Working with me documents

— 11 minute read

When I posted the other week about remote working patterns, I made an off-hand note that I based it off my "working with me" document. I didn't think much of that beyond it being some narrative framing for the post on LinkedIn, but that week I met with three different engineers in my network who independently asked me about what that document looks like.

In a way I wasn't surprised. I find "working with me" documents to be delightful when done well. As a sender, they give me a way to advocate for my preferred ways of working in a way that is non-confrontational, un-awkward, and easy to digest. As a recipient, they give me a quick ramp to following the platinum rule with a new colleague.

What did strike me about those conversations was how reticent those engineers are to the idea of putting one together themselves. They clearly saw the benefits, but the idea of putting one out there was slightly embarrassing and several reported writers block when they had thought about what to put in one.

So I wanted to put together a little guide to making one. What you'll get out of it, how to write it, what to include, and how to use it effectively. If you end up creating one, let me know! It would be great to hear about any success stories this post generates.

Why write a "working with me" document?

Any technical writing class will tell you that every document should have an intended audience and set of goals. In a way, a "working with me" document is technical instructions for yourself, so we'll start in the same place. In fact, some of the best of these documents I've read have been styled as manuals (for example, 'Mahnoor's user manual').

The best thing to do at this point is introspect what goals you have in mind, but in the spirit of inspiring that process, I'll offer some broad goals that almost everyone who is considering writing a document like this is likely to share. Specifically, after reading the document we want the audience to:

  1. Change a specific set of behaviors that will help them to work more effectively with you
  2. Be able to help you to develop and learn in your role faster

We'll look at how to accomplish both of these in more detail later on, but these are the core purposes of the document I have and what I'll be focusing the rest of this post on. You'll notice that what it means to achieve these goals will be radically different from person to person. I can't emphasize enough that this is the source of the biggest benefits of writing this document.

The honest introspection and self-awareness you need to engage in to put this document together should provide you with a lot of mental clarity on what it means for you to work effectively with your colleagues. What do you need from others to work well with them? What are your learning goals, and how can your colleagues help you with them? If you can't articulate answers to these questions succinctly in one page, you are likely to benefit just from writing this document.

Once you have written it, you'll start to get a second benefit in that it will take much less time for new colleagues to learn how to work with you effectively. Truth be told, this benefit can be more hit-or-miss because it involves other people, but in my general experience, it's amazing how effective this document can be at it's stated aims. This is especially true in a remote setting, where you don't have the normal tonal or body-language signals to learn other people's preferences. Regardless of if your remote or in-person though, a document like this one can be the ultimate shortcut for your colleagues to learn what your preferences are, which is a prerequisite to respecting them.

As a final piece of persuasion for writing one of these documents before I move onto how to write them is that they make the process of building strong relationships with new colleagues significantly easier. I attribute this to two reasons. First, is that you'll find a lot of the contents of your standard "intro/coffee" chats (you know the ones) can jettison a lot of the logistical conversation about how to work together, and can focus on more germane, interesting topics (what are your hobbies?, how did you arrive here?) that actually bring you closer together.

The second, is that it makes advocating for yourself simple, easy, and non-confrontational. Despite building a career around radical transparency, I still find this hard, and my working with me document makes it much more likely that I can make those easy-to-fulfil but specific requests when it's hardest to do so, early in our relationship.

Creating your document

First off, I want to highlight that this document should be short. As with other technical writing you do, it should use plain, simple English and be no longer than is strictly needed to achieve the goal of the document for your intended audience. In general, one piece of paper should be sufficient, excluding an appendix which I will discuss later. Unfortunately, that doesn't mean that it's easy to write! As I said, the real challenge of this document lies in the introspection necessary to write with a clear head.

The best advice I can offer is to treat this document as an iterative, evolving one. Sometimes, after reflecting on a particularly frustrating day or difficult situation at work, a new bullet point for my document will suddenly come to me. I've been working on my own document for around three years now, and I imagine in another three years I'll still be adding, removing, contracting, and simplifying it. I see this as one of it's joys. It is a way to facilitate my own self-awareness.

Over that time, the general structure that I've come across and really like is two headings with a series of short, one to two sentence bullet points. Those headings are:

  • Tips for working with me
  • What I'm working on and how you can help

Those correspond to my two goals, and are hopefully self-explanatory.

The bullet points are the vast majority of the document but there aren't all that many of them. Remember that your audience has a lot of other things going on. In total, I have 13 bullet points in my document across both headings, which puts me well under a full page on Google Docs.

Every single bullet point comprises a specific request. I feel strongly that if you can't articulate a request for changed behavior, even an extremely small one, the point you're making isn't worth your audiences time and shouldn't be included. Often times, I will have one sentence for some context or explanation, and another for the request itself. My general preference is that the request goes first. Remember that when writing in bullet points, your reader skims vertically much more than horizontally, so positioning your requests on the left of the screen makes them much more likely to be read.

Here's an example bullet point under the "Tips for working with me" heading:

If you are giving me feedback, please present it earnestly. While I enjoy joking/sarcasm in general, I despise it when you are giving feedback.

And here's an example bullet point under the "What I'm working on and how you can help" heading:

If you ever feel like I am bottling something up, please encourage me to speak openly about what I am feeling. I am good at being candid about my opinions, even when they are inconvenient. I am less able to candidly express my emotions, especially when they are negative ones.

I think what works about these examples is their simplicity, specificity, and openness. The language is simple, easy to read and comprehend. Because it can be vulnerable to write openly about your own needs, you will be tempted to hedge by using more flowery language. Resist this urge as your document has a very short window with it's reader and you need to communicate your needs to them plainly and succinctly.

As mentioned already, it is critical to have a specific request. Always remember that this document has goals. You should know what behaviors you're trying to change in your target audience. Failing to center this goal is to write purposelessly.

Finally, is openness. If you have a set of goals specific to you and you write with those goals in mind, this should come naturally, but if you fail, it will come through in your writing. People can tell if these documents are honest expressions of your needs. If the document is beige, unopinionated and unclear, you will have wasted your audiences time.

While that's all relatively simple advice, it is also a simple document when you get to the heart of it. To recap, write no more than one page. Use bullet points and simple headings that convey your goals and write simply, specifically, and openly.

The last thing I want to talk about in this "how" section is the appendix I alluded to earlier. This is totally optional because I appreciate that sometimes these things can be extremely personal, and can be used against you in a psychologically unsafe workplace, however personally I strongly believe in copy-pasting my last performance review into my document.

In a good (again, by which I mean psychologically safe) workplace, this should do two things for you. First, being extremely transparent about your performance review helps your colleagues to calibrate it. In the past, in sharing my performance review candidly, my colleagues have identified errors in in both in a positive and negative directions. Consistently hearing that some feedback is overblown let me steer towards areas which colleagues have identified as true blind spots.

The other positive I've found from doing this in the past is get buy in from your peers to helping you with the items in the "How you can help me section". People respond well to the vulnerability shown by sharing your performance review, and are more likely to help you with X knowing that it's the thing holding you back from getting that promotion from management.

Introducing your document

In my conversations with other engineers and colleagues, the embarrassment of introducing the document was often an even bigger factor than writers block when it came to avoiding writing it. Happily, I have found the process of actually introducing it to be easy and embarrassment-free. In fact, I receive positive feedback on the document so consistently that I positively look forward to sharing it and will seek opportunities to do so.

I've found that the perfect way to introduce my working with me document is during introductory coffee chats or our first 1:1 meeting, whichever comes first. Invariably, I love to ask some variation of the question:

What are some working preferences you have which you would like me to respect?

The first reason I do this is because I'm genuinely curious, and I almost always learn something from their answer which genuinely helps me work better with them going forward. The other reason I do it is that they (again, almost always) ask the same of me, which tees me up to reply:

I have a few! I actually have a "working with me" document which I'll send you after this and would appreciate you reading. I suppose in the meantime one that's important to me is…

I've had a lot of success with this framing. Normally, hearing one of my opinions and knowing there are more out there somewhere leaves them curious to read it, and if I send that link shortly after our meeting, I generally see them view the document instantly. I also normally get a few follow-up questions via direct message or the next time we chat. People tell me all the time that they're grateful that I shared it as a document, and that they want to put one together themselves. I take that as a relatively solid indicator that this practice is well received, and appreciated.