A fictional but all too realistic cry from the heart of your average Fortune 1000 CIO.

TO: Trusted Colleague

FR: CIO of Fortune 1000 company

RE: My CEO

Please don't distribute this. I'm sending this to you in confidence because I take your request for advice seriously. Don't repeat the dumb mistakes I've made with my CEO. Yes, I've learned a lot leading and managing IT strategy and implementation in my company. But I've learned much more trying to lead and manage my CEO.

Those lessons have been painful, difficult and frustrating. It feels like he doesn't understand, doesn't care or doesn't appreciate either what IT can do for the company or what I can do as CIO to help him succeed. IT is doing a good job. I'm doing a good job. But we're not being given the chance or the opportunity to do a great job. We're not failing, but I can't honestly say that we're succeeding either. Did I mention that I'm frustrated?

My CEO thinks that "good enough" is "good enough"- except when it isn't. He doesn't want "more for less"; he wants "more for nothing". When we get an app or system tuned to the point where it's both robust and reliable, he starts pestering me about outsourcing it to save money. At the same time, he moans that IT isn't as "strategic" or as much of a "core differentiator" as he wants it to be. IT's damned if we do and damned if we don't. Of course, he's got yahoos pitching business from McKinsey, Accenture, Infosys or BearingPoint every week, telling him that he isn't getting enough "bang" for his IT buck. He wants what he wants when he wants it - except when he doesn't.

For example, we had done a terrific job with the business units defining and process-mapping an enterprise CRM. I was pleasantly surprised by the quality of the collaboration. So was the CEO. The vendor we selected came in with a budget and a schedule and a willingness to work with us that was truly impressive.

So what happened? Sales was so enthusiastic - and then threatened - by the CRM system's momentum that they went out and purchased their own multimillion-dollar CRM for their own use! Did they tell me? Sure. After they bought the system.

Sales insisted that their CRM would "complement" the enterprise CRM rather than compete with it. Yes, and pigs fly. They swore that they needed their own system to support sales' "special needs". They insisted they - and the company - needed both.

Of course, guess who had to pay to support and maintain the new sales CRM? That's right. IT. So I go to the CEO and explain - politely, completely and with Excel - how much this was really going to cost. Moreover, I communicated that letting sales do this really undermined both the spirit and the substance of the enterprise CRM initiative. I all but said that sales' subversion undermined the collaboration that the CEO himself had blessed.

No sale. My CEO looked at me, told me to make it work and insisted that I come up with a way to integrate the two systems when our enterprise CRM came online. I again explained that this would be technically difficult and expensive. Moreover, did he really want to send the message that it was OK for business groups to go off on their own and pay for deployments that could hurt the enterprise? My CEO said he understood my concerns. However, he felt that IT should take one for the team. "IT's job is to support the business," he told me. He actually told me that he liked the fact that the enterprise CRM initiative had "lit a fire" under sales.

He then looked me in the eye and told me that IT had to take money from its CRM development to pay for the sales CRM. I was livid. I later heard from the COO that the CEO was disappointed that I wasn't more supportive of his decision. He felt I wasn't being a "team player". The COO quoted the CEO as saying: "Sales makes money and is closer to the channel than IT. You would think IT would be smart enough to use sales' interest in CRM to drive the enterprise CRM."

I still don't know whether the COO was yanking my chain. But I can tell you this: I've got a CEO who behaves as if business technologies and business processes are "plug-and-play". You and I know they're not. I can't tell you how frustrating it is to have a CEO who treats good faith efforts by IT to improve the entire enterprise as a chit that can be swapped to appease the head of a business unit.

The truth is, I know a lot of these frustrations are my fault. I've probably spent too much time and effort trying to do the best job possible rather than doing what the CEO thought was the best job possible. I have a CEO who loves to make executive decisions based on an inadequate understanding of technology. And I've done a mediocre job of educating him on the technology trade-offs. To be fair to me, my CEO is not into being educated by his people. To be fair to him, whenever I try to explain the business trade-offs associated with tech investments, he tells me that the business trade-offs are his call, not mine. He says he wants a better sense of how next year's technology changes will affect his business options.

The bottom line is that I am trying to run IT as a business, but he wants me to run it as a technology group - except when he wants me to compromise on the technology so that other business units can do what they want. Then, of course, he wants me to run IT as a support group.

I can't read my CEO's mind; I can't figure out where he's really trying to get value from IT; and I can't figure out whether IT is a pain in his butt or his go-to trouble-shooter that he takes for granted. I'm frustrated because I can't figure the guy out. But, most of all, I'm frustrated with myself. Why? Because I have allowed myself to get into this position. Even worse, my people are as frustrated as I am. My CEO's ambivalence about IT is reflected by the entire organization's ambivalence about IT. What does it feel like? It feels bad.

Michael Schrage is codirector of the MIT Media Lab's eMarkets Initiative. He can be reached at schrage@media.mit.edu