Executive Hiring Playbook

EXECUTIVE HIRING PHILOSOPHY

Hiring Leaders at Scale

EXECUTIVE HIRING FUNDAMENTALS

WHY EXEC HIRING IS DIFFERENT:
☐ Higher stakes (wrong hire = 12-18 month setback)
☐ Longer evaluation needed
☐ More stakeholders involved
☐ Compensation complexity
☐ Cultural impact is massive
☐ Harder to course correct

COMMON EXEC HIRING MISTAKES:
☐ Hiring for past company, not current stage
☐ Over-indexing on brand names
☐ Rushing due to urgency
☐ Skipping reference checks
☐ Not assessing leadership style
☐ Ignoring cultural fit
☐ Unclear success criteria
☐ Insufficient board/investor input

WHAT GREAT EXEC HIRES HAVE:
☐ Proven track record at similar stage
☐ Leadership that matches your culture
☐ Strategic thinking + execution
☐ Self-awareness and coachability
☐ Ability to build and develop teams
☐ Comfort with ambiguity

RED FLAGS TO WATCH:
☐ Takes credit, deflects blame
☐ Can't articulate failures/learnings
☐ Answers don't go deep
☐ References hesitate or are vague
☐ Poor self-awareness
☐ Wrong stage experience
☐ Cultural mismatch signals

---

EXEC HIRING PROCESS

Comprehensive Executive Hiring Playbook

═══════════════════════════════════════
PHASE 1: ROLE DEFINITION
═══════════════════════════════════════

BUSINESS CASE:
☐ Why do we need this role now?
☐ What will this person own?
☐ What will success look like at 90 days?
☐ What will success look like at 1 year?
☐ What happens if we don't hire?

ROLE CLARITY:
Title: _______________
Reports to: _______________
Direct reports: _______________
Key responsibilities:
☐ _________________________________
☐ _________________________________
☐ _________________________________
☐ _________________________________
☐ _________________________________

KEY DECISIONS THIS ROLE WILL MAKE:
☐ _________________________________
☐ _________________________________
☐ _________________________________

SUCCESS METRICS:
90-day success:
☐ _________________________________
☐ _________________________________

1-year success:
☐ _________________________________
☐ _________________________________

IDEAL CANDIDATE PROFILE:
Must-have:
☐ _____ years in function
☐ _____ years in leadership
☐ Experience with $___M-$___M companies
☐ Experience with ___-___ person teams
☐ ________________________________

Nice-to-have:
☐ _________________________________
☐ _________________________________
☐ _________________________________

Deal-breakers:
☐ _________________________________
☐ _________________________________

═══════════════════════════════════════
PHASE 2: SEARCH STRATEGY
═══════════════════════════════════════

INTERNAL CANDIDATES:
Candidate         | Readiness | Development Needed
------------------|-----------|-------------------
                  |           |
                  |           |

SEARCH APPROACH DECISION:
☐ Retained search firm ($60-100K, faster)
☐ Contingent search ($30-50K, less dedicated)
☐ Internal recruiting (cheaper, harder)
☐ Network-driven (cheapest, variable)

SEARCH FIRM SELECTION (if applicable):
Firm              | Specialty | Track Record | Fee
------------------|-----------|--------------|-----
                  |           |              |
                  |           |              |
                  |           |              |

Selected: _______________
Reason: _______________

TARGET COMPANIES:
Company           | Why       | Potential Candidates
------------------|-----------|---------------------
                  |           |
                  |           |
                  |           |
                  |           |

NETWORK ACTIVATION:
☐ Board members to contact
☐ Investors to contact
☐ CEO peers to contact
☐ Functional peers to contact
☐ Former colleagues to contact

═══════════════════════════════════════
PHASE 3: INTERVIEW PROCESS
═══════════════════════════════════════

INTERVIEW STAGES:

ROUND 1 - INITIAL SCREEN (60 min)
Interviewer: Recruiter or CEO
Focus: Background, interest, high-level fit
Questions:
☐ Walk me through your career
☐ Why are you interested in this role?
☐ What are you looking for in your next role?
☐ What's your leadership style?
☐ What questions do you have?
Pass/fail criteria: _______________

ROUND 2 - CEO DEEP DIVE (90 min)
Interviewer: CEO
Focus: Strategy, leadership, cultural fit
Questions:
☐ Tell me about your biggest achievement
☐ Tell me about your biggest failure
☐ How would you approach first 90 days?
☐ How do you build and develop teams?
☐ What's your decision-making style?
☐ How do you handle conflict?
Pass/fail criteria: _______________

ROUND 3 - LEADERSHIP TEAM (60 min each)
Interviewers: 2-3 key executives
Focus: Collaboration, cross-functional fit
Questions:
☐ How would you work with [function]?
☐ Tell me about cross-functional wins
☐ How do you handle disagreements?
☐ What would you need from peers?
Pass/fail criteria: _______________

ROUND 4 - CASE/WORK SESSION (90-120 min)
Interviewer: Hiring manager + team
Focus: Problem-solving, thinking style
Format:
☐ Present real business challenge
☐ Have candidate present approach
☐ Discuss and pressure-test
☐ Assess thinking quality
Pass/fail criteria: _______________

ROUND 5 - BOARD/INVESTOR (optional, 45-60 min)
Interviewer: Key board member
Focus: Strategic thinking, investor readiness
Questions:
☐ How would you present to board?
☐ What metrics would you track?
☐ How do you think about the market?
Pass/fail criteria: _______________

ROUND 6 - FINAL & REFERENCES
Activities:
☐ Back-channel references (3+)
☐ Formal references (3+)
☐ Final CEO conversation
☐ Offer preparation

═══════════════════════════════════════
PHASE 4: ASSESSMENT & REFERENCES
═══════════════════════════════════════

INTERVIEW DEBRIEF FORMAT:
For each interviewer:
☐ Overall rating (1-5)
☐ Strengths observed
☐ Concerns identified
☐ Questions remaining
☐ Hire/No hire recommendation

REFERENCE CHECK TEMPLATE:
Reference: _______________
Relationship: _______________
Duration: _______________

Questions:
☐ How do you know [candidate]?
☐ What was their role/responsibility?
☐ What are their greatest strengths?
☐ What are their development areas?
☐ How would you describe their leadership?
☐ How did they handle [specific situation]?
☐ Would you work with them again?
☐ On a scale of 1-10, how would you rate them?
☐ What should I know that I haven't asked?

BACK-CHANNEL REFERENCES:
☐ At least 3 not provided by candidate
☐ Ask same questions
☐ Look for patterns

═══════════════════════════════════════
PHASE 5: OFFER & CLOSE
═══════════════════════════════════════

COMPENSATION PACKAGE:
Base salary: $_____
Target bonus: ___% = $_____
Total cash: $_____
Equity: _____% (_____ shares)
Sign-on bonus: $_____
Other benefits: _______________

OFFER CONVERSATION APPROACH:
☐ Understand their priorities
☐ Present package thoughtfully
☐ Be prepared to negotiate
☐ Know your limits
☐ Don't lowball

COMMON NEGOTIATION POINTS:
☐ Base salary
☐ Equity (amount, vesting, acceleration)
☐ Title
☐ Start date
☐ Sign-on bonus
☐ Relocation support

CLOSING THE CANDIDATE:
☐ Why this role matters
☐ Why they specifically
☐ Vision for their impact
☐ Address remaining concerns
☐ Create urgency appropriately

Executive Assessment Matrix

Criteria	Weight	Score (1-10)	Weighted	Notes
Functional expertise	20%
Leadership track record	20%
Strategic thinking	15%
Cultural fit	15%
Stage experience	15%
Team building	10%
Growth potential	5%
TOTAL	100%		/10

Executive Hiring Timeline

Phase	Duration	Key Activities
Role definition	1-2 weeks	Align on role, compensation
Search launch	1-2 weeks	Kickoff, sourcing begins
Candidate pipeline	3-6 weeks	Screen, identify finalists
Interviews	2-4 weeks	All rounds completed
References & offer	1-2 weeks	Checks, package, close
Total timeline	8-16 weeks

---