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.



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