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How to Manage Clients From Contract to Final Invoice

Side hustles and freelancing have become a way of life, not work. They not only represent a way to earn extra cash, but also an outlet to explore — and profit from — interests beyond our day jobs. In fact, 27% of hustlers are more passionate about their hustle than their careers. And the number of freelancers is exploding like cockroaches blazing through the apocalypse, believing a multi-income stream life will be the norm.

As you can imagine, I’m violently excited because this means I might possibly have a future while sporting soft pants.

For the hottest of minutes, I consider abandoning my one-to-one client work. Thinking I could be one of those one-to-many course hustlers until I was reminded of the fact that swarms of people freak me out, customer service is a fine art I have no interest in navigating, and I do my best work when I’m collaborating with a client. Even if I’m drained because I’m giving my 100% to multiple clients on any given week.

The first decade of my career, I was the annoying client and I started the second decade of my career placating them. I was a managing partner in a New York digital agency where the only requirement for being a client was you paid your invoices on time. From the abusive clients who screamed into your ear on volume ten to the client who believed that much like an ER medic, agencies should be on call 24/7. They were telenovela dramatic, believing that we were curing cancer instead of convincing people to buy products they don’t need to live lives they weren’t sure they wanted to live.

Seven years ago, I went out on my own as a consultant and swore I’d never work with abusive, patronizing clients who willfully bulldozed through boundaries. Do you want to know how to score the clients that light you up? You manage them every single step of the way. Otherwise, they’ll manage you, and depending on the client that could range from dreamy to disaster. I’ve only had to fire a handful of clients because I methodically vet and manage them.

It starts with the business development process

  1. You’re fifteen minutes late for a thirty-minute call without a reason: I am not your servant; I’m your partner. Paying me for a service doesn’t give you trespass to disrespect me and my time because remember, you’re getting something valuable for your money. The best clients understand that your time is just as valuable as theirs.
  2. You speak jargon, not English: I’m a marketer and a storyteller, not a translator. I worry about people who assiduously parrot words that sound smart but mean nothing or who worship at the altar of a “guru.” The best clients question everything they know and they’re receptive to stepping out of their business self-help comfort zone.
  3. Your first words are “I don’t have a budget”: Money conversations are important because we’re trading service for payment. Although I believe you shouldn’t reject every client who can’t afford you, I don’t work for Fiverr prices. The best clients are open to being educated on pricing and the value exchange. They also know you get what you pay for.
  4. You want my cell phone number: There is absolutely no reason why a client needs my number. 99.999% of the time, it’s abused. Clients will expect you to always be available and a single text is often followed by a succession of DID YOU GET MY TEXTS? Again, we’re not curing cancer and the work I do (brand building, customer segmentation, and story strategy) does not elicit panicked texts in the middle of the night. The best clients respect your boundaries and know that they’ll get your best work because they’ve respected them.
  5. You hire an expert to fill a gap, but act like you know more than me: If you’ve vetted and hired an expert, trust they know how to do the thing you’ve hired them to do. Clients should absolutely ask questions and challenge consultants, but condescension, questioning an expert’s expertise, and insecure superiority complexes always give me pause. The best clients know valuable engagements happen through collaboration between a client who’s an expert in their business and a consultant who’s an expert in the gap a client seeks to fill.

And continues after you sign the contract

I have a tight onboarding process, which includes a designed PDF magazine that contains three sections:

  1. Housekeeping: This section outlines my office hours, how and when I can be reached, my tax paperwork, and details on file, project, and document management. As a practice, I do not follow a client’s file, project, and document management because of a. I’m not an employee b. my process works because I don’t have to waste time dealing with new systems and workflows for every client project. Also, I don’t believe in wasting time on unnecessary phone calls. Each engagement has 4–5 calls and they’re booked in one shot at kick-off. Unless we need to hammer out a miscommunication over email, I know wasting time chattering takes me away from the work that will move a client’s business forward.
  2. Process & Timeline: I repeat much of what I outline in the proposal and add detail so they know what to expect (from themselves and from me) and when to expect it every step of the way. On a kick-off call, I go through the process and timeline to ensure my client and I are on the same proverbial page.
  3. Client Requests: Every project of mine starts with a Discovery process. I have three worksheets and an asset request list for my client to complete before I get started on the project. I customize templates for every engagement, but the process remains the same.

And continues until the final invoice

Don’t talk around the problem — say what you mean. If a client hasn’t paid an invoice, let them know that you will stop work until payment has been made. If a client believes you should be on call, remind them of your office hours and availability (I actually build this into my contract due to PTSD from nightmare clients).

If problems arise, be a human

Get on the phone, talk through the problem without getting emotional or defensive, and offer solutions. Always come to the table with solutions because complaints get you nowhere.

In every client engagement, think about ways in which you can ensure your communication and work process are clear, concise, and collaborative.


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