👋 tl;dr: A user guide to working with me

Being a CEO is the dream of a lifetime for me. I care deeply about being a great one. My goal is to earn and retain your trust and respect—and for you to earn and retain mine.

This is a guide to how I operate. It’s intended to provide extreme transparency so you can succeed in getting what you need and request from me. It’s a living doc, so please “suggest changes” to comment or add in something for others’ benefit!

📺 Communicating with me

Channels

• For important things <500 words: Email
• For important things >500 words: Almanac Doc
• For simple urgent things: Text/Call (201-341-4335)
• For complex urgent things: Meetings
• For casual questions or updates: Slack
• Note: Assume I don’t see 50% of what you Slack to me. If me forgetting or not responding is not OK, use a different channel!

Time

• I treat my time, and therefore my calendar, as a reflection of my priorities. I shift things around frequently as I assess where my focus is best allocated day-to-day.
• I will try to be respectful of your time and keep our normal slots for 1:1s and such, but apologies in advance if it moves. If it’s annoying you, tell me.
• If I suggest meeting, I’ll generally find a time on your calendar. I expect the same of you: if you need an urgent decision from me, schedule some time.

Style

• In verbal or written form, start direct with your update or ask. Keep context to 1-2 lines max. Then, follow with supporting points or details.
• As part of my inclination towards systems thinking, I’m interested in the “why” behind your idea / conclusion / update / ask.
• Best way to convince me: analyzed data
• Also really good: frameworks and heuristics
• If we are struggling to align on something, lean in. Communicate more frequently, add in more detail. I’ll notice, and make a similar effort.

Following up

• We’re building an async company, so I don’t expect real-time responses on everything. If I do, I’ll call or text you.
• I do expect you to close the loop on important docs or emails within 24 hours of receipt:
• If I send an email to inform you, I like a “received” or “looking at it”
• If I ask for something in an email, doc, or comment, ideally with an “on it” and a time expectation on turnaround
• I will do the same any time you send or ask something of me!
• As part of managing me, I expect you to proactively communicate with me, especially around the priorities we’ve agreed for you or your team’s work. That includes regular status updates, blockers, and wins.
• I get frustrated when I have to repeatedly ask for an update on things I’ve asked of you and you’ve agreed to.

⛵ Reporting to me

1:1s

• I like to meet at least once a week with you.
• We should have an Almanac doc with notes from all of our 1:1s. Each meeting should end with a list of tasks.
• I like when you bring a written agenda in our doc to our 1:1s. It should include:
• Metric-based status updates on your priorities
• Strategic things you’d like to think through with me
• Blockers I can lift to speed you up, empower you, or make your life easier
• How you’re doing and feeling
• If you don’t have an agenda, here’s the questions I will default to asking you: Internal CEO/Employee 1:1s at Almanac
• I always end with “Do you have any feedback for me?”
• If all is fine, that’s great!
• But please be candid and specific if you do have feedback.

Strategy

• I have a strategy background, and so at the very least I’d like to be involved in co-creating your team’s strategy with you. I will never be hands off around strategy.
• Aligning on strategy for your department is an ongoing process, though every 6 months as an exec team we will pull up to reevaluate the company’s direction.
• At least until we find product/market fit, I think about our company in a wartime stance. We’re trying to do an ambitious thing in a fast-moving market with limited resources and tough competition. I see my #1 job as getting us all swimming in the same direction.
• Therefore, I expect the strategy for your team to align with our company vision and six-month strategy.
• If you want to deviate from our company strategy, that implies you have concerns about the overall direction. Come prepared to chat with data or frameworks, because I will naturally push back. I’ve been convinced to shift direction by the team many times since we started Almanac, so you might be right!
• I believe strategy means focus, and focus means tradeoffs. Your highest value add strategically is to help us make tradeoffs. Start with outlining the options or the stakes—you don’t always need to make the decision yourself.

Priorities & Tracking

• If you’re a team leader, I expect you to report weekly, via metrics, on your monthly priorities.
• This should happen in our 1:1s, and likely at our All Hands in front of the whole team.
• We set monthly priorities as an exec team (we call them OKRs). You’ll be assigned some as the Directly Responsible Individual. Some functions, like engineering or customer service, have more implicit priorities around fulfillment that supports our broader goals.
• I expect you to have at most 1-2 documents/databases/spreadsheets that are single sources of truth for your department.
• Pet peeves around data:
• Complex SaaS tools that aren’t easily adjustable. Just use Mode, Airtable, Sheets/Slides, or an Almanac Doc!
• Information that isn’t analyzed, and data in different places.
• Don’t wait for me to ask how it’s going! Proactively communicate status, wins, and blockers. I will get irritated if I have to follow up on a specific ask I made.

Resources

• We must return the funds we raised for Almanac 10x+ to our investors. Our money is not free, it did not magically appear, and it is not endless.
• If you need resources (budget, new people, overhead expenses):
• Whenever possible, model out the return on investment (using numbers).
• Show 2-3 alternatives to your recommendation; it’s great when you do some research.
• Include benchmarks from other high-performing companies.
• Treat it like an experiment: “if X happens we should scale; if Y happens it failed and we can shut it down.”
• Show me you’re being cost-conscious and value-oriented.
• I love doing this kind of work with you; we can always partner on the WIP analysis (and as long as I own the company budget, you’ll eventually need to pass the forecast to me).

Onboarding

• First: if we’re working together, I think you’re amazing, and better at your job than I could be if I were doing it. Starting a new job can be nerve-wracking, but know I’m so glad you’re on our team. 😃
• In your first 4 weeks, your main task is to listen and observe how we do things. There will be time later to give me feedback and start improving things—that’s why you’re here after all—but it’s best to understand first and build trusting, respectful relationships. You risk that if you try to change things too soon that your peers have built and whose faults they often know best!
• I will often start you off with some initial projects to help you get your feet wet. This is intentional, and not about a lack of trust. If things are going well, you’ll move quickly to the deep end.
• I believe trust is at the core of healthy relationships, and you’ll know you have mine if I start to communicate less frequently. I still expect you to communicate proactively to me (see above).
• In your first 4 weeks, we’ll find an hour to talk about your professional development goals. The template is here.
• After 4 weeks, we do a culture diagnostic; your fresh eyes help us understand how our culture looks to an outsider. It’s not a test, but rather feedback for us. The template is here.

⛰️ Professional Development

• More than anything Almanac can pay you, I believe what you learn and how you grow during your time here is our best form of compensation. It lasts for life, it compounds with experience, and it passes on to everyone you touch.
• I try very hard to hire people who I’d like to work for myself, and who are meaningfully better than me at the technical aspects of their jobs. It’s unlikely I can be a hard skills mentor to you in your role. Please treat my ignorance kindly.
• Coaching & mentoring is one of my strengths, and I get a lot of energy from helping you grow as a general manager and leader. Please engage me on any management challenges you’re facing; I love workshopping them with you!
• How I commit to helping you succeed:
• Being a true advocate for your growth and success at Almanac and beyond
• Providing you with a vision and mission that inspires you to do your best
• Surrounding you with a team and culture that push you to do even better
• Getting you the resources you need to succeed and removing blockers in your way
• Creating an accountability system that empowers you to make a huge impact with minimal overhead and friction
• Tactical things I can do to help you grow even faster:
• Give you ever more ambitious goals or more challenging opportunities, should you request them and are ready for them
• Connect you to benchmark organizations and leaders with whom you can commune as peers
• Consistently providing you with positive and constructive feedback (see below)

⛷️ Feedback

Feedback is hard! I strongly encourage you to read Radical Candor; Almanac will reimburse you for it. It’s the best book on the topic of interpersonal relationships at work.

From you to me

• I gain my energy, and my authority, from your trust and respect. I make many decisions in our relationship around earning and keeping yours. And it’s a huge source of anxiety for me when I sense I don’t have it—I literally lose sleep.
• Candor is an Almanac virtue, so you should commit to providing me radically candid feedback when I’m blocking our success. That means:
• Showing that you trust, respect, and care for me personally
• Challenging me directly, armed with data or frameworks
• I love constructive feedback…
• When I’ve assigned or asked for too much work
• When I’m diluting focus for the team or creating directional confusion
• When our metrics are too ambitious or deadlines are unrealistic
• When the priorities or sequencing don’t make sense
• When I’ve said the wrong thing, or a thing in the wrong way
• When you feel I’ve done something in conflict with our virtues
• I am human, I am flawed. Sometimes, CEOs are perceived as superhuman; I promise I am not as good or as bad as it may seem. Please think about how you give feedback.
• I don’t believe in shit sandwiches; no need to sugarcoat it. Instead, try empathy and showing that you made an effort to understand why I did what I did.
• The best tactic for good feedback conversations: repeating back what I just said to you before sharing your next thought. Works every time.
• Feedback can be positive! If I do something well, please tell me—and be specific. Positive affirmation is one of my love languages, and it gives me so much energy when I succeed at something I work hard at. 🌟
• Positive relationships typically have a 5 positive : 1 negative feedback ratio. Let’s try for that.
• I care about your feedback, and am very serious about responding to it. I hope I’m so good at this you list it as a strength in my 360 review. I don’t like yes people; I want you to make Almanac iconic and push me to up my game. If you give great feedback in the right way, you’ll be rewarded and our relationship will grow stronger.
• Be clear with me on how I can best work for you. This specifically means changes to your role, responsibilities, opportunities, compensation, feedback levels, business context, interactions with team, board, or customers.
• I ask about your needs and preferences in our initial professional development conversation, but be proactive if there’s anything I can do to support you better.
• When you succeed, Almanac does too. If it’s helpful, consider writing a user guide like this for yourself.

From me to you

• You gain my trust and respect from 1) delivering on your priorities 2) in alignment with our vision and virtues. Both are essential. If you deliver results but are a jerk to me or others, or want to build a different business, you likely aren’t a fit for Almanac.
• I love it when you succeed, in both small tactical settings (you made a great comment, you managed a situation well) and big strategic ways (you nailed your OKRs). I often recognize it (publicly or privately). Specifically, I love seeing behaviors aligned with my values and Almanac’s virtues:
• Speed
• Passion
• Intelligence
• Creativity
• Bandwidth
• Resilience
• I will also give you constructive feedback. Themes might include:
• You are doing work that’s not aligned with our vision. We need to be swimming in the same direction.
• You’re giving up too soon or not demonstrating tenacity. Startups win often just by not giving up. To change my mind, bring data or a framework.
• You’re producing low quality work. Laziness is unacceptable. I will assume you don’t care enough to put in the time. The alternative is even worse.
• You aren’t showing enough intellectual rigor. I love it when you make decisions using the best available internal data and external wisdom and combine them into first-rate analysis. If your decision is off by 2 degrees, we’ll lose by a mile.
• You aren’t displaying curiosity or a learning mindset, which often looks like being too sure of your own conclusions without expressing risks or doubt.
• You’re not acting like an owner. If it’s broke and you can fix it, fix it. Please don’t complain to me without proposing a solution.
• If when leading a team, you’re not showing positive energy and enthusiasm for our mission. Startups are inherently scary, and it’s your job to manufacture momentum for those around you.
• You’re not proactively communicating with me. If you miss a goal and I hadn’t heard about it before the finish line, it’s on you.
• I typically try to give feedback, within one week, in the following format:
• First, I share the facts of what happened from my perspective.
• Then, I express the effect it had on me and why it matters.
• Finally, I end with a request.
• I will ask for your thoughts or feelings, repeat them back so you know I heard you, and then clarify the feedback or request.
• In giving you feedback, I will inevitably rub you the wrong way or hurt your feelings. Know my intent is to help you be better, because I care about you.
• We have an autonomy-driven culture where trust is the lifeblood of our work together. If I lose trust in you, you’ll know it because it will feel like I’m micromanaging. This can be solved by being proactively communicating how you’re fixing the thing.

🏓 For Almanac Execs

Contributing to the Exec team

• The executive team is actually your FIRST team. Our ability to converge on an aligned plan is the highest-leverage activity we can do to produce company-wide results.
• Cohesion amongst us vibrates throughout the company, as does tension. It’s not just my responsibility to create positive outcomes on the Exec team; it’s yours too.
• Our Exec meetings are a critical time. I expect you to:
• Pay attention and not multitask
• Listen deeply, be empathetic, work to grasp the nuances, and reflect back
• Be engaged and participate verbally; if you’re quiet, I assume:
• You’re frustrated and don’t agree, and will provide feedback to me later
• You agree and don’t want to waste time -> ping me
• As an Exec team member, I expect you to:
• Feel responsibility for our company strategy
• Help find the quickest path to our goals
• Document everything your team does in the handbook

Managing your team

• I want to continually uplevel our team and ensure we have stunning colleagues; I will:
• Help you recruit for your open slots, including selling the shit out of our vision
• Push you to transition out low performers—and will get frustrated when we take too long to act
• Encourage you to reward our rockstars and superstars with public/private feedback, increasing responsibility, and higher compensation
• Help you craft employee departures and communications to the rest of the team, including me taking responsibility for the decision
• Get you get an executive coach - I believe we should all have them, and we are considering having Almanac cover their costs in 2021
• In return, I expect you to:
• Collaborate with me closely on the design of your team’s structure
• Involve me deeply in any recruiting process for your open roles
• Never surprise me with personnel or culture issues
• Create and update your team’s handbook:
• Your team’s mission, vision, and values
• Your team’s strategy and priorities and current metrics
• Your team’s processes
• Your team’s cultural norms

🏄‍♂️ My management style

🙏 My values

My values drive everything I do: how I use my time, how I make decisions, and how I interact with others:

• Impact
• Excellence
• Ambition
• Creativity
• Play
• Adventure
• Community

💪 My strengths

• I practice trying to see around the bend and imagining how things could be. I’m inherently optimistic about ideas, companies, and people. Pursuing bold, even crazy, goals gives me a ton of energy. People have told me I can create “reality distortion fields” that motivate and inspire them.
• I care deeply about the things I’m involved in and the people I surround myself with. I spend many of my free moments thinking about their (your!) success.
• I’m a systems thinker; I enjoy examining the many facets of a problem, product, or person to understand the why, the how, and the so what.
• Ownership is my MO; I often dive into head-first, especially if I’m asking others to.
• I can move easily between operating creatively and strategically at a high level, and tactically and practically in the weeds.
• I can communicate fairly well, which I think is about taking complex and confusing concepts and making them simple and compelling.
• I have extremely high-bandwidth; I can do a lot of high-quality work very quickly and in parallel. I have a lot of persistence.
• I have high standards and hold others to them, which has frequently resulted in people growing and doing more than they thought they could around me.
• I appreciate nuance, and can hold two conflicting ideas in my head at once.
• I’m outgoing and social. I’d spend every waking moment with other people if I could, and really enjoy getting into collaborative flow with teams.
• I can “turn it off” and know how to enjoy myself, which I do through a fairly full life of social dinners, travel, skiing, surfing, biking, reading, and movies.

😧 My weaknesses

First, some helpful context. I used to competitively ski race. The sport involves hitting as many poles as possible as quickly as possible—while flying down an icy slope on thin metal edges. All that practice has become part of my approach to work and life, which can lead to:

• Taking on more than I can handle—and asking others to do the same. If I ask for too much, propose a choice and outline the tradeoffs for me.
• Being unreasonably optimistic around what’s possible, and leaning hard into promising ideas. I also might come across as more sure than I actually am. If you’re unsure, ask!
• Having unreasonable expectations around timing. I want to win as soon as possible.
• Trying to will performance or results into existence through sheer effort. If something’s not working, I often get more involved, or try to do it myself.
• Accumulating, versus mitigating, risk. When something’s not working, my tendency can be to add or try something new v. fixing the thing that’s broken.
• Getting frustrated when there’s tension or lack of alignment.

Some of these qualities can make a good entrepreneur, but they also have a dark side if not applied correctly. If you feel I cross the line on any of these, please give me feedback (see above) or jokingly call me out by saying, “Adam, this isn’t skiing!”

An important interpersonal weakness to be aware of:

• When I perceive a gap between the things I’m responsible for and the things I control, my emotions can take over and I can become a bad collaborator. If I seem this way, the best thing you can do is help me feel a sense of control again.
• If you lose my trust or respect, I may come across as withholding or condescending. Difficult as it is, please call me out on it so we can talk it through. It’s likely fixable.

“I am human” disclaimers:

• I am flawed. I am frequently wrong. I can be inconsiderate. I sometimes say the wrong thing. Please forgive me.
• I’m working on it. I spend many hours a week with a community of people—my therapist, executive coach, personal trainer, mentors, friends—trying to become a better me.
• I’m grateful for your help. The best thing you can do is offer me radically candid feedback.

Sustainability rainbow

With my executive coach, I often use a color code to communicate how I’m doing. This helps to contextualize everything I say afterwards with my emotional state. I’m sharing this for transparency; feel free to ask me how I’m doing, or share where you are during a 1:1!

• Blue: Truly living in the moment, present, balanced, weightless.
• Green: Energized, happy, flow state. Helping other people be their best.
• Yellow: Some stress, but manageable, nothing totally broken, most important things done, didn’t cause anyone serious delay.
• Orange: Incapable of doing deep work, basic functioning, might be able to get 1 personal thing done. Might be causing someone a delay.
• Red: Cognitive delays, borderline burnout, definitely not serving the team well.
• Dark Red: Depressed, need time off.

🍸 Logistics

• I assess whether a day was good or bad based on if I can workout. Please encourage me to close my computer and get outside, mainly by respecting my exercise blocks.
• I’m bad at Slack (and text). Sorry.
• I think everyone has a “baby”: a real human to take care of, or a passion, or a priority. Tell me what it is and I will respect it.
• I love flow-state conversations: about Almanac, startups, skiing/surfing, politics, airlines, design, movies/TV, or anything else. My favorite 1:1s are when we get into this place.
• For anything urgent, I’m available 24/7. I’m here for you!

Script: Internal CEO/Employee 1:1s at Almanac

Your choice: anything on your list v. my questions

Tactical feedback

• What are you working on?
• How do you think things are going?
• What’s been your biggest challenge?
• What’s your biggest victory?

Team feedback

• How’s your boss doing? Any feedback for them?
• How am I doing? Do you have any feedback for me?
• Is there anything I can unblock you on?

Developmental feedback

• What are you trying to work on professionally?
• Do you feel aligned on what’s important with [manager/company]?
• Do you feel engaged in your work?
• Do you feel like you’re producing results?

Company feedback

• Are you having fun?
• Anything you’re anxious about?
• Anything you’re curious about?
• Anything you wish was different?
• Anything you’re really happy about?