Nonprofit FundraisingExpert-built kit

VP of Advancement / Chief Development Officer

Develops revenue strategies, cultivates principal donors, leads capital campaign planning, and optimizes annual giving workflows.

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Interview content for VP of Advancement

33
What to ask. Competency and attitude questions, assigned to the right round.
286
What to listen for. Positive and negative indicators, per question.
13
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 3 · Cross-Functional: Stakeholder Alignment & Board Relations22 competency questions

Compliance, Advocacy & Impact Ventures

Earned Revenue & Social Enterprise Models

Designs social enterprise business plans, evaluates market opportunities, and scales profitable ventures.

Expected at VP of Advancement

Sample competency question

Walk me through your evaluation process when assessing a new commercial or fee-for-service initiative to ensure it aligns with your mission and financial sustainability goals.

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

Positive indicators

  • Details how market feasibility informs initiative viability assessment
  • Explains mission alignment evaluation against strategic priorities
  • References structured financial projections and sustainability thresholds
  • Highlights pilot testing to validate assumptions before scaling
  • Demonstrates ongoing monitoring of both financial and mission outcomes

Negative indicators

  • Assesses initiatives based on financial potential without mission alignment
  • Lacks structured feasibility analysis before committing resources
  • Ignores pilot testing or validation phases before full launch
  • Overlooks ongoing performance monitoring post-implementation
  • Treats earned revenue as separate from core organizational strategy

VP evaluates feasibility and ensures mission alignment, but execution is often shared with program/finance leads; independent proficiency is sufficient.

Ryan Mahoney

Why this role is hard · Ryan Mahoney

Finding a chief development officer means looking for someone who can handle the emotional weight of fundraising while delivering steady revenue. You want a leader who truly listens to boards and donors rather than relying on rehearsed pitches. That person needs to build processes that keep staff from burning out while still meeting long-term goals. The hardest part is identifying candidates who pair solid financial planning with the patience to earn trust from other executives. Interview teams often mistake smooth public speaking for the steady discipline required to manage different funding sources.

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

Level guides for Advancement Director, VP of Advancement and Chief Development Officer.

Before you post

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

In the room

  • 22Competency interview questions
  • 11Attitude 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.

22 Competency Questions

1 of 22

  1. Discipline

    Compliance, Advocacy & Impact Ventures

  2. Job requirement

    Earned Revenue & Social Enterprise Models

    Designs social enterprise business plans, evaluates market opportunities, and scales profitable ventures.

  3. Expected at VP of Advancement

    VP evaluates feasibility and ensures mission alignment, but execution is often shared with program/finance leads; independent proficiency is sufficient.

Interview round: Cross-Functional: Stakeholder Alignment & Board Relations

Walk me through your evaluation process when assessing a new commercial or fee-for-service initiative to ensure it aligns with your mission and financial sustainability goals.

Positive indicators

  • Details how market feasibility informs initiative viability assessment
  • Explains mission alignment evaluation against strategic priorities
  • References structured financial projections and sustainability thresholds
  • Highlights pilot testing to validate assumptions before scaling
  • Demonstrates ongoing monitoring of both financial and mission outcomes

Negative indicators

  • Assesses initiatives based on financial potential without mission alignment
  • Lacks structured feasibility analysis before committing resources
  • Ignores pilot testing or validation phases before full launch
  • Overlooks ongoing performance monitoring post-implementation
  • Treats earned revenue as separate from core organizational strategy

11 Attitude Questions

1 of 11

Active Listening

Active Listening is the disciplined practice of fully concentrating on, understanding, and processing both explicit statements and implicit cues from stakeholders—donors, staff, board members, and community partners—before formulating a response. It involves suspending internal agendas, accurately interpreting underlying motivations and concerns, and deliberately reflecting insights back to validate understanding, thereby fostering psychological safety, building strategic trust, and informing data-driven advancement decisions.

Interview round: Cross-Functional: Stakeholder Alignment & Board Relations

Walk me through a time when frontline staff feedback directly contradicted your initial strategic assumptions for a campaign. How did you process and integrate their input?

Positive indicators

  • Acknowledges initial blind spots transparently
  • Details integration process step-by-step
  • Shows measurable improvement post-adjustment

Negative indicators

  • Dismisses feedback as anecdotal or unrepresentative
  • Defends original plan rigidly despite evidence
  • Isolates decision-making from execution reality

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 navigate a conversation with a high-net-worth prospect who has expressed hesitation about committing to a multi-year legacy pledge due to recent market volatility. What specific steps do you take to listen to their concerns, align their values with the organization’s mission, and guide them toward a sustainable giving decision?

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
Designs and executes multi-year integrated revenue plans across multiple streams, sets budgets, and uses analytics to align fundraising with organizational goals.
Leads CRM or platform migrations, establishes cross-departmental data workflows, and mentors directors to build management capacity.
Facilitates board campaign cabinet recruitment and training, and embeds equitable fundraising practices into outreach and stewardship frameworks.
Cultivates high-net-worth portfolios, approves major gift proposals, and enforces ethical and data privacy standards across channels.

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 integrating two to four distinct revenue streams into a cohesive donor lifecycle journey. Walk us through how you would resolve internal friction between acquisition-focused and relationship-driven teams, establish predictive pipeline models, and scale director-level talent through structured coaching and transparent accountability frameworks.

Format

strategic-brief · 60 min · ~8 hr prep

Audience

Executive leadership team and advancement directors

What to prepare

  • A 6-8 slide deck mapping your integration strategy, cross-functional protocols, and talent development framework
  • Talking points on how you would communicate trade-offs and prioritize competing departmental metrics

Deliverables

  • A narrative presentation of your strategic brief
  • A structured discussion of decision points, communication cadence, and performance alignment

Ground rules

  • You may reference past campaigns or hypothetical scenarios; do not share restricted donor data or proprietary internal documents
  • The exercise evaluates your strategic framing and cross-functional leadership, not the creation of a new operational playbook

Scoring anchors

Exceeds
Candidate demonstrates sophisticated systems thinking, seamlessly weaving data architecture, human dynamics, and executive coaching into a unified integration strategy. They proactively identify cultural friction points and design transparent accountability structures that preserve psychological safety while driving performance.
Meets
Candidate provides a coherent integration framework that addresses core cross-functional challenges and outlines reasonable talent development protocols. Their approach balances metrics with team capacity and demonstrates solid executive communication skills.
Below
Candidate defaults to top-down mandates or technology-centric fixes without addressing underlying cultural or operational silos. They struggle to articulate how competing metrics will be reconciled or how director-level coaching will be operationalized sustainably.

Response time

60 min

Positive indicators

  • Maps clear handoff protocols and decision rights across historically siloed teams
  • Balances data-driven forecasting with human-centric relationship management
  • Surfaces potential friction points and proposes transparent resolution mechanisms
  • Aligns predictive metrics with realistic staff capacity and psychological safety guardrails

Negative indicators

  • Assumes alignment without addressing competing KPIs or departmental cultural differences
  • Prioritizes technology or metrics over staff capacity and team cohesion
  • Fails to articulate how cross-functional protocols will be sustained post-launch
  • Overlooks the need for active listening when reconciling conflicting departmental priorities

Work Simulation Scenario

Scenario. The Board Development Committee Chair has scheduled a closed-door session to review the upcoming capital campaign’s resource allocation and cabinet structure. They are pushing for direct oversight of the digital marketing team and want to bypass standard prospect vetting to accelerate near-term yield.

Problem to solve. Negotiate governance boundaries, align the committee on a unified campaign strategy that balances short-term targets with long-term pipeline health, and clarify role delineation between board advisory functions and staff execution.

Format

negotiation · 75 min · ~5 hr prep

Success criteria

  • Establish clear governance boundaries protecting staff workflows
  • Align committee on predictive pipeline metrics over aggressive short-term asks
  • Demonstrate active listening and transparent prioritization
  • Secure board commitment to a structured, ethically paced campaign framework

What to review beforehand

  • Board governance charters and committee advisory scope definitions
  • Current campaign pacing models and donor retention forecasts
  • Cross-functional team capacity and digital marketing integration protocols
  • Historical board-advancement friction points and resolution frameworks

Ground rules

  • This is a negotiation on governance, scope, and resource allocation
  • Drive the conversation toward structural alignment and mutual accountability
  • You may propose trade-offs but must defend sustainable pacing and staff capacity
  • Do not draft policy documents; focus on verbal agreements and escalation paths

Roles in scenario

Board Development Committee Chair (skeptical_stakeholder, played by leadership)

Motivation. Maximize near-term campaign yield to demonstrate quick wins to the full board, while maintaining personal influence over advancement operations.

Constraints

  • Full board expects visible fundraising progress within 90 days
  • Reluctant to cede operational control to staff without oversight mechanisms
  • Concerned about digital team’s ROI and donor acquisition costs

Tensions to introduce

  • Request direct approval authority over prospect outreach sequencing
  • Push to bypass standard vetting for warm donor leads
  • Question staff capacity and demand weekly tactical check-ins

In-character guidance

  • Frame requests around board accountability and fiduciary oversight
  • Listen to structural arguments but test them with practical pushback
  • Reveal constraints only when directly asked about board expectations
  • Maintain a collaborative but firm stance on timeline and visibility

Do not

  • Do not hand over a pre-written governance solution
  • Do not escalate to hostility if boundaries are set clearly
  • Do not volunteer internal board dynamics unless explicitly asked

Scoring anchors

Exceeds
Successfully negotiates clear governance boundaries, aligns board on sustainable pacing, and establishes transparent accountability frameworks while demonstrating exceptional active listening and strategic communication.
Meets
Reaches a functional agreement on cabinet roles and campaign pacing, establishes basic boundaries, and maintains collaborative board relations, though some operational details remain ambiguous.
Below
Concedes to board overreach, fails to clarify decision rights, or relies on defensive communication that fractures trust and leaves governance boundaries undefined.

Response time

75 min

Positive indicators

  • Explicitly maps advisory scope versus staff execution responsibilities using precise, jargon-free language
  • Surfaces board expectations through targeted questioning before committing to timelines
  • Proposes transparent prioritization matrices that balance short-term visibility with long-term pipeline health
  • Demonstrates intellectual humility by acknowledging valid board concerns while defending data-driven pacing

Negative indicators

  • Allows scope creep into tactical staff workflows without firm pushback
  • Uses ambiguous language around decision rights and escalation paths
  • Interrupts or dismisses board concerns about near-term yield
  • Fails to translate governance frameworks into actionable, mutually agreed boundaries

Progression Framework

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

Compliance, Advocacy & Impact Ventures

4 competencies

CompetencyAdvancement DirectorVP of AdvancementChief Development Officer
Earned Revenue & Social Enterprise Models

Manages day-to-day earned revenue operations, tracks sales metrics, and ensures product alignment with mission.

Designs social enterprise business plans, evaluates market opportunities, and scales profitable ventures.

Integrates earned revenue into long-term financial strategy, secures impact investment partnerships, and drives organizational diversification.

Inclusive & Equitable Fundraising Practices

Implements inclusive messaging guidelines, tracks demographic engagement metrics, and supports diverse donor outreach.

Audits fundraising practices for bias, redesigns stewardship to reflect diverse communities, and leads EDI training for advancement staff.

Institutionizes equity as a core fundraising pillar, partners with marginalized communities in strategy design, and ensures resource distribution reflects inclusive values.

Policy Mobilization & Advocacy

Coordinates grassroots outreach, tracks legislative calendars, and manages advocacy communication blasts.

Designs advocacy campaigns, builds coalitions with policy partners, and aligns donor engagement with public policy priorities.

Champions sector-wide policy reform, secures advocacy-aligned funding, and positions the organization as a thought leader in public policy.

Regulatory Affairs & Risk Mitigation

Maintains compliance checklists, files required disclosures, and monitors regulatory updates.

Develops risk assessment frameworks, audits fundraising practices, and implements corrective action plans.

Sets institutional compliance posture, liaises with legal counsel on complex regulatory matters, and embeds risk management into enterprise strategy.

Data Infrastructure & Donor Experience

5 competencies

CompetencyAdvancement DirectorVP of AdvancementChief Development Officer
CRM Architecture & Data Management

Manages daily CRM updates, troubleshoots data entry issues, and generates standard operational reports.

Architects CRM segmentation strategies, integrates third-party tools, and enforces data governance policies.

Directs enterprise data strategy, evaluates next-generation CRM platforms, and ensures data infrastructure scales with organizational growth.

Cross-Functional Integration

Coordinates interdepartmental meetings, shares data reports, and manages shared project timelines.

Establishes cross-functional SLAs, breaks down operational silos, and implements unified reporting dashboards.

Champions enterprise integration, aligns advancement KPIs with organizational OKRs, and drives systemic process harmonization.

Donor Journey Optimization

Tracks journey metrics, executes targeted communications, and resolves donor service issues.

Redesigns omnichannel engagement pathways, tests conversion funnels, and aligns marketing with development workflows.

Sets donor experience vision, integrates CX frameworks across all advancement functions, and benchmarks against sector best practices.

Organizational Leadership & Workflow Design

Supervises staff workflows, delegates tasks, and implements standard operating procedures.

Designs team structures, optimizes resource allocation, and leads process improvement initiatives.

Defines organizational development strategy, cultivates leadership pipelines, and transforms operational culture to support scalable growth.

Predictive Analytics & Donor Insights

Runs standard propensity reports, segments lists for campaigns, and monitors basic engagement metrics.

Develops predictive scoring models, correlates donor behavior with campaign outcomes, and advises strategy based on insights.

Institutionalizes data science practices, funds advanced analytics initiatives, and aligns predictive modeling with enterprise fundraising targets.

Strategic Fundraising & Governance

4 competencies

CompetencyAdvancement DirectorVP of AdvancementChief Development Officer
Board Governance & Engagement

Prepares board packets, coordinates committee meetings, and tracks board giving metrics.

Designs board engagement frameworks, aligns governance structures with development goals, and mentors board chairs.

Leads board succession planning, integrates governance with enterprise strategy, and ensures fiduciary and fundraising accountability at the executive level.

Institutional Grant Relations

Drafts grant narratives, assembles proposal packages, and monitors submission deadlines.

Aligns grant strategy with programmatic goals, negotiates multi-year institutional agreements, and builds funder networks.

Shapes macro-grant strategy, cultivates executive-level institutional partnerships, and ensures funding portfolios support transformative initiatives.

Major Donor Cultivation & Stewardship

Conducts donor meetings, tracks solicitation pipelines, and executes stewardship touchpoints.

Oversees major gift portfolios, designs tiered stewardship frameworks, and coaches staff on high-value negotiation.

Cultivates C-suite and foundation-level partnerships, establishes legacy giving programs, and represents the organization at elite philanthropic forums.

Revenue Planning & Capital Campaign Strategy

Executes annual fundraising plans, tracks campaign milestones, and manages day-to-day revenue reporting.

Designs multi-year campaign architectures, optimizes portfolio allocation, and leads cross-departmental alignment on revenue targets.

Architects enterprise-wide capital campaigns, secures anchor gifts, and sets institutional fundraising vision aligned with long-term mission sustainability.