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A Guide to Working with Me, Part II: My Guide

Below is my own “Guide to Working with Me.” It lists my preferences and habits—but nothing is a command or non-negotiable.

Chase Damiano
6 min read
A Guide to Working with Me, Part II: My Guide

In Part I of this series, I laid out my case for why every leader should write a guide to working with them, and outlined the steps on how to write your own effective guide.

For starters, writing and sharing your guide will help solidify and communicate your values. As a public document, it helps create the psychological safety required for accountability. because when leaders are transparent about their productive working habits, it empowers employees to call them out when they drift.

A public guide helps everyone start working together productively and make any necessary course corrections much faster. Below is my own “Guide to Working with Me.” It lists my preferences and habits—but nothing is a command or non-negotiable. Any successful working relationship will see give-and-take.

My philosophy of work

“What is your general perspective on work and what success looks like?”

I believe that trust is the key element in a high-performing team, and that when clients work with a team where everyone trusts one another, the growth and scale snowball for everyone.

  • To build trust, I try to look past the conventional walls of “business” and “professionalism” and take an inclusive, whole-human approach. I think real human connection is possible at work if we are simply allowed to be ourselves, so I strive for a culture where everyone is comfortable and doesn’t have to put on the “work mask” around me.

My strengths and weaknesses

“What do you bring to the table? Who are you when you’re at your best? Your worst?”

When it comes to strengths, I know that any productive habit can become unproductive when taken too far, and that focus in one direction creates blind spots in others. But awareness is what allows us to strike the balance we need between our strengths and weaknesses. Here are my main competencies (and their evil twins):

  • Achievement-oriented. I like to set goals and go get them. I’m a realist and have become skilled at identifying big goals that yet become reality. This can make it difficult for me to “play” and engage in activities that don’t feature big, explicit goals.
  • Focused. I prefer depth on fewer initiatives to narrowness on many initiatives. This helps me prioritize the right goals, not just any goals. However, I sometimes “zoom in” too hard on my short list and end up missing something else.
  • Strategic. I’m stronger at designing and architecting the pathway to a solution than I am at personally executing on the work. This sometimes slows things down when the solution should be to “just do it.”
  • Analytical. I prefer quantitative, data-driven approaches over intuitive thinking. On the other hand, I know that numerical analysis alone can miss the “human” side of the equation. So instead of thinking, We need to maximize the numbers, I think, We need to optimize the numbers for their real-world implications.
  • Organized. I thrive at making (and using) plans, agendas, notes, and records. I prefer proactivity over reactivity. The risk here is: I may not react as quickly to rapidly emerging opportunities.

At my best, I am an explorer: visionary, intuitive, and creative. I’m fully present, analytic, strategic, and energetic. I’ll find entirely new ways of perceiving and doing things.

But of course, we are all a balance of light and dark—and the most important thing is to be aware of it. I know that at my worst I can be short-sighted or apathetic. I might ignore relationships or create a sense of self-importance and seek status to feel good. I’ll become too busy and overly structured. Here, I ask my team members and clients that if they notice this behavior, it means I need help. I invite you to call it out! By doing so, you’re directly impacting my personal development, so thank you.

How I communicate and how I’m productive

“When it comes to communication and productivity, what do you find most efficient? What expectations do you have?”

In general, I reserve email for interfacing with clients. I find that emails and texts create distractions or slow debates around what the true priorities are, which is why I don’t prefer these for internal communications.

  • Instead of texting or emailing internally, I prefer to have hyper productive meetings and use Notion, which allows you to directly tag and communicate with team members in action cards and notes, as the primary communication channels for collaborative work.
  • I tend to check email in the evenings, in a batch. A one- to two-day delay on most email communications is typical for me.
  • I might send messages out over Notion late at night or on weekends—but people I work with are not obligated to respond or even pay attention to notifications in their off-hours.

This last point is important for me to hit home, because I understand that when someone’s boss sends a late-night email, an employee may naturally feel the pull to respond and show that they’re “on top of it.” While this is a good quality, there are other ways to show it that don’t mean cutting into personal life.

With meetings, I live and die by my calendar. I consider it the record of truth for where my time goes. (I’m even known to back-update calendar invites to reflect the actual time spent on a task!)

  • I am generally available for meetings between 10am and 6pm, Monday – Friday, with some exceptions.
  • I prefer selecting a dedicated, recurring time each week where we can hold a one-on-one. (More thoughts on how to optimize meetings here.)

How I lead a project

“What’s your leadership style? How do you approach decisions? How can I give you feedback?”

I find this three-pronged approach highly valuable for leading a project:

  1. Clear goals. Every project must have a clear objective and clear ways of measuring progress towards it. A project without a goal becomes costly, inefficient, and never-ending.
  2. Accountability to outcomes. Every project must have the right team to execute it, with each outcome assigned to a single individual, along with an expected completion date. Because an outcome without responsibility never gets done.
  3. One source of truth. There has to be a centralized location as the single source of truth for all information on the project. Project status updates must be reportable and transparent, with all updates posted to this single project board. This dramatically cuts down on time wasted simply asking each other for updates.

Decision making

  • I like to make small decisions quickly and decisively. If I make a decision quickly, it means I’m well-informed by data and experience or that the decision is inconsequential or reversible.
  • For bigger decisions, I speak to my mentors and gather different perspectives before deciding. If I take time with a decision, it should mean I’m missing significant data or the decision is irreversible.


  • I like to hear any and all feedback on my performance, and I see each day as an opportunity to get better. I ask anyone I work with to please share feedback with me often. You’ll see me actively invite it. I find this old adage constructive: “Praise publicly, but criticize privately.”

As we start working together

I thrive when others lean on me to help them think through their own goals and identify the barriers to reaching their potential. I find that my client sessions really hit the ground running when clients bring their objectives to the table at the outset. Before diving in, however, I first try to lay out general working agreements, based on these questions:

  • Based on your own work preferences, where do you see alignment in our working styles? Where do we differ?
  • Do you anticipate any conflicts or challenges?
  • What could we enact now that works for both of us?

My working agreements are well-intentioned and aspirational, yet realistic. I know that agreements sometimes need revision, and if frictions arise, I think it’s important to call them out and put them on the table. As long as we maintain sight on the bigger goal of building a better company through effective teamwork, any working frictions will be easily ironed out.

Guiding the guide-writing

Since writing my own guide and putting it into use, I have found that not only do the people I work with better understand where I’m coming from and how we can best work together—I too can better see for myself where my actions add up and don’t.

Writing, maintaining, and sharing my guide has made for better collaboration with my team and clients, and greater self-awareness for me. I encourage you to implement your own. Feel free to get in touch with me for help crafting your own guide.

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