Checkered Work History

Question
I have a checkered work history. I recently have been working in my assigned career field involving PC and LAN installations in major hotel chains and other chain stores, but this is only for a temporary installation. For 10 years I have mostly worked in the IT technical services field, but because of the nature of IT services, if you do not work directly for the employer you are working through one of their contract companies such as Volt. The reason why I am mentioning this is the fact that I have gaps in employment, and most recently had to take a low paying security job lasting four years because I could not find an IT job after September 11th and feel these contract companies will frown on it. I feel that as a male the gaps in my employment history are working against me.

Because of my low pay I could not afford to pay my wife’s living expenses and go to school to update my skills in IT services (such as obtaining my MCSE). I have worked in a low paying security position because my wife threatened to kick me out of the door unless I bring in some income. I have been chastised by at least one employer during the interview because of the security job, for not doing enough to elevate my job experience.

How can I explain in the cover letter that my work in security was necessary to pay the bills? Does it show a sense of desperation? It’s very depressing, and because of my security work my wife had to subsidize me to pay the bills, which put her into credit card debt on the order of $30k. The IT market is now rebounding here in Vancouver, BC but credentials from other countries are not recognized. For example, there are pilots, doctors, chemical engineers, and nurses who immigrated here and ended up working as vacuum salesmen, taxi cab drivers and in other low paying positions. So I could not go back into my former line of work as an automotive mechanic or aviation. How do I explain my work history in my cover letter or is that just shooting myself in the foot?
Sincerely,
Frustrated

Answer
by John West Hadley, Career Search Counselor, “Helping Job Seekers Who Are Frustrated With Their Search”

Before you even think about your cover letter, I would advise you to take a step back and carefully examine:
1. What is your career goal? Don’t think just about the job you want right now, imagine where you want it to lead, and what you want to be doing in 5-10 years.
2. What do you need to achieve your goal? What skills, type and depth of experience, and qualities will you need to demonstrate to be able to get there?
3. What would be a good next step in your career that would put you on the road to developing the package you will need?
4. How does the package you have today align with that next step? This is your ‘reality check’ where you take a good hard look at whether this is an achievable next step.
5. Network with others in the field and see what they think. Come up with your strongest marketing message, and results-oriented description of your package, and test-market yourself to those in your network. If you consistently hear that your chosen next step isn’t going to be achievable, find out from them what you would need to do to get there – is there a smaller next step you can take, or critical certifications or training that would make you marketable?
6. Given the multiple-year gap, seriously consider pursuing additional training or certifications anyway – these will show that you haven’t just been doing something unrelated, but have done some work to keep yourself fresh and marketable.
7. What is your set of past accomplishments that will help sell you for this role? Spend a lot of time turning those into compelling, concise results-oriented stories.
8. Does your resume perform its intended role as a strong sales brochure for your candidacy? Given the checkered history, you will probably need to take a ‘functional’ approach to your resume instead of the standard chronological format.
9. Now you can start to think about your cover letter.

Your cover letter needs to show your passion for the particular job, company and operation, so you will need to do a lot of research before composing it. Find people you can network with who work for the company now, or who used to work for the company, or who know something about the operation (e.g., vendors who provided the company services or consultants who have done work for them).

Your letter needs to make a convincing case for why you would be a great addition to their operation. Think about the issues they face that you can help them deal with. Include bullet points that describe related accomplishments and the results you produced for past employers.

The cover letter also needs to describe briefly the package of skills, qualities and experience that you bring to the table, as it is relevant to this role and company. It doesn’t need to repeat everything in your resume, but should highlight the critical pieces that would make a hiring manage sit up and take notice of you.

Finally, it needs to close with confidence. It shouldn’t just express your hope that they will agree to meet with you. The strongest letters assume they will want to bring you in, present dates you are available, and state a specific date and time you will follow up.

Now, to your question about what to reveal about your checkered work history: You need to admit to it, because otherwise you will lose any credibility when it is noticed. The trick is to state it simply, matter-of-factly, without dwelling on it, and then to move on to why the potential employer shouldn’t be concerned about it. Your message is, in effect, “Because of the economic downturn after 9/11, I took a stopgap position in security. In the interim, I have done x, y and z to stay abreast of the market. I’m now ready to return to (your target role), and here is why I believe I would be an outstanding candidate.”

I have a Career Tips email newsletter that each month presents valuable advice on marketing yourself for a career search. I invite you to check out the contents of past issues and then sign up at www.JHACareers.com/Newsletter.htm.

Good luck!

Susan Ireland’s Two Cents
How about trying to slide back over into the high-tech field? Maybe you could identify a high-tech firm in Vancouver that you’d love to work in. Apply to that company for a position in security. Once you have that job, network within the company, learn about IT openings, and maybe you’ll have a better chance at winning the job as a company insider.