Life On Contract: How To Fail At Contracting Regardless Of Skill

I believe higher quality learning happens from sharing failure than from sharing stories of success. If you have set your mind to living on contract, I present this cheat sheet of some of the most simple and effective ways to muck it all up that have surprisingly little or nothing to do with your technical skill, knowledge, or even deliverables.

The previous installment of Life on Contract discussed how one might find clients as an engineering contractor or consultant while also taking a bit of time to pull apart the idea of whether life on contract is appropriate as opposed to, for example, bootstrapping a business instead. Assuming you are set on working as a contractor, let’s talk about what happens after you have found a prospective client (or perhaps more likely: after they have found you.)

WARNING: this article features an utter lack of success tips and tricks. Partly because those can be found in any seminar or business self-help book, but mostly because I do not have a foolproof recipe for success, and cheat codes to unlock easy mode still elude me. But I have witnessed (or committed) and reflected on many excellent ways to fail at contracting; or at the very least succeed in not being invited back.

Just because I won’t be sharing success stories doesn’t mean success has no learning value. Got a success story, or a better way to fail? Tell us about it in the comments!

How to Fail (or at Least Not be Invited Back)

The kind of contracting or consulting I’m discussing is mainly about solving problems. Put another way, I have found that successful contracting is mostly about taking problems away, and making your client’s life easier. They should see you as money well spent.

Failing at contracting is all about making life harder for your client. Barring actual negligence or incompetence, there are plenty of ways this can happen.

Talk the Client Out of Wanting You

Clients will have problems, and one or two of them will happen to be ones they want you to solve; that’s why they are seeking expert help. Their problem may be specific — “we need someone to convert these from through-hole to surface mount” — or it may be something broader — “we’ve been making these in our garage but need to make them faster and cheaper, how do we do that?”. There’s always a clear need, even if the client is having trouble articulating it.

quote-not-helping-communication-causes-failureThe simplest and most efficient way to fail is to nip the whole contract in the bud. A client decides against hiring you when they don’t see you as an added value. The reasons for failing in this way (again, barring negligence or incompetence) always come down to a tragic failure to communicate. You may genuinely fail to understand the client’s needs, you may fail to communicate to them that you do understand, or you may otherwise fail to present yourself as a viable solution to any of their problems.

Let’s examine some excellent and common ways to make a client decide against hiring you:

  • Don’t speak the client’s language. You don’t know their terms and don’t understand anything about their industry. If they are a print shop, you have no idea how print shops operate or do business. If they are artists, you speak only in engineering terms and jargon. Being unable to relate makes clients feel that they are out of their depth, or that you’re just from a different and less-compatible world. It ensures that explaining things always takes maximum effort, and a client is never really certain you’re actually on the same page. Avoid this by studying the client’s industry and terminology.
  • You aren’t on the same wavelength. If a client is focused on wanting to understand how to best do a small in-house production run versus offloading it to a contract manufacturer, then focusing on specific yet irrelevant details like the finer points of injection molding, or KiCad vs Eagle, can lead to failure. You’re on the same topic, but not at all in tune to what they actually want to do or know. Avoid this by taking time to ensure you understand what advice the client is actually seeking, even if they haven’t asked for it in the most direct way.
  • Be a Magic 8-Ball whose only answer to every question is “it depends.” If you can’t provide direct answers to most questions, then regardless of how correct your waffling is you’re probably not understanding what the client needs from you. In all likelihood, what your prospective client actually needs is an understanding of a situation or process they are facing. Put another way, they don’t need exact numbers and you’re not being asked to commit to a deadline; they’re asking because they need to understand what has to happen and when, so they can budget and plan. You are being asked because they want someone who has been-there-done-that to “get” what they are doing and be a guide. Waiting patiently while prospective clients ask you question after question (to which every answer is some form of “it depends”) is an excellent way to talk a client out of contracting you, because it makes it clear you won’t be making their problem or uncertainty go away.

The best thing about these methods of failure is that they don’t require all that much effort. In fact, simple inattention or inaction is most of what’s needed. So long as you’re not actively trying to help communication in an initial meeting, things have an excellent chance of going wrong all on their own.

Give the Client Second Thoughts After You Get the Contract

An engineering contractor is not normally involved in a client’s day-to-day business operations; at least, not in the kind of contracting and consulting we’re talking about. Your work and the expectations from you — both explicit and implicit — are different from those of an employee. Failing to meet those expectations is the key to making your client wonder if contracting you was a mistake.

For example, let’s say a client has a product and you have been hired to optimize the board layouts and reduce PCB costs. Showing up on the first day with open hands and an open heart, brightly asking “Okay! Where do you want me to start?” is a great way to make your client think twice about hiring you as an expert; someone who was supposed to know more than they did themselves.

In addition to whatever you were officially hired for, you need to be money well spent. If you are not actively solving or removing problems in some way, then you are probably not clearly adding value. You may even be making your client’s life harder instead of easier.

It may remain unsaid, but as a contractor or consultant you are at least partly being hired for your judgment. The less effectively you wield your judgment, the more your client will start to think you were a mistake. Here are some great ways to ensure that happens.

  • Constantly halt what you’re doing with “how do you want me to…” questions for your client. The more this happens, the more likely you are to plant second thoughts in the mind of the client. Asking this for what seems like every conceivable detail, and at every possible fork in the road and failing to gather information you need up front will raise red flags. It’s bad form to be seeking approval and direction for issues you should be able to handle yourself if you actually understood the client’s needs and problem scope. This behavior makes sure that the problems stay front and center, and very much still on the client’s plate. As a bonus, you will almost certainly appear to be “winging it” instead of having experience and a plan.
  • Be overly focused on details unrelated to your client’s actual needs. If your client thinks you’re focused on irrelevant details, they won’t see that your work has any value. If the details in question actually are relevant (but perhaps not obviously so) then you must ensure your client understands the relevance. You may be extremely knowledgeable, but that doesn’t mean you can’t spend the first weeks of a contract installing and minutely benchmarking every possible different database backend to find out which one yields marginally better performance, only to find out that your client isn’t actually willing to change database software and (shocker!) frankly doesn’t see how a marginal improvement could possibly be worth all that effort when they just wanted you to integrate a live stock count into their e-commerce site.
  • Be unable to actually get something done. Having a poor sense of proportion can hobble your measurable progress. If firmware on a given microcontroller architecture is 90% working, throwing it all out to begin again the instant a newer and faster part comes out is a great way to fail. There is such a thing as smart people who are unable to get a job done. In the business world where everything is a trade-off because everything costs in one way or another, clients are well aware that there is “good” and there is “good enough.” Does a solution do the job? Can it be achieved within the budget and time allowed, without painting you into an unacceptable corner? If so, then that’s Good Enough. Smart, knowledgeable people who can crank out high-quality work quickly may still never actually get anything done because they constantly take off like a heat-seeking missile after the latest and greatest, or obsess over details irrelevant to making something work.

Have you managed to get a job done despite all that? Don’t worry, there’s still a chance to fail!

Make Sure You Don’t Get Invited Back

Life on Contract: How to Find Clients as an Engineering Contractor matched my own experience, particularly in the observation that a good portion of your work will come from referrals. That means that if you really want to make a go of life on contract, leaving a client feeling like you didn’t really add value is a really great way to snatch failure from the jaws of success.

quote-work-that-nobody-knows-happenedIf your client doesn’t feel that you were worth the money, or that you were just too hard to work with, you won’t be invited back — either to more work, or to conversations that begin with “who can we talk to about…”

Here are ways to tarnish the shine of a completed project:

  • You didn’t do things when you agreed they would be done. Failing to keep deadlines or to report on your progress is a great way to get ejected from a client’s contact list. If your estimates and progress reporting become known for not being reliable, even if your work is of outstanding quality, you may simply be judged Too Hard To Work With. As covered in Life On Contract: Estimating Project Time, estimates are important for planning and budgeting both time and money. Making sure yours aren’t reliable is a great way to cause cascading disruption in other people’s work every time it happens.
  • You didn’t take (or make) time to polish the results of your work. Finishing touches on something go a long way to communicating value and the work that went into it. Whether it’s software or hardware, you may know it inside out by the time you’re done but most people won’t be seeing it as a raw expression of function. Leave your work looking like a hack job, and you’ll be thought of as one.
  • Let the value you added go unnoticed. There is a somewhat cynical saying about work that no one knows was done: it might as well not have happened. As a contractor there will always be some pressure to show you were worth what you charged. You may be making tremendous progress and adding excellent value, but if your client is unaware of any of it, they won’t know you were responsible for that value. Modesty may be a virtue, but also another way to fail at getting called back.

All of this type of behavior will ensure that if you find a client, they won’t hire you. If they do, they’ll regret it. And if your contract completes, they won’t want you back. Since a good chunk of work will come from people knowing you as “the person who knows about that stuff and can get it done”, falling into these bad habits will virtually guarantee you are free from clients.

These are of course from my own observations in both the working and hiring ends of contracting, but they are still only my own narrow slice of a wide and varied field. Have you got your own success or failure stories to add or admit to? You know you do; share them in the comments.

32 thoughts on “Life On Contract: How To Fail At Contracting Regardless Of Skill

    1. Sometimes more than one person contributes to an article series. With the exception of the previous article in Life on Contract (“how to find clients” which is the only one to go without a specific person’s name, to my knowledge) whoever authors a particular article goes right under the title.

  1. Yes communications is very, very important. However communication is a two way road. Some clients are incapable of expressing what they want. This is due to many factors. Uneducated, impatient, lazy and unreasonable.

    1. And that’s where you lose them. The clients are not uneducated or lazy – they’re already running a business. Never look down on them, for any reason; not under your breath, not rolling your eyes, not complaining to your drinking buddies over beers. Seriously, a condescending jerk is not someone anybody wants to hire.

      As the engineer, you need to ask the right questions to elicit a response you can both work with. You may have to ask the same question eight different ways, or ask questions tangential to their point until you can pry open the real problem underneath. It’s not easy, but that’s why they need help; because it’s not easy.

      1. Agreed! If you assume effective communication is the client’s responsibility, they’ll find someone else that they can communicate well with. Or, they’ll fail spectacularly. Either way, you’re not getting paid.

      2. “they’re already running a business”

        This may come as a shocker to you, but most people running stuff are terrible at it. See: Dilbert, Office Space, etc. for pop culture references to what we’ve all experienced. That’s why we went indie, to get away from that idiocracy.

        “but that’s why they need help; because it’s not easy”
        No, 9 times out of 10 they need help because they dug themselves into a giant hole and they need someone to engineer their way out. Otherwise their in-house talent would have it all covered.

      3. Of course everyone should be mindful of the actions, mannerisms and words. Because someone is already running a business doesn’t necessarily mean the are educated, or aren’t lazy. Even if the are educated doesn’t mean they aren’t ignorant of/in a subject that’s important to their business. I guess those who can navigate those hazards successfully every time are the best of contractors, all else being equal.

  2. This is a great article. I might add “Leave the scope or statement of work vague.” That way neither you or the client know what you are doing. Also “Immediately forget the purpose of the contract and take the client an entirely different way.” Sadly I have been guilty of all of the above and these as well !!

    1. That’s a good one! Like having a meeting, discussing and agreeing to things, getting everything set, then after wrapping up someone pulls you aside with a tap on the shoulder (or you pull someone aside) to change the whole scope of the job that was just discussed…

  3. I have worked as a contractor on and off in the past and, in my opinion, the most difficult part is sorting out the taxes. In part, this was a problem because I did not want to pay an accountant so I had to learn everything by myself. It was a valuable lesson but it also showed me how taxation is an obstacle for small businesses.

    In the end, I ended up running into some taxation rules that were in a bit of a grey area (this was in Canada, btw). After talking to other contractors, I realized they were all taking advantage of this rule. An accountant also told me it was safe to proceed and take advantage of it. Yet, when I presented them with the wording of the rule, it was pretty clear that what they were doing could be challenged in court. The accountant just told me to take advantage of it and lay low because everybody else was doing it. Keep in mind that, at the end of the day, if you get audited, you are the one responsible for your taxes even if you paid an accountant to do them for you.

    This experience left me pretty distraught. In the end, I decided that paying more in taxes was worth my sound sleep at night and I did not take advantage of the contentious rule. After this experience, I decided running a business was not for me.

      1. I have done work in some large contracts. I am talking specifically about two taxation rules in Canada that are often abused: 1) SR&ED credits ; 2) The rules used by the CRA to establish whether you are a contractor or an employee. When it comes to the latter, whether you like it or not, the CRA (our IRS) may decide that you are an employee instead of a contractor and the rules used to do so are not black and white. If you come under scrutiny, the penalties are severe.

  4. “Constantly halt what you’re doing with “how do you want me to…” questions for your client.”

    I would strongly disagree with this statement. I worked for 20+ years as a contract scientist/programmer on a total of 5 contracts. The last was 6 years followed by another 2 years with the company that acquired them. I generally did whatever I thought appropriate with little or no supervision. I never had any problems because if there was a management level decision I would locate the appropriate manager, explain the issue and options and ask for their decision. The key is to understand the difference between policy and procedure. You’re supposed to know procedure. Policy is a management prerogative.

    But I was also a “brand of me” level contractor. I didn’t look for work. It found me by name.

    The ultimate guarantee of failure is to conceal problems until they can’t be fixed. If I encountered an issue which might slip the schedule I went to management immediately and explained the problem and suggested solutions. I worked in an environment where the delivery date was set by external requirements. Not on time, not worth much, if anything. Sometimes it turned out not to be as big an issue as I thought so the client got what they had sked for in the first place.

    1. I think I should note that I did not choose to become a contractor. I got laid off in ’91 and after 5 months found a contract gig. I voluntarily left after 3 years when they had another lay off coming. The next gig had a layoff the day after I started. On that gig I didn’t talk to my boss for almost 3 months. He would just wave to me as he passed my office. I finally cornered him, appropriately in his corner office and asked him what I was supposed to do. “Just make sure no one is yelling at me.” was his reply.

      1. Finally, a subject I can speak on; Nature of some industries. In particular – Information Systems. I switched from always being in R & D Development as an Employee, to Contracting in 1995 (16 years in, for another 15 years) – because companies changed their models from direct hiring to project basis. Most had no idea how to manage Contractors, and didn’t care. You are most times used as cannon fodder – unless you get into a really good company. If there is something that can be blamed they use the Contractor for it. Get everything in writing that you can to protect yourself from the Client and not get booted from your placement company. In most cases I find the Client just wants it to be done – they don’t want to know how, they only want to know how long, and then they usually subtract 40% from that time – and they don’t want your opinion. And are usually unwilling to purchase any extra tools that are required for development (I know – don’t ask me why). So unreasonable time frames without a proper analysis is usually how things are done, no business plan, no technical plan, and no sign off. If you are lucky to turn a pile of sh*t into a rose garden – then they keep you on for the next project. And the part where you make sure things don’t escalate to your Manager – I have seen that a lot.

        1. These bring up a good point. There are different kinds of contracting.

          Some are employees in all but name, but the kind I’m familiar with is a form of self-employment and which I tend to prefer to call consulting. I haven’t personally experienced any consensus on the definitions of contractor vs consultant – people have used them interchangeably more often than not – but maybe it’s a regional thing.

          In Canada for example, Engineering is a capital-E word with a specific meaning. In the USA the meaning is broader. So maybe there’s some allowance for regional differences with the words and terms.

          1. I didn’t think of that. Contractors here in the U.S. for things like IT are People that are placed by a service. Consultants can mean individual placement or as a worker for a large company that gets placed. For example: I worked for Hudson, which is an offshoot of Monster (back then) as a placed Contractor. But I worked also as an employee of Manpower as a Consultant into a large company (Cooper Tire). So maybe it’s just whatever they want and they are used interchangeably? Either way, it depends on who pays you in the end, I always worked for a service that did the payroll – thus getting a check bi-weekly. As a Consultant that is a single entity you need to be a sales person, a payroll person, insurance person, etc. AND you get to deal with the target company pulling the 30,60,90 days receivable bull. I prefer the weekly check – the money is less, but you are really paying for the representation and the paperwork. If there are issues they can deal with it. Much better.

          2. One thing I did notice is that in the old days in IT, you had Programmers, Programmer-Analysts, Analysts, Sr. Analysts, Sr. Programmer Analysts. Now it’s just “Developer” for the most part. And the people do ALL facets of the process from writing business plans, technical plans, test plans, resource planning, programming, actual testing, fail-back plans, switch over, training – everything. That’s a big difference to the old days, and really cuts out a lot of people that can’t made the grade – especially in the Contractor area, very cutthroat. I bet for every ten people I have worked with in the industry over 30+ years – only about two know what they are doing and are competent – people you can ask questions of, and that’s if you are lucky.

  5. While it’s out of the scope of this article, often laborers will find themselves being considered contractors. A friend of mine who had to be absent from his job because of cancer treatment found himself without of a job post treatment.. Being older with few marketable skills he was left scrambling for a decent job. When he was describing a job he was considering , it sounded like the business he would be working for would consider him a contractor, not an employee. When I tried to explain to him the pitfalls of that along with another concerning issue, he would me he had someone helping him out on that in the matter, I took that as code to drop that a matter and another, so I did. Turns out I was correct on both issues. He was considered a contractor. My friend wasn’t estimating/paying income tax quarterly or paying self employment taxes. On the other issue his disability income was endangered. Only by dumb luck he averted disaster. I blame it on an US primary education system that whose intent is to crank out worker drones, willfully kept ignorant.

  6. I agree with most of the stuff written in the article, but, there is a few caveats.

    Asking your client often and soon is a good idea, most of the time they would say “don’t care”. However, if you assume so, you are in a world of hurt. Make sure you have a written track or someone else nearby to confirm the words. It only saves arguing, doesn’t matter for legal.

    Speaking of legal, account for a lawyer. Just write down the number, most of the time it will be trust based and you SHOULD build trust. You will eventually get paid, disputes will be settled over a cup of coffee, deadlines will be prolonged. But once in a while you’ll find the sue-happy client or someone not willing to pay (because of “market conditions”).

    Changing requirements – it’s the only constant. It’s up to you as a contractor to figure out future needs before they come into play. For example, a second guy working alongside you is a good assumption, this goes way beyond documentation. And it’ll probably be up to you to find that guy (/girl).

    Recommendations are double-edged. If you did a good job for a very good cost ratio you will probably not get any, as the contractor will try to ‘snatch’ you for the next project before the competitor. This is signaled by a low-cost maintenance project for the current product as he/she prepares for the next project. You are probably already accounted for in the next budget. I’m trying to say: if you see they are stingy with the current project but pitching for the next one, asking for your feedback, take that as a sign they might want to work with you. Since budgeting is a bloodbath in most companies they will try to get the lowest rate they can.

    Money: in these 2 series I’ve never seen any mention of it. Contracting is high-risk and high-expense. Ballpark: if you value yourself at 2x internal employee rate (and deliver at least 20% extra) it’s ok. For internals, they have to deal with legal, insurances, hiring fees, perks, bonuses, vacation time, taxes, lawyers, severance. Now you have to deal with all of that.

    Not a foolproof plan but don’t kid yourself. It’s bloody and you will lose sometimes. But if you are structured, you win flexibility and/or money. You should be self-dependant for at least 1yr and know all the right people to succeed. And expect to either stay on the sidelines or go back to a ‘normal’ job at any time.

    But I agree with communication requirements and seller’s mentality. You have to be able to sell yourself and see what the client is trying to achieve before you actually set foot in their office.Last year might’ve been ‘savings’, this year IoT, next year ‘market stability’. Make sure you write a plus to their balancing sheet and everything is golden.

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