If your nonprofit feels stretched thin and feeling underwater, you’re not alone. Strategic planning is the process that helps you turn good intentions into a clear, shared and actionable direction. It’s also how you make sure your board, staff, and donors are rowing in the same direction.
Here are seven signs it’s time to invest in a new strategic plan — or to simply refresh an existing plan.
1. Your board keeps having the same conversations
If every board meeting feels like Groundhog Day, that’s a clue. You’re revisiting the same topics — budget shortfalls, staff turnover, program changes—without a clear path forward. A strategic plan gives you a shared framework to guide decisions, so you’re not just reacting to the latest fire.
2. Your mission statement and values are gathering dust
You have a mission statement somewhere in a document, but it doesn’t show up in conversations, proposals, or evaluations. When your mission isn’t guiding your work, it’s easy to drift into “whatever feels urgent today” mode. Same goes for your values. If you are making decisions that bump up against your values, you are out of alignment. Strategic planning brings your mission back to the center and builds your priorities around it.
3. Staff and board are confused about priorities
If you ask five people, “What are our top three priorities this year?” and get five different answers, you have a clarity problem. That confusion shows up in missed deadlines, stalled projects, and frustrated teams. A good plan defines 3–5 strategic goals and makes it clear who owns what.
4. You’re in constant survival mode
Funding is unpredictable. Programs are stretched. You’re chasing the next grant or the next event just to keep the lights on. That’s exhausting — and it’s hard to build long-term impact when you’re always in emergency mode. Strategic planning helps you step back, assess your options, and design a more sustainable path.
5. You’ve gone through major changes
New executive director. New board chair. New programs. New funders. Any of these shifts can change your organization’s trajectory. If you’ve had significant leadership or program changes in the last year or two, your old plan may no longer fit. A refresh helps you align around where you’re going next.
6. You’re struggling to hit revenue or impact goals
If you keep missing fundraising targets, or if your programs aren’t delivering the outcomes you hoped for, it may be a sign your strategy isn’t working. Strategic planning isn’t just about setting goals — it’s about building a realistic plan to get there, with metrics, timelines, and accountability.
7. Your last strategic plan is outdated (or never existed)
If your current plan is more than three years old, it’s likely time for a refresh. If you’ve never had a formal plan, you’re operating on assumptions instead of strategy. Either way, a new planning process can help you get honest about where you are and where you want to go.
What a strategic planning process can do for you
A well-facilitated strategic planning process helps you and your organization:
– Clarify your mission, vision, and values. – Identify 3–5 strategic priorities for the next 1–3 years. – Define who does what, and by when. – Build a plan that’s realistic, actionable, and aligned with your capacity. – Create a shared language for your board, staff, and donors. – Energize your board and team to double down and make a bigger impact.
You don’t need a 50-page plan.
You need a clear, usable blueprint that guides your work and helps you say no to distractions and YES to exponential impact and ease.
Ready to talk about your next plan?
If you’re noticing several of these signs, it might be time to explore a strategic planning process. I work with nonprofits and small businesses to design and facilitate planning that’s practical, inclusive, and focused on action.
I offer a free 30-minute discovery call to learn more about your organization and see if we’re a good fit. In that call, we’ll talk about:
– Where you are now. – What’s working and what’s not. – What a personalized strategic planning process might look like for you.
If you’re ready to move from discussion to direction, let’s talk.
About the author: Shawn Fink is a strategic planning consultant and leadership facilitator based in York, PA. Shawn works with nonprofits and small businesses on strategic planning, board and staff retreats, business planning, and development strategy.
It’s that time of year when the wheels of change slow down a bit. Longtime board members are cycling off and new ones are stepping in. It’s the perfect window to regroup and gear up for the year ahead.
Maybe you’re considering a board retreat to onboard new members and refocus. Or maybe you’ve wanted to host one but haven’t gotten there yet.
After facilitating retreats for boards of all kinds, from highly engaged working boards to governance boards ready to re-energize, I’ve seen what makes the time worth everyone’s while.
Here are 5 agenda items for your next board retreat:
Team Building — Instead of hosting and facilitating your own retreat, bring in an outside facilitator so you can participate and be part of the fun. When I facilitate, I handle the planning, the agenda, and the note-taking, which means every board member, including the ED and board chair, gets to fully engage. Using a retreat to truly connect and build intentional culture is a productive use of everyone’s time.
Mission, Vision, and Values Alignment — Diving deeply into your WHY, or learning it for the first time, can be done in lots of creative ways. This part of your agenda can be fun and engaging as well as informative and impactful.
Review Board Objectives. Visioning and planning for the year, and connecting it to your strategic plan, is vital to meeting goals. When board members understand their assignment, the impact is felt across the whole organization. In my retreats, I always sequence visioning before priorities, because boards make better decisions when they can picture the future first.
Brainstorm, Brain Dump and Build Priorities — Board members often know a lot of work needs to happen between meetings, but it hasn’t been assigned to a committee or a lead. Use this time to build a Possibility Matrix for the tasks and projects that will leave a bigger impact down the road. This is one of my favorite parts to facilitate, because it turns vague to-dos into real traction.
Strategic Discussion — Pick one pressing area that needs some TLC, like development or marketing, and dive into it strategically. Board members feel heard and seen for their ideas and investment. That renewed sense of ownership advances the mission in new, bold ways.
Ready to sit back and enjoy your next board retreat?
If you’re a board chair or executive director, you already carry enough. You shouldn’t have to write the agenda, lead the discussion, and take the notes too. When you bring in a facilitator, you get to sit at the table as a full participant, and your board gets a retreat that’s planned, purposeful, and built for traction.
That’s exactly what I do with my Board Impact Intensive, a half-day retreat designed to re-engage your board and set clear direction for the year. Let’s talk about what your board needs next. BOOK HERE
One of the hardest parts of being a small business owner or business leader is making the ASK—and following through on it.
When I work with entrepreneurs who want to grow their revenue, most of our time focuses on messaging and communication strategy. Not just the what and how much, but creating genuine points of connection that convert.
The Politeness Trap
Women, especially, have been conditioned to believe that being polite means not “bothering” people or being too pushy. That good manners require us to wait for clear invitations before reaching out again. That persistence equals pushiness.
But here’s what we’re really doing: we’re prioritizing our own comfort over serving people who genuinely need our help.
When we focus more on politeness and good manners we forget that potential clients are also being polite and are afraid to speak up and ask for help.
Sometimes we just need someone to see us and meet us where we are.
The Hidden Cost of Good Intentions
There are always potential clients, referral partners, and collaborators we could be connecting with to expand our reach and grow revenue. In fact, there are people in your orbit right now waiting for you to reach out—to show them how you can help solve their problems.
I know because I’ve been ghosted repeatedly lately:
As a potential speaker for organizations that desperately need speakers
As a potential client for businesses I wanted to support
As a colleague offering genuine help
This ghosting epidemic isn’t just rude—it’s expensive. Every unanswered email represents lost revenue, missed partnerships, and abandoned growth opportunities.
I’ve read about job applicants feeling ghosted by employers. I’ve read about employers feeling ghosted by potential employees. I’ve read about consultants feeling ghosted by potential clients.
Three Reasons Entrepreneurs Ghost (And What to Do Instead)
If you’re ghosting because you don’t need the business: Respond anyway. A simple “This won’t work right now, but I’d love to refer you to…” builds long-term relationships and reputation.
If you’re ghosting because you’re disorganized: You need customer relationship systems that prevent opportunities from falling through the cracks.
If you’re ghosting because you don’t know what to say: You need a communications strategy that makes outreach feel natural and authentic, not awkward.
The Real Problem: Perfectionism Disguised as Politeness
Your desire to craft the “perfect” response is keeping you from any response at all. Meanwhile, your competitors are showing up imperfectly—and winning your potential clients.
True politeness isn’t about avoiding discomfort—it’s about honoring people with genuine attention and care.
Target’s stock has dropped $4 billion and foot traffic has declined for 10+ consecutive weeks following their abrupt reversal of Diversity, Equity and Inclusion policies.
The company faces ongoing boycotts that began with a 40-day Lenten fast started by Black faith leaders and have evolved into sustained consumer resistance. But this isn’t really an article about DEI — it’s about what happens when companies make major strategic pivots without a solid communication plan.
Target made a classic strategic communication error: they appeared to act reactively instead of strategically. Just four days into Donald Trump’s second-term presidency, Target announced they had met their diversity goals and were eliminating their hiring goals for minority employees and ending diversity committees — a decision that felt reactive and politically motivated rather than strategically sound.
The result? Black Americans, who represent $2 trillion in buying power by 2026, felt betrayed by a company they saw as a friend who ‘championed diversity’.
And, Black Americans weren’t the only consumer block to pull back. Progressives across the spectrum who were used to Target’s progressive advocacy were angered and stopped shopping at the Big Box Retailer.
I recall a conversation I had with a friend and Black business owner the day Target made its announcement; “That hurts, sis. It really hurts,” he said with his hand over his heart.
As a business and leadership strategist with 25 years in strategic communications, here’s what Target could have done differently and what your business should do before making any major public change:
1. Stakeholder Impact Assessment: Before announcing changes, map out who will be affected and how they might respond. Target failed to consider their customer base’s emotional investment in their previous positioning and what this kind of change would do to their consumer spending. Brand loyalty goes beyond daily needs in 2025. Consumers buy with their values as much as they do with their wallets. A thoughtful assessment as part of your strategy would help you plan a strategic rollout of the change.
2. Strategic Communication Plan: Major changes need runway time, not reactive announcements or fiery headlines. A phased rollout approach with true stakeholder engagement and involvement could have prevented the shock and betrayal customers — and businesses — felt.
3. Values-Based Strategic Resilience, Not Political Reactions: If you’re making a pivot, change management requires an authentic positioning strategy — not a political strategy. Your values should be your strategic anchor, not political convenience. Target built their brand on inclusion and diversity and then appeared to abandon those values the moment political pressure mounted. If you’re changing directions, the change must serve your core values, not abandon them. Your stakeholders need to know the ‘why’ behind the change and it must be authentic to your values, not be reactive to external pressure or chaos. Target’s move felt like they abandoned their principles under political pressure — whether that was true or not.
Every business faces moments when internal or external chaos requires a pivot — these days more than ever.
Economic shifts, political changes, social movements — these forces will test your resilience and your clarity. The companies that survive these moments intact are those with thoughtful resilient business strategies, not reactive responses made out of fear.
Forming a change management strategy doesn’t have to be out of your reach as a small business or leader. It simply requires you to slow down, seek out support and perspectives beyond your everyday bubble and the courage to do things slowly and intentionally.
You have permission to slow down and take time to think through major changes.
You have permission to prioritize long-term customer relationships over short-term political pressures.
You have permission to lead with your values and fight for what is important to your business.
If you’re facing a pivot in your business right now and need to make strategic changes, don’t make Target’s $4 billion mistake. Let’s build your strategic leadership plan that protects your customer relationships, supports your valuable team and also positions your business to remain resilient for long-term success.
Because reactive decisions in today’s environment won’t just hurt your brand — they hurt your bottom line.
ABOUT THE AUTHOR
Shawn Fink (she/her) is a business and leadership strategist and coach who helps business leaders to navigate uncertainty and change with strategic clarity. She believes business leaders deserve permission to slow down, think strategically, and make decisions that honor both their values and their bottom line. When the business world feels chaotic, Shawn cuts through the noise to help leaders focus on what actually matters. Her approach combines strategic business foundations with genuine support and understanding of how hard business leadership really is in today’s world.
The silence of leadership isolation is deafening — and I’ve experienced in that silence.
If there is one thing I know beyond doubt, it’s this: Business leaders suffer in silence when things get hard or aren’t working well in their companies. I know because that was my reality for years before I pivoted my work and closed down my first business.
After years of offering products, programs, and courses priced between $5 and $50) and hitting six figures, the market started changing and I lost momentum. Each passing month with sluggish sales I worried I was about to ruin our family’s financial situation. I didn’t know who to turn to or what to say that I felt like a failure or that I was failing others.
Then, I hired a business strategist who carved out an hour to talk with me and get my head on straight. That’s when everything changed.
Resilience withers in isolation. Period.
The Isolation Epidemic in Leadership
Recent research reveals I wasn’t alone in my silent struggle. A staggering 79% of business leaders report experiencing periods of intense isolation during significant business challenges. Yet only 24% ever discuss these struggles openly, creating a dangerous echo chamber where everyone assumes they’re the only one facing such difficulties.
What makes this particularly devastating isn’t just the financial strain—it’s the silence.
During 2017-2018, when my business was struggling most visibly, I hid it all from the world. While maintaining a public face of business-as-usual, I privately questioned everything—my value proposition, my business model, and most painfully, my self-worth. The haunting question played on repeat: “If my friends and loyal audience won’t spend even $15 on something I create, what does that say about me?”
I lost myself. These were the days of what I now call my “midlife icks”—questioning everything about my worth and purpose.
Finding the Path Forward
In 2019, and even more powerfully in 2020, I discovered a new way to exist in the world despite a dwindling bank account and decreasing traffic and sales. I didn’t just survive; I found the capacity to embrace risks, handle disappointments, and still show up with purpose and clarity.
I discovered that what business leaders need most isn’t just their big picture strategy and growth techniques — they also need the CAPACITY to handle the inevitable lows, doubts, and fears that come with taking risks in business and managing uncertainty in the economic environment. And just like they need this work, so do their teams.
Now I help my clients find the clarity, capacity, and courage to show up for themselves and do what they need to thrive and flourish in their businesses. When you have the capacity to handle risk, embrace failure, and still get up each morning to try again—you know you’ve reached a point where you can do almost anything.
My STRONG™ Framework: Cultivating Unshakeable Resilience
Through my own journey and work with hundreds of business leaders and upon my completion of my positive psychology certification, I’ve developed a comprehensive approach to cultivating resilience I call the STRONG™ framework. This isn’t about bouncing back to where you were —i t’s about bouncing forward into who you’re meant to become — as a business leader and as a person.
When we’re facing business challenges, our instinct is often to focus on weaknesses or failures — ours or other people’s. But resilience begins with reconnecting to our innate strengths and seeing them in others.
Practical Application: Think back to a time in your past when you were at your best, even if it was during hardship. What strengths did you use to get through? Focus on your greatness, not your weaknesses.
During my darkest business days, I reconnected with my natural abilities for empathetic connection and authentic communication. I stopped trying to be a “conventional business person” and instead leaned into my true authentic self and strengths — which ultimately became the foundation for the reinvented business model I have now.
T: Thrive and Shine in Positivity
Business challenges can quickly spiral us into persistent negativity that clouds our thinking and decision-making. Deliberately cultivating positive emotions creates the mental space needed for innovative solutions.
Practical Application: Intentionally create space for gratitude, joy, hope, serenity, love, pride, and humor in your daily routine.
I started a 30-day practice of writing down three moments of business joy, no matter how small—a kind email from a client, a moment of clarity during a walk, the perfect cup of coffee while working on a new idea. This practice shifted my focus from scarcity to possibilities, even when the bank account hadn’t changed.
R: Reaching Out and Building Relationships
The isolation that comes with business struggles is not just emotionally painful — it’s harmful in the workplace and in our families. We lose perspective and access to collective wisdom.
Practical Application:
Cultivate relationships with a friend or therapist to offload emotions during times of struggle.
Find a mentor, coach, or inspiring colleague who can lift you up and out of your own story to see the bigger picture.
I have a “truth-telling circle” of three other business owners who meet semi- monthly. In this sacred space, we can share our real lives, real fears, and real challenges without judgment. This circle became my lifeline during my transition period, providing both emotional support and strategic insights I couldn’t have accessed alone. I recently joined another group as well that is similar.
O: Open Your Mind to Possibilities
When business isn’t working, our thinking narrows dramatically. We see fewer options, fewer resources, and fewer possibilities precisely when we need expansive thinking most. We think we are trapped and stuck but that is anything but the truth.
Practical Application: Keep an open mind by asking powerful questions such as:
What am I not seeing right now?
What good is happening that I cannot see?
Who am I becoming because of this struggle?
I began questioning my assumptions about what “success” looked like. When I opened my mind beyond revenue milestones to impact, personal growth, and alignment with my values, entirely new business models emerged that I couldn’t have seen through my previous tunnel vision.
N: Nurture Your Whole Self
Business resilience isn’t separate from personal resilience. Leaders who neglect their holistic well-being during challenging times diminish their capacity for creative problem-solving and perseverance.
Practical Application: Create intentional practices to nurture all dimensions of your well-being eco-system:
Physical well-being
Spiritual well-being
Emotional well-being
Relational well-being
Heartful well-being
Financial well-being
Intellectual well-being
Meaningful well-being
During my business transition, I committed to my well-being practices despite workload or stress level. Keeping these simple practices became my sanity anchor, providing physical movement, mental clarity, and emotional regulation that kept me functioning even on my darkest days. Now, I do these practices regularly as maintenance to thrive daily.
G: Grow Yourself Forward
The only way through business challenges is forward — not back to where you were, but forward into who you’re becoming through this experience and creating the kind of business environment that brings you joy, respect and a thriving life for all.
Practical Application:
Embrace a growth mindset rather than a fixed mindset
Work toward meaningful goals that bring you alive and give you purpose
I began seeing my business challenges not as failures but as the exact experiences I needed to develop the wisdom, empathy, and frameworks that now allow me to coach others through similar journeys. Every setback was actually setting me up for my most aligned work.
The Power of Bouncing Forward
Resilience isn’t about returning to your previous state after difficulty. True resilience is about integrating the experience into your leadership identity and moving forward with greater capacity, wisdom, and purpose.
As Al Siebert wisely noted: “When you are hit with life-disrupting events, you will never be the same again. You either cope or you crumble; you become better or bitter; you emerge stronger or weaker.”
Resilience is the key—and it blooms in certain conditions and withers in others. My mission now is to create the conditions where your resilience can bloom, even during the most challenging business circumstances.
Your Resilience Journey
The path to unshakeable resilience begins with a single step—choosing one element of the STRONG framework that resonates most deeply with your current situation. Implement it consistently for two weeks before adding another practice.
Remember: When you have the capacity to handle risk, embrace failure, and still get up each morning to try again—you’ve developed the superpower that transcends any business model or market condition.
I’ve walked through the valley of entrepreneurial despair and emerged with tools, frameworks, and wisdom that transformed my relationship with business challenges. Now I help other business leaders develop the capacity not just to endure difficult periods but to use them as catalysts for their next level of impact and fulfillment.
Your business challenges aren’t the end of your story—they’re the beginning of your most meaningful chapter. Let’s write it together.
Ready to discover your organization’s resilience advantage?
Schedule a focused 30-minute consultation to discuss:
How we can identify your most pressing productivity challenges
Determine if the STRONG Workplace™ Wellbeing Impact Assessment is right for your organization
Outline exactly what the assessment process involves
Answer any questions about implementation and outcomes
Schedule your strategy call now to learn more about the STRONG Workplace™ Wellbeing Impact Assessment process.
Shawn Fink is a Business Strategist & Organizational Wellbeing & Resilience Consultant with Shawn Fink Strategies LLC. She works with overwhelmed business leaders (founders & executives) and teams on developing calm, big picture strategy and small detail thriving. She also offers business strategy and project management to micro organizations. If you’d like to find out how she can help you, schedule a Strategic Slowdown Chat with her today.
Here are 5 agenda items for your next board retreat:
Shawn Fink (she/her) is a business and leadership strategist and coach who helps business leaders to navigate uncertainty and change with strategic clarity. She believes business leaders deserve permission to slow down, think strategically, and make decisions that honor both their values and their bottom line. When the business world feels chaotic, Shawn cuts through the noise to help leaders focus on what actually matters. Her approach combines strategic business foundations with genuine support and understanding of how hard business leadership really is in today’s world.
