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Annual Strategic Planning Session

"If your actions create a legacy that inspires others to dream more, learn more, do more and become more, then, you are an excellent leader." - Dolly Parton

What You Will Learn

  • Demonstrate your purposeful, proactive and professional leadership.

  • Develop a greater sense of team unity.

  • Ensure your team is fully aligned and engaged in the strategic vision of your practice.

  • Have a formalized and effective method to convey your vision and goals to your team each and every year.

  • Build an Annual Strategic Plan that serves as a snapshot of what you want to achieve and how you will achieve it.

How You Can Get Started

Get Ready for Your Annual Strategic Planning Session

  1. Assign one person on the team to coordinate and organize the Annual Strategic Planning Session in consultation with the Advisors and/or Partners.

  2. Choose the best time of year to have your Annual Strategic Planning Session.

    • Some teams choose October/November/December to ensure they are set for the calendar year ahead.

    • Other teams choose times which correspond with their own or their firm’s fiscal year end.

  3. Schedule the Annual Strategic Planning Meeting onto the calendar as early as possible so everyone has the time set aside – make it the same time of year, every year. 

    • These meetings will take an entire day, so plan accordingly.

  4. It is highly recommended this session is booked offsite to minimize distractions and inevitable interruptions. 

    • Find a comfortable and professional venue that offers privacy for the work you will be doing, as well as the ability to cater the event with food and beverages.

    • Some teams find a venue they really enjoy and go back year-after-year.  This makes the process of booking and organizing easy.  Others prefer variety and choose new locations each year – it’s entirely up to you.

  5. Review the Annual Strategic Planning Agenda and customize as required based on what you want your team to cover.

  6. Review the Annual Strategic Planning Workbook and customize as required. 

    • This is a great tool to guide the entire team through the day, as well as provide everyone with a place to capture notes.

  7. Decide who you want to ‘facilitate’ this session.  This is the person who will manage the agenda, ensure the participation of everyone, organize information, and drive the overall flow of the day.

    • You may have someone on the team who is a natural fit for this role. The ideal person for this would be someone whom everyone respects and who respects everyone, who actively listens and communicates well, and encourages the participation and inclusion of all team members in a positive manner. The ideal candidate will not intentionally sway the team one direction or the other, but instead guide based on general consensus. 

    • You may have someone within the firm who can provide this service to you.  Check with your Practice Management Division and/or others if possible.

    • You may want to hire a third-party to ensure everyone can fully participate in the strategic planning and not be distracted by their role as facilitator. 


Inspire & Engage Your Team

  1. Make sure everyone is emailed a copy of the Agenda at least one month in advance of the session along with instructions on how to best prepare. 

    • Be sure to include the date, time, location and dress code on the Agenda.

    • Inform them that each attendee must be up-to-date with respect to the areas of business operations they are responsible for – this may require a variety of pre-work. 

    • Clearly define any pre-work that may be required.

  2. Email a copy of the Annual Strategic Planning Workbook to ensure they are aware of the primary tool used to manage this process.

    • This can be emailed at the same time as the Agenda or just afterwards.

  3. Confirm all aspects of the meeting logistics 2 to 3 weeks in advance of the scheduled session.

  4. One month leading up to the session, remind the entire team at the Weekly Team Meeting to reinforce the preparation and engagement expected.

  5. In preparation of the event, ensure all necessary items are organized and ready to go. This may include the following items:

    • Printed copies of the Annual Strategic Planning Agenda for all participants

    • Printed copies of the Annual Strategic Planning Workbook and/or a notebook or padfolio for participants to take notes in

    • Flip Charts, Easels & Markers for group work and activities

    • Tape, Scissor & Paper (just in case)

    • Audio visual equipment, if required (this may be supplied by the venue, but may also involve the use of team laptops for recaps, reviews, and/or presentations and discussions).

    • Anything else you plan on using during the session

  6. For other ways to enhance this experience, review Show Gratitude to Your Team.



It’s Showtime - The Annual Strategic Planning Session


  1. Have the organizer show up at least an hour in advance of the scheduled start time to ensure the room is properly set up and ready to go, including testing all audio visual and technology being used.

    • Make sure the room looks professional and comfortable for the attendees.

    • Know where the washroom facilities are located, along with any other amenities you may need to access.

  2. Everyone needs to come fully prepared to the meeting.

    • Each attendee is expected to fully engage and participate.

  3. Make sure everyone has a copy of the following items:

    • Annual Strategic Planning Agenda

    • Annual Strategic Planning Workbook

    • Any other items that will/may be referenced during the session.

  4. One person on the team will be assigned to synthesize the information shared at this session and provide a summary to the entire team using the Annual Strategic Planning Workbook.

  5. Everyone is encouraged to take notes related to their specific role and takeaways.

  6. Use Flip Charts and assign various team members to facilitate documentation on them for a variety of the discussions throughout the day.

    • The person responsible for producing the Annual Strategic Plan for the team should collect all flip charts completed and/or take photos of them.

  7. Participants enjoy breaking up these sessions with individual and/or group work throughout these types of sessions.

  8. Be mindful of daily needs throughout the session:

    • Make sure breaks are taken so everyone can be stretched and refreshed.

    • Make sure food and beverages are provided to keep everyone well energized.

  9. When you wind down the day, provide each of the participants with their “Thank-You” packages to show your appreciation of their commitment and engagement in helping you grow your business.  

  10. If you have a fun team event planned, move onto that part of the day or evening.


Annual Strategic Planning Session Follow-Up

  1. The day after the Annual Strategic Planning Session, the coordinator will send an email thanking everyone for their time.  This email should outline the timeline for receiving the preliminary draft of the Strategic Plan.

  2. Within a week or two of the session, email a copy of the Annual Strategic Planning Workbook to the team and ask for any feedback based on what might need to be fine-tuned or modified.

    • Provide a timeline for this feedback to be provided – one week is recommended.

  3. No later than one month after the session, the finalized version of the Annual Strategic Plan should be in place, including specific goals, activities and individuals responsible for each.

  4. This is when the real work begins to achieve the Outcome-Based and Activity-Based Goals.

  5. Set the Quarterly Strategic Meeting to ensure everyone is focused and moving forward to achieve the desired results.

    • Refer to the next best practice on Quarterly Strategic Meetings for more information. 

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