A couple of weeks back, I put together an article entitled, “7 things experienced web developers wish they knew earlier.” It was filled with great advice from long-time developers, who shared some of the most important lessons they learned over the years.

That got me thinking. What about other professions? In any job, you’re bound to know more today than you knew starting out. There must be at least one important lesson that you wish you knew earlier.

Today, I’d like to approach this topic from a CIO and IT leader perspective. If you’re an experienced CIO or IT leader, what do you know now that you wish you knew when you started your career? If you were to have a conversation with a younger version of yourself, what advice would you give?

We asked those questions to experienced CIOs and IT leaders, and received some great input. I’ve compiled their advice below, but–as always–feel free to contribute your thoughts in the comments. Here are 7 things experienced CIOs and IT leaders wish they knew earlier:



1. Understand your user’s problems

“When I first started in IT I was enamored with the technology and what new thing it could do,” explains Michael Clapperton, CIO of George Little Management. “Many ‘C Level’s’ don’t care about what the latest and greatest is, they just want to solve a business problem. Stick with the problem, then if technology can fix it then convey that in SHORT CONCISE language that they can understand.”

It’s a lesson that applies to nearly anyone: Understand your users and the problems they want to solve. For instance, if company executives ask for mobile apps, dig a little deeper before running off and building a solution. What problems are they trying to solve? What are they hoping to accomplish with a mobile app?

2. Assume the best

“Earlier in my career, I was impatient and sometimes hot headed and I did not assume that everyone’s intentions were good,” says Joe Fuller, CIO of Dominion Enterprises. “I have found later in my career that almost everyone is motivated to do the right things and when something goes wrong, it’s usually due to an unfortunate set of circumstances rather than a person’s incompetence or lack of dedication. Once I learned to assume the best in people, my relationships got better and our results got better. When people who are intelligent and dedicated don’t do well, the people in charge need to reflect on how well they are defining or not defining the mission.”

This is fantastic advice for CIOs (as well as leaders in general), and is more important than most people realize. When leaders address mistakes with judgement or anger, they inadvertently create a fear of failure among their employees. Why is that a problem? As outlined in this article, a fear of failure is the #1 creativity-killer.

3. When conflict arises, talk about it (don’t email)

On a related note, how should an IT leader or CIO deal with conflict when it inevitably arises? As Fuller explains, the answer is simple: Talk about it (but not over email). Most likely, it’s simply a misunderstanding.

“Another piece of advice I would give my earlier self is when there’s a conflict, pick up the phone or go visit the person,” explains Fuller. “I wasted too much time and positive energy crafting biting emails when there was almost always a misunderstanding or grounds for compromise that can only be discovered through a verbal exchange. Again, this mature approach comes from assuming the best in people. My rule today is that email is for positive or neutral communication only and I ask that everyone in my group follow that rule.”

4. Under-promise and over-deliver

“Whatever you do, be sure to under-promise and over-deliver,” says Frank Petersmark, a former CIO and current CIO Advocate at X by 2. “The last mistake you want to make as a new leader is promising more than you and your team can deliver – even if the pressure is on to do so while you’re sitting at the board table, or in a room full of customers. It’ll take some courage and intestinal fortitude to say ‘no,’ or at least ‘not now,’ but in the long run you’ll be building trust and credibility – things not easily regained once lost.”

I believe this is important advice, and should be followed by all IT leaders. However…be careful. While you can’t over-promise, or agree to projects that your staff can’t handle, some make the mistake of taking this too far. How so? Many IT departments fall into a “culture of no,” where they regularly deny user requests. As explained in this article, this approach often contributes to a “Shadow IT” problem.

How can you avoid this trap? Always remember the first point: Understand your user’s problems. Rather than simply saying “no”, try to understand what they’re trying to solve. You may not be able to solve it in the way they’re asking, but maybe you could suggest an alternate approach.

5. Focus more on the people and the business

“While technology is always evolving and IT paradigms shift frequently in the information age, my 22 years as a CIO has taught me that there are some core critical skills for IT leaders which remain constant,” says Brian Kelley, CIO of Portage County. “We must be technology enablers, visionaries, and we definitely must be more focused on the PEOPLE than the technology within our organizations. Focusing on people involves aligning IT with the business, delivering superior customer service and IT support to end users, working with management to decrease costs, and increase efficiencies, and successfully interfacing people with technology. If you’re just focused on technology, you are missing the mark as a CIO and IT leader in the 21st century and you may want to consider updating your resume!”

Gyutae Park, Head of IT at Money Crashers shares that sentiment: “I wish I knew that gravitating out of my comfort zone and working to bridge the gap between IT and business operations would have a much bigger effect on my success than simply solely focusing on how I ran the IT department in and of itself. It took me a long time to come to that realization.”

I couldn’t agree more. Aligning the IT department with the business is one of the most important responsibilities of CIOs and IT leaders. However, it’s not easy. What gets in the way? Here’s a list of 5 major IT/business alignment stumbling blocks, and how to avoid each one.

6. Find a trusted sounding board

As a CIO or IT leader, you’ll be hit with choices from all sides. You must choose the company’s technology direction. You must choose which products to buy. You must choose which projects to tackle. It’s not easy doing this alone.

“Find someone that you can trust and use him/her as a sounding board,” says Te Wu, an experienced IT Leader and CEO of PMOAdvisory, LLC. “Preferably, he/she can also help you “do” versus just giving advice which has little consequences. Too often as a business executive, we are bombarded with choices. All vendors are trying to pitch their solutions and services (including me), most internal colleagues have their own agenda… How many of them put your interest before theirs and how many of them can actually help you do something versus just giving advice?”

7. Treat your vendors well

Some people take the “customer is always right” mentality, and use that as an excuse to mistreat their vendors. The problem is, if the vendor wants their business bad enough, they’ll put up with it. This is a mistake. Not only is it just wrong, you could be alienating a key resource.

“Treat your vendors well,” says JJ DiGeronimo, a Technology Executive, Author, Entrepreneur & STEM Advocate. “They can help you as you help them. They often are well networked and aware of key resources that can help you in a bind, job change or new project.”

Your thoughts?

What do you think? If you’re an IT Leader or CIO, would you add anything to that list? If so, I’d love to hear it in the comments.

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