Insurance Agency Employee Development: Build Stronger People Before You Replace Them

An agency owner looks at a phone report and sees a problem.

One employee’s calls average 30 minutes. That seems too long. The owner starts questioning whether the person is working efficiently and whether someone else could do the job better.

But there is a missing piece of information: what happens during those calls?

In a story David Carothers shares on the Power Producers Podcast, the employee was using those conversations to add coverage to existing client relationships and generate revenue.

The call duration was visible. The value of the conversation had been overlooked.

That example captures a larger leadership challenge. Agency owners can identify an activity they dislike without understanding the employee’s contribution, the reason behind the behavior, or the support needed to improve it.

In this episode, David Carothers sits down with Ashley Napier of Solomon Strategic Advisors to discuss recruiting, developing, and retaining employees in an industry increasingly focused on artificial intelligence.

Their conversation asks agency leaders to examine their own role in performance.

Have expectations been explained? Has the person been trained? Have they practiced with support? Has anyone taken the time to understand what they do well?

Insurance agency employee development begins with those questions. The answers can reveal opportunities that a replacement hire or another technology purchase would miss.

Watch the full conversation with David Carothers and Ashley Napier on YouTube.

Start With the Conditions That Shape Performance

Ashley’s interest in leadership development grew from conversations with people who were unhappy at work.

She wanted to understand why capable people felt disengaged. Her exploration repeatedly brought her back to whether employees felt heard, valued, appreciated, and supported by their managers.

Those experiences inform the work she describes at Solomon: strategic planning, team coaching, leadership development, and helping organizations connect healthier working relationships with performance.

For an agency owner, that connection matters.

An employee may struggle because the role is a poor fit. They may lack a particular skill. They may also be working under unclear expectations or trying to follow a process nobody has properly taught them.

Those situations require different responses.

Before deciding what to change, a leader needs to understand the problem.

That means looking at the work itself, the person’s strengths, and the environment around them. It also means being willing to ask whether management has contributed to the gap.

The conversation places responsibility on both sides. Employees need to follow through, while leaders need to provide a workable path to success.

Begin Employee Development During Recruiting

Ashley treats recruiting as the beginning of development.

An agency should understand what it needs from a role before inviting someone to fill it. That requires more than a general desire to hire a producer or relieve pressure on the service team.

What work will this person own? What skills will they need? How will their behavior contribute to the agency’s values and working relationships?

Ashley encourages leaders to consider the agency’s mission, vision, and values alongside technical qualifications.

That does not mean finding people with identical personalities. A team can benefit from different perspectives and strengths. The important question is whether the person can contribute constructively to the environment the agency wants to build.

The interview should also give the candidate a realistic picture of the job.

If an owner expects a salesperson to prospect, manage complex service responsibilities, learn several industries, and operate independently almost immediately, those expectations need examination before an offer is made.

A job description provides a starting point for that discussion.

Without one, the agency and the employee may be working from different assumptions before the first day even arrives.

Clarify the Owner’s Role So Work Can Be Delegated

Ashley points out that some owners lack a clear description of their own responsibilities.

David jokes that the owner’s job is doing everything nobody else does. That may describe the pressure of running an agency, but it offers little guidance for delegation.

An owner needs to identify which work should remain with leadership and which work another person can learn to perform.

Otherwise, a new hire may receive a collection of leftover tasks rather than a coherent role.

For example, an owner might say they need help with sales. The underlying need could involve appointment preparation, prospect research, follow-up, carrier coordination, or relationship management.

Each responsibility calls for different capabilities and support.

Clarifying the work helps an agency hire more thoughtfully. It also creates a basis for evaluating performance later.

An employee cannot reliably meet expectations that change depending on what the owner happens to need that day.

Plan Beyond the First Day and the First 90 Days

Ashley asks leaders to think about the employee’s first day, first month, and first 90 days.

She then adds a question agencies often neglect: what happens after that?

Development does not end when onboarding paperwork is complete or an introductory period has passed.

A producer may understand basic procedures while still needing help with discovery conversations, carrier selection, technical explanations, and account strategy.

A service employee may know how to complete individual tasks while still learning how to prioritize, communicate with clients, and recognize situations that require escalation.

Those capabilities develop through practice and feedback.

An agency therefore needs a progression that connects early training to increasing responsibility.

The progression should identify what the employee needs to learn, where they will practice, who will help, and how readiness will be assessed.

Time matters, but elapsed time alone does not establish competence.

The agency needs to see whether the person can perform the work and explain the thinking behind it.

Use the Four Stages of Development

Ashley describes a development process that gradually transfers responsibility from the leader to the learner.

Its value comes from the two stages agencies are tempted to skip.

Showing someone how to do a task once and then expecting independent performance leaves a substantial gap between observation and ownership.

1. The Leader Does the Work; the Employee Watches

The employee begins by observing a capable person.

For a new producer, that might mean attending a client meeting, listening to the questions, and taking notes.

The leader then explains the reasoning behind the approach.

Why was a particular question asked? Why was another topic left alone? What information influenced the next step?

Observation becomes more useful when the learner can understand the decisions behind the behavior.

2. The Leader Does the Work; the Employee Helps

The learner then participates while the leader remains responsible for the overall activity.

They might ask part of the discovery questions, collect information, or prepare a section of the submission.

This gives them a manageable opportunity to practice.

Afterward, the leader can review what went well and where the employee needs more guidance.

3. The Employee Does the Work; the Leader Helps

Responsibility shifts again.

The employee leads the meeting or completes the task, with the leader available to support them.

At this stage, the learner should explain their thinking. A producer might describe why an account fits a particular market or what additional information is needed.

The leader can assess both the result and the reasoning.

4. The Employee Does the Work; the Leader Watches

The employee then performs with less intervention while the leader observes.

Feedback continues, but the learner has greater ownership.

The purpose is to establish that the person can represent the agency confidently and consistently.

Ashley emphasizes milestones and timelines throughout this process. The employee should understand how they are progressing and what comes next.

Give Producers a Defined Market and Training Path

David shares an example from his own agency that makes the leadership responsibility concrete.

A producer was frustrated. David was frustrated too. Looking at the situation, he realized they had drifted away from the training process he intended to follow.

The producer was pursuing business without enough structure around target accounts, carrier appetite, and preparation.

David describes resetting the relationship and taking responsibility for failing to establish and maintain the roadmap.

That admission matters because having a process somewhere in the agency is different from using it.

David’s broader approach is to develop specialist producers, even within an agency that serves many industries.

A producer who focuses on a defined group of business classes has a clearer learning task. They can build familiarity with the operations, exposures, questions, and markets relevant to those clients.

Their training can then connect directly to prospecting.

Carrier education, appetite discussions, application requirements, and account preparation become part of one development path.

The leader’s role is to keep that path visible and ensure it is being followed.

Otherwise, enthusiasm for finding opportunities can turn into time spent pursuing business the agency is poorly positioned to serve.

Make Immediate Debriefs Part of Producer Training

David attributes much of his early development to conversations that happened immediately after appointments.

Experienced agency leaders would discuss strategy before a meeting. Afterward, they would review what happened while the details were fresh.

They examined what went well, what could improve, and what information needed to be captured.

Ashley calls these conversations curbside chats.

Their value is the connection between a real experience and a specific lesson.

A producer can remember the question they asked, the client’s response, and the moment a conversation changed direction. Feedback becomes easier to understand because it refers to something they just experienced.

A useful debrief can cover:

What the producer learned about the client’s business.
Which questions helped the discussion.
What information remains missing.
Where the explanation became unclear.
What should happen before the next meeting.

The conversation does not have to be lengthy to be valuable.

It does need to happen consistently.

If feedback is repeatedly postponed until a future sales meeting, the agency loses some of the detail that makes the lesson useful.

Match Every Challenge With Support

Ashley emphasizes that difficult feedback should come with help.

Telling someone what they did wrong gives them information. Showing them how to improve gives them a next step.

A leader who identifies a weak explanation can demonstrate a clearer one. If a producer missed an important discovery question, the leader can explain why it mattered and practice how to ask it.

David describes using case studies and role-play during his early training.

Agency principals would act as decision-makers while he worked through a scenario. The exercise included opportunities he needed to identify through conversation.

Feedback followed immediately.

The process gave him a place to make mistakes, understand them, and try a better approach before another client meeting.

Ashley shares a similar experience of receiving technical coaching after appointments. Specific explanations and examples helped her become more confident.

That is the practical difference between criticism and development.

The employee leaves knowing what to work on and how to begin.

As competence increases, the leader’s involvement can change from close instruction to ongoing coaching. Support continues as the work becomes more demanding.

Understand an Employee’s Strengths Before Choosing a Fix

David’s phone-call story challenges the assumption that a visible inefficiency tells the whole story.

A 30-minute call might indicate a training issue. It might also reflect valuable discovery, a complex service need, or a productive account-expansion conversation.

The leader needs context.

David suggests examining what the person accomplishes during the call rather than judging duration alone.

The same reasoning applies to other work.

Someone who is slower at policy analysis may be particularly effective at relationship building. A technically strong employee may need support with difficult client conversations.

Ashley and David encourage leaders to identify those strengths before treating the person as a general performance problem.

That creates more options.

The agency might provide targeted training, pair complementary skills, adjust a workflow, or introduce a tool for a specific task.

The employee still needs to develop. Understanding their strengths helps the agency make that development more useful.

Use AI to Support a Defined Piece of Work

Ashley sees value in AI that helps employees complete repetitive or time-consuming work.

She discusses policy comparisons and organizing information as examples of tasks where assistance can make the service process more efficient.

David connects that idea to the strengths discussion.

If an employee builds excellent relationships but needs help organizing technical information, a suitable tool may support that part of the role.

The agency can then preserve the employee’s contribution while addressing the weakness.

The discussion does not establish that an AI output is automatically complete or correct. Where the work informs coverage advice, the agency still needs qualified review and a clear responsibility for the final explanation.

The useful question is what the tool helps a person do better.

Does it reduce preparation time? Make information easier to review? Help the team communicate more clearly? Create more capacity for client work?

Those outcomes give adoption a purpose.

A tool purchase should connect to an identified task and a way to assess whether the change helped.

Build the Foundation Before Adding More Technology

David questions whether some agencies are adopting AI while leaving basic sales processes unresolved.

He describes organizations that lack a reliable way to capture prospect activity, follow-up, and performance information.

That weakens decision-making.

Technology becomes more useful when the agency already understands how work should move and what information needs to be recorded.

Ashley adds another problem: introducing tools faster than the team can learn them.

She recalls becoming excited about technology, handing it to employees, and moving on to the next purchase before the previous system had been properly integrated.

The team became frustrated. Adoption suffered.

Her reflection brings the discussion back to leadership.

Employees need time to learn a tool, understand its place in the workflow, and practice using it. Management needs to explain the change and check whether it is working.

Adding more software does not resolve that learning gap.

A more deliberate approach gives one workflow enough attention to establish whether the new tool produces a useful result.

Explain the Reason Behind the Process

David returns to a principle from his earlier retail leadership experience: explain why the work should be done a particular way.

An instruction may produce short-term compliance. Understanding the reason helps someone apply the lesson again.

He describes taking time to demonstrate the expected work and explain the details that made the method effective.

Insurance agencies can apply that principle throughout training.

Why does a submission need particular information? Why should the producer investigate operations before approaching a market? Why does an account manager need complete meeting notes?

The explanation connects an individual task to the client experience and the agency’s results.

It also helps an employee make decisions when circumstances change.

Someone who understands the purpose of a process has a stronger basis for judgment than someone who has only memorized its steps.

That takes leadership time.

David acknowledges that finding the time can involve examining distractions and how the owner uses the day. Development needs a protected place in the schedule if it is going to happen consistently.

Ask What Leadership Should Stop, Start, and Continue

Employee feedback should not travel in only one direction.

David describes a stop, start, and continue exercise from his time at Target.

The questions were simple:

What should I stop doing?
What should I start doing?
What should I continue doing?

The difficult part was creating enough trust for people to answer honestly.

That trust developed when employees saw that useful feedback led to action and that speaking candidly did not bring retaliation.

David also acknowledges that leaders cannot act on every suggestion. Some requests fall outside their control or do not address the issue at hand.

The responsibility is to consider the feedback seriously, explain decisions, and follow through where change is appropriate.

Inside an agency, the exercise can uncover problems leaders have stopped noticing.

Employees may identify unclear handoffs, inconsistent priorities, training gaps, or delays that affect clients.

Asking is only the beginning.

The next step is to show the team what will change, who will own it, and how progress will be reviewed.

Apply the Same Listening Skills to Client Risk Conversations

David also uses stop, start, and continue with clients.

He shares an example involving an HVAC company with claims across several lines of coverage.

Employee feedback pointed toward scheduling pressure. Workers were rushed, travel time was tight, and quality control was suffering.

David then examined the feedback alongside operational information and loss issues.

The example shows how employee observations can help a producer identify questions worth investigating.

A complaint about workload may contain a useful clue about how work is organized. That clue becomes more valuable when it is tested against the available evidence.

David uses anonymous feedback in this setting because he does not yet know enough about the client’s leadership environment to assume people can speak freely.

For producers, the broader lesson is to make room for the people doing the work.

They may understand daily pressures that are difficult to see from a leadership meeting or a renewal application.

Those conversations can support a more informed discussion about the client’s operations and risk.

Put Employee Development Into the Agency’s Routine

The episode offers a practical way to begin.

Clarify one role. Identify the work, responsibilities, and expectations the employee needs to understand.
Choose one skill to develop. Focus on a specific activity rather than a broad instruction to improve performance.
Use Ashley’s four stages. Move from observation to supported practice and then greater independence.
Schedule immediate feedback. Make a short debrief part of the activity instead of leaving it to chance.
Connect technology to a real need. Define the task, provide training, and review the outcome.
Ask for feedback on leadership. Use stop, start, and continue, then report what action will follow.
Keep coaching after onboarding. Increase responsibility while remaining available as the employee encounters new challenges.

These steps also complement David’s conversation with Matt Kistler about agency culture and producer recruiting. The opportunity presented during recruiting needs to be supported by the employee’s experience after joining.

Develop the Team You Want to Lead

Ashley and David’s discussion brings agency growth back to the work of leadership.

Hiring the right person matters. Clear expectations, structured practice, and consistent coaching help that person become effective.

AI can support the work. So can better data and more deliberate processes.

The owner still needs to understand the team, make time for development, and respond when feedback reveals a problem.

Before replacing an employee, examine what they contribute and what has been done to help them succeed. Before buying another tool, identify the task it will improve and how the team will learn to use it.

Those decisions can reveal a more productive path forward.

Watch the full conversation with David Carothers and Ashley Napier, learn more about Ashley’s work through Solomon Strategic Advisors or her website, and explore the Power Producers Podcast archive for more discussions about leadership, sales, and agency growth