13 CIOs Share: My Big Mistakes - InformationWeek
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13 CIOs Share: My Big Mistakes

From tackling personnel problems quickly to not chasing tech fads, 13 CIO innovators share lessons learned the hard way.
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When it comes to making mistakes, CIOs like to talk about failing fast. This is the acceptable way to be wrong about an idea -- we tried something, it didn't work, but it didn't cost us a lot.

But fail-fast mistakes aren't the ones that haunt us. The ones we remember 10 years later are the strategies we followed for too long, the poor hires whom we gave too many chances, and the big vendor contracts that cost a bundle to escape.

What follows are 13 candid examples of decisions that CIOs wish they could do over. Top IT leaders shared these examples with their peers through our CIO Profile series. CIO Profile candidates are chosen because they rank highly in InformationWeek's annual innovation awards.

A few observations about these decisions CIOs would like to do over.

  • Several of these stories start with "Earlier in my career." Part of that's the reality of company politics -- don't scratch a scab that's just starting to heal. And we all prefer to put our mistakes in the "I know better now" file. But it also shows how deeply held these memories are. These were hard lessons learned, and they are not forgotten.
  • The fail-fast philosophy applies to personnel decisions, as well, since hiring mistakes rarely get better with time. We hear variations of this advice echoed often: If a person doesn't fit, take steps quickly to help that person, but if that doesn't work, it's time to make the hard call to part ways. We'll see a variation of that lesson again here.
  • Several lessons are about personal career choices. These leaders had to figure out what motivates and energizes them personally. Get that right, and even bad days at the office become a bit easier to take.

This is the fourth time we've gathered these do-over comments from top CIOs. For a look back, see our collections from 2010, 2011, and 2012. We highlight these so we can learn from one another. In fact, listening and learning better from peers is one of our first hard lessons learned.

1. Pick good people -- and listen
"Early in my career, I signed a contract that ended up being a bad business decision. I was confident I had gathered all the data I needed, but I failed to gain the viewpoints of my fellow workers, so I missed some key information. Now I surround myself with the best and brightest individuals, and I hear them out. Diversity and collaboration provide the forum for the best decision making."

CIO profile of John Schanz, Comcast Cable.

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Sara Peters
Sara Peters,
User Rank: Ninja
11/19/2013 | 10:20:52 AM
tricky one
"The timeframe was too tight -- but rather than risk the deal, I signed up for commitments that couldn't be delivered on."  I think that's an all-too-common conundrum, and one that can only be avoided if you're confident enough to say "no" or "no, we can't do that, but we can do this."

Of course it's a lot harder to avoid that problem if the people making those commitments are not the people who have to deliver them.

User Rank: Author
11/19/2013 | 10:19:23 AM
Early in my career
Great observation about how often CIOs (let's face it, every manager) preface lessons learned with "early in my career". I've heard it time after time. Of course, in speaking with CIOs it's apparent that not everyone made their mistakes early in their career; every new CIO ends up fixing the mistakes that their predecessors made "late in their career".

Thanks for sharing these lessons.
User Rank: Author
11/19/2013 | 9:51:31 AM
Re: Great Advice
...that every setback, even the biggest ones, can be an opportunity to do things differently next time. It's more than "learn from your mistakes." Setbacks are opportunities to change your thinking, organizational structure, practices. The end of one world can be the beginning of another. Sounds like management-speak, but it's the best advice I ever got. 
Alison Diana
Alison Diana,
User Rank: Moderator
11/19/2013 | 9:50:53 AM
When speaking to solution provider CEOs, CIOs, and presidents, one good piece of advice they'll tell me is to fire bad customers fast. Sure, landing a big contract is exciting. But if it's outside your experience; the client is impossible to work with, or the goal post is constantly moving, you'll never meet expectations and that means you can't concentrate on those clients whose work you can do. At the end of the day, you'll have several dissatisfied customers. And that's not good for anyone. 
User Rank: Author
11/19/2013 | 9:43:17 AM
Great Advice
Some really good advice for work and life in this slideshow. The best I ever got was from my first boss: Never Assume -- Because you make an A$$ out of U and ME. What was the best advice you ever got?
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