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As I had mentioned previously, this year, I’m going back to school. Not to take classes but to teach a course at my alma mater, Fanshawe College. I did this about a decade ago and thought it was interesting, so I was excited to give it another go. Additionally, after a friend mentioned that their kid wanted to learn Python, I developed an Intro to Python aimed at high school students that I’m teaching weekly. I thought that this would be good fodder for the State of Security. So, whenever I have something interesting to discuss, expect to find it here.

I really want to get into interesting technical discussions with this series, but I feel like there are serious problems in the soft skills area that still come up each week, and they are important enough to merit a conversation.

I’m going to set up this post with one of the oldest stereotypes that I know. Picture this: A car pulled over on the side of the road, nothing but open fields in the background. A man has a map spread out on the hood of the car. He’s got a puzzled look on his face, and there’s a question mark floating above his head. A woman leans out the passenger window, and a speech bubble contains the text, “You should have just asked for directions at the last gas station!”

It’s a common stereotype, the man who refuses to ask for directions. It’s more than that, though. It’s people that don’t like to ask for directions. I’m sure that a psychologist could talk about this in great detail and explain the emotions that drive us toward getting lost over asking for help, but I wanted to look at it from cybersecurity, both in my day job and with my students.

From the Real World

A member of my team has been struggling with a task for a bit, but I didn’t know they were struggling. I was curious to know why a project was taking longer than expected, so I reached out to ask. The response was surprising. The individual was stuck but opted not to ask for assistance. They were trying to figure out the problem on their own and didn’t realize that the loss of productivity was more damaging than asking for help would have been. We talked about the issue a bit, but mostly, we talked about the importance of asking for help.

We have been trained as a society to not ask for help. We see this in the stereotype of men who won’t ask for directions, but we see it more obviously in the growing mental health epidemic. We have this image in our heads that successful people don’t ask for help. I’m just as guilty as my employee… I have sat and spun my wheels many times rather than ask for help. I like to think that over the years I’ve wised up a bit and now I’m more inclined to ask for help, but I still need to remind myself to do it.

I think this is a particular problem for people starting out in their careers. You don’t want to come across as lacking knowledge, but that’s a misconception. As a manager, I’d much rather you admit to a deficiency in your knowledge than be left to think that your time management or problem solving skills are subpar. It is OK to make a mistake, it’s OK to be wrong and it’s OK to ask for help. We don’t say that enough, and in an environment that puts emphasis on recognizing successes, we appear to discourage it. While we need to recognize successes, it’s equally important to acknowledge people who ask for help, who recognize their own shortcomings or lack of knowledge and know how to overcome it.

To the Classroom

Not only did I encounter this at Tripwire this week, but I also encountered it at the college. I actually spent some time speaking to my students about the importance of asking for help, explaining that there’s no shame in it and it’s not a negative. When someone is learning, seeing them ask questions lets me know that they are making an effort to understand it. Discussing this subject with my team, one of my colleagues pointed out that even if you do understand it, asking questions can be beneficial because others may not understand and you are helping them.

It’s no secret that there are always students who do better than others, and by the time you get to your final semester you know who those people are—just as you quickly learn in the workplace who the rock stars who can answer your questions are. Seeing those standout students ask questions can inspire other students to ask questions. If someone you respect is willing to do it, it makes you more likely to do it.

The problem is really two-fold. Not only do people avoid asking for help because they think they are making a good impression, they also do it to avoid asking for help in front of their peers. A lot of my students want to work on problems one-on-one rather than in front of their peers. While I’ve humored these requests thus far, I wonder if I’m doing them a disservice. Some of my best conversations and the times when I’ve learned the most have started because of conversations in groups designed to answer questions and get guidance. Additionally, if they are having that problem, it would seem likely that others are as well.

What Can We Do?

One thing that happens in the workplace is that coworkers tend to develop their own playful style of picking at each other’s flaws, questions and mistakes. While that is fine and an important part of team-building, it can be disconcerting for newcomers to the team. They may not know how you interact. This can be exacerbated if they are a recent graduate who hasn’t experienced the workplace before. It can instill in people a fear of asking questions. It is important across our industry that we make it known that people can fail and ask for help.

For those of us that are more experienced, when you see a project taking longer than expected, reach out and ask if the person working on it needs assistance. I was shocked when I learned that my team member needed help and had been struggling. I’m hopeful that our conversation made them feel more comfortable asking for help in the future, and I’m hopeful that I’m teaching my students that it is important to ask for help and that they should never feel ashamed to do so. I can’t say for certain I’ll be successful, but it is important that I keep trying.

Do you know ways to help people feel more comfortable asking questions or to suggest that they should ask for help when they need it? If so, let me know on Twitter, because I could use all the help I can get.


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Back to School – Lessons From Teaching Cybersecurity: Week 1

Developing Confidence – Lessons From Teaching Cybersecurity: Week 2