Nonprofit FundraisingExpert-built kit

Director of Planned Giving

Plans multi-channel legacy campaigns, crafts bequest messaging, and tracks donor conversion metrics.

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Interview content for Director of Planned Giving

30
What to ask. Competency and attitude questions, assigned to the right round.
248
What to listen for. Positive and negative indicators, per question.
8
What the hire must do. Capabilities with expected proficiency at each level.

Look inside: one question, as it appears in the kit

Pick the level you’re hiring. The sample changes with the level you select.

Round 2 · Hiring Manager Technical17 competency questions

Donor Strategy and Relationship Management

Campaign Design and Legacy Programming

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

Expected at Director of Planned Giving

Sample competency question

Walk through the development and execution of a legacy giving campaign that successfully increased donor engagement.

Ask once, as written, then allow silence. A helpful rephrase may hand the candidate the answer.

Positive indicators

  • Defines clear objectives with measurable baseline metrics
  • Develops tested narrative frameworks aligned with donor psychology
  • Deploys consistent messaging across multiple communication channels
  • Tracks performance and adjusts tactics based on engagement data
  • Calculates ROI linking campaign spend to qualified prospect outcomes

Negative indicators

  • Launches campaigns without clear objectives or baseline metrics
  • Uses untested messaging that lacks donor resonance
  • Deploys assets inconsistently across communication channels
  • Ignores performance data during campaign execution
  • Cannot articulate ROI or cost-per-acquisition metrics

Directors need independent proficiency to align campaigns with revenue goals, but execution is often shared with marketing teams, making it a valuable growth area rather than a core must.

Ryan Mahoney

Why this role is hard · Ryan Mahoney

Hiring a director of planned giving requires finding someone who combines genuine empathy with sharp organizational skills. You need a person who can listen past a donor’s worries about taxes and turn those concerns into a workable charitable remainder trust. The real challenge is telling apart candidates who actually build long-term relationships from those who just memorize campaign scripts. I have seen strong interview performers fall apart when asked to walk through a complex gift structure under changing estate tax rules. You are looking for a steady leader who can manage high-net-worth families, connect legacy gifts with broader fundraising goals, and keep a small team on track.

Everything in the download, in the order you’ll use it

Level guides for Manager of Planned Giving, Director of Planned Giving, Senior Director of Planned Giving and Vice President of Planned Giving.

Before you post

  • 1Ready-to-use job description
  • 3Video screening prompts
  • 8Resume screening criteria

In the room

  • 17Competency interview questions
  • 13Attitude interview questions
  • 1Hands-on work simulations
  • 1Presentation prompts

At the debrief

  • Progression framework
  • Exceeds / Meets / Below anchors for every exercise
  • 3Interview plan with time per round

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

1 of 17

  1. Discipline

    Donor Strategy and Relationship Management

  2. Job requirement

    Campaign Design and Legacy Programming

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

  3. Expected at Director of Planned Giving

    Directors need independent proficiency to align campaigns with revenue goals, but execution is often shared with marketing teams, making it a valuable growth area rather than a core must.

Interview round: Hiring Manager Technical

Walk through the development and execution of a legacy giving campaign that successfully increased donor engagement.

Positive indicators

  • Defines clear objectives with measurable baseline metrics
  • Develops tested narrative frameworks aligned with donor psychology
  • Deploys consistent messaging across multiple communication channels
  • Tracks performance and adjusts tactics based on engagement data
  • Calculates ROI linking campaign spend to qualified prospect outcomes

Negative indicators

  • Launches campaigns without clear objectives or baseline metrics
  • Uses untested messaging that lacks donor resonance
  • Deploys assets inconsistently across communication channels
  • Ignores performance data during campaign execution
  • Cannot articulate ROI or cost-per-acquisition metrics

13 Attitude Questions

1 of 13

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: Hiring Manager Technical

Describe your process for gathering and synthesizing unspoken team concerns before finalizing a multi-year legacy campaign strategy.

Positive indicators

  • Uses multiple channels to capture both vocal and silent feedback.
  • Translates concerns into measurable capacity adjustments.
  • Closes the loop by sharing strategy modifications with staff.

Negative indicators

  • Relies solely on formal meetings where junior staff stay quiet.
  • Treats team feedback as a formality rather than a strategic input.
  • Finalizes plans without addressing identified capacity bottlenecks.

Supporting Evaluation

How candidates earn the selection conversation

The goal is to reduce effort for everyone by collecting more useful signals before adding more interviews. Lightweight application prompts and structured screens help your team focus interview 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

1 of 3

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 setting departmental goals, designing KPI dashboards, and defining metrics for planned giving pipeline velocity and multi-year forecasting.
Evidence of evaluating life-income gift structures, ensuring regulatory compliance, and standardizing trust acceptance protocols through SOP development.
Evidence of designing targeted bequest expectancy campaigns, mapping donor lifecycle touchpoints, and implementing marketing automation systems.
Evidence of managing staff resources, delivering training programs, and aligning planned giving workflows with broader fundraising operations.

Does the resume show relevant prior work experience?

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

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

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

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

Discuss your approach to aligning disparate departmental incentives around shared legacy revenue targets while designing compliant, donor-appropriate gift structures that balance institutional risk management with client flexibility. Frame the strategic problem, walk through your reasoning on tradeoffs, and present your recommended approach.

Format

strategic-brief · 60 min · ~8 hr prep

Audience

Executive leadership, legal counsel, and board finance committee members

What to prepare

  • A structured strategic brief (slides or talking points) analyzing the tension between revenue goals, compliance constraints, and donor flexibility
  • A proposed framework for gift structuring and departmental alignment
  • Anticipated implementation risks and mitigation strategies

Deliverables

  • A 30-minute strategic walkthrough of your brief and reasoning
  • A 30-minute defense of tradeoffs, risk boundaries, and cross-functional alignment mechanisms

Ground rules

  • Do not present net-new strategic artifacts, proprietary financial models, or unvetted policy drafts
  • Focus on your reasoning, framing, and how you would navigate executive alignment and risk tradeoffs
  • Use anonymized examples from past work or clearly labeled hypothetical scenarios

Scoring anchors

Exceeds
Frames the strategic dilemma with exceptional clarity, presents a highly adaptable gift structuring framework that elegantly balances donor flexibility with institutional risk, and demonstrates masterful cross-functional alignment strategies.
Meets
Identifies key tensions between revenue and compliance, proposes a reasonable gift structuring approach with clear risk boundaries, and outlines a practical path for departmental alignment.
Below
Presents a one-dimensional or overly aggressive revenue strategy, ignores fiduciary or compliance constraints, lacks a coherent alignment mechanism, and struggles to defend tradeoffs under questioning.

Response time

60 min

Positive indicators

  • Clearly frames the strategic tension between revenue goals and compliance/risk
  • Articulates nuanced gift structuring tradeoffs with donor-centric and institutional safeguards
  • Demonstrates a systematic approach to cross-departmental alignment and incentive design
  • Anticipates regulatory pitfalls and builds proactive mitigation into the framework

Negative indicators

  • Jumps to a rigid solution without acknowledging structural tensions or tradeoffs
  • Overlooks compliance or fiduciary constraints in favor of short-term revenue targets
  • Fails to propose a clear mechanism for aligning competing departmental incentives
  • Uses overly technical jargon without translating implications for executive decision-making

Work Simulation Scenario

Scenario. You are finalizing a complex charitable remainder trust with a family foundation. The institutional trustee is pushing for highly flexible payout structures and expedited asset transfers that conflict with your organization's reserve funding policy and actuarial compliance standards.

Problem to solve. Negotiate gift terms that honor the donor's intent and relationship value while strictly adhering to fiduciary duty, reserve requirements, and regulatory compliance. Drive to a mutually acceptable agreement or clearly articulate a compliant alternative.

Format

negotiation · 75 min · ~6 hr prep

Success criteria

  • Frame compliance constraints transparently without triggering adversarial dynamics
  • Propose structurally sound alternatives that preserve donor value within policy limits
  • Secure explicit alignment on payout mechanics, reserve funding, and execution timelines

What to review beforehand

  • Charitable Remainder Trust payout regulations and reserve funding principles
  • Actuarial compliance thresholds and non-negotiable fiduciary standards
  • Negotiation frameworks for balancing donor flexibility with institutional risk

Ground rules

  • You will facilitate the negotiation and drive toward a compliant resolution
  • Focus on tradeoff framing, structural creativity, and relationship preservation
  • Do not draft binding legal documents during the session

Roles in scenario

Institutional Trustee (external_partner, played by leadership)

Motivation. Wants to maximize donor flexibility and expedite the gift to satisfy foundation board expectations.

Constraints

  • Cannot commit to structures that lack clear liquidity timelines
  • Faces pressure from foundation beneficiaries for higher payout certainty
  • Values long-term partnership but will walk away if terms feel overly restrictive

Tensions to introduce

  • Request payout rates that exceed standard actuarial limits
  • Push for accelerated asset transfer before reserve validation is complete
  • Question whether organizational compliance rules are unnecessarily rigid

In-character guidance

  • Answer honestly about foundation constraints and timeline pressures
  • Remain open to structurally creative alternatives that respect fiduciary limits
  • Signal willingness to compromise if compliance and risk are addressed transparently

Do not

  • Do not concede on non-negotiable reserve or compliance requirements
  • Do not escalate hostility or use ultimatums
  • Do not volunteer alternative payout models the candidate could propose

Chief Financial Officer (cross_functional_partner, played by cross_functional)

Motivation. Protect institutional reserves, ensure actuarial compliance, and prevent liquidity shortfalls from complex trust structures.

Constraints

  • Must enforce strict reserve funding thresholds per board policy
  • Will not approve gifts without verified asset liquidity and payout sustainability modeling
  • Requires clear documentation and audit trails before execution

Tensions to introduce

  • Flag compliance risks in the trustee's proposed payout schedule
  • Insist on extended validation timelines before asset acceptance
  • Demand explicit structural guardrails to protect institutional balance sheets

In-character guidance

  • Provide honest actuarial and reserve constraints when asked
  • Support structurally sound compromises that maintain fiduciary integrity
  • Clarify non-negotiable policy boundaries without micromanaging the negotiation

Do not

  • Do not override the candidate's negotiation authority
  • Do not solve the structural problem for the candidate
  • Do not escalate into departmental conflict or hostile pushback

Scoring anchors

Exceeds
Masterfully navigates fiduciary constraints while preserving donor trust; engineers compliant structural alternatives, secures explicit alignment on reserve mechanics, and documents clear execution guardrails.
Meets
Clearly communicates compliance limits, proposes reasonable alternatives, and moves toward a compliant agreement with minor gaps in timeline documentation or structural precision.
Below
Concedes on critical reserve policies, triggers adversarial dynamics, or leaves payout mechanics and compliance thresholds ambiguously defined, exposing the organization to fiduciary risk.

Response time

75 min

Positive indicators

  • Transparently frames compliance and reserve constraints without triggering adversarial dynamics
  • Proposes structurally sound alternatives that preserve donor intent within policy limits
  • Drives explicit alignment on payout mechanics, validation timelines, and documentation requirements
  • Balances relationship preservation with firm enforcement of fiduciary guardrails

Negative indicators

  • Concedes on non-negotiable compliance or reserve thresholds to appease the trustee
  • Uses adversarial or rigid language that fractures partnership rapport
  • Fails to articulate clear structural alternatives or documentation requirements
  • Allows vague commitments that expose the organization to actuarial or liquidity risk

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

CompetencyManager of Planned GivingDirector of Planned GivingSenior Director of Planned GivingVice President of Planned Giving
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

CompetencyManager of Planned GivingDirector of Planned GivingSenior Director of Planned GivingVice President of Planned Giving
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.