Thoughts on Mentoring (Part II)
Welcome back for Part II of my thoughts on mentoring. This week, I’m going to spend a little bit of time with something that I have not been good at: finding a mentor. As I mentioned last week, I have not had a long-term consistent mentor, though I have had different people I can ask for advice at various points in my career. So while in a lot of ways, I’m offering some amount of advice that I myself have not benefitted from, I’d like to distill a few things that I’ve read recently on mentoring (which hopefully we can both use).
For a lot of kids, the anxiety over rejection can start when they try to find a seat at lunch.
I figured out a hack for this when I was little: just tell the teacher you’re lonely and don’t have anywhere to sit. They’ll yell out to everyone that you have no friends and need one. After that, popularity and you will be inseparable. Or, you’ll spend a lot of lunches in the nurse’s office. Same thing, right?
One of the things that I’ve noticed in my reading recently is that almost every article on starting a mentoring relationship leaves it to the potential mentee to find someone to mentor them - and then leaves the incredibly daunting task of actually asking to be mentored to the mentee. To me, this feels a lot like a proposal but without the benefit of having spent a lot of time with someone first. Even now, I can feel the fear of rejection in every bone I have just thinking about asking someone I do not already have a strong relationship with to coach me. It feels like a tall ask, and my guess is that for an industry rife with introverts this may be a bridge too far. Honestly, I can’t think of many folks I know who are comfortable with Python that are also comfortable asking someone to help support their career in explicit terms.
So how do we work to overcome this? There are a few platforms out there that attempt to connect mentors and mentees, but in my brief investigation none of them are incredibly mature or focused on a particular industry. I think industry matters quite a lot when it comes to mentoring; for example, I think having a regional director of a commercial bank mentoring an AWS architect can be a tough connection. Heck, I think it can be tough to have someone very senior within an application development function to mentor a junior engineer responsible for network QoS performance – there’s just a lot to translate there that might get in the way. The point is that these platforms seem to be less focused on getting someone who can help you with the “apprenticeship” component we discussed last week, and more with the “how to present to executives” component. The problem is that while this is indeed an important skill, it may be quite a lot less valuable than the apprenticeship aspect for many techies (at least early in their careers) who are looking to hone their skills and overall career.
It seems that there is a definite need for more programs – rather than platforms - that work to connect potential mentors to mentees. One of the things that I had high hopes for was a mentoring program that we had tried to build at VMUG. We found some people who were likely to have a fair amount of wisdom in their field - thought leaders, those in a position of leadership in their company, senior technologists, or other positions that someone more junior in their career would aspire to get to - and added them as mentors. We then opened up the program to have mentees join and tried to match people with similar interests (ala eHarmony: Career Edition). Sadly, the program didn’t get the traction it deserved - and last I checked, it was shelved indefinitely due to low participation. It doesn’t mean that in another time this sort of program isn’t needed, wanted, or couldn’t take off with better strategies to get people involved.
I intend to go much deeper into what potential mentors can do next week, but I think it’s important to address that potential mentors can be a part of making this less stressful. While I don’t have a grand plan to solve this problem, I think one of the things those of us in more senior or leadership positions can do is to keep a watchful eye open for those people in our organizations who are actively working to continually grow in their career paths and offer to mentor them. Certainly, while I would view it as an incredible compliment to be asked to mentor someone who actually wants to hear my advice, by putting it out there that we are open to being mentors we are opening the door for a potential mentee to pursue a mentorship with at least some confidence it could happen. That at least should reduce the fear of rejection somewhat, because at least a potential mentee would know that you are theoretically interested in serving in that capacity.
Pictured: Everything I know about Tinder.
When I was a kid, you had to get dates the old fashioned way: by having girls laugh in your face, or make disgusted faces at you. No? Just me? Okay.
LinkedIn currently offers a way for folks to indicate that they are “open to work” or that they are hiring. I think it would be beneficial if they did something similar for mentoring, because that’s a low-impact way for people to know you’re open to it. However, that does open yourself up to exposing a bit of potentially sensitive information, and so it might be even more effective if it was done like Tinder for Mentoring. Having never used Tinder (I got married five years before Tinder launched), I think I’ve gathered that it works by connecting people who have expressed a mutual interest in each other. I actually like this model, because it could reduce the anxiety needed to blindly see if someone is interested; if you’re allowed to connect then they’ve already indicated some level of willingness to do so. Turning back to our mentoring problem, imagine if you could check off that you would be interested in being mentored by someone - but they would only see it if they had also checked off that they were interested in mentoring you. If you get a match, you have a low-risk way of starting that relationship up. I am copyrighting this idea right now. (No, seriously… can we actually do this?)
Barring a revolutionary app that can help you match with a mentor, what should you do if you are seeking one out? Well, assuming that those who are willing to mentor others may not always be aware of those seeking them out, my suggestion is that you spend some time thinking through people you know who have some knowledge or skill that you’d like to emulate or start to develop yourself. Then, see if you can offer to buy them lunch or a coffee to tap their brains about their expertise. If they say “no,” that’s a pretty big indication that they don’t want to build a mentor/mentee relationship with you. I’m sure there have been untold pages written about persistence, but this is not one of those. I would see if you can find someone else with similar skills or traits who might be more likely to be open to a mentorship arrangement. However, in the far more likely event they agree (after all, who doesn’t like a free lunch or coffee), open with shameless flattery. Tell them that you admire how well that they do [whatever they do that gave you the idea to ask them], and that you’d like to try to get better at [that thing]. Ask how they built their skillset and what you could do to further grow yours.
C’mon, who wouldn’t want to get coffee at this place? Hey, you could ask me to mentor you in your Tinder use, and I’d accept if it meant spending an hour here. The advice would be worthless, but I’d get a scone out of it.
And don’t sell your own skills short; while you’re in this meeting, ask if there’s any way that you can help your mentor too. At its best, a mentoring conversation is a two-way street, it’s not simply listening to the wise old professor regale you with the secrets to worldly success. It’s a conversation that you should both walk away from having experienced growth. You’d be surprised how many middle-aged executives would love if someone would show them how to protect their family’s privacy online better or help them understand the subtext to the Slack conversations happening in the office every day. While it’s not exactly a tit-for-tat conversation, you certainly need to make sure that you aren’t presenting yourself as someone who’s just looking to take whatever you can from the relationship without pouring into it a little bit. If it goes well and you hit it off in this initial meeting, ask for a follow-up meeting in the not-too-distant future, specifically to check in on some of the tasks or action items that you walked away with. I know for me, that if I don’t have something specifically on my calendar or Todoist list as an action item, it’s likely to be overlooked.
Since I’m most familiar with the VMware ecosystem, let’s roleplay this conversation out as if someone asked me about learning how to roll out, operationalize, and support a VDI environment. If someone complimented me on how well I or my team did that and asked how they could do the same, I’d first be flattered and thank them for the kind words. Then, I’d probably ask a few questions about what aspects of the EUC architecture they already understand – after all, I want to give them something actionable. Let’s say that they have a fair knowledge of project management, but don’t know much about the VDI technology in question. (Look, for any vExperts that read this, I’m intentionally not going deep into the technology.) I would probably point them towards the VMware Hands-On Labs, as well as a VMUG UserCon in their area. Both are free, provide practical hands-on learning to grow experience and skills, and frankly are a big part of how I learned.
Notes! Not just for keeping track of the plot of Christopher Nolan movies anymore!
If you’re the person soliciting this advice, take notes, thank the person you asked, and then take what you learned back with you and apply it. After all, having a mentor isn’t worth anything if you don’t take action. It’s like reading a cookbook and then never getting the ingredients out or turning the oven on. You won’t make any progress in your career (which is the whole point of this mentoring thing) if you don’t put in the effort to apply what you learn from a potential or full-on mentor.
Now, here is the part that seems to be of critical importance: once you’ve made some meaningful progress towards whatever goals or process that your almost-mentor has set out for you, shoot them a note (email, text, whatever) to let them know how you’re doing and what your experience has been. Ask for any advice with anything that you’re stuck with. Be prepared for them to not give you the answer, but instead give you a place to find the answer. After all, it’s not their job to teach you - it’s to give you advice and coach you. If you keep this conversation up, keep following their advice, and finding value in it, you have found yourself a de facto mentor. You can call it mentoring or you can call it advice from someone you respect. You can call it whatever you want, but the bottom line is that you have taken an important step in building a network of people around you who can support you.
Something I am only just now realizing is that if you overcome your resistance and are able to reach out to ask someone to be a potential mentor, one of the skills that you would have practiced if you do this is some amount of assertiveness. You reached out to someone and asked them for some amount of support, and that takes a not-insignificant amount of courage. It’s possible that this may be one of the more important things you get out of asking someone to invest in you, perhaps even more valuable that whatever specific skill or trait you asked for coaching to develop. And don’t undervalue the growth that you would get from simply going through the process. You now have someone who has invested in you, and that is often a glue that continues to bind you over time.
Here’s the best part – you don’t have to pick only one person. Mentoring likely works best when you have more than one person coaching you in multiple areas and you’re learning about each of them from their strengths. After all, you want to plot a course for yourself, not simply turn yourself into a dollar-store version of someone else. If you know someone great at public speaking or presenting, and you want to get better at that - then ask them. Know someone else who writes awesome code? There’s nothing stopping you from asking them, too. Ask them both, practice those skills, and then somewhere down the line, go give an awesome presentation about the incredible Python you’ve weaved.
Next week I’ll talk a little bit more about what those of us in more senior roles can do to help move the needle when it comes to mentoring relationships in the IT field, and hopefully increase the supply of people willing to be asked for advice. After all, there’s certainly a need. See the results below of my second Twitter poll on mentoring.
My last poll asked about people who may or may not have had a mentor. This time, I'd like to ask a more basic question about if you would want one.
— Steve Athanas (@steveathanas) April 12, 2022
Do you think that you would like (or would have liked) to have a mentor?
Please tell me why in a reply!
The numbers here don’t lie. I know it’s a small sample size, but a full 100% of respondents said that they would like to have a mentor or that they enjoyed having one. Not a single person said they wouldn’t, or thought it was a waste of time if they had had one. Coupled with our results from last week, we can see that IT professionals overwhelmingly want a mentor, but actually having one seems to be elusive.
Questions for reflection:
Are you intimidated to asking someone for coaching or help? Why?
Can you think of someone that you admire that you can buy a coffee for this week and spend 15 minutes with? What advice would you ask them for?
What do you think you could offer a potential mentor in gratitude of what they’re helping you with?
Why would it be good to have a diverse pool of advice from different people?
