<aside> 💡 Welcome to My User Guide.  The goal of this document is to build trust through Intimacy (into me you see) and to create a thriving working relationship and culture by being clear about my commitments, expectations and how I work best with teammates.  Specifically, I recognize that the faster/better we get to know each other, the more trust we will build, the more we will accomplish together while having a lot fun.  The more trust we have will also enable a safer space for both of us to grow.  I encourage you to write a User Guide as well for me and your teams.  This will be a living document that will evolve as I do!

In general, this document is written more towards “my reports” with me as CEO vs my partners/co-founders, but I think 80% of it still applies and will be helpful to review and understand so you know me well.

</aside>

My Why

My Why is to help others be the best versions of themselves.  I want to empower others to learn & grow (at a rapid, uncomfortable pace) and use entrepreneurship as the canvas to do this.

In my experience, entrepreneurship and business is incredibly challenging and super rewarding.  Like any great undertaking (e.g., running a marathon), the journey leaves people having experienced tremendous personal growth.  Delivering this for people is my why.

I also want to live this Why through the products and services we build.  I want our products and services to clearly solve a problem for people, improve their lives and enable them to be their best.

My Zones of Genius

Zones of Genius are a unique combination of 1) natural strengths, 2) love doing, don’t feel like work and give me energy.  Here are mine:

• Entrepreneurial creativity - I love sitting in a room/whiteboard and dreaming up something that doesn’t exist today.  That happens for entire business ideas as well as small processes that will help us be better.  I read a lot.  I meet a lot of people.  I am good at connecting dots.  And so I love to do that in ways that will generate new/creative ideas.
• Entrepreneurial problem solving - related to above, I am in my element when there is a tough challenge in front of us and we are looking for an “impossible” solution.  I am naturally resourceful and a non-linear thinker.  I can quickly brainstorm many solutions (most of which are bad).  I am often willing or able to do stuff most people can’t (e.g., cold email Mark Cuban, I tracked down a professor for a special baby sleep guide, have a difficult conversation, ask for a favor)
• Coaching/Teaching Others - I LOVE teaching.  My mom is a teacher.  I enjoy the process of learning myself and then sharing knowledge, iterating with someone to help them get better.  I love watching A HAs happen.  My favorite moments are when someone emails me after a few years telling me how much they learned while working with me.
• Force multiplying/GSD/Triaging/Prioritizing - I have a gift for looking at a situation, knowing what it takes to get it done and figuring out the most important few things needed to get it accomplished successfully.  I learn super fast, I will take risks, I will turn things on and off quickly to find a way to make something work.
• Persuasive/Inspiring Communication - I did lots of public speaking as a teenager and love storytelling.  I love doing this when recruiting, selling to clients, finding partners/vendors or talking to anyone in my orbit. I have over 170k X/Twitter followers and know how to write engaging content and build audiences.
• Relationships & Partnerships - I love connecting with people quickly and deeply.  I will share personal things quickly and try to help and add value to those I meet.  I remember people and proactively reach out with opportunities.  This has cultivated a powerful network of friends/associates who I lean on for advice, introductions and other opportunities. I actively enjoy building this.

In general, I request you help me to stay in my ZoG.  When I’m there, I’m at my most powerful and having the most fun which usually leads to great business results for everyone involved.

My Development Areas

• Spreading myself thin - I get excited easily in big and small ways.  This could be anything from taking a new meeting to spinning up a whole new business.  It shows up in my calendar, being pretty jam-packed + needing help context switching. I am aware of it and am practicing saying ‘no’ more often.
• Context switching - Since I do a lot of context switching, when starting a meeting with me, some historical context or a report I’ve seen before really helps me to get in gear around whatever we are discussing.
• Harsh/“below the line” communication - at times, when I am frustrated, I can be short or sometimes harsh in the way I say things.  This isn’t my ideal and I’m working to stay “above the line.”  It’s usually worth unpacking after the fact to clear out any negative impact and figure out where we may not be aligned.
• Expressing appreciation - I grew up in a house where “no feedback” = good.  I have realized this doesn’t serve me and isn’t the type of culture/company I want to foster.  So I am actively working on expressing more appreciation and providing as much positive as constructive feedback.
• Empathy - Similar to appreciation, I am actively working on putting myself more often in others’ shoes.  That can be employees, partners, customers, etc.  It isn’t a natural muscle I’ve built so I am actively working on it.  Feel free to call me out on this or remind me to do it!
• Time management - due to some of the above, I’m a work in progress around time management.  I’ve improved a lot but I can run a few minutes behind, need to make last-minute changes and sometimes totally miss something.  Feel free to confirm times with me and call me out for being late to help me improve.

My business beliefs/values

• High bar/excellence/high-performing culture
• Challenge convention/having it all
• Entrepreneurial Rigor, imagine a 2x2 chart and aim for “high” on both Hustle and Rigor
• Hustle
  • Speed - move with Urgency, always.  When someone says 1 week, you ask “How about 1 day?”
  • Creativity - Use imagination, brainstorming, “what if?” “I wonder” type approaches
  • Boldness - Take risks, have courage in big and small ways, always ask
  • Resourceful - Find clever/unique ways to overcome difficulties
  • Tenacity - Resilience + dogged determination, esp when there are setbacks
• Rigor
  • Quantitative - use the appropriate numbers, data for decisions
  • Logical - First principles sound reasoning, structured problem solving
  • Prioritized Focus - Chooses few things, stays on them, does not get distracted
  • Thoughtful - Reflective, briefly stops to digest learnings/iterate to keeping making progress
  • Creative intuition drives testing.  Data drives decision making. (This is a natural part of entrepreneurial rigor)
• Prioritization
• Empathy/Human relationships
• Fun/Goofy/Silly
• Candor/Vulnerability/Truth
• Dream Big, Act Small
• 1% better every day
• Ownership
• Service obsessed
• Principles of Conscious Leadership
  • 15 Commitments

**Expect me to always press on these areas.  For example, you will often hear me press on ways things can be done faster.  Try to actively and openly participate in the creative process here vs resist it/worry I’m being unrealistic.

And push back using logic/data etc.  I’m able to compute constraints but also bring some creativity to bear.  This process usually yields more creative solutions that do speed things up even if it isn’t possible for something to take a day vs a week.**

Communication

• I love communicating!  I’m a pretty strong extrovert and get lots of energy from talking/collaborating.  I totally understand if you don’t and can manage around it if you share this with me.
• I think 90% of issues root from poor/unclear communications so if we get great at this, we’ll be great at the rest.
• Over-communicate - I have NEVER once in my career told someone they are communicating too much.  Err on the side of 2-3x the communication you think is reasonable.  I have a unique ability to process a lot of information quickly and effectively.  Over-communicating helps us build trust because it lets me learn how you think, how you lead your team, have a view into the pace of inputs, results and resourcing of your business/team.
• Hierarchy of comms - Most Urgent to Least Urgent = Phone, Text, Slack, Email.  If we are going back and forth on any written comms for more than 5 mins, call me or I will call you.  This resolves most items quicker.
  • Slack - quick sync/internal comms (<5 mins) or where we want others to easily follow. Also internal scheduling requests.
  • Text - fast/urgent and super short
  • Call - urgent and/or to discuss something >5 mins
  • Zoom - more organized presentation for review etc
  • Email - async review and/or external
• I usually pick up calls, I text often but can lose texts, I like slack for real time comms and email is better for asynchronous/deep reading (anything that will take me longer than 5 minutes)
• I typically will call you for 2 different very polar opposite reasons: 1) there’s something urgent/tactical to get done (more often during the work day) or 2) I have a small window of time and want to “chat” - check on you, hear the latest, etc
• Use FYI (for your information) or NNTR (no need to respond) to signal to me the comms doesn’t require a response.  I will do the same.
  • AND if those two are not present, I do expect some type of (rapid) response (the most simple is ACK which stands for acknowledged) so I know you read it and it’s moving forward.  (Always assume I do not know what is in your head unless you tell me).
• Comms expectations - I generally expect same day responses (its totally ok to say, I saw this am deprioritizing and will respond by X date).  I get my inbox to zero on most days so will also see/know when others aren’t being responded to.  I like to text, email, slack random ideas/learnings, sometimes at odd hours.  Unless I say URGENT, do not feel any obligation to respond until the next day.  If you absolutely hate this, let me know and I’ll do my best to curb it or batch it somehow.
• Accountability in comms - I don’t expect you to respond to everything in real time but I do expect you to close the loop on everything we open.  If it’s  on my plate, I will do the same.  This is critical for ownership and credibility.  Please find ways to get things off my plate, into your biz/team/system that you create transparency around (who is doing what by when).  I get frustrated when I have to follow up on something or ask about it twice.
• When you communicate/report, lead with (at minimum) a point of view.  Ideally, with a recommended course of action/solution.  I am always interested in the reason you believe what you believe/to see how you think.  Share your rationale in a few bullets which include data, numbers, logic, examples.  I believe communication is a reflection on how you think.

Reporting & Data

• Create a regular, systematic, clearly framed written process by which you share your progress against plan.  Collaborate with me on this.  Make it as data-driven and quantitative as possible.
• Share this update no less frequently than weekly (but daily works if appropriate)
• Be clear with yourself and me about what is ahead of plan, meeting plan and behind plan.  Use this to prioritize.
• I place a high premium on data, numbers and measurement to describe your results.
• Report on results but also measure, report and improve INPUTS driving those results (e.g., number of new creative tested is as important as CPA, number of outreach emails is as important as new hires made)
• Try to measure, set targets and report on EVERYTHING.  It’s not always possible but you’d be surprised at how much you can measure/quantify and how valuable it is to do this religiously.  Start to measure things even before you have a target/desire to change it, those “stakes in the ground” will be very valuable.
• Expect that sometimes I will pressure test and dig VERY deep into numbers, inputs, etc and other times I will not comment at all.  This is (mostly) on purpose.
• Relate to your plan/reporting as an amazing opportunity for us to reflect, learn and adjust NOT as a report card or personal reflection on your value as a person :)
• I’m very casual most of the time but that doesn’t extend to rigor or expectations around communication and numbers.

Example Daily Reporting Rigor

Meetings & 1x1s

• Meetings can become expensive, unpleasant and wasteful if not carefully managed and intentionally set.  I will generally try to avoid meetings where possible and/or shorten them.

• I like the default for meetings should be no meeting.  Can it be done with an email, loom or some other 5 minute way?  This requires a clear ‘by when’ agreement

• 15 minute meetings are great! I like shorter meetings, where we have the right data/context and can make a quick decision.

• 1x1 - Lets keep a slack/doc to capture ongoing items for discussion.  I like agendas for any meetings (including 1x1s) and a focus on getting through the agenda and accomplishing the goals of our meeting.  If I veer off, pull me back on (we can table something).  1x1s can generally focus on mutual feedback, talk about how work is going, broader discussions, check on how you’re doing, etc.  I prefer to keep more functional reporting to those respective meetings.

  

• I generally try to avoid standing meetings.  I think it's important we look at the business and dynamically (weekly) adjust our meetings to what we see happening and where our focus is.  That means some weeks we could meet several times and some weeks we could not meet at all.

• When booking a meeting with me, please focus on your priority and needs and DO NOT worry about my calendar.  I am constantly moving things based on priority so if you have something that needs attention today, more often than not I will prioritize it vs maybe a networking call I have.  Ping me AND my assistant (going from most/least urgent method of communication described above) to book time. (e.g., if you need to talk today, call me, tomorrow, text, later this week slack, a week out, email.). Please DO NOT slow the business down (e.g., delay a decision) due to my availability (without an explicit convo.).  I will get frustrated if this happens.

• Escalation - like communication, I’ve never had someone who “escalates” too much.  If you are blocked, need a resource, are struggling with a client or partner, just flag it for me.  I can often help move things quickly if I’m aware.

• I think a communication infrastructure is critical for business success.  I think this starts with some future goal/vision (Desired Future State), assessing the current reality and then choosing a handful of things to work on to make the vision come true.  Having the artifacts of this outlined using either OKRs, GIST or the “DFS/CR/Waypoints” framework along with a clear financial projection is a baseline for running the business.  From there, I’d like to have 1) annual 2 days offsite with a plan locked before winter holidays, 2) quarterly half-1 day offsites to assess/roll our plan, 3) monthly financial reviews, 4) weekly meetings run with the “waypoints” (or Objectives) prioritized.

• Meeting Agenda/Prep - I ask everyone strive to share an agenda the day before for any given mtg and include any pre-read materials or something else you want me to be prepare to discuss. Examples of agenda questions/items to share:

  • Topics of discussion?
  • What is success in this mtg/convo?
  • What would make the mtg a 10/10?
  • What decisions are being made and who is making them? ‣

Collaboration

• I enjoy the process of collaborating (strong E) especially in person or over phone/zoom with the right setup.  Structuring this so it's clear the problem we’re solving and it has a clear deliverable helps guide me and be productive.
• Converging/Diverging - Give me a heads up on where a decision/initiative stands in the beginning of a conversation so I can calibrate appropriately.  “Converging” means you are 80%+ sure, you just want some validation/gut check and maybe ideas for how to get it across the finish line.  Diverging means its early, you’re looking to brainstorm and come up with some new ideas.  Without clarity here, I may diverge when you want to converge and vice versa which will be unproductive/frustrating for both of us.
• Always share your point of view/lead with a recommendation/game plan (backed by data/logic etc).  It not only forces you to think, but allows us both to see how aligned/similarly we are approaching a problem.  There’s a ton of learning and gelling in this process.  If I don’t hear/see a recommendation/POV, I will assume you don’t have one and “fill in the space” with my POV which I’ll generally expect we go forward with.  My goal is to be more of an “editor” than a “writer”
• I will engage on whatever level detail you present and ask me to fly on - I can and will go deep when either 1) that’s the issue you present or 2) it seems like a higher level issue needs a deeper dive to get to the root cause.  I prefer to stay higher level or at least frame something through that lens than dive deep.
• Clear agreements - I enjoy the dynamism of collaborating around the highest level strategy down to the most minute detail.  This can feel overwhelming for some and it's important we have a system that allows us to know what is something we will DO vs just an idea we discussed in passing.  I like to use a system or “requests and promises” aka Clear agreements.  Let's get in the habit of discussing 1) who, 2) will do what, 3) by when.  Let’s write these down in our channel and use as a simple accountability system.  I encourage you to do the same with your teams.
• I like to involve more junior team members as much as possible so they can see and participate in the conversations/collaborations as a “learning by doing” type collaboration.  Bring people along as much as possible.
• Injecting vs Ejecting - my ideal situation is the business can operate and exceed its plan WITHOUT me being meaningfully involved.  With that baseline, you help me “inject” where there is crossover between 1) My Zones of Genius and 2) Large Impact on the Biz.  I will also likely inject in some way when the business is not meeting its plan, the best way to help me here is come with a clear POV on where we will go and where I can plug in to help.  Ejecting is also important to me: what that means is when I’m no longer needed and/or you can absorb something I stood up, you take it off my plate.  It also means we have the relevant comms/reporting so I can disappear for a week or so if needed and no piece of the biz is meaningfully depending on me.
• Backlogs/Roadmaps - I believe lots of ideas AND prioritization are important for innovation.  To that end, I expect you will have some system for constantly capturing ideas (of which I have many) and then regularly prioritizing them based on some framework (I like ICE, Impact, Confident, Ease) and executing them.  What I recommend is having a slack channel where people can consistently share ideas, have a junior team member put them all in a google doc and you review them 2x per month.  Then monthly, you prioritize that backlog and we review it together.  I recommend encouraging something similar for each team/function (creative, marketing, product).

My Leadership/Management Style

1. Hands off vs Hands on
2. Results
3. Changing my mind