I’m Kira Callahan

Sales and Confidence Coach, and Founder of Conversation Gym

I help YOU build confidence and master sales conversations so you nail them when it counts.

Private Sales and Confidence Coaching

Conversation Gym provides effective, enjoyable 1:1 coaching that creates rapid results. Your program will be tailored to your specific needs and always includes practical real-life scenarios and targeted homework to make sure your performance lift lasts.

Team Coaching

Success starts in the heart and between the ears. Kira delivers short, interactive, and emotionally impactful group sessions to build Advisors’ confidence and sales success.

I take a different approach from most sales coaches.

I teach you to speak and sell from the heart. It’s good business!

Real and lasting success starts with YOUR ORIGIN.

Most people know their origin story. I teach you to OWN YOUR ORIGIN STORY. This unique process will fuel your confidence and sales success. Together, we take what authentically drives you and craft your unique key messages. Doing it on your own is TOUGH STUFF! It’s much more effective to work with a coach who can offer skill, objectivity, compassion and results.


I’ve worked with thousands of Advisors since 2002 and one of my favourite things is to pull your brilliance out of you and help you put it all together in a way that makes you excited to communicate it to clients.

There is GOLD in your Origin Story. I HELP YOU OWN IT!

No matter where you are in your career: a seasoned veteran grappling with Imposter Syndrome, a mid-career advisor looking to upgrade to serving HNW clients, or a newbie who wants to start strong and build fast, it takes both skills and confidence to get there using the building blocks below.


Communication strategy to Convert your leads into calls and meetings

Skills Mastery

Practice with the expert and nail your sales conversations when it counts.

Own Your Value

I teach you how to Own & Articulate your Value.

Maximize Profit

Maximize profit from your current and acquired books of business.

Who is the Coaching For?


If building a book of business is based on your ability to sell, and your happiness is based on your ability to do that with integrity and authenticity, this coaching is for you. I work with Financial Advisors, Insurance Advisors or Agents, Portfolio Managers, Financial Planners, Wealth Advisors, Investment Consultants, Wholesalers. The coaching is private, tailored and highly effective.

Sales Leaders

Conversation Gym is a valuable resource in the following scenarios:

  • You want to boost morale and confidence with a refreshing, original group presentation
  • Confidence issues are impacting Advisors’ prospecting activity and closing rate
  • Advisors are struggling to shift from face-to-face to phone and digital prospecting
  • Your high performers are feeling neglected and would appreciate private sessions that give them an edge
  • Your own prospecting and sales skills are rusty, and you want to tone them up to be a more effective coach
I want more clients.

Most Advisors are good at 75% of the skills needed to bring in clients. The missing 25% is what stops you from closing more business. Each Advisor is unique. The private coaching zeros in on just the skills you need to master. Articulating the value of what you do so people get it, building trust quickly, earning greater share of wallet, handling objections, making compelling offers, getting them to sign and transfer funds, and more.

I’ve acquired a book and want to maximize the business I get out of it.

How do you introduce yourself and build a relationship quickly? How do you reactivate dormant clients? How do you dissolve the objections and emotions neglected clients will hit you with? How do you maximize new business, and respectfully let go of the clients who would be better served elsewhere?

Private Conversation Gym coaching will guide you every step of the way to building warm, lasting and profitable relationships with your newly acquired clients.

I want more confidence!

All of us struggle with confidence from time to time, and for many, self-doubt and negative thought patterns stop us from achieving what we know we’re capable of. Imposter Syndrome. A bad sales week or month. Doubting our value and expertise, fearing objections or questions we can’t answer, feeling intimidated to approach people we know we can help and would love to have as clients, and on and on.

Kira is particularly skilled at helping you build a solid foundation of confidence based on who you are, not just what you do.

I’m new. I want to build fast and do it right.

Option A: Spend years bumbling around figuring out a niche, business model, prospecting approaches, key messages, etc… while burning lots of leads in the process. (Kira speaks from experience here!)

Option B: Invest in a caring, effective coach and compress years into a few months of intensive focus. You may book a chat with Kira to discuss you needs IF you:

  • have at least six months in business
  • know your products, services, compliance
  • have a minimum of 150 leads
  • you are hard-working, determined and willing to push through the discomfort of prospecting
  • you are a caring person of integrity. No ‘Jordan Belfort wannabes’, thank you


About Me

Since 2002, I’ve had the pleasure of coaching more than 6,000 financial professionals, coaching them to master their sales conversations and build a thriving practice they love.

It can be tough to sell yourself! You need skills and confidence. Helping you build a solid foundation of both, and then cheering you on as your sales increase is deeply rewarding. I love my work!

I didn’t start out working with the financial community – I went to school for music and acting and I was a professional jazz singer for 20 years.

Back in 2002, I got a ‘day job’ working at a top training firm that partnered with financial companies. I enjoyed the work so much that it grew into a second career that I love even more than music.

Why do I love this work? Why is it so important to me to help you build your core confidence along with your skills? Well, that’s personal. We have to go back a bit…

There I am, 13 years old, staring at myself in the bathroom mirror, trying to get up the courage to go to school. Up until then I had been a happy, outgoing kid who basically got along with everyone. But that year, everything changed. A group of bullies made my life hell. It crushed my confidence. Grade 8 was also the start of a bad run. Several darker things happened to me over the next few years, including assault.

It took years of hard work to regain my confidence and tap back into the happy, vibrant person I was, but I did! Now, along with my professional experience, I leverage the wisdom, strength, and empathy I gained to be a highly effective sales and success coach. No matter where you are in your career: a seasoned veteran grappling with Imposter Syndrome, a mid-career advisor looking to upgrade to serving HNW clients, or a newbie who wants to start strong and build fast, it takes both skills and confidence to get there.

It helps to work with a Coach who knows your world, understands the courage it takes to sell yourself, and can help you build the confidence and skills you need to get it done.


Online Coaching Resources

Why Is Building An Advisor's Confidence Personal To Me?

I’ve been coaching Financial Advisors for eighteen years now, helping them master their sales conversation skills and bring in more business. I love my work. But I used to be a singer – so why am I so jazzed about doing this?

How to Build Your Confidence on Solid Ground

One of the most powerful predictors of success for any sales professional is their level of confidence. We know this instinctively, but why is it so? For the simple reason that thoughts generate feelings, and how we think and feel determines how we act.

Owning Your Origin Story Fuels Sales

Owning your Origin Story in a way that can fuel your sales conversations takes time and some crafting of key messages. You can do it on your own, but it’s tough. It’s much easier and more effective to work with a coach who can offer skill, objectivity and compassion.

Find Your Balance. Set Your Goals. Own Your Origin . Speak From The Heart.

To be an entrepreneur, practice owner or sales rep, is to face yourself every day.  With no one dictating our schedule or how we do what we do, we are gloriously free to soar, or fall flat on our faces.  It’s up to us. 

What tools and support do you need to be functioning in top form? 

Saying that entrepreneurs and sales reps do it all by themselves is an inaccurate description, of course.  We need a wide array of experts to draw upon and a supportive community of friends, colleagues and loved ones if we are really to reach the heights we’re capable of.

And we need confidence and courage. 

When you’ve been stuck in a tough patch running the biz, or feel you can’t seem to get ahead of it all, confidence and courage can be in short supply. 

If you need me….I am here! 


Don’t Wait Any Longer. Start Forging Your Confidence & Conversion Path Today!