Why I Don’t Work With Difficult Clients (And Haven’t in 15 Years)
“Difficult clients” are often considered a regular part of business, something to tolerate or manage. But in my experience, difficulty is rarely about the client alone; it’s usually a signal of misalignment, unclear expectations, or leadership that hasn’t yet been fully claimed.
Over the years, I’ve found that when leadership is clear and boundaries are held, difficulty tends to disappear. This isn’t about avoiding responsibility or expecting perfection.
It’s about discernment, setting expectations, and choosing to work in relationships that support meaningful, transformational work.
It’s time to normalize not working with difficult clients. People often ask me how I handle them, whether on podcasts or in conversations with other business owners.
My reply is always the same: I don’t have them. My last one was over 15 years ago.
The work I do is deeply transformational and one-on-one. I want that time to be high value for them and for me.
As I mentioned, difficulty usually stems from misalignment, unclear expectations, or a lack of leadership presence.
I address this up front by setting clear expectations in both my sales conversations and my custom program agreements. I’ll even explain aspects of my work that they might find challenging or uncomfortable.
After several decades of this work, I can tell when I’m not the right fit. In those cases, I don’t make an offer.
If we decide to work together, we’re choosing each other and building the relationship from the first conversation.
Once the agreement is signed and the retainer is paid, expectation-setting continues through onboarding.
If boundaries are crossed, I’m willing to cancel the contract. Gratefully, I’ve not had to do that since I put these communication and legal practices in place.
Be clear on your boundaries and hold them.
Raise your bar, not your tolerance.
Catalyst Questions
Awareness of Patterns
When have I tolerated difficult or misaligned relationships in my work or life?
What patterns do I notice in those interactions? Were the challenges really about the other person, or about unclear expectations or boundaries?
How do I currently define a “difficult” client or colleague? How might that definition be holding me back?
Leadership & Presence
How clear am I about my own leadership presence in meetings, conversations, and agreements?
When have I unconsciously stepped back or over-accommodated, and what was the result?
What does it mean for me to “fully claim my leadership” in my work?
Boundaries & Standards
Which boundaries am I currently holding? Which ones am I tolerating or ignoring?
If I raised my bar instead of raising my tolerance, what would change in my work or relationships?
What would it look like to communicate my boundaries clearly from the very first conversation?
Discernment & Fit
How do I currently decide whether someone is the right fit for a professional relationship or collaboration?
When have I said yes when I should have said no? What did I learn from that?
What criteria could I use to ensure alignment before entering a working relationship?
Action & Alignment
What small steps can I take today to normalize saying no to misaligned opportunities?
How can I create an onboarding or expectation-setting process that reflects my standards?
How would my work, energy, and impact shift if I only worked with people fully aligned with my vision and approach?
To your easy and joyful success!
Stephanie
P.S. Let this settle and notice what is true for you. Every moment offers the opportunity to create the life you want with grace, ease, and joy. Let me know when you’re ready to explore possible next steps.
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DISCLAIMER: THE INFORMATION PROVIDED IN THIS POST DOES NOT CONSTITUTE BUSINESS ADVICE. NO RELATIONSHIP, INCLUDING ADVISOR/CLIENT, HAS BEEN FORMED AS A RESULT OF THIS POST.
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* Disclosure: Some of the links on this page are affiliate links. That means I may get a small thank-you commission (at no additional cost to you) if you choose to purchase a product from the mentioned company. I only refer you to programs run by people I know or have participated in, but please use your judgment to decide if this is right for you. If you would prefer that I not receive the referral commission, feel free to Google the company and purchase directly.
