User manual for Sean O’Reilly

My personal and professional life is becoming increasingly both complicated and demanding. To maintain my an uncluttered mind and keep my creativity high I have a personal assistant (Pearl) and an Executive Assistant (Jenny). If I put you in touch with either to organise something, it’s not because you or the something is a lower priority. It’s quite the opposite, ensuring that it will definitely happen without compromise.

I try to be as responsive to emails and other communication methods as much as possible. However, some things just need a little more thought put to them than a quick response justifies. If you haven’t heard back from me within a couple of hours, it’s likely I’m putting that response on hold until I can dedicate the right amount of time to composing a response that your message deserves.

I like to text and call. My calendar makes ad-hoc phone calls a little tough to reach me outside of an appointment, but overall I’m usually most responsive by phone. If you want a response from me quickly or want to have a chat about an idea or debrief on something, don’t hesitate to text or call me, even it’s outside of works hours (although response time dilutes further from work hours).

My mind tends to not switch off outside of work hours or even on public holidays. It’s likely there will seemingly random flurries or individual but occasional communications coming from me at all hours of the day. I’m usually either inbox zero-ing or getting excited about something. if it’s out of hours I’d be happy for you to respond but don’t feel like you need to reciprocate, especially if it’s a personal inconvenience.

I like to start the week early on a Sunday night. Usually, after dinner I spend a few hours inbox-zero-ing, organising my calendar, and getting everything setup for the week. I’ll be very active on email and Slack during this time so if you have a similar habit, in most cases you can count on me to be responsive during this time period of the week.

I’m quite impervious to people that are trying to say things without actually saying them. For some reason I find it harder than most to pick up on that kind of thing. I like to conduct both my personal and professional life in an extremely transparent and straight-forward manner without hidden agendas or subtle suggestions. I like it when the people around me to behave in the same way.

If you’re proposing something to me, I’d like it to be presented with some context. This usually involves a problem definition, a rough estimate of the scale of the problem, the opportunity cost, the proposed solution, the cost of the solution, and the other solutions that didn’t make the cut and why not. Not all of these are always possible but the more I have the better (and faster) I can make decisions.

Coming from both startup and professional backgrounds where I’ve designed, built and delivered a lot of pitches, I have an acute appreciation for succinct and direct conversations and discussions. I prefer if someone takes more time to succinctly communicate something than try to communicate it quickly without structure and with multiple contexts. Clear concise communications are always appreciated.

I really like to lead from within as opposed to leading from the front. That means having everyone empowered to feel they are capable of contributing to decisions made within the company irrespective of title or experience level. I will often defer decision making downwards to my team so we can collectively decide what to do next and how to do it for this very reason.

I like to be very direct and timely with my feedback and likewise I prefer it when people carry the same principles with feedback for me. I will always try and deliver feedback with an observed reference point as close as possible to when it was observed. I believe the further the distance the more diluted the impact of the learning so I’d also like you to do the same for me.

I try to ask a lot of questions in meetings, especially when there’s reference, question, or statement that I don’t understand or know the answer to. Some people see this lack of knowledge or understanding as a weakness, it is the opposite. If you don’t understand something or don’t know the answer, do not hesitate to ask about it or make it clear that you don’t know.

I have a tendency to leap ahead and jump into solution mode. This is something that my mind does continuously when I’m being presented with problems or opportunities. Occasionally it goes beyond just thought and I start listing out options and solutions. If this isn’t what you’re looking for or I’ve made some leaps that I haven’t articulated, please don’t hesitate to slow me down.