Leading Through Change - Courageous Conversations In Uncertain Times Ep. 50
Release Date: 08/11/2025
Been There Sold That
Everyone wants better results - the real challenge is knowing when to act and what to act on. In this episode of Been There, Sold That, Brianna Henley and Phil Whitebloom talk about why waiting often feels like the safest option in business, and why it rarely delivers the outcome leaders are hoping for. Problems in leadership, operations, growth, and revenue do not resolve themselves simply because time passes. Business improvement comes from clear, intentional action. We explore why capable, experienced business owners and leaders hesitate, how delay shows up across different areas of a...
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Every salesperson and every business hits a slump. The real problem is not the slump. It is what you do next. In this episode of Been There, Sold That, Phil Whitebloom and Brianna Hendley talk about how tobreak out of a sales slump by changing behavior, energy, and mindset, and how making the process fun can reignite momentum faster than grinding harder ever will. They share real stories from decades in sales and recruiting, including call blitzes, creative contests, personal challenges, and unconventional outreach ideas that actually worked. The common thread is simple. When activity drops,...
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Money is one of the most emotional topics in business and one of the most avoided. In this episode of Been There, Sold That, Phil Whitebloom and Brianna Hendley have an honest, real-world conversation about business finances, budgeting, and decision-making from the perspective of people who have lived it. They talk about what happens when expenses quietly grow, investments stop producing results, software subscriptions pile up, and revenue looks strong on paper while cash flow tells a different story. They also explore why some businesses generate millions in revenue and still struggle...
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Why Holiday Pressure Creates the Perfect Window for Big Sales Wins When the calendar tightens, vacations stack up, and the number of real selling days drops fast, something interesting happens: buyers make decisions, deals accelerate, and opportunities open that weren’t available all year long. In this episode, Phil Whitebloom and Brianna Hendley break down exactly how to capitalize on the urgency of the season. Whether it’s the holidays, the end of a fiscal period, or simply a compressed window to hit big goals, this conversation shows you how to turn pressure into profit. You’ll...
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In this episode of the Been There Sold That Podcast, hosts Brianna Hendley and Phil take a real, honest look at what work-life balance actually means — and why so many professionals struggle to achieve it. If you’ve ever felt stretched too thin, torn between responsibilities, or unsure how to prioritize what matters most, this conversation is for you. Brianna breaks down the power of setting boundaries, planning with intention, and knowing your “why” so you can create a life and business that support each other instead of competing for your energy. Phil shares relatable stories and...
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In this special episode of Been There Sold That, co-host Brianna Hendley flips the script and interviews her longtime partner — sales coach, author, and BeenThere Consulting founder Phil Whitebloom. Hear how Phil’s career started the Monday after college, selling dictation machines in Milwaukee, and evolved into leading national sales teams, generating more than $1.5 billion in revenue, and coaching businesses to immediate results. Phil shares the real-world lessons that shaped his philosophy on sales, leadership, and life — from brutal early training programs to the turning points that...
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Most businesses fight in crowded markets when the real money sits in overlooked niches. In this episode, Phil Whitebloom and Brianna Hendley show you how to spot under-served segments, validate demand, and turn them into consistent revenue. You will hear how Brianna leveraged a long career in the government sector to spin up a recruiting and consulting arm under her coaching company, why you should pressure test any new niche before jumping, and how to use AI to map targets, refine offers, and plan outreach. The conversation draws on , focusing on practical moves you can make inside the...
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In this episode of Been There, Sold That, hosts Phil Whitebloom and Brianna Hendley break down what real networking looks like in today’s business world. Forget the awkward “What do you do?” introductions—this episode dives into how to turn every conversation into opportunity by being intentional, specific, and story-driven. Phil and Brianna share practical strategies to: Identify who you should really be networking with Craft a 30-second story that gets attention and earns trust Set clear goals for each event (hint: seven appointments beat seven business cards) Avoid wasting...
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On Been There, Sold That, Phil Whitebloom and Brianna Hendley break down a simple truth that closes deals faster: match your prospect’s psychological state. In this episode, they reveal how to open every meeting with clear expectations, ask the right discovery questions, and deliver proof at the right time so your demo lands and trust grows. You’ll hear a real story of a sale lost by over-questioning—and exactly how to fix it with active listening, expectation setting, and responsive communication. What you’ll learn in this episode: How to read the room and align with the buyer’s...
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On Been There, Sold That, Phil Whitebloom and Brianna Hendley tackle a quiet profit killer in every business: high-conflict emails. Learn when to pick up the phone, how tone and punctuation change outcomes, and why the number of recipients matters. Phil shares a real miscommunication with a client and the simple fixes that prevent repeats. Brianna lays out foundational communication skills for professionals, plus practical NLP techniques to tailor messages to how people process information. Before you hit send, use this playbook to keep relationships strong and conversations productive. What...
info_outlineIn this landmark 50th episode, hosts Brianna Hendley and Phil Whitebloom delve into the crucial topic of courageous conversations during uncertain times.
Leadership often requires addressing tough conversations, particularly when the future is unclear. Whether it’s restructuring a team, delivering difficult news, or navigating the emotional complexities of layoffs, how you approach these discussions can define your leadership legacy. Brianna and Phil share a human-centered framework to tackle these conversations with empathy, clarity, and strength.
💡 In This Episode, You’ll Discover:
✔ A simple framework for handling difficult conversations that fosters trust and respect.
✔ Techniques for approaching tough talks while maintaining team morale.
✔ Strategies for leading with empathy and clarity, even in emotionally charged situations.
The hosts emphasize that courageous conversations are essential for effective leadership. By focusing on empathy and clear communication, you can navigate the toughest discussions while preserving relationships and morale.
🔥 Takeaway: Equip yourself with the tools to engage in challenging conversations without undermining trust or team spirit.
Connect with Brianna Hendley, Founder of Achievant Coaching at bhendley@achievantcoaching.com | www.achievantcoaching.com and Phil Whitebloom, Founder of Been There Consulting Services at phil@beentherecs.com | www.beentherecs.com.
#LeadershipDevelopment #CourageousConversations #HRLeadership #EmotionalIntelligence #ChangeManagement #DifficultConversations #AuthenticLeadership #WorkplaceCulture #CareerResilience #LayoffSupport