Director of Planned Giving

Ryan Mahoney

Why this role is hard · Ryan Mahoney

Finding a manager for planned giving means looking for someone who can turn unspoken donor worries about heirs into actual gifts without stepping outside compliance rules. You need people who pick up on what families do not say out loud. They have to navigate dense estate information while keeping the conversation focused on people rather than paperwork. The ones who excel at building rapport tend to skim the details, while those obsessed with regulations often feel cold and slow things down. You are really looking for patience and precision, plus the calm to wait out complicated gift setups until they fit.

Core Evaluation

Critical questions for this role

The competency and attitude questions below are where the hiring decision is made. They run in the live interview rounds and are calibrated to the level selected above.

17 Competency Questions

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  1. Discipline

    Donor Strategy and Relationship Management

  2. Job requirement

    Campaign Design and Legacy Programming

    Coordinates event logistics, manages mailing lists, and distributes standardized campaign collateral to target audiences.

  3. Expected at Junior

    While tactical execution is required, campaign architecture and ROI optimization belong to higher levels; managers independently run logistics and distribution within approved frameworks.

Interview round: Hiring Manager Technical Review

Walk me through how you organized and executed a legacy giving seminar or webinar from initial planning through post-event follow-up. What metrics did you track?

Positive indicators

  • Details a clear timeline from planning to execution
  • Explains audience segmentation strategy for outreach
  • References specific attendance or conversion metrics

Negative indicators

  • Focuses only on event day logistics, ignoring planning/follow-up
  • Uses unsegmented or outdated mailing lists
  • Cannot identify how attendance or engagement was measured

12 Attitude Questions

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Active Listening

Active listening is the disciplined practice of fully concentrating on, comprehending, and thoughtfully responding to verbal and non-verbal communication while suspending immediate judgment or premature problem-solving. In a strategic leadership context, it involves accurately capturing underlying motivations, emotional undercurrents, and operational nuances from diverse stakeholders, thereby fostering psychological safety, aligning cross-functional efforts, and informing evidence-based decision-making.

Interview round: Recruiter Screen

What steps do you take to ensure accurate documentation of a donor's stated intentions before they conclude a meeting?

Positive indicators

  • Uses explicit confirmation steps before ending conversation
  • Separates facts from interpretations in documentation
  • Mentions timestamping and version control for updates
  • Aligns notes with institutional data standards
  • Plans follow-up to validate understanding

Negative indicators

  • Relies entirely on memory for post-meeting documentation
  • Documents assumptions instead of stated facts
  • Skips verification steps to save time
  • Uses inconsistent or vague terminology in records
  • Fails to connect notes to actionable next steps

Supporting Evaluation

How candidates earn the selection conversation

The goal is to reduce effort for everyone by collecting more useful signal before adding more interviews. Lightweight application prompts and structured screens help the panel focus live time on the candidates most likely to succeed.

Stage 1 · Application

Filter at the door

Runs the moment a candidate hits Submit. Disqualifying answers end the application; everything else is captured for review.

Video-Response Questions

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Application Screen: Video Response

Describe how you would conduct an initial discovery call with a mid-tier prospect who is hesitant to discuss legacy gifts due to family financial anxiety. What specific questions would you ask, and how would you adjust your approach based on their verbal and non-verbal cues?

Candidate experience

REC
0:42 / 2:00
1Record
2Review
3Submit

Response time

2 min

Format

Recorded video

Stage 2 · Resume Screening

Read the resume against fixed criteria

Reviewers score every application that clears the door against the same criteria. Stronger reviews advance to live interviews; weaker ones are archived without further screening.

Resume Review Criteria

8 criteria
Evidence of managing individual donor relationships and executing tactical outreach for mid-tier legacy prospects, including tracking interactions and converting interest into documented expectancies.
Evidence of maintaining pipeline accuracy, running data hygiene audits, and supporting leadership reporting through CRM tools and workflow automation.
Evidence of drafting compliant bequest language, designing multi-channel outreach materials, and optimizing donor touchpoints and pledge experiences.
Evidence of coaching frontline staff on legacy identification and coordinating with external financial or legal advisors to resolve complex donor requests.

Does the cover letter or personal statement convey clear relevance and familiarity with the job?

Does the resume indicate required academic credentials, relevant certifications, or necessary training?

Is the resume complete, well-organized, and free from formatting, spelling, and grammar mistakes?

Does the resume show relevant prior work experience?

Stage 3 · During Interviews

Where the hire is decided

Interview rounds use the competency and attitude questions outlined above, then add tests, work simulations, and presentations that reveal deeper evidence about how the candidate thinks and works.

Presentation Prompt

Walk us through your approach to designing and executing a mid-tier legacy prospect cultivation campaign. Discuss how you balance high-volume tactical execution with the patience required for deeply personal donor interactions, and explain how you coach frontline major gift officers to navigate these conversations effectively.

Format

deck-and-walkthrough · 20 min · ~2 hr prep

Audience

Hiring manager, senior development staff, and a compliance representative

What to prepare

  • A 5-7 slide deck outlining a past or hypothetical campaign strategy
  • Key touchpoint mapping and coaching framework for frontline staff
  • Metrics used to track conversion and donor readiness

Deliverables

  • A short verbal walkthrough of your prepared deck
  • A structured Q&A on donor engagement tactics, pacing, and cross-departmental alignment

Ground rules

  • Use only work you are permitted to share; anonymize all donor names and sensitive financial details
  • Focus on process, framing, and stakeholder management rather than proprietary campaign assets
  • Do not draft new campaign materials during preparation; rely on existing or hypothetical examples

Scoring anchors

Exceeds
Presents a sophisticated, empathetic cultivation model with clear coaching mechanisms, robust metrics, and proactive boundary management that elevates team capability and donor trust.
Meets
Outlines a logical campaign workflow with reasonable coaching touchpoints and standard metrics, showing adequate understanding of donor pacing and team alignment.
Below
Proposes a transactional, high-pressure approach with vague coaching guidance, ignores donor emotional cues, and lacks clear role boundaries or compliance awareness.

Response time

20 min

Positive indicators

  • Articulates a clear, donor-centric cultivation framework that respects emotional pacing
  • Demonstrates structured coaching methods for frontline staff
  • Balances campaign metrics with qualitative relationship signals
  • Proactively addresses cross-departmental friction and defines clear role boundaries

Negative indicators

  • Prioritizes volume over donor readiness or emotional safety
  • Relies on rigid scripts without adaptability to donor cues
  • Fails to define clear handoffs or scope boundaries with major gift officers
  • Dismisses compliance or ethical guardrails in pursuit of conversion speed

Work Simulation Scenario

Scenario. You are conducting a scheduled 1:1 discovery call with a prospective donor who has expressed initial interest in a charitable gift annuity but has not yet committed. The donor is navigating complex family dynamics and has expressed anxiety about how a planned gift might impact their heirs.

Problem to solve. Guide the conversation to uncover the donor's true legacy motivations, validate their emotional concerns, and clearly establish the boundaries of your advisory role without offering direct tax or legal counsel.

Format

stakeholder-roleplay · 40 min · ~2 hr prep

Success criteria

  • Elicit high-information details about donor intent and family context through targeted, empathetic questioning
  • Clearly delineate the organization's advisory scope and recommend appropriate external counsel
  • Maintain psychological safety while steering the conversation toward next steps in the cultivation pipeline

What to review beforehand

  • Charitable Gift Annuity basics and typical donor concerns
  • Organizational gift acceptance policy boundaries
  • Active listening and professional boundary-setting frameworks

Ground rules

  • You will drive the conversation; the role player will respond authentically
  • Do not draft a financial plan or provide legal/tax advice
  • Focus on discovery, empathy, and boundary management in real time

Roles in scenario

Prospective Donor (customer, played by hiring_manager)

Motivation. Wants to leave a meaningful legacy but is deeply anxious about family conflict, tax implications, and losing control over assets.

Constraints

  • Will not share full financial details unless asked directly and respectfully
  • Has received conflicting advice from a sibling's financial advisor
  • Expects the conversation to remain confidential and emotionally safe

Tensions to introduce

  • Express hesitation about locking funds away permanently
  • Ask for specific tax deduction percentages and legal structuring advice
  • Share a vulnerable story about family disagreement over estate planning

In-character guidance

  • Answer honestly and directly when asked clarifying questions
  • Show emotional vulnerability when the candidate demonstrates genuine empathy
  • Gradually reveal deeper concerns as trust builds through the conversation

Do not

  • Do not volunteer unasked financial or legal details
  • Do not escalate hostility or become defensive
  • Do not solve the problem for the candidate or coach them toward a specific answer

Scoring anchors

Exceeds
Seamlessly balances deep empathetic inquiry with firm, respectful boundary-setting; surfaces unspoken donor motivations and co-creates a clear, compliant next-step pathway without overpromising.
Meets
Asks relevant clarifying questions, acknowledges emotional context, and clearly states advisory limits; guides the conversation toward appropriate next steps with minor pacing or framing gaps.
Below
Interrupts, gives unauthorized legal/tax advice, ignores family dynamics, or fails to establish professional boundaries, leaving the donor relationship or compliance posture exposed.

Response time

40 min

Positive indicators

  • Asks high-information clarifying questions to uncover underlying donor motivations
  • Validates emotional concerns without minimizing or rushing past family dynamics
  • Clearly articulates advisory boundaries and recommends appropriate external counsel
  • Structures a logical next-step pathway aligned with donor readiness and organizational process

Negative indicators

  • Interrupts or dismisses expressed family anxieties and legacy concerns
  • Provides direct tax, legal, or financial structuring advice outside professional scope
  • Fails to establish clear boundaries when pressed for non-advisory guidance
  • Rushes to close or pitch a specific product before establishing donor trust and intent

Progression Framework

This table shows how competencies evolve across experience levels. Each cell shows competency at that level.

Donor Strategy and Relationship Management

4 competencies

CompetencyJuniorMidSeniorPrincipal
Campaign Design and Legacy Programming

Coordinates event logistics, manages mailing lists, and distributes standardized campaign collateral to target audiences.

Designs campaign narratives, oversees creative asset production, and measures program ROI to optimize legacy society engagement.

Scales multi-year programming across geographic regions, integrates legacy messaging into broader brand strategy, and manages cross-functional campaign teams.

Defines institutional brand positioning for planned giving, secures executive sponsorship for major initiatives, and shapes national legacy giving trends.

Community Partnerships and Institutional Alliances

Attends local networking events, maintains advisor contact lists, and distributes educational materials to referral partners.

Builds formal advisor councils, negotiates partnership MOUs, and co-hosts educational seminars with professional networks.

Scales institutional alliances across sectors, aligns partnership initiatives with organizational mission, and evaluates network ROI.

Chairs national professional advisor networks, shapes strategic ecosystem partnerships, and represents the organization in cross-sector philanthropy coalitions.

Donor Cultivation and Engagement Strategy

Executes targeted outreach sequences, schedules discovery meetings, and maintains accurate engagement logs in CRM systems.

Designs multi-channel cultivation strategies, segments donor portfolios, and mentors staff on advanced relationship-building techniques.

Aligns engagement frameworks with institutional fundraising goals, optimizes resource allocation across regions, and establishes enterprise-level donor journey standards.

Sets industry benchmarks for donor experience, champions innovative engagement models, and represents the organization at national philanthropy forums.

Gift Structuring and Financial Advisory

Prepares preliminary gift illustrations, coordinates with legal counsel, and explains basic planned giving options to prospects.

Oversees the structuring of multi-asset gifts, ensures accurate financial modeling, and manages relationships with external tax and estate advisors.

Integrates financial planning into institutional wealth transfer strategy, develops gift acceptance protocols, and guides complex negotiation scenarios.

Influences tax policy advocacy, establishes national standards for charitable financial planning, and directs high-net-worth portfolio strategy.

Operational Infrastructure and Compliance

4 competencies

CompetencyJuniorMidSeniorPrincipal
Data Architecture and CRM Management

Performs routine data entry, runs standard reports, and troubleshoots basic CRM configuration issues to maintain data hygiene.

Architects data models and segmentation rules, oversees system upgrades, and implements advanced analytics dashboards for team use.

Establishes enterprise data governance frameworks, ensures cross-departmental data alignment, and drives analytics maturity across the organization.

Champions predictive modeling and AI-driven donor insights, sets institutional data strategy, and influences sector standards for nonprofit data infrastructure.

Digital Integration and System Interoperability

Configures basic integrations, monitors API sync logs, and troubleshoots workflow automation errors in day-to-day operations.

Selects and implements core tech stack components, manages vendor partnerships, and designs interoperable workflows across fundraising systems.

Drives digital transformation roadmaps, aligns system architecture with enterprise IT strategy, and oversees large-scale platform migrations.

Evaluates emerging technology investments, sets institutional interoperability standards, and leads cross-industry tech innovation initiatives in philanthropy.

Regulatory Compliance and Risk Management

Monitors gift acceptance logs, maintains compliance documentation, and flags regulatory discrepancies for review.

Manages audit readiness, conducts periodic risk assessments, and updates internal policies to reflect changing regulatory landscapes.

Establishes enterprise compliance frameworks, aligns risk management with institutional strategy, and reports directly to executive leadership on compliance posture.

Navigates complex multi-jurisdictional regulatory environments, shapes sector-wide compliance standards, and leads crisis management protocols for high-stakes compliance events.

Strategic Governance and Board Relations

Prepares committee briefing materials, tracks policy implementation status, and compiles operational metrics for leadership review.

Facilitates board and committee strategy sessions, drafts governance frameworks, and ensures alignment between operational outputs and board directives.

Aligns planned giving governance with institutional mission and risk appetite, chairs executive steering committees, and manages high-level stakeholder communications.

Defines sector governance models, advises trustees on long-term philanthropic strategy, and represents the organization in national policy and governance dialogues.