Interview Guide for

Proposal Writer and Strategist

This comprehensive interview guide is designed to help you evaluate candidates for the Proposal Writer and Strategist role. By following a structured approach to interviews with consistent questions and evaluation criteria, you'll be able to objectively assess each candidate's writing abilities, strategic thinking, project management skills, and collaborative approach, which are essential for success in this position.

How to Use This Guide

This interview guide provides a framework for conducting thorough, consistent, and effective interviews for your Proposal Writer and Strategist candidates. To make the most of it:

Customize to Your Context - Adapt questions and evaluation criteria to align with your [company]'s specific proposal process, industry, and culture.
Share with Your Team - Ensure everyone involved in the hiring process understands the interview structure, essential competencies, and how to use the scorecard system.
Maintain Consistency - Ask the same core questions to all candidates to enable fair comparisons.
Dive Deeper - Use follow-up questions to explore candidates' experiences fully and gather the context needed for objective assessment.
Score Independently - Have each interviewer complete their scorecard before discussing candidates to prevent groupthink.

For additional guidance on conducting effective interviews, check out our resources on how to conduct a job interview and why you should use structured interviews.

Job Description

Proposal Writer and Strategist

About [Company]

[Company] is an innovative leader in the [industry] space, dedicated to delivering exceptional solutions to our clients. Our collaborative culture values creativity, strategic thinking, and a commitment to excellence. Join our growing team and contribute to our continued success in a supportive and dynamic environment.

The Role

As a Proposal Writer and Strategist at [Company], you will play a crucial role in our business development efforts by crafting compelling, persuasive proposals that showcase our capabilities and win new business. Your strategic approach to proposal development and exceptional writing skills will directly contribute to our company's growth and success in competitive situations.

Key Responsibilities

Lead the end-to-end proposal process, from initial review of RFPs/RFIs to final submission
Analyze client requirements and develop comprehensive proposal outlines and storyboards
Write clear, concise, and persuasive content that effectively communicates our value proposition
Develop and implement proposal strategies to enhance competitiveness and win rates
Research competitors and market trends to inform strategic approaches
Manage multiple proposal projects simultaneously while meeting strict deadlines
Collaborate with subject matter experts, sales teams, and management to gather information
Ensure proposals adhere to all requirements and maintain quality standards

What We're Looking For

Exceptional writing, editing, and proofreading abilities with attention to detail
Strategic mindset with ability to analyze requirements and develop winning approaches
Strong project management skills and experience juggling multiple deadlines
Research skills and ability to quickly understand technical concepts
Collaborative approach with excellent interpersonal and communication skills
Demonstrated ability to work under pressure while maintaining quality
Experience with proposal development and knowledge of best practices
Bachelor's degree in relevant field (English, Communications, Marketing, etc.)
Understanding of [industry] concepts and trends (preferred)

Why Join [Company]

At [Company], we value innovation, collaboration, and excellence. We offer:

Opportunity to work on exciting projects that drive business growth
Collaborative team environment with supportive leadership
Professional development and growth opportunities
Competitive compensation package including:
Salary range: [Pay Range]
Comprehensive health benefits
Retirement plan with company match
Flexible work arrangements
Paid time off and holidays

Hiring Process

We've designed our hiring process to be thorough yet efficient, providing you opportunities to showcase your skills while getting to know our team and culture.

Initial Screening - A conversation with our recruiter to discuss your background and interest in the role
Proposal Writing Exercise - A writing sample that demonstrates your ability to craft persuasive proposal content
Career Experience Interview - An in-depth discussion about your relevant work history and achievements
Strategic Thinking & Collaboration Interview - Exploration of your strategic approach and collaborative style

Throughout the process, we encourage questions and aim to give you a clear picture of what working at [Company] is like. We respect your time and will communicate promptly at each stage.

Ideal Candidate Profile (Internal)

Role Overview

The Proposal Writer and Strategist serves as a critical link between our business development/sales efforts and winning new business. This role requires a unique blend of creative writing talent, strategic thinking, and project management capabilities. The ideal candidate will have the ability to understand complex technical concepts quickly, translate them into compelling value propositions, and manage multiple proposal projects simultaneously under tight deadlines. Success in this role requires excellent interpersonal skills to collaborate effectively with subject matter experts, sales teams, and management.

Essential Behavioral Competencies

Strategic Thinking - Demonstrates the ability to analyze client requirements, identify key decision factors, and develop approaches that position the company competitively; can anticipate potential objections and address them proactively in proposal content.

Project Management - Successfully manages multiple complex projects simultaneously; establishes priorities, delegates tasks appropriately, maintains organization, and consistently meets deadlines in a fast-paced environment.

Written Communication - Produces clear, concise, persuasive, and error-free content that effectively communicates complex ideas; tailors writing style and content to specific audiences and requirements.

Research & Analysis - Quickly gathers, synthesizes, and applies relevant information; demonstrates keen attention to detail when reviewing RFPs/RFIs to ensure all requirements are addressed.

Collaboration - Works effectively with diverse stakeholders; builds relationships across departments; successfully elicits information from subject matter experts and incorporates feedback constructively.

Desired Outcomes

Increase proposal win rate by 15% through implementation of improved proposal strategies and more compelling content within the first year.
Develop a comprehensive proposal content library organized by solution/service area, reducing proposal development time by 20% within six months.
Implement a streamlined proposal process that improves cross-functional collaboration and reduces internal review cycles by 25%.
Create proposal templates and style guides that ensure consistent branding and messaging across all company proposals.
Contribute to business growth by helping to secure at least [specific value or number] in new business through successful proposals annually.

Ideal Candidate Traits

Exceptional writing skills with a portfolio demonstrating persuasive content creation
3-5 years of experience in proposal writing, preferably in [industry] or related field
Proven track record of developing winning proposals with specific examples of success
Experience collaborating with subject matter experts to translate technical concepts into compelling benefits
Demonstrated ability to manage multiple proposal projects simultaneously under tight deadlines
Strong strategic thinking capacity with examples of developing differentiated positioning
Self-motivated with ability to work independently and as part of a team
Excellent organizational skills with attention to detail
Adaptable and flexible approach to changing priorities
Proficiency with Microsoft Office Suite and proposal management/CRM software
Bachelor's degree in English, Communications, Marketing, Journalism, or relevant field

Screening Interview

Directions for the Interviewer

This initial screening interview aims to quickly identify candidates who possess the essential qualifications and characteristics needed for the Proposal Writer and Strategist role. Focus on evaluating their writing experience, strategic approach to proposals, project management capabilities, and collaborative style.

The questions are designed to assess both technical skills and behavioral traits that indicate potential for success in this role. Pay particular attention to:

The quality and clarity of their verbal communication
Their understanding of proposal development processes
Evidence of strategic thinking in their approach to proposals
Their ability to manage multiple deadlines and projects
Examples of successful collaborations with subject matter experts

Listen for concrete examples rather than theoretical answers. Take note of candidates who can articulate specific instances where they've crafted winning proposals, implemented effective strategies, or successfully managed complex proposal processes. Be sure to leave time at the end for candidate questions.

Directions to Share with Candidate

"Today we'll be discussing your experience with proposal writing and development, along with your approach to strategic thinking and project management. I'm interested in hearing specific examples from your background that demonstrate your skills in these areas. This conversation will help us understand how your experience aligns with our needs for the Proposal Writer and Strategist role. Please feel free to ask questions throughout our discussion."

Interview Questions

Tell me about your experience with proposal writing and development. What types of proposals have you worked on, and what was your specific role in the process?

Areas to Cover

Range of proposal types (RFPs, RFIs, unsolicited proposals, etc.)
Industries or sectors they've written for
Level of responsibility (contributor vs. lead)
Size and complexity of proposals managed
Process followed from RFP receipt to submission

Possible Follow-up Questions

What was the largest or most complex proposal you've led from start to finish?
How did you approach the different sections of proposals (executive summary, technical, pricing)?
What tools or software have you used to manage the proposal process?

Describe a situation where you had to develop a strategic approach to win a competitive proposal. What was your process, and what was the outcome?

Areas to Cover

How they gathered competitive intelligence
Their approach to identifying client hot buttons or key decision factors
Specific strategies they implemented to differentiate from competitors
Methods used to highlight value proposition and benefits
Results achieved (win/loss and lessons learned)

Possible Follow-up Questions

How did you identify the client's unstated needs or concerns?
What research did you conduct to inform your strategic approach?
How did you measure the effectiveness of your strategy?

How do you manage multiple proposal projects with competing deadlines? Please share a specific example.

Areas to Cover

Prioritization methods and tools
Time management strategies
Delegation and team coordination approach
How they handle unexpected changes or challenges
Stress management techniques during peak periods

Possible Follow-up Questions

What happens when priorities suddenly shift?
How do you communicate timeline challenges to stakeholders?
What tools do you use to stay organized when managing multiple proposals?

Tell me about your experience collaborating with subject matter experts to gather technical information. How do you approach these interactions?

Areas to Cover

Methods for engaging busy technical experts
Techniques for eliciting complex information
How they translate technical details into client-focused benefits
Handling resistance or limited availability of experts
Following up and validating information accuracy

Possible Follow-up Questions

How do you prepare for meetings with subject matter experts?
What do you do when you receive conflicting information from different experts?
How do you handle situations where experts use highly technical language that needs simplification?

Can you walk me through your process for analyzing an RFP and developing a compelling response?

Areas to Cover

Initial RFP review approach
Methods for identifying and extracting requirements
Compliance checking procedures
Content organization and storyboarding techniques
Quality assurance and review process

Possible Follow-up Questions

How do you ensure you've addressed all requirements in an RFP?
What do you look for to identify the unstated needs behind the written requirements?
How do you determine which win themes to emphasize in your response?

What methods do you use to measure the effectiveness of your proposals? How do you incorporate feedback into future efforts?

Areas to Cover

Win/loss analysis approach
Client feedback collection methods
Internal review process
Continuous improvement techniques
Knowledge management and lessons learned

Possible Follow-up Questions

How do you conduct a win/loss analysis?
What's the most significant improvement you've implemented based on feedback?
How do you maintain a proposal content library or knowledge base?

Interview Scorecard

Writing Experience and Skill

0: Not Enough Information Gathered to Evaluate
1: Limited proposal writing experience or lacks depth in creating persuasive content
2: Some proposal writing experience but may lack sophisticated techniques or strategy
3: Solid proposal writing experience with demonstrated ability to create persuasive content
4: Extensive proposal writing experience with proven track record of creating winning proposals

Strategic Thinking

0: Not Enough Information Gathered to Evaluate
1: Approaches proposals tactically rather than strategically
2: Shows some strategic thinking but may miss competitive differentiation opportunities
3: Demonstrates clear strategic thinking in proposal development
4: Exceptional strategic approach with innovative methods for competitive positioning

Project Management Capability

0: Not Enough Information Gathered to Evaluate
1: Struggles with managing multiple projects or meeting deadlines
2: Can manage straightforward projects but may be challenged by complexity
3: Effectively manages multiple complex proposals and deadlines
4: Exceptional project management skills with innovative approaches to efficiency

Collaboration and Stakeholder Management

0: Not Enough Information Gathered to Evaluate
1: Limited experience working with cross-functional teams or subject matter experts
2: Can collaborate but may struggle with difficult stakeholders or complex situations
3: Demonstrates effective collaboration skills and stakeholder management
4: Exceptional collaboration skills with proven ability to influence and engage diverse stakeholders

Goal: Increase proposal win rate

0: Not Enough Information Gathered to Evaluate
1: Unlikely to improve proposal win rates significantly
2: May contribute moderately to improved win rates
3: Likely to achieve the target 15% increase in win rates
4: Likely to exceed the target and substantially improve win rates

Goal: Develop comprehensive proposal content library

0: Not Enough Information Gathered to Evaluate
1: Unlikely to effectively develop and organize a content library
2: May create basic content resources but not a comprehensive system
3: Likely to achieve the goal of developing an effective content library
4: Likely to exceed expectations by creating an innovative and highly efficient content library system

Goal: Implement streamlined proposal process

0: Not Enough Information Gathered to Evaluate
1: Unlikely to improve current processes significantly
2: May make incremental improvements but not achieve 25% reduction target
3: Likely to achieve the target process improvements
4: Likely to exceed target with innovative process improvements

Recommendation to Proceed

1: Strong No Hire
2: No Hire
3: Hire
4: Strong Hire

Proposal Writing Work Sample

Directions for the Interviewer

This work sample is designed to assess the candidate's ability to create compelling proposal content under realistic conditions. The exercise evaluates their writing skill, strategic thinking, and ability to respond to client requirements – all critical competencies for success in this role.

Before the interview, select an appropriate RFP section or executive summary scenario based on your company's typical proposals. Keep the scope manageable (1-2 pages of writing) but challenging enough to demonstrate their capabilities. Provide the candidate with:

A brief background on a fictional client and their needs
Key requirements/questions to address in their response
Basic information about your [company]'s relevant capabilities
Clear formatting and submission guidelines

Allow candidates the option to complete this exercise in advance (24-48 hours) or during a timed session (90-120 minutes). If completed in advance, schedule a follow-up discussion where they can walk you through their approach and thinking.

During the review, evaluate not just the final product but also their process and strategic thinking. Note how they:

Identified and emphasized key selling points
Addressed client requirements and pain points
Organized information logically and persuasively
Differentiated your company from hypothetical competitors
Demonstrated attention to detail and writing mechanics

Remember to save time for candidate questions at the end of the interview. This exercise should feel challenging but fair, and representative of the actual work they would do in the role.

Directions to Share with Candidate

"This exercise is designed to assess your proposal writing skills in a realistic scenario. You'll be creating a response to a section of an RFP (or an executive summary) for a fictional client. We're looking at your ability to:

Understand and address client requirements
Craft compelling, persuasive content
Communicate complex information clearly
Think strategically about positioning
Organize information effectively

You'll have access to basic information about our company's capabilities relevant to this proposal. While this is a simplified version of a real proposal, we encourage you to approach it with the same strategic thinking and attention to detail you would use in an actual proposal response. After completing the writing sample, we'll discuss your approach and thinking process."

Work Sample Exercise

Executive Summary Challenge

Background: [Fictional Client] is seeking a [service/product] to address [specific business challenge]. They have issued an RFP to several vendors, including [Company]. You have been asked to draft the Executive Summary (1-2 pages) for [Company]'s proposal response.

Client Profile:

Industry: [Relevant to your company]
Size: [Medium to large organization]
Key challenge: [Specific problem they're trying to solve]
Additional context: [Budget constraints, timeline pressures, past vendor disappointments, etc.]

Requirements for your Executive Summary:

Demonstrate understanding of the client's needs and challenges
Highlight [Company]'s unique qualifications and approach
Present a compelling value proposition
Address any potential client concerns
Include a clear statement of benefits/outcomes
Maintain professional tone and error-free writing

Resources provided:

Company capabilities overview
Service/product information sheet
Basic pricing structure (if relevant)

Evaluation criteria:

Strategic positioning and messaging
Persuasiveness and client focus
Content organization and flow
Writing quality and clarity
Alignment with requirements

After completion, be prepared to discuss:

Your approach to analyzing the client's needs
How you developed your key messages and themes
Any strategic decisions made in your writing
How you would adapt this for different types of clients

Interview Scorecard

Strategic Approach

0: Not Enough Information Gathered to Evaluate
1: Lacks strategic thinking; generic approach without client-specific focus
2: Shows basic strategic elements but misses key opportunities for differentiation
3: Demonstrates effective strategic thinking aligned with client needs
4: Exceptional strategic approach with innovative positioning and compelling win themes

Writing Quality and Persuasiveness

0: Not Enough Information Gathered to Evaluate
1: Writing is unclear, contains errors, or fails to persuade
2: Writing is adequate but lacks impact or professional polish
3: Well-written, persuasive content with clear messaging
4: Exceptional writing that compels action with powerful, concise language

Client Focus

0: Not Enough Information Gathered to Evaluate
1: Primarily company-focused rather than addressing client needs
2: Acknowledges client needs but doesn't fully address their specific challenges
3: Effectively addresses client needs and demonstrates understanding of their situation
4: Exceptional client focus with insights that go beyond stated requirements

Content Organization and Structure

0: Not Enough Information Gathered to Evaluate
1: Poorly organized with illogical flow or difficult-to-follow structure
2: Basic organization but could improve flow or emphasis
3: Well-organized with logical flow and appropriate emphasis on key points
4: Exceptional organization that guides reader through a compelling narrative

Goal: Increase proposal win rate

0: Not Enough Information Gathered to Evaluate
1: Writing quality unlikely to improve win rates
2: Content may improve win rates slightly but not reach 15% target
3: Quality likely to contribute to meeting the 15% win rate improvement goal
4: Quality likely to exceed target with highly compelling content

Goal: Develop comprehensive proposal content library

0: Not Enough Information Gathered to Evaluate
1: Work sample shows limited reusable content potential
2: Contains some reusable elements but limited versatility
3: Shows good potential for creating versatile, reusable content
4: Demonstrates exceptional ability to create content with high reuse value

Goal: Implement streamlined proposal process

0: Not Enough Information Gathered to Evaluate
1: Approach to work sample suggests inefficient processes
2: Shows some efficiency but may not achieve process improvement targets
3: Approach suggests ability to implement effective process improvements
4: Demonstrates innovative approach that would likely exceed process improvement targets

Recommendation to Proceed

1: Strong No Hire
2: No Hire
3: Hire
4: Strong Hire

Chronological Interview

Directions for the Interviewer

This interview takes a structured walk through the candidate's career history, focusing on their proposal writing and strategy development experience. The goal is to understand the depth and progression of their skills, their performance in previous roles, and how their experience has prepared them for this position.

Ask the candidate to discuss each relevant position in chronological order, starting with the most recent. For each role, use the core questions below, adapting them as needed based on the specifics of each position. This approach will help you:

Understand the context and scale of their proposal work in each role
Evaluate their growth in strategic thinking and writing capabilities
Identify patterns in their performance and problem-solving approaches
Gain insight into their collaborative style and stakeholder management
Assess their project management skills across different environments

Focus more deeply on recent and highly relevant roles. Probe for specific metrics and outcomes, not just responsibilities. Listen for concrete examples of successful proposals, strategies implemented, and lessons learned. Note any gaps in experience or inconsistencies in their narrative.

Remember to save time for candidate questions at the end of the interview.

Directions to Share with Candidate

"In this interview, we'll take a chronological approach to understanding your career experience, focusing specifically on your proposal writing and strategy work. I'd like to walk through your relevant positions, starting with your most recent role, discussing your responsibilities, accomplishments, and growth in each. I'm particularly interested in understanding the types of proposals you've worked on, your strategic approach, and the outcomes you've achieved. Please be specific about your contributions and the impact of your work in each role."

Interview Questions

Before we dive into specific roles, what would you say has been your most significant career achievement related to proposal writing or strategy?

Areas to Cover

The context of the achievement
Their specific contribution and role
Metrics or evidence of success
Skills or approaches that made it successful
What they learned from the experience

Possible Follow-up Questions

What made this achievement particularly meaningful to you?
How did this success influence your subsequent approach to proposals?
What would you do differently if you could approach this situation again?

Starting with your current/most recent position at [Company Name], tell me about your role and responsibilities related to proposal writing and strategy.

Areas to Cover

Types and volume of proposals managed
Size of proposals (dollar value, page count)
Win rates and performance metrics
Team structure and their position within it
Growth or changes in their responsibilities over time

Possible Follow-up Questions

What was the most challenging proposal you worked on in this role?
How did your approach to proposals evolve during your time in this position?
What systems or processes did you implement or improve?

What was your process for developing proposal strategies in this role? Can you walk me through a specific example?

Areas to Cover

Their strategic thinking process
How they gathered competitive intelligence
Methods for identifying client hot buttons
Approach to differentiating their company's offering
How they validated their strategic approach

Possible Follow-up Questions

How did you handle situations where you had limited information about the client?
What research or resources did you typically use to inform your strategy?
How did you adapt your approach for different types of clients or industries?

Tell me about the most significant proposal challenge you faced in this role and how you overcame it.

Areas to Cover

Nature of the challenge (tight deadline, limited resources, complex requirements)
Their problem-solving approach
Resources or support they leveraged
Results achieved despite the challenge
Lessons learned and applied to future situations

Possible Follow-up Questions

How did you maintain quality while dealing with this challenge?
What would you do differently if faced with a similar situation?
How did you communicate the challenge to stakeholders?

How did you collaborate with subject matter experts and other stakeholders in this role?

Areas to Cover

Their approach to engaging technical experts
Methods for eliciting information
Handling resistance or limited availability
Communication style and adaptability
Conflict resolution techniques

Possible Follow-up Questions

How did you handle situations where experts provided overly technical information?
What techniques did you use to get input from reluctant or busy stakeholders?
How did you manage conflicting opinions or information?

Moving to your previous role at [Company Name], how did your proposal responsibilities differ from your current/most recent position?

Areas to Cover

Evolution in their level of responsibility
Differences in proposal types or complexity
Changes in their strategic approach
Growth in skills or capabilities
Different challenges faced and how they adapted

Possible Follow-up Questions

What new skills did you develop in this transition?
How did your previous experience prepare you for the increased responsibility?
What aspects of proposal development became easier or more challenging?

Looking across your career, how has your approach to proposal writing and strategy evolved over time?

Areas to Cover

Key lessons learned
Changes in their strategic thinking
Evolution of their writing style
Adoption of new methodologies or tools
Development of their professional judgment

Possible Follow-up Questions

What has been the most valuable lesson you've learned about proposal development?
How have industry or market changes affected your approach?
What skills do you still want to develop further?

Interview Scorecard

Career Progression and Skill Development

0: Not Enough Information Gathered to Evaluate
1: Limited growth in responsibilities or capabilities over time
2: Some progression but may lack depth in key areas
3: Clear progression with increasing responsibility and skill development
4: Exceptional career trajectory showing consistent growth and mastery

Strategic Thinking Evolution

0: Not Enough Information Gathered to Evaluate
1: Limited evidence of strategic thinking development
2: Some strategic capabilities but inconsistent application
3: Strong development of strategic thinking demonstrated through career
4: Exceptional strategic capabilities with evidence of innovative approaches

Writing and Communication Skills

0: Not Enough Information Gathered to Evaluate
1: Basic writing skills with limited evidence of improvement
2: Adequate writing skills but may lack sophistication or impact
3: Strong writing skills with clear development over career
4: Exceptional writing talent with evidence of mastery and versatility

Project Management Capability

0: Not Enough Information Gathered to Evaluate
1: Handles basic project management but struggles with complexity
2: Manages standard projects but may be challenged by tight deadlines or multiple priorities
3: Effectively manages complex proposal projects and competing deadlines
4: Exceptional project management with evidence of innovative approaches to efficiency

Goal: Increase proposal win rate

0: Not Enough Information Gathered to Evaluate
1: Limited track record of improving win rates
2: Some success increasing win rates but below target levels
3: Demonstrated ability to achieve target win rate improvements
4: Exceptional history of exceeding win rate targets

Goal: Develop comprehensive proposal content library

0: Not Enough Information Gathered to Evaluate
1: Limited experience with content management or knowledge systems
2: Some content development experience but lacks systematic approach
3: Demonstrated ability to develop effective content libraries
4: Exceptional content management experience with innovative approaches

Goal: Implement streamlined proposal process

0: Not Enough Information Gathered to Evaluate
1: Limited process improvement experience
2: Some process optimization but may not achieve target efficiencies
3: Proven ability to implement effective process improvements
4: Exceptional track record of process transformation and efficiency gains

Recommendation to Proceed

1: Strong No Hire
2: No Hire
3: Hire
4: Strong Hire

Strategic Thinking & Collaboration Interview

Directions for the Interviewer

This interview focuses on assessing the candidate's strategic thinking abilities and collaborative approach – two critical success factors for the Proposal Writer and Strategist role. The questions are designed to evaluate how the candidate analyzes complex situations, develops winning strategies, and works effectively with diverse stakeholders.

Pay particular attention to:

How they analyze client needs and competitive landscapes
Their ability to develop differentiated positioning
Their approach to solving strategic challenges
How they handle collaborative difficulties
Their methods for influencing others and building consensus

Look for specific examples rather than theoretical approaches. Strong candidates will provide concrete instances where they've implemented successful strategies or navigated challenging collaborations. Note their ability to explain complex concepts clearly and adapt their communication style.

This interview should give you insight into how the candidate would approach strategic proposal development at your organization and how effectively they would work with subject matter experts, sales teams, and management. Remember to save time for candidate questions at the end of the interview.

Directions to Share with Candidate

"In this interview, we'll focus on your strategic thinking abilities and collaborative approach, both essential for success in the Proposal Writer and Strategist role. I'm interested in hearing specific examples of how you've developed proposal strategies and worked with diverse stakeholders to create winning proposals. Please provide concrete examples where possible, sharing both successes and challenges you've encountered. This will help us understand how you might approach similar situations at [Company]."

Interview Questions

Describe a situation where you had to develop a proposal strategy for a highly competitive opportunity. What was your approach, and what was the outcome?

Areas to Cover

How they assessed the competitive landscape
Their process for identifying client priorities and hot buttons
Specific differentiation strategies they developed
How they incorporated these strategies into the proposal
Results achieved and lessons learned

Possible Follow-up Questions

What information sources did you use to develop your competitive analysis?
How did you determine which differentiators would resonate most with the client?
What would you do differently if faced with a similar situation now?

Tell me about a time when you had to translate complex technical information into compelling proposal content. How did you approach this challenge?

Areas to Cover

Their process for understanding technical concepts
Methods used to extract key information from subject matter experts
Techniques for simplifying without losing accuracy
How they transformed features into benefits
Examples of successful outcomes

Possible Follow-up Questions

How do you ensure accuracy when writing about technical concepts outside your expertise?
What techniques do you use to make technical content engaging?
How do you handle situations where technical experts disagree?

Describe a challenging collaborative situation you faced while developing a proposal. How did you handle it, and what was the result?

Areas to Cover

Nature of the collaborative challenge
Their approach to understanding different perspectives
Conflict resolution techniques employed
How they built consensus or found compromise
Results achieved and impact on the proposal

Possible Follow-up Questions

How did you adjust your communication style for different stakeholders?
What would you do differently if you encountered a similar situation?
How did this experience influence your approach to future collaborations?

Tell me about a time when you had to influence decision-makers to adopt your recommended proposal strategy. What was your approach?

Areas to Cover

Context of the situation and their recommendation
Analysis they conducted to support their position
How they presented their case to leadership
Techniques used to influence and persuade
Outcome and impact on the proposal

Possible Follow-up Questions

How did you handle resistance or skepticism?
What evidence or data did you use to support your position?
How do you adapt your approach when influencing different types of stakeholders?

Describe how you would analyze an RFP to identify unstated client needs or concerns. Can you share a specific example where you uncovered hidden requirements?

Areas to Cover

Their RFP analysis methodology
Techniques for reading between the lines
Research conducted beyond the RFP document
How they validated assumptions about unstated needs
How these insights were incorporated into the proposal

Possible Follow-up Questions

What resources do you typically use to research client needs beyond the RFP?
How do you differentiate between a genuine unstated need and an assumption?
How do you address unstated needs in a proposal without seeming presumptuous?

Tell me about a time when you had to rapidly develop a proposal strategy with limited information or under tight time constraints. How did you approach this challenge?

Areas to Cover

Their prioritization process
Information gathering techniques under pressure
Decision-making approach with incomplete data
Risk management strategies
Results achieved despite constraints

Possible Follow-up Questions

How do you balance thoroughness with time constraints?
What shortcuts, if any, did you take, and how did you mitigate potential risks?
How do you maintain strategic thinking when under pressure?

Interview Scorecard

Strategic Analysis

0: Not Enough Information Gathered to Evaluate
1: Limited analytical ability; superficial understanding of competitive factors
2: Basic analysis of competitive situations but may miss nuanced opportunities
3: Strong analytical skills with ability to identify key competitive factors
4: Exceptional strategic analysis with innovative approaches to competitive positioning

Client-Focused Thinking

0: Not Enough Information Gathered to Evaluate
1: Limited focus on client needs; primarily company-centric thinking
2: Recognizes client needs but may not fully integrate into strategies
3: Consistently considers client perspective in strategic development
4: Exceptional client focus with ability to uncover and address unstated needs

Collaborative Approach

0: Not Enough Information Gathered to Evaluate
1: Struggles with challenging collaborative situations
2: Manages basic collaboration but may have difficulty with complex stakeholder dynamics
3: Effectively navigates collaborative challenges with diverse stakeholders
4: Exceptional collaboration skills with ability to build consensus in difficult situations

Influence and Persuasion

0: Not Enough Information Gathered to Evaluate
1: Limited ability to influence others or gain buy-in
2: Some persuasive capabilities but may struggle with resistant stakeholders
3: Effectively influences others and builds support for ideas
4: Exceptional persuasive abilities with sophisticated stakeholder management

Goal: Increase proposal win rate

0: Not Enough Information Gathered to Evaluate
1: Strategic approach unlikely to improve win rates significantly
2: May contribute to modest win rate improvements
3: Strategic abilities likely to achieve target win rate improvements
4: Exceptional strategic approach likely to exceed win rate targets

Goal: Develop comprehensive proposal content library

0: Not Enough Information Gathered to Evaluate
1: Limited strategic vision for content management
2: Basic understanding of content library benefits but lacks comprehensive approach
3: Strategic thinking suggests ability to develop effective content management
4: Innovative thinking likely to create exceptional content library systems

Goal: Implement streamlined proposal process

0: Not Enough Information Gathered to Evaluate
1: Limited process improvement thinking
2: Some process insights but may not achieve efficiency targets
3: Strategic approach likely to achieve process improvement goals
4: Exceptional process thinking likely to exceed efficiency targets

Recommendation to Proceed

1: Strong No Hire
2: No Hire
3: Hire
4: Strong Hire

Debrief Meeting

Directions for Conducting the Debrief Meeting

The Debrief Meeting is an open discussion for the hiring team members to share the information learned during the candidate interviews. Use the questions below to guide the discussion.

Start the meeting by reviewing the requirements for the role and the key competencies and goals to succeed. Focus specifically on:

Writing and communication skills
Strategic thinking abilities
Project management capabilities
Collaborative approach
Potential to achieve desired outcomes

The meeting leader should strive to create an environment where it is okay to express opinions about the candidate that differ from the consensus or from leadership's opinions. Encourage all participants to share their observations before moving to evaluations.

Scores and interview notes are important data points but should not be the sole factor in making the final decision. Consider how the candidate's specific experiences and capabilities align with your current team composition and company needs.

Any hiring team member should feel free to change their recommendation as they learn new information and reflect on what they've learned.

Questions to Guide the Debrief Meeting

Does anyone have any questions for the other interviewers about the candidate?

Guidance: The meeting facilitator should initially present themselves as neutral and try not to sway the conversation before others have a chance to speak up.

Are there any additional comments about the Candidate?

Guidance: This is an opportunity for all the interviewers to share anything they learned that is important for the other interviewers to know.

How strong were the candidate's writing samples, and do they demonstrate the level of persuasiveness and strategic thinking we need?

Guidance: Focus specifically on the quality of the work sample and any other writing examples shared. Compare against the quality standard required for your proposals.

Do we believe the candidate can manage multiple complex proposals simultaneously in our environment?

Guidance: Consider both their stated experience and any evidence from the interviews that indicates their project management capabilities.

Is there anything further we need to investigate before making a decision?

Guidance: Based on this discussion, you may decide to probe further on certain issues with the candidate or explore specific issues in the reference calls.

Has anyone changed their hire/no-hire recommendation?

Guidance: This is an opportunity for the interviewers to change their recommendation from the new information they learned in this meeting.

If the consensus is no hire, should the candidate be considered for other roles? If so, what roles?

Guidance: Discuss whether engaging with the candidate about a different role would be worthwhile.

What are the next steps?

Guidance: If there is no consensus, follow the process for that situation (e.g., it is the hiring manager's decision). Further investigation may be needed before making the decision. If there is a consensus on hiring, reference checks could be the next step.

Reference Checks

Directions for Conducting Reference Checks

Reference checks are a critical final step in the hiring process for the Proposal Writer and Strategist role. They provide external validation of the candidate's capabilities and performance in previous positions.

When conducting reference checks:

Ask the candidate to provide 2-3 professional references who can speak to their proposal writing and strategic abilities. Ideally, these should include direct supervisors and colleagues from recent positions.
Request that the candidate make an introduction or notify references in advance.
Prepare by reviewing the candidate's resume and interview notes to identify specific areas to explore.
Establish rapport with the reference before diving into detailed questions.
Listen for hesitations, qualifiers, or enthusiasm in responses, not just the content.
Take detailed notes to share with the hiring team.

Focus your questions on verifying the candidate's experience with proposal development, strategic thinking, project management, and collaboration. Be particularly attentive to examples that demonstrate the candidate's ability to develop winning proposals and work effectively under pressure.

Multiple reference checks may be conducted using the same questions, so these can be repeated with different references to establish patterns and consistency.

Questions for Reference Checks

In what capacity did you work with [Candidate], and for how long?

Guidance: Establish the context of the relationship and how well-positioned the reference is to evaluate the candidate's proposal writing and strategic abilities.

What were [Candidate]'s primary responsibilities related to proposal development while working with you?

Guidance: Verify the candidate's claimed responsibilities and role. Listen for alignment with what the candidate shared during interviews.

How would you rate [Candidate]'s writing and communication skills? Can you provide specific examples that demonstrate these skills?

Guidance: Look for concrete examples that validate the candidate's ability to create clear, persuasive content. Ask about any particularly successful proposals or communications.

Can you describe [Candidate]'s approach to developing proposal strategies? What made their approach effective (or not)?

Guidance: Assess whether the reference's description of the candidate's strategic thinking aligns with what you need. Listen for examples of innovative approaches or particularly successful strategies.

How effectively did [Candidate] manage multiple proposals or projects simultaneously? How did they handle tight deadlines?

Guidance: Verify the candidate's project management abilities, particularly under pressure. Ask for examples of challenging situations and how the candidate responded.

How would you describe [Candidate]'s ability to collaborate with different stakeholders, such as subject matter experts or sales teams?

Guidance: Assess the candidate's interpersonal skills and ability to work with diverse team members. Listen for examples of difficult collaborations and how they were handled.

On a scale of 1-10, how likely would you be to hire [Candidate] again for a proposal writing and strategy role? Why?

Guidance: This question often elicits candid feedback. Follow up on the reasoning behind the rating, especially if it's lower than expected.

Reference Check Scorecard

Writing and Communication Skills

0: Not Enough Information Gathered to Evaluate
1: Reference indicates significant concerns about writing quality or clarity
2: Reference suggests adequate but not exceptional writing abilities
3: Reference confirms strong writing skills with specific positive examples
4: Reference enthusiastically praises exceptional writing and communication abilities

Strategic Thinking

0: Not Enough Information Gathered to Evaluate
1: Reference expresses concerns about strategic capabilities
2: Reference describes basic strategic thinking without notable examples
3: Reference confirms effective strategic approach with specific examples
4: Reference highlights exceptional strategic insights with outstanding results

Project Management

0: Not Enough Information Gathered to Evaluate
1: Reference indicates struggles with managing multiple projects or deadlines
2: Reference suggests adequate but sometimes strained project management
3: Reference confirms strong ability to manage multiple projects effectively
4: Reference enthusiastically praises exceptional organization and delivery under pressure

Collaboration and Stakeholder Management

0: Not Enough Information Gathered to Evaluate
1: Reference notes difficulties working with others or managing stakeholders
2: Reference describes adequate collaboration with occasional challenges
3: Reference confirms effective collaboration with diverse stakeholders
4: Reference highlights exceptional relationship-building and collaborative skills

Goal: Increase proposal win rate

0: Not Enough Information Gathered to Evaluate
1: Reference provides little evidence of impact on win rates
2: Reference suggests some positive impact on proposal success
3: Reference confirms significant contribution to improved win rates
4: Reference attributes exceptional win rate improvements directly to candidate

Goal: Develop comprehensive proposal content library

0: Not Enough Information Gathered to Evaluate
1: Reference indicates limited experience with content management
2: Reference describes basic content organization abilities
3: Reference confirms effective development of proposal content resources
4: Reference highlights innovative content management systems implemented

Goal: Implement streamlined proposal process

0: Not Enough Information Gathered to Evaluate
1: Reference suggests limited process improvement contributions
2: Reference describes some process enhancements with modest impact
3: Reference confirms significant process improvements led by candidate
4: Reference enthusiastically credits candidate with transformative process changes

Frequently Asked Questions

How should I adapt this interview guide for our specific industry?

Review the questions and work sample exercise to incorporate industry-specific terminology and scenarios. Focus on proposal types common in your field and adjust competency questions to reflect industry challenges. For technical fields, ensure the work sample tests the ability to translate complex concepts into clear, client-focused language.

What if a candidate has limited formal proposal writing experience but strong writing skills from other contexts?

Focus on transferable skills like strategic thinking, clear writing, research abilities, and project management. The work sample becomes especially important to assess their potential. Look for candidates who demonstrate a quick understanding of proposal fundamentals and show adaptability. Consider their experience with persuasive writing in other formats such as marketing materials or business cases. For more on this approach, see our guide on hiring for potential.

How important is industry knowledge for this role?

While industry knowledge is valuable, the ability to quickly research, understand, and articulate complex concepts is often more important. Strong candidates can come from adjacent industries if they demonstrate exceptional writing, strategic thinking, and collaborative skills. A candidate's learning agility and curiosity often predict success more accurately than specific industry experience.

Should we prioritize strategic thinking or writing skills if we can't find candidates strong in both areas?

This depends on your team composition and immediate needs. If you have strong strategists but need better execution, prioritize writing skills. If your team has solid writers but lacks strategic direction, prioritize strategic thinking. Ideally, look for balanced candidates with strength in both areas, as this combination is what makes exceptional proposal professionals. You might find our article on the science of structured interviewing helpful for making these trade-off decisions.

How can we best evaluate a candidate's ability to handle the pressure of proposal deadlines?

The chronological interview questions about managing multiple proposals provide insight, but also consider creating time pressure in the work sample exercise. Reference checks are particularly valuable for validating a candidate's performance under pressure. Listen for specific examples of how candidates have maintained quality while meeting tight deadlines and how they've prioritized competing demands.

What if our proposal process differs significantly from what the candidate has experienced?

Focus on the candidate's adaptability and learning agility. Ask questions about how they've adjusted to new processes or systems in previous roles. The chronological interview provides opportunities to explore how they've handled transitions between different organizational approaches. Strong candidates will demonstrate openness to new methods and the ability to identify transferable best practices.