Thank you!

Jay Desai has FOMU. No, you read that right. As a first-time founder and CEO of health technology startup PatientPing, he’s got a healthy fear of messing up. This anxiety especially bubbles to the surface when it has to do with his team — now over 100 employees — and particularly the seven who report directly to him. He’s seen too many immensely talented and productive teams stall because of a subtle misunderstanding on how to best work with each other. After consecutive year-long searches for his Head of Product and Head of Operations, he didn’t want to squander that investment because he couldn’t figure out how to work with them.

So what did Desai do? He penned a user guide — similar to the kind that’d accompany a rice cooker or bassinet — but this one deconstructed how he operated optimally, when he might malfunction, and how others could use him to their greatest success. To create and the compile the guide took a intense self-reflection, drawing both from his early management mistakes at leading PatientPing and a career in finance (Parthenon Capital, Lehman Brothers) and healthcare (Centers for Medicare & Medicaid Services, CVS Health).

In this exclusive interview, Desai presents his user guide in full, complete with his defaults, directives and warnings across a dozen categories. The topics range from reporting to 1:1s and from an employee’s first 6 months to logistics. After each section, you’ll find Desai’s marginalia: his reflections on why these topics matter, and considerations should you author your own user guide. This is the most tactical framework for employee/manager communication that we’ve seen since Kim Scott’s flagship post on radical candor. Read on to learn from Desai’s example and start writing your own user guide for your team.

Yes, You Need a User Guide — Here’s Why

What’s the point of a user guide if you’ve got robust hiring practices, thorough onboarding, scheduled 1:1s, and continuous management training? The counterintuitive truth is that it’s the collaborative, more emotionally in-tune teams are actually most in need of user guides. “Ironically, I find that the fundamental disconnect between managers and employees comes from people being well-intentioned people-pleasers. This happens throughout the manager-employee relationship, but especially at the beginning,” says Desai. “While founders have a stubborn belief in how the world should be, they tend to be optimists who are willing to contort themselves to do things that people will like. Now, introduce a new hire who’s eager to fit in. Suddenly you have two people trying to make each other happy instead of being real with each other. You can see how this situation is primed for misunderstanding and miscues, despite best intentions.”

The goal of a user guide is to set blindingly clear expectations on how to collaborate without extra second guessing. The reality is that we all could use some level of assurance, regardless of how well we think we read people. “There’s upside even with the small first step of agreeing to create a user guide for your team. It’s an act of empathy, an acknowledgement of implicit power dynamics between managers and employees, and recognition that the group is made up of different people with distinct styles,” says Desai. “Then when you write one, the act speaks for itself. It says, ‘I know you want to make me happy and I want to make you happy, too, because I really want you to succeed. Let's just make that easier for each other by drawing a social contract on how we can relate. It helps us feel ok being ourselves without being misunderstood and a powerful tool to scale fast.’”

People always harp on the importance of building trust and communicating — but they rarely say how. Write your user guide. Ask your team to reciprocate. That’s how.

If Desai’s explanation still isn’t enough, here’s a list of quick hits on how user guides have helped PatientPing and him. (If you’re sold on user guides, skip to the next section.):

A user guide levels up the quality — and cuts down the quantity — of questions from your team. Exchanges become richer and more efficient.

The Deconstruction of A Real User Guide

Desai shared his current user guide with the Review so others could get a clear sense of the template, level of granularity, language and tone that’s worked for his team and him. Here we’ve separated his guide into sections, after which we’ve included his commentary. You’ll find a PDF of Desai’s full user guide and at the end of this article.

1. Communication

Desai’s Marginalia on Communication

2. Reporting

Desai’s Marginalia on Reporting

3. 1:1s

Desai’s Marginalia

4. First 6 months

I will invest heavily in building a trusting relationship with you in our first six months. Here are some tips for you to reciprocate:

Desai’s Marginalia

I’d rather get sophisticated questions than simple answers from new hires. People often don't think that asking questions is indicative of quick learning. They think it's the opposite.

5. Feedback from me to you

I commit to providing direct feedback.

The #1 way to succeed is to make measurable business impact that’s in-line with our mission and the company OKRs. I will measure your success by the business impact you make. If you’re not sure how your role or work output contributes to business impact and/or if it’s not clear how to measure it, do not proceed until we are aligned.

I try to make a practice of expressing gratitude nightly. If you’re exceeding my high expectations of you, I will share that with you both privately and publicly.

On the flipside, I am extremely passionate about our mission and may come off as combative because I will disagree and agree with you forcefully. Just in case it rubs you the wrong way (which inevitably will happen), it will be because:

(A) I’m so excited by the substance of our disagreement (ideal; and if our relationship is on stable footing, I suspect this will be the most enjoyable part of our work together).

(B) You did something that I felt was poorly constructed, incomplete, inadequate, or otherwise didn’t meet my expectations. We all have triggers that cause us to look unfavorably on our colleagues and these are mine:

(C) I’m frustrated with you because you have done parts of (B) multiple times and now I don’t trust you. If we’re here, I’ll nitpick, find issue with everything you do and it will be unpleasant for both of us. My frustration will be exacerbated because I’ll know it’s my fault, not yours. You are likely seeing this document at a point where we both made what we felt was the best decision with the information we collected during our interviews and made the determination that you, in this role, in this company, in this industry was right. I did reference checks, evaluated your track record, and know for a fact that you are talented and a highly capable executive. You did the same in your evaluation of us. If we get to this place, it’s because we’re not a good match. I’ll take responsibility and we’ll either look for a more suitable match or we’ll work on your exit.

(D) I am not listening well. If true, I may realize later and will apologize, particularly if you put down in writing what you were saying and I refer back and see I was the dummy. I respect you calling me out on this.

(E) I’m frustrated or scared about something unrelated to you, or am otherwise emotionally incomplete in that moment and I’m taking it out on you. If true, I’ll apologize because I’ll realize it later.

Desai’s Marginalia

PatientPing CEO Jay Desai

6. Feedback from you to me

Desai’s Marginalia

7. On micromanagement

Desai’s Marginalia

Trust-building shouldn’t be outsourced, but your inputs must go beyond firsthand experience at scale.

8. Me as a resource to you

Desai’s Marginalia

9. Professional Development

I try very hard to hire leaders that I would like to work for myself and are meaningfully better than me at the function you lead. As a result, it’s unlikely I will be a mentor to you in your role. My biggest value to you is to be a strong vocal advocate for your success, get you the resources you need to be successful, empower you to make impact without friction, remove any blockers to your success, lead and foster collaboration amongst the leadership team to align on a strategy that maximizes your impact, and surround you with a team of peers that inspire you.

You are the top person in the company in your function and my role as a mentor can be to:

I commit to doing all of these and expect you to hold me accountable if you don’t feel sufficiently supported.

I’m highly results-oriented and as a result, it’s not my first instinct to focus on professional development. I will do my best, but it will benefit you to clearly communicate your professional goals and I commit to supporting you.

Desai’s Marginalia

10. Hiring/Managing your team

Desai’s Marginalia

Buildings can share a zip code, but have different architecture. Define company-wide principles, but be open to cultural differences in teams.

11. Contribution to Strategy

Desai’s Marginalia

12. Logistics

Desai’s Marginalia

Desai's User Guide in Full

Here is Desai’s user guide in full, as of early 2018. It’s a dynamic document that he returns to to revise, as he learns more about himself and his team. Therefore, the following version is a snapshot in time — but a helpful template regardless.

The User Guide in Summary

To grow the company and as a leader, every manager at a startup needs to scale herself. At the end of the day, writing a user guide is an exercise in self-awareness. What teams want from their leaders more than anything else is predictability and authenticity. This leads to trust. With trust, you can be unstoppable. Give yourself a leg up and take the time to self-reflect, write and revise a user guide. If your founding team and early hires are friends or past colleagues — this is especially critical. Teams with history and good intentions frequently cross wires the most. Consider some of the themes of Desai’s user guide to get started: communication, reporting, the first 6 months, contributions to strategy, and separate sections for feedback (feedback from me to you, feedback from you to me), to name a few. Do this exercise first to set an example. Send it to others in advance so they can digest it on their own — and come back to you with questions. At its best, this tool generates self-awareness in leaders, helps with recruiting and serves as bedrock for working relationships throughout an growing organization.

“Not long ago, I noticed that my feedback conversations with colleagues differed depending on whether they joined before or after I’d written my user guide. For post-user guide colleagues, I could refer to it as a common reference point. We had fewer misunderstandings and more easily resolved the ones we did have. That wasn’t the case with those who started before I did this exercise. More explanation or context was required before getting to the meat of the issue,” says Desai. “I share this not just to show the impact of user guides, but to encourage founders to do this exercise early. When you’re the CEO, you’re leading a team of leaders. A user guide is not meant to ‘sell them’ on your way or inspire them like a set of values. It’s a statement of reverence. It respects their time, so you can get to the fun part of building a company together: the breakthroughs and rich professional relationships. Recently, our VP Growth created a user guide. He sent me his guide and all the feedback that he got from his team. I read it all. His guide’s meaningfully better than mine. And it’s working. That felt really good."

Hero image by pinkomelet/iStock/Getty Images Plus. Portrait courtesy of Jay Desai.

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