- Leandro Herrero - https://leandroherrero.com -

Three magic questions for leaders

Daily Thought taken from my new book Camino – Leadership Notes On The Road.

Read preview extracts: Camino – Extract Chapter 1 part 2 [1] and Extract Camino Chapter 1 [2]


1. Will I regret not doing this? Bezos, Amazon chief. Here from an article published a few years ago: ‘When faced with significant and tough decisions, Bezos is known for touting this framework as a way to help his decision making. When a big decision or idea presents itself to him, he thinks forward in time to when he is age 80.  He asks “Will I regret not doing this?”  His goal in life is to minimise the number of regrets, so his decisions are guided by that principle.  If 80-year-old Bezos will regret not doing it, then he will move forward with the idea.  He would much rather try something, even if he will fail, then not try it and regret it later’.

2. If not now, when? Hillel the Elder [3], rabbi, died in 10 AD. Actually, you get here three questions for the price of one. Personally, I must confess they have influenced me more than perhaps I have cared to acknowledge (although featured in many of my books and writing).

‘If I am not for myself, who will be for me?
But if I am only for myself, who am I?
If not now, when?’

(Ethics of the Fathers, 1:14)

3. What will I tell the children? Me. If we can’t answer this satisfactorily, I think we should be very restless. For me, it’s not what I will  tell my business partners, my clients, my bank manager, my friends, my social group, my political party (I don’t have one) my tribe, my readers, my followers. #itsthechildrenstupid. My children. Their children. Your children. The next and next and next generations. It’s legacy. But it does not have to be with a big L. It just needs to pass the test though: will I get a red face? Smiling face? What face?

3 questions. That’s it.


Camino – Leadership Notes On The Road 

Preview extracts:

Camino – Extract Chapter 1 part 2 [1]

Extract Camino Chapter 1 [2]


A collection of notes on leadership, initially written as Daily Thoughts. Camino, the Spanish for road, or way, reflects on leadership as a praxis that continuously evolves. Nobody is ever a leader. Becoming one is the real quest. But we never reach the destination. Our character is constantly shaped by places and journeys, encounters and experiences. The only real theory of leadership is travelling. The only footprints, our actions. The only test, what we leave behind.


To be notified as soon as pre-orders go live – email us at:

uk-office@thechalfontproject.com [4]


Dr Leandro Herrero is the CEO and Chief Organization Architect of The Chalfont Project [5], an international firm of organizational architects. He is the pioneer of Viral ChangeTM, a people Mobilizing Platform, a methodology that delivers large scale behavioural and cultural change in organizations, which creates lasting capacity for changeability.
Dr Herrero is also an Executive Fellow at the Centre for the Future of Organization, Drucker School of Management. An international speaker, Dr Herrero is available for virtual speaking engagements [6] and can be reached at: The Chalfont Project [7] or email: uk-office@thechalfontproject.com. [8]