Four Steps to Powerful Coaching Conversations

Jonah Larkin

What passes for “coaching” at work are often simply critical opinions couched as “feedback.”

If you’re managing people this is not only ineffective, but runs the risk of alienating the very people (your direct reports) who are there to support you.

Fortunately, if you follow some simple guidelines, it can be relatively straightforward to have powerful coaching conversations that get the best out of your team.

I first started managing people at 22 years old and boy was I bad at it!

Since then I’ve coached some incredibly high performers from Air Force fighter pilots, to Olympians to numerous C-level leaders.

There are 3 key principles that I’ve distilled from all the mistakes I’ve made.

These simple guidelines will allow you to create powerful conversation after powerful conversation.


Asking for permission creates safety and builds trust.

That way the person being coached becomes a willing participant.  

We’ve all been on the receiving side of someone “giving us some good advice.”  

I don’t know about you but there’s always a smarmy part of me that makes me want to punch the person in their arrogant face when I get offered “advice.”

I know…weird, right?  lol.

The point is, don’t be that person.

Seeking permission looks like this:  

“How would you feel if we had a conversation about this?”

“Would it be okay with you if I asked you a question about that?”

“Are you open to how that statement landed with me?”

“If the outcome of this conversation was extraordinary, what would that look like for you?

It works and in fact is essential in sales and could look like this:

“Would it be helpful to tell you about the benefits working together?”


Setting expectations about the goal of the conversation not only builds trust, but allows the coachee to think big within safe constraints.

I like to set expectations about the time a conversation may take, the goal of the conversation and how we’re going to interact.

“Let’s block off an hour for this conversation. The goal is for you to get clarity and inspiration for your next steps. Is there anything else we should add?”

“Mandy I’m going to be completely honest with you and hide nothing. Can we both agree that we’re going to be honest with each other even if might be difficult?

“The goal of this conversation is for you to give me feedback as to how I can help you be a more effective IC (individual contributor).”

“Do you have anything you’d like to add to the agenda?”

Many people are intimidated by their bosses even if they don’t outwardly show it.

When you ask one of your reports to have a conversation with you they may have no idea why and might even be a little bit scared so setting expectations up front can help to put them at ease.


When you’re a domain expert whether it’s in digital marketing or youth soccer, there are general truths and best practices that may be foremost in your mind.

This type of expertise can cause you to make assumptions that can overshadow essential truths.

We see this sort of thing happen when businesses do things like embark on incredibly ineffective initiatives, all because some very basic assumptions were never questioned.

The classic example of this is when Coca-Cola in 1985 introduced “new coke” as their soft drink formula because consumers overwhelmingly preferred the sweeter flavor in taste tests.

However, the taste tests didn’t take into consideration that people may prefer a sip or two of a sweeter beverage, but when they’re drinking an entire bottle they preferred the original formula.

“New Coke” coke was a giant disaster and the original formula was reintroduced within three months.

This means when you’re coaching someone, the more you think you know, oftentimes the less both parties will get out of the conversation.

Instead ask all the dumb questions.

Let go of your agenda.

Coaching is not about you.

It’s about the person sitting across from you.

Really listen to understand.

An easy hack to make sure you understand someone is to repeat back what you think you are hearing.

“So what I hear you saying is that when you bring up problems to the product marketing team you often feel like they’re not really listening to what you’re saying.  Do I have that right?”

Once you make sure you understand what someone is saying, don’t give unsolicited advice.

If the person is curious they’ll ask you.

If you do feel the need to intervene then introduce your advice as a question which is another version of asking for permission, the first principle.

“Would you like to explore how you might create a better relationship with product marketing?

It can be super tempting to chime in and offer advice or to fill the space, but often the most impactful thing you can do is to just be quiet.  

It’s in the silence where the most magnificent insights and magic happens.

So you’ll want to prioritize space and silence over dialogue.


People want to feel safe and safety is created by trust.  

Trust is created by consistent behavior showing the other person you have their best interests in mind.

That’s why asking and moving forward with permission is the first principle of powerful conversations.

Once you’ve established a level of safety you can start to get the best out of your coachee.

Big, powerful questions can help to get people out of their heads and into their inner sense of strength and wisdom.

Strong questions get people thinking, and create the opportunity for the coached person to come up with solutions themselves

Examples of powerful questions are:

“What do you think you should do next?”

“If you could change anything what would you change?”

“Instead of thinking about what’s possible, what might you do if couldn’t fail?”

“What would make this conversation absolutely extraordinary?”

“What’s the best outcome you can imagine.”

When you ask big questions you’re helping your coachee open to possibility and possibility is where people are usually at their best.