At Saulsberry Group, we believe that transformation isn’t just about high-level planning—it’s about bridging the gap between vision and reality. We specialize in helping organizations connect their daily operations to long-term strategic success, crafting customized roadmaps that turn ambitious goals into tangible results.
But what does that actually look like in practice? How do we take a client’s unique challenges and translate them into a clear, actionable strategy?
Let us take you behind the scenes of a powerful experience—one that brought strategy to life for an organization making a meaningful impact in its community.
Before going too far, I want issue a word of caution. There are 3 critical steps and 17 additional deliverables excluded from this example. The organization receiving the results of this abbreviated approach will need to engaged in additional services to make the strategic transformation experience complete. Attempting to use what I am sharing about strategic transformation in its incomplete form and without requisite experience will lead to more confusion for your organization. I am sharing more about the process of strategic transformation to allow you to see all that’s involved, the value added, and the results. My experience doing this work spans 20 years. This is the only reason I am able to execute an abbreviated process in this instance.
A Partnership with Purpose
It all started with a simple request. Margaret Johnson, Executive Director of Dress for Success Charleston County (DFS Charleston), reached out to Ja’nister Herring, CEO of Essence Technology Consulting, for help with a technology need. But as Ja’nister listened, she saw a bigger picture—an opportunity for deeper, more transformative problem-solving.
Through our strategic alliance with Essence Technology Consulting, Saulsberry Group was introduced to DFS Charleston. What began as a conversation about technology quickly evolved into a mission to strengthen the organization’s foundation and amplify its impact.
When we toured DFS Charleston’s storage facility, we didn’t just see racks of donated clothing—we saw stories, aspirations, and an urgent need to create sustainable solutions. Margaret shared eye-opening statistics:
- 55% of first impressions are based on appearance, and it takes just 7 seconds to form a lasting impression.
- Well-dressed individuals are perceived as more competent, trustworthy, and capable in professional settings.
- A quality business outfit can cost between $100 and $500, creating a significant barrier for job seekers.
- 70% of low-income job seekers report that lack of professional attire is a major obstacle to employment.
As we listened to Margaret describe her daily responsibilities and challenges, we saw an incredibly passionate leader who was deeply committed—but also consumed by day-to-day operations. She needed the space to think strategically, to lift her head from the immediate tasks and focus on the bigger picture.
That’s when we at Saulsberry Group knew: we had to help.
The Strategic Workshop: Breaking Down the Challenges
Determined to provide meaningful support, Saulsberry Group offered a pro bono strategic planning session. We gathered key DFS Charleston stakeholders for a four-hour interactive workshop designed to uncover challenges, identify opportunities, and build a roadmap for the future.
Step 1: Identifying the Core Issues
We began by inviting participants to share the biggest challenges facing the organization. This wasn’t about quick fixes—it was about listening, empathizing, and truly understanding the obstacles they encountered daily.
The result? 21 well-defined problems spanning different aspects of the organization. Instead of dismissing or downplaying these challenges, we embraced them. Every problem was acknowledged, analyzed, and given the attention it deserved.
Step 2: Finding Patterns and Themes
From these 21 challenges, four overarching themes emerged:
- Attracting Sponsors – Creating a compelling marketing strategy to drive funding and engagement.
- Establishing a Physical Location – Developing a dedicated space to enhance credibility and service delivery.
- Structuring the Organization – Strengthening internal operations and governance.
- Expanding Services – Scaling programs to reach more clients and maximize impact.
With these themes in mind, we crafted an initial problem statement:
“Building a sustainable Dress for Success offering for the Charleston Metro Area (Lowcountry).”
From Challenges to Solutions: The Power of Ideation
Once we had a clear understanding of the problem, we shifted our focus to solutions. In a rapid-fire brainstorming session, the team generated 25 innovative ideas to tackle the organization’s biggest challenges.
To prioritize these ideas, we used a structured qualification process:
- Effort Estimation (T-shirt Sizing): Ideas were categorized from XS (quick wins) to XXL (long-term initiatives) based on the time required for implementation.
- Cost Assessment ($ Scale): Each idea was evaluated on a financial scale, from $$ (low-cost solutions) to $$$$$$ (major investments).
The Strategic Roadmap: A Vision for the Future
With all this data in hand, Saulsberry Group crafted a comprehensive five-year strategic plan (2025-2030) for DFS Charleston. The plan included:
Updated Organizational Problem Statement
Dress for Success Charleston cannot build a sustainable offering for its clients because it struggles with financial sustainability, volunteer retention, outreach diversity, and organizational structure, while also facing significant challenges in marketing and advertising. These limitations reduce its visibility, hinder partnerships, and restrict its ability to expand impact.
Four Key Strategic Priorities
- Finances and Resources – Strengthening financial sustainability through diversified funding.
- Marketing and Outreach – Enhancing visibility and brand awareness.
- Volunteer and Staffing – Improving recruitment, retention, and organizational capacity.
- Client Experience and Inclusivity – Expanding services to better serve the community.
Each strategic priority was backed by actionable initiatives, realistic timelines, and estimated costs—giving DFS Charleston a clear roadmap to success. (the table below is proprietary and not intended to be read)
The Impact: A Renewed Sense of Purpose
Armed with a well-defined strategic plan, Margaret and her team walked away with:
- Clarity on the organization’s biggest challenges and how to address them.
- A roadmap for the next five years, grounded in realistic, achievable goals.
- A framework to align day-to-day operations with long-term success.
- A newfound confidence in communicating DFS Charleston’s mission to stakeholders and funders.
Reflecting on the experience, Margaret shared:
“Thank you to the Saulsberry Group and Essence Technology Group for their exceptional leadership during our strategic session with DFS Charleston’s committee and board members. Your thoughtful guidance through each step of the process has been invaluable in helping us identify opportunities for growth. The insights shared have given us a renewed sense of focus and a roadmap to drive meaningful improvement. We truly appreciate your expertise and commitment to our success.”
Margaret and her team had a great experience and left being more closely connected and vested in the success of Dress for Success Charleston. Out of this experience emerged an updated vision and mission statement:
Taking the “dress” out of “success” by empowering, educating, and inspiring our Clients.
What About Your Organization?
Every organization, no matter how big or small, faces strategic challenges. The key is knowing how to navigate them effectively.
Are you ready to take your organization to the next level?
Take our Transformation Readiness Survey today and discover how Saulsberry Group can help you unlock your full potential.vely
Alternatively, if you simply want to discuss the challenge you’re facing, Book A Meeting and let’s discuss your opportunity for transformation.
Lastly, I reiterate my word of caution mentioned earlier. If you have questions about the strategic transformation process, please reach out. Take a look at the What We Do section to learn more about our services and products. Book A Meeting with me to discuss your specific needs.
