Tell Me How You Work

Startups are fast-paced, dynamic, and often unstructured environments. In such a setting, figuring out how to best work with the people around you is essential for success. Easier said than done, especially when an organization is changing fast and growing quickly.

A simple hack: Get everyone to write a “Working With Me” guide:

It’s a personal guide by each individual to help their colleagues understand their preferred working style, communication habits, strengths, and areas for growth better. It's designed to improve collaboration by providing insights into each person's unique preferences / needs.

If done right, implementing it across your startup can be extremely powerful and is highly scalable / compounds over time (as with most things captured in writing). Specifically:

• Leads to better understanding of each others’ preferences, habits and shortcomings, thereby improving how you work together
• Allows to set clear expectations, resolve potential conflict up front and creates accountability as it forces proactive communication and increases transparency
• Helps individuals to shape their personal brand / leadership style and founders to shape company culture
• Significantly streamlines new team member onboarding / sets them up for success much better / faster

Even if you’re just the founding team, start using them. Why?

Reflecting on and documenting your working style and communication habits not only benefits your team members but you’ll likely learn a thing or two about yourself as well. Increased self-awareness is never a bad thing ;).

Claire Hughes Johnson, former COO of Stripe (2014 - 2021), is one of the well known strong advocates of “Working With Me” guides. In Elad Gil’s High Growth Handbook, she shares how she implemented them at Stripe:

I shared it with everyone who was working with me closely, but I made it an open document. It spread quite quickly through the organization. It made sense, because I was new, I was in a leadership role, people wanted to understand me. And then people started asking, “Well, why don’t we have more of these?”

It’s been a little bit of a viral, organic adoption, and now a lot of people at Stripe have written their own guides to themselves. I’ve even had folks who are not managers but are on my team write me these guides to them. And it’s been super insightful. So I’m a huge fan.

Here’s Claire's full “Working With Me” guide (click on the image):

Key to a good guide

A good guide is as specific to you / as personal as possible.

Sounds easy enough? It’s harder than you think.

Give it a try - write a first draft of yours and then read it again.

Does it include generic statements that could apply to anyone? Like:

• “I prefer a structured approach to work” or
• “I value clear and concise communication”

This doesn’t tell anyone anything insightful about the way you actually work.

How about the following instead of the first statement (from my own guide):

I like to spend time thinking and planning upfront before doing the detailed work. When you’re working on a topic with me, what works best is:

• You think through a structure / plan / outline / key points upfront and (ideally) start capturing high level thoughts in writing
• We then think through it together to align on direction - potentially in a few iterations where the first ones can be asynchronously (I strongly believe in the power of writing)
• Once we’re aligned on the direction, you dive into the detailed work independently

Writing a good guide also includes being open about your shortcomings. Openly acknowledging them demonstrates vulnerability, which encourages support, mentorship, and empathy from others. Plus your colleagues are likely more open with you too.

Julie Zhou (a former VP of Product Design at Facebook) has a “User Guide” (as she calls it) that is a great example of being both personal and vulnerable.

While both Julie's and Claire's documents are extensive (as one might expect in larger organizations), even creating much simpler versions can go a long way at a startup.

If you need another reason as to why to start implementing them at yours, here’s a good one I came across when I did some reading to refine this post:

How-to guides are standard for cars, appliances, televisions, lawnmowers, and many other products. Humans are far more complicated than those things, so why shouldn't we also come with sets of instructions about how best to work with each other?

That was the thinking behind a personal owner's manual project that we recently rolled out across the leadership team and plan to expand companywide. Because no two people are the same, such upfront transparency about individual work styles and preferences can only foster workplace harmony and productivity.

It seems futile to merely guess at how each of us likes to work, what motivates us, what annoys us. This is especially true now as the rise of remote work demands fresh approaches to keeping people connected and feeling personally invested in one another as they bounce from Zoom meeting to Zoom meeting.

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