This week Chris and Gina answer a listener who asks, “What do you do when you get work back that isn’t going in the right direction…and you hate it?” From unpacking why you hate the work to coming up with ways forward, Chris and Gina share tips to ensure everyone follows the north star and puts out high-quality work.
Gina Trapani I had an AP English teacher—this is another episode—but boy, I could not. I got good grades in English, my entire writing career. And I could not please her and my God, it became my life’s mission to please her.
[Intro music fades in, plays 10 seconds, ramps up.]
Chris LoSacco Hello everyone. And welcome to the Postlight podcast. I am Chris LoSacco, president of Postlight and I am joined as always by my co-host Gina Trapani, the CEO of Postlight. Hey Gina.
GT Hey Chris.
CL Today we are here to talk about one of my favorite things. It is listener feedback
GT [Laughs.] Oh, we love it.
CL Yeah. And if it’s okay with you, I’m just going to read an excerpt of an email that we’ve received at email@example.com—little plug. We would love to hear from you too. It’s always great to hear from listeners. And this is a very interesting, thought-provoking topic. I’m just going to put it out there and then we can share our thoughts. So here’s the note: Our office is two people and we don’t have a lot of bandwidth given that we’re running four existing projects, two soon-to-be projects, lining up our three next projects and doing whatever else is expected of us. This means we rely on communications, budget, finance, procurement, and legal to make what we do happen. And sometimes, sometimes you hate it. Whether it’s advice, a purchasing decision, a legal opinion, or a graphic, sometimes you just hate it. So I’m asking for advice. What do you do when you’ve been working together towards something and you get to the point where now you’ve been staring at this thing for months, you get weekly updates to show progress, and it should be ready to go, but it’s just awful? Cheers—Jay.
GT Oh, Jay,
CL What a note!
GT What a great, great note.
CL We’ve all been there.
GT Oh, we have all been there.
CL I know exactly what this is referencing, this feeling.
GT Yes. The feeling, the feeling when you’re in the meeting or you get the email and it’s the thing and your heart just sort of sinks because you’re like, this isn’t good. This isn’t what was supposed to happen.
CL Right. How did we get here?
GT And it’s that sinking feeling. And then you lose that motivation. And now suddenly it’s like, I don’t have an effort that’s about to launch or a thing that’s going to happen. I have a problem because it’s a thing that I don’t feel good about. And I just hate it. Like, thanks. I hate it. Like that feeling is so universal and happens every single day! [Both laugh.]
CL I know. I know. We need to address this specific question, which is when you’ve gotten to that point where you feel like it’s awful. What do you do then? But I also think we need to rewind and at least spend a minute talking about how do you prevent even getting to this point? Because sometimes you can see that the train’s going to go off the tracks. And if you can see it ahead of time, you know, you should try to course-correct it if you can. You know, I mean, one thing that I think we’ve done in the past is the advice we give is design early. Do the wireframes and do the prototypes up front so that before you get 3, 6, 9 months down the road and you’re like, uh oh, this was a wrong decision that happened in the first four weeks, you know, prove out your ideas so that you can course correct. Even if that proving out is happening in a group that is adjacent to you, it is totally reasonable and possible for you as a product leader or as a mid-level manager to make a request of another team to say, I want to see where we’re going before we go and it needs to be more than, you know, a 14-page document. It needs to be a wireframe, a design, a high-fidelity design, a sketch sometimes will do. So that you can react and validate something before you’re further down the path. So I think we just need to say that up front that if you can get a clearer picture, even if it’s a fuzzy picture, get a picture in the beginning so that you can make a call about where you think you’re going to end up as this effort progresses.
GT Definitely. Getting ahead, you try and prevent getting to this spot of I hate it is huge. I would even go sort of further toward like in the very beginning, I think it’s so important to just set that north star, like, what are we doing? We are going to increase attendance to this event by 20%. We are going to put out a new thing. Like there’s a north star. And there’s a reason why you’re doing what you’re doing. Because for me, when I’m in that spot where I’m like, I hate this, this wasn’t at all what I expected or I don’t think it’s good enough. I have to unpack like, why do I hate this? Why am I reacting this way? And I mean, there’s a few options. One—and the most easy one to communicate and say and make it about like the work and the effort and not about like, you know, your personal preferences is like—this isn’t accomplishing our goal. This doesn’t bring us closer to our goal. This doesn’t line up with the why we’re doing this. Like we need to come back. We need to go back to that. It’s hard to do this though. Right? Because the feeling, I think particularly for people who have high standards, who love their work, particularly in sort of the digital space, if you’re working in an organization that isn’t digital, but trying to become digital, that feeling of this just isn’t good enough is so palpable and can feel just so strong. And you have to take that minute to step back and say, why? Like is this about my personal preference? Or is this because it doesn’t align with the goals that we set out? Or is it just because this work isn’t up to the standard that we should uphold? And each one of those has kind of a different approach. But it’s easiest to say this doesn’t work because we set forth this goal and this decision, this purchasing, this legal opinion, this graphic, it doesn’t get us closer. What can we do to fix this?
CL Yeah. It’s so funny when you set that goal, you also have to make sure that everybody is thinking about that goal at all times.
GT At all times.
CL Yeah. And it can feel a little awkward. Like it can feel weird to start every team meeting by saying, I’m going to restate our north star. Something we’ve said internally at Postlight is the team needs to all be the keepers of the thread. Like what is the thread of what we’re doing? And it’s a habit you have to build consciously, to say, we’re going to continually remind ourselves what it is so that we are measuring the decisions we’re making against that north star. Cause you’re totally right, Gina, in what you’re saying before: it’s easy to validate something if the thing is obvious, if the north star is obvious. If it’s not obvious or clear or explicit with people, then I think it’s harder to measure something up against it, especially in those early stages.
GT Very much so. I mean, it’s weird and uncomfortable along the way to state and restate over and over again what the north star is, but you kind of have to because you want to be able to measure what you’re doing against it. I mean, look, we had a client project not so many months ago where we got to kind of the late stages. We do a lot of internal reviews before we go in front of a client. We looked at the work and a few of the leaders said, this isn’t what the client’s trying to do. The client’s trying to do this work. Like, how are we going to defend this or put this forward? This is what you need in order to make the next steps in your business. And we couldn’t and it was rough.
GT It was a rough meeting because everyone was like, wait, we didn’t know that’s what the client wanted. That’s what the client wanted? We had lost the thread. And we had to make a call. I mean, so here’s the thing. When you get to that place where you’re like this doesn’t line up or this isn’t good enough or this isn’t going to work, you have to make a decision, right? And there’s a few paths. There’s like we can make tweaks to this and get it to the place that it needs to be. We can blow this whole thing up and start at a blank piece of paper, which is the more nuclear option. And the one that is very likely to upset a lot of people who put a lot of work in to begin with, you know. But sometimes it’s necessary. Or, you know, for an internal effort that you’re responsible for, there could be this moment where it’s like, should we even be doing this at all? Should we shut this down? Is this effort worth doing? I mean, you don’t always have that option, but if you’re the customer, if you’re the person who has like initiated the thing and the thing just totally went off the rails and you’re like, this doesn’t make sense anymore that you know, this changed and then the work didn’t get there. You have to make that call. I guess there’s another option, which is, I hate this, but perfect is the enemy of the good. It achieves the goal enough. And so I am going to register the fact that this doesn’t feel good enough for me, but I’m going to disagree with this direction, but I’m going to commit and we’re going to go forward. I’m going to accept that I don’t like this for whatever reasons, but also I think that it’s worth continuing. And I am just going to roll with what the team is doing here. That’s a tough one, right? I mean they’re all tough. These are all tough options.
CL That’s the thing is: sometimes there’s no really good answer and you just have to choose the least bad answer or the one that feels like it fits the situation the best. Sometimes disagree and commit is the right call. It’s not rolling over. It is stepping back and acknowledging that even though you may have a particular preference or a thought on what something should be or could be how it could be better, that doesn’t necessarily mean that that is the only right decision. And it is completely reasonable to say this isn’t what I would do and this doesn’t feel right, but I can acknowledge that it’s going to move the ball forward. And so I’m going to commit to moving this along. Even if you don’t like it for whatever reason. And we’ve been in that situation. A very common example I feel like for disagree and commit is when the CEO is particularly committed to something, right? They’re particularly committed to a particular design or a software platform that they chose or a vendor that they really want to use. And you’re like, if I was in that seat, this is not what I would be choosing, but the reality is the CEO is making this call. And so I’m going to get on board and I’m going to figure out how to make the best within this situation.
GT (How do I make this work?
CL How do I make this work? And I think that that is a real option for someone in Jay’s position or someone else in a similar position—disagree and commit is something to think about. I want to go back to what you said before, which was sometimes you gotta blow it up. Like how do you get to that decision? And then if you do think you have to blow it up, what do you do?
GT So I want to say one last thing about disagree and commit, cause the commit part is really important because I’ve seen people disagree and commit and I’m doing air quotes right now. And then when three months down the road, when it doesn’t work out, they go, I told you, I never really wanted to do that. You don’t get to do the I told you so. Part of the disagree and commit is that you say, okay, I’m agreeing. Because you do have this other option of blowing it up, which is where I want to move. And now of course it depends. Are you the decision maker? What is your role in this situation? But let’s say you’re in a role where you can say this isn’t good enough and we’re not doing this. Like I am going to blow this up. I’m either going to push back and say this decision, this graphic, whatever, it’s not good enough. And we need to go back and redo it. Or maybe you’re in that position of like, this effort went in a direction that it should never have gone and it’s not serving its original goals and it’s been months, its original goals actually aren’t as important anymore. And we are just going to shut this down. Those are tough decisions to make, because again, that sunk cost. You’re like all these people put in this effort and this work happened and we should just get it out the door, right?
CL Yes. But.
GT But if it’s not good enough. There are certain people ,and you are this, who are quality standards bearers. So if it’s an issue of quality, this is a super important role. If you hate it because the work just isn’t good enough and does not represent your organization, your client, your team, your vision to the standards that it needs to. There is a point where you just have to say this isn’t good enough and we need to do better.
CL Right. Do another round.
GT That is very tough feedback to give because you’re potentially hurting feelings. You know, you have people who are working really hard and just want to make progress. You’re stalling progress. You’re adding time to the timeline, right? Cause you have to make this call, right? Is the quality level versus the time that’s going to take to get it to where it needs to be, like is that a worthwhile trade off? But that is so important to have that person who can look at the work objectively and not make it about feelings and not make it about subjective preferences and say, this objectively is not good enough. And we have to do better. So what do we need to do to make this better? That is huge. And I have on many occasions said, well, I don’t like it, but I kept quiet. And I thought, eh, this doesn’t doesn’t seem great, but I guess we’ll just roll with it. And I think, I’m kind of calling you out Chris, like, you are very good at saying this isn’t good enough. We need to do better. And I’m getting to the point where I need to be more comfortable with that because I think that’s what creates great work, like great work that you’re proud of, that you want to go out with in the world. You don’t want to feel that sinking feeling of like, I can’t believe we’re doing this. Because that doesn’t go away.
CL No, it doesn’t go away. You can’t get back from that. I just, I want to temper that though, because we’ve also given advice on this podcast where we have said ship early and often and get work out there and don’t let the perfect be the enemy of the good. So I think I just want to acknowledge that sometimes these decisions are not always clear-cut. Sometimes I definitely have sat in rooms and I know you have too, where it’s like, this is not up to the level that we need it to be at. It can’t go out. We gotta do another, whatever. Another design, another iteration on a piece of software, another run at a feature, et cetera, et cetera. And sometimes those calls are hard, but sometimes you just gotta make those calls. Or if you’re not in a position to make the call, you have to advocate for it. You have to say, this is not going to achieve our goals. And here’s why, and you’ve gotta figure out how to get in front of a decision-maker to make that case. And we’ve been in those positions and in those rooms. But I also think there are times when, you know, something is not where you need it to be. You probably don’t hate it, but you know, something’s not where it needs to be, but you can release it and iterate on it. And there’s value in shipping and getting something out the door. So I want to put that out to our listeners, to the world, put that out in the universe here. That it’s a judgment call. And sometimes you gotta realize that even if something is not exactly where you need it to be, there’s still value in shipping it. There’s still value in saying it’s in production, it’s in a real user’s hands. And we know that we’re going to iterate on X, Y, and Z, in the first point release. Because you know, as a product manager, I’ve been in that position too, where I’ve just had to release something, because it was ultimately the right tradeoff to ship as opposed to doing another round.
GT That’s true. That’s something you have to kind of live with. It is a judgment call and you have to live with this idea of like, I know with PMs, especially on an MVP, right? You launch an MVP and all you see are all the things that are missing. And there’s this upset sort of feeling of like, Ugh, but that is your feeling. And only you can see those things, right? If you’re getting working software in front of users for the first time, they just got something that they didn’t have before. And that, that outweighs the ah, we didn’t build those five features that I think are really important.
CL Exactly. Something else that I feel like has worked well for us that is worth sharing when you’re in this position, especially if it’s another, part of what is in Jay’s email is that it’s another team, right? It’s somebody else who’s making this call, it’s finance or legal or communications that is doing something that you feel like is just you’re not on board with it, but it’s also not really your call. You’re not in that position to blow it up or to say, we need another round. Something that has worked really well in the past is make a case for why you think it’s the wrong decision in writing. But at the executive summary level. It’s not a 14-page memo about you know, I’ve done all the research and here are all the reasons why this is not the right path to go down and you should really consider blah, blah, blah, blah, blah.
CL Because if it’s too heavy handed, it’s not going to work in your favor. And the receiving team is going to be like, what is this? I didn’t ask for this. Like, what’s going on? But instead if you write down like again, high level, one page or less, or maybe it’s a couple of slides and it’s like, here’s what I’m seeing, restate the context. Here’s the north star, as I understand it. And for our company or for our shared vision and why I think this doesn’t achieve what we are going after, right? If it’s in the public sector, like we have a duty to serve the public. And here’s why I don’t think this is serving the public in the best possible way. And then propose an alternative and then say, instead of going down this path, instead of choosing this piece of software, why don’t we do this? Why don’t we choose this platform? But have something else that you can offer as a path forward. It’s very difficult on the receiving end. Again, if you get a bunch of feedback and then it’s like, I just think what you’re doing is wrong. Good luck.
GT Right. Here you go. Please figure it out. Right.
CL It’s very hard to deal with that. But if you’ve got someone who’s like, you’re saying you want to go with Droople and it’s going to take nine months and it’s going to be blah, blah, blah. But I really think you should go with WordPress because the editorial team is more comfortable with WordPress. It aligns with our vision. There are these six plugins you can use and you can get it all done in four months instead of nine, they may not take the recommendation or the suggestion, but it’s a much more valuable thing to receive than just, you know what I think what you’re doing is wrong. Good luck, please fix.
GT I mean, this is just advice for life in general, like offering a path forward or a solution. I mean, part of what that takes is like getting yourself out of just that visceral feeling of I hate this and I feel just beaten down and ugh, and like being able to separate yourself from it and being like, why do I feel this way? What are the points I want to meet? You really have to kind of have that distance a little bit. I feel for Jay—Jay’s in a two-person team. There’s something that I wanted to say though, especially when you have a small team and these are things that are happening from other groups coming your way, everyone’s face kind of falls. And like suddenly a thing that you are excited about and doing together becomes a chore because you hate it. And there’s something about when you can be the person who says this isn’t good enough. We can do better. Here are a few ways that we can do better. You can see the people in the room activate, when you’re that person who stands up and says, this isn’t good enough. And I think we can do better. Let’s figure out a way to do better rather than just accept this and move forward. You can really activate your team, the people around you, you can see the people who agree with you that it’s not good enough, but feel disempowered about doing anything about it, right? Become empowered and become activated. Right? And then it becomes an opportunity to be like, what can we suggest? How do we route around? How do we get around even having to make this legal decision?
GT What could we do with this graphic that would make it better? Like then it becomes an exercise in group problem-solving versus like, oh, I just have to accept that this is my reality because we’re a small team. And we have to ship this thing that’s just kind of bad. I mean, cause sometimes you do have to get to the disagree and commit, right? Like it’s kind of one or the other, like we’re going to try to figure this out together. We’re going to push back. You have to be able to push back on other teams and others once in a while, you can’t do it every time. Cause you know, then you become the contrarian who’s difficult to work with, right? Like there has to be some give and take and some cases you have to say, this doesn’t feel good, but I’m going to disagree and commit. And other times you have to say, look, we need to do something better here because this just doesn’t get done what we need to get done. And yeah, being that leader, and this is the thing your team is going to be willing to disagree and commit when they see you stand up in other times and say, this isn’t good enough and we need to do better. Like that will activate folks. And it’ll keep you from sinking into just the sad depression of accepting subpar situations, which I think can happen. But particularly in small teams with limited resources, this is tough and this is hard, but it’s very much just a mood and a morale thing that can happen.
CL Two things come to mind. The first one is a very tactical bit of advice to add on to what you’re saying, which I completely agree with. Sometimes you gotta be the one to raise your hand and that can actually change the mood in the room. I would add one thing to that, which is one judo move you can do is acknowledge the work that you hate. Like just acknowledge it. Just say I recognize that a lot went into this or I recognize that there were choices that were being made here. And I appreciate the fact that the team did blah, blah, blah. Or I know that this decision that was being made involved a lot of conversation, whatever it is, just acknowledge it and that can help prime the pump a little bit and make it, make people a little more willing to hear the tougher feedback, which is, but this is not good enough. If you don’t take that moment to just say, there is work that went into this, whatever this is, if it’s an artifact that’s being produced or a decision that’s being made or a path that’s being chosen, the first response can be defense because it will feel to the person like you’re saying, you didn’t do enough work. You didn’t do it right. But if you disarm that in the beginning and say, I recognize a lot of work went into this and this is, you know, it’s not a judgment on that work. There’s really good work and thought, I think we can go in a different direction. I think we should consider X, Y or Z. You know, it’s a little bit of a tactic in the beginning to make sure that the tougher thing that you were talking about, which I completely agree is sometimes necessary, will get accepted. Well. So that’s the first thing I want to say. Second thought, you know, I’m thinking about a leader who is listening to this and is worried about this malaise, like permeating their organization and feeling like I’ve got people who just don’t care and who are fine with things going out the door that they’re not happy with.
GT They’re beaten down and just accept mediocrity. That is a poison.
CL Exactly. This is what I wanted to say. It is incumbent upon you, leader, to make sure that you are engendering the kind of culture that encourages people to speak up. That encourages people to say this isn’t good enough. And how do we make this better? And sometimes it starts at the top and sometimes it is about, you know, the CEO or the CIO or the CTO saying we haven’t been hitting home runs. We have been striking out and we need to get our batting average up. And that means we need to, you know, do X, Y, and Z. And I want all of you, everybody in my org, To be thinking about it.
GT Again, you can’t be the person for whom or the leader for whom nothing is good enough. Right? My grandmother had an old saying, you kick every stone in the road, then you will wind up with no shoes. You know, you have to choose the things that are most important, right? And there are times when you’re going to have to disagree and commit. You do not want to create a reputation of the person who never accepts anything and is totally contrarian. Because then people will start to route around you and just be like this person’s impossible. When you have a leader who upholds higher standards or when you have that hard conversation that says, this is not good enough, we need to do better, everybody sits up a little straighter and then the next project, someone won’t just assume that they can just kind of do the thing that they always do and then I’ll get accepted. They’ll go like, Hmm, last time I had to redo this or I had to revisit this, let me make sure I understand what I’m doing here. Let me connect with this leader and make sure I’m clear on the north star. Let me get ahead of the work of not getting accepted. I think it creates,when one person and one team or one leader holds a higher-standard quality and says we have to do better once in a while on a sort of regular basis, everybody starts to follow suit, right? Especially when that action leads to higher quality coming out in the end, this is how you change a culture of, well, this is just the way it is. And we’re just going to, you know, accept mediocrity. I mean, I know it’s not good compared to our competitors or compared to what that other team’s doing, but you know what, this is—
CL How we do it around here.
GT This is just how we do it around here. I mean, we could do better, but who’s going to stand up for that? Right? So it’s like being that person that stands up and says, we can do better. Let’s do better together. And I think that message is important. How do we do better together versus just like not good enough? Do it again. Bored. Bad, not good. Bad. There’s gotta be a little bit of collaboration. I think it’s just so important. And I think that really does set this culture of like, we are striving to do better work than we have, but again, you can’t be that contrarian every single time. You really do have to choose your battles. It’s a very nuanced judgement call and it is very hard to make that kind of nuance judgment call when you are consumed with a feeling of just, I hate this and I can’t believe this went this way and like frustration and anger. So you really do have to separate yourself from that emotion.
CL We hope this was helpful, Jay. We feel you, we see you, we’ve been in those rooms and we appreciate you.
CL [Outro music fades in, ramps up.]
And our hope for you and for the listeners and for everybody who takes this in is that we make all organizations care about what they’re doing and what they’re putting out into the world so that this place gets a little better for all of us. One last thing we’re going to suggest: if you’re at the end of your rope and you don’t know how to affect change in your organization and you want some help from a third party, please reach out to us. Hello@postlight.com. Sometimes you need a consultant to be able to say this isn’t good enough and we can do better. And Gina and I and the Postlight team would love to be that support for you. We do all kinds of digital strategy, software design, top-tier engineering, high-scale platforms that reach millions of users every day. And if you’ve got a challenge where you’re like, I think we can be doing better, but I’m just not sure how to put into practice what you’ve been saying. Let us help. Reach out to us at firstname.lastname@example.org
GT And we love questions too. Jay, thank you for writing in. If you’ve got a question about anything that we’ve talked about, we love this stuff. We’re happy to answer. Send us a note. Hello@postlight.com. Thank you, Chris.
CLThank you, Gina. Thank you all for listening and we will see you again soon. Bye.