The Coaching Habit

This post is inspired by a book I recently read, titled “The Coaching Habit” by Michael B. Stanier, and how it applied to my everyday life. It’s available on Amazon Kindle for $7.95.

Do you run into situations where it seems like someone just won’t listen to you? No? I’m happy for you! Yeah? Welcome to my world (and the rest of us). In the context of teamwork, I used to experience this frustrating feeling a lot. It used to make me feel misunderstood, ignored, unappreciated, etc. I would do everything to get rid of it. “Why don’t they just listen to me!”, I used to wonder. “We’d all be so much better off if you listened.”, I used to say. The irony is, it was me who needed to listen more carefully.

Enter this book on coaching. What is coaching?

Coaching is an act of asking questions, in order to navigate the discussion and learn more about the person across the table. It pairs well with active listening. Active listening means you aren’t there just to nod and mumble. It’s asking a lot of probing questions that will guide the other person to tell you everything you both need to know.

Communication is about establishing a link for exchanging information between two parties. What happens when you are not on the same page with someone? What I would do, usually, is double down on my own theories, and make the gap even wider. What would you do instead? I’ve arrived at a conclusion that in such situations I need to forget about my own agenda and focus entirely on understanding the other person. It takes serious willingness and commitment to do just that, but it will take you a long way.

Seven Chapters / Questions

So that being said, this book came quite handy to learning how to coach better, how to ask better questions to understand what the other person is saying. They are geared towards people who are coaching others, such as a manager-report or mentor-mentee situations. However, I found it quite applicable in other situations as well, including my own perils and frustrations with not being heard during team oriented debates. The book is organized in seven short chapters, each explaining how that question comes into play.

So, here they are, in order of appearance, what they mean in the context of coaching and how they applied in my own context of teamwork:

1. What’s on your mind?

The opening question. The author recommends asking this question to open up the discussion.

In the context of coaching in 1-1 sessions, the author describes two different situations. One is coaching for performance, which is the everyday, urgent matters of work. The other one is coaching for development, a more important, long term discussion that needs to happen in such a relationship.

In my own context, this is also a good question to stop myself from talking and let the other person express their point of view, uninterrupted.

2. What else?

The expansion. Author recommends following up with this question to get closer to the bottom line.

Most of us won’t immediately say what really bothers us or where we’re stuck at. This question can help get to it faster. It will help you skip over the mundane things and get to the important stuff.

Feel free to ask the question multiple times… and what else?

In my own context, this helps me get the most of the disagreement out in the open and laid out in front of me to understand.

3. What’s the real challenge here for you?

The Focusing question.

Once you’ve identified what’s really on the other person’s mind, asking this question will help you understand why it’s on their mind. Or what part of it is bothering them.

Feel free to ask the question multiple times here as well… what else is a real challenge for you?

In my own context, this question helps me get to the point of the disagreement. What’s at the core of the problem. Usually there will be one point of disagreement, where perhaps I made a mistake in my own thinking, which caused all the other points of disagreements. Asking this question and identifying that point together can help us both reach an agreement, by changing either of our opinions. Personally, I care only that we do the right thing, I don’t care who’s ideas win.

Stick to “what”

The author strongly recommends not drilling down on people with “whys”. They put people on the defensive side. They feel attacked. There’s a place for this question, coaching is not one of them. Besides, do you really need to have the backstory? Stick to “what”.

4. What do you want?

Author says there is a big difference between wants (tactical) and needs (core). We are more likely to talk about the wants, that get our needs satisfied, without directly revealing what our needs are. Your job as a coach is to understand the need behind the want. It will help you get the other person what they need, sometimes even without giving them what they want.

In my own context, I like to ask this question as “what is it that we want?”, as we’re working as a team on the same problem. If we’re coming to this discussion with opposite wants (I want it good enough and simple vs I want it great and elaborate), then perhaps that’s the real discussion we need to have first. Here I find it useful to acknowledge both our ideas are good in their own respective contexts, and that we’ve made progress towards a unanimous decision.

5. How can I help?

Great question that will help identify if the other person needs something from you. Author recommends guiding the other person to solve the problem for themselves, by asking more questions.

6. If I’m saying yes to this, what am I saying no to? Strategic question.

The author mentions five other strategic questions that should be considered before you jump into lending a hand to someone and spending your time on something that might distract you from something more important.

7. What was most useful for you? Repetition is the mother of learning.

Finally, at the end of each session and beginning of next one, author recommends reflecting on the past discussion as a way to hack your brain into remembering it better. Apparently, when we recollect our thoughts, our brain is more likely to put them in a long-term memory, and they are less likely to disappear. Therefore this blog post. Yup.

Introspection via the “Who am I” document

At any point in time during your career, the bottleneck to your growth and development can be a lack of insight and self-awareness of who you are and what makes you perform the best. Read more to learn about the process of introspection using the “Who am I” document.

Who am I

To start with, this is something I learned while working with my self-awareness mentor. Dear L.C. taught me this great format for introspection, a “living document” that you should be constantly reviewing, getting feedback on and so on. Down below there is an excerpt from my “Who am I” document and how to write it.

How to write it?

You write this document bottom up. Start with your workflow, something that’s easiest to observe. Write down how you wake up, how much you work, when do you eat, who do you hang out with and so on. Whatever is relevant for you.

When you fill out that section, move one section up. Write that one in, using the insight you’ve gained from your previous section. Remember – it’s actually good if it sounds repetitive and obvious. There should be a strong causality and correlation between all sections. Otherwise you might be lying to yourself (not necessarily, but, you could be).

So, Who am I?

Here it is – the outline for this document and some examples of what you could write in for your document.

1. My purpose

This is the top section, the one you will write the very last, after many iterations on your doc. Feel free to keep it empty for some time. The purpose will eventually reveal itself.

To be a super awesome technical leader at solving hard problems, while inspiring people around me.

2. My core beliefs

A core belief is one that’s like a constant in your world. Something you can’t part with so easily. It defines who you are, what else you believe in, what you care about the most, who you want to become and much more. They are not always perfect and healthiest for you, so have compassion for yourself.

Productivity: I have to be productive to feel happy with myself.

Challenge: I have to be challenged to feel like I’m doing something that matters.

Social: I am a social creature and I can’t live without having great social interactions.

3. My leadership values

How do your beliefs and values translate to your work environment? Each great company nowadays has a strong culture and a set of leadership values that you can and do identify with. Find what resonates with you.

Deliver Results: Leaders deliver results in timely fashion.

Dive Deep: Leaders go to the heart of the problem. No task is beneath them.

Learn and be Curious: Leaders are constantly working on improving themselves.

Earn Trust: Leaders treat others respectfully.

4. My strengths

Strengths and weaknesses stem from your previous sections. They are like psychological archetypes – double edged swords, two sides of the same coin.

Fast: My speed of execution is amazing. Once I get an idea of how to solve a challenging problem, there is no stopping me.

Technical knowledge: I have what it takes to solve hard problems and I’m not afraid to learn new things.

Unselfish: I’m always happy to share my knowledge and help others succeed.

5. My weaknesses

Here I write not just what my weaknesses are, but what do I have to do in order to compensate for them.

Rushy: I can sometimes rush too hard to get a problem out of the way, making others around me feel uncomfortable about the associated risks. I have to make sure people have their concerns addressed properly first.

Trust: Since I love problem solving so much, sometimes I can have issues with trusting other people with work – delegation – will they do a good job at it? Therefore, I have to let go more often than I would instinctively, but perhaps offer my help in reviewing the work or mentorship in case they get stuck.

Gullible: I will go out of my way to help others and sometimes that makes me vulnerable to exploitation. I have to ask probing questions to defend from this.

6. My passions

What gives you butterflies? What is that thing you love to do, that others might call just work, but you experience as enjoyment?

Excellence: I’m passionate about being excellent – especially in the software development world and in my hobbies. This makes it possible to be fast and solve challenging problems.

Psychology: My favorite hobby is learning and practicing good mental hygiene.

Learning and teaching: I love learning new things and then sharing my knowledge, especially in areas such as music, psychology, leadership and computer science.

7. My operating principles

Principles stem from values. This is how you prefer to do your job. For example, if you value integrity, your principle might be “Do everything by the law” and such.

Move fast: I like to execute fast. I love competing with myself. Also, done is better than perfect.

Kaizen: I continuously learn new things and improve my existing self by examining my past work and mistakes.

Soft-skills: I pay attention to how I treat others around me and how I can make it a comfortable experience.

8. My values

Values are things you hold dear to your heart. If someone were to negotiate a work environment with you, these are the things that would be the hardest to compromise on.

Speed: I don’t like when things move slow, hence I’ll do whatever is reasonable to speed them up.

Growth: Learning is very important to me, from the earliest stages of my life. Knowledge is happiness.

People: I treasure people around me and our relationships, and I can’t do work in a way that might bring them harm.

9. My workflow

Start with this section. Describe what does your day look like.

Productivity bursts: I don’t do a lot throughout the whole day, but every day I find some time to sit down, get in the zone and do some amazingly productive work.

Learner and teacher: I look for opportunities to help others and to learn something new, every day.

Socialize: Colleagues and friends? Yes please. Let’s have a beer buddy. I love to take a break with my peeps at work and talk about the non-work related stuff.

Iterating on the document

When you start writing this document, you embark on a journey. You won’t get it “right” from the start. It will never be “done”. Keep going up and down the document. As you start moving bottom up, you will occasionally see that something you wrote in your bottom section, say “workflow” for example, is not so crucial as you thought. Sometimes you will discover something in the middle, say a “leadership value” you care about, and you will see that it’s actually not reflected in any way with your values. So you think a bit about those and edit one or the other (or both) to make them “sync” with each other. Remember, the journey is more important than the destination.

Reviewing the document

Once you are happy with your doc, find a good friend of yours who knows you better than you know yourself, and ask them to read your doc. Ask for their opinion. Does it sound like you? Would they add or change anything?

Keep it alive

Review the doc from time to time (once a quarter or a year) and tweak it. We all change with time, after all.


Thank you for taking your valuable time to read my article! I hope you will find this exercise as exciting, revealing and rewarding as I have. And thanks to my awesome mentor L.C. for sharing this with me and allowing me to share it with you.

Four Communication Types

During my career in the Silicon Valley, I’ve mentored and coached dozens of people, without ever having a formal training on it. Last year, I attended the Berkeley High Impact Leadership course and I finally learned a good theoretical background behind these processes. In this article, I will be sharing the secret recipe with you!

After reading, you should know more about how to express empathy in your relationships, as well as the basics of playing the four basic role archetypes.


First of all, I’d like to emphasize the importance of empathy in your work relationships. What is empathy? The best explanation I’ve heard over the years is that it basically means to be able to walk in other person’s shoes. To imagine you were them. How would you feel?

For those that like an instruction manual to everything, like myself, here’s a quick trick. There are two types of empathy according to the cognitive psychologist Dr David Burns: thought and feeling empathy.

Thought empathy is simply the act of summarizing what you’ve heard from the other person.

Feeling empathy is simply the act of noticing how the other person is probably feeling and letting them know you are aware of their emotions.

So let’s take an example. Say your coworker Bob comes to you with a following problem:

Bob: That meeting went horribly. We’re two months behind on our schedule and our director demands we meet the deadline, which is only four months ahead of us! I don’t know what to do!

You: Sounds like you are behind on your project (thought empathy). You must be under a lot of stress (feeling empathy).

Bob: etc.

This conversation pattern can occur for as long as Bob needs to talk with you. Pay attention to Bob’s words and body language, they will make empathizing with him that much simpler.

Support Role

What we’ve seen above is also called the support role. When you choose to play a support role in your work relationship, your job is to simply empathize with your coworker and simply make them feel heard. Is this useful? Oftentimes, this is exactly what people need, especially when under a lot of stress. Giving premature advice or asking too many questions might do more harm than good.

The main quality of the support role is that it’s full of empathy, but not much on telling the other person what to do, nor asking a lot about it. Let’s put those two on a graph:

Fig. 1) Support has “low tell” and “low ask”.

Who to support: Ask yourself – do I know this person well enough? If the answer is no, probably the best course of action is the support role.

Coaching Role

So what do we call it when you start asking questions, inquiring? For example:

Bob: That meeting went horribly. We’re two months behind on our schedule and our director demands we meet the deadline, which is only four months ahead of us! I don’t know what to do!

You: Sounds like you are behind on your project (thought empathy). You must be under a lot of stress (feeling empathy). What do you plan to do about it (inquiry)?

Bob: etc.

That’s coaching in a nutshell. The main pattern is:

  1. Listen: pay attention to what the other person is saying and what does their body language reveal.
  2. Empathize: show that you’ve heard the other person by empathizing with them using thought and/or feeling empathy.
  3. Ask: using open-ended questions, help the other person think about the problem they are having and help them reach the solution on their own!
  4. Go to step 1.

Most importantly, when coaching, do not ask suggestive questions. Then you aren’t a coach. Ask open-ended questions. Questions that cannot be answered by “yes” or “no” and such. Instead of asking “are you going to do X about it”, ask “what are you doing to do about it”. Let the other person think about the solution, your job as a coach is to guide them in their thinking. Keep them on track.

Not having to give any advice, coaching is very useful when you feel that the other person is far more capable of solving the problem for themselves than you are.

Fig. 2) Coach has “low tell” and “high ask”.

Whom to coach: Ask yourself, do I believe this person can resolve the problem at their own? If yes, assume the coach role.

Advisory Role

Let’s take an opposite example. What happens when you know more about the problem your colleague or friend is having and you want to “jump right into it” and help them succeed? In this case, you are playing the role of an adviser. You aren’t asking many questions, but you do tell a lot. Make sure you are invited and welcome to play this role, before you do. Playing an adviser is a dangerous one!

Fig. 3) Adviser has “high tell” and “low ask”.

Whom to advise: This one is best to do when you are directly asked for an advice, such as when being a consultant. Otherwise, ask yourself, did this person ask for my advice?

Mentor Role

Finally, being the mentor is my favorite relationship type. In this role, you are going to ask questions and give advice, you will empathize, support, coach and advise, all at the same time.

Fig. 4) Mentor has “high tell” and “high ask”.

Whom to mentor: Does this person need both coaching and advising? See above. Make sure the person wants to be mentored.

The other side of the archetypes

Finally, when playing all of these roles, you have to pay attention to how your participation is received on the other end. Just knowing these “recipes” won’t make you the best coach or mentor in the world, right? Trying to be a supportive person can render you seem absent or useless. Being too much of a mentor can make you seem like a micro-manager, and so on. So here’s an example of what could happen if things go wrong:

Fig. 5) The negative sides of the four communication roles: Micro-Manager, Dictator, Absent and Nuisance.


Alright, hope you had a fun time reading the article. Remember – listen, repeat, then ask for more or give advice if you have a good one. Remember to use open-ended questions. Choose the right role for the situation. Be mindful – focus on the other person, forget about yourself.

Thanks for reading thus far and see you next week.