It was 2am on New Year’s Day over three years ago when I woke up with an idea.

What would happen if I had 100 conversations with inspiring entrepreneurs?

Stephanie Benedetto Padovani's 100 Conversations

I’d been edging towards taking on a 100 Day Challenge of some sort, and was exploring coaching as a new path in my career. After stumbling across Kyle Cease’s 100 Day Meditation Experiment, I finally found my challenge.

Except it felt too big and scary.

Another nine months passed before I finally said (in a conversation with my coach) “I’ll start with 10 conversations and see what happens.”

Within a month I’d extended a personal invitation to friends, clients, family and acquaintances who fit my “ inspiring” criteria in some way to be one of my 100 Conversations. I had a website, initial questions to ask, and a whole lot to learn.

It was over two years before I officially finished my 100 Conversations Experiment. To date I’m still finishing up my commitment to make a video in honor of each and I’ve had WAY more than 100 conversations, since I spoke to some participants two or three times.

Here’s what I’ve learned in the course of these conversations about coaching, purpose, the nature of inspiration…

…and why I recommend that every new or aspiring coach embark on their own version of this 100 Conversations Experiment.

#1 – Trick yourself into doing something by turning it into a game.

I stalled on the implementation of my experiment for nine months because it was way to big and serious for me to take on at the time.

Was I starting a new business? Where was I going to get 100 people to agree to talk with me?

What would we talk about? What if I truly sucked at this coaching thing?

So I “tricked” myself into doing it anyway by turning it into play.

“I’m just experimenting,” I told myself. “Let’s do it and see what happens.”

This got me out of my thinking and into action.

#2 – Discover what you’d like to do by doing it.

I’d done consulting and business coaching for years, but I felt called to go deeper.

I was tired of creating powerful action plans with coaching clients that never got implemented because of fears and mindset issues. I knew I wanted to get real results for my clients.

What I didn’t know was exactly how to do it or what that would look like.

Once I gave myself permission to experiment and play in my 100 Conversations, all I had to do was show up with curiosity and see what happened.

What I discovered was that following my curiosity naturally led me to ask questions and “turn over stones to see what was underneath.” I turned out to be really good at following my intuition, and when I did, the conversation would go exactly where it needed to go for my partner to get what they were seeking.

At first, I was somewhat awkward and nervous about the process. Eventually I learned that if we set an intention for our conversation, we would always – and I do mean always – naturally move towards it, and sometimes even nail it completely in our time together.

The way I coach gradually emerged and evolved in the process of doing it.

This aligns with something I’ve learned from Michael Neill’s teachings, “Infinite intelligence is real time wisdom. It shows up when you need it, and not before.”

I had to stick my neck out and create the space by having the conversations before the “what” of my process showed up. And I can trust that exactly when I need it, what I need will
appear.

#3 – As a coach, it’s your job to show up and do what you know to do. That’s it. And that’s amazing.

One of the biggest mistake coaches make is taking responsibility for the results of their clients.

It comes with the territory. Most coaches are natural born helpers, givers, healers or servants.

How do you know where your job ends and theirs begins? How can you confidently promote yourself when you can’t guarantee results?

As one of my new coach clients put it, “I’m used to working a job where the result was tangible: a report, a plan, sales. As a coach, it’s not me getting the tangible results. It feels totally out of my control.”

Blend that with a history of taking responsibility for other people’s emotions or actions (yep, I’m talking to you, Coach) and that’s a recipe for coaching paralysis.

Case in point, my own story:

I grew up as a people-pleaser. If other people liked me and were happy, that meant I was okay. If they didn’t, well, I was a miserable pile of shit.

I thought it was my responsibility to keep people happy.

My 100 Conversations Experiment taught me to become non-attached to the outcome for my conversational partners and clients.

It wasn’t my job to “make” them do or feel anything. It was my job to show up and do what I know to do to the very best of my ability in that moment. And trust that it’s exactly as it should be.

The more I let go of that need to “guarantee” results for my clients, the more those results happened for them naturally.

Or, if they didn’t, I could trust that they’d received the opportunity or experience they needed to create insight when and if they were ready.

While I still focus 100% on getting results for my clients and do everything in my power to make that happen (emphasis on “in my power”), I also have an agreement with my clients acknowledging that they are responsible for their own results and actions.

This clarity allows me the freedom to show up and do my damnedest, while empowering my client to create the experience for themselves.

#4 – Trust your intuition – even if it’s wrong.

I’ve come to believe that one of the most important skills you can have is the ability to trust yourself.

Your intuition is your internal GPS. It’s a navigational system that gives you turn by turn directions, one small action at a time.

Your intuition is a reliable guide you can trust, but you have to trust it for it to do its job.

Like your GPS, even if you make a wrong turn, it will reroute you to your destination.

At first, trusting your intuition can feel scary. It’s like working a muscle you haven’t used before. It can be easy to second-guess or doubt yourself.

That’s okay.

Trust what you get anyway.

Eventually your awareness will become more finely attuned and your intuition responds on a more subtle level, and your trust grows.

By removing the need to be “right” and following your intuition regardless, the muscle becomes stronger and stronger.

#5 – There’s always value in free conversations with people who inspire you. Always.

A lot of new coaches become frustrated and impatient with doing free “discovery calls.”

“They only attract the people who want freebies,” they say.

I’ve learned to only have conversations with people with inspire me.

Then I always come away inspired, whether they hire me or not.

And feeling inspired is always a good use of my time.

#6 – The more money people invest in coaching with you, the more invested they become.

At this point, I’ve had literally hundreds of free conversations with people in which I’ve done my best to deliver value.

On some occasions I’ve come away thinking, “How could they NOT hire me after that? I just gave them an entire brand story in a one hour conversation!”

So while I lead with generosity, I’ve had to learn to detach from how my services are received and learn how to know when I’m casting my pearls before swine.

There’s something magical that happens when a client invests in coaching with you, especially if the financial investment is beyond their comfort zone.

They show up differently.

The moment when a client plunks down the cash and says, “Yes! I’m in!” a transformation occurs.

They become the person who invests that much in themselves. They step into those shoes and create their own transformation.

A free conversation doesn’t facilitate the same level of investment and transformation, no matter how powerful it may be. Because the client creates their experience – not you.

#7 – If you’re not clear and confident about what you do, no one else will be, either.

I went through many, many of my conversations without having a clear or compelling offer.

How could I? The whole point of my experiment was to figure out what I was doing.

Yet without an offer, no one could become a paying client.

That was okay for a while, until it wasn’t.

If I had it to do over again, I would have come up with a raw offer that I could use to practice and discover what works. I would have done it before I was “ready.”

#8 – People will pay you (more) for telling them the truth they most need to hear.

When I first started my 100 Conversations, I was holding back. I was afraid to say the thing that might piss people off.

Over time, I realized that I’m not serving them when I don’t go where my intuition is nudging me to go.

I still feel the pang of, “Are they going to hate me if I say this?” but I’m learning to do it anyone, once I have permission.

Recently, an entrepreneur came to me for help with his struggling business. It hadn’t make money in three years, had no unique selling proposition, and didn’t provide a solution to a problem. This is a recipe for a business flop.

Most importantly, the owner really wanted to be doing something else. He was just so invested in terms of time and money that it was painful to call it quits.

I told him the disadvantages I was seeing and asked, “If someone took the business away from you, would you fight to get it back?”

His answer was no.

Asking that question helped him acknowledge what he really wanted to do and set limits on his future involvement with the project. He also ended up becoming a client.

If I’d held back or tried to please him, he wouldn’t have had to face his own truth.

Telling the hard truth earns respect and business.

Hell, I still flinch internally sometimes when it’s time to shine the light of truth into those scary, dark corners. But I’m learning that it’s SO worth it for the gold that we’ll find there.

#9 – A single conversation can change someone’s life.

Never underestimate the power of an honest, intentional, brave conversation.

I had a conversation with a man who was losing money on his restaurant. His obligations to it were tied up in the time invested and the emotional passing of his father.

I asked him questions. He was moved. Our conversation validated some things he’d been thinking and generated new insights.

We ended our chat and I never heard from him again.

Over a year later, unbeknownst to me, his wife became one of my students.

She told me that single conversation helped him make the choice to sell his business and he was happily pursuing a new career.

I never told him what to do. All I did was listen, ask questions, and guide him to his own awareness of the truth.

Even one insight can (and I believe, does) change the world.

#10 – Do it before you’re ready.

Whatever you’re considering, whether it’s career in coaching or a trip across the world, don’t wait until you’re “ready” to go for it.

Your conscious mind wants the safety and security of your comfort zone. It will tell you to wait until you’ve created the process, taken the class, written the book or “figured it out” to take action.

It’s never going to be good enough for your critical mind.

Allow your inspiration to guide you forward, one small action at a time, and keep going. It will take you to places you never could have imagined if you’re willing to let it move through you.

“Whatever you can do or dream you can, begin it; Boldness has genius, power and magic in it.” — William Hutchinson Murray