I strongly believe that deep self-awareness is essential for being effective at work. You can’t change your working habits if you don’t understand why you operate the way you do. Moreover, managing people and teams effectively as your company grows requires a solid understanding of yourself and the contributions you make to your work environment.

Are you lacking self-awareness? Here are a few telltale signs to check for:

• You feel drained at the end of a workday, yet you can’t pinpoint the reason.
• You’re consistently receiving feedback from various sources that you disagree with. This doesn’t automatically mean the feedback is correct, but it does indicate a disparity between how others perceive you and how you see yourself.
• You often feel frustrated and annoyed because you don’t agree with your team’s direction or decisions, and it seems like your colleagues don’t understand what you’re trying to convey when you explain why.
• You can’t describe the types of work you enjoy and those you don’t.
• You have friction with your manager, and you’re both struggling to resolve it

If you check one or more of these boxes, it’s time to dig deeper into the reasons why.

One of the most useful tools I’ve found for building self-awareness is the ‘Working with Me’ document (also known as the Manager’s Manual). This tool prompts you to ask yourself the right questions about your work habits, meeting preferences, communication style, and more. It’s also an invaluable resource to share with your direct reports during the first few months of working together, as it provides them with insights into how to collaborate effectively with you and what to expect.

To give you a better idea of how this tool can be used and its potential impact, I’m sharing my of my own ‘Working with Me’ document. It’s something I’ve continue to work on over the years through introspection and feedback from colleagues. I update it regularly to ensure it continues to reflect my evolving work style, preferences, and changes in my ways of working.

Working with Chris

Last update: 15-09-24

I’m really excited to be working with you and your teams.

Operating approach

Biweekly 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 document to track our agendas, actions, goals, and updates. But if you are not, then I am happy to just tackle things as they come up.

We’ll do a career session at some point in our first few months to talk about your history, why you’ve made the choices you’ve made, what your ambitions are for the future, etc. These help me know where you are in terms of your personal development interests and ambitions with respect to longer-term plans.

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 quarter, then create a plan for how we can make sure you get the time, space, and support to accomplish what you need to accomplish. I do these every 3–6 months and will share mine with everyone.

Biweekly 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.

Your teams

Please add me to emails or documents that might be helpful for me to see as a way to understand the team and day-to-day work. As work is ongoing or a team member does a great job on something, forward it or link to it in our 1:1 doc. I like to see work in progress, and I’m happy to meet with folks who have done great work so they can walk me through it, at your discretion.

Management style

Collaborative

I’m very collaborative, which means I like to discuss decisions and options and whiteboard big stuff in a group. I typically prefer to talk through concepts, review data, and explore various options before coming to a conclusion. However, I can sometimes make quick decisions that may feel rushed to others. If that happens, please feel free to share your thoughts so we can address any concerns together.

Hands-off

I’m not a micromanager, and I won’t press you for details unless I think things are off track. If I do, I’ll tell you my concern, and we can work together to make sure I understand and plan how to communicate better or right the situation. That said, when I’m new to a project or team, I often get into the work alongside people so I can be a better leader. I like to pair with individuals, and collaborate as part of their tasks to get to know more of the domain and the team.

I expect you are making decisions a lot without me. 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 help you decide. That said, if there is a big decision 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 and when they are due, and to 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 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. If you have work in progress, I’d love to be included early and often in development, but I’ll generally only weigh in when asked or on final review, even if I have draft access.

Data-driven

I appreciate the value of data and dashboards as a means to objectively gauge our progress and results. However, I’m not a fan of getting lost in excessive data or manipulating numbers to fit a narrative. Instead, let’s focus on reviewing consistent information that truly matters. Our aim should be to harness data for meaningful insights, rather than relying on it to falsely reassure us about understanding the situation or seeking answers that are more about intuition than analysis.

I also like to agree on how we do things as a group, which we can then agree to change or make exceptions to, instead of everyone inventing their own processes and frameworks.

If we’re discussing something and you know of or can imagine data that would be useful to our decision, bring it up.

Intuitive

I’m also intuitive about people, products, and decisions, which means that I’m happy to handle situations when I don’t have a lot of facts or data. Ultimately, I think I have a good instinct, but I’m not attached to it. Your job is to get my sense of something and then argue it out with me. I love a good “fight” to a better outcome.

I use my intuition a lot with respect to talent management, and I’ve been told I’m good at reading people. Again, I work hard not to judge or jump to conclusions, but I will put forward hypotheses about your team members. 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 get to know you and your team better if I know the context. If something difficult is going on with someone on your team, I’d love to know and be there to support you or them.

Strategic

I try to think about where things will end up and the straightest line to get there. 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?” I expect you to do the same. Every day, I try to ask myself, “What’s the most important thing I can do?” and do that above all else. But sometimes I get buried under email, meetings or slack and fail.

Communication

1:1s

Use 1:1s for items better discussed verbally and topics 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 me or reach out.

Email

I read fast. I will read every email I get in a day, but I don’t always respond—just know that I have read it. I will only respond if you ask me something directly or if I have a question. If you think I owe you a response, please resend the email or ask me about it. I won’t be offended.

I love FYI emails. Send me something you saw, a customer anecdote, an article, some data, or something someone on your team did. If you write “FYI” in the subject or in the forward, I’ll know it’s for my information but does not require a response.

If you add me to a team email celebrating something that I somehow missed, I’ll know that’s the signal for me to weigh in, usually with “Yay!” Go ahead and add me to things like this.

Chat

If something is important, feel free to ping me any time, even when my status is set to away. Short questions on chat are fine, but I might be inconsistent in my 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.

I generally prefer open communication over limited interaction, as staying informed about you and your team allows me to serve you better. I don’t see this as micromanagement, but if you ever feel like I’m getting too involved, please don’t hesitate to let me know.

More about working with me

Feedback

I like it. I like to give it and I like to receive it, particularly when it’s constructive. We’re in this to get better together. We’ll have an official review session, but I’ll try to be timely when I observe or hear something I think you should know about. Please do the same for me. I also like to know how and what your team is feeling and thinking, and I will do skip-levels, office hours, etc. 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 about you, your people, and everyone’s development. Please make sure that we’re touching base about your team and constantly building our skills as individuals and as teams, and that I know when there are superstars and challenges so that we can help people together.

Hope this was helpful, and again, I look forward to working together. You are all welcome to add to this document ;).