In all parts of life, failing is part of learning and growing. In an effort to prevent mistakes, though, some owners closely guard client communication, restrict responsibility, and proactively intervene before anything “bad” happens. 

While well-intentioned, this approach slows development dramatically. New planners become observers instead of decision-makers. They gain theoretical understanding but lack practical confidence. The fastest way to build a competent, confident new planner is to allow them to fail carefully, intentionally, and in controlled environments. Failure, when structured properly, is not a liability. It is one of the most powerful training tools managers can use to develop their people. 

When a new planner succeeds, sometimes they don’t fully understand why. They may attribute the outcome to luck, timing, or the lead advisor’s intervention. But when they make a mistake, their brain engages differently. They analyze what happened, identify gaps in their thinking, and remember the lesson far more vividly.

I remember earlier in my career, one time I expressed my frustration for having to sit in the office and crunch out all of the new financial plans while my senior planner was out of the office trying to develop business. Instead of telling me that he had the more challenging job, he switched places with me for one day, and he worked on the plans while I took the business networking meetings the next day. Long story short, I failed miserably and vastly underestimated how difficult it was, as a 23-year-old, to differentiate oneself from all of the other financial planners pitching business owners. This was much more powerful and motivating than simply telling me it was harder.  Allowing me to fall on my face in a controlled environment had a much larger impact on my development.

Planners who never experience controlled failure often remain hesitant, second-guess themselves, and defer decisions longer than necessary. Planners who experience controlled failure early are more likely to become decisive, thoughtful, and resilient.

The goal is not to throw new planners into high-stakes client situations unprepared. That creates anxiety, damages trust, and harms development. Instead, effective firms use a controlled failure framework, where responsibility increases gradually, and mistakes occur in low-risk environments.

Multi-Phased Approach 

Phase 1: Internal Failure (Zero Client Exposure)

This phase builds foundational confidence without client risk.

Examples include:

• Drafting financial plans for internal review
• Writing client follow-up summaries that are reviewed before sending
• Preparing meeting agendas that advisors refine
• Running planning software scenarios independently

Mistakes in this phase are expected and encouraged. They create opportunities for coaching and refinement without external consequences. The planner learns: “I can try, make mistakes, and improve.”

Phase 2: Operational Failure (Limited Client Impact)

In this phase, the planner’s work affects real workflows, but the advisor maintains oversight.

Examples include:

• Preparing client reports
• Managing data gathering, data entry, and updates
• Drafting recommendations for advisor review
• Handling routine operational tasks

Errors may occur, but they are correctable before materially affecting client outcomes. This phase builds procedural competence and accountability.

Phase 3: Client-Facing Failure (Moderate Stakes)

This is where real growth accelerates.

Examples include:

• Presenting a portion of a financial plan
• Answering client questions during meetings
• Explaining planning assumptions
• Delivering follow-up communications

Minor mistakes may occur — a missed detail, awkward explanation, or incomplete answer. These moments, when properly supported, create the most powerful learning opportunities. The planner learns to recover, adjust, and improve in real time.

Why Overprotecting New Planners Backfires

When owners shield planners from responsibility too long, several negative outcomes emerge:

• Delayed confidence development
  - Planners hesitate because they’ve never operated independently.
• Reduced engagement
  - Without meaningful responsibility, planners feel underutilized.
• Slower skill acquisition
  - Observation alone cannot build decision-making ability.
• Higher turnover risk
  - Ambitious planners want growth. Without it, they leave.

Attempting to prevent failure often creates long-term underperformance. Just like a helicopter parent and a snowplow parent can do with their kids!

How to Create a Safe Environment for Controlled Failure

Allowing failure does not mean removing support. It means structuring growth intentionally.

Here are five strategies to consider:

1. Set Clear Responsibility Boundaries

Define what the planner owns and what you retain.

For example:
“You draft the client summary. I review before sending.”

Clarity creates psychological safety.

2. Normalize Mistakes Early

Explicitly tell new planners:
“Mistakes are part of development. What matters is learning from them.”

This removes fear and encourages initiative.

3. Debrief Quickly and Constructively

After a mistake, review:
What happened
Why it happened
How to improve next time

Avoid emotional reactions and finger-pointing and instead focus on process improvement.

4. Increase Responsibility Gradually

As competence improves, expand their role incrementally. Confidence grows through repeated exposure.

5. Separate Learning from Judgment

If planners believe mistakes will permanently damage their reputation, they will avoid responsibility. Make it clear that development is expected, and growth is the objective.

What Happens When Firms Use Controlled Failure Correctly

Firms that implement this approach consistently see planners:

• Gain confidence faster
• Take the initiative earlier
• Develop independent thinking
• Require less oversight over time
• Become client-ready sooner

Instead of taking three to five years to develop a capable planner, firms often see meaningful competency emerge within 12 to 24 months. The firms that can develop their planners faster are the ones that are positioned best for future growth and success. 

The Leadership Shift Required

Allowing controlled failure requires a mindset shift. You are not just protecting clients. You are building future advisors. 

Every competent lead planner today was once inexperienced. The difference is whether they were given structured opportunities to grow and fail.

Failure is not a sign of weakness. It is a necessary step in professional development. When structured properly, controlled failure accelerates competence, builds confidence, and prepares new planners for long-term success. The goal is not to prevent mistakes. The goal is to ensure every mistake becomes a stepping stone toward mastery.

Contact us at info@newplannerrecruiting.com if you have any questions or would like us to help with your next financial planner hire.  

 

Caleb and the New Planner Recruiting Team*

*AI-assisted