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First Round Article about Jay’s User Guide

Jay’s User Guide

Welcome back to WorkMinus, where we talk about what we need to drop from how we work and quick habits you can make today. Today, our guest is Jay Desai, CEO of PatientPing, and our topic is Work Minus Disconnect. Hi, Jay. How are you?

Hi, Neil. Thanks for having me.

Yeah. We’re very excited to have you on the show. You have done something very interesting in your company. You’ve actually written a user guide, but not for your products. Tell us more about this user guide you made.

Yeah. So our leadership team has been scaling quite rapidly over the past six months and one of the things that I’ve realized is that a lot of work and a lot of success for any given organization stems from very strong close partnership and trust between team members. So for me, as CEO, that means building very rich trusting relationship between me and my team. And as more people started joining my team, and I didn’t necessarily have a rich history with them prior to them joining the company, I felt that it would be very helpful for them to get a very clear sense of the expectations that I have of them, how I like to work, and really user guide to working with me. I thought that would be something that would be very helpful for them. I know I have started new jobs before and I wanted to make my boss happy and wondered what their perks were, what their style was. Sometimes I like guess working. So I thought I’d take the guesswork out of it to make it a lot easier for my team to be successful in their role.

So you wrote up a user guide about how to interact with you. How many pages is that? How long does it take to go through?

It looks like seven pages–six and a half pages.

All right. Great. So it’s basically a kick-starter to get somebody aware of the ways that they need to work with you. What are some of your favorite parts of your own user guide?

I can describe a few. I think, ultimately, so much of work, particularly in technology businesses, is about really great communication. I think I’ve found that the vast majority of dysfunction on teams stems from poor communication, or infrequent communication, or people just sort of missing each other and talking past each other. So I think, probably, one theme across the entire user guide is about communication and making the quality of those interactions really high. So I think the section on communication is my first section and it is one that sets the groundwork. But then, you know, I do try to get pretty real and really honest in it. I talk about how I deliver feedback, my triggers. I talk about my weaknesses and my misgivings and just limitations. Those are some of the areas. 

Yeah. Why don’t you pick just a small section and read it all out for us?

Sure. I’ll pick three here. One is around communication. So I say: I found a vast majority of issues are results of poor or infrequent communication. So it is important that we communicate well and often. One thing I offer is a very tactical piece of advice right there. The hierarchy of communication to me, from most to least urgent is, to tap me on the shoulder, one, if it’s very urgent; to call me, two; to text me if it’s less urgent and it is decreasing in urgency; Slack; and then email.  So that makes it really clear because, sometimes, people will email. They’re used to emailing in their prior job. But in this company, we may be a Slack company. And so it just helps communicate what the level of urgencies and what mediums we should use for communication.

That’s one. Another one, I’ll read it. The number one way to succeed is it make measurable business impact that’s in line with our mission and the company OKR. OKR stands for objective and key results. I will measure your success by the business impact you make and if you’re not sure how your role or work output contributes to business impact and/or it’s not clear how to measure it, do not proceed until we are aligned.  The quick editorial on that is I found that in a lot of companies, goals are unclear. You come to work every day, you’re not really sure. People feel like they’re spinning. To me, it makes me really frustrated when folks feel like they’re spinning or they don’t know how they’re work is contributing to company impact. So I think it’s real important that everybody, everyday, you can come to work and you know exactly how your work out but makes an impact on the company. That’s something I make really clear.

That’s great. How do you find that people have–like when you first introduced this idea, were people excited by it? Were they put off by it? How do they respond to it?

Well, it’s been interesting because prior to me putting it out there publicly, it was just something that I gave to my team a week or two after they had been with the company. So I was able to context-set it and they had gotten to know me a little bit, and were able to get to know me before they read it, at least interpersonally, a little bit. And then I gave them the user guide. I think they really appreciated it and they find it to be refreshing in terms of just getting it all out there. Since I posted it, it’s been really interesting because most of my interviews that I do, people have already read it before I do an interview with them. And I have found that people respond with one of two different reactions. One is either, this is great. This is amazing. I’m so glad. I’ve never had this kind of honesty or candor with my manager and I love it. I would love if I could have this level of honesty with manager.

And then they’ll either react well to some of the cues or that’ll be kind of compatible with their work style or it may not be. And I think that’s really useful to know well in advance. The other reaction I get is, “Boy that’s really intimidating”. And for the “Boy that’s really intimidating” cohort, I actually think that it’s a really good process to go through that level of honesty and sort of draw out that level of honesty because that’s our culture, and to really be willing to admit to your weaknesses and push each other to be better, and seek excellence in your peers, and be comfortable that you may not be exactly the best at everything, but you should be willing to own what your strengths are. So stripping away what a lot of professional environment create safety around hiding behind which is a lot of pleasantries and passive aggression. Our company doesn’t have that kind of an environment. I think what we do is really try to support one another and speak honesty in our interactions with each other. And that’s the intention here. So what I have found is that it’s a useful screen that people who do react well to it are very drawn for our culture. And those that don’t, probably won’t do very well here.

Yeah. With the user guide, essentially, what you’re doing is you’re giving somebody a, maybe even like a year, head start on how to interact with you, how to interact with other people as it comes in. Now that you have this in place for a while, have you noticed any untold effects of kind of speeding up the process? Have you seen positive or even negative effects of that within your recent hires you’ve done?

Yeah. I think I’ve only seen positive effect so far. I think the level of candor and the depth of the relationship that I have with people that, historically, used to take a couple years, I feel like I’ve achieved in three to six months. It’s been pretty phenomenal.  It’s interesting, when I first started the company, I used to think, everybody should be friends. We should all be friends. That’s sort of how you want to deal with your co-workers. For some people, that was a little uncomfortable because they want to drop professional boundaries between their work and their home life. And so then I kind of over corrected and I created a lot of distance between me and my team. But I found, actually, there is that really kind of magical third category of professional relationship which is neither friend necessarily, nor distance where you create this ultra-professional relationship. Rather, it is a special professional intimacy that has been formed between coworkers, and it stems from deep trust and deep respect for one another’s capabilities, and a complete comfort in one another’s weaknesses. And so I feel like I’ve achieved that with a lot of the folks on my team where we can just sort of come to work and really feel like we’re ourselves and ourselves, and we understand how to support each. And I think that professional respect and trust only come when people can honestly talk about who they are and seek self-awareness at work.

Yeah. Do you have a name for this third category of not friends, not necessarily just co-workers? Do you just call it professionals or trusted friends? How would you say it?

No. I haven’t thought about that. Colleague fills it short when you really feel like they’re working side by side with your team. Partners is probably the right word. It really does feel like we’re partners in this journey together, and we all have moments of weakness and we’re going to be totally supportive of one another during those times, and we’re going to do  everything we can to make us the best versions of our professional selves when we come to work everyday.

Fantastic. Earlier, you said that the user guide is going to up the level of the quality and cuts down on the quantity of the questions that are going on in your team. Can you give us some examples of how that happens in your company?

Yeah. One example would be, you know, if you’re a manager of a function, then you’re typically responsible for some output or some performance. So we don’t really talk about how to communicate that progress. Let’s say you’re here and you’re communicating progress against a quota, or a sales call, or pipeline, a lot of what the user guide does is clarify how to communicate that, when to communicate that, who should see all the information. We don’t waste any time talking about that because that can be an area of discovery when you’re new. What we end up talking about is what to communicate. Meaning, what were the results? Why were the result off plan or whether they had a plan? What are we learning from it? And you really do get to get up a lot faster because you don’t waste any time on the process questions and communicating.

Yeah. Excellent. So you have your own user guide. How widespread has this happened in PatientPing? Who else has one? Do teams have one? What do they look like?

I wish I knew how widespread they were but I do know that most of the folks on my team have written one for their team and it’s interesting. For me, I only had to write one user guide which is how to work with me. For anybody else on the team, they have three constituent groups. One is managing up, the other is managing laterally, and the other is managing down. And so I do think it’s a different set of expectations that you want to communicate to each of those stakeholders. So I do know that folks on my team have written either multiple of those types of user guide, or one of them. I’m pretty sure all of them have written guides for their team for how to operate in a group norm. And I think several of us have sort of made their expectations, as individuals or leaders of their team, quite clear. I am actually curious to see the extent to which those — I have had a couple people email me on my team, or just across the organization, not necessarily on my team, to share with me their user guide and ask for feedback and whatnot.

As you’ve read other people’s user guide, have you found anything really interesting or noble about theirs?

I’ve now seen the leaders of other companies post their user guides publicly. I’ve had friends tell me about it. I’ve heard about government organization doing team retreats where everybody wrote user guides for themselves that are facilitated [inaudible-00:13:23] groups that use it as an exercise to create self-awareness and set expectations for their team. It sort of taken a life of its own out there which can really be gratifying to see. The thing that I found is that, almost uniformly, there’s something better about all the other user guides that I’ve seen than the one that I wrote, which is awesome to see. I think people had been able to take what I did, wants that further. For instance, I wrote a lot of my triggers to think that if somebody does something that will cause me to look unfavorably on them, for instance, the things that kind of irked me a little bit about teams, to help that expectations. And I found one user guide I’m reflecting on took it one step further, that said, when we’re — actually, let me flip that. I’ve heard somebody describe what their own weaknesses are. And they actually made it clear for the employee how to deal with them when they’re behaving that way. For instance, if they’re like a highly distracted person or they can be kind of manic with their ideas, which a lot of founders can be, they take it further and say, when that’s happening, just let me do my thing. Let me just try to run its course and then we can get back on what the output is that. But I thought that was really really impressive to take it kind of further as they can.

Yeah. Absolutely. It’s nice to have those things as a known open topic that everyone knows that, I’m going to ramble about the topic for a while. And when it happens, it’s not like surprising or people talk about behind closed doors, but everyone knows that it’s out there and it’s well known. That’s a very good topic. So talk to somebody who’s anxious to do this for the first time. What’s the first step to kind of creating your own user guide?

I think the first step is reflection. And I think there’s two categories of reflection that one needs to do. One of them is to think on all of the relationships where you really had a positive, trusting, supportive experience in that relationship, and actually whether you as the manager or you as the employee, and try to draw out all of the behaviors or processes or personality trait or communication styles that were present in that positive relationship, and then reflect on your most painful work relationship, and think about the dynamics that created those conditions. And then when you write your user guide, the job is to try to draw out that set of behaviors in a positive relationship and do as much of that as possible, and be very honest and reflective on the conditions that cause the relationship to fail or to feel strained. And again, be very clear about that. And I think that the framework that I’ve operated as far as sections and how to organize it could be useful, but really it is about trying to be honest about what it is that make you succeed in relationship professionally are, frankly, otherwise. Somebody once wrote me and said that they love my user guide and they wrote one for their marriage. I thought that was kind of interesting to see. It really is about relationships and thinking about what those conditions are that build resonance, and then just felt disconnect between people. And then from there, it’s just about writing it all down and reading on it as you learn more about yourself and you know the way that you impact people and how people impact you.

Yeah. Excellent. Jay, we’ve titled this episode, Work Minus Disconnect. Why don’t you move back around to that and tell us why a user guide helps to erase disconnect from the world of work.

You know, I think people come to work every day with their best intentions. I fundamentally believe that people want to feel like, in their work environment, they’re succeeding. They want to feel like they come to work every day and they make an impact. That’s how we derive work as human beings in our professional lives. It is a big part of what makes us who we are. Unless you’re working in an entirely creative space that’s completely independent, and I can’t even think of really any profession where you don’t need to interact with other people. The quality and the richness of your impact is just a lot higher if you can create meaningful connection laterally with your manager, with your direct reports. And you’ll just feel better professionally in terms of the impact that you’re able to make. So I think if you can eliminate disconnect between people, you’ll just feel a lot more fulfilled and satisfied in your professional life.

Great. Jay, how often do you update your own user guide? Do you do it kind of as you have a significant interaction, you’ll go into your document and change it, or do you review it annually? What’s your process for that?

I’ll tell you that one section that does get updated more frequently than others and that’s the one that lists out all of my weaknesses. Because as I learn myself better, I realize just how broad I am and so I think it’s important to be honest about those things as you update that regularly. Call it every month or so, there’s something that I think and add. And not all of that is really useful. Sometimes it is just not necessarily useful for other people. It may just be useful for me to know how I’m showing up in any given interaction.

Jay, I really appreciate you being on the show, telling us about your user guides, work minus disconnects. Working people go to connect with you or if they want to view your user guide, where should they see that?

It’s on the First Round Review, which is a terrific publication. One of our investors is First Round Capital puts out this regular publication which is where they publish my user guide. They can contact me also at [email protected].

All right. Thanks a lot, Jay. This has been Work Minus Disconnect and we thank you for being on the show.

Thank you.