Mentors can be great. But sometimes experience is the best teacher. Five CIOs talk about leadership lessons they learned the hard way — on the job.

1. How to let go.

"I learned this very early in my management career. I had moved from the technical side into management. I was trying to hang on to all my tech knowledge and yet do all the management things at the same time. It wasn't good for me or the people I was managing. It wasn't letting either of us develop. The art of delegation is very valuable, and it is an art. It involves not just assessing who's good at Unix or XML but knowing how and when to delegate."
— Cindy Hughes, CIO, Maryland Automobile Insurance Fund

2. It's who you know, not what you know.

"When I first became CIO 14 or 15 years ago, I don't think I truly understood the power of relationships. I've seen decisions made based not on financial return or best alignment strategy but on the strength of a relationship between two parties. It's easy as CIO to say, 'Here's the internal rate of return on this project,' yet not understand that the business unit president has a strong relationship with someone outside your IT organization and wants to do software as a service rather than a new ERP system. You need to cultivate relationships over time. It's hard and I take pride in it now but I didn't realize it then."
— Craig Cuyar, SVP and CIO, Realogy

3. How to keep lines of communication open.

"I was promoted to CIO in July 2005, from director of applications. The one thing I wish I had known going in was the amount of effort it takes to maintain relationships with the other executives. I've had to really work and plan to meet with executives one-on-one and find a way to sensitize them to having their ears out for issues that might be coming that call for IT. That's as well as being on top of it myself. It takes special effort to get other executives focused on knowing that I'm approachable and I'll always be approaching them for intelligence."
— Michael Abbene, VP and CIO, Arch Coal

4. You can't satisfy everyone.

"Your job isn't to do what everybody wants. Every request you get isn't necessarily a good request. When you first become a CIO, you're reluctant to make those types of decisions. But after awhile, you realize that without making those decisions — and sometimes being fairly blunt — you're painting yourself into a corner. As a CIO, I am a service provider, but I do have a strong opinion on what services [the organization] should be asking me to provide."
— George Chappelle, chief supply chain officer and former CIO, Sara Lee Foods

5. All politics is local.

"I wish that mentors would have educated me more about other people and their motivations. At a lower level, you're really shielded from political things in an organization. You understand that they happen, but it's very different when you're there."
— Twila Day, VP and CIO, Sysco