Assertiveness in a sales management context refers to the ability to confidently express opinions, make decisions, and stand up for one's team's interests while still maintaining professional relationships. It involves communicating directly, negotiating effectively, setting appropriate boundaries, and advocating for resources and support needed for team success.

For sales managers, assertiveness is crucial for driving results in high-pressure environments where competing priorities often clash. An assertive sales manager can effectively negotiate targets with senior leadership, advocate for their team's needs, provide direct and constructive feedback to team members, and navigate conflicts with other departments. This competency manifests in various dimensions, including confident decision-making, constructive challenge, boundary setting, direct communication, and effective negotiation.

When evaluating candidates for assertiveness, focus on specific examples where they've demonstrated the courage to stand up for their convictions while maintaining positive relationships. Listen for instances where they've balanced being firm with being diplomatic, how they've approached difficult conversations, and situations where they've challenged the status quo to drive better outcomes. The behavioral interview questions below will help you identify candidates who can assertively lead sales teams to success.

Interview Questions

Tell me about a time when you had to push back on unrealistic sales targets or expectations from senior leadership.

Areas to Cover:

• The specific situation and why the expectations were unrealistic
• How the candidate prepared for the conversation
• The approach they took to communicate their position
• What data or evidence they used to support their case
• How they maintained a constructive relationship during the disagreement
• The outcome of the situation
• Lessons learned about effective pushback

Follow-Up Questions:

• What made you decide this was worth pushing back on rather than just trying to meet the expectations?
• How did you balance being assertive with showing respect for leadership's perspective?
• What would you do differently if you faced a similar situation today?
• How did this experience influence how you handle similar situations now?

Describe a situation where you had to say "no" to a customer or client request while preserving the relationship.

Areas to Cover:

• The specific request and why it couldn't be accommodated
• How the candidate prepared for delivering the news
• The communication approach they chose
• How they managed the client's reaction
• Alternative solutions they offered, if any
• The impact on the client relationship
• What they learned about setting boundaries

Follow-Up Questions:

• What principles guided your decision to decline the request?
• How did you coach your team through handling similar situations?
• What signals indicated it was better to say no rather than trying to accommodate?
• How did this experience shape your approach to client expectations?

Share an example of when you had to mediate a conflict between two sales team members or between your team and another department.

Areas to Cover:

• The nature of the conflict and the stakes involved
• The candidate's initial assessment of the situation
• How they approached the parties involved
• Specific techniques used to facilitate resolution
• How they asserted their authority if necessary
• The outcome of the mediation
• Impact on team dynamics or interdepartmental relationships

Follow-Up Questions:

• What made you decide to address this conflict directly rather than hoping it would resolve itself?
• How did you ensure all parties felt heard while still moving toward resolution?
• What principles guided your approach to the mediation?
• How have you applied what you learned to prevent similar conflicts?

Tell me about a time when you advocated for resources, tools, or support that your sales team needed to be successful.

Areas to Cover:

• The specific resources needed and why they were important
• How the candidate built their business case
• The resistance or objections they encountered
• How they persisted despite initial pushback
• Their approach to negotiation
• The outcome and impact on team performance
• Lessons learned about effective advocacy

Follow-Up Questions:

• How did you determine this was worth fighting for?
• What strategies did you use to influence decision-makers?
• How did you involve your team in the process?
• What would you do differently if you faced similar resistance today?

Describe a situation where you had to provide difficult feedback to a sales representative who was underperforming.

Areas to Cover:

• The performance issue and its impact
• How the candidate prepared for the conversation
• Their approach to delivering the feedback
• How they balanced directness with support
• The employee's reaction and how they managed it
• The follow-up plan they implemented
• The outcome of the situation

Follow-Up Questions:

• What made this feedback particularly challenging to deliver?
• How did you ensure the feedback was specific and actionable?
• How did you follow up after the initial conversation?
• What did you learn about delivering difficult feedback from this experience?

Share an example of when you challenged an established sales process or strategy because you believed there was a better approach.

Areas to Cover:

• The existing process/strategy and its limitations
• How the candidate identified the opportunity for improvement
• How they built support for their alternative approach
• The resistance they encountered
• How they persisted while maintaining relationships
• The outcome of their challenge
• Impact on sales results

Follow-Up Questions:

• What gave you the confidence to challenge the established way of doing things?
• How did you balance respect for existing processes with the need for improvement?
• How did you respond to skepticism or resistance?
• What did this experience teach you about driving change as a sales leader?

Tell me about a time when you had to negotiate with another department for support or resources critical to your sales team's success.

Areas to Cover:

• The specific support needed and why it was important
• The competing priorities that created tension
• How the candidate prepared for the negotiation
• Their approach to finding mutual benefit
• How they asserted their team's needs
• The outcome of the negotiation
• Impact on cross-departmental relationships

Follow-Up Questions:

• How did you identify the other department's priorities and constraints?
• What strategies did you use to influence without formal authority?
• How did you handle moments of tension during the negotiation?
• What would you do differently in a similar negotiation today?

Describe a situation where you had to make an unpopular decision that impacted your sales team.

Areas to Cover:

• The decision and what made it necessary
• How the candidate evaluated options
• Their approach to communicating the decision
• How they addressed resistance or pushback
• How they stood firm while showing empathy
• The ultimate impact of the decision
• Lessons learned about leadership courage

Follow-Up Questions:

• How did you prepare yourself to stand firm despite anticipated resistance?
• What principles guided your decision-making process?
• How did you rebuild team morale or buy-in after making the unpopular decision?
• What signals told you this was the right decision despite its unpopularity?

Share an example of when you had to defend your sales team against criticism or blame from other parts of the organization.

Areas to Cover:

• The specific situation and nature of the criticism
• The candidate's assessment of the validity of the criticism
• How they gathered facts before responding
• Their approach to the conversation
• How they balanced team defense with accountability
• The resolution of the situation
• Impact on team morale and cross-functional relationships

Follow-Up Questions:

• How did you decide which criticisms to accept and which to push back on?
• How did you communicate with your team about the situation?
• What strategies did you use to keep the conversation productive rather than adversarial?
• How did this experience affect how you handle similar situations now?

Tell me about a time when you had to assert yourself with a difficult customer or client to protect your company's interests.

Areas to Cover:

• The specific situation and what made it challenging
• How the candidate assessed the situation
• Their approach to the conversation
• How they balanced client relationship with company interests
• Techniques used to de-escalate while remaining firm
• The outcome of the situation
• Lessons learned about assertiveness with clients

Follow-Up Questions:

• What principles guided your approach to this situation?
• How did you prepare for this difficult conversation?
• What techniques did you use to remain composed while being assertive?
• How did you coach your team based on what you learned from this experience?

Describe a situation where you had to set clear expectations with your sales team about performance or behavior that wasn't negotiable.

Areas to Cover:

• The specific expectations and why they were important
• How the candidate determined these were non-negotiable
• Their approach to communicating the expectations
• How they handled pushback or resistance
• Follow-up actions to ensure compliance
• The outcome and impact on team culture
• What they learned about setting firm boundaries

Follow-Up Questions:

• How did you distinguish between negotiable and non-negotiable expectations?
• What techniques did you use to communicate firmness while maintaining respect?
• How did you follow through to ensure expectations were being met?
• How has your approach to setting expectations evolved based on this experience?

Share an example of when you had to escalate an issue to senior leadership because it wasn't being adequately addressed at your level.

Areas to Cover:

• The issue and why escalation was necessary
• How the candidate tried to resolve it at their level first
• How they prepared their case for escalation
• Their approach to the escalation conversation
• How they maintained relationships with those they bypassed
• The outcome of the escalation
• Lessons learned about effective escalation

Follow-Up Questions:

• How did you decide this issue warranted escalation?
• How did you frame the issue to get leadership's attention and support?
• How did you handle any tension with peers whose areas were involved?
• What did this experience teach you about when and how to escalate issues?

Tell me about a time when you had to stand your ground on a sales strategy or approach despite pressure to change course.

Areas to Cover:

• The strategy and why the candidate believed in it
• The source and nature of the pressure to change
• How they evaluated whether to hold firm or adjust
• How they communicated their position
• Data or evidence they used to support their stance
• The outcome of holding their ground
• What they learned about conviction in leadership

Follow-Up Questions:

• What gave you the confidence that your approach was right despite the pressure?
• How did you distinguish between beneficial feedback and distractions?
• How did you keep your team aligned during this period of pressure?
• What would make you reconsider your position in a similar situation?

Describe a situation where you had to have a difficult conversation with a peer or superior about how their actions were affecting your sales team.

Areas to Cover:

• The specific situation and its impact on the team
• How the candidate prepared for the conversation
• Their approach to addressing the issue directly
• How they maintained respect while being assertive
• The other person's reaction and how they managed it
• The resolution and outcomes
• Lessons learned about peer/upward feedback

Follow-Up Questions:

• What made you decide to address this directly rather than working around it?
• How did you prepare for potential defensive reactions?
• What techniques did you use to keep the conversation constructive?
• How has this experience influenced how you approach similar situations?

Share an example of when you had to push your sales team to stretch beyond their comfort zone to achieve ambitious goals.

Areas to Cover:

• The specific goals and why they required stretching
• How the candidate assessed team capabilities
• Their approach to communicating expectations
• How they balanced pushing with supporting
• How they handled resistance or fear
• The outcome of their assertive leadership
• What they learned about motivating stretch performance

Follow-Up Questions:

• How did you determine how far to push without breaking morale?
• What support mechanisms did you put in place as you raised expectations?
• How did you handle team members who struggled with the higher expectations?
• What indicators told you when to keep pushing versus when to adjust?

Frequently Asked Questions

Why is assertiveness particularly important for sales managers?

Sales managers operate at the intersection of multiple competing interests - their team's needs, customer demands, company goals, and other departments' priorities. Assertiveness allows them to effectively advocate for their team, negotiate realistic targets, give direct feedback, and resolve conflicts that could otherwise hinder performance. Without assertiveness, sales managers often struggle to secure resources, protect their team from unreasonable demands, or drive necessary changes.

How can I tell the difference between healthy assertiveness and aggressiveness in a candidate?

Assertive candidates stand up for their needs and opinions while still respecting others. They'll describe situations where they were direct but maintained relationships, listened to opposing viewpoints, and sought mutually beneficial solutions when possible. Aggressive candidates may describe "winning" at others' expense, dismissing opposing viewpoints, or creating unnecessary conflict. Look for candidates who can balance firmness with diplomacy and describe how they've maintained positive relationships even through disagreements.

Should I ask these questions even for entry-level sales manager roles?

Yes, though you might focus more on questions about providing feedback to team members, standing up for team needs, or resolving conflicts at their level. Even first-time managers need assertiveness to be effective. For senior roles, emphasize questions about challenging organizational direction, negotiating with executives, or defending team interests against powerful stakeholders.

How many of these questions should I include in an interview?

For a comprehensive assessment, include 3-4 assertiveness questions in your interview plan. Choose questions that match the specific demands of your sales environment - if cross-departmental friction is common, focus on questions about interdepartmental negotiation. If your organization is undergoing change, prioritize questions about challenging processes or standing firm during uncertainty.

What red flags should I watch for in candidates' responses to these questions?

Watch for candidates who: 1) Can't provide specific examples of assertive behavior, 2) Describe situations where they avoided necessary conflict, 3) Show disrespect for others while being "assertive," 4) Fail to balance assertiveness with relationship building, or 5) Don't demonstrate learning and growth in their approach to assertiveness over time.

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