On the Outside Looking In\n\n\nQ: I am a contractor and trying to expand into specialized areas of consulting, but I am finding it hard to break out of the mold of contracting and agencies. How do you get yourself in a position to market yourself as a specialist in a field? And where do you start?\n \n\nA: There are two issues here. First, the specialization factor is clearly a catch-22. It\u2019s nearly impossible to get an assignment requiring a particular type of technical or functional expertise without already possessing relevant knowledge and experience. And it\u2019s similarly difficult to get the appropriate experience since you can\u2019t get that type of assignment in the first place. The answer here is to be part of a team on which you have value to offer, and at the same time can acquire exposure to something new. This is an excellent rule of thumb for all consultants to ensure ongoing acquisition of additional skills and fresh experiences. Your second issue, the challenge of establishing and marketing yourself as an independent consultant, is probably best passed on by me. There are many books, publications and websites dealing with this subject, and several organizations of like-minded individuals where you can learn the ropes. Good luck.\nStartup Blues\n\n\nQ: I am recently unemployed. I had a director position within my company for just less than one year and have an opportunity to interview for a CIO position at a startup company. Since this position will not provide any income until the company\u2019s funding request has been approved, I have decided I will continue to pursue full-time, director-level positions in the market. If I am selected for and accept the CIO position, should I pursue contract or full-time positions until the funding is granted? And what should I tell the prospective recruiter trying to sell me to an employer if I seek a contracting position?\n \n\nA: None of the above! If you choose the high risk and reward opportunity of working at a startup company, with or without funding in place, you simply must give it your full and undivided focus and energy or you will surely fail. You should receive a significant equity stake in the venture in consideration of your signing on at such an early stage and not drawing any salary?enough to keep you and your management teammates focused on success. However, if you cannot sustain yourself financially or emotionally without a regular paycheck, then pass on this opportunity and continue your job search.\nLeadership Ambitions\n\n\nQ: I have an engineering bachelor\u2019s degree, a computer science master\u2019s degree and a PhD. I have taught for three years and have been in the industry for the past eight years, with four different companies. I have worked as a consultant, a systems manager, scientist and architect. I have not done any real development work but have done a lot of project management and frequently help troubleshoot and fix problems. I have worked to develop IT strategy for a manufacturing environment and most recently in supply chain management. I have tried to get into positions of leadership (for example, director or above), but I have not been successful. What would get me there?\n \n\nA: It\u2019s very challenging for me to give specific recommendations without knowing you as an individual or at least seeing a r\u017dsum\u017d, but a few things stand out in your scenario. First, what are you?a consultant, an analyst, an architect or a manager?and how are you projecting and selling yourself both on paper and face-to-face? If your current title and responsibilities are nonmanagerial, then you are asking a CIO to take a leap of faith with you and to risk offending existing staff who would also like a chance to be bumped up the ladder. Second, most CIOs will have a tough time bringing onboard a new director who has never done hands-on work in the trenches. While project management does not dictate this experience, it\u2019s clear that a strong background as an individual contributor establishes technical credibility and makes one better able to direct the technical efforts of others. Third, my antennae go up on your career history of teaching for three years and then working at four jobs in eight years. How are you presenting and explaining this in interviews? And speaking of interviews, have you sought feedback on your skills in this crucial area, or on your communication skills generally? All things being equal, I recommend staying put, build some tenure and work your way up into management from within?assuming that\u2019s possible at your current employer. If not, seek out lateral opportunities at corporations with strong reputations for professional development of IT leadership and give it your very best effort.\nReopening a Door\n\n\nQ: I turned down a midmanagement IT position at a Fortune 5 company last year through a recruiting firm, and now I want to work for that company. Should I return to the same recruiter, go elsewhere or apply directly?\n \n\nA: Your first try and very best bet should be to circle back to the recruiter who contacted you last year. The odds are pretty good that she is still doing business with your dream company and, if so, will be your best advocate and your surest way to connect to the company. Ask the recruiter the direct question of your likelihood of successfully opening the door, and you will probably get a direct answer. If not, or if you sense a bait and switch on this go-round, then politely withdraw from the relationship and contact the targeted company directly?through the jobs page on the company\u2019s website and by a letter personally addressed to the CIO. Last, the only reason to go to another recruiter is if you know for sure that Recruiter A from last year has been replaced by Recruiter B this year.\nCareer Coaches\n\n\nQ: As a young CIO, I\u2019m looking for additional help, and I am considering hiring a coach. What are the pros and cons of heading down this avenue, and do you have any suggestion as to where I should look?\n \n\nA: I think that coaches can be a wonderful way of acquiring a third-party look at yourself, and a very productive and accelerated way to address personal weaknesses and develop your individual strengths. Coaching resources and referral sources include the International Coach Federation (www.coachfederation.org), Coach University Coach Referral Service (www.coachreferral.com) and The Coaches Training Institute Coaching Referral Service (www.thecoaches.com). Additionally, you might consider engaging a retired or per diem CIO as a mentor on a consulting basis to coach you professionally through the white waters of your new position.