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It was 2021. One of my CEOs pinged me with a request. He asked if I would get on the phone with a prospective candidate to share my thoughts about what it would be like to work at the startup and with him in particular. “Please share my user manual,” the founder said to me.
He meant it figuratively at the time, as the founder in question had no such document. But I loved the idea and gladly agreed. Having spent real time with the senior team, overseen 360s, and attended board meetings, I knew the founder well, and I felt reasonably well versed in the organization’s culture.
I had known the CEO for a long time. What I had thought to share came to me easily, but in reflection, it was less of a user manual than a disorganized set of quotes resembling a poorly delivered movie review. A good user manual has a consistent structure and is easy to follow and use. What might great look like?
After a bit of poking around, I was embarrassed to find that this is an established topic — from Adam Grant to Facebook to a litany of consulting shops, there is ample reading about how user manuals might be a useful management tool.
But specific to a startup CEO? That seemed to be a gap. The template below is what I now encourage my founders to compose. I have also included my personal user manual as a live example. Enjoy.
Title (one-line description of what makes me tick)
Introduction (single paragraph explaining the purpose of the manual and how it can be employed)
How I prefer to communicate and receive communication (mediums, style)
Trigger topics (areas where I’m particularly sensitive)
What I expect from those I manage (how to thrive as my direct report)
FAQs (basic context on my life)
Something curious worth knowing about me (to help you get to know me better)
Utilitarian ethicist who is always well intended, not always gentle and often up for a laugh.
Introduction
The intent of my user manual is to speed up the building of trust and rapport between me and those with whom I work. This user manual does not reflect everything about me; it is meant to be a starting point for connection and relationship.
Who am I at work? I’m passionate. I work very hard, and I love what I do. What I care most about is the health of our team and delivering value to those who trust their startups with our firm Enjoy The Work. Oh, and I’m a relentless troll.
I believe that the health of the team correlates strongly with the performance of the company. And to foster a healthy team, I follow a simple formula: candor + reliability = trust.
Toward that end, I will say the quiet thing out loud — no matter how difficult or unpopular — but will do my utmost to share my thoughts with kindness. I am not a telepath and don’t expect others to be; I therefore do best when everyone speaks their mind and asks for what they want.
When I make a commitment to someone, I do my utmost to keep my word. If I come up short, I’ll own it and try to do better.
How I prefer to communicate and receive communication
In writing, I prefer well-written, concise language. Poor spelling and grammar feel unprofessional and sloppy to me. I don’t require great acts of prose, but I see clear communication as a sign of clear thinking.
Verbally, I respond best to those who speak their mind, show up curious, and know how to listen. I try my best to do the same. I struggle with expressive thinkers who use a lot of words to make a point (but that is my weakness, not theirs).
I’m highly responsive — mostly because I am addicted to my phone — but I don’t expect the same from others. If you email me, I’ll answer you sometime that day. If you send me a Slack message, expect a response within a few hours. Text or call me? I’ll respond immediately assuming that you need bail money or worse.
Trigger topics
I am particularly reactive to:
FAQs
Something curious worth knowing about me
My family has been in and around gambling in one form or another for four generations…
My father was a casino executive and a world-class poker player, my first career was in the casino industry, and my sister is a gaming attorney. I was playing poker by 5 years old, went to the racetrack by 12, and hit my first slot machine jackpot by 15. I had no idea any of that was strange until I got to college.
Now, here’s my question: After reading my user manual, do you think you have a better sense of me? I hope you do. How much impact might such a simple device have if allowed to proliferate across an entire team? Give it a try, and, please, if you use my template, send me a note on LinkedIn. I would love to hear about the experience.
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Founded in 2015, Enjoy The Work is a San Francisco-based startup advisory firm serving startup founders and CEOs worldwide.
