Note: Inspired by isn’t strong enough; this is the User’s Guide for Jay Desai customized for me and influenced by How to Rands.

Hi, welcome to the team. I’m excited that you’re here.

It’s going to take months to figure this place out, so this is a user’s guide for me that should help accelerate the process of getting to know each other and defining our working relationship. It captures what you can expect out of the average week working with me, how I like to work, my leadership principles, and my peculiarities.

[1. Communication] [2. Reporting] [3. 1:1s] [4. First 6 months] [5. Feedback from me to you] [6. Feedback from you to me] [7. On micromanagement] [8. Me as a resource to you] [9. Professional Development] [10. Hiring] [11. Contribution to Strategy] [12. Logistics]

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.

I think of written and verbal communications as orthogonal tools, and depending on the circumstances one is often 10 × better than the other. Verbal communication excels at back-and-forth. It’s a great way to get feedback on a large number of small decisions that all depend on each other, or to feel out my background or knowledge on a topic. Writing is better for capturing agreements, providing deep context, and broad dissemination.

Hierarchy of communications:

• Written, from most → least urgent: Text/iMessage → Hipchat/Slack/Skype → Email → Memo. Text whenever you want, I’ll turn on Do Not Disturb if necessary. I typically process email every few hours, but it might be a day before I see an email.

• Verbal from high → low bandwidth: in-person → Lifesize/FaceTime/Skype → phone. If I don’t answer the phone right away leave a voicemail or follow-up with a text and I’ll get back to you ASAP.

I like acknowledgement of written communications: a “got it”, plus, if it’s a task, an indication of where you put it in your stack, for my situational awareness. If it’s an FYI there’s no need to respond.

I will always make myself available if you need me. The best way to schedule time is on my calendar, which I check much more frequently than email and is intentionally open. I mark things private if they are, so feel free to ask me questions about things you see there. Since you can see where I am, if you’re scheduling something please allow for travel time if I need to change buildings. My default meeting duration is 27 minutes.

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. Adding a topic to our 1:1 agenda (see 3) works well for things that are important but not urgent.

My¹ definition of a meeting includes an agenda and/or intended purpose, an appropriate amount of productive attendees, and a responsible party running the meeting to a schedule. I prefer starting on time and ending early. If the purpose hasn’t been achieved we need to pivot the conversation before time is up to talk about next steps. If it’s not clear to me why I am in a meeting, I will ask for clarification on my attendance. If you send me something to read a reasonable amount of time before I’ll read it and likely provide more thoughtful feedback.

I expect you to close the loop on everything we open. Take things that are your responsibility off my plate and put them in your management/organization/prioritization system² that you create transparency around. I get frustrated when I have to ask about something twice or if I don’t know the status of your open loops.

Context is critical. I am interested in why you believe what you believe, so share your logic, particularly as we are building trust. Point to precedent, other industries, or if you’re reasoning from first principles, say that. It’s critically important we learn how each other think, so don’t worry about over-communicating.

Over-communicate when you have time and space, so that when you don’t, you can lean on those earned credits.

2. Reporting

Use your weekly report to provide status and communicate your priorities for the upcoming week. Read my report, those of your peers and any people who you’re managing or leading. This replaces an interminable weekly status meeting that would take thrice as long and have one-tenth the depth.

We will however have a weekly staff meeting with your peers. Instead of status it covers issues of substance that affect the whole team, and it’s guided by a shared agenda. I encourage you to add topics to this list.

Status individual tasks or projects on their respective tickets. Update your assignments ad hoc, but at least weekly. If you find that more than a quarter of your time is spent on work not captured by this system let’s talk, because something needs tweaking.

Once a quarter, we will review and update goals and formally document performance.

3. 1:1s

We’ll have 1:1s weekly or fortnightly. This is mostly your time and your agenda.

Between meetings, we’ll collaborate on and add notes to a running wiki page that’s private to us. Ultimately this becomes an archive of our prior conversations, and it will help avoid recency bias — whatever you did right before our 1:1 is not always the priority. The topic inventory is also immensely helpful during performance reviews.

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 conferences or other professional development, to discuss concerns from what you shared in your written reports or holes in the reporting, and for me to provide any missing context and bi-directional feedback.

Our 1:1s aren’t for status or tasking. I’m likely only one of many stakeholders invested in your work, and I believe peer accountability is more powerful than accountability to me. That’s why our reporting tools are widely visible: transparency is as important to those affected by your results is as it is to me.

This is the one meeting I don’t like to end early. If we run out of specific topics it’s a blessing that gives us the space to ask: How’s it going? What’s hot? What feedback do you have for me? How can I support you? Are you happy here?

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 (especially about baffling acronyms and terms that everyone else seems to understand). If you stop asking questions, that’s a red flag. Information will flow from me/others to you for the first couple weeks. 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 your specialty(ies), and over time we’ll learn from and teach each other based on the inputs we 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, and 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. Bonus: 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.

Time your goals in shorter increments early on so I can see you ramping up. For example, you’ll have quarterly goals, but share real-time wins/learnings; 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.

5. Feedback from me to you

I commit to providing direct feedback.

The #1 way to succeed is to make a measurable impact that’s in-line with our vision and the company’s goals. 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, then you and I are now equally responsible for fixing this.

I like to share, both publicly and privately, when you exceed my high expectations of you.

On the flip side, I am extremely passionate about our mission, I will not hesitate to argue with you when I disagree, and as a former debater I don’t tend to pull my punches. When I inevitably rub you the wrong way, it will be because:

(A) I’m 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 — these are mine:

• You aren’t connecting your work to our vision and goals. This doesn’t mean all valuable work is explicitly tasked from on high. In fact, I love when you can exist at 10,000 and 10 feet doing aligned and self-directed work. Don’t waste time on things that don’t matter. The best way to show passion for our mission is to work towards it.

• You’re showing a reluctance to take action or an instinctive aversion to risk. A bias for action is less scary when you communicate your decisions.

• You’re not meeting your commitments and delivering results. If this doesn’t occasionally happen we’re likely not being technically ambitious enough, but communicate early and often to avoid surprises.

• You disagree with something but don’t have the backbone to say so, or once a decision has been made aren’t willing to disagree and commit.

• You’re giving up too soon and aren’t showing enough grit. Reaching the first hurdle is a crappy reason to switch to a different race. Demonstrate creativity, resilience, and tenacity when confronting adversity.

• You aren’t addressing a problem at its root or are allowing yourself to be a slave to an ill-suited process instead of demanding that processes serve you. One reason I like wikis is because they empower everyone to fix small problems without asking for permission. Continually fix small things and demonstrate operational excellence.

• You are shirking responsibility rather than taking ownership. See the big picture and don’t fall into myopic or short-term thinking that’s more focused on your or your team than the mission.

• 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 insist on the highest standards for yourself and others.

• You aren’t fostering collaboration and a positive, upbeat environment. I love when you bring (realistic) optimism, humility, and most importantly, self-awareness to the team. Know your strengths and weaknesses, understand different social styles,³ and show empathy, compassion, assumed benevolence, and humanity. That’s how we earn the trust of others.

• If you do one of the above that causes me to react negatively, I’ll share my observation of your action and the effect it had on me, ask for your opinion, and then clarify the feedback. I’ll do this immediately if nobody else is there, after the meeting, or during our 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 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 highly capable. 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.

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 can be glib and hyperbolic and poo-poo good but avant garde ideas when I first hear them. I can be a sucker for trying new processes and tools when the old ones were not only working but superior. I can be both over-analytical and overly emotional in making decisions. I can be too long-winded, but other times neglect to provide critical context. I will ask you to do something that feels poorly defined, in which case you should ask me for both clarification and a call on importance because these questions can save everyone a lot of time. I swear sometimes. I can be stubbornly exacting about minute details that may seem insignificant in the big picture (especially grammar and punctuation), but to me represent high standards and attention to detail. When these details are indeed insignificant, my harping wastes our time. I can at times seem distant or unapproachable. My list of flaws is longer, as you’ll learn.

I try hard to hold myself to the same standards I hold my team (see 5B), but I value these standards because I need reminding too. I ask that you hold me as accountable to them as I will hold you. 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, if I’m the reason for your unhappiness but 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.

7. On micromanagement

I am hands-on until I trust you. I’ll poke at open your loops until I know you’ll close them on your own. 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. Leadership is service, so if we’re successful at building trust, our relationship will feel more like me supporting you than boss-manager (though I’ll be a manager 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.

Trust can also be built second-hand. Be awesome to your team and peers — I’ll hear about it.

8. Me as a resource to you

Be clear what you need from me for your success. Role, compensation, the organization, more feedback, more context, etc.

I love to work through problems together if it’s useful to you.

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. That said, being clear ≠ being slow.

9. Professional Development

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.

I don’t like hiring people who have the same expertise as me because it limits our ability to learn from each other. As a result, I’m unlikely to be a good mentor, but I can:

1. give you transparency into my role if you aspire to it, or something like it.
2. help connect you with people in my network.
3. change your role to help you change/increase your scope of responsibility/influence — if you are performing and if that’s your goal.
4. create an environment where you can perform and feel fulfilled.

I commit to doing all of these, and I 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.

10. Hiring

I like to involve the team in the recruiting and hiring process. I commit to transparency about the roles/skills we’re hiring for so that you can encourage high-performing people from your network to join our team.

When your expertise is relevant to assessing candidates I will try and include you in the process, and I’ll be as candid about the pipeline and status of candidates as I can be, within the bounds of confidentiality.

When we hire someone, this guide will help with their on-boarding, but nothing welcomes someone to a team like warmth and approachability from their new peers.

11. Contribution to Strategy

Our team meetings 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 when you have something to add. Be proactive in identifying new opportunities that propel the business forward.

12. Logistics

Tell me about your personal space boundaries. I will respect them. When you go on vacation, let me know where thing are at, how I can help, and what could go wrong.

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).

I work a bit on the weekends. This is my choice and I do not expect you to work on the weekend. I might email you, but it can wait until work begins for you on Monday unless I get ahold of you to say otherwise.

Be punctual.