I’ve had a sign up for open online career mentoring on my site for quite a number of years now (in addition to running similar career clinics in-person). As I’ve gotten more and more traction internationally on the program, a lot of senior folks have asked how to set up a program for office hours similar to mine, and for tips and trips to make it a success. It’s not terribly complex, but here’s a run down:
Technical How-To
I use the free Calendly service to schedule my meetings. If you have a paid calendar system including Office, you might have more features available through them. Calendly works for my needs.
Once you have a Calendly instance, it will link natively to both your online calendars and to your Zoom account in your configuration. Calendly will put meetings on your calendar with a unique meeting ID. It will also send reminders to participants and track no-shows and cancellations. Once you create a meeting type and description (like “Mentoring”), Calendly provides an easy web interface for attendees to schedule and reschedule their own meetings, and immediately receive a calendar invite from your calendar provider of choice with a Zoom link.
The most important setting outside the linkages is your calendar availability. You can and should configure Calendly to check your blocks and remove those from open time slots. You will also want to set your overall available hours for meetings – perhaps on a weekend or evening. Between those two settings, you should now only advertise the times you are really free and want to meet.
This isn’t a particular endorsement of Calendly – most apps function in a similar way and I wanted something free. The vital things are – there’s a website where people can sign up with no interaction or time waste from you – and that service handles integrations with your availability and your video conferencing app. You will burn out quickly soliciting people manually and setting up meetings.
The Logistical Nitty-Gritty
I set my meetings for 30 minutes long, with up to 45 days rolling advance registration, and requiring 18 hours required notice for sign up. You will probably want to adjust for personal preferences, but it has worked pretty well for me.
As part of the configuration in Calendly (and office, and similar programs), you can ask the registrant a number of questions. I firstly describe my services as follows:
This is a way to book time with Lesley for 1:1 career guidance. You can see Lesley's credentials here: https://www.linkedin.com/in/lcarhart/
You can select to use the time in several ways:
Discuss and comment on your existing cybersecurity resume (which you can screen share), or discuss issues you are having with cybersecurity interviews. Lesley can only coach on US format resumes, not international CVs.
-OR-
Discuss your future or current career goals, plans, and concerns related to cybersecurity jobs. No resume required. The conversation can be open ended, or you can provide topics in advance. Lesley’s specialties are generally blue team.Note that I describe clearly what service I provide, my limitations, what I can do and am qualified to discuss, and what people might want to get from our time.
Then, I require an email and the following four pieces of information:
If applicable, do you have a resume to screen share (even a rough draft)?
Please share anything that will help prepare for our meeting. What would you like to discuss? Will we focus on resumes, interviews, or general career advice? What's your background?
RESUMES: I understand that Lesley only reviews North American style resumes, and will not take the place of a professional grammar and style editor. Technical content only will be reviewed.
I will contact Lesley to reschedule or cancel as promptly as possible if i can’t make it, so someone else can use the time. No shows + no messages will never be allowed to register again.The first two questions help me understand how I will help in advance. The second two questions are protection for me. People often don’t respect you or your time when providing free training or mentorship.
I firstly want to make it clear that I cannot provide services outside my area of expertise. I secondly make it very clear that I have a hard rule where I will ban no shows permanently. This seems harsh, but I have about a 20% no-show rate to my appointments and that is down from a 30-40% no-show, no-message rate before I added this explicit question that requires a written response. Its dismal losing part of your weekend to people who just don’t show basic courtesy, when a lot of people wait weeks for help. Now, when people don’t show up, I send them a quick note to ask if they are having technical issues, wait a few minutes, and then mark them as a no show and block their registration.
It’s not a terribly bad idea to ask for a very small deposit or donation in advance of meetings. My immigration status no longer allows this, but it did make my show rates better and I think it makes people put a quantified value on your time and experience.
The Actual Sessions
The people I talk to want a variety of assistance, but there are some commonalities in the top concerns:
- Help building a resume / CV that passes modern ATS and HR screening – and is also effective once it reaches a cybersecurity hiring manager.
- Guidance in unpacking why job interviews were or were not successful.
- Unbiased feedback on next career moves and/or appropriate education and certification paths.
- Help choosing a niche of cybersecurity work when everything seems interesting from the outside.
- Assistance in navigating a very poor junior cybersecurity hiring market – and confirmation that it really is as bad as it appears.
- Guidance on toxic workplaces, burnout, and poor career and skill growth opportunities – and again, unbiased confirmation that it really is that bad.
- A counterpoint to employer or educator gaslighting about [lots of issues].
- Guidance on moving to a new state, region, or country in cybersecurity – including the market and cyber community.
- Help in deciding whether to stay technical or move into management or governance.
- Aid in moving into small and underrepresented cybersecurity niches.
These are just a few things I get questions about almost every week, that you can expect to hear about unless you explicitly ask not to discuss them.
Final Thoughts
The people you will meet with are at their most vulnerable. They are sometimes waiting a long time for outside perspective about incredibly personal and challenging career issues. Be patient and empathetic. Be an active listener.
However, also be efficient with limited time, and make sure your mentees get a practical benefit from your session – sometimes I have to be a bit blunt (I explain why, and apologize). You are going to see a shocking amount of ugly babies – messy resumes, implausible career trajectories, and educational backgrounds that border on scams. We are sometimes the only honest people who can get these folks back on track when they are surrounded by sales pitches and fud. The market is absolutely dismal out there for cybersecurity jobs, and all decent people deserve a fair shot.
Source: Lesley Carhart
Source Link: https://tisiphone.net/2025/09/01/open-online-mentoring-guide/