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9 Career Lessons from a Veteran CIO

As fall sets in and summer winds down to an end I am back in GRIND mode–as if I ever stopped–but you get what I mean. Fall season is typically my busy season for a lot of reasons–our 50 Wards 50 Meals Thanksgiving Food Drive & Fundraiser, end-of-year planning, etc.–but since summer is now gone I’m back to doing what I do a lot of–networking. I talk to people day-in, and day-out and I have some great lessons I want to share from a conversation I had over the weekend with a veteran career CIO (Chief Information Officer)

CIO’s are the top Technology Executives within the Corporate Enterprise. They have overall responsibility for an organizations IT budget–P&L, implementation of Technology projects, Technology strategy, and the use and management of Information and Computer systems.

I had the opportunity to connect with a gentleman who is a career IT executive here in the Chicago area and discuss a variety of topics around Tech and Career lessons in Tech. He has been in the IT field for well over 30 years, many of those years as CIO for several organizations including a few Universities, and he currently consults for a very well known consulting firm in the IT industry.

His niche specialty is working with senior IT Executives, mostly CIO’s and CTO’s (Chief Technology Officers), where he works mostly with senior leadership across the private and public sector, large Fortune 500 companies, and even CIO’s for some State’s where he consults and guides IT leaders on how best to execute their organizations IT strategies and objectives.

I met him last year at a party and at the time I didn’t realize the breadth of his experience until we had a chance to speak recently on LinkedIn. I mentioned to him that I was looking to expand my network with well seasoned and accomplished IT professionals–CIO and CTO alike–and perhaps gain a mentor or two and I asked if he would be willing to meet me.

He said, “Yes! Absolutely… I would love to help.”

We messaged on LinkedIn that evening to set something up, he asked for a copy of my resume, and on Saturday morning we met for breakfast and a conversation that, unbeknownst to me, would really turn the tide on a lot of the ideals and perspectives I had on what it means to succeed in IT.

Here are 9 lessons from that 2-hour CIO conversation

This lesson rings true for a lot of reasons because often times we are really good at telling people what we’ve DONE but not so great at articulating HOW what we’ve done has made an IMPACT. The keyword I recall him using is “value impact”. Questions like, “How was the organization positively impacted by what you did? ROI, saved man hours, cost savings, etc.”

There are lessons, life lessons, that aren’t talked about when we think about the context of working in Corporate America. I think personal development, your faith, and your beliefs come into play here because when you think about it, how well do you navigate challenges when dealing with people you work with? He told the story of a time when he was assigned to a project over others in his department at a particular company where he worked. In the beginning it was difficult for him to get anything done. He labored and eventually got the project completed all the while doing a great job, but would later come to learn that some of his colleagues had intentionally decided in the beginning that they were determined NOT to help him. In other words, sabotage. How well do you deal with and manage people? This is key to your success and difficult to do.

Today, a lot of companies use HR and Career and Human Capital Management platforms such as WorkDay to help organizations plan and map Corporate goals. Most CIO’s understand that they have to set goals and get their team to set reasonable and measurable goals. Understanding how the work that YOU do impacts the overall Corporate goals of an organization is very important. If the company that you work for does not do this, having a conversation with your manager to understand their goals is the next best thing. Understanding these goals allows you to tailor your activities to that of the organization or your manager.

This was a lesson that he and I talked about at length and at the end of the day what matters is this: How well do you manage conflict resolution? CIO’s understand that in leadership positions you’re often times going to have to lead and in leading it means that YOU have to be responsible for the outcomes or the lack of outcomes that come from the people you lead.

This is something that goes along the lines of personal development in dealing with and managing people. Instead of looking at conflict with colleagues as a bad thing you think of this as a growth opportunity. You can also look at bad situations in the workplace as opportunities for you to show leadership. Do you take a positive and constructive view of things and look for ways to turn those moments into something positive, or do you fold and stop searching for the constructive side of things? CIO’s know they have to master this as do all leaders.

This piggybacks off of the first lesson above but he talked about something called “value impact” a lot in our conversation. I myself can’t say that I’ve always consciously thought about the direct impacts that my work has on an organization, simply because we get hired to do a job, we do what we were hired to do, and thats it. This way of thinking however requires that you take more time to think deeply about your role and the work you do. Which is why having mentors that you can talk like my CIO friend are really great assets. Other seasoned leaders can typically help you see the blind spots that we don’t normally pay attention to. Pay attention to the value of your work and how it moves the needle forward in your organization.

I think we’ve all heard a time or two that you should always be volunteering and raising your hand to take on new work and projects. This tends to be very true especially in companies where a lot of people are there only to do the minimum amount of work. The path for this CIO entailed taking on a lot of projects that he probably didn’t want to take on, but he did it so he could stand out. Keep yourself OPEN for new opportunities as they come and as you do others will take notice and come to rely on the fact that they can depend on you to get things done.

From a leadership perspective this is probably the most IMPORTANT thing you can understand when in a leadership role. As CIO your job as a leader is to get things done through direct influence of others. The other critical factor here is TRUST. When you trust your teammates to accomplish certain things it strengthens your relationship with them. No leader can do everything by themselves so they must learn to trust those that are entrusted to them to lead. The more effectively and efficiently you can delegate and trust your team to execute the more you can get done.

They say if you are the smartest person in the room you’re in the wrong room and I think this rings true no matter what level you’re at in life, even if you’re a CIO! Strong leaders understand what it means to have knowledgable people around them. If you’re a leader and you’re intimidated by someone who is sharper than you, you can’t and won’t be able to lead them. Your team should never be your competition, but they should be the ones that you empower and support to reach common goals

As someone who is prior military I resonate with this very well. In fact, this is probably one of those areas where most people struggle the most. It’s always difficult and challenging to be assertive about your career goals. There is always someone telling you that you’re not good enough, you’re not qualified, constant and continuous rejection, and on and on. When I was in the military there really wasn’t a vetting period to determine if I was qualified to do something, most times I was just assigned to do it and that was it. In the civilian world it’s quite different. To be successful here you have to essentially OWN your own career path and dictate where you go and what you do despite what others may think. Sometimes you just have to tell yourself and the world what the deal is and walk right pass anyone in life that tells you otherwise. You have to be that BOLD and that CRAZY to believe that you are capable of creating and doing what you envision with your career. CIO’s know this. That’s why they’re leaders.

See my VLOG on my YouTube channel on Lessons from a CIO

Read this blog post: Technology Apprenticeship Programs Are Helping Single Moms, Vets, Everyone

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