Interviewing for the executive suite (and be careful what you wish for...)

Getting to the C Suite is a laudable and understandable goal for many current and future technology executives. However, too many IT leaders have an 'aim, fire, ready' mentality and don't ask the tough questions that will help them determine if their dream job is located in the wrong executive suite.

fork road
Credit: Ian Paterson

“Two roads diverged in a yellow wood,

And sorry I could not travel both

And be one traveler, long I stood”

–Robert Frost ("The Road Not Taken")

A big part of my job in executive search is to assess a candidate’s motivation and drive. A big part of my job in executive performance coaching is helping my clients align their motivation and drive with their companies. One of the questions I ask in an interview is: “Regardless of how happy you may be, what would you like to see in your next role that you don’t have now?” It sounds innocuous enough but it tends to provoke answers that typically include the desire to report to the CEO: “It’s a seat at the table.” “I’ll have Board access.” “I’ll finally have influence.” “It’ll make it much easier for me to eventually become a COO or CEO.”

Some of my candidates and executive coaching clients tend to overlook the true drivers of genuine, long term executive success when they set their hearts on reporting to the CEO of a company: chemistry, cultural fit, influencing skills, adaptability and courage, to name just a handful. Excellent executives are more interested in determining if their potential manager and the leadership team possess these assets than they are in titles.

How one executive managed his journey

One of my executive coaching clients was a C Suite CIO in transition who was offered a role – several levels removed from the C Suite, I might add – in a B2C company in which he’d have global responsibilities for the company’s digital, customer facing transformation. Despite the seeming downward career direction of the role, I advised him to take it (and there were numerous voices who warned him that he’d never see the inside of the C Suite or wear a CIO title again). Long story short, the role and attendant responsibilities eventually enabled him to join a global consumer services company as the CIO, reporting to you-know-who.

Preparation is key

Meticulous, near-obsessive preparation has always been a crucial component to executive success. Preparing thoughtful, probing discovery questions before an interview or meeting will help you understand the company’s culture as well as the strategic vision of the executive leadership team. Preparing for the questions you don’t want to be asked can be equally, if not more important to a positive outcome. And, most importantly, your emotional intelligence will help you determine whether or not you can work for and partner with the person in front of you, regardless of his title.

These are some of the same questions I ask executives during assessments, so I hope you find them useful as well:

Who will be your key partners and collaborators within the organization?

You need to understand the individual’s influence within the company and the level of respect he generates. His ability to influence people and events will be an important determinant in your ability to effect change. This question will also help you get a sense of how this individual goes about assessing risk and overcoming challenges. The prospect of working for a collaborative and respected CFO or COO will likely net you a more productive and long lasting experience with your new company than hitching your star to a disengaged or isolated CEO.

What are some of the accomplishments they’re most proud of?

Working for an intelligent person who really ‘gets’ technology can be a wonderful thing. But if your prospective boss doesn’t have a successful track record of delivering results then regardless of his title, you may feel very frustrated very quickly and end up following him out the door when the Board catches up with his performance.

What are some of the significant technology initiatives in flight and what is on the drawing board?

It’s important for you to gauge how conversant and comfortable this person is with technology’s inherently disruptive capabilities. He doesn’t need to have a financial background to view technology as ‘merely’ a cost. I’ve sat in front of more than a few CFO’s who see technology as their company’s future and because they know where the bottom line actually exists, are prepared to build a case for an aggressive capital budget.

What will success look like over the next one to three years?

You have to understand the depth and breadth of this person’s vision. What does the future look like to this executive? What is the roadmap for getting there? Would you be working for a CEO who’s bent on playing it safe and doesn’t want to challenge the Board? Or, rather, a COO who understands the need for transformation and has a track record of championing innovative executives who drive change? Ask yourself which person is more likely to view technology as a differentiator for the company’s success.

You’re a successful executive because you have never taken a cookie cutter approach to solving problems and meeting your goals. Curiosity and an open mind are two of the main reasons why you have been an invaluable member of various organizations. So why take a cookie cutter approach to your own career? The letters in a person’s title only scratch the surface of who they are, what they have accomplished and where they are going.

"Two roads diverged in a wood, And I –

I took the one less traveled by,

And that has made all the difference.”

Robert Frost ("The Road Not Taken")

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