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The Resilient Consultant: Five Steps to Minimizing Client Failures

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The following article is an extension of The Resilient Consultant:  Five Steps to bounce back from failure.

It’s a logical spin-off to cover what I believe to be an extremely vital topic, which will most assuredly help you obtain some perspective.  It will provide five key steps to minimizing future freelance failures and protect your personal brand in the process.  I’d like to point out that these steps go beyond a standard methodology for managing a freelance gig.  There are plenty of materials out there that cover that space, so you won’t find that here.  What you will find are proactive steps an individual can take across the full range of the sales life cycle, from pursuit to execution, that better position freelancers for success.


However, just like any other methodology, the following guidance will not guarantee that you never encounter a bad freelance opportunity again.  In fact, I suggest that you accept the absolute certainty that you will be confronted with bad gig at some point, so please save yourself the suspense.  Some of the most dramatic personal growth I’ve achieved in my career has come directly from bad projects.  Don’t be afraid of the challenge; embrace it.  Just be mentally prepared to take on anything and get ready to adapt.

The real value from this piece comes from helping freelancers understand that they do have some control over their destiny.  I say “some” because there are certain elements that are quite frankly outside of anyone’s control, such as client timing and budget availability.  But by melding the following guidance into your existing freelance routine, it will help avoid client difficulties, and increase the likelihood of overall success.   If your goal is to achieve some semblance of longevity in your freelance side hustle, please take these steps seriously.  Although a few of the steps may appear to be “common sense” at face value, the old adage of “common sense does not always equate to common practice” could not be a more apt description.

Without further ado, here are the

“Five Steps to Minimizing Client Failures”:

1. Become a Professional Skeptic

Let me be clear:  Becoming a professional skeptic does not mean an individual should act like a crotchety-old cynic who doesn’t believe in the “system.”  A professional skeptic is one who consistently asks the right questions in order to ascertain exactly what will be expected for a particular project and clearly understands the type of environment to which he will be exposed.   A professional skeptic always demands more information as he understands the necessity to be overly prepared and totally aware of what he’s getting into.  In some cases, even a seasoned freelancer makes mistakes.  But… rest assured, he will always consider the following:

  • What is the project scope, timing, cost and quality expectations?
  • Have prior freelancers had successes or challenges worth noting?  If yes, what were some of the lessons learned from those experiences?
  • What are the logistics of the assignment?  Location, communication expectations, start dates, vacation constraints, etc

1b. Questions a professional skeptic would ask of themselves before committing to ANY freelance gig:

  • Do I really have the right skill set the client is looking for?
  • Is this opportunity in line with my side hustle aspirations?
  • Will this gig provide me with the right exposure?
  • Is there anything that feels “off” to me about the opportunity?
  • Do I confidently feel I can work with the personalities I know I’ll be working with?

2. Look Before you Leap

Beware, since sometimes freelance opportunities can be presented in a much more positive light than they really should be.  Once you’ve received responses (from existing side hustlers, if you can, or indirectly from platforms like UpWork) to the questions above, be sure to do your homework.  Inquire within regarding fellow freelancers and how they did with a potential client you’re considering working for. Candid conversation may lead to uncovering any significant issues with an opportunity, if any should exist.  Remember, the focus here is not to go out of your way to find something wrong.  You’re just trying to do some homework,

The important thing here is to trust but verify.  Always look before you leap.

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3. Set Expectations

Once you’re on the verge of landing a gig with a client, be sure to set expectations early on.  Do this during your early interviews with the client!  If you’re an expert on SOMETHING, flex that skill and let the client know your strengths and exactly how you plan on attacking the work.  Be thorough, yet concise.  However, if you’re not an expert in the space you’re pitching on, don’t pretend to be.  Ideally, you always want to align your experience with the exact client need, but most freelancers know that that does not always happen.  Sometimes there’s just no one else around and you raised your hand first and suddenly you become “the guy” or “quasi-expert” by default.  Unfortunately, it happens.  Make sure your client is aware of this from start to finish, so that they never lose sight of the fact that you’re operating in a less then optimal situation.

Why? The client will eventually sense or outright notice that something is off.  In some cases, the client will accept the learning curve as long as she is still receiving the overall value she needs.  In others, the client may accept nothing short of a genuine EXPERT, in which case you should pull yourself from the opportunity because the last thing you want to do is present yourself as something you’re not, then be given a poor performance review (which stays with you for the life of the platform you’re using) because you did not perform as an expert would.  Be candid and clear with what you can and cannot do.  Set expectations so there is transparency in every step of the gig.

4. Build Relationships

A surefire way to anchor yourself within a new opportunity is by building relationships within your team (if you’re working with one) and obviously with the client.  Share your knowledge, let them know what you’re capable of and, most importantly, connect with individuals on a personal level.  Learn about their families and hobbies; understand what makes them tick.  This insight will prove invaluable over the long run as that very bond will foster better communication and just make for a more pleasant working environment.

It takes time to cultivate relationships regardless of whether they are a client or not.  As a freelancer, there is some control over investing in networking time, so do it!  This is vital early into any freelance gig to build morale and trust.

Client interactions vary greatly, but the important thing is always to be available and responsive.  I’d like to stress responsiveness as there’s no quicker way to turn off a client than by not getting back to her in a timely fashion.  It’s the foundation upon which trust is built.  It’s very difficult building a relationship with a client if she senses you don’t have her back at all times.  As the relationship developments, so typically do personal interactions.  A prudent approach would be to maintain a professional distance; however, don’t be afraid to provide the client with a glimpse into your personal life (if she seems remotely interested in it, of course).

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5. Keep Your Eyes Wide Open (Watch, Listen and Learn):

An important tool in any freelancer’s toolbox is his ability to articulate ideas.  In other words, talk.  As you might expect, talking is crucial during the sales cycle, but it’s just as important after the work has been sold.  Moreover, once you’ve entered into the realm of delivering work, it’s even more crucial that you demonstrate an ability to listen.

Always listen and reaffirm what you hear during client interactions.  The greatest mistake a freelancer can make is assuming that he knows what the client needs before she explains her requirements in her own words.  In most cases, the client will flat-out tell you exactly what she needs.  Just listen!  Hubris can really take hold of a seasoned freelancers if he allows it to.  Don’t fall into that trap.  Listen to all relevant information to ensure you’re delivering what’s really needed at all times.

As a gig progresses, freelancers will often be exposed to different facets of the client’s business.  This exposure is incredibly important not only to the current project at hand, but also to future opportunities.

The important takeaway here is to be cognizant of your surroundings at all times.  So don’t be myopic!

Become a professional skeptic, look before you leap, set expectations, build relationships and finally…keep your eyes wide open.

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