Talent Onboarding Guide #4
You've won the engagement. The SOW is signed. Your first day is approaching. Now comes the real test: can you deliver the transformation you promised?
The first 90 days of a fractional engagement are make-or-break. Get them right, and you'll build a strategic partnership that could last years and generate significant referrals. Get them wrong, and you'll struggle to renew, damage your reputation, and potentially lose a valuable reference.
The pressure is intense. You're working part-time but expected to deliver full-time impact. You're an outsider who needs to quickly become a trusted insider. You have limited time to understand complex business dynamics while simultaneously driving meaningful change.
Most experienced executives underestimate this challenge. They assume their expertise will automatically translate into fractional success. But fractional leadership requires a different skill set: rapid relationship building, accelerated context acquisition, and the ability to drive change without traditional authority structures.
The fractional leadership paradox
You need to go fast and slow simultaneously
Go fast on: Demonstrating value, building credibility, delivering quick wins
Go slow on: Understanding context, building relationships, making major changes
You need to be confident but humble
Confident about: Your expertise, methodology, and ability to solve problems
Humble about: Company culture, internal dynamics, and existing relationships
You need to lead without authority
Unlike full-time executives, you can't rely on organisational hierarchy. Your influence comes from expertise, results, and relationships – not job titles.
The 90-day framework: Prove, Build, Scale
Days 1-30: Prove (Establish credibility and deliver quick wins)
Primary goals:
- Demonstrate you understand their business and challenges
- Deliver visible improvements that validate your approach
- Build relationships with key stakeholders
- Establish working rhythms and communication patterns
Success metrics:
- At least 2-3 quick wins implemented
- Positive feedback from key stakeholders
- Clear understanding of business context and culture
- Well-defined priorities for next 60 days
Days 31-60: Build (Implement systems and develop capabilities)
Primary goals:
- Implement core systems and processes
- Develop internal team capabilities
- Drive measurable improvements in key metrics
- Establish yourself as a strategic partner
Success metrics:
- Core systems operational and showing results
- Team members developing new capabilities
- Measurable progress against SOW objectives
- Strategic input valued by leadership team
Days 61-90: Scale (Optimize performance and plan sustainability)
Primary goals:
- Optimize systems for maximum impact
- Ensure sustainability without your constant involvement
- Plan for ongoing engagement or transition
- Establish foundation for renewal/expansion
Success metrics:
- Systems operating effectively with minimal oversight
- Team capable of maintaining improvements
- Clear evidence of ROI on your engagement
- Renewal conversation initiated based on results
Week-by-week playbook
Week 1: Foundation setting
Days 1-2: Deep context immersion
- Review all provided materials thoroughly
- Conduct 1:1 meetings with key stakeholders (30-45 minutes each)
- Understand current state through data, not just opinions
- Map organizational dynamics and decision-making processes
Day 3: Quick assessment
- Identify 3-5 immediate opportunities for improvement
- Validate your initial hypotheses with data
- Prioritize based on impact and effort required
- Plan your first quick wins
Days 4-5: Relationship building and planning
- Meet with broader team members who'll be affected by your work
- Understand existing tools, systems, and processes
- Create 30-60-90 day detailed plan
- Establish communication rhythms and preferences
Week 2: Quick wins execution
Focus: Implement 2-3 small improvements that demonstrate value immediately
Examples by function:
- Marketing: Fix obvious website issues, optimize underperforming campaigns, improve lead handoff process
- Operations: Streamline bottleneck processes, implement simple automation, improve reporting accuracy
- Technology: Address immediate technical debt, improve deployment processes, enhance monitoring
- Sales: Optimize sales collateral, improve CRM hygiene, streamline proposal processes
Communication: Share early wins with stakeholders to build confidence
Week 3: System design
Focus: Design the core systems and processes you'll implement
Activities:
- Map current state vs. desired future state
- Design new processes with team input
- Plan implementation sequence
- Identify potential resistance and mitigation strategies
Key principle: Involve the team in design to ensure buy-in and adoption
Week 4: Initial implementation
Focus: Begin implementing core systems while maintaining momentum
Activities:
- Start rolling out designed systems
- Train team members on new processes
- Establish measurement and feedback loops
- Conduct first formal progress review
Deliverable: 30-day assessment report showing quick wins achieved and plan for next 60 days
Weeks 5-8: Core system implementation
Focus: Implement the main systems and processes that will drive long-term value
Weekly rhythm:
- Monday: Priority setting and team alignment
- Mid-week: Hands-on implementation and problem-solving
- Friday: Progress review and next week planning
Key activities:
- Roll out core systems in phases
- Train team members and develop their capabilities
- Monitor metrics and adjust approach based on results
- Address resistance and adoption challenges
Stakeholder management: Regular updates showing progress against SOW objectives
Weeks 9-12: Optimization and scaling
Focus: Refine systems for maximum impact and prepare for sustainability
Activities:
- Optimize processes based on initial results
- Develop team members to maintain systems independently
- Document processes and best practices
- Plan for ongoing measurement and improvement
Strategic focus: Position yourself for renewal by demonstrating ongoing value
Relationship building strategies
Understand the power dynamics
Formal authority: Who officially makes decisions? Informal influence: Who actually influences decisions? Coalition building: Who are your natural allies? Potential resistance: Who might be skeptical of change?
Build trust through competence and character
Competence signals:
- Asking insightful questions that reveal expertise
- Providing valuable input in meetings
- Delivering on commitments consistently
- Solving problems others can't
Character signals:
- Giving credit to team members for successes
- Taking responsibility when things don't go as planned
- Showing genuine interest in their success
- Maintaining confidentiality appropriately
Adapt your communication style
For analytical types: Lead with data and logical reasoning For relationship-focused types: Emphasize collaboration and people impact For results-oriented types: Focus on outcomes and efficiency For creative types: Emphasize innovation and possibilities
Common first 90-day mistakes
Moving too fast on major changes
The mistake: Trying to implement everything at once without building foundation support.
Why it fails: Creates resistance, overwhelms the team, and increases failure risk.
Better approach: Sequence changes logically, building on early wins to create momentum.
Not investing enough in relationships
The mistake: Focusing entirely on deliverables while neglecting stakeholder relationships.
Why it fails: Even great work can fail without internal support and adoption.
Better approach: Invest 40% of your time in relationship building during the first month.
Being too prescriptive
The mistake: Telling people exactly what to do without involving them in solution design.
Why it fails: Creates dependency and resistance rather than capability and ownership.
Better approach: Involve team members in designing solutions they'll need to implement.
Ignoring company culture
The mistake: Implementing solutions that work elsewhere without adapting to local culture.
Why it fails: Culture eats strategy for breakfast, especially for part-time leaders.
Better approach: Adapt your approach to work within existing cultural norms.
Not measuring and communicating progress
The mistake: Assuming good work speaks for itself.
Why it fails: Stakeholders may not recognize value without clear communication.
Better approach: Establish metrics early and communicate progress regularly.
Proving ROI and building renewal case
Track leading and lagging indicators
Leading indicators (show early progress):
- Process improvements implemented
- Team capability development
- System adoption rates
- Stakeholder satisfaction scores
Lagging indicators (show business impact):
- Revenue or cost metrics
- Efficiency improvements
- Customer satisfaction changes
- Team performance improvements
Document everything
Progress tracking:
- Weekly accomplishment summaries
- Before/after comparisons
- Stakeholder feedback collection
- Metric improvements over time
Story development:
- Specific examples of problems solved
- Quantified business impact
- Team member development stories
- Process improvement case studies
Communicate value proactively
Monthly reports should include:
- Progress against SOW objectives
- Key accomplishments and wins
- Metrics improvements
- Challenges addressed
- Plan for next month
Stakeholder feedback:
- Regular check-ins with key stakeholders
- Formal feedback collection at 30 and 60 days
- Documentation of positive feedback
- Address concerns proactively
Setting up renewal conversations
Start renewal discussions at day 60
Why early: Gives time to address concerns and adjust approach if needed
How to initiate: "I'd like to start thinking about what success looks like beyond our initial 90 days. Based on results so far, what would you want to see in an extended engagement?"
Position ongoing value
Focus on: What problems will arise if you leave vs. what opportunities exist if you stay
Example framing: "We've solved the immediate challenges around [original problem]. The next phase would focus on [emerging opportunities] that could deliver [potential value]."
Offer multiple engagement options
Scaled engagement: Increased scope or time commitment Specialized focus: Narrow focus on specific high-value initiatives Transition planning: Help hire and onboard full-time replacement Advisory relationship: Ongoing strategic guidance at reduced commitment
Red flags that indicate problems
Lack of engagement from key stakeholders
Warning signs: Cancelled meetings, minimal responses, avoided conversations
Likely causes: Unclear value proposition, poor relationship building, competing priorities
Actions: Direct conversation about expectations and value, increased relationship investment
Slow adoption of new processes
Warning signs: Team members reverting to old ways, resistance to change
Likely causes: Insufficient involvement in design, inadequate training, cultural misfit
Actions: Increase involvement in solution design, additional training, cultural adaptation
No measurable improvement by day 45
Warning signs: Metrics flat or declining, no visible progress
Likely causes: Wrong problem diagnosis, poor implementation, unrealistic expectations
Actions: Reassess approach, adjust strategy, reset expectations with stakeholders
Exclusion from strategic discussions
Warning signs: Not invited to important meetings, last to know about decisions
Likely causes: Haven't established strategic credibility, focusing too much on tactics
Actions: Demonstrate strategic thinking, request inclusion in planning discussions
Your 90-day success checklist
Week 1:
- [ ] 1:1 meetings with all key stakeholders completed
- [ ] Current state assessment documented
- [ ] Quick win opportunities identified and prioritized
- [ ] 30-60-90 day plan developed and shared
Week 4:
- [ ] 2-3 quick wins implemented and communicated
- [ ] Positive feedback from key stakeholders
- [ ] Core system designs completed with team input
- [ ] 30-day progress report delivered
Week 8:
- [ ] Core systems implemented and operational
- [ ] Team members trained and developing capabilities
- [ ] Measurable progress against SOW objectives
- [ ] Stakeholder satisfaction confirmed
Week 12:
- [ ] Systems optimized and showing strong results
- [ ] Team capable of maintaining improvements
- [ ] Clear ROI demonstrated and documented
- [ ] Renewal conversation initiated
Relationship building:
- [ ] Trust established with key stakeholders
- [ ] Regular communication rhythms working
- [ ] Team members view you as valuable partner
- [ ] Leadership team includes you in strategic discussions
Value demonstration:
- [ ] Quick wins delivered and recognized
- [ ] Core objectives from SOW on track or achieved
- [ ] Measurable business impact documented
- [ ] Positive feedback collected and documented
The compound effect of strong starts
Getting your first 90 days right creates compound benefits:
Immediate benefits:
- Higher likelihood of renewal
- Stronger references for future opportunities
- Increased confidence in your approach
Long-term benefits:
- Refined methodology for future engagements
- Expanded network through satisfied clients
- Enhanced reputation in the market
- Higher rates justified by proven results
The bottom line
Your first 90 days determine whether you become a trusted strategic partner or an expensive disappointment. The difference lies not just in your expertise, but in your ability to rapidly build relationships, deliver value, and adapt to new environments.
Treat every engagement as an opportunity to refine your approach. The most successful fractional leaders develop systematic methods for starting strong, building trust, and delivering value quickly.
Remember: you're not just completing a project – you're building the foundation for long-term client relationships and a sustainable fractional practice.
Next up: Building a sustainable fractional practice. Learn how to create a business that provides the income, flexibility, and fulfillment you're seeking.
