Planned Giving Officer

Ryan Mahoney

Why this role is hard · Ryan Mahoney

Hiring an entry level planned giving specialist means telling the difference between real donor connection and practiced sales talk. You want someone who can listen through a prospect’s worries about leaving behind assets while keeping appropriate professional boundaries. We often mistake loud self assurance for actual ability, so watch for candidates who stay calm during practice calls and know when to pass complicated gift questions upward instead of making empty promises. This job also requires careful record keeping in our donor systems and straightforward writing.

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 & Gift Planning

  2. Job requirement

    Donor Prospect Cultivation & Relationship Management

    Supports cultivation activities by preparing communications, scheduling meetings, and maintaining contact logs to ensure seamless prospect pipeline progression.

  3. Expected at Junior

    Core to the specialist's mandate of qualifying leads and supporting outreach; requires basic working proficiency to manage routine scheduling and communication tracking reliably.

Interview round: Hiring Manager Technical: Strategy & Technical Expertise

Walk me through how you coordinated a series of donor discovery meetings when scheduling conflicts arose with multiple stakeholders.

Positive indicators

  • References CRM logging and calendar management
  • Mentions clear stakeholder communication protocols
  • Describes a structured follow-up process
  • Aligns actions with organizational SOPs

Negative indicators

  • Relies on memory instead of tracking tools
  • Misses follow-up documentation steps
  • Does not mention conflict resolution strategies
  • Ignoes SOP guidelines for meeting coordination

12 Attitude Questions

1 of 12

Active Listening

The disciplined cognitive and interpersonal practice of fully concentrating on, comprehending, and responding to both explicit statements and implicit nonverbal cues while suspending premature judgment. In planned giving, it entails strategically decoding underlying values, emotional undercurrents, and familial dynamics to accurately align legacy intentions with appropriate philanthropic structures.

Interview round: Cross-Functional Collaboration: Execution & Stakeholder Alignment

Imagine you are taking notes during a fast-paced donor webinar and the speaker covers multiple eligibility criteria rapidly. What process would you use to ensure accurate documentation?

Positive indicators

  • Mentions post-session verification process
  • Uses structured templates to capture criteria
  • Acknowledges limits and seeks clarification

Negative indicators

  • Tries to write everything down and misses context
  • Enters unverified notes directly into CRM
  • Assumes they can recall details accurately later

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

1 of 3

Application Screen: Video Response

You are guiding a prospective donor through a complex legacy planning discussion when their adult children voice conflicting inheritance expectations that clash with the proposed gift structure. Describe exactly how you would facilitate this multi-stakeholder conversation to validate the donor’s vision, maintain neutral professional boundaries, and clarify institutional next steps.

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 configuring automated stewardship sequences, maintaining accurate donor expectancies in CRM systems, and implementing validation protocols to ensure data integrity for deferred gift tracking.
Evidence of analyzing wealth indicators and donor portfolios to identify legacy potential, utilizing screening platforms to generate qualified leads for major gift officers.
Evidence of coordinating planned giving workshops and community seminars, managing speaker logistics, and producing marketing collateral to educate prospects on deferred vehicles.
Evidence of maintaining secure documentation trails, reviewing beneficiary forms for accuracy, and supporting legal/finance teams during gift acceptance reviews.

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

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?

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 an early-stage prospect qualification campaign for a new legacy giving initiative. Discuss how you would identify target audiences, craft outreach messaging, and structure initial touchpoints to convert interest into actionable CRM data, while balancing empathetic donor engagement with rigorous documentation standards.

Format

approach-walkthrough · 20 min · ~2 hr prep

Audience

Hiring panel including Development Director, CRM Manager, and Senior Planned Giving Officer

What to prepare

  • A brief verbal outline of your campaign framework
  • Optional: 1-2 annotated examples of past outreach materials or event logistics plans (if shareable)
  • Notes on how you would handle common donor hesitations during initial conversations

Deliverables

  • A 20-minute verbal walkthrough of your campaign design and qualification process
  • Discussion of your decision-making criteria for prioritizing outreach channels and tracking metrics

Ground rules

  • Use only work you are permitted to share; anonymize donor names and sensitive financial details
  • Slides are optional; a structured verbal walkthrough is fully acceptable
  • Focus on your reasoning and process, not on creating new campaign assets or live deliverables

Scoring anchors

Exceeds
Presents a highly structured, donor-led qualification methodology that seamlessly integrates empathetic engagement, CRM data capture, and clear escalation paths; anticipates cross-functional dependencies and addresses compliance/documentation proactively.
Meets
Walks through a logical, step-by-step approach to prospect qualification with clear messaging strategies and CRM integration; acknowledges donor empathy and documentation standards, though may lack depth in handling edge cases.
Below
Offers a fragmented or purely transactional outreach plan; overlooks donor emotional cues, CRM documentation needs, or compliance boundaries; struggles to articulate a coherent qualification framework.

Response time

20 min

Positive indicators

  • Articulates a clear, donor-centric qualification framework with logical touchpoint sequencing
  • Asks high-information clarifying questions before outlining campaign tactics
  • Demonstrates how they balance empathetic pacing with CRM documentation requirements
  • Surfaces assumptions about donor readiness and explains how they would validate them
  • Provides concrete examples of how they would handle scope creep or logistical bottlenecks

Negative indicators

  • Jumps directly to tactical execution without framing donor segmentation or readiness criteria
  • Relies on generic fundraising scripts without addressing legacy-specific hesitations
  • Fails to acknowledge documentation standards or CRM data integrity
  • Dismisses potential donor emotional friction or compliance constraints
  • Overpromises on conversion timelines without acknowledging qualification variables

Work Simulation Scenario

Scenario. You are conducting a 1:1 discovery meeting with a mid-tier prospect who has expressed interest in leaving a legacy gift to support your organization's health equity programs. The prospect is emotionally invested but anxious about family dynamics and tax implications. Your goal is to uncover their core motivations, clarify their financial comfort zone, and establish a compliant next-step cultivation plan without overstepping into legal or financial advisory territory.

Problem to solve. Determine the prospect's readiness for a planned giving conversation, align their legacy motivations with appropriate standard gift vehicles, and set clear boundaries around next steps while maintaining psychological safety and trust.

Format

stakeholder-roleplay · 40 min · ~2 hr prep

Success criteria

  • Accurately identifies donor's primary legacy motivations and emotional drivers.
  • Clearly explains institutional gift options without providing legal/tax advice.
  • Establishes a mutually agreed, realistic timeline for follow-up and documentation.
  • Maintains professional boundaries when pressed for guarantees or advisory opinions.

What to review beforehand

  • Standard planned giving vehicle overview (bequests, CRAT/CRUT, CGA).
  • Institutional gift acceptance policy highlights.
  • CRM documentation standards for prospect notes and next-step tracking.

Ground rules

  • Treat the prospect as a real donor with genuine concerns and constraints.
  • Focus on relational discovery and clear communication over technical perfection.
  • If uncertain about compliance or tax implications, state the boundary and commit to consulting the appropriate internal team.

Roles in scenario

Prospective Donor (customer, played by hiring_manager)

Motivation. Wants to leave a meaningful, lasting impact on community health programs but fears family pushback and wants absolute certainty about financial security and tax outcomes.

Constraints

  • Limited immediate liquidity due to recent medical expenses.
  • Strong emotional attachment to a specific youth health initiative.
  • Expects a clear, low-pressure path forward within two weeks.

Tensions to introduce

  • Asks for guaranteed investment returns on a charitable remainder trust.
  • Pushes for informal legal advice on how to structure the estate to minimize family conflict.
  • Expresses hesitation about public recognition and legacy society naming.

In-character guidance

  • Answer honestly about family concerns, financial limits, and emotional drivers.
  • Be polite but firm about wanting reassurance before committing to paperwork.
  • Only share specific asset details or family dynamics when the candidate asks direct, respectful questions.

Do not

  • Do not solve the problem for the candidate or volunteer unasked tax/legal strategies.
  • Do not escalate hostility or become adversarial if boundaries are set.
  • Do not agree to unrealistic timelines or guaranteed financial outcomes.

Scoring anchors

Exceeds
Seamlessly balances empathetic discovery with clear compliance boundaries, leaving the donor feeling heard, informed, and confident in the next steps.
Meets
Effectively uncovers donor motivations, explains standard options clearly, and sets appropriate boundaries with a realistic follow-up plan.
Below
Over-indexes on technical details or transactional pitches, fails to set boundaries, or leaves the donor confused about next steps.

Response time

40 min

Positive indicators

  • Asks open-ended, value-driven questions to uncover legacy motivations before discussing vehicles.
  • Translates complex concepts into plain language and checks for understanding.
  • Clearly states role boundaries when asked for legal/tax advice, redirecting to qualified professionals.
  • Establishes a concrete, mutually agreed next step with realistic expectations.

Negative indicators

  • Rushes into vehicle pitches without exploring emotional or family context.
  • Provides informal legal or tax guarantees outside institutional compliance guidelines.
  • Uses vague or jargon-heavy language that increases donor anxiety.
  • Fails to set or enforce boundaries when pressed for unrealistic commitments.

Progression Framework

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

Donor Strategy & Gift Planning

4 competencies

CompetencyJuniorMidSeniorPrincipal
Donor Prospect Cultivation & Relationship Management

Supports cultivation activities by preparing communications, scheduling meetings, and maintaining contact logs to ensure seamless prospect pipeline progression.

Manages a portfolio of mid-level prospects, conducting discovery meetings and developing tailored cultivation plans.

Oversees major gift cultivation strategies, mentors staff on relationship-building, and intervenes in complex negotiations.

Sets the strategic vision for donor acquisition and retention, aligning cultivation with institutional fundraising campaigns.

Legal & Regulatory Compliance Administration

Reviews and files standard gift documents, ensuring signatures and basic compliance checkpoints are met according to organizational SOPs.

Drafts and negotiates gift agreements, verifying adherence to state/federal regulations and acceptance policies.

Resolves complex compliance issues, conducts internal audits, and updates policies to reflect regulatory changes.

Establishes organizational compliance frameworks, manages legal counsel relationships, and ensures risk mitigation.

Planned Gift Structuring & Analysis

Executes standard calculations for basic deferred gifts using established templates and tools under supervision, focusing on accuracy and flagging anomalies for senior review.

Independently structures moderately complex gifts, analyzing financial implications and drafting preliminary proposals.

Leads structuring for highly complex or multi-asset gifts, optimizing tax efficiency and coordinating with external advisors.

Defines organizational gift structuring standards, approves high-value proposals, and advises leadership on portfolio risk.

Tax & Estate Planning Advisory

Gathers donor financial data and prepares basic tax/estate summaries for review by senior staff or counsel, ensuring completeness and proper documentation.

Interprets current tax codes to advise donors on gift implications, drafting illustrative financial models.

Collaborates with donors' attorneys and CPAs to navigate complex estate plans, ensuring alignment with organizational goals.

Monitors legislative changes, develops educational resources, and shapes institutional advisory policies.

Stewardship, Systems & Strategic Leadership

4 competencies

CompetencyJuniorMidSeniorPrincipal
Donor Database & CRM Management

Enters and validates donor data, runs standard reports, and troubleshoots basic system access issues to maintain CRM data integrity.

Configures CRM workflows for gift tracking and segmentation, ensuring data integrity and user adoption.

Leads CRM system upgrades, integrates third-party tools, and establishes data governance protocols.

Aligns technology investments with strategic objectives, overseeing vendor relationships and scalable infrastructure.

Donor Stewardship & Retention Programs

Implements routine stewardship touchpoints, such as sending acknowledgments and updating donor records, to maintain consistent donor engagement.

Designs stewardship journeys for specific segments, tracking engagement metrics and adjusting outreach strategies.

Evaluates program effectiveness through retention analysis, optimizing budget allocation for high-impact initiatives.

Integrates stewardship into broader development strategy, championing donor-centric culture and retention goals.

Executive Leadership & Board Engagement

Prepares meeting materials and logistical support for board or committee presentations related to planned giving, ensuring professional coordination.

Facilitates board committee discussions, providing data-driven updates and answering operational questions.

Coaches board members on planned giving advocacy, developing training modules and fostering peer-to-peer outreach.

Partners directly with the board and C-suite to set institutional priorities, secure approvals, and drive alignment.

Strategic Program Development & Reporting

Compiles routine performance data and assists in preparing standard reports on gift pipeline progress using established templates and BI tools.

Analyzes program metrics to identify trends, drafting actionable recommendations for improving efficiency.

Develops comprehensive strategic plans, setting KPIs and presenting performance reviews to leadership.

Defines long-term program vision and growth targets, securing executive buy-in and aligning with financial sustainability.