Ask The Secret CIO: Getting Into The Executive Suite

Want to know how to talk to a CIO, how to get a job as a CIO--and what's happening with Herb's long-promised book? The Secret CIO's got the answers.

InformationWeek Staff, Contributor

November 20, 2001

9 Min Read

Salespeople And The CIO
As an account manager representing one of the largest solutions providers in the industry, I have grown to believe in our company's abilities and genuine concern to do things effectively for our customers.

I find it very frustrating that not one CIO I've attempted to contact has responded. I haven't even been shown the respect of having an admin return my calls.

What does it take to access a CIO these days? How many cost-effective value propositions do they pass up by being too busy to have a phone conversation?

Sign me,

Dear Confused:
Since you are still in sales, I assume that at least some individuals in your target companies have returned your calls. If not, you work for an unusually forgiving manager.

To increase the likelihood of getting a response, I hope you're preceding your phone call to the CIO with a letter explaining your value proposition. If so, when you telephone you should expect to either speak to the CIO or be directed by the executive assistant to the right person in the company to hear your pitch.

While some people are rude and do not return calls, most executive assistants are good at their jobs and will identify to potential vendors the right path to follow. If this is your situation, are you still trying to get through to the CIO? If so, it wouldn't be surprising that, after a while, the executive assistant would get tired of telling you who to contact, and finally would not return your calls.

On the other hand, I do know that some executives seem to pride themselves on being too important to be polite to salespeople. What really annoys me are the oh-so-busy important people who can't at the very least have their executive assistants return their phone calls. It's only common courtesy to let salespeople know that you personally are not interested in their wares, instead of making them figure it out by having their repeated calls go unreturned.

If you're unable to get direction to the proper individual, then write a letter to the CIO. Explain that you've been unable to reach him or her. Briefly make the case for your compelling value proposition. Ask that when you call you be put in contact with someone who can evaluate your offerings.

If you're still unable to speak to anyone in the company, stop wasting your time, and move on to another potential client. You're dealing with a company that has no class.

No Matter What I Do, I Can't Seem To Get Ahead
Dear Mr. Lovelace:
I'm discouraged and disappointed about my career and need some advice from you. I have done everything right. I got an M.B.A. at age 40, have Big Five background and 16 years in IT, strategy, business development, delivery, systems integration, and so on.

I don't have large-scale operational and budget responsibility. How do I create a career path into a CIO position? I must have sent out 5,000 resumes. Everyone says that I have a very impressive background, but nobody wants to give me the chance.


I'm saddened by your difficulty. It's tough when you work so hard at succeeding and feel you don't have enough to show for your efforts. Here are a few thoughts to consider:

  • The key to getting the job you want is networking, not sending out resumes. Talk to people you know. Ask for their opinions about your strengths and the areas that need strengthening. Listen to what they have to say.

  • Expand your network. Ask each person you talk to if he knows someone else with whom you should speak. Get a few names from each one. You're looking to learn from them, not ask them for a job.

  • Make sure your expectations are realistic. You won't go from a mid-level manager or a consultant position to a CIO job unless you hit upon a highly unusual opportunity.

  • See if your interviewing skills are what you want them to be. Ask a friend who's in sales to share his or her observations. Listen to what you hear. Get a few opinions.

  • In your interviews, stress accomplishments, not education. Talk about where you saved money or improved the company's bottom line, not which projects you worked on or what committees you were a member of.

  • Focus on what you can do for a company, not what they can do for you. Ask the next interviewer you meet what problems they have. Then discuss how your skills can help them.

My best wishes to you in your search. Please let me know how you make out in your efforts.

So What Happened To The Book, Herb?
Do you still have a book in the works? As I read this week's column in the magazine, I thought about how many articles of yours I'd have if I had saved them through the years. I'm sorry I didn't.


Dear Dave:
Yes, the book is still under way. However, progress is going as slowly as the efforts to reap benefits from an enterprise resource planning project.

Every time I sit down to work on the book, I get distracted, and the book goes back to its sad little place in my computer, feeling neglected. But I can update you with what I've completed or worked out so far.

The book will give some background on how I came to write these columns and my purpose in doing so. It'll include a brief biography of each major character--Gornish, Kratmeyer, Phil, and, of course, Cindy. Then, the first 100 or so columns will be republished, along with additional information--the background of why I wrote it and some of the more interesting comments I received from readers. My objective is to flesh out the topics and give insight into Herb and his world.

Miller-Freeman, the publishing arm of InformationWeek's parent, will have the right of first refusal on publishing the book.

I hope to get very serious about finishing the book in the near future. In the meantime, readers who are interested in being notified about the book when it's close to being completed should send me an E-mail with the subject line BOOK. Those sorts of notes tend to give me the incentive to work on the manuscript instead of brooding about the latest slight to me by Kratmeyer, et al.

The Department Director Distrusts IT
Dear Mr. Lovelace:
I thoroughly enjoy your articles. Now, I have a situation you haven't really touched on in your columns. I remember you writing about the problems of vendors ignoring the IT organization and going directly to users (Selling Around The CIO). There's another issue which is very similar, which we can call here "buying around the IS director."

In this case, it's a board member (who's also a departmental director) who insists on running his department his way. At first, I tried some of the perilous tactics mentioned in that article of yours. I later tried the one you suggested as the appropriate course. This also failed because he distrusts IT due to our incompetence. Our incompetence, however, is due in large part to the atmosphere in which we're forced to work.

In the past, we'd be the last ones to hear about all the new stuff going on in the place. Then, we'd work our butts off to make sure that it worked, which it rarely did. This meant that we had (1) messed up the consultant or vendor's "perfect" system, or (2) worked too hard, in his opinion, to get it up and running.

Now I let him handle the project--start to finish. It almost always fails. He still continues to bring things in on his own, but there's a lot less stress in my area, and the entire burden is on him. In the last four years (I've been here seven), none of his projects (two or three a year) have succeeded as he said they would. And the burden of these failures is his, not mine.


Dear Antigone:
Let me see if I understand the situation. You have an important executive who doesn't think the IT organization has a good track record. This person goes around IT and tries to run his own projects, but invariably fails to meet his own deadlines or objectives. You're pleased that the failures are his, not yours.

It seems to me that you should seriously consider looking for another job--both for your own good and the good of the company. Consider how corrosive it is on your professional abilities to get your pleasure from watching someone else fail, instead of being able to point with pride to what you have mutually accomplished.

I suspect it is too late, after four years of this relationship, for you to sit down with him and try to get a new start. However, if you really feel bonded to your present company, it'd be worth a try. Admit that your organization has not met his organization; explain your own frustrations; listen to his complaints; ask what you can do to improve communication and performance.

If you're unwilling to try to make things better or feel it'd be a grand waste of your time, then get out of the company. You would be doing everyone, your staff, your users, the company, and yourself, a big favor.

Your letters to my print column and E-mail forum raise some serious issues about managing information technology in today's world. Since today's world is essentially absurd, my serious responses may sometimes sound a little whimsical, and my occasional whimsical one, serious. If you want to participate or comment, write to me at [email protected]. I reserve the right to edit for size and content. Sign your E-mail the way you want it to appear online. And feel free to join me in my discussion forum.

As I've mentioned, I'm planning to put my

InformationWeek columns into a book with additional commentary around the events and people about whom I write. If you'd like to be notified of such an event, please drop me an E-mail; I'll build a mailing list to let you know about it. Just use the word BOOK as the subject line.

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