Sales Director & Head of Sales Interview Guide
A structured Sales Director interview guide covering revenue strategy, forecast discipline, team coaching and deal judgement — with follow-up probes and a practical scorecard.
Published 2026-08-26 · Reviewed 2026-08-26
Hiring a Sales Director or Head of Sales is one of the most consequential appointments a growing business makes. Get it wrong and you burn pipeline, demoralise a team and lose quarters you cannot recover. This guide gives you a structured framework: evidence to look for, questions to ask with follow-up probes, and a practical scorecard.
These indicators are prompts for structured evaluation, not model answers. Candidates may demonstrate competence through different examples or approaches. An unfamiliar answer is not automatically a weak answer — use follow-up questions before reaching a conclusion. "Not enough evidence" is a valid scorecard outcome. The final decision remains with the human hiring team.
Who this guide is for
For founders, CEOs and hiring managers appointing a Sales Director or Head of Sales for the first time or replacing an underperforming leader.
Role overview
A Sales Director or Head of Sales owns the revenue engine. They set the sales strategy, build and lead the team, manage the pipeline, forecast revenue and are accountable for hitting targets. In smaller companies they may carry a personal quota alongside leadership. In larger organisations they manage managers. The role requires commercial judgement, the ability to lead sellers who are often strong-willed, and the discipline to run a predictable process rather than rely on individual heroics.
How the role varies
At a startup the first sales hire carries a personal quota and builds the playbook from scratch. At a scale-up the role shifts to managing managers and codifying process. In an enterprise, the focus is on forecasting discipline, territory design and cross-functional alignment. B2B enterprise sales demand relationship and stakeholder-management skills that high-velocity transactional or B2C sales do not.
Written and maintained by Kippler. Published — not individually expert-reviewed.
What the interviewer should assess
A Sales Director interview should test four areas: commercial and strategic thinking, pipeline and forecast discipline, team leadership and coaching, and personal credibility with customers and the board. Each matters — a charismatic rainmaker who cannot build a repeatable process is as risky as a process-obsessed manager who cannot win a deal themselves.
Role-specific competencies
Revenue strategy and market judgement
Can they identify which segments, channels and deals to pursue? Do they think about unit economics, not just top-line revenue?
Pipeline and forecast management
Can they run a pipeline that produces a reliable forecast? Do they understand the difference between pipeline volume and pipeline quality?
Team building and coaching
Can they hire, onboard and develop sellers? Do they coach to improve performance, not just manage to a number?
Deal judgment and closing credibility
Can they step into a critical deal and help close it? Do they know when to discount and when to hold firm?
Cross-functional collaboration
Can they work with marketing, product and customer success without turf wars? Do they understand that sales does not exist in isolation?
Integrity and forecast honesty
Will they tell the CEO the truth about the quarter, even when it is bad news? Do they distinguish between genuine commits and hopeful thinking?
Recommended interview structure
A 60-minute first-round interview is a useful starting point for this role, though the appropriate length depends on the interview stage and how many competencies you need to cover. If you can split the assessment across two interviewers, aim for 45 minutes each rather than a single 90-minute session. Structure the discussion in three parts: a brief career discussion (5 minutes), pipeline, forecast and coaching scenarios (35 minutes), and the candidate’s questions for you (10 minutes for a 50-minute session) or (20 minutes for a 60-minute session). Use a specific deal or quarter scenario to test practical judgement rather than asking only about philosophy.
Adapt this guide to your role
This guide is a starting point. Adapt it to your context. At a startup, the first sales hire may carry a personal quota and build the playbook from scratch — test for hands-on selling and process design. At a scale-up, the role shifts to managing managers and codifying process — test for coaching depth and forecast discipline. In an SME, the leader may wear multiple hats across sales and marketing. In a large enterprise, test for territory design, cross-functional alignment and managing managers. B2B enterprise sales demand relationship and stakeholder-management skills that high-velocity transactional sales do not. Regulated industries may require familiarity with compliance constraints on the sales process. A local team needs different leadership from a distributed or hybrid one. Adjust the scenarios to reflect your deal size, sales cycle and go-to-market model.
Interview questions
Ask the same core questions to every candidate for this role. Use the follow-up probes to clarify vague answers and gather more evidence before scoring.
1. Walk me through a quarter where you missed target. What happened, and what did you change?
What this is assessing: Whether they take accountability for misses, not just wins. Whether they can diagnose what went wrong and act on it. Whether they blame the market, the product or the team.
Follow-up probes
- What did the pipeline look like at the start of that quarter versus where it ended up?
- How did you communicate the miss to the wider leadership team?
- Looking back, was there an earlier point where you could have changed course?
Evidence that may indicate strength
- Owns the miss without deflecting
- Diagnoses specific causes: pipeline gap, deal slippage, hiring delay
- Describes concrete changes they made the next quarter
- Can distinguish between a one-off miss and a systemic problem
Points that may require further probing
- Claims an unbroken record of hitting target
- Blames the product, marketing or the market
- Cannot describe what they changed
- Treats the miss as bad luck
2. You inherit a team of five sellers. Three are hitting target, two are not. Walk me through your first 30 days.
What this is assessing: Whether they think about diagnosis before action. Whether they understand the difference between coaching and replacing. Whether they can balance short-term revenue with long-term team health.
Follow-up probes
- What would make you decide to replace rather than coach?
- How would you set expectations with the CEO during those 30 days?
- What specific signals would you look for in the first two weeks?
Evidence that may indicate strength
- Starts by observing and diagnosing, not acting
- Looks at pipeline, activity and skill gaps separately
- Gives the underperformers a genuine chance with a clear plan
- Has a timeline for deciding whether to coach or replace
Points that may require further probing
- Immediately replaces the underperformers
- Applies the same intervention to both without diagnosing
- Focuses only on the number, not the causes
- Has no framework for evaluating seller performance
3. How do you build a forecast you would be comfortable presenting to a board?
What this is assessing: Forecast discipline. Whether they understand probability, commit versus best-case, and the difference between optimism and evidence.
Follow-up probes
- How do you handle a seller who consistently over-commits?
- What is your view on weighting pipeline by stage?
- How far out do you forecast, and how does accuracy change over that horizon?
Evidence that may indicate strength
- Bases commit on evidence, not hope
- Distinguishes between commit, best case and pipeline
- Talks about deal-stage criteria and exit criteria
- Mentions inspecting deals individually, not just rolling up numbers
Points that may require further probing
- Forecasts a percentage of pipeline without qualification
- Conflates commit with best case
- Has no deal-stage methodology
- Treats forecasting as a finance exercise
4. Describe a deal you personally stepped into and helped close. What was your specific contribution?
What this is assessing: Whether they can still sell, not just manage. Whether they understand their role in a deal without taking credit for the seller’s work.
Follow-up probes
- At what point did you decide to get involved, and why then?
- How did the seller feel about your involvement afterwards?
- What would have happened if you had not stepped in?
Evidence that may indicate strength
- Describes a specific deal with a concrete contribution
- Explains why their involvement was necessary
- Credits the seller who owned the relationship
- Identifies what they did differently from the seller
Points that may require further probing
- Describes a deal without explaining their own role
- Takes full credit for a team effort
- Cannot describe a deal they personally influenced recently
- Frames their involvement as overriding the seller
5. How do you decide when to discount and when to hold firm on price?
What this is assessing: Commercial judgement. Whether they understand the strategic value of a deal, not just the revenue. Whether they have a framework rather than winging it.
Follow-up probes
- Can you describe a time you held firm and lost the deal — was that the right call?
- How do you prevent discounting from becoming a pattern with the same customer?
- Who else is involved in the discounting decision?
Evidence that may indicate strength
- Thinks about lifetime value, not just the single deal
- Considers what the discount signals to the customer
- Has a framework: strategic value, competitive pressure, timeline
- Understands that discounting sets a precedent
Points that may require further probing
- Discounts whenever the customer pushes
- Refuses to discount on principle regardless of context
- Has no framework — decides deal by deal without criteria
- Focuses only on closing, not on the deal economics
6. Tell me about a time you had to tell the CEO the quarter was going to miss. How did you handle it?
What this is assessing: Integrity and communication. Whether they deliver bad news early. Whether they bring a plan, not just a problem.
Follow-up probes
- How early did you raise it, and what triggered your confidence that it would miss?
- What did the CEO do with that information?
- Did that experience change how you forecast going forward?
Evidence that may indicate strength
- Communicated early, not at the end of the quarter
- Brought a plan to mitigate, not just the bad news
- Was honest about what was commit and what was at risk
- Distinguishes between a forecast miss and a target miss
Points that may require further probing
- Waited until the quarter ended to report the miss
- Softened the news to the point of being misleading
- Brought no plan to address the gap
- Sees reporting bad news as a failure rather than a responsibility
Practical scorecard
Score each competency separately and record concise evidence supporting your score. Do not allow one impressive answer to inflate unrelated competencies.
Scoring scale
| Competency | Score |
|---|---|
| Revenue strategy and market judgement Can they identify where to focus? Do they think about unit economics? | |
| Pipeline and forecast management Can they build a reliable forecast? Do they understand pipeline quality? | |
| Team building and coaching Can they hire and develop sellers? Do they coach, not just manage? | |
| Deal judgment and closing credibility Can they step into a deal? Do they know when to discount? | |
| Cross-functional collaboration Can they work with marketing and product? Do they avoid turf wars? | |
| Integrity and forecast honesty Will they tell the CEO the truth? Do they separate commit from hope? |
How to use this scorecard
- Score each competency separately.
- Record concise evidence supporting the score.
- Do not allow one impressive answer to inflate unrelated competencies.
- Do not average away a material role-critical concern.
- Discuss scores only after each interviewer has recorded their independent judgement.
- Use the scorecard to support — not replace — the final human decision.
How to run the debrief
Have each interviewer score independently before discussion. Focus the debrief on evidence for forecast discipline and team leadership, as these predict on-the-job performance more reliably than charisma. Distinguish between a candidate who is persuasive in the room and one who demonstrated repeatable process thinking. Pay particular attention to any pattern of vague or shifting answers about pipeline accuracy and forecast methodology — these are harder to coach than product knowledge and can signal underlying issues with sales discipline. If interviewers disagree, ask each to cite the specific evidence behind their score.
Fairness and reasonable adjustments
Sales roles are particularly susceptible to halo effects from confidence and charisma. Ensure every interviewer scores evidence against the same competencies before discussion. Be aware of potential bias towards candidates whose communication style or background matches the existing sales team — the strongest sales leaders come from varied backgrounds. If using a live pitch or role-play scenario, give all candidates the same brief and preparation time. Avoid scoring energy or enthusiasm as a proxy for sales ability; look for evidence of process discipline, forecast accuracy and coaching outcomes.
Candidate experience: Explain the interview format at the beginning. Leave time for the candidate to ask questions. Avoid misleading candidates about the role or the team. Tell them what happens next and the expected timeline. Follow the agreed timing as closely as practical. Avoid repeatedly asking for information already covered in earlier stages.
Questions candidates may ask
Strong candidates will ask questions that reveal their priorities and how they think about the role. Be prepared to answer honestly — misleading a candidate about the role or the team risks a bad hire who leaves quickly.
- What does the current sales pipeline look like, and how reliable is the forecast?
- How is marketing-sourced pipeline performing relative to sales-sourced?
- What does the compensation plan look like, and when was it last reviewed?
- How long do sellers typically stay, and what does the onboarding process look like?
- What authority does this role have over hiring and territory decisions?
Frequently asked questions
Should I ask the candidate to present a 30-60-90 day plan?
A 30-60-90 day plan can test strategic thinking, but be cautious about asking for free work. A discussion about what they would prioritise in their first 90 days is often more informative than a polished document, and it tests improvisational thinking rather than presentation skills.
How do I assess whether they can actually sell, not just manage?
Ask them to describe a specific deal they personally influenced recently. If they cannot, or if every example is years old, they may have moved too far from the frontline. The deal-judgement question above is a good proxy.
What if they have only ever worked in large companies with established sales enablement?
A leader from a large company may struggle in a smaller organisation where they have to build the process, not just run it. Probe what they built versus what they inherited. Ask about hiring their own team from scratch.
How many interview rounds should I run?
One structured interview of 60 to 90 minutes is usually enough for a first round. For a final round, include a scenario discussion with the CEO or a board member to test how they communicate under pressure.
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