From Federal Warden to Leadership Consultant: Darlene Drew on Building Your Practice, Pricing Mistakes, and Running a Business Through Grief (The Price and Value Journey, Episode 153)
Do you want to know how to build a professional services business when you have deep expertise but no client base? Darlene Drew shares exactly how she did it after retiring from 32 years in federal corrections, including her time as the first and only woman to serve as warden at the U.S. Federal Penitentiary in Atlanta.
Darlene didn’t join the John Maxwell Team for certification. She joined for resources, guidance, and a roadmap to build relationships in a world entirely different from the one she knew. She reveals her strategic approach to launching her speaking, training, and coaching business, including how she used free speaking at Rotary Clubs within a 90-mile radius to build visibility and generate paying clients. You will learn why she initially wanted to leave “Warden Drew” behind and how her clients taught her that her unique background was actually her greatest asset.
This conversation gets practical fast. Darlene shares the underpricing mistakes she made early on, how demanding clients helped her recognize she was undervaluing her work, and the internal signals that told her it was time to raise her rates. She discusses client red flags she missed, the one engagement she deeply regretted taking, and why giving yourself grace to say no is critical to building a sustainable business.
The second half of the episode shifts to navigating one of life’s hardest challenges. Darlene opens up about losing her husband to pancreatic cancer in 2024 and what it’s been like to rebuild her business while grieving. She shares what helped her, what didn’t, the language that serves grieving people versus the well-intentioned phrases that fall flat, and why “moving forward” isn’t the right frame. If you’ve ever supported a colleague or client through loss or faced it yourself, this part of the conversation offers real wisdom on presence, boundaries, and incremental steps back to work.
The Price and Value Journey is presented by John Ray and produced by North Fulton Business Radio, LLC, an affiliate of the Business RadioX® podcast network.
Key Takeaways You Can Use from This Episode
- Speaking for free at the right venues can build your business faster than waiting for paid gigs. Darlene used Rotary Clubs within a 90-mile radius to showcase her expertise, build relationships with business leaders, and generate training contracts.
- You don’t need certification to start. You need resources, guidance, and a way to meet your ideal clients. Darlene joined the John Maxwell Team not for credentials but for content, community, and a roadmap to build her business outside corrections.
- Clients will tell you what they value, and it’s often not what you think. Darlene wanted to retire “Warden Drew,” but corporate clients saw her corrections background as a unique asset for leading difficult conversations and motivating teams under pressure.
- Underpricing reveals itself through client behavior. When clients who barely paid demanded more than those who invested significantly, Darlene realized she wasn’t valuing her own work and adjusted her pricing accordingly.
- Red flags in client conversations matter. If a potential client does not invest time in understanding the problem or co-creating solutions, they are likely seeking a quick fix rather than a solution. Trust those signals early.
- When supporting someone through grief, presence beats advice. A weekly card, an offer to help without expectation, or simply waiting to listen means more than advice, scripture quotes, or questions about “moving forward.”
- It’s okay to set boundaries around your grief and ask for what you need. Darlene paused her workaholic tendencies, took incremental steps back into client work, and communicated clearly with her network about what “navigating grief” looked like for her.
Topics Discussed in this Episode
00:00 Introduction and Guest Welcome
02:02 Darlene Drew’s Career Journey
04:01 Transition to Leadership Training
07:23 Joining the John Maxwell Team
18:38 Building a Speaking Business
26:29 Networking and Referrals
29:17 Developing Pricing Strategies
31:19 Using Google as a Starting Point
33:22 Recognizing Underpricing Signals
35:30 Identifying Poor Fit Clients
37:51 Lessons from a Difficult Client
40:54 Coping with Personal Tragedy
44:35 Navigating Grief and Business
45:28 Support Systems During Grief
52:05 Healing Routines and Self-Care
59:28 Future Plans and Moving Forward
01:01:28 Final Thoughts and Contact Information
Darlene Drew, CEO, Leadership Conditioning, Personal & Professional Development
Darlene Drew is the CEO and Founder of Leadership Conditioning, Personal & Professional Development, LLC. She is also a certified & independent leadership trainer, professional speaker, and executive coach with the Maxwell Leadership Team.
Darlene serves businesses, companies, and organizations by helping leaders develop leaders. Through her training sessions, she equips, engages, and energizes participants with leadership and professional development training by providing them with tools that can immediately be applied in their personal and professional lives.
As an authority in leadership, building relationships, and communications, she helps organizations develop their staff in a manner that improves their bottom line of first valuing people, which improves the operation of their business and the performance and production of their staff.
She has been recognized in the Maxwell Leadership Team as one of the Top 20 Nominees for the Maxwell Leadership Team Culture Award. She’s a 2019 Stage Time Winner. Darlene has been featured in the Peachtree City Magazine on two occasions.
More recently, in 2023, Darlene was one of only 10 recipients of the Culture Award from the John Maxwell system. Her specific award was on “Lead and Lift.”
Her prior career began in the federal government at the entry level as a correctional officer, promoted up to a Senior Executive Service Appointment to the position of Warden. One of her most groundbreaking accomplishments was becoming the first and only female to serve as warden at the United States Penitentiary, Atlanta, GA. She served as warden of three federal prisons after being told early on in her career that she would never make it!
These dynamics brought leadership expertise that has positioned her to help those she partners with in their growth.
John Ray, Host of The Price and Value Journey
John Ray is the host of The Price and Value Journey.
John owns Ray Business Advisors, a business advisory practice. John’s services include business coaching and advisory work, as well as advising solopreneurs and small professional services firms on their pricing. John is passionate about the power of pricing for business owners, as changing pricing is the fastest way to change the profitability of a business. His clients are professionals who are selling their expertise, such as attorneys, CPAs, accountants and bookkeepers, consultants, coaches, marketing professionals, and other professional services practitioners.
John is a podcast show host and the owner of North Fulton Business Radio, LLC, an affiliate of Business RadioX®. John and his team work with B2B professionals to create and conduct their podcast using The Generosity Mindset® Method: building and deepening relationships in a non-salesy way that translates into revenue for their business.
John is also the host of North Fulton Business Radio. With over 900 shows and having featured over 1,300 guests, North Fulton Business Radio is the longest-running podcast in the North Fulton area, covering business in its region like no one else.
John’s book, The Generosity Mindset: A Journey to Business Success by Raising Your Confidence, Value, and Prices
John Ray is the author of the five-star rated book The Generosity Mindset: A Journey to Business Success by Raising Your Confidence, Value, and Prices, praised by readers for its practical insights on raising confidence, value, and prices.
If you are a professional services provider, your goal is to do transformative work for clients you love working with and get paid commensurate with the value you deliver to them. While negative mindsets can inhibit your growth, adopting a different mindset, The Generosity Mindset®, can replace those self-limiting beliefs. The Generosity Mindset enables you to diagnose and communicate the value you deliver to clients and, in turn, more effectively price to receive a portion of that value.
Whether you’re a consultant, coach, marketing or branding professional, business advisor, attorney, CPA, or work in virtually any other professional services discipline, your content and technical expertise are not proprietary. What’s unique, though, is your experience and how you synthesize and deliver your knowledge. What’s special is your demeanor or the way you deal with your best-fit clients. What’s invaluable is how you deliver outstanding value by guiding people through massive changes in their personal lives and in their businesses that bring them to a place they never thought possible.
Your combination of these elements is unique in your industry. There lies your value, but it’s not the value you see. It’s the value your best-fit customers see in you.
If pricing your value feels uncomfortable or unfamiliar to you, this book will teach you why putting a price on the value your clients perceive and identify serves both them and you, and you’ll learn the factors involved in getting your price right.
The book is available at all major physical and online book retailers worldwide. Follow this link for further details.
