Here's a primer on how to work with me effectively. Reading this will help you ramp up on my work style faster. I'd also very much like to read your "ReadMe" if we work together, so share it with me if you've got one.

How I like to work:

  • One of my biggest pet peeves is information asymmetry, especially when I or someone has a piece of information that someone else needs to be unblocked in their work. Therefore, I over-index on transparency, and I want all our company data to be as available as possible to everyone in our company.
  • This also means I like to make decisions fast, most of the time, using a Type I and Type II decision-making framework. I'll almost always choose to make a decision now vs. waiting until later. I sometimes think a decision is Type II when it's actually Type I. I appreciate it when you push back on me if you feel I'm getting that wrong, and I'll probably have a spirited debate with you about which it is.
  • I work on a project output basis, mentally, which often doesn't fit into neat one-hour blocks on a calendar. This means by default I choose not to accept as many calendar invites as possible, so I have the time flexibility to achieve a meaningful level of output on the things I do focus on. This can be frustrating to people trying to secure my time.
  • I believe if something's important enough to spend time on, then we should do it in a disciplined way that maximizes the time investment. This means I expect meetings to have an agenda, and I expect us to prioritize the agenda together to ensure we discuss the most important things first. When people commit to action items, I expect those commitments to be written down, and when we make decisions, I expect those to be written down as well, so we can refer back to them later as our source of agreed-upon truth.
  • I push hard, and it can become overwhelming because I'll keep pushing & probing on a topic if I see more opportunities to improve it (I often say that "no" is just a request for more information). One thing you can do here is push back -- I appreciate candid pushback, and most people aren't comfortable doing it. I respond well to reasoned thinking about why I'm not pushing in the right ways or right areas.

Things you may find challenging about me:

  • I really believe in focus, but I've been told that interactions with me can be de-focusing, because I may suggest an idea or push in an area that's outside of someone's current scope of work. I strongly believe that since we can't manufacture time, the more things we are doing, the less well we do each thing, and yet I also often have a number of ideas I want to try to better understand if there's value in them. A great, tactical way to deal with this is to ask me "which is more important?" between a set of initiatives, so we can discuss together what the best way is to spend our time (and hence apply our focus). I will always be supportive of you pushing back and saying no if you can give me a good reason for it.
  • I always joke that a startup CEO does everything just poorly enough to motivate others to do it better. I never get to spend as much time with anyone as I'd like, and I never get to go as deep as I'd like. This means that you may not feel like you can get enough of what you need from me. My preferred outcome here is that you ask for forgiveness instead of permission, and use your best judgement to execute vs. being constrained by my lack of attention or availability. But sometimes, you might just need to get my attention to be unblocked, and I want you to be direct with me and tell me "I'm blocked by you on this" so I can ensure I carve out the time to un-block you. It's one of the great pains of my role that I can't spend more time & focus in any one area of the business.

Things I care deeply about in our interactions:

  • Do what you say: I've learned to listen to people's actions over their words. If there's a conflict between what you say and what you do, I'll prioritize as truth what you did vs. what you said every time. I find incongruencies between the two challenging, and I'm apt to point them out to you. What works best for me is that you do what you say you're going to do. If you can't, then communicate with me to update my expectations. It's OK to reset expectations with me. It's not OK to fail to communicate that change in expectations once you've set them.
  • Put in the "last mile" of effort: I wrote an entire blog about this. I very much appreciate the mentality of "what's one more thing I can do to impact this outcome?" There's always one more thing.
  • Be more effective by being more efficient: Time is our most precious asset, and none of us know how much of it we have left. Be as efficient as you can, so you can be as effective as possible with your focus. Learn to be efficient with the technology you use every day. I love being taught ways of being more efficient with my time as well.
  • Tell me how you're feeling: Business runs on relationships, and relationships run on feelings. But especially in the workplace, people often aren't comfortable sharing their feelings. I do want to hear those from you. It's ok to tell me "I'm feeling frustrated by [xyz] that you're doing." Nobody can argue with your feelings, so please express them to me so I can understand you better – it'll also help me be more empathetic towards you, which I always want to do, but I'm not always great at doing.

My Operating Approach with Direct Reports:

  • I'll do a career session with you within the first 30 days of you starting. We'll define your career objectives for the current fiscal year, the upcoming fiscal year, and long-term, and we'll use this document to help you achieve them.
  • We'll do weekly 1:1s. If you can't make one, please make sure you reschedule it within the same week. This is an opportunity for you to share whatever’s on your mind. I’m there to listen, troubleshoot and provide guidance. If it works well for you, I recommend you stamp out the weekly OKR questions, and answer the ones that pertain to whatever’s on your mind before we sit down, which will help us cover more ground.
  • Sometimes I will have constructive feedback for you in our 1:1, although I always strive to provide direct, constructive feedback (as well as kudos!) as close to the moment I have it, vs. waiting for the 1:1. This means I sometimes create a "feedback stub" over a private Slack message, to remind us to discuss it in person.
  • Every Monday morning I have an Exec team meeting, where we share & review wins from the past week, Review OKRs w/ Business Intelligence Dashboard performance metrics by department and identify what the #1 blocker is to our growth, and deep dive on that topic. The first Monday of each month we do all this with the full management team.
  • I run a weekly tribal all-hands every Tuesday at lunch where we share wins from the past week, and each department owner provides an OKR update with a Business Intelligence Dashboard review.
  • We'll do quarterly Exec team offsites right after our board meetings. We set and prioritize an agenda before the offsite. Please come with as much data as possible to support your positions on the topics we’re discussing.
  • We'll do quarterly OKR planning, which is a combination of a tops-down and bottoms-up process.

My Interaction with Your Team:

  • Please put me to work to highlight and remove blockers you and your team have. Removing blockers to enable you and your team to execute as effectively as possible is a top ongoing priority of mine.
  • Share with me the members of your team that are over and under-achieving, with specific examples. I’ll help celebrate their wins across the company, and I’ll work with you to determine to to resolve any performance concerns.

Our Communication:

  • I don't mind being called/Slacked/texted anytime you need something time sensitive, even if it's after hours or late. I put my phone on mute when I'm sleeping or unavailable, so don't worry about disturbing me.
  • I much prefer Slack over email for internal communication.
  • Feel free to cc me on any external emails, but also Slack me whenever you specifically want me to respond (and in what way).
  • I’m very allergic to PowerPoint/slides. I’d much prefer that you make a collaborative agenda in Hackpad that we can prioritize together, and use the specific format of:
  • Open Action Items(this is where we’ll put any that come from the meeting)
  • Decisions to be made(this is also where we’ll document the decisions we make in the meeting)
  • Agenda (in a prioritized, descending ordered list)
  • Raw Notes(this is where we’ll write raw notes from our discussion in the meeting)
  • Include links to as much supporting data as you can in the agenda or raw notes (such as direct links to our Business Intelligence dashboards) so we can have an efficient, detailed conversation with high output around the topic and decision(s) to be made.

Ways I'd like to learn from you:

  • I'm deeply appreciative of people who are experts in their craft and excited to share their expertise. I always want to pick a little bit up with every interaction. Teach me something new as often as you can.
  • I'd also like to learn how you work most effectively, so we can be effective together. Share your "ReadMe" with me if you've got one, and consider publishing one for everyone who works with you if you don't.