Podcast Summary: Courage & Clarity with Steph Crowder

Episode 150: Design a Challenge Inside Your Program to Get Faster Results
Date: September 8, 2025
Host: Steph Crowder

Episode Overview

In this episode, Steph Crowder shares a behind-the-scenes look at how designing and implementing a challenge within her coaching programs rapidly increases client engagement and accelerates results. She breaks down the strategy behind her current 30-day sales challenge, addresses common mistakes coaches make with challenges, and offers tactical advice for crafting effective, result-driven sprints within group programs, masterminds, and even courses. This episode is rich with actionable steps, mindset shifts, and practical templates for any coach or course creator wanting to help clients get tangible results quickly.

Key Discussion Points & Insights

1. Why Add a Challenge Into Your Program?

• Year-long programs provide plenty of time for results, but momentum and attention wane over time.
• Challenges shake up routines, create "first day of school energy," and re-engage clients who may have lost focus.
• Quote (04:55):
  "It is always very welcome. And it also, like I already mentioned, it helps people speed up their results." – Steph Crowder

2. Structuring the Challenge: The 30-Day Sales Fast Track

• Each day features a short, actionable video (via Loom) and a single bite-sized action.
• Delivered through a dedicated Slack channel; clients are prompted to post daily takeaways and homework.
• The entire challenge is crafted around a specific, measurable result:
  “Signing one to three new clients in the next 30 days.” (11:20)
• Both new entrepreneurs and high-level clients benefit; skills are universal and foundational.

3. Core Elements for a Successful Challenge

• Result-oriented: Pick a specific, ambitious but achievable transformation.
  • Avoid vague prompts (e.g., just “exercise every day”) in favor of clear before/after targets.
  • Quote (13:14):
    “When we know and we commit to what result we are aiming towards... Even if people don't get all the way there, think about how far they will come.” – Steph Crowder
• Simplicity in daily actions to ensure completion.
  • Each step should take 15 minutes max, with videos under 10 minutes and simple actions.
  • Quote (30:37):
    “The best challenges, the most transformational challenges, are very, very unburdened and very, very simple.” – Steph Crowder
• Filling Gaps: Use challenges to address curriculum gaps and real-time client needs as they arise.

4. Common Mistakes with Challenges

• No transformation or clear result: Avoid creating challenges without a concrete, measurable outcome.
  • Quote (25:21):
    “Just like our offers, we want there to be a clear before and after if we're gonna do a challenge.” – Steph Crowder
• Overcomplicating daily actions:
  • Risk of overwhelming clients leads to decreased completion.
• Not recognizing growth edges:
  • Pushback (“I don’t want to do this!”) is valuable feedback and highlights where support/coaching is needed.

5. Design Process Detailing

• Brain Dump First: Write down everything you’d personally do to reach the challenge's result in that timeframe.
• Structure & Organize:
  • Tools like ChatGPT are useful as organizational assistants after you’ve defined your process.
  • Quote (37:54):
    “Your business depends on you using the genius inside of your brain. It's better than any computer.” – Steph Crowder
• Phases:
  • Break long challenges into phases (e.g., 3 blocks of 10 days: Clarifying, Connecting & Converting, Troubleshooting & Momentum).
  • Addresses key areas: getting clear, taking action, handling roadblocks.

6. Client Incentives & Longevity

• Prizes incentivize daily participation and completion (e.g., access to special trainings or coaching sessions that are relevant and valuable).
• Challenges can be repurposed as ongoing onboarding, fast tracks, or bootcamps within your main programs for future clients.

Memorable Moments & Notable Quotes

• On Purposeful Challenge Design:
  “If you're going to do this, you really want to think about what kind of result is achievable in the timeframe that you're doing the challenge, and also what kind of result would really serve people in the broader context of your program.” – Steph Crowder (16:40)

• On Updating Curriculum Through Challenges:
  “We are always evolving, our clients are always evolving, and the market is always evolving. You're never done. You really need to think of your curriculum and your teachings as like a living library.” – Steph Crowder (22:00)

• On Simplicity Over Complexity:
  “The best challenges, the most transformational challenges, are very, very unburdened and very, very simple.” – Steph Crowder (30:37)

• On Using Challenges to Identify Coaching Needs:
  “I'm already getting some pushback...that's really good for me to know as the coach and the leader of the program. It's like, oh, we need to do more coaching around this.” – Steph Crowder (24:55)

• On AI as a Tool, Not a Stand-In:
  “The information comes from my brain. The strategy comes from my brain. And then I often use tools like ChatGPT to help me organize it and simplify it. In my opinion, that is all you should really be turning to ChatGPT for when it comes to your craft.” – Steph Crowder (37:40)

Timestamps for Key Segments

• 03:00 – 09:00: High-level overview and history of Steph's challenges within her programs
• 11:00 – 16:40: Specifics of the 30-Day Sales Challenge and defining concrete goals
• 19:30 – 24:30: Using challenges as a dual tool: engagement and curriculum improvement
• 25:20 – 31:30: Biggest mistakes and why daily simplicity is vital
• 33:00 – 39:00: Design process, the role of tools like ChatGPT, and challenge phase structure
• 41:00 – 45:30: Incentives, prizes, and how challenges become long-lasting assets in her business

Takeaways & Application

• Running a time-limited, result-focused challenge inside your paid program can ignite engagement, drive quick wins, and make your core content stickier and more effective.
• Keep daily actions simple, clear, and highly achievable; complexity reduces efficacy.
• Use the process not just for your clients, but as a feedback loop to strengthen your curriculum and identify coaching leverage points.
• Challenges can become evergreen assets—repurpose them for onboarding or fast-track modules for future cohorts.

Connect with Steph

• Instagram: @heystephcrowder
• Website (for mastermind waitlist): stephcrowder.com/mastermind

Episode Close:
Steph encourages listeners to experiment with challenges in their own programs and share results or questions with her on social media or via email. She concludes by wishing all listeners the courage and clarity to go after their dreams.