What is this?

I’m Jess Dale and this is my Manager README, a document that helps introduce you to my management style, philosophy, and expectations. The intended audience is primarily anyone who reports in to me, though anyone is free to read it - as well as provide feedback on it! Please treat it as a reference and promise on how I will conduct myself as a manager, and what I expect from you.

I urge you to hold me accountable to my promises, and to call out anything that might be missing from this document. Without your guidance, I will not be able to improve as a manager.

Disclaimer: This document does not apply to anyone else in the company, and solely reflects on my personal management style.

My Job

As a Design Manager, it is my job to:

  1. Start with why - providing context and vision
  2. Manage and develop well-functioning design teams
  3. Create safe spaces and provide support for designers to develop and growth
  4. Refine or define processes that ensure the success of our team’s work
  5. Hire, train and retain world-class talent

I’m here to help and support you, to set context for what you’re working on, and to advocate for you and the team with the rest of the company.

If I fail at any of these - especially anything that puts retaining you at risk - you would be doing me a huge favor by letting me know as soon as possible. I don’t expect everyone to stick around forever, however if a departure is potentially due to something we could have done different, I would appreciate the chance to make things right first.

How I approach my job

I am not an authoritarian boss. I do not want to micro manage anyone - it’s not a good use of my time, or yours.

My teams come first, the clients second, and the company comes third. Obviously I have a responsibility to the company, but without a well operating, well staffed, and well functioning team, I am unable to live up to those responsibilities. Your success is ultimately my success - so I will go out of my way to try and make you successful.

I may not always seem to be available, most often due to meetings. Regardless of how busy I am, nothing is more important than the time I can spend with you. If you need to chat - find time on my calendar - no need to ask. If you can’t find time, I will make time.

I believe in leading by helping others see more clearly what they already know, and finding the solutions and strengths that are already inside people. I love to be surrounded by people who challenge me and I recognize that everyone is my superior at something. I value open, authentic relationships. I promise to be kind, honest and empathetic with others, and hold a safe space for the hard, messy wonderful process of growing and flourishing as a full human being.

I’m big on work/life balance. Most folks work between about 10am (at the earliest) to 6pm (at the latest), and unless there’s an emergency, I don’t expect to communicate with you outside of these hours with respect to your local time. I try not to respond to e-mails or slack during off-hours and under no circumstances expect you to, unless it’s an emergency.

I want to encouraging and model a healthy work-life balance and avoid burnout. I may from time to time ask for help, too! My early warning sign is losing my sense of humour.

How I expect you to approach your job

I expect you to operate as a Directly Responsible Individual.

I am not here to tell you how to do your job. I believe you are able to operate as a professional adult, and make smart decisions. This does not mean that I expect you to do everything on your own - I am here to provide you guidance and mentorship (either through me, or by finding the people you should be getting it from). Nor do I expect you to know everything - when you need help, I expect you to not hesitate and ask for it. If you feel you made a mistake, own up to it, we’re all human and mistakes happen. Ultimately, I am here to help you do your job in any way I can.


I believe that there is a place for process on a team. I need certain processes in place to be able to manage up and out to the rest of the organization; however I do not believe in process for the sake of process. I know that what works for one team, will not work for another - and I know that dictating process is not ideal. I will attempt to improve process, but I want to make sure that any changes I make are beneficial for all parties. If you ever have feedback on process - please let me know - I want the team to operate at its best at all times, and having a process that makes sense for everyone is critical.

I strongly believe in putting people over process and changing process to accommodate our needs and goals. I’ve worked on the product side, the agency side, and the consultant side. At the end of the day, these are my values as a manager:


I’m a big fan of 1-on-1’s. I believe that these meetings are for you to set the agenda: What would you like to talk about? What’s going well? What’s bugging you? These don’t need to be about work updates unless you really want to talk about work. If there are things that I want to ask you, I’ll do it, but this is your time. If I have feedback, I will also provide it during this time.

For local chats, I really enjoy walking 1:1s; for remote chats, I have a difficult time focusing unless I can see your face over video. This is only a minimum though, and not a maximum! I prefer to have separate meetings scheduled for agenda-driven chats (e.g. goals, reviewing 360 feedback, etc.) so that we still have room for more timely 1:1 chat.

While I have a preference to meeting for 30 minutes every week, the length, frequency, and medium are up to you. To start, I will book us time to meet for 1 hour once a week. As mentioned before, this is not the only time you can reach me - if there is ever something on your mind, please reach out. If I am busy, I will find time for you.

If you don’t like the cadance of our 1-on-1’s, please let me know, and I am happy to adjust. The same goes for timing that works best for you - anything I can do to prevent unnecessary context switching. As mentioned before, 1-on-1’s are your time with me - and if you want to skip a 1-on-1, or cut one short, that is completely fine.


I am a strong believer of Radical Candor; I want to ensure that you are receiving honest and actionable feedback on a consistent basis. There should never be a scenario where a performance review, or in the worst case scenario, a Performance Improvement Plan, is the first time that you hear negative comments or feedback. I will provide you with feedback and guidance to the best of my ability, and will do my best to ensure that you understand the feedback that I provide to you. I will always ensure that feedback is given in a private setting.

Feedback should go both ways. I am relying on you to let me know when I am doing something detrimental to my position, our relationship, or the company. If at any point you feel you have feedback to provide to me, I will listen and internalize the feedback you give me. Beyond that, I will go one step further and ask you three questions at the end of every 1-on-1 we have:

I know that this gets repetitive - but it’s very important to me to ask those questions every session.

I will also send an anonymous feedback form on occassion to allow anyone to provide feedback they do not feel comfortable telling me in person.


Part of my job is to track the performance of those who report to me - and obviously provide you with feedback on how to improve.

Please reach out and tell me if anything, at all, feels off. It’s so much harder to solve problems when we’re guessing what they are. I’ll never consider proactively speaking up about challenges as a sign of complaining. I really value hearing your honest, transparent thoughts about how we can learn and grow together. Bonus points - Thinking about solutions/approaches to the challenges you bring up (I totally understand this isn’t always possible, and sometimes even what the challenge is is unclear).

Please invest in 1:1s - if you’re a manager, please do regular (weekly) 1:1s, and if you’re an designer, please use the time of the 1:1 as a chance to reflect on your challenges and growth.

Please set healthy goals and boundaries for yourself, and if you’re a manager, model healthy work-life balance to your team.

Please invest in yourself and focus on self-improvement. This looks different for everyone and can be going deeper, going broader, or engaging in feedback to really listen. If you’re a manager, please build a peer network for yourself and keep learning and educating yourself about leadership.

In general, please over-communicate with me. Don’t worry about sending me too many messages or overwhelming me, it’s really valuable, and in our remote context, I’d love to be here for you for what comes up because I can’t see how you’re doing by walking around an office.

Things you should know about me

I have personality quirks. We all do. Here are some things that I am both aware of, and that may impact how you work with me:

Here are some of my personal values that inform my work.

Download my resume