has recently been another podcast. So you know, 17 folks at one point.

RZ Big team.

JG Big, fast, project. 

RZ Okay. So how did you get your arms around this thing and how do you keep it moving forward?

JG Some of its really like kind of low level in terms of you need to write minutes and you need to write agendas, and you need to make sure that you have the right people in the room because with a team of 17, you can’t get everyone in the same room even when we had all of the folks at Postlight for remotes team week, and we could only fit in the largest space at Postlight because there’s so many of us, we can’t all be there and chat because like things get siloed and calendars get tricky. And time zones, particularly,people are busy. You need to be communicating.

RZ You’re essentially the information conduit in a lot of ways. You had a meeting with a with a team of five, you know, so participants one through five are in that meeting. And then participants six, eight and 10 also need to hear about the outcomes of that meeting, is that, how do you relay that across? Right? I mean, there’s, you know, obviously Slack and stuff but walk us through what you felt responsible for in terms of being this conduit of information. 

JG I think at the beginning like we were in a lot of very like product, heavy conversations with a lot of key stakeholders, both internally MTA, at different agencies. But also internally at Postlight to be like, you know, head of engineering head of design head of product really trying to get our arms around it. And with such an overarching project, writing things down in terms of like simply being like these were who was here. This is like the bare bones of what we chatted about. And this was the outcome, because things were changing so much that it was very easy for a stakeholder to come back and be like, well, I wasn’t part of that meeting, and we’d be able to be like, actually, you were, or like, actually, no, you missed this. Here’s the minutes, here’s what we discussed. Can I talk to you about, like how I can get you involved in this?

PF You know, there’s a thing going on here that’s really interesting, which is if you go look at this piece, this is something as a tech firm, right? We talk and think a lot about tools. And if you skim this thing, you’re gonna see that it’s talking about Slack, and it’s talking about Whimsical, which is a diagramming tool and things like that. Right. But the key skill, the key thing you said is we took minutes during the meetings, which is basically a technology that I’m assuming was created around the year 1300. Okay, just, you know, it’s, it’s been with us for a while that you would write down things that people say when there are lots of people talking and that would, and there’s a reason minutes exist, it turns out, it’s this, you can’t really get consensus unless you have a record. So like, it’s not the most intense new, like, there’s no magical feature of a product that saw this for you. It’s just a lot of active listening and writing things down.

JG Yeah, I think the act of listening is is crucial in this. You know, it’s not just the things that people are outright saying. It’s the things that people aren’t saying, there’s so much that you get from the tone of voice, the way that people are in the room, even when we’re virtually in the room. You can sort of allude to in minutes and say like this was discussed, this was discussed. You know, Chris feels like this, Matt feels like this. It doesn’t need to be hyper specific, but like just giving an essential overview of what the conclusion was allows us to be able to move forward and communicate to people who weren’t in the room.

RZ This is I mean, you’re bringing up a great point here around, and I’ve seen you do this, I’ve been in meetings with you. And I do this as well. And that is probing and steering to tease out information from people, right? Having notes is nice. But if you leave it to the winds of those that are not thinking about steering the product, they’re just notes, right? I happen to be a product manager that is constantly thinking about gaps. All I see are empty spaces. When I think about a product, I think about why have we not thought about this thing. And I come in, and it’s frankly, demoralizing. I come in with an accusatory tone sometimes, because I’m just paranoid about what hasn’t been thought about what hasn’t been accounted for. That’s a true, that’s a skill. That’s hard. You could write a book about right being able to see where those gaps are, especially when you’ve got stakeholders that don’t fully appreciate the technical aspects, the design aspects and whatnot is a very big deal and Jojo, I think you I don’t even know if you consciously do it. But I think you see those gaps like I’ve seen you worry about the unanswered in a lot of cases.

JG [Jojo chuckles] I think I do worry a whole bunch. I think that’s like one of those things that I think you get from being a PM, is that every product I’ve ever worked on, I can tell you the 10 things that are wrong with it, like the 10 things that I would do in a heartbeat if we had all of the skills and like time to do the things. I think that you have to be hypercritical of what you’re building. But you also have to be an advocate and like I’m super protective of my team, my team of fantastic and like making sure that people hold space for that and take that time is really important to me.

RZ How would you, I mean, I have my approach. Everyone has different approaches. How do you push back? As a PM, something just absolutely off the wall just showed up at the meeting. Walk me through that because that is a key key PM skill, right? Because, yeah, that’s the kind of stuff that really jeopardizes a product.

JG Yeah, that’s really hard. And it depends very much like who it is that’s asking it, why they’re asking it. I think that again, my go to is always like, let me talk around this with you. Let me try to get to the core of what it is that your problem is because most of the times my experience with these is, is that they’ll tell you the solve that they think it is, and that that’s not really the solve. Yeah, you know, the problem is actually much deeper than that, or even like much easier than the thing that they think they think that something is an easy lift. That’s like, you know, you’ve been there when it’s like, oh, yeah, that’s easy. And you’re like, easy for like a month’s worth of engineering work. So I think that I spent a lot of time being a nice person that people want to spend time with and talking to because then if people want to talk to me, I might find the actual problem.

PF It’s a choice. It’s a choice we all make. 

RZ Here’s a trick that works with really senior people because what do you know about really senior people? A, they’re smart. They got there somehow. They’re probably smart, I’ve met some stupid senior people, but most are pretty smart. Two, they’re usually pretty opinionated, right? Like, this is their domain, it’s their terrain, and whatnot. So they could actually be pretty far away and then show up for a review meeting and then throw out all these ideas. Right? The thing you got to keep in mind with very senior people is they have a lot of other shit going on. So the the move the killer move here is to nod and say these are really good points and we’re talking about them and just utterly ignore them. Just never bring them up again. They will never bring them up again because they have no recollection of ever saying them to you. It’s actually effective because they actually don’t want that noise. They can’t help it right. They’ve been conditioned to be listened to and so you hear them out. But really the best thing you can do is to take it and file it away and never bring it up again ever.

PF There is a caveat here, there is a caveat. Which is that every now and then you will run across somebody who is a write things down for later leader.

RZ Ughhh. 

PF Which, frankly, Richard includes you. 

RZ It’s true. I do write this down. 

PF Which is like two weeks from now, let’s check in on the status of X, Y & Z. And what will happen. If it is, but I will give you this if it is a right and I’ve had this experience because I’ve done the exact thing you’ve described, which is like, okay, there they go, well cross your fingers and someone will be like, we’ll never see him again. Don’t worry about it. They show up again two weeks later, and they said I was curious about the status on A, B, C. And you look him in the eyes, and you go, we have not made much progress on A, B, C. And now…

PF This might be the worst advice we’ve ever given anyone? 

PF No, no, no. And now and now you are on the hook. And that’s how you know you actually have an accountability driven leader. Now you need to go get A, B, C underway and your next step within about three days. You need to get in there for 20 minute meeting. Yeah, you need me like okay, so we got that moving. And you know, I was curious what other thoughts you had and the here’s the thing. They’re very used to this dynamic. They know that no one listens to their peers and everybody waits for the boss to kind of drift away. And listen, when you’re a boss, you know that you are a part of the problem. Like there’s some things that you say and you’re really emphatic about and then you drift away and everyone’s like, Yeah, whatever. But there are certain things that really matter, right? And so like, that’s a give and take, you don’t have to panic when they catch you out on it. So just a little update to Rich’s advice. 

RZ Yeah, no, fair.

PF It can bite you right in the ass.

JG It can but it’s also I think that like, it’s actually kind of a useful thing to manage like busy stakeholders, whether it’s like external stakeholders, but also internal stakeholders. Like we have lots of people in the empty project to work on a bunch of things. And like, you know, I take Gina for example, like Gina, firstly, a fantastic human, but she’s busy. So, there’s a lot of times where I’m like, you know what, let me take that away from you. Like, I’m gonna take that and I’m gonna run with it, and I’m gonna report back to you, as in when it’s needed, and now you don’t need to think about that thing so that like you have trust that I’m going to do that thing. And I think that that’s something that’s kind of a less dramatic way of being like, I don’t need to worry about this. But like, yeah, just to keep being like, even if it’s like I’ve made no progress, because it’s not as important as X, Y & Z, but just, I’ve got this. Let me take that away from you.

PF I have to say leaders are a little bit like children, right? Like we’re a little bit helpless because we can’t do the things ourselves. And so when you do that…

RZ Woah, woah, woah, slow it down there. I can do all kinds of things. 

PF Oh, yeah, but you shouldn’t. And someone comes to you and takes it away and does it and brings it back. It’s literally like you’re a five year old seeing someone do a magic trick. You’re just like…they did it. Oh, wow. I didn’t expect it. Wow. Oh, it’s so great. And you’re like how did they do it? They went away and they updated the Word document. Oh my god. It’s the most exciting thing and then you’re kind of embarrassed ’cause like you didn’t ask for it. You didn’t just say do it. But it is it is a superpower. Like just going away and doing the work. It’s many people listening It’ll be like, what’s he talking about? But try it.

RZ Yeah, Jojo, let me ask you this, you know, you wrote you wrote it down, there’s a clear dotted line to the thing that has to get dealt with. And it just seems to not be getting dealt with you just keep hitting a wall walk me through that scenario and how you would handle it.

JG It depends what it is obviously, I generally find if we finding something, you know, it happens we hit a wall especially like you know, whether a particular feature or a particular like use case that we don’t really like know how to get progress on, there sometimes that you can get there by just like, keep bringing it up, but like, I’m serious, like you just repetition, then someone eventually is gonna be like, Oh, yeah, we’re gonna join us real serious about this. I better do something. The other thing I like to do, which is like if any of the team listens to this, I’m very sorry, I do do this. Don’t realize.

PF No one. No one listens to this podcast. 

JG Is I’ll create a Dash channel with like the name of like what it is that I’m worried about, and then invite everyone that I feel needs to be worried about it too. And then it’s like it’s something else is holding them accountable for you. But you can set it for 24 hours in advance. It’s like, all the channels still open. It’s not me, it’s the dash channel that the bad…

RZ We need to explain with Dash is, but this is a good that’s a great use of a tool as the source of pressure rather than you standing over someone’s shoulder. Where’s the thing? Where’s the thing? Where’s the thing?

JG There’s no joy in being that person and there’s no joy in having that person over your shoulder. So making another thing the bad guy here is a real helpful thing for me. 

RZ Right, right. So dash is a tool we build for slack. It’s free. It’s available at dash for slack comm that you create a channel with a goal and that channel expires and the clock is ticking. And the whole point of it is to get everyone accountable towards finishing the thing. It’s a it’s an accountability tool.

PF It’s a simple Slack channel with a clock that ticks. Yeah, it is. That’s all it is. And it’s but boy, is it a power tool of all the things that we have built. It’s the one thing we use the most internally. Everyone has to share the pressure and everyone. I’ll tell you what, when you see that Dash, you don’t go Oh, no, you go. Yeah. All right, we actually get in there and figured, yep, let’s deal with it.

RZ Sometimes you just want feedback. Look, I’m gonna make a call. But here’s your chance. You’ve got 12 hours to tell me tell me what you think. If you say nothing, I’m gonna assume that’s a blessing. And off we go. Right. Like it brings finality, it brings forward motion. And I think, you know, there are other tools that try to do stuff like this. And tools don’t always solve it. Usually, the real power tool is the human that knows how to get things moving. 

PF Yeah, but it’s very, it’s very neutral, as opposed to that email that says gentle nudge, gentle nudge. 

RZ Yeah, just checking in!

JH I don’t want to ever say checking in or nudge of this. Like I’m very much like the if I didn’t hear from you by 12, tomorrow, I’m going to send this and this is the way that we’re moving forward. Because, right, you know, I come from a background outside of technology. As you both know, like I was in theater, I was a producer. And like, things there have to move just as fast as software, but like, there’s way there’s even more egos and there’s so many people, and just giving people a deadline was something that I like had to do in that industry, because otherwise, genuinely, things can fall apart, like, in a snapshot.

PF That curtain is going up.

JG Right. And it’s gonna happen either way.

RZ To close this out. I want to I want to walk through some of the tools like what are the tools you use, Jojo?

JG So obviously, we’ve mentioned Dash or a day, we also have been using Basecamp as a tool for like, every every single minute that I write goes into Basecamp so that it’s then like a searchable knowledge base. So if you have a question about a particular type of screen, for example, you can just like put that name into Basecamp and see every minute meeting that’s ever involved that particular screen. So it’s just really helpful. The other thing that I really personally like to use is Whimsical. We mentioned Whimsical a little bit earlier on, it’s, it’s a tool that allows you to create flowcharts. And like sticky notes and mind maps,

RZ Very light lifts, you could just pick it up and use it.

PF I’m such a Whimsical fan. It’s awesome. 

RZ It’s funny to hear that, you know.

PF It’s because you can do you can use it live in front of people and move. It just, it’s so fast. And so, I use it when I’m talking about new engagements with prospective clients because I can I can move the rectangles around in front of them. And they’re like, Oh, you do understand this, I see it.

JG It also is like, effortlessly, like not ugly. Whereas other tools you have to put the effort in to make this something that users can like view in a meeting whereas that’s just like out of the box pretty it’s good.

PF Tell us a little bit about Clubhouse because everyone talks about it and I don’t understand it.

JG I love cCubhouse so much. 

RZ Oh, no. I mean ”oh, cool”

PF No, no, that’s fine. There’s another $5,000 on our AMEX.

JG I’m not even sorry, it’s definitely saved you $5,000 worth of time because I will state that. It is with, you know, with a team of 17? Like JIRA, for example, gets really bloated and slow with next gen JIRA, like, we have had over 1000 PRs on the project on GitHub. So like, that tells you how many like PRs that’s like more than that of tickets. So with the amount of tickets JIRA was just becoming basically unusable for our team. 

RZ From a performance perspective?

JG From a performance perspective.

RZ Like clicking in, that’s just unbelievable. I mean, that’s a huge deal. Right, the feature of Blubhouse a key feature is its performance. 

JG Its performance is incredibly fast, and it just means that like, I can do my job much better. People are actually looking at it instead of being like, Oh, God, what’s Jojo done? I’ve got an email from JIRA. Oh, no. And like we’re just having more conversations there instead of in a Slack thread, which is you know, has its place but you lose all the history and then just having a place where you’re talking specifically about this particular design and user story is incredibly helpful. And that’s why Clubhouse is my favorite.

PF Alright. So when you when it’s time to replace JIRA and it’s basically always time to replace JIRA.

RZ I mean, what a damning statement, frankly, I mean, JIRA’s been around for 50 years already, you’d think they could sort that out. 

PF If I was a PM on JIRA, and I heard this, this would be my moment of panic, right? Like I’ve told you guys, for real we’re losing business because it’s not fast enough. They’re like, well, we can’t make it fast enough because the visualization current, doesn’t matter. Right. Doesn’t matter. 

RZ So it’s for the Clubhouse project management tool.

JG It’s not just about being fast, it has like burndown charts and diffs between tickets so you can see what someone else changes like there’s a lot of other features under the hood that make it like more useful for a PM in my opinion.

PF For your nerdier PM is what it sounds like for someone who’s like really kind of drilling in on.

JG Yeah, for the nerds. We’re here for the nerds. 

PF Yeah, no, we better be there’s a thing that you wrote towards the end of this, which is something I’ve never heard before. And I thought it was really interesting. I’ll throw it to you. And you can explain why. When someone offers you praise, praise for Jojo you write it down, how come?

JG It’s actually something that was told to me like when I joined a team once before, to just be like, write everything down that’s positive, because it’ll help you feel like you’re making progress. It will help you be able to demonstrate the value that you are creating. And it will also just be able to like track things you’ll be able to be like, these are skills that I’m doing really well in. No one’s said this, but like, how can I improve this area? You know, my technical skill? I think it really charts the progress that you’re making. And as someone who loves data, it gives you data, it allows you to be able to be like, hey, Paul, here’s 17 things nice people said about me, you should think that I’m a good PM.

PF I mean, that’s a powerful signal. What I love I love this line. For some of us, it can be challenging to say positive things about yourself without coming across like a braggadocious Brontosaurus, so let other people’s words speak for you. And I’m just really in there about braggadocious Brontosaurus, which are two words I’ve never seen before. 

JG Yeah, truthfully, I just didn’t know how else to say it. But like, you know, we love alliteration. We love dinosaurs. It makes sense.

PF I’m an amazing, it’s very exciting to think about the Brontosaurus. Okay, so great. So everyone should now go and start writing down all the nice things people say about you.

RZ I gotta say, I like the timeliness of this. We are in a weird time. There is nobody coming over to pat me on the back in my house while I’m on a video call. When I share good news, I still get blank stares. Maybe that’s because the video is still processing. It’s a weird time. I think taking a minute to make good thoughts and good comments tangible is a positive thing. People are in the dumps a little bit right now like and that’s a real thing that’s happening. They can say I feel great guys. I feel really great. And they’ve just eaten their nails down to the bone. Right? That’s really happening. So I think it’s a good good tip. Even during these difficult times we’re in right now.

PF I’ve heard of companies that are taking like five minutes and at the end of each meeting so that people can give each other praise for how they’re supporting their teams. 

RZ Okay, alright, let’s not get let’s not let’s not get out of hand here. Okay, let’s, let’s…

PF Rich, I’d like you to start doing that I’d like every meeting we have, which is about 12 a day to include just five minutes of praise for me. That would actually add a lot of value to my experience. 

JG That might take up a little bit of time. But we do have this channel in our work Slack, which is hashtag applause. It’s like my favorite channel. It’s like engineers being called out, designers, PMS, all sorts of folks being called out of like work that they have done and like why they are excellent. And it’s lovely. 

PF I love interdisciplinary shout outs the most when it’s like the engineer going. I never saw anybody present quite like that, that that was amazing. And it’s vice versa. Alright, so people should go up. They’ll be a link in the show notes…

RZ To all the tools we just described. Yeah.

PF Yeah. Is there any you know, social media anything you’d like people to look at when they think of you should they follow you on Twitter? What do you think?

JG Sure, I’m @JojoGiltsoff on both Twitter and Instagram on Instagram. I share embroideries that aren’t product related.

PF That alone is really good. Any particular kind of embroidery anything we should know?

JG Lettering around like being a homebody more appropriate pre pandemic before people were actually confined to their homes.

PF A little less ironic right now.

JG A little less ironic. Yeah. [music fades in]

PF Such is life. That’s that is the situation we’re all living in right now. It’s much less ironic that it used to be. Alright, this is fantastic. People should ho check out the article and follow you on Twitter and check out your embroider and Instagram and thank you for coming on the podcast. 

RZ This was great. A lot of good advice here, Jojo. Thanks for doing this. 

JG Thanks for having me. 

PF So rich people should know if they want to work with someone like Jojo and a large team to get their strategic goals inactive and turned into actual software, Postlight is absolutely the right long term digital strategy partner for them.

RZ I feel like we talked about Postlight in the conversation, check out the case studies, check out the MTA case. I think it’s really really interesting work we’ve done and check out anything out there all the other case studies at and reach out We’d love to give out free advice. 

PF Just did it yesterday, just you know, somebody came in with a very vague question and I wrote back like a whole page of explanations on what they need to do. Felt good about myself.

RZ Just generosity. 

PF That’s where we’re at. We’re here to help. Bye, everybody. And thanks, Jojo. [music ramps up, plays alone for 3 seconds, ends]