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Strategic Giving: How to Avoid 9 Common Pitfalls
Discover how to avoid 9 strategic mistakes in strategic giving and maximize your philanthropic impact as a high-net-worth donor.
Learn to maximize your philanthropic impact through strategic giving. Discover how to avoid 5 common strategic mistakes and create lasting change.
Strategic Giving: A Transformative Approach
Imagine you're a successful tech entrepreneur who recently sold your company for a substantial sum. You've always dreamed of making a significant difference in the world, and now you have the means to do so.
But as you sit in your home office, surrounded by reports on global issues and charity evaluations, you feel overwhelmed. The sheer number of causes and organizations vying for your attention is staggering. You want your contribution to create lasting change, but you're paralyzed by the fear of making the wrong choice.
Our twist on strategic giving offers a solution to your issue, combining careful prioritization of problems with practical insights.
By the end of this guide, you’ll have a roadmap of three “sprints” (short, focused periods of work) helping you make rapid yet informed decisions that maximize philanthropic impact without leading to inaction.
Sprint 1: Strategic Giving Prioritizes Relevant and Important Problems
First, Understand Yourself and Others Before Implementing Solutions
A common pitfall in philanthropy is rushing to implement solutions without fully grasping the problem, often leading to wasted resources and potential harm. Instead, begin by understanding yourself, your goals, and the people you aim to serve.
This approach reduces the risk of misaligned solutions and generates higher-quality evidence throughout your philanthropic journey, fostering curiosity and humility—key traits for strategic giving. This also addresses a key risk in innovation: ensuring solutions meet the right needs for the right people.
To implement this, resist the urge to immediately launch solutions, and start with reflection and brainstorming (hit toggle):
- Define Your Purpose: Before starting, ask yourself, "Why am I doing this? What larger goal am I trying to achieve?" Convert this goal into clear, measurable success criteria.
- Identify Your Focus: Reflect on your personal position and starting brainstorming a list of specific communities and their core unmet needs (e.g., education, workforce development, healthcare for first-generation immigrants).
- Build Relationships: Get involved with communities and problem areas early to start learning.
Example
First, reflect on your goals—such as finding community and supporting non-technical nonprofits adapting to AI, given your experience in the AI space. Then, with an open mind, investigate educational challenges in your community. Build relationships and volunteer with frontline organizations to gain valuable insights and a humble, curious mindset. This hands-on approach provides high-quality evidence to inform your decisions, rather than funding a trendy app.
For more on these critical concepts, skim:
Second, Prioritize Your Finalists Through Problem-Position Fit
A common pitfall in philanthropy is adopting a generic approach, often by supporting popular causes or mimicking well-known philanthropists. This strategy can lead to a mismatch between your unique strengths, experience, and the chosen cause, potentially limiting your impact and long-term commitment.
To avoid this, consider your unique position and capabilities. Without this reflection, you risk working on problems that do not align with your expertise or passion, leading to burnout or ineffective solutions.
To implement this strategy, create a strategic prioritization matrix to prioritize the list you brainstormed in the prior step (hit toggle):
- Identify key criteria for personal fit, including the problem's match to your goals, resourcefulness, and network (defined below in the image). These factors predict resilience and innovation in your philanthropic journey.
- Score the problem areas you brainstormed earlier based on these criteria.
- Realize that these are not final scores — just an initial hypothesis. Commit to improving evidence quality throughout your journey
Example
You are a tech entrepreneur with local connections. Your network in the tech industry, combined with your understanding of the local job market and personal experiences with the public school system, uniquely positions you to address the gap between education and employment in your community. This encourages you to explore problems within the education, STEM, and youth development fields.
For more on these concepts, check out:
- Evidence Quality: Strategic Decision Making Framework: Don’t Miss This Essential Tool
Third, Find Your Initial Top 3 Areas with Additional Criteria
A common pitfall in philanthropy is succumbing to quantification bias, where easily measurable outcomes are prioritized over equally important but less quantifiable impacts. Many donors, for instance, focus solely on metrics like the number of people served or dollars spent per beneficiary. However, this approach often overlooks crucial qualitative factors that can significantly influence the effectiveness of future interventions.
Failing to use qualitative filters like the type I share below can result in overlooking high-impact opportunities simply because they're harder to measure. You might end up focusing on problems that are popular or easily quantifiable, rather than those where your contribution could make the most significant difference.
To address these less tangible but vital qualitative factors, identify your top 1-2 hypothetical areas in your matrix:
- Consider using a secondary set of criteria that go deeper into specific issues/problems. Splitting the criteria can be more practical and avoids the burden of scoring problems across too many criteria at once.
- Consider the following secondary criteria that help distinguish truly important problems: core, unmet, and urgent needs.
- Remember that this is a living prioritization matrix. You will be returning to this and revising your hypotheses in future steps as you learn more about the problem and improve your evidence quality
Example
Continuing our scenario, consider using a framework to evaluate potential areas of focus. You might realize that while improving standardized test scores is easily measurable, the fundamental need is actually preparing students for successful careers. This need is largely unmet for students from low-income families and is urgent given the rapidly changing job market. By focusing on these less quantifiable but more fundamental needs, you position yourself to create more meaningful and lasting impact.
For more on these criteria, check out:
Sprint 2: Strategic Giving Promotes Wide & Deep Problem Exploration
But, First, Start by Exploring Quickly and Effectively
A common mistake is getting bogged down in extensive desk research before taking any action. However, this often leads to analysis paralysis and missed opportunities for timely intervention and building valuable feedback loops. Furthermore, overemphasizing the research phase can indefinitely delay action, potentially missing time-sensitive opportunities or failing to build momentum in your philanthropic efforts.
A more effective strategy involves starting simply with quick, practical evidence gathering. This allows for rapid learning and iteration.
To implement this strategy, start with a light Voice of Stakeholder Analysis, which includes (hit toggle):
- Start with readily-available data, such as pre-existing survey results
- Conduct quick surveys or interviews with easily-accessible stakeholders in your top domains
- Use this information to enhance your problem prioritization matrix by sourcing new problems and revising your scores with higher evidence quality
Example
You begin by reviewing existing reports on education and employment in your community. Then, you conduct a short survey of local high school students, recent graduates, teachers, and employers about their career aspirations and challenges.
This quick research may reveal a significant gap between the skills taught in schools and those required by local employers, especially in the tech sector. This insight provides a clear starting point for your efforts, allowing you to take action while continuing to gather more in-depth information.
For specific tips and tools on getting quick feedback, check out these pieces:
Second, Seek Broad and Diverse Perspectives to Identify Systemic Issues
Philanthropists sometimes rely solely on their own assumptions, expert opinions, academic research, or the understanding of just one sector related to the problem, creating a narrow view and anchoring bias, where your initial assumptions remain unchallenged.
A more effective strategy involves connecting with cross-sector stakeholders to gain broad perspectives, ensuring a comprehensive understanding of issues and identifying systemic patterns and critical network gaps. Excluding diverse stakeholders and beneficiaries from the decision-making process can lead to missed insights, resulting in solutions that fail to identify systemic needs and potentially waste resources or duplicate efforts.
To implement this, include an extended Voice of Stakeholder Analysis:
- Map key stakeholders to identify a wider variety and greater number of people who interact with the problem, especially the beneficiaries and frontline staff most closely involved.
- Build bridges and communication channels, for instance, facilitating roundtable discussions and workshops to bridge cross-sector gaps.
- Be prepared to incentivize time and participation. Underserved groups, in particular, often have limited resources and time.
Example
You organize a series of meetings with local educators, technology industry leaders, community organizers, and students. During these discussions, you might discover that while there is a strong desire among students to enter the technology field, many lack the practical skills and industry connections needed to secure entry-level positions. This reveals a systemic insight: the same issues are repeated across multiple students and groups, but not enough is being done to solve them. This insight, which might have been missed if you had relied solely on educational experts, helps you refine your focus to address this specific gap between education and employment in the technology sector.
For a related piece on engaging with stakeholders, check out:
Third, Investigate Systemic Patterns And Uncover Root Causes
Many philanthropists address visible symptoms, leading to short-term fixes instead of lasting change. This often stems a lack of systems thinking, which involves understanding how elements within a system connect and the deeper root causes of key issues. Without this, solutions may not address core issues, resulting in ineffective interventions that don't align with people's experiences.
Therefore, a more effective strategy thoroughly investigates root causes to uncover systemic patterns. This helps develop better solutions by revealing underlying mechanisms and constraints. By considering the broader context and individuals' experiences, efforts can address fundamental issues, creating real results.
To implement this strategy, refine your Problem Prioritization Matrix:
- Stratify Your Outreach Sample: When evaluating finalists, improve validity by engaging a stratified sample to get a balanced perspective aligned with your goals (e.g., nontechnical nonprofits left behind in the AI wave). Focus outreach on groups like those thriving in the AI wave and those struggling. Differences among these groups ensure interventions have broad applicability and address diverse needs, revealing how systemic issues affect variations within your niche.
- Map Key Workflows: Map the key workflows beneficiaries use to achieve their goals, identifying challenging steps. This reveals bottlenecks and inefficiencies, pinpointing where targeted interventions can create the greatest impact.
- Analyze Past Attempts: Analyze previous efforts to address key issues and identify unresolved challenges. Learning from past failures and successes helps avoid repeating ineffective strategies and supports developing effective solutions.
- Define Success Metrics: Establish success metrics from the beneficiary's perspective to guide solution development, impact measurement, and continuous improvement. This ensures solutions address actual needs and preferences, aligning interventions with real-world impact and adoption.
- Identify Needs and Bright Spots: Identify desired skills, resources, or tools, and highlight existing successes to uncover constraints and potential solutions. Understanding gaps and strengths enables targeted interventions that leverage what’s already working.
Example
When investigating the education-to-employment pipeline in your community's tech sector, you might uncover systemic issues like outdated curricula, lack of industry-education partnerships, and limited real-world tech exposure for students.
This reveals that providing coding classes alone is insufficient; a connected ecosystem needs to evolve for lasting change.
For a deeper dive into these concepts:
Sprint 3: Strategic Giving Refines Viable Solutions That Build Trust
First, Define What a “Good” Solution Means
Philanthropy often faces the misconception that solutions must be entirely novel or comprehensive to be effective. This belief can lead to overlooking successful initiatives and wasting resources due to incorrect assumptions.
Instead, start by enhancing or scaling proven solutions and workflows. This allows for immediate impact, faster trust-building, and increased collaboration. By starting with established methods, you can achieve quick wins for your beneficiaries, which provide a foundation for understanding complex problems and testing newer or more comprehensive solutions.
To implement this strategy, build a Solutions Prioritization Matrix:
- Define clear criteria: For a "good" solution in your context, consider three factors: depth of impact, viability (speed to desired impact on success metric, cost/complexity, and alignment with your unique strengths and experiences), and evidence quality of your scores. Defining clear criteria ensures that you're evaluating solutions based on what truly matters for your specific goals and resources, preventing you from chasing superficial or unsustainable initiatives.
For a deeper dive into these criteria, examples, and secondary criteria that help you clarify effective from mediocre solutions, check out: How To Eliminate Chaos With Backlog Prioritization
- Find validated initiatives tackling similar problems: Including those in adjacent fields and different sectors — that have shown promise in addressing similar problems. Understanding what's already working allows you to build on existing successes and avoid reinventing the wheel, saving time and resources.
- Brainstorm and Personalize: Enhance and customize validated solutions to your unique problem context, looking more deeply into viability, radically reducing the scope and complexity of your solution, even at the sacrifice of scalability but without sacrificing value, to build a “minimum lovable prototype.”
Example
In our scenario, you develop criteria for effective solutions, including depth, viability, and evidence quality on both education and employment outcomes. Then, you discover an existing mentorship program that has shown promising results but lacks resources to expand, instead of creating a new program from scratch, consider partnering with this initiative, bringing your tech industry connections and resources to significantly enhance and scale their efforts, enabling you to provide immediate value and build trust.
For more on brainstorming prototypes and reducing scope creep, see
Second, Begin Solution Exploration Early
A common mistake in strategic giving is delaying solution development until after extensive problem analysis. Many philanthropists attempt to solve this by conducting exhaustive research before considering any solutions. However, this approach often leads to missed opportunities for early impact and failure to adapt to an evolving understanding of the problem.
Waiting too long to explore solutions can result in interventions that are outdated or ineffective by the time they are implemented. You might also spend significant resources building a solution only to find it was not the right one, slowing down learning cycles and wasting time.
Instead, beginning solution exploration early and continuously revising allows for rapid learning and adaptation. This approach ensures that your solutions evolve alongside your understanding of the problem, leading to more effective and targeted interventions.
To implement this strategy, try an Offer Creation Project:
- Brainstorm Solution Formats: Start early in problem exploration, evaluating them based on stakeholder feedback. Consider broad formats (e.g., guides, workshops, AI tools) to maintain flexibility while refining your understanding of the problem. Use proven formats when possible to reduce complexity, cost, and time to impact.
- Refine for Viability. Build off existing validated solutions you can access where possible to simplify and accelerate time to impact. Sequence your bigger ideas until after you’ve built a basic trustworthy platform.
- Create clear positioning. This is core messaging that explains your offer, how it solves problems, and is backed by evidence of effectiveness.
Example
As you explore the education-to-employment gap in the tech sector, you begin brainstorming solution formats early.
For instance, you organize a weekend coding bootcamp for high school students, inviting local tech professionals as mentors. You use surveys and feedback from participants to identify bright spots—such as the effectiveness of hands-on mentorship—and areas for improvement. You might discover that while technical skills are valuable, soft skills like communication and problem-solving are equally critical for success in the tech industry.
This feedback allows you to iterate on your solution format, expanding it to include workshops on soft skill development alongside coding sessions. By starting small and refining your offerings based on real-world insights, you can create a program that addresses both technical and interpersonal skill gaps, ensuring it meets the needs of both students and employers in your community.
More on Positioning and Offer creation:
Finally, Validate and Continuously Improve Your Impact
A common mistake is viewing impact as a one-time achievement rather than an ongoing process. Effective philanthropy requires continuous improvement and maintenance.
To validate and enhance your impact, adopt an Impact Validation & Refinement Process:
- Validate quickly: Gather concrete commitments rather than mere expressions of interest and refine your offering based on feedback.
- Map and optimize the journey: identify the key steps in your workflow, and the key bottlenecks, helping your beneficiaries get to value faster. The faster and consistently you help large volumes of your niche exceed their success target, the more raving fans (and organic referrals and growth) you will get.
- Continuous impact measurement and evaluation: Use these insights to continuously prioritize your problem and solution prioritization matrix to maximize your resources for impact.
By embracing this cycle of validation and improvement, you ensure your efforts remain relevant, effective, and truly impactful over time.
Example
After developing your combined technical and soft skills program, launch a small-scale pilot with 20 high school students. Define your north star metric as the percentage of participants who secure tech internships within six months of completion. To validate impact, gather concrete commitments from local tech companies to interview program graduates. Implement a robust evaluation system, tracking not only internship placements but also participants' skill growth and employer feedback.
As you run the pilot, continuously map the student journey from program awareness to post-internship success. Use surveys, interviews, and performance data to identify areas for improvement. For instance, you might discover that students struggle to apply their skills in real-world scenarios. In response, iterate on your curriculum to include more project-based learning and mock interviews with tech professionals. This cycle of measurement, analysis, and refinement ensures your program remains effective and aligned with both student needs and industry demands.
For more on some of these concepts:
- Commitments:48 hour Business Validation for Innovators
Strategic Giving: Maximizing Impact
As we've explored, our twist on strategic giving offers a powerful framework for maximizing the impact of philanthropic efforts. It challenges us to think critically about our assumptions, to base our decisions on both quantitative and qualitative evidence, and to constantly seek ways to increase our impact. While the path may not always be easy, the potential to create meaningful, lasting change makes it immensely rewarding.
Looking for a quick overview of how to maximize your philanthropic impact from this piece? Check out this Philanthropic Strategy: Three Easy-to-Miss Tips for Impact (One Pager). It's your go-to resource for applying effective altruism to strategic giving.
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Strategic Giving: FAQs
What is strategic giving, and why is it important?
Strategic giving is a deliberate approach to philanthropy that prioritizes thoughtful problem selection and effective solution development to maximize impact. It's important because it avoids common pitfalls like rushing into solutions without fully understanding the problem, which can lead to wasted resources and potential harm. Strategic giving helps donors align their resources and passions with the most pressing needs. For example, instead of blindly funding a popular cause, strategic giving encourages a tech entrepreneur to research community education needs and leverage their unique tech skills to create innovative solutions.
How does strategic giving differ from traditional philanthropy?
Strategic giving emphasizes higher levels of donor engagement, rooted in their goals and strengths. It encourages donors to consider evidence quality, systemic issues, and building off and personalizing validated solutions. It is ultimately a people and problem focused approach.
What are the key steps involved in developing a Strategic Giving plan?
The provided framework outlines a three-sprint approach. First, identify meaningful problems by understanding yourself and others. Second, explore and evaluate a wide variety of problems by seeking diverse perspectives and investigating root causes. Following both these steps is key to ensuring that you are actually investing in areas that are urgent, unmet, and core problems that people face. Then, focus on viable solutions that build trust by validating their impact and fostering collaboration with the people being served. Following the three-sprint process, you might want to start by reviewing existing reports on education and employment in your community for quick feedback.
How can I avoid common pitfalls when practicing strategic giving?
Several pitfalls can hinder effective strategic giving. These include rushing to implement solutions, adopting a generic approach without considering unique strengths, and succumbing to quantification bias by focusing solely on easily measurable outcomes. By reflecting on personal purpose, prioritizing problem-position fit, and focusing on unmet, core needs, you can address challenges more holistically. One way to tackle these risks is to start with reflection and brainstorming, and define the goals before diving in to identify what is important to solve.
How can I measure the impact of my Strategic Giving efforts?
Measuring impact in strategic giving goes beyond simple metrics like dollars spent or people served. It requires a focus on qualitative factors, continuous evaluation, and aligning solutions with beneficiary needs. In order to analyze how helpful the action is, establish success metrics from the beneficiary's perspective to guide solution development, impact measurement, and continuous improvement. By mapping beneficiary journeys and continuously measuring outcomes, you can ensure your efforts remain relevant, effective, and impactful over the long term.
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