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    Home»Leadership»Heart First, Hustle Always: Real Lessons for Loan Officers Navigating Leadership
    Leadership PeerTalk

    Heart First, Hustle Always: Real Lessons for Loan Officers Navigating Leadership

    A collection of real-world lessons on how to lead with intention, empathy, and consistency in the lending industry.
    By Ashley Jackway
    May 19, 2025
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    Ashley Jackway, heart first, hustle always

    Part 1: Transparency Over Perfection
    How honest communication builds lasting trust — even when the news isn’t great.

    If there’s one thing I’ve learned in this industry, it’s that leadership isn’t a destination — it’s a collection of small, intentional choices. Over the years, five ideas have become central to how I show up as a professional and a person:

    1. Transparency Over Perfection
    2. Setting Boundaries Is a Leadership Skill
    3. See the Broker, Not Just the File
    4. You Can Have It All — Just Not All at Once
    5. Lead With Heart, Follow With Action

    Each of these lessons has deeply influenced how I lead, connect, and grow. They’ve guided me through uncertainty, helped me embrace change, and kept me steady under pressure. While I may not claim the top of the industry, I’ve carved out a space I’m proud to stand in — one that reflects my values, my resilience, and my purpose. To me, that’s its own kind of success.
    Before we dive into these lessons, here’s a little context about my journey:

    I started my career on the marketing side of a wholesale lender, eager to understand how the business really worked. I wasn’t afraid to ask questions, stay late, and learn fast. That mindset took me into sales, then into hard money lending, and eventually back to wholesale lending — each step offering a new lens on the lending process and what brokers face every day. When I returned to wholesale lending, I brought with me more than experience: I brought perspective, empathy, and a stronger sense of purpose.

    In this series, I’ll unpack each of the five ideas that continue to guide me. We’ll start with the one that, in my experience, has the power to transform how we do business:

    Transparency Over Perfection

    There’s something powerful about being honest — even when it’s not polished. Even when it’s not perfect. In fact, I’ve built my career on it.

    In a fast-paced, high-stakes industry like lending, the pressure to be perfect is real. We’re expected to have all the answers, hit every deadline, and make every file look effortless. But here’s what I’ve learned: chasing perfection isn’t what builds trust — transparency does — and that honesty builds trust faster than any pitch ever could.

    Perfection may impress people. Transparency connects them to you.

    When I first stepped into a leadership role, I thought I had to prove myself constantly. That meant long nights, never saying “I don’t know,” and always appearing in control — even when I wasn’t. It didn’t take long to realize that pretending to have it all together wasn’t helping anyone, especially not my team or my broker partners.

    So I shifted. I started being honest about challenges. I explained why a condition was delayed instead of brushing it off. I started giving real timelines instead of the ones I thought people wanted to hear. I let my brokers in on the process — even the messy parts — and they responded with more appreciation and trust than I ever expected.

    That’s when it clicked: people don’t want perfection. They want someone they can count on.

    Transparency isn’t about oversharing or exposing every flaw — it’s about setting realistic expectations, owning your role, and communicating with clarity. It means having the tough conversations when guidelines shift. It means saying, “We can’t do this exactly as you hoped, but here’s what we can do.” And most importantly, it means always telling the truth — even when it’s uncomfortable.

    That honesty builds something far stronger than surface-level satisfaction: it builds trust. And trust is the currency this industry runs on.

    One of the things I pride myself on is the long-standing relationships I have with my brokers. These are people I talk to weekly, sometimes daily. They rely on me — not just to get loans across the finish line, but to be their sounding board, their advocate, and their strategic partner.

    I’ve learned that the best way to take care of them is to communicate clearly and often. That means I don’t ghost them when things go sideways. I don’t promise what I can’t deliver. Instead, I keep them in the loop, I hear them out, and I collaborate to find solutions.

    Because here’s the thing: when brokers feel heard, seen, and supported — even in moments of disappointment — they come back. Not because everything was perfect, but because you were honest and present.

    In the early stages of my career, I was always trying to prove myself. Now, I focus on partnering. I’m not here to impress people with how perfect I seem — I’m here to empower them with how dependable I am.

    That’s the energy I bring to every deal, every conversation, every challenge. I’m not afraid to admit when something needs work. I’d rather be upfront than overpromise. And in the end, that mindset has earned me more trust, loyalty, and long-term success than chasing perfection ever could.

    Let me share a moment that really stuck with me. A broker came to me with a file for a long-time client — a first-time investor who had poured everything into securing their first property. Midway through the process, the appraisal market rent came in lower than expected, throwing the entire structure of the deal into question. Emotions were high, and the pressure to make it work was even higher. Instead of dodging the tough conversation or scrambling to cover it up, I called the broker right away. I walked them through the appraisal, explained what it meant for the loan, and laid out two realistic paths we could take to keep the deal alive. It wasn’t the call they wanted — but it was the one they needed. Because I was transparent and came prepared with solutions, we were able to shift the structure, realign expectations, and move forward. A few days later, we closed.

    That moment didn’t just save a deal — it strengthened trust. The broker later told me that my honesty, even in a moment of tension, was what made them feel truly supported. That’s the kind of trust that turns into loyalty — and that no interest rate can compete with.

    If you’re in this business — or any business — and you’re trying to be everything to everyone, I see you. I’ve been there. But let me offer you this: the most powerful thing you can be is real.

    Be clear. Be direct. Be human.
    Perfection might look good on paper, but transparency builds legacies.

    And in this industry, that’s what truly matters.

    Just to be clear — transparency isn’t about being negative or dwelling on what can’t be done. It’s about being real. It’s the courage to confront challenges directly, paired with the professionalism to communicate with clarity, honesty, and empathy. That’s the difference between simply doing your job and truly standing out in this industry.

    In the next article, I’ll dive into how setting boundaries became a turning point in my leadership approach — not as a sign of resistance, but as a strategy for resilience.

    Ashley Jackway

    Ashley Jackway

    Senior Vice President of Wholesale at Business Purpose Capital (BPC)
    (940) 783-6606 (Direct)
    ashley@bpcapital.com

    Ashley Jackway is the Senior Vice President of Wholesale at BPC, where she leads with transparency, resilience, and a deep commitment to relationship-building. Backed by degrees in Marketing, Accounting, and Business, Ashley brings both analytical depth and creative strategy to the table. With over four years of experience spanning marketing, sales, and hard money lending, she offers a full-spectrum perspective on every deal. Known for her clear communication, solution-driven mindset, and unwavering dedication to her broker partnerships, she has become a trusted and respected force in the lending industry.

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