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A Guide to Working with Me, Part I: Why Every Leader Should Write a Guide

Having a “Guide to Working with Me” is a highly effective way—to head off conflicts and prevent negative surprises.

Chase Damiano
4 min read
A Guide to Working with Me, Part I: Why Every Leader Should Write a Guide

“I think that founders should write a guide to working with them […] to clarify the founder’s role: ‘What do I want to be involved in? When do I want to hear from you? What are my preferred communication modes? What makes me impatient? Don’t surprise me with X.’ That’s super powerful. Because the problem is, people learn it in the moment, and by then it’s too late.”

– Claire Hughes Johnson, COO of Stripe and Board Member of Hallmark Cards, in High Growth Handbook by Elad Gil

Founders have a huge number of demands on our time and our brain space. Between managing direct reports, running meetings and ideating with the leadership team, strategizing how to best optimize the latest product iteration, and overseeing the big picture, there’s a lot to accomplish—and usually a specific way each founder likes to go about accomplishing it. As Claire Hughes Johnson points out in her interview with Elad Gil in his High Growth Handbook, to keep things running smoothly, having a “Guide to Working with Me” is a highly effective way—and perhaps even best practice—to head off conflicts and prevent negative surprises in any new, or current, working relationship.

Even more than that, making and sharing a document that lets people know the ins and outs of how you work also helps jumpstart productivity and amiability in a collaboration. Beyond merely preventing frictions from popping up in the heat of the moment (when they’re least wanted), such a guide helps your collaborators get to know you and your working style faster and clarifies the role you expect to fill and the expectations you come in with, which makes for more efficient communication and teamwork and a better rapport right off the bat.

So how can you start creating your own “Guide to Working with Me,” and what sort of information should you include?

How to write your guide

I recommend crafting a guide that flows from general to specific points about yourself. Start with your philosophy of work to give people a sense of your personal bigger picture. Then, list your strengths and weaknesses, so they know both what you’re aware of and how to work with those strengths and weaknesses. Next, discuss your communication and productivity preferences—these are especially key for setting expectations on how the work gets done on a day-to-day basis. Then, share your leadership and decision making style; this provides people with the lens that you use to make choices that affect everyone. Finally, spell out how you like to set up a working relationship with a new team, concretely, at the start of your very first meeting.

Be sure to break out (in bullet points or bold lettering or whatever stylistic choice suits you best, etc.) any crucial points about yourself that you have found to be worth emphasizing. If something’s extra-important, don’t bury it in the middle of a paragraph where it can get lost!

To fill in this document structure for yourself, start by considering these reflection questions for each section:

  1. My philosophy of work
    • What values do I bring to my work? What’s my big vision?
    • What are the more human elements I bring to the team (e.g. fun, humor, playfulness)?
    • What do I hope you to get out of a relationship with me?
    • Do I seek to be personally close to my team, or am I more conventionally professional?
  2. My strengths and weaknesses
    • Who am I when I’m at my best?
    • Who am I when I’m at my worst? How can someone tell when I’m stressed and need patience or help?
    • What are my strengths? Am I data-driven, intuitive, collaborative, decisive, etc? How do I apply these strengths in practice?
  3. My communication and productivity preferences
    • How do I want the team to communicate with me? Do I prefer meetings, emails, texts?
    • Do I have any “must haves” or pet peeves in meetings?
    • When do I prefer to be copied on emails? And when is it okay to leave me off?
    • What are the hours of the day/week/weekend you can expect a response from me? When do I expect you to be generally responsive to calls/texts/emails?
    • When do I want folks to escalate things to me? What are the types of burning issues that need my attention right away, that I would like to be escalated immediately?
  4. My leadership and decision making style
    • How do I make decisions? Am I more fast and decisive, or slow and methodical—or does it depend on the context/stakes?
    • How and when do I share decision-making with my team?
    • What are my biases? Do I have a bias toward action, or planning? A bias toward data, or intuition and experience?
    • Am I more hands-on or hands-off? In what sort of situations?
    • What do I want updates on, and with what frequency? What do I prefer our team to have clarity on at all times?
    • When and how do I want feedback?
  5. My first steps with a new team
    • What are some of the first questions you’ll ask?
    • What are the expectations you like to establish from the get-go?

I believe in the practice of dogfooding (and in the helpfulness of concrete examples), so in my next post, I’ll share my own “Guide to Working with Me”—the one I use with my new team members and clients. Following the reflection questions above, it’s my own attempt to anticipate what someone might want to know about my working style in advance, in order to establish a productive new working relationship quickly. I consider it my “open book” on myself and how I think I work best. Check back soon.

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