One of the greatest benefits of WBO membership is supporting and celebrating the impactful work of our members. This month, we are proud to spotlight the meaningful community efforts of our member firm, CovingtonAlsina, as they help raise awareness for vital services supporting military families.

During National Veterans & Military Families Month, CovingtonAlsina partnered with For All Seasons Behavioral Health and Rape Crisis Center—the only behavioral health and rape crisis center serving Maryland’s Eastern Shore. Through its Service Members, Veterans, and Families (SMVF) initiative, For All Seasons provides same-day appointments, crisis response, trauma-informed therapy, and support services for veterans, active-duty service members, spouses, and children.

Founded by WBO member Ann M. Covington, CovingtonAlsina has long served military households and understands the unique financial and life challenges that come with deployments, relocations, and complex benefits systems. Their partnership with For All Seasons helps connect more families to critical emotional and mental health resources—creating a powerful bridge between financial stability and personal well-being.

This collaboration reflects the heart of our WBO community: women-owned businesses using their expertise and influence to make a meaningful difference beyond their own companies.

The holiday season is one of the most important—and potentially profitable—times of year for small businesses. Whether you sell products, offer services, or run events, preparation is key to maximizing revenue, reducing stress, and creating meaningful connections with your customers.

To help you get ahead, we’ve put together practical strategies to guide your holiday planning.

Here’s how to prepare your small business for a successful holiday season:

1. Start Early: Planning Now Saves Time Later

Early preparation allows you to:

• Stay ahead of supply delays

• Build intentional marketing campaigns

• Prevent last-minute stress

• Deliver a polished customer experience

Before planning anything new, review last year’s performance:

• What worked well?

• What didn’t?

• Which products or services were most popular?

• What challenges did you face?

This helps you make data-backed decisions instead of guessing.

2. Create Your Holiday Marketing Strategy

The holidays are a peak season for visibility—but also for noise. A strong marketing plan keeps your message clear and compelling.

Key strategies to consider:

• Holiday Promotions: bundles, early-bird specials, VIP sales, gift cards, or limited-time offerings

• Seasonal Branding: update your website banner, social profiles, and email graphics

• Content Calendar: pre-schedule holiday emails, reels, posts, and stories

• Partnerships: collaborate with complementary businesses to extend your reach

• Engagement: run polls, giveaways, or community-centered campaigns

Your messaging should speak to the season’s mindset: convenience, gifting, appreciation, and celebration.

3. Prep Your Operations & Logistics

The operational side can make or break your holiday season.

Check your:

• Inventory: reorder top sellers early

• Supplies: packaging, shipping materials, branded inserts, or holiday extras

• Staffing & Scheduling: adjust hours, build coverage, and set communication expectations

• Shipping Deadlines: clearly communicate cut-offs on your website and social platforms

If you work in services, consider:

• Offering holiday bundles

• Extending appointment availability

• Creating a waitlist system

• Automating reminders

Small adjustments now prevent big problems later.

4. Elevate the Customer Experience

Even small touches can create memorable experiences customers rave about.

Consider adding:

• Gift-wrapping

• Handwritten thank-you notes

• Holiday-themed packaging

• Loyalty rewards for repeat purchases

• A customer appreciation event or discount

Acts of gratitude go a long way—especially during the busiest season of the year.

5. Mind Your Well-Being (Seriously)

The holidays can be overwhelming for business owners, especially women who are often managing both business and family responsibilities.

Protect your energy by:

• Blocking personal/family time in advance

• Delegating tasks where possible

• Automating processes

• Pre-scheduling content and communications

• Setting boundaries with your calendar

A joyful business owner creates a joyful customer experience.

6. A Simple Holiday Prep Checklist

Here’s a quick version your members can save:

✔️ Plan Ahead

• Review last year's performance

• Set goals for this season

✔️ Marketing

• Define promotions and offers

• Schedule social and email content

✔️ Operations

• Check inventory

• Prepare staffing and schedules

✔️ Customer Experience

• Add seasonal branding

• Plan a customer appreciation touch

✔️ Self-Care

• Block personal time

• Delegate/automate tasks

Final Thoughts

The holiday season doesn’t have to feel chaotic—with early planning, thoughtful marketing, and attention to customer experience, your business can finish the year strong.

And if you need support designing an unforgettable holiday event or branded experience, Anne Urban, with Destination Planning Corporation, is an excellent resource within our membership community.

Stay organized, stay intentional, and cheers to your most successful holiday season yet!

As a business owner, protecting your business is just as important as growing it. Insurance isn’t just a box to tick off—it’s a vital part of your overall risk management plan. This month, we tapped the expertise of long-time WBO member Vicky Zelen of Zelen Risk Solutions to share key insights every entrepreneur should know about business insurance.

1. The Must-Have Insurance Policies for Every Business

Vicky highlights the core types of insurance every business should consider:

✅ General Liability Insurance: Protects you if you accidentally cause harm or property damage to a third party. Essential for nearly every business.

✅ Professional Liability Insurance: Crucial if you offer advice or professional services. Think accountants, consultants, and designers.

✅ Commercial Auto Insurance: If you make deliveries, pull trailers, or transport customers, personal auto insurance often falls short.

✅ Uninsured Motorist Coverage: A must-have to protect yourself and passengers if someone else causes an accident but lacks adequate insurance.

✅ Comprehensive and Collision Coverage: For protecting your vehicle from damage, theft, weather, and accidents. Vicky advises opting for lower deductibles that truly save you money.

✅ Workers Compensation Insurance: Even if not required, it’s worth quoting. Injuries can happen at any time, and coverage protects both you and your team.

✅ Umbrella Liability Insurance: Adds an extra layer of protection over your General Liability or Commercial Auto policies.

2. Common Misconceptions About Business Insurance

One big misconception Vicky sees often:

“Many people think if you buy Worker’s Compensation on yourself, making a claim means you’re suing yourself. That’s not the case—it’s a benefit that helps protect you and your team.”

Understanding your coverage—and how it works—can make all the difference when challenges arise.

3. Right-Sizing Your Coverage

Business size, industry, and operations all influence how much coverage you need. Vicky recommends getting written quotes that include:

• Clear descriptions of your business operations

• Accurate risk classification

• Optional quotes for different coverage limits and deductibles
  
  

4. Risks and Liabilities Women Business Owners Might Overlook

While Vicky didn’t elaborate specifically here, it’s a good reminder that risks can differ for each business. Collaborate with a knowledgeable agent who takes the time to understand your unique needs.

5. Advice for New Business Owners

When shopping for coverage, Vicky suggests:

• Ask questions.

• Request quotes with clear terms and coverage limits.

• Understand your business classification. For example, a restaurant serving alcohol should be clearly labeled to avoid coverage gaps.

• Compare options. Look at coverage limits, deductibles, and optional coverages to make the best decision.
  
  

6. Real-World Lessons

Vicky shared a story that underscores the importance of detail:
A client added a brand-new SUV to their Commercial Auto Insurance but declined Collision coverage to save money. When the vehicle was damaged in an accident, they were left with a $22,000 bill. Worse, their agent didn’t ask any follow-up questions or offer guidance. Vicky tried to help—though she wasn’t even the agent on record—but the client was left with no coverage.

Lesson learned: Find an agent who truly cares and takes time to ask the right questions.

7. Annual Policy Reviews Matter

Set aside time every year—especially before hurricane season—to talk with your agent. Vicky advises:

“When a storm is on the way, the insurance marketplace can shut down completely until the storm passes. Reviewing your coverage in advance ensures you’re protected.”

8. Choosing the Right Insurance Agent

Your agent should:
✅ Take time to understand you and your business
✅ Shop your policies proactively
✅ Explain your options clearly
✅ Be responsive—especially when you need answers fast

As Vicky puts it:

“An agent who truly cares can make all the difference.”

Final Thoughts

Business insurance isn’t just a policy—it’s peace of mind. Thanks to Vicky Zelen’s expertise, you now have a roadmap to ensure your business is properly protected. Ready to get started? Connect with Vicky at Zelen Risk Solutions to learn more about how she can help you safeguard your business.

In today’s fast‑paced business landscape, confidence isn’t a luxury—it’s a necessity. As women business owners, developing and projecting leadership confidence can mean the difference between blending into the crowd and standing out as a trailblazer. We asked long‑time member and insurance industry veteran Kim Stanley of Kim Stanley Insurance to share her top strategies for exuding and strengthening leadership confidence.

1. Define What Confident Leadership Looks Like

“It’s a tightrope walk: exuding certainty to motivate others while staying agile and empathetic in a world that punishes rigidity.”
— Kim Stanley

Confident leaders know their domain, trust their instincts, and keep ego in check. They balance decisiveness with adaptability—and never underestimate the power of empathy.

2. Build Confidence Through Mastery and Resilience

Confidence grows through repetition and resilience. Kim recommends:

• Own your voice: Speak concisely, maintain eye contact, and avoid qualifiers like “just” or “maybe.”

• Reframe failures: Treat setbacks as learning opportunities.

• Create a support network: Lean on mentors and peers to reflect, learn, and grow.
  
  

By mastering your craft and cultivating resilience, you anchor your confidence in real achievements.

3. Overcome Common Challenges

Women leaders often face stereotyping, bias, and imposter syndrome. Kim’s toolkit includes:

• Resilience: Shrug off bias and keep moving forward.

• Networks: Use your community—like WBO—to amplify your reach.

• Results: Let your track record silence doubters.
  
  

Remember: “Confidence is not about avoiding obstacles; it’s about outmaneuvering them.”

4. Leverage Confidence for Better Decisions & Growth

A confident mindset sharpens decision‑making under pressure. When you “know your stuff,” choices become clearer, and teams rally behind decisive action. This clarity fuels business growth and inspires trust in your leadership.

Quick tip: Before big decisions, remind yourself of past wins—they’re proof you can tackle the next challenge.

5. Adopt a Winning Mindset: Conviction + Adaptability

Kim’s signature strategy:

“Ask yourself, ‘Who is better than you?’ The answer: NO ONE.”

Cultivate conviction in your vision and adaptability in your methods. This mindset empowers you to pivot when needed while maintaining unwavering belief in your capabilities.

6. Harness Networking, Mentorship & Lifelong Learning

Your network is your net worth. Mentors provide perspective and practical know‑how, while continued learning keeps you sharp. Kim credits WBO for the guidance, friendships, and mentorship that propelled her 34‑year career in insurance brokerage.

Final Thoughts

“Your past does not dictate your future,” Kim reminds us. Embrace tenacity, own your worth, and let confidence guide your leadership journey.

Ready to lead with confidence? Explore more insights from Kim Stanley at kimstanleyinsurance.com.

As we step into spring, it's the perfect time for business owners to clear out the clutter—not just physically but strategically. Just like refreshing your home, your business needs regular check-ins to ensure it's running efficiently, aligned with your goals, and positioned for success.

Barbara Tolliver-Haskins, a WBO member and business leadership expert and executive coach with Executive Coaching Solutions, emphasizes the importance of reassessing your business operations regularly. She describes spring cleaning as “not just an activity, but a futuristic energizer”—a time to pause, evaluate, and reenergize your strategy. Drawing from her expertise, we’ve outlined key strategies to help you reset and reinvigorate your business this spring.

1. Evaluate & Refresh Your Business Goals

Mid-year is an excellent time to review your goals and make adjustments based on what’s working and what’s not. Ask yourself:

• Are your goals still aligned with your long-term vision?

• Have market conditions changed, requiring a shift in strategy?

• Are there areas where you've exceeded expectations or fallen behind?

Barbara advises business owners to take a big-picture approach when revisiting their goals. “Start with your vision and mission,” she says. “If your day-to-day actions don’t align with them, it’s time to recalibrate.” She also stresses the importance of benchmarking performance and ensuring accountability across the business.

Pro Tip: Break your goals into quarterly benchmarks. This makes them more manageable and allows for timely adjustments.

2. Identify Areas for Streamlining & Reorganization

Over time, inefficiencies can creep into any business. Identifying bottlenecks and eliminating unnecessary processes can free up valuable time and resources. Consider:

• Are there repetitive tasks that could be automated?

• Do any workflows create unnecessary delays or confusion?

• Are team members aligned with their strengths and responsibilities?

Barbara highlights that team engagement and feedback are essential to identifying inefficiencies. “Even the best of leaders and business owners need to stay in touch with their team’s concerns,” she explains. If your employees feel disconnected or unheard, it can lead to declining morale and productivity. Ensuring open and strategic communication can prevent unnecessary breakdowns in operations.

Pro Tip: Conduct a “time audit” for a week—track where your time goes and identify low-value tasks that can be outsourced or eliminated.

3. Prioritize with the Right Tools & Methods

Spring cleaning your business isn’t just about what to remove—it’s about how you organize and execute tasks going forward. Utilizing productivity frameworks can keep you focused on high-impact activities.

Barbara recommends:

• The Eisenhower Matrix for prioritizing urgent vs. important tasks.

• A quarterly business check-in to assess progress and obstacles.

• A structured action plan that aligns with long-term growth strategies.

She also stresses the importance of proactive decision-making: “Spring cleaning is about looking ahead, not just tidying up loose ends. Be intentional with the changes you make.”

Pro Tip: Use project management tools like Trello, Asana, or Monday.com to keep tasks organized and ensure follow-through.

4. Reignite Your Business Strategy

With your goals refreshed, processes optimized, and priorities in place, the final step is breathing new energy into your business. This could mean:

• Exploring new marketing strategies to reach your ideal clients.

• Revisiting your brand messaging to ensure it’s still relevant.

• Strengthening your network and partnerships for fresh opportunities.

Barbara shares a case study about a business owner whose frequent travel caused team frustration. While the business was financially successful, the lack of leadership presence led to employee disengagement. This serves as a reminder that growth should not come at the cost of team cohesion. “Businesses that thrive are those that are willing to adjust their approach while staying true to their core values,” she shares.

Pro Tip: Schedule a brainstorming session with your team to identify one new growth opportunity for the upcoming quarter.

Final Thoughts

Spring is a time of renewal, making it the perfect season to refresh your business. By revisiting your goals, eliminating inefficiencies, implementing effective prioritization tools, and reinvigorating your strategy, you can set your business up for continued success.

What’s one area of your business you plan to ‘spring clean’ this year? 

Starting a business in 2025 is an exciting and transformative journey, especially for women who are looking to make their mark. Whether you’re taking the leap for the first time, adding another business to your portfolio, or refining your existing venture, there are key areas you’ll need to focus on to set yourself up for success. From legal matters to technology, marketing, and beyond, here are the five essential steps to help you launch your business confidently this year.

1. Legal: Set Your Business Up for Success

Before you dive into the operational side of your business, it’s important to get the legal foundation right. This includes registering your business, understanding taxes, and ensuring you have the right legal structure in place.

Action Steps:

• Choose your business structure (LLC, sole proprietorship, partnership, etc.).

• Register your business with the appropriate local, state, and federal authorities.

• Apply for an EIN (Employer Identification Number) for tax purposes.

• Consult with a legal expert to draft contracts, terms of service, and intellectual property protections.

Need more guidance on setting up the legal side of your business? Reach out to Laurie Lee, owner of The Legal Department, who specializes in building legally sound businesses or Kate Mesic, Mesic Law Firm for expert advice on business law and contracts.

2. Financial: Build a Solid Foundation

Financial planning is critical to the success of any business. Having a clear financial strategy will help you manage cash flow, secure funding, and make smart decisions from day one.

Action Steps:

• Set up a separate business bank account to keep personal and business finances separate.

• Create a budget and financial forecast for the first year.

• Research potential funding options, such as small business loans, grants, or investors.

• Consider hiring an accountant or financial advisor to help with taxes, bookkeeping, and financial planning.

For financial advice and resources, connect with Amanda Bunk-Sizemore of Maige & Sizemore Financial Planning for customized financial strategies tailored to entrepreneurs.

3. Marketing & Branding: Know Your Audience and Craft Your Message

Effective marketing and a strong brand identity begin with understanding who your customers are. Knowing your audience helps you create targeted messaging, tailor your offerings, and connect with potential clients on a deeper level. Once you know who you're speaking to, you can craft a brand and marketing strategy that resonates with them.

Action Steps:

• Define Your Audience: Identify who your ideal customers are by considering factors like age, gender, location, income, interests, and pain points.

• Create Buyer Personas: Develop detailed profiles of your target customers, outlining their needs, goals, and behaviors.

• Tailor Your Message: Craft a brand message that speaks directly to your audience’s values, challenges, and desires.

• Use the Right Channels: Choose marketing platforms where your audience spends their time—whether that's social media, email newsletters, or in-person events.

Need help identifying and reaching your target audience? Allison Walcutt from Branded MKTG can elevate your business marketing strategy.

4. Technology: Start Simple, Then Scale

When you're starting a business, the world of technology can feel overwhelming. From accounting software to project management tools, there’s an endless array of options. However, investing in the right tools early on can help streamline your operations and save you time. The key is to start with the basics, focusing on what’s most important for managing your day-to-day tasks and gradually expanding as your business grows.

Action Steps:

• Start with the Essentials: In the beginning, focus on technology that helps you manage key operations: basic accounting software (e.g., QuickBooks or FreshBooks) and a simple email marketing platform (like Mailchimp) are great starting points.

• Look for All-in-One Solutions: Rather than purchasing separate tools for each function (accounting, project management, etc.), explore software that combines several features in one (e.g., Zoho or G Suite). This reduces complexity and helps you avoid making multiple investments too soon.

• Be Selective About Automation: While automation tools can save time, it’s important not to automate too early. Start with manually handling customer outreach, scheduling, or social media to get a feel for your business needs before investing in complex systems.

• Choose Scalable Tools: As your business grows, you’ll need more robust tools. Invest in systems that can grow with you, offering additional features as your needs evolve.

Unsure about which tech tools are right for you at this stage? Dawn Wilson from Bluefin Tech Group offers expert advice on selecting the right technology for new business owners.

5. Strategy: Plan for Growth and Sustainability

A solid business strategy is essential for long-term success. Knowing where you want to go and how you’re going to get there will keep you on track, even when the road gets tough.

Action Steps:

• Define your short- and long-term business goals.

• Develop a business plan with clear objectives, timelines, and milestones.

• Stay adaptable and be ready to pivot if necessary.

• Build a support network of fellow entrepreneurs to share experiences and strategies.

Our organization is full of experienced members who can help you with every aspect of growing and sustaining your business. By joining, you’ll gain access to a wealth of knowledge, resources, and a network of like-minded women ready to support your journey. Learn more by visiting the Members page of our website.

Conclusion: Your Business Journey Starts Now

Starting a business in 2025 is an exciting opportunity. By following these essential steps and utilizing the right resources, you’ll be well on your way to success. If you’re ready to dive deeper into any of these areas, be sure to connect with the expert members of our community who can guide you through each step.