The Indispensable Document for the Modern Manager

The Indispensable Document for the Modern Manager

To build the strongest teams from the get-go, PatientPing Co-founder and CEO Jay Desai has written the definitive user guide — on himself. Read on to see how his tactical framework creates the bedrock for productive employee/manager relationships.

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.

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 compile the guide took 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.

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 that 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 acknowledgment 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:

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.

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.

Desai’s Marginalia

5. Feedback from me to you

I commit to providing direct feedback.

Desai’s Marginalia

6. Feedback from you to me

Desai’s Marginalia

7. On micromanagement

Desai’s Marginalia

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.

Desai’s Marginalia

10. Hiring/Managing your team

Desai’s Marginalia

11. Contribution to Strategy

Desai’s Marginalia

12. Logistics

Desai’s Marginalia

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, which is essential to succeeding together.

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