It has never been a conscious decision for me to become an entrepreneur. It is my passion for coaching that led me to head up a consultancy and then launch a tech start up. Leading two businesses is a daily brain gymnastic and a regular fight with self-doubt. As an entrepreneur, I am questioning every day whether I am making the right decisions about product, people, and processes.

Whether you are an entrepreneur or a leader, making decisions is incumbent to the role and it is often the quality of your decisions that will determine your success. There is something fundamentally contradictory in this though. As a modern leader, you need to be agile and inclusive in the directions you set, always open to others’ ideas and perspectives. And yet, you need to have the conviction and the strength of character to believe in your vision so that it is bold, compelling, and inspiring.

My experience is that finding the right balance between the two is the definition of great leadership. But it can send you slightly mad. In my leadership of Serendis and MentorKey, I draw upon my early teachings in executive coaching to be my best as a leader. There are three lessons that I use regularly to help me find my north star when in doubt. I hope you find these lessons helpful in your own leadership journey.


Coaching lesson #1 – The baby picture (or a reminder of empathy)

It was March 2004 and I had just left Investment Banking to study positive psychology and executive coaching. I had high expectations of the course I had selected and was still adjusting to normal life after Banking in the 90s. The first lesson featured a baby picture on the screen for 2 hours and despite my initial reaction (cynicism and severe doubts about the credibility of the curriculum I had chosen), it had a lasting impact on me.

The baby illustrated ‘empathy’. ‘No matter how wrong or reprehensible you might find your stakeholder, you must find the angles that make them likeable,’ said our professor. ‘Everyone loves a baby, think about your stakeholder as a baby’.

When asked about the most successful leadership characteristic of a 21st century leader, Satya Nadella, CEO of Microsoft also refers to empathy. The capacity to overcome your personal judgement and deeply understand others’ perspectives provides a leader that agility required to innovate. It means, putting ourselves in other people’s shoes and seeing the world through their experience as opposed to ours.

In my role today, the baby picture is a powerful reminder to exercise empathy when I develop new products or lead the team. I try and put myself in other people’s shoes and I ask myself: What are they going through in their life? What is important to them? What do they need? How will they react to this? How can we help them? What am I not seeing? This always prompts different viewpoints for me to adjust our products and approach.


Coaching lesson #2 – Foul Play (are your beliefs limiting you?)

A few years ago, as I was contemplating growing MentorKey as a tech start-up, I shared my hesitations with my personal coach. She is brilliant and naturally, she was asking me to dig deep into my personal beliefs as a leader. At one point, I shared: ‘I don’t know if I have the capability to do this’…her response was so surprising and uncharacteristic of her soft and caring nature. She started shouting: ‘FOUL PLAY FOUL PLAY’.

What I had just shared was a fixed mindset statement, and she helped me to see that it was a judgement on myself that was unhelpful. She explained that it is helpful to critically assess how we have performed and how we might learn to be better, but it is ‘foul play’ to doubt our own capabilities with no grounds to do so.

Since then, I still hear the shouting in my head whenever I doubt my future capabilities. As a tech entrepreneur, there is a firehose of things I discover today and wish I knew yesterday. But I make sure I am constantly learning and growing from my mistakes. How fast I can learn tomorrow, matters more than how much I know today.


Coaching lesson #3 – Three-quarter of a second ahead…no more, no less

In my early supervision groups as a coach, our supervisor taught us the power of questions. ‘Ask don’t tell’ is a core mantra in coaching. When you help your coachee find the answers themselves, they are twice more likely to take action than when you tell them what to do. But to ask the right question, you have to have an angle, an intuition or a judgement on what their next action should be.

Three-quarter of a second means that you need to have a vision for where you are taking the conversation, but you have to be prepared to listen deeply, be surprised and change course as a result of what you hear. In other words, you need to lead the witness but not too much so that you can adjust direction based on what you are hearing.

I use this analogy a lot in my decision-making process and particularly when leading a team. My team want to hear the vision from me. They want to be inspired and clear about where we are going but I also need to listen and be prepared to change my views every time that’s needed. And I need to create the space for the team to do this so that we craft the course together and make the best possible decisions.


The genesis of MentorKey

I hope these 3 lessons will have provided some guidance for you too as you navigate your path as a leader or an entrepreneur. The main challenge, of course, is to bring the theory to practice in our busy lives, and to remember these concepts in our day-to-day interactions with our team members. These need to be conscious and deliberate as bad habits and unconscious snap judgments often take us away from these principles.

This is why I have created MentorKey: to bring these powerful lessons to workplace mentoring and coaching conversations. With our real-time and bespoke ‘Keys’, our mentees are nudged to unpack their challenge and be prepared to address the real issue in their mentoring conversation. And mentors are guided with the right approach and coaching technique to add true impact and help their mentee to progress.

As a result, they ask powerful questions, they are three quarters of a second ahead of their mentee, they dig deeper to unveil their personal helpful or unhelpful beliefs, and together, they practice empathy to broaden their perspective.