Mentorship and Squandered Opportunities

Do you have someone in your life who mentors you personally or professionally?

I spent the greater part of 3+ decades looking for mentors. I wasn’t a great student even through college, but I did recognize fairly early on that it made sense to get mentors. I knew that a good mentor would serve better than a professor, as the mentor would tailor the advice to my own experiences, and not speak generally and overly academically to a nameless student. I knew that a good mentor already had a map for where I could go, and would be able to provide specific feedback for what to do more or less of.

Like a lot of things in my life pre-internet, though, I didn’t even have the vocabulary or community to be able to know how to ask about what I was looking for.

Once I started using the internet, I found work, and with work, I found employers and friends who were unorthodox enough to have identified the internet as being useful, and who were willing to take a chance on a college kid to do the work since it was a limited job market at the time.

So, by the time I joined the Army, which had long-ago established a formalized vocabulary and process for long-term training and mentorship, I had some other people in my life who would look out for my long-term career, and who would keep me on the straight path, and who cared about me as a person long after I stopped working with them.

Eventually I moved into software development in the 2000s, which still did not have a great environment for mentorship unless you worked at large organizations. Hero, 100x, unicorn coders who were assholes but brilliant at coding were what everyone wanted to find. They would get promoted to management by virtue of being brilliant, even if they were toxic.

At my current employer, I advanced to become a manager of managers. For me, without the plethora of information now being posted online and published in books and released as podcasts for new managers, I’d be far less effective at my job and would be employing barbaric management methods that led to the pointy-haired boss stereotypes of the did-not-age-well Scott Adams.

Where did all this excellent management guidance come from? Well, the larger and newer tech companies like Facebook, Etsy, and Google have raised scores of veteran managers who have had to apply traditional management structures to agile methodology and startup pace. These veterans immediately realized the benefit of sharing on the internet and they quickly published what they already knew was a nascent skill in the industry: how to develop software engineering teams into force multipliers.

Rituals are now built in to expectations for software developers: weekly or fortnightly 1-on-1s, career paths, investment in coaching and team management training, etc. Instead of hiring coding savants and letting them do whatever for half a year between check-ins, a close touch and high-empathy/communication is a requirement for promotion.

So, that’s where we are today. If your organization ISN’T like this, it’s going to be lagging behind.

With all that in mind, why is it then that people continue to neglect opportunities to be mentored?

Here are some (but not all) potential reasons:

  • People don’t think they need the help.
  • People don’t know what having a great mentor is like.
  • People are afraid to ask, even when given permission.

People Don’t Think They Need the Help

If this is true, then it could be interpreted in several ways. The job market for engineers is frothy; there’s almost no friction (besides horrible interview processes) for moving from one coding role to another for most people. In many cases it’s the best way to get a promotion or get more money. So people almost never feel the pressure to find a different job, and so why would they ask for extra help?

Another interpretation is that people just think they know all they need to know already. This seems scary to me. Say you’re a decent coder; wouldn’t you want to reach out to others for guidance and help? How do you know what you don’t know unless you research and talk to people? In fact I might go so far as to want to ask someone if they do have any good mentors, because it might indicate if they sought help, and/or if anyone wanted to help them.

People Don’t Know What Having a Great Mentor Feels Like

Mentorship is super hard. For an introvert, it’s one of the most draining things you could do. You have to be engaged, sensitive, and able to produce results if someone is reaching out to you. This isn’t like coaching, where you provide ideas or methodologies that are ultimately on that person to implement and succeed at; mentoring in many cases is opening doors for people and there’s a stronger sense of delivering a win.

A lot of things have to go right for a mentor to resonate with a mentee. They have to have chemistry between each other. The mentor has to be empathetic, and have the respect of their mentee. They have to roughly agree on the perspective and potential options.

So, most people who could potentially be mentors have never been put in a position to work that muscle. As a result, you have mentor relationships which are almost always dictated by power: a more senior ranking person is mentoring a more junior person. Do you have mentors who you’ve never even worked for?

Now, just imagine you knew the market for mentors/mentees better. You had more narratives to read that showed how a relationship like that positively impacted someone’s life. Wouldn’t you take it more seriously as a career path requirement? Wouldn’t you want more people helping you succeed?

As a related example, my employer paid for me to get professional coaching. I was skeptical at first, likening it to therapy (not a new concept in the northeast). But it was transformative. Imagine someone listening to you speak about difficult situations at work and how you can understand what you’re thinking and feeling, and then combine actionable solutions with your own personality. It was a massively enabling experience to me, and it allowed me to figure out how to map what I want with what I’m doing.

I just can’t see that once you’ve worked with a great team or mentor, that you’d ever want to put yourself in a position where you didn’t have that anymore, if you had a choice.

People are Afraid to Ask, Even When Given Permission

If someone says to you, “Hey, reach out to me if you ever need anything,” that’s an open invitation to do so.

The way to frame this is that it is your professional responsibility to ask for help. To stay silent is hurting yourself, for sure, but it’s also hurting those around you, because they’re not receiving the best potential version of you.

So, stop with using this as an excuse. Each of us needs all the help we can get to succeed, and even if it’s against every one of your impulses, you need to reach out to other people.

A Community of Support

I had mentors when I was a web designer in the 90s and mentors when I first started software development in NYC. I didn’t have mentors when I lived in DC doing security/policy or when I was in the Army, but those worlds also had their own strict frameworks that pretty much provided a (less specific) mental map for me to set a direction and head for it. Ultimately I realized their destinations where not where I wanted to go.

I wouldn’t have gotten to where I am without mentors, and I always knew (and still remind myself daily) that I would need mentors to help me become a better person. Don’t make the mistake of thinking you don’t.