The following is the “user manual” I first wrote while running BetterCloud in 2016. I later updated this user manual in 2025 when I launched Not Another CEO and began advising more CEOs on how to roll out user manuals in their organization.
To learn more about the impact of user manuals, please check out the article User manuals: transform the way your company works in less than 30 minutes.
If you want our help in running this exercise at your company, you can find time with our team below. We have done this for teams of all sizes, and we would be delighted to help you.
Question set #1: About me
Goal: These questions help uncover the personal context that often goes unspoken but significantly affects team dynamics. They create space for authenticity.
What are some honest, unfiltered things about you?
I don’t have any hobbies (which I know is unhealthy). All of my energy is devoted to work and my family. I usually wake up around 4 am and start sending emails.
When I decide to get involved with a business, I tend to treat it as if it were my own; I don’t know how to operate any other way. In general, I have very high expectations of people, and I will challenge them to live up to those.
What drives you nuts?
There are a couple of things. The first is that if someone agrees to do something and doesn’t end up doing it. If you say you’re going to do something, do it. This is my biggest pet peeve. The reason it’s so frustrating is that I have so much going on that as soon as someone says they’re going to do something, I remove that from the to-do list in the back of my brain.
Another thing that drives me nuts is when people misrepresent something that was said or happened. It could be a customer telling me that my salesperson said we would do something that we didn’t do. Then I check the call recording and see that it was never promised. It could be an investor who tells you they’re going to help you get a bunch of customers, but they never even attempt to get customers for me or anyone else.
What are your quirks?
I tend to repeat myself a lot. It comes from talking through ideas and problems out loud. It definitely annoys some people. I don’t know why, but it is actually how I come up with my best ideas.
For example, when I’m working with a CEO on a pitch deck: we'll discuss what each slide should contain, and I’ll continually refer back to the first slide to review every slide up to the one we’re currently working on. I do it to ensure that it’s flowing well, but I will do this 15 times in a relatively short meeting, and people probably get tired of hearing me talk through it.
How can someone earn an extra gold star with you?
I get an actual adrenaline rush from coming up with something innovative, even if it's something small, and I love people who can both come up with those innovative ideas alongside me and those who can take those ideas and implement them. I love when someone isn’t scared to try something that no other company has ever done, or just something that requires them to go against the grain.
What qualities do you particularly value in teammates?
Three attributes that I love in the people I work with are an infectious work ethic, intelligence, and creative problem-solving skills.
What might people misunderstand about you that you want to clarify?
Most people think I’m an extrovert because of my energy and the way I present myself in group settings, but the reality is that I’m an introvert. I get my energy from being by myself. I’ve learned to tap into my extrovert side when needed (which is a lot), but I’m pretty antisocial all other times because I need to recharge.
Question set #2: Working with me
Goal: These questions aim to reveal your preferences for collaboration, communication, and decision-making. They provide your teammates with a roadmap for working with you more effectively.
How do you coach people to do their best work?
I think one of my superpowers is being able to identify the importance of anyone’s work. I know how to tie anyone’s job to something that will move the needle for their company. My approach to coaching people is to make sure they’re aware of that. I also enjoy brainstorming with them on how they can improve their jobs or projects. I encourage people to strive for excellence and push themselves to go above and beyond.
What’s the best way to communicate with you?
Email is how I manage my task/to-do list. If you would like me to do something, please send me an email about it. I try to work through my email and get as close to inbox zero every morning (I usually get there once a month). I’ll communicate via Slack, WhatsApp, text, or phone, but things fall through the cracks there.
How can someone best persuade you or get buy-in?
It doesn’t take too much to convince me to try new initiatives, but it takes a lot more to convince me that it makes sense to make a bigger and longer-term investment in something. I want to see the data that backs it up.
How do you like to give feedback?
The easiest way for me to give detailed feedback is in writing. I find that it is easier for me to collect my thoughts, give feedback in a constructive way, and identify examples of behavior. I don’t mind doing it in person, but I like to have some time to prepare the feedback before the meeting.
How do you like to receive feedback?
I like people to be straightforward and give me feedback directly. I’m not easily offended. I know that I don’t know how to do everything and can’t see everything that is happening in the company or market, so feedback is always welcome.
To learn more about the impact of user manuals, please check out the article User manuals: transform the way your company works in less than 30 minutes.
If you want our help in running this exercise at your company, you can find time with our team below. We have done this for teams of all sizes, and we would be delighted to help you.