As a headhunter in the technology sector I am an almost obligatory stop on the networking circuit of many executive job seekers. I hold the promise of a barometer on the employment market, contacts, ideas, and ongoing searches which may be suited to the job seeker. I am always happy to participate in courtesy interviews as I neither envy the job seekers’ circumstances nor take lightly the courage it takes to reach out to me.

After participating in literally hundreds of courtesy interviews over the years however, I am ever less inclined to serve as a passive sounding board, listening patiently as job seekers list their job preferences and goals. Instead, I have taken to challenging what I am told, not to embarrass, belittle or discourage the job seeker, but rather to nudge them to make the most of the journeys they find themselves on. In the spirit of ‘forewarned is forearmed’ expect a little push-back on the following assertions in our ‘courtesy’ interview.


1. ‘I am open to anything from running IBM to an early stage technology company.’

Many job seekers believe that it is advantageous to frame their search as broadly as possible, thereby keeping their ‘options open’.  It is the job-hunting equivalent of calculating the odds of hitting a target with a shotgun versus a rifle. By emphasizing their versatility and breadth of experience, job seekers hope to receive consideration for a wide range of job opportunities while avoiding being narrowly pegged as a one trick executive pony. While it is difficult to advise people against expanding their job choices there are a number of reasons why this approach should be carefully considered.

First, keeping your options open complicates rather than simplifies your search. How do you conduct an efficient job search when your target market includes both large and small companies, Canadian and subsidiary, as well as a whole host of technology segments?  This may not be an insurmountable issue in smaller communities where every firm can be identified within a defined geographic area, but in the greater Toronto area your target market is concurrently everywhere and nowhere. Where to start and how to plan your job search becomes a major challenge. Job opportunities become islands onto themselves and you find yourself jumping from one to another without ever getting a feel for any given market. Without some rigor in narrowing your target employment markets you risk becoming scattered, unfocused and eventually frustrated.

Second, the odds are high that you are not equally suited to managing both IBM and a startup company let alone across the full spectrum of contexts faced by these companies. Early stage companies call for different skills than large corporations, and it is likely that your portfolio of skills, personality and experiences skew to one end of that spectrum more than the other. While you may argue, and many do, that leadership and management skills transcend firm size, life stage or context, be prepared for more than a few skeptics who will question whether you have figured out, or are being honest about, your strengths and preferences. You unwittingly shift the onus onto the interviewer to do the sorting and since many search consultants, not to mention potential employers, are not up to that task be prepared for a lot of unproductive activity. For example, you may find yourself initially buoyed by a flurry of market nibbles and exploratory interviews. Companies extend invitations for you to return for second and third interviews involving an expanding number of stakeholders.  Eventually, the lengthy deliberations prove frustrating and you become confused by the indecisiveness of the organizations in question.  Meanwhile, the employers cannot evaluate whether the ‘generalist’, as you have described yourself, can deliver the specialist results they seek. They waffle or mitigate their risks by extending contract assignments thus ‘test driving’ you before buying. You cannot see the link between your strategy of keeping your options open and the situation at hand.  


2. I think I am ready to do a start-up

I frequently meet job seekers who, after a career with a large corporation or a series of large corporations, decide that they would like to manage a small entrepreneurial company. They have a predictable line of reasoning to support their decision; perhaps they established the Canadian subsidiary of their corporation, or they were assigned responsibility for a small profit centre. They argue that they have always been ‘entrepreneurial’ despite working for firms not known for those qualities.

It is not my place to dissuade the job seeker from such aspirations. However, many employers understand, and if they don’t it is my job to advise them, that the transitional issues in such moves are not insignificant. Employers can be expected to be cautious and thus the job seeker genuinely seeking to make such a move should be prepared to mount a vigorous, well-researched defense of their rationale if they hope to be successful.

Rather than offering unsubstantiated generalities, a job-seeker attempting a major career shift should do their homework starting with reaching out to executives who have successfully made the transition being contemplated. They should probe into how the corporate life being sought differs from the one they have lived. They should enquire into the specific transitional challenges, the adjustments and the qualities required to successfully address them. What evidence is there that these align with the job seeker’s strengths? A professional manager contemplating a move to a small company is like a professional boxer, trained to perform in a regulation sized boxing ring deciding to become a back-alley, ‘anything-goes’ street fighter. While both are forms of fighting, they are very different and the candidate better be able to speak to and prepare for those differences or risk a lot of pain. The homework process itself is extremely helpful as it may dispel the job seeker of his or her transitional notions or better equip them to explain why they will be successful.


3. I want to move into the tech sector.

I am regularly approached by executives seeking to transition sectors. It may be an automotive parts executive who wants to move into the wireless communications sector, or a forestry executive who desires to move into the software industry. Such moves, while difficult, are achievable though they will not happen simply because the job seeker wants them to.

The key to making a major sector shift is finding bridges to your desired destination. You are unlikely to easily transition from 20 years in the trucking sector to being considered for a role in a consumer software company.  There are simply no obvious links between the two worlds. To switch markets or sectors you need bridges which minimize the risks for all parties concerned. Bridges are knowledge, contacts or experience with technologies, markets, sales channels or people. Thus, if you are intimate with the world of trucking but want to move into the tech sector, consider the many technologies used by the trucking sector. It may be a host of services, software, communications or hardware technologies. Talk to the head of IT in your current organization about developments in the field and emerging technologies which will impact the sector. Your knowledge of the sector, its cadence, procurement patterns and your contacts are effective bridges to any organization seeking to do business into that market.  This is the easiest way to engineer such a move.

Second, a job seeker endeavoring to transition into a different sector or type of company should be clear about the price they are willing to pay for such a move. Tuition is often required in order to learn something new and the job seeker should have a price he or she is willing to consider. The tuition may be in the form of a reduced role, title, or compensation as the executive demonstrates his or her ability to make a contribution to a new employer. While bridges will reduce the tuition needed they will not always eliminate them. The executive who has significant obligations in the form of university-aged children or large financial obligations such as mortgages may not be in a position to bear the burden of a large transitional tuition and should adjust their short-term aspirations and strategies accordingly. Otherwise, the journey which faces them promises frustration.


4. I am comfortable and experienced in marketing, sales or business development.

Listing the functions you have worked in does not tell me what you have accomplished, in what contexts you have been most successful, or where you are most passionate and effective. My job is to help companies and candidates make the right hiring decisions. It is about fitting square candidate pegs into square employment holes. I cannot do this if I am left to divine where the job seeker fits.

While you may well have managed sales, marketing and business development over the years in a variety of situations, there are likely themes around where and when you were most effective, not to mention where you had the most enjoyment. This is not to say that there are not executives who thrive in almost every role across every situation, though these are the exceptions rather than the rules and employers are seeking to minimize not maximize their hiring risks. Know your career themes and be prepared to openly discuss them.


5. I left my employer yesterday and thought I would call you immediately.

Many executives equate losing their jobs to falling off a horse, and believe they must immediately climb back on. They start making phone calls filling their schedules with networking and related job search activities. In interviews, they invariably describe a desired future eerily similar to their immediate past.

While many of these executives may well be genuine in their aspirations, I am often left with the feeling that they are missing or avoiding an opportunity to step back and take stock of their careers before jumping back into the fray.

One of the key attributes organizations look for in executives, or at least should look for, is self-awareness. Knowing your capabilities, style, preferences, personality and developmental opportunities is a precondition to the purposeful pursuit of personal growth and to making a good employment decisions. Job-loss is a perfect opportunity to calibrate, to reflect on where your career has taken you relative to where you thought you were going to take it. It is a chance to discuss options and tradeoffs with your family and to reset your bearings.

If you have been offered outplacement counseling, take it. It will provide you with tools and resources which will help you navigate this inward journey. If you haven’t, there are scores of resources available to help you start the journey. Either way, don’t immediately jump back on that horse as it may very well have been trying to tell you something when it threw you off.


6. I am making the rounds of all of the headhunters…

There are hundreds of search firms listed in the Toronto directory of recruiters and some job-seekers send their resumes to all of them. In fact, it becomes the singular focus of their job search activities. I regularly receive resumes and phone calls from fork-lift operators, chemists, oil and gas workers and teachers. Since my firm focuses almost exclusively on finding senior executives within the technology sector, it is highly unlikely that I can be of any assistance to many of these people.

Search firms specialize in sectors or functions and so should you. Enquire into which firms work in your field or specialty and are most likely to undertake the type of searches of greatest interest to you. These are the only firms you should be contacting. Also, there are big differences between search firms and placement agencies. Know the difference and what each can or cannot do for you.

Finally, headhunters are one piece of your overall job search strategy. You do not want to entrust them with the responsibility of your job search. Only you should own that. Keep in touch with a few but do the bulk of the work yourself in a systematic and purposeful fashion.

As you are now forewarned and hopefully forearmed, I look forward to our courtesy interview.