Every founder I’ve ever met wants the following to start each year:
- Absolute clarity on their goals and strategy for achieving their goals
- Specific plans to get there, including projects to try, metrics to track progress, and hiring plans to make it possible
- If they have a team, they want the whole team to understand and be excited about plans for the year to come
Strategic planning done well delivers on all of these things. Every plan changes throughout the year — I’ve never seen a plan go exactly as it was laid out. But the process of planning is a powerful opportunity to either gain conviction as a solopreneur or partner with your team to build a plan for the future together.
When people are a part of the process, they feel more committed to the execution it takes to reach your goals.
The most common frustration with strategic planning for founders is trying to be both the primary facilitator AND a participant in the planning process. It doesn’t work. When you switch into participating, you can no longer facilitate objectively. It shifts the momentum and the way everyone else participates.
If you’ve ever tried to do both (either for yourself or others), you might’ve experienced the same challenge. Having an external facilitator join your team for planning is the best way to 1) achieve the goals above and 2) avoid the frustration of participating vs facilitating.
That’s where I come in.
Overview
Strategic planning done well can accelerate revenue growth, clarify direction for you and your team, and make it clear how each person contributes to the success of your company.
Through our work together, we will produce a concrete and measurable written plan that your team will use to inform their work over the next 12 months. I believe in strengthening the relationships on the team as a part of the planning process, so optional sessions focused on team building and professional growth are available as well.
Who It’s For
My strategic planning process is perfect for:
- Independent creators doing at least $500,000 in annual revenue and looking to break through a plateau
- Independent creators doing at least $1,000,000 in annual revenue and looking to scale without burning out
- Bootstrapped startup founders looking to scale from $1M to $10M+ ARR or about 10 to 50+ employees
If you’re close to meeting these criteria, but not quite there, I might still be a good fit for your strategic planning if:
- You are eager to invest in your business to break through a current plateau or push towards an ambitious goal
- Have the budget required to work together
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.
When you reach out about planning, we’ll spend 60-90 minutes running through your needs and designing the best combination of sessions for you.
Each element that can be added to our strategic planning agenda is outlined below, including:
- Mission, Vision, and Values
- Three Year Strategy
- Goals, Priorities, and Objectives
- Metrics
- Team
- Budget
- Process
- Team Building
- Assessments
Mission, Vision, and Values
Whether you plan to building 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 on to 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 initiate 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 your 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.
Budget
Many founder-led businesses operate without a budget, which can lead to stress and anxiety for the founder due to a lack of transparency into what’s going on in the business. I’ve coached founders with debilitating financial stress despite them making hundreds of thousands of dollars a year.
In a budget session, we’ll create or update your budget template to reflect the spending and investments required by your strategic plan. As the founder, you can then outsource to a bookkeeper or fractional CFO, delegate to your ops or finance leader, or maintain the budget yourself.
Process
One element of any business that can almost always be improved is the efficiency — how much you’re able to get done with the same number of resources.
In this session, we’ll break down the key processes that drive results in your business. This could be everything from how you produce content marketing, to how to onboard new clients, to how you hire new teammates.
The output of this session is a process map of the business, including planned improvements or changes to operate more efficiently.
Team Building
No matter the level of trust that exists on your team, integrating trust building sessions into your strategic planning is a high ROI investment.
A few example of team building sessions we can do:
- Professional stories – a session that allows everyone to share the most powerful moments of their career
- Listening walks – a session that pairs teammates and gives them the unique chance to share a part of their story for 15 minutes, uninterrupted, and listen to their partner’s story for 15 minutes uninterrupted; a facilitated debrief at the end brings it all together
- Lightning talks – a series of five minute, impromptu talks about topics that matter deeply to your teammates
- Unsolicited feedback – a session that fosters a culture of transparency, honest feedback, and personal care through a series of hot seat sessions for each person on the team
Assessments
I am certified to facilitate personal and team growth through an assessment called the Highlands Ability Battery, a tool that objectively measures your natural abilities by asking you to perform specific tasks or exercises.
From the Highlands site:
The Highlands Ability Battery measures your abilities based on performance rather than perception. Exercises such as recreating designs from memory, manipulating blocks in space, and putting images in logical sequence are some of the virtual tasks you are asked to perform within a set amount of time. Results based on timed performance are far more reliable than results based on self-perception or personal opinion.
The reports and debrief session I facilitate are one of the best ways I’ve found to help people objectively understand their natural abilities, how those abilities affect their work, how teams can better work together, and how you as founder can set each of your people up for success.
*A note that the Highlands takes about three hours to complete and would need to be done as pre-work in order for this to be included as part of our planning session. The added cost of the assessment is $120 per person.
Frequency
Initial strategic planning can be done any time. It’s always a good time to get clear on your goals and create alignment for your team. Initial strategic planning can take anywhere from 2-5 days depending on your goals.
After building your initial strategic plan, it often makes the most sense to do one primary planning session each calendar year. This can be done at any point during the year, often aligned to the business year you operate on. For most businesses, this aligns to the calendar year, but as the founder you can choose to operate, for example, July-June. Annual planning is typically a 1-2.5 day process.
In addition to annual planning, it’s best to have at least one, but ideally quarterly planning sessions to track progress and adjust to reality. A biannual checkin is usually 1-1.5 days, whereas quarterly planning sessions can be a half or full day.
Location
Strategic planning is best done in person on location with your team. It is best if the planning can be done outside of your offices on a full retreat or offsite.
If circumstances prevent planning from happening in person, it’s better to plan remotely than not to plan at all. We can work together to adapt a planning process that will be both engaging and acknowledge Zoom fatigue.
Investment
The number of days is dictated by the program we build together. Pricing is as follows:
- One day: $15,000
- Two days: $25,500
- Three days: $33,000
For on-site planning, round trip flights and lodging are in addition to the cost of planning.
Testimonials from prior strategic planning clients
“As the founder of the business, I have sought many consultants in the past, but I must admit that finding someone like Barrett has been a rare and rewarding discovery. His structured approach and objective facilitation have resulted in a tangible plan that is not only well-documented on paper but also being effectively implemented across the organization.
Barrett proved to be an invaluable asset during our time together, starting with his ability to ask the leadership team thought-provoking questions that led us to identify our top priorities, all aligned with our overarching goals.
One of the key strengths Barrett brought to the table was his skill in creating a facilitated safe space for our team. His expert guidance ensured that every team member had a voice and was an integral part of shaping the end result. As a result, we experienced increased engagement and commitment from everyone involved, making the strategic planning process even more effective.” – Clint Salter, Founder
“Launching my wine education business had left me in a constant whirlwind of uncertainty for nearly a year. I grappled with the overwhelming task of finding my audience while lacking a cohesive strategy and implementation roadmap.
However, everything changed in just one day spent with Barrett. His strategic planning session surpassed all expectations. Barrett delved into my aspirations and business objectives through a series of insightful questions that brought my vision for the business to life. He then meticulously structured my scattered ideas into a comprehensive strategic plan spanning one, three, five, and seven years. Moreover, we outlined a detailed month-by-month blueprint for 2024 that would start me on the right foot for the year ahead.
Barrett’s unique talent lies in his capability to transform overwhelming ideas, which often led to my entrepreneurial paralysis, into tailor-made, actionable steps. He crafted a plan finely attuned to my professional strengths and weaknesses, providing a roadmap that felt not only practical but also perfectly aligned with my ambitions.
Merely weeks since our intensive planning session, I’ve already initiated my plan with a renewed sense of purpose, direction, and motivation. The impact has been tangible, and I’m excited to see the continued benefits—both immediate and long-term—from our collaboration.
To sum things up, Barrett stands unparalleled in his expertise. His guidance has ignited a transformation in my approach to my business, setting me on a clear path in the years to come.” – Meg Rulli, Founder