What I Wish Managers Knew About Being A Jack-Of-All-Trades

Photo Credit: Matthew Stumphy at gurustump.com
Being a Jack-of-All-Trades can be tough when most jobs have very narrowly defined descriptions. Here's a list of things to consider when considering a versatile employee.
Last night, I watched the young adult sci-fi flick Divergent, set in a future where citizens in a post-apocalyptic society are separated into five factions depending on their nature and talents. These factions are charged with fulfilling a specific need of that society, such as food production, public service, defense, or science, etc. Divergents were those who don't fit neatly into these factions because they display the talents and abilities of several factions and are thus hunted because they mess with the program. Like much young adult post-apocalyptic fare, it's a grossly oversimplified allegory for growing up and finding a calling while preserving some amount of one's youthful spirit in the process. I watched this at 1 a.m. on a Monday morning because I am unemployed and have nothing to do on Monday proper except laundry and mining LinkedIn for job postings. I have been job hunting in earnest for six months and yet nothing with any sort of potential has panned out. To be fair, there are lots of factors at play: it's a tough economy, granted; and year-end is hardly the best time to ask someone to take me on, surely; and, familial obligations require I find a job with a certain level of compensation or else I am worth more to my family uncommitted, and yet there is one more thing complicating this already difficult situation.
I am a jack-of-all-trades, to use the pejorative. Others might call me a dilettante or a dabbler. I prefer to think of myself as a professional generalist, but we all know the type: those professionals that can sort of do anything, work in any mode, take on any task. They often will end up in a career light years away from the discipline of their formal education. They are the co-worker that you might ask to fix your computer because he or she can do it faster than calling IT, and they are glad for the little distraction. They may work several short jobs in wildly disparate fields, willing to move onto the next thing because they are confidant there will always be a next thing and don't seem to have any clear professional trajectory. These are the problem solvers and masters of synergy and integration and yet are anathema to managers because their skills are tough to define and they can be tricky to place into one narrowly defined job. In the metaphor of square pegs and round holes, these workers are mold-able clay pegs that are ready to move on.
My resume appears to a hiring manager as a shiftless wanderer trying out professions as a bride might try on dresses. I am "divergent" in regards to a career track and while the movie seemed to portray it as some noble quality that we should all aspire to, it's been mostly a pain in the ass. I have a broad education in the humanities and a Bachelor's degree in English. My first jobs were in retail and customer service, and after that, a set of construction jobs and meter reading during college, which would hardly count against anyone. I have worked in education as a substitute teacher and have volunteer service in youth camp leadership. I have many years working on a university campus in office admin then promoted to an information technology position administrating database applications and websites. I resigned from that 9-5, M-F position to be a stay-at-home dad at the birth of my first child. With my days free, I freelanced as a work-from-home newsletter editor, administrator and membership director for a small non-profit and also serviced half a dozen websites for a web development company. I built databases and did graphic design for private clients. As my kids got into school, I spent day times selling print advertising and running a small daily deals website for a weekly publication and even worked as a prep cook. All the while, my passion for music developed into building a small business providing professional audio and entertainment production services for local malls, restaurants and private clients booking musical talent, DJing weddings, hosting karaoke, doing event planning and production, renting sound equipment, and moonlighting as an audio engineer for hire. At one point I felt like I could do anything, learn anything, be dropped into any job and hit the ground running, learn what I need to quickly to be proficient in almost any position....until I yearned for the stability and schedule of a 9-5 M-F job again and found that no one had the same opinion
I've heard the same word over and over again, "overqualified." At first I took that as a compliment. I must be so awesome, this company isn't ready for me yet. If I'm overqualified here, I must be looking at jobs below my potential so I set my sights higher but scanning even the most modest of next step-up positions, I instantly recognized I lack the experience and education to even meet the basic requirements. I don't have the right schooling for jobs in the tech sector, I lack the requisite experience for anything in the Humanities, nearly every administration listing is seeking entry level candidates and any 9-5 job in audio or event planning pays too little for me to consider. Any job that I might have worked my way up from the bottom to have a respectable position in at my age, nearing 40, is filled with younger people who are either dedicated to that industry or, more grim, so lacking in other options that to hire them is a safe bet that they will stay.
I quickly learned that "overqualified" was hiring manager code for "flight risk." Obviously hiring and training people costs time and money and a company wants to be confident that resources spent on a new hire will be spent well and the value of those invested resources will pay off in years of service. If a company sees a resume of a guy who spends 4-5 years at each position and it looks like each job is a steady step to the side or up from a person's previous position, they can be relatively certain that the hire is stable and they can get some good years out of that person. My resume, on the other hand, is a Frankenstein's Monster of odd jobs, and tangential forays into unrelated fields, most of which last a year or less and has, so far, sent hiring managers running for the hills.
For any job that might draw a decent wage, the fear, I assume, is that I appear to be someone with a smattering of an amateur's knowledge in each field, but nothing approaching the deep expertise of a candidate they hoped their high salary would draw, and in this job market, they almost certainly have safer candidates to consider. For jobs with lower salaries, and those considered blue-collar, the fear I've heard very plainly expressed is that I would be bored, or underutilized, and the pay wouldn't meet my needs and I would move on quickly. The part that I haven't heard so plainly expressed, but implied, is that I wouldn't fit in culturally, as a tech-savvy, educated person with an office background working in a blue collar environment.
Most businesses and organizations maintain fairly rigid job positions. A manager fires the last front-end web-developer, she needs another front-end web developer. She advertizes for a front-end web developer, and gets a stack of resumes from 29 people for whom front-end web developer is the exact previous job title and then one resume from a guy who has all the requisite skills to be a front-end web developer if you could piece together the skills from four other jobs over ten years and could easily jump into that job, AND can help out with the marketing and sales team, AND work on the back end database, AND answer the customer support line when you need him. It's easy to breeze past that last resume because it doesn't say "Front-End Web Developer" on it. A guy with extraneous skills might be a help to other departments or the company as a whole, and might be great management or executive material because he can see outside of his narrow set of responsibilities but its messy to coordinate those efforts and a manager concerned with simply getting the job done might be unwilling to provide the support needed to take advantage of those abilities. I'm not trying to undercut the value of specific training or formal education; without a doubt, its critical to know that your hire has every advantage to perform in the job you are hiring him or her, and certainly, if you need a CPA or a certified systems engineer, nothing else will do. Sometimes, though, a position is defined narrowly for no other reason than "because that's what the last person did" and you can be open to considering someone who might perform just fine in the role at hand who might not be cut from the same cloth as other more traditional professionals.
I can't fault hiring managers who pass on jack-of-all-trades. No doubt their apprehension is founded in common business sense and their own instincts. My resume is certainly challenging but I ask, "What to do with a guy whose skills and talents are tough to define?" I wonder if I can plead to this court of public opinion (who am I kidding, in this court of my wife and two friends and probably one or two enemies, the total list of people whom I'm sure will read this) consider not the list of unrelated jobs, but rather what that twisted arc says about the person who has performed all of them?
I am a person who is interested in connections. I am uncommitted to any particular discipline but rather committed to the idea that all endeavors have themes that relate them all together. These relationships make it possible to understand one discipline in terms of another. While in college I was an English major with an emphasis in Education and a minor in History, and besides getting the education that I was intended to receive in those two distinct silos of knowledge I got an unintended third education; that of the commonalities between the two. I realized we were having essentially the same conversation about literature as we were having about history. A talk about French poetry in literature class helped me understand the underpinnings of the French Revolution in a history class. I learned human effort is driven by a pretty standard set of common desires and the themes throughout history are fairly uniform. Certainly we need those who can mine the deepest depths of a single pursuit of knowledge but what use is that knowledge unless it can be applied across the board for the betterment of all? I found I couldn't possibly narrow my fascination down to just one thing, I am interested in how it all goes together.
Having that larger view plays out countless ways, but here is one way it played out for me: If I'm the guy who answers the phone in the office, I'm going to be the guy that gets calls about our website not working. Then I'm the guy that gets tasked with sorting out the problems because I can call our web developer the same as my boss can, and what is my job if not making my boss's life easier? Then I'm not only troubleshooting problems for our customers, I'm the front line for documenting issues for our web developer, which leads to spit balling ideas for making the site better, then anticipating problems before they happen, then being asked to beta test updates before they are implemented, then being asked to handle problems not only about how our corner of the web works for us but how it interacts with the organization's site as a whole, then learning how to write reports from that system to feed information to the top level executives, then being asked to attend regional conferences as our department's liaison, then being asked to advocate for changes to the entire system on behalf of the whole organization. That list can continue indefinitely, (or at least until I hit my limit according to the Peter Principal) with each link leading to more and more experiences, which leads to more jobs. Being able to make those connections, to see a bigger picture, to offer to take on another task, has lead to a professional habit of saying, "yes," of ending up in different places, of taking on different roles. My work as a office administrator, answering telephones in between photocopying and filing lead to being hired as the Information Technology Consultant for that department because I always was looking for the bigger picture and always said, "yes" to new tasks.
This leads me to the most troubling thing about being called a jack-of-all-trades, the implication that one is also a master of none. It's part of the idiom, and it's what people think even when their tongues stop short. It's a pretty limited view of what people can do or can know to assume that because someone's experience varies, that the nature of that experience is cursory or incomplete. Certainly tradeoffs in time and energy must be made in the sense that if I spend four years being a tech guy, then four years being a sound guy, that means that I didn't spend eight years being either, but I ask, when is spending four years doing anything every day considered inexperienced? The connection being under-appreciated is that here is someone who could spend years doing something and then have the versatility to pivot and apply those core skills to a different set of things that allowed him or her to be proficient enough to spend the next four years doing that. That predicts a great deal about one's ability to adapt again with that set of same core skills and added experiences under their belt for next time. This challenges a traditional professional model—some years of schooling for a trade that lasts a lifetime—but certainty there is room in the professions for people who have a broader view of things. I'd like to think that the trade I'm a master of is my own ability to acquire new skills and adapt to new circumstances and what could be more useful than that in this economy?
I am not asking for anyone to pity a jack-of-all-trades because frankly, we did this to ourselves. I'd never suggest hiring one when you otherwise would not, but if you, as a hiring manager, find yourself sitting across the interview table from one of these beautiful creatures, here's what I hope you'd consider:
Don't assume the applicant will get bored quickly
This knee jerk reaction is cause for most jack-of-all-trades' underemployment. Just because he or she has had many different types of jobs does not mean they require constant stimulation like a Labrador puppy. Varied job history has more to do with always being willing to take on new things when asked and considering all options when seeking new employment.
Ask what he or she sees as a common thread to their professional development
Often what comes across as disparate jobs is actually quite reasonable if you can get down to what the applicant sees as the thing that is truly interesting about a position. This may let you see the applicant in a different light or recognize something about your job that you didn't see before. It may be something intangible that a potential hire is pursuing, or a preference for certain tasks like working with third party vendors, or physical activity, or loving to travel that have nothing to do with the job title.
Go ahead and ask why there are so many jobs in a short period of time
Often times the answer might be about perfectly reasonable circumstances unrelated to professional development. Obviously "hard to work with" is the answer you dread, but if that doesn't seem to explain the person you see in front of you, a quick reference check should put that to bed. Often times leaving a particular job after a short while implies confidence in one's ability to find more work and not being happy with their current circumstance. If you think you can leverage that confidence in this position, then you might have found the right hire, if that seems like too much to manage, see what they have to say.
Give them an opportunity to make a case
A common problem a lot of jack-of-all-trades face is not being qualified for a position on paper, but having years of relevant experience performing exceptionally at very nearly the same job at other companies, probably because other managers were impressed with them and trusted they could handle jobs outside of their given trade. Another situation may be gaining all the requisite skills and experience over multiple positions during the course of their career, and yet not having a single prior position that is similar to the position at hand. Give them an opportunity to explain why their job experience is relevant and how they see what they have experienced stands in for a formal education. Keep in mind that they applied to your job because they felt qualified; they will certainly be able to offer a justification.
For smaller companies, don't assume you aren't competitive enough to keep them around
Let's be frank, being thought of as a jack-of-all-trades isn't considered an advantage in the professional world. If you are interviewing one, its because he or she applied to your company and wants to work for you. Take them seriously enough to fairly consider their application.
Consider why your positions descriptions are so rigid
You may have a department that is made up of one admin person, one specialist and one manager, but if you have people that collectively get the job done, why is it important that each only does the narrow job you hired them for? Be willing to consider a hire's full potential for a company and not merely what it says on the description. Be willing to consider an evaluation process that encompasses everything a hire can do.
Think about other positions
If this person isn't exactly right for the job you're hiring for, pass his or her resume around to others in the company. If you think this person has potential and think they would be an asset to your company but you can't put him in the job you have, see if others see potential.
Think about temp work or a consulting gig
Often times, jack-of-all-trades are perfect for those short term special projects, one-time build outs or as an extra set of hands on a project taking up too much of your regular employee's time. Those who are eager to work will gladly consider a temp assignment and you can expect much from a person who is used to jumping into new environments. This also gives you a chance to see how they interact with the company culture without committing to a long term hire. You can always offer them full term employment if you are impressed.
Consider combining smaller positions
If a company has several part timers or consultants on the payroll doing discreet functions, a versatile employee with a knack for seeing beyond his or her defined duties and who likes to work in various modalities might be the right person to consolidate two or three roles, creating efficiency and saving money. The advantage of having an integrated full time employee take charge of those responsibilities should be evident to managers who have to manage part timers or consultants. And YES, a single person can report to two managers. A jack-of-all-trades is exactly the kind of person who can handle that.
Advancement and lateral moves can be as engaging as seeking other employment
If you take on a jack-of-all-trades, you have to know that along with getting an employee that is dynamic and forward thinking, you've got someone who is going to be interested in and capable of more than than the duties assigned in one job. As a manager, you might consider always making him or her aware of lateral moves that can be made inside the company, to other groups, and to different departments.
Think long term
Granted you are hiring now for the position you need filled, but consider what advantages there might be to have an employee who can fill other roles in the future. An employee who can be moved, reassigned, given additional duties, asked to fill in for others on leave, take charge of new projects will prove invaluable. Most traditional professionals are hired for their training and experience upfront and then managers are delighted to discover an employee is also versatile after the fact. With a jack-of-all-trades, versatility is their upfront skill. They are the employee you'll want hang onto during downsizing and restructuring; they are the people whom you'd naturally track into management.
And don't call us "overqualified"
It's a backhanded compliment. I'm okay with, "divergent."

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