Gaining Confidence in a Financial Advisory Business

You might know your craft inside out—but that won’t grow your business. Most advisors aren’t taught how to scale leadership, structure, or systems. Here’s how one found the support she didn’t know she needed—and thrived.

Allison Dunn

Table of Contents

Falling Into the Right Fit

Alex Lundgren didn’t plan to become a financial advisor. Her journey began in a small community bank where she was simply looking for a role with weekends off. But a shared desk with someone in the Investment Management Department changed everything. She started asking questions, “geeking out” over the Bloomberg terminal, and was quickly drawn into the world of investing.

“I literally fell into it, and I feel fortunate because I love what I do,” Alex said.

After years in the field and growing into her role at Tree City Advisors, Alex knew she was great at helping others set goals—but running and growing a business presented a different kind of challenge. That’s when she found Deliberate Directions.

Alex Lundgren, advisor at Tree City Advisors

Missing the Skills They Never Taught

When Alex first connected with Allison Dunn, it was through the 90-Day Planning sessions. She later did one-on-one coaching, then joined Whetstone, Deliberate Directions’ peer advisory group. For someone with deep technical knowledge and people skills, Whetstone offered something she didn’t even realize she needed: structure, scheduling systems, and leadership growth outside of finance.

“I know how to read the number on a Dow Jones stock chart. But nobody teaches you expansion, scheduling, or the things you never knew you needed to know about running a business.”

Solving Problems With Fresh Perspective

Whetstone quickly became more than a resource—it became a support system. The diversity of the group gave Alex perspectives she would never find inside her own industry. “It’s people you trust and can glean from. There’s no doubt. It’s valuable, confidence, and knowledge.”

When Alex felt stuck with scheduling issues at work, she brought it to her group’s Sounding Board. The advice she received—both tactical and interpersonal—helped her resolve the problem with new clarity. “It has been a turnaround,” she said. “Stuck isn’t working, so let’s find something else.”

Whether navigating a challenge or supporting someone else, she values the way members push each other with honesty, empathy, and experience.

Learning From Unlikely Places

One of the most powerful parts of Whetstone is the learning that happens outside the usual topics. “It’s like going down a wiki rabbit hole, but the real person is sitting there explaining it to you,” Alex said, reflecting on a Deep Dive where a member taught the group about blood donation.

The group constantly introduces new ideas—from operations to communication to mindset—that help her grow in ways that wouldn’t come up in the world of finance alone.

Even when the subject matter doesn’t directly apply, the takeaways are clear—and often surprisingly actionable.

Showing Up With Confidence

Today, Alex continues to thrive in her role, helping clients define goals and believe in what’s possible. And with Whetstone, she has the tools and community to lead more effectively behind the scenes.

She describes Allison as “someone who adds serious value”—and sees Whetstone as a rare combination of accountability, perspective, and encouragement.

“It’s a thoughtful group that was put together with you in mind,” she said. “So hold on tight, and use every bit you can.”

Not sure if you're the bottleneck? Find out in 2 minutes →

Table of Contents

CEO Bundle

Think strategically. Lead intentionally.

Get 10 free worksheets to help you lead like a high-performing CEO. You’ll also get bonus tips and coaching delivered to your inbox.

Get Bigger Wins

Talk about your biggest challenge or your greatest opportunity with coach Allison Dunn.

Achieve More with Less

In one session, discover how the top 1% of leaders create massive impact without burning out. Work smarter, scale faster, and stay ahead of your competition.

Reach Higher

Learn practical strategies the top 1% use to grow profits, build winning teams, and dominate markets.

Stop Guessing, Start Growing

In one session, gain clarity, uncover hidden opportunities, and leave with an actionable plan.

Coach Allison Dunn has helped businesses like yours achieve remarkable growth.

Your Most Important Meeting This Year

Speak with one of the top 1% of business coaches. In one FREE session, you’ll get:

✓ A clear path forward
✓ Strategies tailored to you
✓ The confidence to act