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Roseanne's Operating Manual

Everything you need to know about working with me!

Roseanne Wincek

A little context for what an “operating manual” is:

The Operating Manual is a tool we use at

Renegade⁠

to help us work better with one another. We learned this exercise from our amazing coach,

Khalid Halim⁠

When Renata and I were first exploring starting our firm together, we did this exercise to dive deeper into what drives us, triggers us, and how we deal with conflict. As we’ve built our team, new members complete their manuals, and we’ve shared them at offsites.

It’s an invaluable resource and allows us to steepen the learning curve of getting to know each other and melding as a team. Specifically, we use the doc to describe some of our quirks, good and bad and to highlight preferences in work-style, feedback, and conflict resolution. Most critically, this work gives permission to each of us to have the sometimes sensitive conversations around work-style conflict and maximizing our individual and shared potential.

About Me

I’m

Roseanne Wincek⁠

, Co-Founder of Renegade Partners with

Renata Quintini⁠

. I believe deeply in the power of technology to create communities and collaboration. I’ve invested in

Compass⁠

MasterClass⁠

Glossier⁠

Looker⁠

, and

Motive⁠

at my prior firm. I’m on the board of

MasterClass⁠

Auxilius⁠

Daily⁠

LaHaus⁠

, and

Spekit⁠

. I was once a chemist and am from Cleveland, Ohio. I live with my husband, David, and our dog, Wallace. I’m one of 6 kids.

⁠

My Operating Manual

1. In your life/work, what do you look like on your best day? How do you show up?

On my best day, I have a lot of energy. I’ve had a good night’s sleep, and I’ve been outside and worked out.

I am a massive extrovert who gets energy from others, so COVID was particularly challenging on that front. When my energy gets low, I go for a short walk outside or bug David.

I love when I get that feeling that my brain is buzzing on all cylinders. My dream day is a mix of helping people be more creative and productive, and, in turn, finding that productivity and creativity for myself.

I am always game to brainstorm a new idea and love unstructured time to discuss those important/non-urgent projects. My favorite way to think through something is to talk it out. I love being active and do some of my best thinking and conversations when walking, hiking, running, etc. I love people who want to debate many sides of a topic to get closer to the right answer.

I’ve also grappled with ADHD my entire life and, when I really need to focus, I need time alone to get things done.

2. How would you describe your personality or working style?

(Do you like to work independently? Thrive in social settings? Prefer mornings or evenings)

My ideal working environment was the library in college. It’s the perfect balance of social pressure to be quiet and productive, while having people to bounce ideas off of or take breaks with. I’ve (sadly!) never found the same balance in an open office. However, I could happily spend the entire day working in a (ventilated) phone booth. My coach introduced me to the concept of

body doubling⁠

- basically a study buddy. I’ll often use

FocusMate⁠

to help me get in the groove (I’m actually using it right now).

I can either be a morning person or a night owl, but not both at the same time :). I’m a huge proponent of getting all of the sleep. I take shutting off or sleeping in very seriously - for myself and for others.

I do like using early mornings or late nights, those times when the outside world is quieter, for focusing and getting things done. The middle of the day, when there are lots of emails, slacks, and opportunities for interruption (I am often the interrupter...), isn’t my best focus time.

When I am chugging off hours, I don’t expect others to be, too. I fully expect that my texts/emails/slacks won’t be responded to until normal business hours. This is one of my ADHD strategies - when I am in deep focus, I have to complete each task. If I leave things hanging for later, they sit in my brain and take up cycles.

3. When things start to feel stressful, I look like this:

(Describe your reactions. Do you go silent? Get more involved/dive-in? etc.)

I get stressed when I feel rushed, overstimulated, or overwhelmed. When I want to be in deep focus mode, I get annoyed by anyone preventing me from getting there (and, often, that person is me). I love when other people are around, but if I need to get something done, I need quiet. I’m very social and like to talk, but I often do it as a way to procrastinate.

ADHD is not only struggling to focus, but sometimes getting out of focus. I can have a hard time jumping into a conversation because my brain will still be thinking about what I’ve been doing or want to finish. I may be short, get frustrated, or bluntly ask if we can table the topic for later.

Stress shows up as impatience for me. I get very impatient with whatever is standing in the way between me and what I want to accomplish. My co-founder, Renata Quintini, lovingly refers to me as a bulldozer. 🚜 🚚

One way that I deal with this is my strict policy on notifications. Attention is a valuable and scarce resource and the bar is high for what gets mine. I have no notifications whatsoever on my laptop. I don’t have slack or email notifications on my phone. That means I have to remind myself to periodically check things and to tell those close to me that if they need me now, it’s got to be by text.

4. When things start to feel stressful, I need this:

(What might you need that you couldn’t possibly ask for in the moment? A short break to clear your head? Someone to ask you “How can I help?” A change of focus? etc.)

Space and quiet to get things done. I do like help, but I am terrible at asking for it. I am a first-born through and through, and my independence can be my own worst enemy.

The best way to help me is to offer to take specific things off of my plate. I definitely overextend myself sometimes. Please don’t chide me for that. 🤗

I often don’t ask for help because I don’t want to be a burden. It’s not that I don’t want help or don’t trust others’ work, I just don’t want to overwhelm anyone!

This is one area where this document has been extremely useful! In a meeting, my partner, Susan Alban, announced that she was taking point on a portion of a complex project I was managing. Later, when thanking her for doing an amazing job and for her much needed help, her response was “Duh, I read your operating manual”.

5. How can people earn extra points with you/build trust?

Ask me for help! It’s terrible that I’m so bad at asking for help and loved being asked! 🤦‍♀️ I love being in service to others, and I love when those I work with are wildly successful.

To me, helping others makes me feel like they value me, my opinion, and my expertise. 🥰

6. How do people lose points with you/break trust? What drives you nuts?

I really hate being excluded or being shut out of conversations.

It drives me nuts when others are unwilling to change their mind or say “I don’t know”. I see being open to influence and flexibility of mind as major assets, not indecision.

I am very protective of people on my team, and I get more angry if someone is rude to them than if they are rude to me.

I particularly hate when people are rude to more junior or lower status team members. I was an associate once, and I’ve been treated poorly when people thought that I was an admin. (The fact that anyone would treat an admin without respect makes my blood boil 🤯.) One of my biggest trust building moments was when a senior partner went out of his way to stick up for me when an entrepreneur was rude because I was a junior woman. I felt so proud to be on his team.

7. What qualities do you particularly value in people who work with you?

I am incredibly lucky - I have many colleagues that have become close friends. I love working with people who are smart, whom I admire, who work hard, and who make me think in new ways. People who are kind, keep me honest, and make me better. There are few things I love more than deep talks with creative thinkers.

Boundaries are important, but I am lucky to work with people who show up as their authentically whole selves and with whom I can be my authentically whole self. I am a big believer that we work when we work and we rest when we rest. If we are working on time off, it’s not actually time off, and our work suffers from it.

We all operate at a high level and expect that of one another. Sometimes work gets in the way of life and life gets in the way of work. This is a marathon, not a sprint, and I value that we can be honest with each other when we need more time, space, or support.

I love structure, but I am terrible at creating it for myself. I love working with people to create systems and efficient. I’m not great at starting projects like this, but I am an excellent improver. I sometimes have a hard time getting started, so kicking something off and collaborating together makes me very happy.

8. What is the best way to communicate with you?

I love being together in person. That is my most preferred meeting venue.

Text is the best way to get to me if you need a fast response. After that, Slack → Zoom → Phone → finally, email. If there’s something important that you need from me that isn’t urgent, having Jessica looped in is a great way to make sure that it gets on to my Todo’s and has time budgeted for it.

I like to have time to socialize/chat at the front end of meetings. A few minutes of connecting can really make the time together more effective.

When we have something meaty to discuss, I love getting a document to read and digest ahead of time. Asynchronous comments are my love language, especially if our resulting discussion is going to be over zoom. I know that this is sacrilege to some people, but I do not like Looms. I learn better through reading, so I’d rather read the document myself than have it read to me.

I love being a part of a team that has really gelled and is humming. This is super important to us at Renegade, and we even have a structured method to

check in on how we’re working together⁠

9. How do you like to give feedback?

I can be overly direct in feedback sometimes, and I will occasionally just blurt it out. If and when I am too blunt, please tell me.

Honestly, though, feedback comes from a place of love. The amount of feedback I give is correlated with how much I care about the person and their success. I try to be as specific as possible about the action or behavior. I’m part of a regular T Group and always try to not ascribe intention.

I love calling out positives and good work. When I was in graduate school, it was really tough. Science is hard, and often, nothing would work. To get through the particularly bleak times, I became a big fan of celebrating the little victories. I like this strategy, even when times aren’t bleak. 😉

10. How do you like to get feedback?

I am always striving to improve - especially improve how I can be most effective with a team mater. Feedback is a gift. 🎁 Please, help me be better.

Feedback is most effective for me if it’s specific about the action or behavior - try to use specific examples. Come to me early - It’s way more troubling to hear that something has been bothering you for a long time.

11. What is the best way to convince you of something?

(Data, framework for thinking about the problem, social proof from others, etc.)

Logic and frameworks. When someone can walk me through their thinking and logic, it’s much easier to find the points of agreement and dispersion.

I love learning! Teach me how something works.

12. Outside of work, what is most important to you?

David & Wallace. My (very large) family and friends (who are like family).

13. What is most misunderstood about you, if anything, that you would like to clarify?

I tend to show up pretty confident and together, but I’m often seeking validation and support. I know I’m not alone when I say that I have total impostor syndrome. I often think I’m not working hard enough, letting someone down, or not pulling my weight.

ADHD can be a tough thing to manage, but I’ve developed my tricks over the years. ADHD is not all bad - it’s a big source of energy and creativity for me. If you recognize or are frustrated that I’m too scattered or distracted, bring it up. Naming it is the first step in managing it.

14. What else should people know about you or how you work?

Throughout my career, I’ve had to jump through some high hoops and have worked in cultures that believed that sanguine competition produces the best results. I do not ascribe to that philosophy. I do not thrive in that environment, but I can fall back into those old habits. If you ever see that behavior in me or that chip on my shoulder, please point it out.

I love puzzles, games, and doing cerebral things that aren’t work with colleagues. Sometimes I have a hard time turning off and separating work life from personal life, but I don’t expect that of others.

⁠