Working with Gary

December 10, 2021

I often include links in these posts, which add detail to whatever point I’m making from other people. But this time, I have to go all Fanboy on how much I love Claire Hughes Johnson, COO of Stripe since 2014.

I’ve read Claire’s observations for a while on Twitter and various online media, but she prepared a doc for her new direct reports. It reminds me of similar statements I’ve made over the years. I wish I’d codified them rather than sharing them in emails. Read on, and I’ll be adding my edits over time.


First of all, I’m really excited to be working with each of you and your teams.

Operating Approach

  1. Bi-weekly or weekly 1:1s. We’ll try to keep the times consistent so you can plan. I’m a big fan of a joint 1:1 doc to track our agendas, actions, goals, and updates. EDIT: I’LL KEEP THESE TIMES SACROSANCT! I’ve had my own 1:1s cancelled upstream with little or no warning. Once you start down that slippery slope
  2. Weekly team meetings, as appropriate—I view these as both update and decision-making/work review forums. I expect people to be prepared and to participate, even though we’ll have to manage video conferences and time zones.
  3. Quarterly planning sessions— I hope we make these happen with strong pre-work and good follow-up afterward with our teams and partners (internal or external). EDIT: these quarterly meetings will be good touchpoints for longer-term projects, and will provide roll-up data for our annual departmental strategic planning retreats.
  4. It’s possible that we’ll have some Stripe separate business review-type meetings and we can work hard to keep work manageable between these and planning sessions. Stay tuned.
    Speaking of 1:1s…
  5. We’ll do a career session at some point in our first few months of working together—your history, why you’ve made choices you have made, what your ambitions are for the future, etc. These help me know where you are in terms of personal development interests and ambitions with respect to longer-term plans.
  6. Personal goals—I believe in the two of us reviewing the top 3-5 personal goals you have each quarter or so (these are the things that you personally spend your time on, not your team plans, which I know you also spend time on). We can discuss them each Q and then mark out a plan on how we make sure you get the time, space, and support to accomplish what you need. I do these every 3–6 months and will share mine with everyone, also.
    Your teams
  7. Please add me to emails (fwd as FYI or add me) or documents that might be helpful for me to see as a way to understand the team and day-to-day work.
  8. As work is ongoing or a team member does a great job on something, forward it or link from our 1:1 doc. I like to see WIP and I am happy to meet with folks who have done great work so they can walk me through it—your discretion.
  9. Finally, I look forward to personally meeting everyone on your team and let’s keep an eye to make sure I’ve done that over the next few months.

Manager Handbook

Management Style


  1. I’m very collaborative, which means I like to discuss decisions and options and whiteboard big stuff in a group. I will rarely get stuck in one position or opinion but the downside is that you won’t always get a quick judgment out of me—I need to talk it through and see some ideas/data/options. Due to this bias, I can sometimes be slow to decide and if you need a decision quickly, make sure I know it.


  1. I’m not a micro-manager and I won’t sweat your details *unless* I think things are off track and if I do, I’ll tell you my concern and we can work together to make sure I understand and plan together on how to communicate better or right the situation. That said, when I am new to a project/ team I often get into the work alongside people so I can be a better leader—I will get involved in details and be more hands-on early on in a new initiative and just be warned on that. It’s how I will know how to help if you need me later.
  2. I expect you are making decisions a lot without me and if you come to me I’ll usually put it back on you with, “What do you want to do?” or “What should you do?” and just help you decide. That said, if there is a big one brewing, I’d love to know about it and I’m always here to talk it out. I like to know what’s going on with you and your team.

Accountable and organized

  1. I take action items really seriously and I expect you to know what yours are, when they are due, and get them done. I don’t like chasing them but I do notice when things slip—it’s fine to renegotiate deadlines but I’ll be annoyed if it’s the day after the deadline.
  2. I dislike being caught last-minute with people working hard on something we could have gotten ahead of—please help anticipate big work efforts and let’s be in front of them together. Similarly, I want us to be ruthless in priorities while we are resource-constrained. I need you all sane — and me too.


  1. I like data and dashboards so there is one, objective (ideally) way to measure progress and results but I dislike being bogged down in data and torturing the numbers. Let’s review consistent information on what really matters and use data to get insight, not to lull ourselves into thinking we know what’s going on or to try to find answers that might involve going with our gut.
  2. I also like to make agreements on “how we do things” that we then agree to vary/make exceptions on as a group versus everyone inventing their own process/frameworks.
  3. If we’re discussing something and you know of or can imagine data that would be useful to our decision, bring it up. (See below—sometimes I go into intuitive mode and I should be analyzing first.)

But intuitive?!

  1. I’m also intuitive about people, products, and decisions which means I’m happy to handle situations when I don’t have a lot of facts or data. You’re thinking uh-oh, she’s going to jump to conclusions, but I’ve worked hard in my career not to be that person. Ultimately, I think I have a good gut but I’m not wedded to it. *Your* job is to get my sense of something and argue it out with me. I love a good fight for a better outcome. EDIT: this part reminds me of what I’ve read about the cabinets of Lincoln and JFK…how they both at times let their secretaries verbally duke it out, and then he’d make a decision.
  2. I use my intuition a lot with talent management and I’ve been told I am a good “read” on people. Again, I work hard not to judge or jump to conclusions but I will put forward hypotheses about your team members and your job is to make sure I really know the people.
  3. I always like to know what’s going on personally with people so I can see the whole picture. I am a believer that we are “whole selves,” not work selves and home selves and it will help me know you and your team better if I know context. If something hard is going on with someone on your team, I’d love to know and be there to support you/them.


  1. I try to think about where things will end up and the straightest line to get there but I’m pretty flexible along the way. If there is swirl I usually think to myself: “What’s the big lever here?” “What problem are we trying to solve?” “Why do we need to solve it?” “When do we need to solve it?” “What information do we need and when will we get it?” and I expect you to do the same. Every day I try to think about what’s the most important thing I can do and do that above all else. But sometimes I get buried under email and fail.

By the way, I am often overly generous with my time and say yes too often to things. If you see this, please flag it to me. Although I love meeting with people, I sometimes don’t spend enough time on the strategic stuff because I am working on other things. Help keep me honest.


I put this last because I think of my key leverage as more about scale than individual customer work, but I’m always interested in sales status, customer issues, customer stories, and meetings with users, especially when I’m traveling.



  1. Use 1:1s for items better discussed verbally and items that can wait for our weekly check-in. Email takes a *ton* of time, so use it wisely.
  2. If we don’t have a 1:1 for a while, feel free to email or ping, of course.


  1. I read fast but I have slight carpal tunnel in my left arm and I don’t love writing super long emails, nor do I think they’re very productive, although watch me break this rule on occasion!
  2. I will read every email I get in a day but I don’t respond just so you know I read it—I’ll only respond if you ask me something directly or I have a question. Thus, assume I did read the email within 18 hours, but if you think I owe you a response please resend or ping me and I won’t be offended.
  3. I *love* FYI emails when you send me something you saw, a customer anecdote, an article, some data, or something someone on your team did and if you write FYI in the subject or in the fwd I’ll know it’s for my information but *not* requiring a response or urgent reading and I’ll do the same for you. FYI = no response required.
  4. If you add me to a team email celebrating something that I somehow missed, I know that’s the signal to weigh in usually with “yay!”, so go ahead but don’t overuse it or in my experience people will think it’s meaningless.


  1. If it’s urgent, important, timely, or super short feel free to ping me any time, even when I am “red” (unavailable).
  2. Short questions on ping are OK but I might be inconsistent in response times since I am often in meetings.
  3. If it’s a long topic and not time-sensitive, maybe just wait for our 1:1.

Overall, I like more communication rather than less and I like to know what’s going on with you and your team and that helps me do a better job for you. I don’t view that as micromanagement, but if you feel like I am too much in the weeds, please tell me.

Finally, I don’t believe I will create a lot of email volume and I’ll be the first to recommend we do quick in-person syncs to resolve something versus a long email exchange. Or better yet, you can be the first to recommend it, and I’ll be the second.

I also like plans that are documented. I don’t care if it’s slides or docs or spreadsheets, but I expect detailed work has been done when needed and if you have WIP or plans, I love to be included early and often in their development *but* I’ll generally only weigh in when asked or on the final review, even if I have draft access.


I like it. I like to give it and I like to receive it, particularly constructive. We’re in this to get better together. We’ll have a quarterly official session but I’ll try to be timely when I observe or hear something and please do the same. I also like to know how and what your team is thinking and feeling. Remember, whatever I hear or see, I have your back and I’ll tell you when I’m concerned. Anyone who vents to me about you is going to get my help to tell you directly.

Management and people 

I care a lot about you, your people, and all of your development. Please make sure we’re touching base on your team, building our teams’ skills as individuals and as teams constantly, and that I know when there are superstars and challenges so we can help people together.


Let’s get good ones and know we did. Measure measure measure 🙂


Finally, I like a good laugh and having fun with the people I work with.

Hope this was helpful and, again, I look forward to working together.

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