Strategic Planning
For Entrepreneurs or Teams

Effective Roadmaps for Business Growth and Team Success

Every founder I encounter typically seeks the same things at the start of each year:

  • Clear goals and a concrete strategy for achieving them.
  • Detailed plans for reaching these goals, including specific projects, metrics for tracking progress, and recruitment strategies.
  • If they lead a team, they want their team to fully grasp and share the excitement for the upcoming year’s plans.

Effective strategic planning fulfills all these needs. It’s a fact that plans evolve over the year – I’ve yet to see a plan that doesn’t require adjustments. However, the process of planning itself is immensely valuable. It’s a chance to either strengthen your resolve as a solo entrepreneur or collaboratively craft a future roadmap with your team. Engaging people in the planning process boosts their commitment to the hard work needed to achieve these goals.


A common hurdle for founders in strategic planning is the struggle to balance being both a facilitator and an active participant. This dual role is challenging. When you participate, it’s difficult to remain an objective facilitator. This shift affects the entire group’s dynamics and participation. If you’ve tried to juggle these roles, either for yourself or with others, you’ve likely faced this dilemma. 


Bringing in an outside facilitator for the planning phase is the optimal solution to 1) realize the aforementioned goals and 2) circumvent the pitfalls of trying to facilitate and participate simultaneously. That’s where my expertise is invaluable.


Overview

Effective strategic planning can significantly boost your company’s revenue growth, provide clear guidance for you and your team, and clearly define how each team member’s contributions drive your company’s success. In our collaboration, we’ll create a tangible, quantifiable plan that will guide your team’s activities for the coming year. 


I place a strong emphasis on fortifying team dynamics as part of this process, so I offer additional sessions aimed at team building and professional development to further enhance our strategic planning efforts.


Who’s It For

My strategic planning expertise is ideally suited for:

  • Entrepreneurs or full-time professionals aiming to expand their side hustles, currently generating at least $150,000 in annual revenue, who are seeking strategies to overcome growth plateaus.
  • Entrepreneurs with annual revenues of at least $500,000, looking for effective ways to scale their business without the risk of burnout.
  • Bootstrapped startup founders eager to scale from $1M to over $10M in annual recurring revenue (ARR), or grow their team size from about 10 to 50+ employees.

If you’re on the cusp of these benchmarks but haven’t quite reached them, my strategic planning services might still be an excellent match if:


  • You’re committed to investing in your business to break through current limitations or to achieve ambitious targets.
  • You have the necessary budget to engage in a collaborative planning process.

Format

The ideal strategic planning format depends on the objective, the size of your team, and how much of a change in direction you anticipate. Strategic planning is also one of the best ways to kick off a long-term coaching relationship.


The most common format for independent creators is a single, full day of 1:1 work together. The most common format for creators with team and exec teams of bootstrapped startups is 2-2.5 days with a combination of planning and trust-building time.


I work with each strategic planning client to design a program that will best meet your needs.


Each program consists of some combination of the following elements:

  • Mission, Vision, and Values
  • Three Year Strategy
  • Goals, Priorities, and Objectives
  • Developing Purpose
  • Metrics (OKRs & KPIs)
  • Process
  • Team Building
  • Roadmap Development

Mission, Vision, And Values

Whether you plan to build a business around you or you plan to scale a company, having a clear mission, vision, and values helps you focus on what truly matters to you. They also become a tool for recruiting people onto your team.


This is a focused exercise to get clear on why you got into this business to begin with, how you’re trying to transform a piece of the world through your work, and the principles you’ll use to shape your actions along the way.


This could easily be a waste of time. Instead, we focus on making it actionable and clear as quickly as possible so it can fuel your business going forward.


Three Year Strategy

Strategy starts with your mission and vision and dictates how you’ll bring them to life over the next 1-3 years.


Where are you trying to go? What are the different paths you can take to get there? How do you want to build your brand? Who are the right customers? What is the right mix of products and services?


Setting strategy is about choosing the core drivers of your business and focusing on that core to the exclusion of everything else you’ve chosen not to be or do.


Goals, Priorities, And Objectives

There are many models for structuring goals and priorities. We can use principles from Entrepreneurial Operating System (EOS), Objectives and Key Results (OKRs), or your preferred goal-setting system.


The output of this session is a clear set of priorities backed up by how you will measure progress against each priority, and projects or initiatives you plan to pursue to achieve the goals.


Metrics

Every business has a core set of metrics that help you understand your progress towards your goals. These can range from general business health metrics to specific metrics to track progress against individual goals.


This session establishes a scoreboard for your business and sets you or your team up to report on those metrics on a regular basis.


Team

There are three potential outcomes from a session on team:

 

  • A hiring plan with specific responsibilities, key metrics, and timing (calendar or milestone-based) for each planned hire.
  • Redesigning the existing organizational structure and individual roles to better serve the needs of the business.
  • Evaluating performance of the existing team to 1) promote, 2) move and/or 3) fire teammates to help improve performance.

We’ll start by looking at the current team, then move on to designing the appropriate org structure and roles for the needs of the business, and then making decisions about what team changes to make.


Process

Enhancing efficiency is a key area for improvement in any business — it’s about achieving more with the same resources.


In this session, we’ll dissect the core processes that are crucial for your business’s success. This includes everything from content marketing production to new client onboarding, to the hiring process.


The outcome of this session is a detailed map of your business processes, complete with plans for improvements or modifications to boost operational efficiency.


Team Building

Regardless of the existing trust level within your team, incorporating trust-building activities into your strategic planning yields significant returns.


Here are some examples of team-building exercises we can implement:


  • Professional Stories – A session where each team member shares key moments from their career journey.
  • Listening Walks – An activity that pairs team members to share and listen to each other’s stories for 15 minutes each, uninterrupted. The session concludes with a facilitated group debrief.
  • Lightning Talks – Quick, five-minute impromptu discussions on topics that deeply resonate with your team members.
  • Unsolicited Feedback – A session designed to cultivate a culture of openness, honest feedback, and personal care, featuring a series of ‘hot seat’ feedback exchanges for each team member.

Assessments

I am certified as a Master Facilitator by AJ&Smart, a renowned agency well-known for its innovative approach derived from Google Ventures’ methodologies. This certification is pivotal due to its association with Google, highlighting the importance and effectiveness of the strategies and tools involved.


The AJ&Smart certification emphasizes a results-driven framework for personal and team growth, leveraging practices that have been adopted by leading global companies. This approach ensures a comprehensive and objective assessment of natural abilities, integrating specific tasks and exercises tailored to bring out the best in individuals and teams.


Frequency

Initial strategic planning is flexible and can be initiated at any time. It’s always beneficial to clarify goals and align your team. The duration of initial strategic planning ranges from 2-5 days, depending on your specific goals.


Following the development of your initial strategic plan, it’s generally advisable to hold one major planning session each year. This session can be scheduled at any time, typically aligning with your business’s fiscal year. While most businesses follow the calendar year, you, as the founder, can choose an alternative cycle, such as July-June. Annual planning usually spans 1-2.5 days.


Beyond annual planning, it’s optimal to conduct at least one, but preferably quarterly, sessions to monitor progress and make necessary adjustments. Biannual check-ins generally last 1-1.5 days, whereas quarterly sessions can be a half-day or a full day in length.


Location

Strategic planning is most effective when conducted in person with your team, ideally in a retreat or offsite setting outside of your regular office environment.


If in-person planning is not feasible, remote planning is a valuable alternative. We can tailor the planning process to be engaging and mindful of virtual meeting challenges, such as Zoom fatigue.


Investment

The length of the strategic planning session is determined by the specific program we develop together. The pricing structure is as follows:

  • One day: $7,500
  • Two days: $15,500
  • Three days: $24,000

For onsite strategic planning, additional costs for round-trip flights and lodging apply.

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