Working with Claire: an unauthorized guide
First of all, I’m really excited to be working with each of you and your
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,
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
Quarterly planning sessions—it’s my hope we make these happen with strong
pre-work and good follow-up afterward with our teams and partners (internal
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
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.
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
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
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
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.
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.
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
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
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.
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
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
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
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.)
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 to a better outcome.
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.
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.
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
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
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.
If we don’t have a 1:1 for a while, feel free to email or ping, of course.
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!
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.
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 response or urgent reading and I’ll do the same for you.
FYI = no response required.
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.
If it’s urgent/impt/timely or super short feel free to ping any time, even
when I am “red.”
Short questions on ping are fine but I might be inconsistent in response
times since I am often in meetings.
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 a quick in-person sync 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 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 to have fun with the people I work with.
Hope this was helpful and, again, I look forward to working together.
You are all welcome to add to this document and make it a little more