6 Top Coaches Shared Their Biggest Coaching Challenge

Are you struggling to run a successful online coaching business?

Running a successful coaching business can be challenging and draining at times.

To help you overcome some of the challenges, we have asked the following question to some of the most successful coaches.

What’s your number one challenge when running a successful coaching business, and what is your best advice to overcome that?

All these coaches shared valuable insights in their responses.

I’m thankful to all the coaches for their generosity in sharing their secrets for success. 🙏

Enjoy the responses, and here’s to your coaching success! ✌️

Jamie Mason Cohen is a certified leadership development and resilience expert. He is a keynote speaker as well as a regular commentator on CNN, Forbes, and The Morning Show. 

He has worked with businesses and organizations in over 21 countries.

What’s your number one challenge when running a successful coaching business, and what is your best advice to overcome that?

In terms of facilitation/group coaching two main challenges are packaging services as a follow-up, how to sell what you do effectively without being ‘salesy’, and pricing.  The back-end offering is key and often the most elusive component of business workshops.

What offerings can you embed into the business session that leads to a clear, relevant follow-up that audiences want/need/feel a sense of urgency to bring you into their teams?

1. Provide 3 payment level options 
2. Partner with leaders already established within these Groups who have built-in relationships
3. Get better at learning how to speak about what you do in straightforward, simple, and clear terms. 

Stephen is the President of Ideal Realized International Coaching LLC (IRI Coaching) in Washington State USA. He is a Certified Professional Coach (CPC) and Energy Leadership Index Master Practitioner, An International Keynote Speaker, and Creator of the “Knowing Me Is Knowing You,” Relationship Mastermind.

With a cumulative experience of 17 years working with people in various communities, Stephen has helped both women and men discover themselves, unlock their potential, and get to live their lives on their own terms a life of purpose, meaning, and fulfillment.

He attained his Professional Coach training with dual certification at the Institute for Professional Excellence in Coaching (iPEC) in the USA and a Commonwealth Diploma in Youth and Development Work at the University of Nairobi. Stephen is on a World mission to see that women and men will no longer be held hostage by victims of circumstance in whatever form, whether cultural, social, or spiritual in order to realize their maximum potential.

He is a proponent of concepts dubbed The “Iam Factor,” a concept behind all his coaching programs and activities addressing topics such as Getting Unstuck, Confidence Coaching, Relationship Coaching, Peak Performance, and purposeful living.

What’s your number one challenge when running a successful coaching business, and what is your best advice to overcome that?

Marketing and converting customers can be a major challenge for any business, and this has been a key challenge for me in my coaching business. However, there are ways to overcome this challenge without spamming people or joining social groups to get customers, which I personally scorn;

However, the following steps can be of much help.

1. Set your coaching business apart by being different or 10x better than your competitors
2. Create amazing free content that can help you market your coaching business more effectively
3. Use tripwires to attract potential customers
4. Be comfortable with asking for referrals
5. Create strategic alliances with other businesses
6. Find out where your customers hang out and engage with them there
7. Make your message strong and clear
8. Drive people to your website

Among all the above solutions to the coaching marketing challenge, strategic alliances remain my favorite approach because of the following benefits, they immediately earn your trust with clients because of the benefit of association, establish your business in the community, are are generally cost-effective.

Alliances are formed with other businesses that share your target audience. For example, if you are a coaching business focused on career development, you could form a strategic alliance with a company that provides resume writing services or form an alliance with a company that provides training services to your clients. This way, you can offer more value to your customers and reach new audiences.

You can find companies to form alliances with by brainstorming with potential partners who share your target audience, look for companies that share a common vision and mission or companies that align with your company’s core values. Once you’ve identified potential partners, you can outline alliance proposals that make sense for both parties, such as this alliance between the WP Minds blog and other Coaches that creates a valuable resource for coaches while providing exposure and wider reach for the coaches who contribute to it.

Simply put, determine your goals and come up with a plan that benefits both parties.

Rosalyn Palmer is a transformational coach, therapist, and acclaimed author, known for igniting positive change and well-being. With over 20 years in corporate roles, including founding an award-winning PR agency, Rosalyn understands the challenges of success.

Specialising in Advanced Rapid Transformational Therapy (RTT), Clinical Hypnotherapy, and NLP-based coaching, she empowers high achievers to create authentic, balanced lives. Her coaching blends practical business insight with emotional growth, resonating from working with Tony Robbins to overcoming cancer and personal struggles.

As a former radio well-being expert and podcast host, Rosalyn delves into mindset intricacies. She authored the award-winning “Reset!” and co-authored Amazon bestsellers. Rosalyn guides with authenticity, resilience, and transformation.

What’s your number one challenge when running a successful coaching business, and what is your best advice to overcome that?

An area that is often overlooked in coaching, particularly by aspiring or new coaches, is that of actually working on your coaching business rather than just working in it.  Even as a former marketer, I underestimated it, and yet, as I see many coaches throw in the towel and declare that running a successful coaching business is just too demoing, it stands as the cornerstone of a successful coaching practice. 

As a coach, you’re driven by passion and armed with skills to create impact. But there’s a twist: being an exceptional coach is merely one part of the equation. Embracing the role of a savvy businessperson is the second piece.

Coaching revolves around guiding growth and transformation, but there’s a parallel journey – your role as a business owner. Much like you empathize with your clients, you must connect with your coaching business. Understand its pulse, needs, and aspirations. See the bigger picture and know that in most new businesses, in the first year, you work for the business; in the second year, the business may work for itself; and in the third year a well-run business with work for you.  

And behind all of this there is a secret: Before immersing yourself, ensure your own emotional well-being and foundation are secure.

Imagine it as preparing for a flight: they remind you to secure your own oxygen mask before helping others. Apply the same principle here. To guide others effectively, you must stand on firm emotional ground. Elevate your well-being to be the best version of yourself.

Here are five simple strategies to meet this challenge head-on:

1. Prioritise Self-Care: Dedicate daily time to nurture your emotional well-being. Whether it’s meditation, exercise, journaling, or unplugging – allocate moments to rejuvenate.
2. Boundaries Are Crucial: Just as you set limits with clients, apply them to your business tasks. Structure a timetable that respects personal time and prevents burnout.
3. Embrace Continuous Learning: Welcome the exploration of the business facet of coaching. Attend workshops, read, or enroll in online courses to understand marketing, finance, and client management.
4. Craft Your Unique Narrative: Develop a compelling story for your coaching business. It’s not just about what you do, but why you do it. Your story should resonate with potential clients and set you apart.
5. Delegate and Collaborate: You’re not alone in this journey. Delegate tasks others can manage and collaborate with professionals who excel in areas you might not. Outsource as soon as possible and as much as you can afford.

By weaving these strategies into your journey, you’ll strike a balance between coaching brilliance and entrepreneurial prowess. As you evolve, keep in mind that every stride you take in refining your business translates to a legacy.  You are laying the groundwork not only for your best business but also for the prosperity of those you touch. 

And your emotional well-being acts as a compass, guiding you through this challenging but amazing path.

Lisbeth Ceballos is an experienced Leader, Coach, and Facilitator who expertly combines her unique life and work experiences into one-of-a-kind customized engagement. Emigrating to the United States from Venezuela, Lisbeth combines her global, multicultural, and inclusive worldview with informed, practical insights that lead to her client’s personal and professional growth – thereby benefiting both the sponsoring organization and the individual participants.

With the resilience gained from her decades of boldly trying and unapologetically succeeding, Lisbeth now continues her lifelong leadership journey with a growth mindset. As a seasoned, award-winning global executive with over 30 years of experience in the Hospitality Industry, with a Certification as a Strategic Human Resources Professional from the Society Human Resources Management (SHRM-SCP), and as a Professional Certified Coach from the International Coaching Federation, (PCC-ICF), now at the head of her own business, Lisbeth is able to focus her talents on her long-held desire to help Hospitality leaders grow their leadership and business skill sets – at the enterprise, team, and individual levels.

What’s your number one challenge when running a successful coaching business, and what is your best advice to overcome that?

The biggest challenge as a solopreneur is to manage the hours and manage the volume of business so that you can deliver excellent customer service while succeeding. To overcome that challenge is important:

1. Remember that customer service should be your utmost priority
2. Something that works well for me is meditation and finding balance every morning before I start my day. This allows me to start from a balanced place and allows me to organize my day much more productively.
3. Have a set working schedule; this allows me to be more productive when I have a set schedule for achieving all my goals for the day, the week, the month

Jon Covey is a Success & Business Coach who helps business owners get more leads, book more meetings & increase sales. 

Jon’s expertise extends beyond theoretical frameworks. 

He’s a firm advocate of personalised communication and has developed a repertoire of scripts that empower businesses to navigate conversations seamlessly and purposefully. 

What’s your number one challenge when running a successful coaching business, and what is your best advice to overcome that?

The primary challenge most businesses continue to face is lead generation.

Here’s why:

Many businesses misunderstand the concept of a lead. 

While they grasp the purpose of a lead, they often believe that a lead exclusively refers to someone who explicitly expresses interest in their products or services. 

Unfortunately, this narrow perspective leads to missed opportunities.

So, what truly constitutes a lead?

A lead encompasses various interactions, such as:

•  A new subscriber to your newsletter
• A submission on your website
•  A like on your social post
• A view of your profile
• An email response
• A comment

These interactions qualify as leads. While they might not all be immediate hot prospects, they possess potential. 

Your mission is to guide these prospects into becoming paying customers.

But how do you accomplish this?

You engage them in conversation.

• Reach out through DMs
• Initiate contact via email
• Send a well-crafted text message
• Leave a personalised voice note
• Make a direct phone call

Initiating these conversations is key. 

My top advice is to develop tailored scripts for each scenario. 

By doing so, you’ll always know what to say and when eliminating the frustration of aimless discussions.

To ensure success, commit to producing meticulously planned content that resonates with your ideal customer profile (ICP), drawing them in and keeping them engaged. 

Over the next 30 days, design content that delivers substantial value to your audience. Simultaneously, proactively connect with the leads that show interest, and you’ll cultivate a very healthy pipeline.

Peter integrates his 20 years of business and leadership experiences from the automotive industry, his professional skills as a life coach and trainer, and the deeply personal learnings from his own transformation into his coaching approach.

He is dedicated to a mission aimed at redefining the roles of both individuals and companies. His goal is to empower them to amplify their positive, human-centric impact on the world.

Peter finds his motivation in the powerful energy that emerges when individuals embrace their true authentic selves and discover the purpose that drives their lives.

His offerings encompass a spectrum of services, ranging from personalized individual coaching programs to impactful leadership coaching sessions and team development workshops.

What’s your number one challenge when running a successful coaching business, and what is your best advice to overcome that?

My biggest challenge in running my coaching business is my own mental fitness. I find that I can simultaneously be both my greatest hurdle and most potent motivator. Each impactful move I take or negative thought has origins in my mind. Cultivating a positive mindset and summoning the necessary courage to confront and conquer my uncertainties stand as the paramount factors in steering a thriving and fulfilling coaching business.

Having spent nearly two decades in corporate, I deeply appreciated the structured environment by colleagues, peers, hierarchy, email correspondence, and calendars. However, as a solopreneur, this intricate support and accountability system evaporates, leaving me solely responsible for redirecting myself when my mind drifts off.

For operating a coaching business that profoundly impacts the lives of others, I offer these 3 tips:

Cultivate and uphold daily rituals:

Create and maintain daily personal and business-related habits, designed to fortify your mental well-being and regularly recalibrate your business approach. First, we create the habits and then the habits create us.

Commence with tiny habits first (e.g. a 2-minute reflection about positive and negative thoughts) and focus on consistency. As these habits solidify, expand them if necessary.  

2-minuteWithin the scope of my business, I run a structured daily hour-long routine addressing all fundamental steps required to create and maintain clients while keeping my business focused.

Cultivate your own network of accountability:

Create your own accountability network with like-minded people and entrepreneurs. The synergy derived from such connections proves invaluable in counteracting the overwhelming waves of fear and doubts.

Engage a coach to uncover your self-sabotage:

Find guidance from a coach who can support you in digging deep into your self-sabotage. The insights from this introspective journey are among the most profound gifts you will encounter while navigating the complexities of running your business.  

Managing these 3 strategies allows you to run your coaching business while gaining the maximum joy and impact out of it.

Conclusion

We appreciate all the successful coaches for sharing their personal challenges of running a successful coaching business. We hope these amazing responses will help you overcome the challenges as well.

What’s your number one challenge when running a successful coaching business, and what is your best advice to overcome that?

Feel free to share it in the comments below.