Saturday, December 12, 2015

Retrospective: 2015 as a Tech and Career Mentor

2015 was a pretty great year mentoring for me. After several years of offering advice to others, I now have a small, consistent group of individuals that I work with. Each in a different way, important to them, but probably more important to me.

My Background and Thoughts On Mentoring

I generally mentor people at Microsoft who are experiencing some issue in their career growth. Sometimes the issues are things they can change, sometimes the environment needs to change, sometimes it is technical, sometimes it relates to missing skill-sets and sometimes its personal issues. No matter what the cause, as an external observer, I can either directly help them or I can find someone else who can. I can be supportive, uplifting or give them the hard talk about something they need to change. Whatever they need. As a mentor I'm adaptable to their situation.

Most of my mentoring sessions consist of drawing parallels between road-blocks that I've faced and how I overcame them. By explaining through a real scenario it usually becomes much clearer to others that they have options. More increasingly though I find that my experiences aren't the same as theirs. This was a great mentoring realization for me, people have unique problems, they have unique strengths and weaknesses. My "solution" isn't their "solution". Instead I need to offer many viewpoints and using the combined experiences of all of my mentees, not just my own experiences. Intelligent people tend to solve their own problems once they start to realize how many options they have. Persistent problems tend to remain so long as your options are limited.

Helping someone find their options isn't limited to those with wisdom and experience either. This is my pitch to those who think they are too young mentor others. Mentoring is just as much about listening, learning, problem solving and being supportive as it is about learning purely from experience. If you are giving someone the solutions to their problems, it isn't really a mentoring session anymore. You are trying to make them better, help them to find their own solutions, not demonstrate how easily and intelligently you could resolve their issue.

Mentoring doesn't have to be formal. It could be one friend to another. It doesn't have to be long or short. A single meeting or many years worth of them, both outcomes are acceptable. It could be a regular weekly meeting or it could be a couple of random days in the year. It doesn't have to be scheduled at all, for instance, getting feedback on a potentially career limiting email from your mentor can often be the difference between success and failure.

We need more mentors thinking about diversity. Rico Mariani recently started an inspiring series of thoughts and threads (well more than that, he started a scholarship) focused on women in tech. He immediately reached out to everyone on his team and made it very clear, minorities in tech, regardless of which minority, need equal opportunities and access to strong mentors. So I'm going to do some more thinking on this. I think it is very hard for someone to reach out and accept mentoring and the bigger the differences which exist (level, race, gender, social status, personalities) the harder it is for someone to take that first step. Its probably time to reach out to potential mentees, a lot more often, and accept the rejections in favor of helping the diversity imbalances.

My Mentees for 2015

This won't focus solely on 2015, since one of my most important roles in mentoring occurred during 2014 just following the large Microsoft lay-offs. My list of mentees (anonymous) and how we spend our time.

  1. The Entrepreneur - I once owned my own company and was independently successful for a few years during my 20's. This experience taught me quite a bit. One of my mentees is at a point in his life where he wants to develop a small company for himself and so we have sessions on how to transition from your day job to being a founder.
  2. The Classic - Before the Microsoft mentoring site went down I got my last mentee referral for what would become my most normal mentoring setup. We meet on his schedule and the topics are around how to manage his career development, communications, timing and positioning. Sorry, I'll expand more on that in a bit ;-)
  3. The Switcher - Within the past few months I've started working with someone who is unhappy in their position on their current team. They had already made a decision that improving their situation was not the right move, that they needed a change. For this person, I'm helping them improve their technical interviewing skills.
  4. The LayOffs - When the large scale Microsoft lay-offs happened I realized quickly that many intelligent and capable people were going to start having a very hard time in the job market. It is easy to have your skills atrophy when you work in a mature company like Microsoft. For this group, I got to learn the challenges of mentoring in a group setting.
  5. The Boxer - Everyone needs change and growth opportunities. This person had been working in the same area for too long and was feeling constrained, as if they had been put in a box for safe keeping. When in this position, having options and knowing what you can and should be able to ask for to improve your situation is key.
With the exception of the group training I did when the lay-offs occurred, my diversity scorecard has me gender biased (zero female mentees) but doing okay otherwise (I have mentees of many races, though they are all male). During the lay-offs, I was able to help multiple female engineers reset their skills and I'm happy that a majority of them were able to quickly find a position that was as good or better than what they left.

You Get More than you Give

My mentees are consistently conscious of my time. They don't want to waste it, since they view my time as important, and they view me as someone who maximizes the value of my own time. Guess what, they are right! I do value my own time and I can say hands down the time I spend mentoring is far more important than anything else I could be doing. So the secret to mentoring is that you spend time doing it, its that you can help yourself and others at the same time, in ways that will help you in the future.

After all, how do you become better at anything? You PRACTICE it. Mentoring gives you the opportunity to be a great listener and a strong communicator. It helps you to organize your experiences and arguments through self-reflection that you are able to share with someone else. Your mentee can sometimes reverse the experience on you and potentially point out something you missed when you dealt with a situation that you are using as an example. These moments, for me, have always led to improvements in my own career.

Your mentees will also have experiences that differ from your own. This will help you increase your own understanding of diversity and help provide you with insights to improve how you integrate and communicate with your co-workers. Perhaps a certain cultural bias prevents someone from speaking up, and you are able to experience this through your mentee, then it can make you more sensitive to this issue.

The last bit for me is around building your moral standards. If I'm not helping people, I'm not happy. There is a certain amount of human interaction and empathy that goes into the entire process that leaves me feeling like I've done something, bigger than myself. I've reached out and helped someone else. You can get this many ways, through teaching, mentoring or volunteering, so I challenge you to do all 3 to maximize your own benefits ;-)

Reaching Out

You've read everything above and you are thinking, "Sign me up!" So how do you start? I don't have 40 years of experience doing this, but I do have enough to know one thing. Not everyone realizes they need a mentor and pointing it out often isn't enough to convince them. Mentoring is a two-way street and even though I have time to give my advice it doesn't mean that others have the time to hear it. It is an exceptional case when someone walks up to you and ASKS you to mentor them. This almost never happens. 

So you have to put yourself out there and let people know you are ready to help. When approaching a new mentee with an offer, do so privately. Not everyone sees having mentors as a strength and some see it as a sign of weakness. A powerful mentor relationship can also be seen as a threat or even favoritism. This is normally irrational and unhealthy thoughts by others but it is something to be aware of.

By the numbers, the amount of people that I will approach is quite small. I'm evaluating a lot of different outcomes and consequences. As a mentor I should do a MUCH better job of approaching people. 

Once approached, the acceptance rate is probably 50/50. So be prepared to be rejected. This is key, never take someone else's rejection of your mentoring offer as anything against you. There are a lot of factors they are evaluating as well, including whether or not they even feel comfortable talking to you. They may not see you as a mentor at all. This is normal. When you get a rejection, kindly let them know that you are available in the future if things change, and move on.

Even out of those who accept, there is a likelihood you will never have your first mentoring session. If you do, there is a high likelihood it will be your last or next to last. Being mentored is not for everyone and maybe the session made them feel awkward. I bet psychologists have a similar track record with new clients. Also, not every problem is one to be fixed. Your mentee may find that it isn't the right time for them to think about and correct the issues impacting them. This is especially true in long term career mentoring.

Once you've gotten started be prepared to adapt yourself to many different types of people and expectations. If they want you to set up a schedule and manage it, then do that. Otherwise, if they want to set it up instead, then let them do that. The majority of the improvement they make will be when they are not interacting directly with you, so figure out how to follow up with them. If they like goals, set them up. The more you mentor the more you'll figure this out, but being prepared will hopefully your first few mentoring encounters much more fruitful.

If in doubt, get a mentor yourself and ask them about mentoring. Its the ultimate mentoring meta ;-)


Diversifying your mentees can be extremely difficult. First, people are more comfortable around those more like them. For this reason, in a work environment, people of similar ethnic backgrounds are likely to stick together. When a team has good diversity this doesn't happen as much, but then the team itself can stick together and becomes a blocker for technical diversity. Since minorities, by definition, are fewer within the groups, trying to find a mentor that matches your minority can be hard.

This leaves our minority populations in tech with a hard problem. First, they can't find high level mentors within their own minority. Second, they may find it hard or challenging to find high level mentors at all. This all assumes that they reach out. If they don't then its perhaps more unlikely that an appropriate mentor would not find them.

This type of diversity bias is what we have to overcome. It isn't really fixed by taking a "fair" approach to the problem. You can't sit back, and expect the odds to play themselves out here. While you may think that by accepting anyone and everyone you'll achieve diversity, you won't. You have to break the "fairness" and make a point of being unfair in your selection of mentees and how you reach out. Make a point of prioritizing for ethnic and gender diversity when you fill up your time initially and then worry about filling out the majority slots later. Trust me, they won't be nearly as hard to fill.

For my part, I'm going to commit to filling out my diversity card in the upcoming year of 2016. I've already tweeted that I have some mentoring capacity. I'm reserving that space for women and other minorities in tech. I will be proactive and start reaching out to potential mentees and work with other mentors in my network in case they know of people actively looking. I am going to increase my efforts towards STEM education for minorities though I don't yet have a plan for how I'm going to do that. If anyone has ideas let me know ;-) I'll make sure to be more vocal about my efforts as well in case it can inspire or inform others. Bringing awareness is a key step in solving any problem.

Finally a challenge to all you would be mentors. If you aren't sure, and you want to talk to someone about becoming a mentor, I hear you can call anyone on this thing called the Internet. I'd be happy to talk with you about my experiences and answer any questions you might have before you get started.

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