Strategic Planning for Founders and Creators

Get a clear vision for the year: defined goals, solid strategy, specific action plans, and a team that’s excited and on board.

I Know what you, as Every founder I’ve ever met, want at the beginning of each year

Absolute clarity on your goals and a strategy for achieving them.

Specific plans to get there, including projects to try, metrics to track, and hiring plans to make it possible.

If you have a team, you want everyone to understand and be excited about the future.

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. 

Why This Program?

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 This Program is 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.

What’s inside

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 a team and exec teams of bootstrapped startups is 2-2.5 days with a combination of planning and trust-building time.

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

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 on 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 scorecard for your business and sets 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.

Format & Investment

Who

You and your team.

What

A one- to three-day session to help you grow your business and leadership skills.

When

To be scheduled according to mine and your team availability.

Where

Strategic planning is best done in person with your team. Best if done outside of your offices on a retreat.
Investment

One day: $15,000

Two days: $25,500

Three days: $33,000

The number of days is dictated by the program we build together. Pricing is as follows. For on-site planning, round trip flights and lodging are in addition to the cost of planning.
Working with Barrett has completely transformed my relationship with my work. I've been able to detangle my self-worth from my work, have instituted boundaries around my working time and personal time, and I took my first real, non-working vacation in 6 years.
Amy Palanjian
Creator, Yummy Toddler Food
The investment my firm has made in coaching with Barrett has the highest ROI of any investment we've made to date. Barrett's approach has caused immeasurable growth for both myself and my team. We consider our time with him an essential part of our business. Without him we would be in a much different place.
Darrell Vesterfelt
Founder, Mount Haley
Working with Barrett has offered me great clarity on my business and who I am as an entrepreneur. He takes coaching to a whole other level by helping me squash limiting beliefs that I had about myself and my business, coaching me to understand that I can play a bigger game, that my business can be bigger, and that I really am destined to do bigger things.
Rosemarie Griffin
Founder, ABA Speech
The thing I love most about Barrett is that he has such a great ability to zoom way out to an incredibly strategic bird’s eye view of a company… and in the next moment zoom way in to the personal, emotional level where your motivations and your desires come into play.
Matt D. Smith
Creator and Founder, Shift Nudge

FAQs

Find answers to common questions about our group coaching services and how they can benefit you.

What is 1:1 coaching?

Lorem ipsum dolor sit amet, consectetur adipiscing elit. Ut elit tellus, luctus nec ullamcorper mattis, pulvinar dapibus leo.

Sessions typically last 60 minutes, providing ample time to dive deep into your objectives. We can adjust the duration based on your preferences and needs. Flexibility is key to ensuring you get the most out of each session.
You can expect a supportive environment where your thoughts and aspirations are valued. Our sessions will include goal-setting, accountability, and actionable strategies. You’ll leave each session feeling empowered and focused.
To prepare, reflect on your goals and any specific challenges you want to address. Bring any relevant materials or notes to the session. This will help maximize our time together and ensure a productive discussion.
Yes, if you feel that a different coach would better suit your needs, we can facilitate that transition. Your comfort and growth are our top priorities. We want you to have the best possible experience.

Ready to Work Together?

If you’re ready to unlock your next level of growth and impact, click below to apply.

I’ll review your application and schedule a time for us to discuss your goals and ensure we’re a great fit.