Living fully in whatever season you are in is so important and relevant that I want to give examples of what happens when you don’t recognize that your season has changed. These real-life examples come from executives I’ve coached over the years. Each highlights the risks of failing to adapt and the benefits of recognizing and aligning with the current season. There are several examples; see which might pertain to you.
1. The Startup CEO Who Won’t Let Go
Old Season: Building the company from scratch, wearing all the hats, making every decision, and working 12–14 hours a day.
New Season: The company is now profitable with a solid leadership team, and the CEO’s role should shift to strategy, vision, and empowering others.
Issue: The CEO continues micromanaging, staying involved in every decision, and working as if the company will collapse without them. This stifles leadership development and leads to burnout.
Solution: Step back, delegate operational decisions, and focus on long-term growth and mentorship.
2. The Sales Leader Turned CEO
Old Season: As a top-performing sales executive, their focus was solely on closing deals and building relationships with clients.
New Season: Now the CEO, their role requires strategic oversight, organizational leadership, and financial acumen.
Issue: They remain hyper-focused on sales metrics and client relationships, neglecting the broader demands of managing the company. This leaves critical areas like operations, HR, and company culture underdeveloped.
Solution: Shift focus to developing a balanced leadership approach, trusting other leaders to manage sales while addressing company-wide priorities.
3. The Founder Who Won’t Transition to Retirement
Old Season: The passionate founder grew the company over decades and has always been deeply involved in every aspect of the business.
New Season: It’s time to transition leadership to a successor and focus on legacy, mentoring, or personal pursuits.
Issue: The founder can’t let go, undermining the new leadership by remaining too involved and causing confusion within the organization.
Solution: Define clear boundaries, step into an advisory role, and trust the next generation to lead.
4. The Early Career Hustler Turned Established Leader
Old Season: In the early career phase, they said “yes” to every opportunity, worked tirelessly to prove themselves, and took on projects beyond their role.
New Season: Now they’re in an established leadership position where their value lies in prioritization, strategic thinking, and coaching others.
Issue: They continue overcommitting, working late hours, and doing tasks better suited for junior staff, resulting in inefficiency and frustration within the team.
Solution: Focus on empowering the team, setting boundaries, and aligning efforts with organizational goals.
5. The Family-Focused Executive Who Overcorrected
Old Season: A workaholic phase in which their career took priority over everything else—including family and health.
New Season: After realizing the toll on personal relationships, they want to spend more time with family and focus on personal well-being.
Issue: They struggle to balance the demands of their executive role, overcompensating by stepping back too far and leaving their team without clear guidance or leadership.
Solution: Build intentional boundaries between work and personal life, ensuring both priorities are addressed without sacrificing leadership effectiveness.
6. The Growth-Phase Executive Who Avoids Transformation
Old Season: Leading a company in rapid growth, focused on scaling fast, and taking risks to secure market share.
New Season: The company is mature, requiring careful risk management, process optimization, and steady performance to maintain stability.
Issue: The executive continues to push for aggressive growth tactics, creating unnecessary volatility and risking the company’s hard-earned stability.
Solution: Shift focus to sustainability, operational efficiency, and long-term planning rather than constant expansion.
7. The Mid-Career Professional on Autopilot
Old Season: A highly motivated phase where they were learning, growing, and taking on leadership roles with enthusiasm.
New Season: Now in a mid-career plateau where they have experience but lack the same drive or clarity of purpose.
Issue: They continue going through the motions, avoiding self-reflection and the opportunities to learn new skills, and failing to address the lack of fulfillment or alignment with their role.
Solution: Take time for professional development, re-evaluate career goals, and align work with personal values.
8. The Acquirer Stuck in Integration Mode
Old Season: Driving mergers and acquisitions, focused on deal-making, and rapidly integrating teams and processes.
New Season: The acquisitions are complete, and the focus should shift to nurturing the company culture and consolidating gains.
Issue: The executive remains transaction-oriented, failing to invest in long-term integration, culture-building, and employee engagement.
Solution: Transition to a phase of stability, focusing on people and process alignment to ensure sustainable success.
9. The Early-Stage Leader in a Mature Industry
Old Season: A risk-taker and innovator, thriving in industries that reward disruption and quick wins.
New Season: Now leading in a mature or regulated industry, where success requires patience, consistency, and adherence to processes.
Issue: They continue taking risks without fully understanding the industry’s complexities, jeopardizing credibility and long-term success.
Solution: Slow down, learn the nuances of the industry, and adopt a more methodical leadership style.
These examples illustrate the importance of recognizing when seasons have changed and adapting leadership habits accordingly. I challenge you to understand your current season and ask yourself if you are navigating it as adeptly as possible. Are you hanging onto outdated habits and mindsets? Move forward with purpose in your current season and get ready for the next one.
In the next, and final, installment of this life seasons series, we’ll focus on aligning your goals with your current life season. I’ll offer some practical ways to better navigate the season you are in and set yourself up for success in the next one.
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