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Welcome to my blog. I talk about all things tech & leadership.

How to Get by Giving

How to Get by Giving

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One of the annual events that I get to participate in as part of VMUG is the VMUG Leader Summit, held in Palo Alto on the VMware corporate campus. It’s an awesome event that has become an annual gathering of about 140 VMUG Leaders from all over the world. We get together to learn what’s new and forthcoming from VMware, share best practices for leading our local groups, and make friends and connections across six continents. I’d prefer it be 7, so if anyone from Antarctica is reading this, please sign up to be a VMUG Leader!

Anyways, last year and this year, I’ve honored to emcee this event as VMUG President and it always gets me to thinking about how my career has grown right alongside my involvement in VMUG. If we haven’t met before, you may not have heard this story so I’ll put it out here really fast:

When I joined VMUG as a member back in the mid-aughts, I was a systems administrator with a focus on Microsoft Active Directory, Exchange, and assorted technologies. I had a small group that I worked with and was the most junior person on the team – by something like ten years. I joined VMUG because I wanted to learn more about VMware technologies and no one in my office knew what they were, so I couldn’t learn from them. In fairness to them, ESX was still relatively underground so it wasn’t really their fault. The more I learned at the VMUGs I was attending, the more valuable stuff I could do in the office which ultimately got me promoted to a Systems Engineer job.

Not too long later, I had the opportunity to become a VMUG leader in 2011. This new volunteer role made me exercise my organizational skills as I served the IT community in and around the Boston area. While I was mostly focused on how to bring great content to the local area that folks like me wanted to see, I didn’t realize that I was also starting to learn a bunch of new skills.

I learned to manage sponsors, venues, and timelines better than I ever thought I could up until that point. The hardest for me (as an IT Pro) was negotiating with sponsors to get funding for our events because it was so far away from my day to day job role. But learning those negotiation skills and how to articulate a value proposition helped me in the office as I lobbied for (or against) certain projects or products.

As a direct result of that skill-building, I started to lead more projects in the office and was promoted to a team leader role. I firmly and honestly believe that if I didn’t have the experience of running projects outside of the office I wouldn’t have been promoted into that next role, because I wouldn’t have had the required skills to be successful.

Another part of being a leader is that I was “required” to speak in front of groups with some moderate frequency. I put that in quotes because if you’ve ever talked to a bunch of VMUG Leaders, it actually isn’t a requirement to be a leader. There are a ton of VMUGs where one leader likes to speak and does so, and another (or others) would rather hop a one way ticket to the moon and so serve their local communities in other really valuable ways like sponsorship coordination, running event check-in, getting other people to speak, etc. However, I was the lone leader in Boston for a while and so I ended up speaking out of necessity. I’m not a natural speaker by any stretch, but I quickly got comfortable in front of an audience. Again, my goal here was simply to provide a great event and fill some time between presentations and lead group discussions as a moderator. I was really excited that I was able to help so many people like me learn new skills and make connections. Meanwhile, I was learning new presentation skills without realizing it.

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By being comfortable in front of an audience (that isn’t afraid to heckle you) at a UserCon, I was able to be a lot more comfortable presenting ideas, status updates, and other knowledge to larger and larger groups with more and more senior leadership present while I was in the office. I was able to fully articulate ideas in concise ways with some slick visuals to get the point and promise of an idea across. I’m pretty sure that’s a major reason why I was promoted to an associate director where it was officially my job to run the operations and manage the systems engineers and administrators.

I think one of the themes that keeps popping up here is that I was growing my skills in a volunteer role which would precede a promotion. I suppose we should dive into that just a bit. I’ve found time and time again in my career that if I wanted to learn something, it was often the case that the safest and most convenient way to do so was by volunteering and didn’t come from my day job. Virtually all skill acquisition - or at least practicing a new skill - involves some risk. Let’s be honest - it’s possible that when you’re trying something new you could be really, really bad at it.

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You want an example? Sure thing: I’m reminded of the first time I tried to ski jump – and not only wiped out, but almost took out half the crowd with me. I remember thinking as I slid down the hill flat on my back - completely unable to inhale and not sure my leg was still attached - that I hope I didn’t kill anyone.

Oh, you wanted one focused on technology? Got you covered there, too: The first time I tried to deploy software using Group Policy, I forced everyone to wait for 45 minutes at logon while Office installed. I caused a huge number of enraged calls to come in. So, wanting to stop the bleeding, I disabled the policy, which immediately started uninstalling the software from everyone’s computers. You can probably imagine that the angry calls got more frequent… and more intense. I was bad at group policy.

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When you have to practice a skill at the job that pays your bills in front of people that decide if you get a promotion, bonus, or any sort of incentive-based compensation, you run the risk that a poor performance may impact people’s perception of you or your abilities – even if it’s unwarranted. As unfortunate as that is, it’s generally how things work – if you do poorly, it takes a while to change perception and get a second shot at it. So while there may be some excellent rewards as incentives to do well, the downside risk is very real in my experience.

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In contrast, every time I’ve done something for the first time at a VMUG or other community event, I have felt nothing but supported and encouraged – even when I do poorly or things go sideways. I can still remember one time at a large UserCon with two hundred people in the room, and I was trying to do a virtualization skills challenge. I called it “Competitive Systems Administration.” It was like dueling live demos, which is (as you can imagine) riskier than a single live demo. The demo gods were not with us, and it went sideways quickly, and the whole thing fell apart. It failed. There was no graceful recovery – we had to effectively flip a coin to pick a winner. Afterward, I had a good number of people come up to me to tell me it was a great idea and they couldn’t wait to see it again. Not a single person – not one – said that it was bad. No one. When I talk about the community being a safe place to fail, this is what I’m talking about.

About this time, my involvement in the VMUG organization was increasing and I had more access to (and interest in) the overall operations of VMUG. I was excited and energized to be a part of something big and an important part of people’s career development. It felt great to help an organization that I care very deeply about continue to grow and serve even more people around the world. Ultimately, I was nominated for and accepted a position on the VMUG Board of Directors in 2017. In this role, I work with a team of people committed to VMUG’s success but that don’t always have the same vision for what that success entails. Working with a diverse team to gain consensus was a new skill for me to work on, and I loved doing it – because we were (and are) building something for everyone: a place where everyone can grow together. I feel very confident that it was predominately because of this growth that I got to do as a part of my volunteer involvement with VMUG that I was promoted to Associate CIO, with overall responsibility for compute infrastructure and service operations.

I guess what this all boils down to is this: if you feel like you aren’t getting enough opportunities to grow in your day job – then go find a volunteer gig that will give you those opportunities. The world is awash with a need for volunteers. There is an organization out there that needs you. And even better – there is an organization out there that needs you that caters to something you care about. I know I’ve been talking about VMUG and the tech community here, but I also volunteer doing financial literacy in my community – and that has also built up a bunch of skills that have been valuable for me in the office. Not all experience is experience gained in the office, and I firmly believe that people who only have “office experiences” probably don’t have enough experience to make them well-rounded leaders with good perspective.

If you are one of the hundreds of VMUG leaders around the world, thank you for what you do for our communities. More broadly, if you are volunteering in any capacity – thank you for dedicating your time and talents to make the world more like you want it to be. If you are not volunteering, I want you to consider it. While I love giving my time because it makes me feel like I’m contributing to the greater good in some small way, it’s also OK if you volunteer because you want to grow and learn new skills. In the end, selfishly motivated volunteering is still volunteering, and you’re still making an impact – even if you get something out of it.

I know I have. And I’m grateful for it.

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Some challenges and questions for you:

  1. Are you volunteering? Have you gotten any benefits out of doing so?

  2. If you aren’t, what’s something that you can do in the next 14 days to give back somewhere?

  3. Can I help connect you with some opportunities in VMUG? I can’t help if you want to volunteer at the humane society, but I know a lot of people who’d love to chat if you want to spend time helping VMUG members.

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