List of Coaching Questions

September 15, 2019

“How are you complicity in creating the conditions that you say you don’t want?” - Jerry Collona

I like this question because it forces you to look inwards rather than outwards on why something might be the way it is.

“Let’s flash forward to a week or month from this <event?. What would make this a home run for you? What does “successful” look like? - Tim Ferris

This question forces you to think about the outcomes that you’d like to achieve, the accolades you’d like to receive, the impact that you desire to have. It’s a good goal-setting question.

What conventional wisdom was shunned for this to be successful?

Conventional wisdom suggests to look for patterns and come up with playbooks to replicate what was successful. Success is often a matter of chance and timing, and even success cases would have failed if it weren’t for that. Better questions are what was tried, why or why it didn’t work? Everyone’s path to success will be different, and a playbook by definition is something that has already been played.

What is the crazy idea you’re currently working on that will result in a breakthrough? If it’s not a crazy idea, then it’s not a breakthrough but an incremental improvement. - Peter Diamandis

This form of a question can take the thinking from small to big. Framing a crazy idea as a difference between incremental improvements and breakthrough can lead to introspection on where we’re thinking big in the organization.

How are you trying to disrupt yourself? If you don’t disrupt yourself, someone will disrupt you. - Peter Diamandis

The goal of this question is to make them think about how they have an opportunity to decide their own company’s future before someone else does. If they have the power to assemble people to disrupt them, they should do it. Or accept the status quo as an ideal state.

Are you thinking 10% improvement or 10x improvement? - Peter Diamandis

Framing 10% as something everyone is doing will make them try to separate themselves from “everyone”. Given that x10 doesn’t cost ten times the cash should make them consider going for something bigger than just incremental improvements.

Are you having a breakdown or a breakthrough?

This can make a person see their experience through a much different perspective. It can get them to see what actions they need to take to take advantage of the current experience. What is the worst thing that can happen if I stopped doing what I’m doing? And how long would it take for me to undo that.

This can help change course by making someone realize the risks of change aren’t as big as they may think. And in the event that things don’t work out due to the change, reverting is a realistic, if not easy, step.

What do you understand about yourself and your goals that the other person isn’t understanding?

This question forces the person to articulate a difference in understanding of a goal between two people. We often don’t understand ourselves and even if we do, it is difficult to communicate about ourselves to other people.

Are you constructing fragility or enabling bravery?

When someone is “helicopter parenting” someone they are instilling a sense of fear and doubt into the person, while thinking that they are helping them and preparing them for a difficult situation. By contrast, active encouragement can instill confidence and give them the runway to be brave and take on challenges. The mentor in a relationship must know where they are treading.

Finish this sentence, Chris. Everyone says Chris is great, but…

This question puts a person in a position of having to articulate what other people’s perception of them is. Vocalizing this and reflecting deeper on this view can give them an insight into how their behaviour is impacting people. We can also use, “I would hire Chris except for…”. It forces them to think about what people don’t like about them.

Is your heart into this?

At the beginning of a task it is often not a question of ability but a question of inspiration. Starting small and doing one simple thing to get your heart into whatever you are doing is critical. Once that flow is rolling, the head can organize the outputs of the heart. At the beginning, it is not an intellectual activity but one of volition.

What is keeping this relationship from forming?

Humans have a built-in bias towards not making friends or forming new relationships. Avoiding an enemy is considered more important than making a friend. The cost of mistaking someone for a friend when they are an enemy is perceived to be much higher than mistaking someone for an enemy and them turning out to be a friend (source). Perhaps the recognition of this will help form the relationship.

Do you want to be admired?

It is normal to have a “perception gap” where what people think of you is different than what you think of yourself. We may not be as confident or smart as others may think we are, and when we are admired, it is normal to consider this form of impostor syndrome. These feelings can drive a gap between yourself and someone else as the focus becomes maintaining the persona, and not revealing yourself to have these gaps. This drives a wedge in getting to know someone as we’re managing the perceived gap, and not focused on the true relationship.

Does this problem require an administrative or structural solution?

There is a natural inclination to solve issues as they come up, and often the solutions being applied are administrative, e.g., adding a process, documenting something. If the underlying problem is structural, an administrative solution is unlikely to address the issue.