Balancing support and challenge is the key to coaching. Balance doesn’t mean a 50% thumbs up and a 50% kick in the pants. It means adapting to each client’s unique needs and situations. It’s all about context.

Improvising and Learning

Coaching holistically is a continual learning process. We build rapport and a strong, trusting relationship over time. That’s what allows my clients to feel safe to say when something isn’t working and allows me to adjust my approach. I gauge when to listen and validate ideas and when to push a little, always with the goal of helping them progress toward their goals. 

Sometimes I misjudge when to support and when to challenge, but with each interaction, I get valuable feedback and refine my approach. For example, a client once felt more pressured than helped when I nitpicked details of a product launch. Her feedback taught me to be more mindful of where a person is in their journey.

Context Matters

Understanding the unique personality and circumstances of each client is crucial.

Supporting High Achievers

Many of my clients are high achievers. They are way harder on themselves than anyone else, and a lot of times, they don’t need anybody else to push them on certain things. Those folks need more of the support than they do the kick in the butt — the challenge — because they are so internally motivated.

Sometimes I will challenge high achievers, but it’s usually when there are some limiting beliefs happening. They’re not thinking big enough or they’re thinking, “I won’t be able to do this.” This is where I step in to challenge their mindset: 

“Are you thinking big enough? Why not aim higher? What’s holding you back?” 

I find these questions help high achievers stretch their vision and, in turn, their achievements.

Challenging Entrepreneurs

Accountability is super important to my coaching work. My clients know that if we agree to something, I’m going to follow up on it. It’s not always an overt challenge. A lot of them will be motivated to move farther along because they know I’m going to ask them about it the next time we meet.

Another way I help entrepreneurs is with “landing the plane” — turning their brimming ideas into actionable steps. They might need gentle reminders and even summary notes from our conversations. Others benefit from more frequent phone or text check-ins to keep their plans on track. 

Challenging my clients can take various forms — from urging them to take care of themselves to pushing them to ask for their worth. Entrepreneurs often intertwine their personal and professional lives, so I encourage them to take breaks and set boundaries. This often comes with the added benefit of better business outcomes.

Coaching Tools and Techniques

I always try to listen, validate my clients’ thoughts, and help them take the next steps. Here are some of the tools I use to accomplish that.

What’s the Worst That Could Happen?

I use a “worst-case scenario” exercise to help clients overcome their limiting beliefs and step outside their comfort zones. For example, a client of mine struggled with how to approach a new launch. She hesitated between a softer, generic approach and a more specific, direct ask. 

Together, we explored the worst possible outcomes of each option: 

“What’s the worst thing that’s going to happen if you do a more direct ask?” 

“Nothing bad.” 

“What’s the worst thing if you don’t?” 

“Those people won’t know about my launch.” 

This helped put her fears in context.

As we visualized and talked about the potential consequences of action vs. inaction, she came to see that the risks of being hesitant or holding back are often bigger than the risks of moving forward. 

Self-Reflection and Sharing Experiences

Encouraging self-reflection is another critical tool. I might ask an open-ended question like, “How are you feeling today?” Whether through journaling, conversations, or apps like How We Feel that track emotional and practical progress, these exercises help us pay attention to our gut instincts, which can tell us a lot.

I also share my own lived experiences with clients. This often puts their fears into perspective and helps them visualize a path forward.

I remember one client who made her first hire — a decision that didn’t work out. She felt like she failed and questioned her leadership abilities. By supporting her instincts to move on from the hire and sharing my own hiring mistakes, I helped her realize that mistakes are part of the learning process. This became a turning point, showing her that she wasn’t alone and allowing her to regain confidence in her decision-making skills.

Achieve Your Goals

No two clients are alike, so the best coaching involves active listening, intuition, and a deep understanding of each client’s unique needs. My primary focus is helping people grow while achieving their goals. True success, however, is often gauged by their sense of accomplishment, improved confidence, and business growth.

If you’re ready to experience a coaching approach that balances support and challenge tailored to your unique needs, let’s connect.