The 90-Day Leadership Reset
Most roofing company owners became leaders by accident. They started a company, hired people, and suddenly had a team looking to them for direction. Nobody taught them how to lead. The skills that built a $3M company don’t automatically scale to $7M or $10M.
A 90-day leadership reset changes the trajectory. Research from the Center for Creative Leadership shows that focused leadership development over 90 days produces measurable behavior change that shorter interventions don’t achieve (CCL, 2023). The time frame is long enough for new habits to form but short enough to maintain focus.
The Leadership Deficit
The typical path from technician to owner creates predictable gaps.
Technical excellence doesn’t transfer. Being the best roofer on your crew doesn’t prepare you for managing a P&L, developing people, or building systems. According to research from the Harvard Business Review, 60% of new managers fail to develop the interpersonal skills their roles require (HBR, 2022).
Day-to-day demands crowd out development. Every hour spent on leadership development feels like an hour not spent on urgent problems. The urgent always wins over the important unless you create structure that protects development time.
Feedback disappears. Nobody tells the owner they’re not leading well. Employees filter their feedback. The isolation of ownership masks leadership deficits until they cause serious damage.
The reset addresses these gaps systematically rather than hoping they resolve themselves.
The 90-Day Framework
The reset divides into three phases, each building on the previous.
Days 1-30: Assessment and Awareness
You can’t improve what you haven’t measured. The first 30 days focus on honest evaluation.
Start with a leadership 360 assessment. Ask 5-8 people, direct reports, peers, customers, and suppliers, to evaluate your leadership across key dimensions. Tools like the Leadership Practices Inventory provide structured frameworks (Kouzes & Posner, 2023). The goal is data, not validation.
Document your current time allocation. Track every hour for two weeks. Where does your time actually go? Most owners discover massive gaps between intended and actual allocation. According to McKinsey research, executives who track time allocation find 20-30% opportunities for reallocation (McKinsey, 2023).
Identify your top three leadership gaps. Based on feedback and time data, what specific capabilities would most improve your effectiveness? Common gaps include: delegation, difficult conversations, strategic thinking, and people development.
Days 31-60: Skill Building
The middle phase focuses on deliberate practice of identified skills.
Choose one primary skill for intensive development. Attempting to improve everything simultaneously improves nothing. Research on skill acquisition shows that focused practice on single skills produces faster improvement than distributed practice across multiple skills (Ericsson, 2022).
Find a model. Identify someone who excels at your target skill. Study their approach. If possible, ask them to mentor you. Leadership development accelerates dramatically with good models.
Practice daily. If your skill gap is delegation, delegate something new every day. If it’s difficult conversations, have one difficult conversation daily. Skill building requires repetition, not just understanding.
Get feedback weekly. Check in with your 360 respondents monthly. Ask specifically about the skill you’re developing. Progress should be visible within 30 days.
Days 61-90: Integration and Habits
The final phase locks in changes and builds sustainable practices.
Systematize your new behaviors. Convert conscious effort into unconscious habit through routine. The delegation that required willpower in week 5 should feel natural by week 12.
Extend to new skills. With your primary skill improving, add a secondary focus. Use the same deliberate practice approach.
Build accountability structures. Find an accountability partner, peer CEO, coach, or advisor, who will check your progress regularly. According to accountability research from the American Society of Training and Development, having an accountability partner increases success probability by 65% (ASTD, 2023).
Plan your next reset. Leadership development isn’t one-and-done. Schedule your next 90-day cycle before completing this one.
Common Obstacles
Predictable challenges derail leadership resets.
The urgent crisis. A major problem demands attention and development activities get postponed. The solution: protect 30 minutes daily as non-negotiable development time. Even during crises, 30 minutes won’t break the business.
Discouraging feedback. Honest assessment reveals uncomfortable truths. The temptation is to dismiss feedback or avoid further assessment. The solution: reframe feedback as information, not judgment. Data enables improvement.
Slow visible progress. Leadership skills develop slowly. You won’t see transformation in week 2. The solution: measure leading indicators (behaviors attempted) not just lagging indicators (results achieved).
Isolation. Without peer support, the reset feels like a solo struggle. The solution: find other owners pursuing similar development. Peer groups like Vistage, EO, or industry associations provide community.
The Leadership Multiplier
Leadership improvement multiplies across the organization.
When you delegate better, your team develops faster. When you have difficult conversations effectively, problems resolve before they metastasize. When you think strategically, the company moves toward better outcomes.
According to leadership research from Gallup, team engagement increases by up to 70% when leadership quality improves (Gallup, 2023). Your development doesn’t just help you, it improves everyone around you.
The roofing company that reaches $10M needs a different leader than the one that reached $3M. The 90-day reset builds that leader deliberately rather than hoping growth happens accidentally.
Start Here:
- Request informal leadership feedback from 3 trusted employees this week
- Track your time allocation for 5 consecutive workdays
- Identify your single biggest leadership gap and commit to 90 days of focused improvement
Sources:
- American Society of Training and Development. (January 2023). Accountability and Goal Achievement Research.
- Center for Creative Leadership. (January 2023). Leadership Development Program Effectiveness Study.
- Ericsson, A. (January 2022). Peak: Secrets from the New Science of Expertise. Updated Edition.
- Gallup. (June 2023). State of the American Manager Report.
- Harvard Business Review. (June 2022). First-Time Manager Development Research.
- Kouzes, J. & Posner, B. (January 2023). The Leadership Challenge. 7th Edition.
- McKinsey & Company. (January 2023). Executive Time Allocation Research.
Leadership development isn’t optional for owners who want to scale beyond their current ceiling. The 90-day reset provides structure that transforms intention into action. The investment is 30 minutes daily for 90 days. The return is a leadership capacity that multiplies everything else you do.