User Guide to Working with Me

Welcome to my User Guide to Working with me! I offer this to you because I recognize that the faster we get to know each other and how we work, the better and stronger our relationship will be, and the more we’ll accomplish together. I encourage you to write your own User Guide so I and your team can learn how to work best with you. This is a living document that will change as I learn more about myself and how we can best support each other.

Communication

1. I find that the vast majority of issues are a result of poor or infrequent communication. It’s important we communicate well and often.
2. Hierarchy of communication (most→ least urgent): Call→ Text→ Slack→Email.
3. 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.
4. 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.
5. 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
6. 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.

Reporting

1. 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.
2. Share this update no less frequently than weekly.
3. I place a high premium on data to describe your results.

1:1s

1. Maintain a running Google Doc that we collaborate on.
2. This is mostly your time and your agenda.
3. 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.
4. Once a quarter, we will formally document performance.

First 6 months

1. I will invest heavily in building a trusting relationship with you in our first six months. Here are some tips for you to reciprocate:
2. 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.
3. 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.
4. 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.
5. Show me what you’re learning and what you still have to learn. Share your a-ha moments and outstanding questions.
6. 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.

Feedback from me to you

1. I commit to providing direct feedback.
2. 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.
3. 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!
4. On the flip side, 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:
5. You’re giving up too soon and aren’t showing enough grit. I love when you demonstrate creativity, resilience, and tenacity when confronting adversity.
6. 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.
7. 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.
8. 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.
9. 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 solutions.
10. 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
11. 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
12. 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 an 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.

Feedback from you to me

1. Commit to providing me direct feedback when I’m blocking your or the company’s success.
2. 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 prodded 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.
3. 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.
4. 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.
5. 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.
6. 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).

On micromanagement

1. 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)
2. 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
3. Me as a Resource to you
4. Be clear what you need from me for your success. Role, comp, org change, more feedback, more context, more board interaction, etc.
5. 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.
6. I love to work through problems together if it’s useful to you.

Professional Development

1. 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 our 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.
2. 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

Hiring/Managing your team

1. Collaborate with me closely on your org structure design.
2. 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.
3. 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.
4. 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.
5. Recognize and support your top performers lavishly. Help me help you recognize your top performers.
6. Don’t let your CultureAmp results be a surprise.
7. Don’t surprise me with employee departures. We should know about these before they happen.
8. 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.
9. Know the tech talent ecosystem and where the best talent resides. Don’t rely solely on our internal recruiters to hit your hiring goals.
10. Refer to these attributes when hiring (some of this was substrate for above) and I like this for performance management.

Contribution to Strategy

1. 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.
2. 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.
3. 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.

Logistics

1. Tell me about your personal space boundaries. I will respect them
2. I like to have open-ended conversations after-hours. Between 6-10p 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
3. I like getting together over dinner/drinks after work for longer form, open-ended discussions
4. I try to take one day off on the weekends to recharge (usually Saturday), but am usually available during the weekends
5. I can talk anytime (24x7) if something is urgent
6. 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
7. Keep your calendar current, make your calendar responses status accurate (ie- don’t accept meetings you can’t attend, say tentative if not sure)
8. Be punctual