EP25 | Jessica Williams

The Two Silent Killers Destroying Sales Careers (And How To Beat Them)

If you’ve ever felt like you’re faking it, or that your job depends on everyone liking you — you’re not alone.

Jessica Williams has been there too.

The founder of Just Williams, she spent over a decade in corporate banking before building a B Corp-certified sales and marketing agency. On paper, success. But behind the scenes, two silent killers were at work — impostor syndrome and the need for approval — nearly derailing everything she’d built.

Today, she runs a thriving business, trains thousands, and lectures on sales ethics. But her real story is how she learned to quiet those two voices that quietly destroy even the most talented salespeople.

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Our 5 Biggest Lessons

1. The Hidden Trap of Needing to Be Liked

The Challenge:

Salespeople often confuse being liked with being trusted. Jessica admits she did, too. Early in her career, she was a classic people-pleaser — saying yes to too much, afraid to push back, worried about being seen as “difficult.”

The Insight:

Trust and likeability aren’t the same currency.

“I can’t be liked all the time. “I don’t want to be disliked, but I don’t have a need to be liked. That’s not arrogance — it’s boundaries.” - Jessica Williams

She learned that chasing approval — from prospects, peers, or even her team — drained her energy and blurred her decision-making.

The Fix:

Set boundaries that protect your focus. Instead of measuring success by harmony, measure it by honesty.

Ask: “Do my clients trust me enough to tell me the truth?”

That question matters far more than whether they’d grab a pint with you.

2. When Confidence Turns into Imposter Syndrome

The Challenge:

From banking boardrooms to non-exec roles, Jessica found herself asking, “Who the hell am I to be here?”

She’d built a thriving company — yet the self-doubt was constant. The tipping point came when she realised she’d been appointed to roles “for the wrong reasons.”

“I put massive expectations on myself, and I was appointed for the wrong reasons. I let that get inside my head — and that’s a really dangerous place to be.” - Jessica Williams

The Insight:

Imposter syndrome in sales isn’t humility — it’s self-sabotage disguised as modesty. It’s the internal voice that whispers, you’re not ready, you’re not qualified, they’ll find you out.

The Fix:

Jessica hit pause. She got therapy. She found a coach. She quit what was draining her confidence. And she made a conscious decision to rebuild from the inside out.

If you’re leading a team, take note: the reps who appear confident but quietly overwork or over prepare may not be “high achievers” — they may be fighting imposter syndrome alone.

3. The Reflection Habit That Rebuilds Resilience

The Challenge:

When Jessica’s business hit turbulence, she realised her default move was to grind harder — not smarter. Journaling became her reset button.

The Insight:

“You can’t exert your energy trying to keep everyone else happy to your own detriment.” - Jessica Williams

Self-awareness, she argues, is the highest form of sales intelligence. When you journal, coach, and reflect — you spot your patterns before they wreck your confidence.

The Fix:

Jessica now treats reflection as non-negotiable.

She journals, runs (13 marathons and counting), and surrounds herself with people who challenge her thinking.

It’s the same principle that separates top salespeople from the rest: radical accountability.

You can’t lead others until you’re willing to coach yourself.

4. Spotting the Silent Killers in Your Team

Imposter syndrome and the need for approval are different, but they often feed each other.

Here’s how to recognise both before they tank performance.

Signs Your Rep May Have Need for Approval in Sales:

• They avoid asking hard questions in discovery.

• They over-apologise when challenged by prospects.

• They confuse friendliness with trust.

• They crave constant praise or reassurance.

• They hesitate to disqualify bad-fit opportunities.

Diagnosis: Their desire to be liked overrides their duty to sell with honesty.

Possible Signs Your Rep Is Suffering from Imposter Syndrome:

• They overprepare for every call and still feel “unready.”

• They downplay achievements or deflect praise.

• They overcompensate by working excessive hours.

• They avoid leadership exposure or high-visibility projects.

• They freeze up when selling to senior stakeholders.

• They struggle to celebrate wins — because they never feel “enough.”

Diagnosis: They’re not lacking skill — they’re lacking self-belief. And unless addressed, that self-doubt turns into underperformance.

5. Coaching Your Team (and Yourself) Out of It

The fix isn’t a pep talk. It’s coaching that builds self-awareness over self-image.

Help reps see that their value comes from competence, not validation.

Coach them to reflect on what they control: preparation, honesty, follow-up, and learning.

And remember — you can’t coach confidence into someone if you’re still chasing approval yourself.

Final Thought

Jessica’s story is proof that sales performance starts with emotional fitness.

You can’t close deals if you’re busy closing off the parts of yourself that feel unworthy.

The cure to both imposter syndrome and approval addiction is the same: clarity.

Clarity about who you are, what you stand for, and what you bring to the table — even when no one’s clapping.

If you see yourself or your team in this story, don’t wait until burnout hits.

Get coached. Build reflection habits. Reconnect with your purpose.

Listen To The Full Podcast Here:

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