“The first responsibility of a leader is to define reality. The last is to say thank you. In between, the leader is a servant.” — Max De Pree
I’ve noticed many leaders (across for-profit and nonprofit organizations) frustrated because they are leading the organization they used to have, not the one they have now.
They blame their team.
They blame their board.
They blame their customers.
And quite often, they blame themselves.
Often, the issue isn’t effort (not more hours in a day!), it’s courage and awareness. They haven’t fully come to grips with the season their organization is in.
Defining reality is the first job of a leader.
Too often, leaders operate and lead the organization they used to have, or at times, the one they fantasize about, not the one they are in today.
The chart below outlines the four most common organizational life stages. Use this as a simple diagnostic to help determine what you should focus on.
| 1. Startup | 2. Growth | 3. Mature | 4. Exit / Renewal | |
| Goal | Survival & Validation | Market Penetration | Profitability & Stability | Liquidity or Rebirth |
| Key Reflective Question | Is there a need for the product / service? | Can this scale without breaking? | Where are we becoming complacent or comfortable? | If we started this today with a blank slate, would we build this? |
| Focus | Validate real customer need through rapid testing Conserve cash and extend runway Build a small, adaptable, high-ownership team | Build a repeatable, scalable revenue engine Strengthen systems, processes, and culture Hire intentionally to support sustainable growth | Optimize efficiency and improve margins Develop leaders and deepen bench strength Eliminate complacency through continuous improvement | Clarify strategic path (exit, reinvest, or reinvent) Maximize enterprise value and organizational health Prepare for leadership transition or bold reinvention |
| Blindspot | Denial – Falling in love with the idea instead of facing market reality | Control – Trying to scale while holding on too tightly to control | Comfort – Getting comfortable and mistaking stability for security | Attachment – Holding on too long or choosing short-term wins over long-term legacy |
| Symptoms | Constant pivoting without clear evidence of traction High effort and activity, but little to no paying customers | Teams feel stretched and communication starts breaking down Inconsistent customer experience as demand increases | Slower decision-making and increased bureaucracy Innovation stalls while legacy processes dominate | Mission drift Leadership hesitation or misalignment on the future direction Loss of energy, ownership, or clarity across the organization |
Flourishing organizations don’t just happen by accident.
They are the result of leaders who have the courage to define reality and respond to it.
Being a founder and leader is not easy. I get it. You’re in it every day. Pushing, Solving, Grinding. At times it feels like one step forward, two steps back. And when you’re that close to something you care deeply about, objectivity is hard. That simply makes you human.
Take a moment to reflect on where you are. And if an outside, objective perspective would be helpful, we would be honored to serve you.
[If you found this helpful, I’d encourage you to forward it to a leader who could benefit from it.]
