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. 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.):

  • Show, not sell, transparency to candidates. “During the recruiting process, candidates will inevitably ask about culture. I usually say that I try to be transparent with who I am, what the company is, and what our values are. Of course, they’ve heard all that before from managers in their career,” says Desai. “Then I give them a preview of my user guide as a bit of an insight into our management style and to show we value self-awareness — and the collaboration that comes from it. Candidates find it illuminating to read, and helpful to see before making their choice about the role.”
  • Give new hires a full onboarding. “During onboarding, the first four days are heavily function and business-specific. On Friday, I have my first 1:1 with the new hire,” says Desai. “To prepare I send them my full user guide midweek, asking them to read it and come prepared to begin a discussion on how we will build trust. Their reaction is usually ‘This is great. I’m going to write my own companion user guide.’ They'll draft their guide and send it to me two weeks later. By the first month, we develop an understanding of each other that forms a strong foundation to get cranking.”
  • Redistribute cognitive overhead beyond the basics. “Time is finite — especially at a startup. Leveling up the types up questions I get means spending time on more difficult topics — and that’s typically where there’s more growth,” says Desai. “With a user guide, people don’t waste time wondering if they should respond when I forward an email as FYI or how to share business updates and so on. It’s all in the guide and so we can move quickly to more impactful discussions.”
  • Actually put your weaknesses on the table. “Many ‘thought leaders’ champion vulnerability and how it’s beneficial to get your weaknesses out in the open. But that’s obviously hard or more people would do it. When it’s on paper, they can learn and digest your weaknesses asynchronously, versus try to simultaneously absorb and react to what they’re hearing from you,” says Desai. “As the leader, it’s important that I share my weaknesses first — that I entrust others with it. That sets the tone that you’re going to be vulnerable as a manager. Show that you’re not perfect and make mistakes. Your employees will feel more empowered to do the same.”
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

  • I find that the vast majority of issues are a result of poor or infrequent communication. It’s important we communicate well and often.
  • Hierarchy of communication (most→ least urgent): Call→ Text→ Slack→ Email.
  • I like fast turnaround and acknowledgement on written communications. I like quick “got it” or “on it” type acknowledgment notes so I know things that we’re discussing are moving. If it’s an “FYI” there’s no need to respond.
  • I will always make myself available if you need me. I consider my time with my direct reports the most important time of my week. If you suggest a meeting or discussion, initiate finding time through Shayla or make an appointment on my calendar. If I suggest a discussion, I will initiate finding time. Don't say “let's discuss” without a follow-up of when we’ll discuss.
  • I don’t expect you to respond to everything in real-time, but do expect you to close the loop on everything we open. If it’s on my plate, I will do the same, but try to take things that are in your function off my plate and into your management/organization/prioritization system that you create transparency around. I get frustrated when I have to ask about something twice.
  • Frameworks and context are critical to sharing your work. I am always interested in the reason why you believe what you believe. All of us have a calculus by which we take in information and output a decision or position. Share your logic, particularly as we are building trust. Point to precedent, other industries, or if you’re reasoning from first principles, say that. Critically important we learn how we think so don’t worry about over-communicating.

Desai’s Marginalia on Communication

  • Get ahead of communication debt. “Communication is simply the accumulation of all your interactions, or in other words: your relationship,” says Desai. “It’s only when people are busy and communication becomes terse shorthand that you realize your ‘communication balance’ with others. Be thoughtful and over-communicate when you have time and space, so that when you don’t, you can lean on those earned ‘credits.’”
  • Factor in processing speeds. “There are at least two types of people when it comes to communication response time: real-time vs. gradual processors,” says Desai. “If a real-time processor is negotiating with a gradual processor, it can be frustrating unless expectations are set up front. As a real-time processor myself, I’ve learned to be patient when someone isn’t reacting in the moment and instead says ‘I hear you, and I want to give you a full, thoughtful response. Let me get back to you on Friday.’”

2. Reporting

  • Create a regular, systematic, clearly framed written process by which you share your progress against plan. Collaborate with me on this. Make it as quantitative as possible. Make the line between this, your OKRs, and the company OKRs clean.
  • Share this update no less frequently than weekly.
  • I place a high premium on data to describe your results.

Desai’s Marginalia on Reporting

  • Separate progress from plan. “Early-stage startups often sell the future: the product that’ll be built, the executive that will be hired and the customers about to sign. That optimism and ambition is often necessary to drive forward, but it should be balanced with consistent execution,” says Desai. “When you’re data-driven about results, there’s less room for interpretation. This helps with relationship- and trust-building as you can focus on what gets done, not how it’s getting done.”

3. 1:1s

  • Maintain a running Google Doc that we collaborate on.
  • This is mostly your time and your agenda.
  • I like using 1:1s to check-in on how you’re doing, what you need from me, personnel issues, broad strategy questions that we can seed/discuss, miscellaneous activities like speaking events or other professional development, discussing concerns from what you shared in your written progress reports or holes in the reporting, me providing any missing context from the board or elsewhere, and bi-directional feedback. Reviews of results against plan should be in writing and other forums (e.g. Product Review, Pipeline Review, Customer Health Review, etc) as I’m likely one of many stakeholders that’s invested in the performance of your function. I believe peer accountability around performance is more powerful than accountability to me so it’s more important that you create transparency to those affected by your results, in addition to me.
  • Once a quarter, we will formally document performance.

Desai’s Marginalia

  • Downplay recency bias. “For 1:1s, we use a running Google Doc that also serves as an archive of all our prior conversations. Because it’s easy to forget — both what you’ve talked about what’s been done,” says Desai. “I want to avoid recency bias — whatever they did right before our 1:1 is not always the priority. I ask reports to drop in notes over the course of the week. The topic inventory is also immensely helpful during performance reviews.”
  • No leading questions. “The questions to ask are simple: How’s it going? What’s hot? What feedback do you have for me? How can I support you? Are you happy here? These are open-ended inquires — invitations to say more,” says Desai. “I often hear people ask, ‘Everything good?’ That framing narrows the scope of the conversation. It’s really a statement: ‘Please say everything is good.’ That question is hoping for a ‘Yup. All’s ok.’ That’s not helpful for either of you.”

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:

  • Ask plenty of questions. If you stop asking questions, I will see that as a red flag. Information will flow from me/others to you for the first couple weeks and after that I will expect you to direct your learning as I won’t know what didn’t stick and what context you need that we didn’t provide.
  • This industry is complex and I can be most useful to you if you are proactive with your learning goals. I want to help you learn our industry and business, particularly early on. You will teach me about the function and over time, we’ll learn from and teach each other based on the inputs we each receive. It’s very fun when we reach the point where that information flows freely back and forth.
  • Making the prior point another way, if you don’t feel you need me to do your job well for the first 6 months, we will become misaligned as I’ll assume you aren’t working to grasp the context or are reacting to the wrong cues. I will be able to help you drown out the noise and amplify what’s important so we are aligned you're on the right path. As an added benefit, we will learn how each of us thinks, our proclivities, where and how we disagree, and how we collaborate. It’s important we do as much of this as we can early on.
  • Share your game plan. Time your goals in shorter increments early on so I can see you ramping up. For example, though you’ll have quarterly OKRs, share with me real-time wins/learnings, and as we progress, put up monthly wins/learnings. Soon quarterly wins/learnings will be the guts of our discussions.
  • Show me what you’re learning and what you still have to learn. Share your a-ha moments and outstanding questions.
  • It is impossible to over-communicate. Do not assume I know what you’re up to. If you’re ever debating including me on a communication, do it.

Desai’s Marginalia

  • Track the sophistication of new hires’ questions. “In the first six months, I pay most attention to the caliber of a new hire’s questions. Of course, I want them to rapidly demonstrate good judgment, but I can get a better sense of how fast they are learning from the questions they are asking at one, three, and six months,” says Desai. “For example, ‘Who are our customers?’ is more elementary than “How is this segment of customer different than the other?’ I’ll trust my employee faster if I can tell she’s increasing how fine the grain is on her questions as we go. When that happens, we’re on track.”
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:

  • You’re giving up too soon and aren’t showing enough grit. I love when you demonstrate creativity, resilience, and tenacity when confronting adversity.
  • You aren’t showing enough rigor. I love when you intensely evaluate the pertinent evidence, integrate that information from a wide range of sources, and apply sound judgment to make solid, smart decisions rapidly.
  • You aren’t connecting your work to impact on company OKRs. I love when you can exist at 10,000 and 10 feet and clearly organize your priorities against the company goals and in partnership with your key lateral interfaces. Don’t waste time on things that don’t matter.
  • You aren’t fostering collaboration and a positive, upbeat environment. I love when you bring (realistic) optimism, humility, and most importantly, self-awareness to your groups. Know your strengths and weaknesses, understand different social styles, and show empathy, compassion, assumed benevolence, and humanity.
  • You are shirking responsibility and not acting like an owner. Be an agent for the change you want to make at this company and show fearlessness. It’s ok to fail and take calculated risks. Speak your mind when something is broken and pair it with clever solutions.
  • You aren’t engaging in your own learning and teaching. A thread that binds us together is curiosity — about our industry, business, customers, function, and perhaps most importantly, about ourselves.
  • You aren’t showing enough leadership or investment in engaging your team. Internalize our company mission and connect it to your team’s, communicate and evangelize it often, always make recruiting exceptional talent your top priority, build morale, career-ladder your team, deliver clear feedback, design your org to scale for 12-18 months, attack conflict swiftly, and be proactive with resolution.
  • If you do one of the above that causes me to react negatively, I’ll share my observation of your action, the effect it had on me, ask for your opinion, and then clarify the feedback. I’ll do this either immediately if nobody else is there, after the meeting, or during our weekly 1:1. If we are aligned about the issue, I expect that you will acknowledge, mitigate and resolve the situation swiftly.

(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

  • Take note — and track — your triggers. “Everyone has a bias for what they consider outperformance or, reciprocally, the traits that set you off. I was able to compile this section quickly because they represent the behaviors that were triggers for me with prior direct reports,” says Desai. “I did a bad job communicating my expectations before this user guide and did everyone involved a disservice. The key is to learn from it. Codify the lessons. Otherwise history repeats itself and it’s important when it’s people’s dignity — and your company — at stake.”
PatientPing CEO Jay Desai

6. Feedback from you to me

  • Commit to providing me direct feedback when I’m blocking your or the company’s success.
  • I am flawed. I'm not great at process. I can be bursty. I sometimes leap to conclusions, rally people around it, then backtrack. I can go into a hole when strategizing. I put together frameworks that I don't hang on to for very long. I'm a workaholic and will work at odd hours.
  • Sometimes I'm slow to fully grasp a new point or don’t listen well because I’m stuck on an idea. I can be over-analytical and slow to act on some opportunities and impulsive about other opportunities. I can be too long-winded. I often get proded by external stakeholders (board, investors, customers, competitors, others) and may forget to describe the context to any given paranoid moment that I take out on you. I can be stubbornly exacting about minute details that may seem insignificant in the big picture, but to me represent an upholding of our values/standards, but the details are indeed insignificant and, as a result, we waste time. My list of flaws is longer as you’ll learn.
  • I try hard to hold myself to the same standards I hold my team to (see 5B), but don’t always do this well. Sometimes it will feel like a double-standard where I expect you to be a certain way but I am not that way myself. I beat myself up about my misgivings and seek continual self-improvement but despite my weaknesses, have become more comfortable in my skin as I've matured as an executive as this confidence helps us go faster. I like when my team helps make me better.
  • I respond well to feedback. I don’t like yes-men/women and after we establish a healthy trusting relationship, you will be rewarded if you give me feedback on how I can better support you and the company. Our relationship will get better if you do this well.
  • I encourage you be clear with me on how I can best work for you. Consider writing a user guide like this for yourself as I will honor it (or tell you if/when I can’t). Through our relationship, I will work to understand your style and how you’re best supported. I would be insincere if I didn’t admit that if our friction is sizable, it’s likely that you’ll need to adjust to my style more than I’ll adjust to yours. That said, I recognize this is the first time I’m a CEO and I am working hard to be better. If I’m the reason for your unhappiness and you don’t sense that I’m unhappy with you, give me a chance to improve.
  • I will do my best to tell you if I’m able to meet you where you are or if I will just let you down. Do this instead of surprise quitting or letting your discontent fester.
  • I try to be self-aware about my own performance and have committed to the board that I will proactively evacuate my post as CEO if I am no longer useful to this company (though that may not be my choice).

Desai’s Marginalia

  • Praise direct feedback that’s complete. “The people on my team have taken my openness to feedback to heart — they know I want it. I really try to get to the place where people feel very comfortable just saying whatever they want to say, but the truth is, even I want feedback a certain way,” says Desai. “If I do something that’s thoughtless or careless, it may not be constructive to say, ‘I think you’re offensive.’ Even if that’s the case, it may not be not useful. I’d prefer ‘When you said X, I felt offended and noticed that others became uncomfortable.’ That’s more compassionate, complete feedback.”

7. On micromanagement

  • I am hands-on until I trust you. Once I trust you, I’m hands-off and we’ll collaborate as you need me or when I bring you ideas for us to work through together. Our relationship will feel more like a partnership or me supporting you than boss-manager if we’re successful at building trust (though I will be in the manager role when needed.)
  • From there, if I get in your hair again, it’s because I’m losing trust in you or don't feel like we are making adequate progress on a given topic, likely because you are not satisfying my need for Communication, Reporting, or are doing things in 5B.

Desai’s Marginalia

  • Trust can be built second-hand. “I’m often more interested in how trust is building peer-to-peer than between me and my directs,” says Desai. “For example, when my growth leader says good things about his product counterpart, it makes me trust my product leader more, and vice-a-versa.”
  • Point to section 5 when you start to micromanage. “It’s important to intervene early as soon as you recognize that you’re starting to lost trust in a report. Micromanagement is a great trigger that this is happening,” says Desai. “That’s when I tell them I'm starting to lose confidence in them. Then, I refer them to section 5 of the User Guide as a tool to diagnose why trust may be deteriorating — then we talk about it. That intervention is necessary because, once the trust is fully gone, I haven't yet had an example where I've been able to regain it.”
Trust-building shouldn’t be outsourced, but your inputs must go beyond firsthand experience at scale.

8. Me as a resource to you

  • Be clear what you need from me for your success. Role, comp, org change, more feedback, more context, more board interaction, etc.
  • Be clear when you need the company’s resources. Be data-driven about why you need it, gather alignment from the pertinent stakeholders, and show that you’re being cost conscious. I like justifications that include, “this is what [company we respect] does” + “this is the ROI” + “this is what an experiment would cost and if it works, from there I can shut it down or scale it up” + “this is the most cost-effective solution for these reasons.” Develop a nose for value and bargain-hunt.
  • I love to work through problems together if it’s useful to you.

Desai’s Marginalia

  • To be clear is to give context. “Compare these two statements: ‘Hey, I'm really enjoying my work and I'm excited about having more opportunity in the future.’ Now this one: ‘Hey, I feel like I've done a great job in this role. I'm at a level eight. What would it take for me to get to a level nine? That’s my goal and I feel like I’m acting at a level 9 right now. I've had an interest in doing marketing or operations, in addition to sales. What would it really take for me to extend my scope to that? My personal career goal is to be a COO,’” says Desai. “The first has intent. The second has clarity. To be a resource to you, your personal context in our shared company language goes a long way.”

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:

  • 1) give you transparency into my role if you endeavor to become a CEO/founder.
  • 2) help connect you with people at other companies that are leaders in your function.
  • 3) change your role to help you change/increase your scope of responsibility/influence if you are performing and that is your goal.
  • 4) create an environment where you can perform and feel fulfilled.

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

  • Debunk the default belief that a leader is a mentor. “It took me a while to realize this, but a lot of founders believe they need to be mentors for their reports,” says Desai. “The role of the CEO or founder means wearing many hats, and it may be hard for the mentor hat to be one of them — especially if you’re hiring people more senior or experienced than you. If you try, it will be inauthentic. A CEO can be many things to their manager to be supportive, and mentor may not be one of them. It’s hard for leaders to admit that, but it’s an important distinction — and decision — to make.”

10. Hiring/Managing your team

  • Collaborate with me closely on your org structure design.
  • Collaborate with me on your new hires, particularly levels 4+. These are ultimately your decision, but I hold veto power (that I will use judiciously). I will want more involvement in your first hire, than your second, than your third, than your fourth, etc. One of your most important jobs is to recruit incredibly high quality talent, particularly at the level 4+. These people should be better than you at the function for which you’re hiring them and in the same way I want to hire people that I would work for, it works best when you aspire for the same from your directs.
  • Share with me your team management system—how you communicate the vision, set goals, create alignment, foster high engagement, and cultural nuances/recruiting practices/performance review processes that are unique to your team.
  • I’ll push you to push out poor performers and get frustrated when we take too long to act. Be fair with terminations— take responsibility that you (or your predecessor) made a mistake hiring them, and don’t surprise your employees that they are being let go.
  • Recognize and support your top performers lavishly. Help me help you recognize your top performers.
  • Don’t let your CultureAmp results be a surprise.
  • Don’t surprise me with employee departures. We should know about these before they happen.
  • Pay median compensation, have a good pulse on market compensation, learn how to communicate the value of equity at offer, pay close attention to diversity/inclusion in all aspects of team function.
  • Know the tech talent ecosystem and where the best talent resides. Don’t rely solely on our internal recruiters to hit your hiring goals.
  • Refer to these attributes when hiring (some of this was substrate for above) and I like this for performance management.

Desai’s Marginalia

  • Be explicit about team norms that aren’t held companywide. “There’s a lot of literature about how different organizational silos form and the importance of company-wide principles. That’s true, but you must trust your leaders to know what’s best for their team and their culture, too,” says Desai. “It’s okay if some norms differ between teams. Just be explicit about it and make sure they don’t collide with company values. For example, some teams may telework more than others and that’s fine.”
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

  • Our leadership discussions are a critical time. Be engaged, don’t multitask, keep up with the pace of the discussion, work to grasp the nuances, and participate actively.
  • Contribute to the collective knowledge of this company by sharing your thoughts in the #reading-room or responding to open threads when you have something to add. It's important the team feels leadership is engaged in knowledge building.
  • Be proactive in identifying new opportunities that propel the business forward. It’s not enough to just wear your functional hat in strategy discussions. This is a time for you to take off your functional hat and own the overall company strategy.

Desai’s Marginalia

  • Collect, then curate strategic suggestions. “The challenge at an early-stage startup is that people don’t often have time to get outside their role. It’s not desire or capability. It’s that they’re dialed-in to hit their next milestone,” says Desai. “If they have the idea for a new strategy, maybe an idea they got from their Twitter feed, make sure they have a place to deposit it in a low-lift way. It could be a Slack channel or Google doc, but make sure it’s searchable and that the team reviews at a regular cadence. Otherwise, they’ll learn it’s not worth their time, and you’ll lose engagement and some potentially good ideas.”

12. Logistics

  • Tell me about your personal space boundaries. I will respect them.
  • I like to have open-ended conversations after-hours. Between 6-10PM is when I like to talk through things so I may call you at that time unannounced. If you prefer I text or check your availability first, tell me.
  • I like getting together over dinner/drinks after work for longer-form, open-ended discussions.
  • I try to take one day off on the weekends to recharge (usually Saturday), but am usually available during the weekends.
  • I can talk anytime (24x7) if something is urgent.
  • When you go on vacation, let me know how I can help or what could go wrong. It’s unusual when we feel we can leave for longer than 10 days, but I trust you to do that if you can.
  • Keep your calendar current, make your calendar responses status accurate (i.e. don’t accept meetings you can’t attend, say tentative if not sure).
  • Be punctual.

Desai’s Marginalia

  • Don’t skip the afterhours communication component. “Outlining how communication happens during the evenings and weekends is a really good way to draw out how each of you can respect one another's personal space — something that can result in tension and frustration,” says Desai. “People romanticize Steve Jobs or Reed Hastings calling them at 2am. I don't buy that. I think it's important to pay deference to your team's personal life, and that starts by explicitly writing down expectations.”

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.