Agency Assessment Leadership Planning Day

Here are some tips to make the most of your leadership planning day

Who should be included on that day?

We recommend that only ownership is present on that day. However, key people and managers should be on standby in case we need them for information or to update them on specific thoughts. Depending on how the sessions go, we may opt to update any managers on our progress. 

What happens during this time?

If in person and depending on flights and time constraints, we spend about 1.5 days together and have a dinner meeting the prior evening. Below is a sample timeline*:

Evening Before: Dinner to review assessment findings (If virtual you can ask to schedule a pre-call to review assessment findings)

Planning Day: 9:00am-5:00pm

Planning Day Recap: 9:00am-11:00am

Please see below for a sample agenda

*Note: We will prepare a customized and confirmed timeline for your agency. This is only a sample.

How do we handle differences of opinion?

When people have differing views, we really need to listen―to listen. Oftentimes, the parties aren’t that far off in what they want to accomplish. 

If there is a senior or majority owner, they will be the tiebreaker. If not, we need to strive for compromise and table it for discussion the next day when people have more time to process. 

Where should the meeting take place?

The meeting should take place somewhere private where there will be no interruptions. 

What do we need to do to prepare for this meeting?

We have a list of activities that we request you prepare before the meeting. You can find them below. Please take your time and take them seriously. 

What happens after the meeting?

After the meeting, we will type up notes of our plan for your agency. We will also book our first bi-weekly call for the following week. 


Agenda For Planning Day

  • Evening Before (If Onsite): Dinner with Ownership: This is when we review where we are.
  • Planning Day (9:00 am-5:00 pm): This is when we review where we are going.
    • Agency 2.0
    • Accountability chart
      • Owner roles
      • Owner activities to transfer
    • Vision for:
      • Sales
      • Operations
      • Finances
    • Review Current Team
      • Job descriptions
      • Metrics
      • Incentives
      • Accountability to data
    • Agency Values
    • 1-Year Plan
      • Revenue
      • Profit
      • Goals
      • Agency standards
      • Reporting
      • Steps to take
      • Issues that will get in our way
    • Meeting Cadence
      • Leadership
      • Department
        • Daily 15
        • Bi-weekly check-ins
    • What’s next
      • Traction-book
      • Sleep on it
      • Agency 2.0
  • Regroup in the morning 

Pre-Assessment Leadership Planning Day Homework


  • Review the agenda for Planning Day
  • Review team survey responses
  • Review secret shopper call responses
  • Review reports 

10-Year Plan

Stop and think really hard. What do you want this agency to be in 10 years? Don't just think about the premium. Think about your personal life, your culture, the type of clients, the client experience. Take 10 minutes and just think about the agency in 10 years. Write down what you see. 

Why is this vision important to you?

If you struggled to get a vision for the next 10 years―what distractions kept popping into your head?


Executive Job Details

We often find that many agency leaders are working below their pay grade and filling the gaps for jobs they shouldn’t be doing. Write down all the jobs that fit in these categories:

Desire Zone

You love this work and want to do more of it!

Proficient Zone

You are good at this work but don’t love doing it. 


Drudgery Zone

You hate this work but you may be the only one who can do it currently.

Distraction Zone

You aren’t that good at the work but have to do it.


List all the jobs you do that are below your paygrade: 

APP Approach to Agencies (STARTS):

(S) System: Make everything work with a systematic process.

(T) Time: Everyone has a role, identify the role and free up time.

(A) Accountability: Hold every team member accountable to the process and agreements.

(R) Respond: Issues will not go unanswered, every issue will be documented and handled.

(T) Team: Build a team for the agency’s vision. Roles aren’t people. You deserve the best.

(S) Simple: Everything we do must be simple to understand.


Jot down some notes and questions on our STARTS approach. Which one will be the biggest challenge?


How Agencies Make Money

Review each way agencies make money. Give your agency a grade and write down some thoughts as to why you gave this grade:


Way to Make $



New Business






Coverage Improvements


Book/Carrier Management


Expense Management




Firing Unprofitable Clients