Successful sales leadership requires more than just hitting targets — it demands a strategic mind, coaching ability, and a talent for building high-performing teams that can adapt to changing market conditions. The Head of Sales position sits at the intersection of leadership and revenue generation, serving as the architect of sales strategy while developing the people who execute it.

A Head of Sales is crucial for companies looking to scale revenue operations and build predictable, repeatable sales processes. This role bridges the gap between executive leadership and frontline sales teams, translating company vision into actionable sales strategies. From establishing sales methodologies to coaching managers, the Head of Sales creates the infrastructure needed for sustainable growth.

When evaluating candidates for this position, interviewers should focus on past behaviors as predictors of future performance. The most effective approach involves asking candidates to describe specific situations they've faced, the actions they took, and the results they achieved. Follow-up questions are essential for digging deeper into their responses and understanding their thought processes, leadership philosophies, and problem-solving approaches.

By using behavioral interview techniques, you can effectively evaluate a candidate's fit for your organization and identify those who will truly excel in driving your sales organization forward. Preparation is key to getting the most out of these interviews, so take time to design your hiring process carefully before beginning candidate evaluations.

Interview Questions

Tell me about a time when you transformed an underperforming sales team into a high-achieving one. What approach did you take and what were the results?

Areas to Cover:

• Initial assessment of the team's challenges and performance gaps
• Specific changes implemented in strategy, process, or personnel
• How the candidate gained buy-in from the team and other stakeholders
• Metrics used to measure improvement
• Timeline for achieving significant results
• Obstacles encountered and how they were overcome
• Long-term sustainability of the improvements

Follow-Up Questions:

• What resistance did you encounter when implementing changes, and how did you address it?
• How did you identify which team members could improve with coaching versus those who might not be a good fit?
• What specific coaching techniques proved most effective in this situation?
• How did you balance short-term results with long-term team development?

Describe your approach to sales forecasting and pipeline management. How have you improved forecast accuracy and pipeline health in your previous role?

Areas to Cover:

• Methodology used for sales forecasting
• Tools and technologies implemented
• How the candidate trained the team on pipeline management
• Process changes that were instituted
• Metrics used to monitor pipeline health
• Improvement in forecast accuracy (with specific numbers)
• Impact on business planning and revenue predictability

Follow-Up Questions:

• How did you hold sales managers accountable for their forecasts?
• What leading indicators did you find most valuable in predicting sales outcomes?
• How did you handle situations where actual results significantly deviated from forecasts?
• How did improved forecasting affect other departments' ability to plan and execute?

Share an example of how you've successfully aligned your sales strategy with changing market conditions or business priorities.

Areas to Cover:

• The specific market shift or business change that required adaptation
• Process for gathering market intelligence
• How the sales strategy was modified
• Changes to team structure, territories, or compensation
• Communication approach with the team
• Timeline for implementation
• Results achieved after the strategic shift
• Lessons learned from the experience

Follow-Up Questions:

• How did you identify the need to change before it became a crisis?
• What resistance did you encounter from your team, and how did you overcome it?
• How did you balance maintaining current performance while implementing new approaches?
• What metrics did you use to validate that the new strategy was working?

Tell me about your approach to coaching sales managers. What specific methods have you found most effective in developing strong sales leaders?

Areas to Cover:

• Philosophy on manager development
• Structured approach to coaching (frequency, format, content)
• How coaching priorities were determined
• Tools or frameworks used
• Examples of a manager who significantly improved under their guidance
• How coaching effectiveness was measured
• Balance between performance management and development

Follow-Up Questions:

• How do you adapt your coaching approach for different leadership styles or experience levels?
• What's your process for identifying future leadership talent within the sales organization?
• How do you ensure managers are effectively coaching their own teams?
• Can you share a specific example of a challenging coaching situation and how you handled it?

Describe a time when you had to make difficult decisions about your sales team structure or personnel to meet business objectives.

Areas to Cover:

• Context of the business challenge necessitating changes
• Analysis conducted to inform decisions
• Specific changes made to team structure, roles, or personnel
• How decisions were communicated to affected individuals and the broader team
• Impact on team morale and performance
• Management of transitions
• Business outcomes of the restructuring

Follow-Up Questions:

• How did you support team members through the transition?
• What criteria did you use when making decisions about role changes or reductions?
• How did you rebuild team momentum after the changes?
• What would you do differently if faced with a similar situation in the future?

Share an example of how you've successfully collaborated with other departments (Marketing, Product, Customer Success) to achieve revenue goals.

Areas to Cover:

• The specific cross-functional initiative
• Challenges in alignment between departments
• Process created for collaboration
• Personal role in facilitating cooperation
• How conflicts or different priorities were resolved
• Metrics used to track joint success
• Outcomes achieved through collaboration
• Lasting impact on interdepartmental relationships

Follow-Up Questions:

• How did you handle situations where other departments had conflicting priorities?
• What structures or processes did you put in place to ensure ongoing collaboration?
• How did you ensure sales team input was incorporated into product roadmaps or marketing campaigns?
• What did you learn about effective cross-functional leadership from this experience?

Tell me about a time when you had to enter a new market or launch a new product. How did you approach this challenge?

Areas to Cover:

• Initial research and preparation
• Strategy development process
• How the go-to-market plan was created
• Team preparation and training approach
• Adjustments made based on early market feedback
• Metrics used to evaluate success
• Results achieved compared to targets
• Key learnings from the experience

Follow-Up Questions:

• How did you identify and develop the right talent for this new initiative?
• What unexpected challenges arose, and how did you adapt?
• How did you balance resources between existing business and new opportunities?
• What would you do differently if launching a similar initiative in the future?

Describe a situation where you had to turn around declining sales performance in a key product line or market segment.

Areas to Cover:

• Analysis conducted to understand the decline
• Root causes identified
• Strategy developed to address issues
• Specific actions taken to improve performance
• How you gained buy-in from the team and leadership
• Timeline for recovery
• Metrics used to track progress
• Results achieved after intervention

Follow-Up Questions:

• How did you prioritize which issues to address first?
• What resistance did you encounter to your turnaround plan, and how did you overcome it?
• How did you maintain team motivation during challenging times?
• What early indicators helped you confirm your approach was working?

Share an example of how you've used data and analytics to improve sales performance or processes.

Areas to Cover:

• The specific performance challenge or opportunity
• Data sources and analysis methods used
• Insights generated from the analysis
• How insights were translated into action plans
• Implementation approach with the team
• Change management aspects
• Results achieved through data-driven changes
• How continuous improvement was maintained

Follow-Up Questions:

• How did you ensure your team understood and acted on the data?
• What challenges did you face in gathering reliable data?
• How did you balance data-driven decisions with experience and intuition?
• How did you build a more data-driven culture within your sales organization?

Tell me about a time when you had to build or rebuild a sales culture. What was your approach and what results did you achieve?

Areas to Cover:

• Initial assessment of the existing culture
• Vision for the desired culture
• Specific elements requiring change
• Methods used to shape culture (recognition, communication, etc.)
• How values and behaviors were reinforced
• Timeline for significant culture change
• Resistance encountered and how it was addressed
• Evidence that culture change was successful

Follow-Up Questions:

• How did you identify the cultural elements that needed to change?
• What formal and informal mechanisms did you use to reinforce desired behaviors?
• How did you handle team members who weren't adapting to the new culture?
• What surprised you most about the culture change process?

Describe how you've developed and implemented a successful sales enablement program or initiative.

Areas to Cover:

• Needs assessment process
• Program design and content development
• Delivery methods and technology platforms used
• How program effectiveness was measured
• Team adoption rates and feedback
• Impact on sales performance metrics
• Continuous improvement process
• Budget and resource management

Follow-Up Questions:

• How did you ensure the program addressed real-world sales challenges?
• What resistance did you encounter from the sales team, and how did you overcome it?
• How did you balance time for enablement with time for selling activities?
• What technologies proved most valuable in your enablement efforts?

Tell me about a significant challenge you faced in hitting revenue targets and how you overcame it.

Areas to Cover:

• Nature and scope of the challenge
• Analysis conducted to understand factors affecting performance
• Strategy developed to address the gap
• How resources were allocated or reallocated
• Communication with leadership and the team
• Specific actions that had the most impact
• Timeline for recovery
• Final results achieved

Follow-Up Questions:

• How did you maintain team morale during this challenging period?
• What early warning signs did you miss that might have allowed for earlier intervention?
• How did you balance short-term actions with longer-term solutions?
• How did this experience change your approach to planning and risk management?

Share an example of how you've successfully managed change during a significant transition, such as a merger, acquisition, or major strategic shift.

Areas to Cover:

• Context of the change situation
• How the change was communicated to the team
• Strategy for maintaining performance during transition
• How resistance or concerns were addressed
• Support provided to team members
• Timeline for stabilization
• Impact on key performance indicators
• Lessons learned about change management

Follow-Up Questions:

• What were the biggest challenges in maintaining team focus during the transition?
• How did you identify and support at-risk team members during this period?
• What would you do differently if managing a similar transition again?
• How did you as a leader model the appropriate response to change?

Describe a situation where you had to make a significant strategic decision for your sales organization with incomplete information.

Areas to Cover:

• Context requiring the decision
• Available information and critical unknowns
• Process used to evaluate options
• How risks were assessed and mitigated
• How the decision was communicated and implemented
• Adjustments made as more information became available
• Ultimate outcome of the decision
• Lessons learned about decision-making under uncertainty

Follow-Up Questions:

• How did you balance the need for speed with the desire for more complete information?
• What frameworks or principles guided your decision-making process?
• How did you gain buy-in from stakeholders given the uncertainties?
• What contingency plans did you put in place?

Tell me about a time when you identified and developed a high-potential individual who went on to significant achievement.

Areas to Cover:

• How the individual's potential was identified
• Development plan created
• Specific coaching or mentoring provided
• Opportunities created for growth and visibility
• Challenges encountered in their development
• Support provided during setbacks
• The individual's ultimate achievements
• Impact on the wider organization

Follow-Up Questions:

• What qualities or behaviors helped you identify this person's potential?
• How did you tailor your development approach to their specific needs?
• What challenging feedback did you need to deliver, and how did you approach it?
• How has this experience shaped your approach to talent development?

Frequently Asked Questions

What makes behavioral interview questions particularly effective for Head of Sales candidates?

Behavioral questions reveal how candidates have actually handled leadership challenges in the past, which is a stronger predictor of future performance than hypothetical questions. For a Head of Sales role, these questions help assess leadership approach, strategic thinking, coaching ability, and results orientation based on real experiences rather than theoretical knowledge.

How many behavioral questions should I include in a Head of Sales interview?

Quality trumps quantity. Rather than rushing through many questions, focus on 3-4 well-chosen behavioral questions per interview session, allowing time for thorough follow-up. This approach yields deeper insights than covering more questions superficially. A complete Head of Sales interview process might include 3-4 interview sessions with different interviewers focusing on different competencies.

How should I evaluate the responses to these behavioral questions?

Listen for specificity in the examples provided, clear articulation of the candidate's personal role and actions, demonstrated strategic thinking, evidence of people development, and measurable results. The strongest candidates will provide concrete examples with business context, explain their thought process, and share quantifiable outcomes and learnings.

Should I focus more on past results or leadership approach when evaluating Head of Sales candidates?

Both are important, but they must be evaluated in context. Sales results should be assessed relative to targets, market conditions, and available resources. Leadership approach should be evaluated based on how the candidate builds and develops teams, handles challenges, and creates sustainable success rather than just short-term wins. The ideal candidate demonstrates both strong results and effective leadership methods.

How can I adapt these questions for candidates coming from different industries?

Focus on the underlying leadership competencies rather than industry-specific knowledge. A strong Head of Sales candidate should be able to explain how their leadership approach, sales methodology, and team development strategies would transfer to your industry, even if the specifics of the product or market are different. Ask follow-up questions about how they've adapted to new industries or markets in the past.

Interested in a full interview guide for a Head of Sales role? Sign up for Yardstick and build it for free.