An Autumn with Out of Office Hours

I registered for Out of Office Hours in July, then was invited to the August cohort, so I’ve been in the mentoring cohort for the last four months. I plan on mentoring there for as long as I’m useful - the commitment is so easy and I have an opportunity to have really uplifting conversations a few times a month.

So far, I’ve had 11 calls - two were scheduled in that time but the mentee never showed up. One thing to remember: the commitment is low on both sides, so you will occasionally have people bail on the meeting last minute or show up with no real topics to talk about. But for every one of those, you will most certainly get five others that leave you buoyant and appreciated.

It was very easy to set up as a mentor. You fill out a bio, wait to be selected, then you just get mentees adding themselves to your calendar. It’s pretty ideal from my perspective. Coming from the past where I would spend time attending meetups and conference talks to try to help the software engineering community, I feel almost guilty that I do nothing and still get to mentor and give back.


The majority are early in their careers, or switching roles or careers. Most want to know how to interview or what interviewers are looking for or what course they should take online to look best in an interview. Those formed the majority of a category of questions I would call ‘what should I…’ questions. These are the hardest for me to answer, because I only know these people for the call we have together. Largely, for these, I just end up asking them questions about what they want in the future and together we can arrive at a recommended plan based on what I have seen work or not work in my own past.

Others ask a second category of question about what I prefer, what I do in certain situations, etc. I have been thinking of these as ‘how do you…’ questions. These are my favorite, as I can launch into a story about my specific experience and then together we can work to shape it into something that they can synthesize into their own decisions. These are the most rewarding conversations - I don’t feel like I’m being overly prescriptive, and I feel like my own years of experience can save them mistakes and headaches.

There has been a reassuring ratio of women and minorities on these calls. I’m not sure if it’s just a sign of this generation of software engineers (best scenario), a factor of the medium, or self-selected from my bio, but it’s been a happy surprise.

What I Would Ask

I wish more people would come with concrete examples of how they have been operating now - that’s largely what I begin asking about and it usually takes them by surprise. I have a field on the booking form for the person to detail anything I can read up on before the call - their website, their current company, anything. Only about half of them have put anything into that field. I am going to be making it required in the future, just so that I can know they have spent some time thinking about what we should talk about together. (I’ve had a few people clearly forget we had scheduled a call).

No one has asked me to review their resume or to practice interviewing or what programming language they should learn next. That’s great. All of our conversations have been about how their career path will be perceived, communications strategies, etc. That’s good! Those are the toughest topics, in my experience.


I think this pandemic and forced-remote situation is a golden opportunity for normalization of mentoring and calls like these. Before, mentoring revolved around meeting someone at a conference or presentation and then coordinating coffee or a drink after work or whatever. Now, you have only one way - to schedule a low-friction zoom call with anyone, anywhere in the world! I have had multiple international mentoring calls and I’m hoping more people realize this opportunity! We now effectively have a normalizing force to give us access to anyone else in the world for free.