Did you know that over 70% of entrepreneurs who work with a coach report improved performance and higher profitability? But if you’ve never worked with a business coach for entrepreneurs before, you might be wondering what the first 90 days really look like.
Will it be strategic planning or mindset development? Will you finally overcome those bottlenecks in your business, or just add another meeting to your week?
In this guide, we’ll walk you through exactly what to expect when you begin your journey with a business coach – from the first conversation to the tangible wins that often emerge by the third month. Whether you’re launching a startup, scaling operations, or navigating change, understanding what this early coaching phase involves can make all the difference.
Why Entrepreneurs Turn to Coaching
Entrepreneurship often starts with a vision – but it’s what comes after the idea that determines long-term success. Many business owners face common challenges such as:
- Decision fatigue and overwhelm
- Isolation and lack of accountability
- Difficulty prioritizing goals
- Hiring and team-building struggles
- Plateaued growth or inconsistent revenue
A business coach for entrepreneurs steps in as a strategic thought partner – someone who brings an outside perspective, proven frameworks, and personalized feedback. Coaching isn’t about giving you all the answers. It’s about helping you ask better questions, sharpen your instincts, and take aligned action.
Understanding the Coaching Timeline: The First 90 Days
📅 Month 1: Clarity & Foundation
Goal: Build trust, clarify direction, and identify barriers.
This first month is all about setting the foundation. Most reputable coaches will start with an onboarding session or intake interview to explore:
- Your current business model and structure
- Short-term and long-term goals
- Pain points, blind spots, and recurring challenges
- Your leadership style and personal development goals
Expect your coach to ask deep, reflective questions – not just about what you want to achieve, but why it matters to you. This stage is where coaches uncover the internal and external forces shaping your decisions.
Common activities in Month 1 include:
- Business audits (sales, operations, leadership)
- SWOT analysis or vision alignment exercises
- Establishing measurable 90-day goals
- Identifying KPIs and accountability methods
Outcome: You’ll walk away from Month 1 with clarity on where you’re heading, what’s holding you back, and what progress looks like.
🔧 Month 2: Strategy, Systems & Execution
Goal: Turn insights into a plan – and start implementing it.
By the second month, your coach will help you shift from insight to action. Together, you’ll focus on building the structures and habits that move the business forward.
This is where the real work begins. You may start testing new offers, refining your client onboarding, improving your time management, or delegating more effectively.
Month 2 often includes:
- Creating or refining your strategic plan
- Installing key systems (CRM, automation, SOPs)
- Enhancing your messaging or marketing funnel
- Identifying time-wasters or low-ROI tasks
- Weekly progress check-ins and recalibration
Coaches bring tools, templates, and case studies to help you build efficiently – not from scratch.
Outcome: You’ll start seeing momentum. Operations become smoother, and you’re clearer about what to say “yes” and “no” to.
🚀 Month 3: Leadership, Growth & Optimization
Goal: Develop consistency, expand capacity, and evolve as a leader.
In Month 3, the coaching relationship matures. With foundational strategies in place, the focus shifts to optimizing performance and preparing for sustainable growth.
This is also the stage where you’re challenged to think and lead differently. You might explore:
- Developing team culture or hiring pipelines
- Strengthening your CEO mindset
- Managing stress and maintaining focus
- Creating dashboards for decision-making
- Planning for scale (without burnout)
Your coach may help you rehearse sales pitches, navigate difficult team conversations, or evaluate new opportunities. You’re no longer putting out fires – you’re building a business that runs with more independence from you.
Outcome: Confidence, capability, and measurable progress toward your original 90-day goals.
Real Outcomes You Can Expect in 90 Days
While every coaching journey is unique, many entrepreneurs report the following wins within their first three months:
| Benefit | Description |
| Clarity | You’ll have a clear roadmap tied to your mission and goals. |
| Increased Revenue | Many clients improve pricing, close more deals, or streamline offers. |
| Time Freedom | Systems and delegation reduce overwhelm and create space. |
| Better Decision-Making | With a coach’s guidance, you make choices faster – and with confidence. |
| Momentum | Small wins build trust in your abilities and commitment. |
According to a study by the International Coaching Federation, 86% of companies report that they recouped their coaching investment – and more.
What Makes Coaching Different from Consulting?
It’s a common question: Why not just hire a consultant?
Here’s a key distinction:
| Coaching | Consulting |
| Helps you uncover your own solutions | Provides expert solutions and implementation |
| Focuses on behavior, mindset, and leadership | Focuses on tactics, processes, and delivery |
| Long-term growth and personal alignment | Short-term projects and performance fixes |
| Accountability partner | External expert |
The best business coaches often have consulting experience – but their role is to help you grow into a better business leader, not just fix what’s broken.
Traits of a Great Business Coach for Entrepreneurs
Not all coaches are created equal. Here’s what to look for when choosing yours:
- Entrepreneurial experience – They’ve been in the trenches, not just studied them.
- Coaching credentials – ICF certifications or other relevant training.
- Clear methodology – They follow a structured, adaptable process.
- Cultural intelligence – They understand and respect diverse lived experiences.
- Empathy and accountability – They balance support with challenge.
If you’re working with an online coaching platform, be sure it allows you to match with coaches based on communication style, industry focus, and values – not just availability.
How to Prepare for Your First 90 Days of Coaching
Want to make the most of your investment? Here’s how to show up powerfully:
- Come with curiosity, not just expectations. The more open you are, the more you’ll gain.
- Track your progress. Keep a journal or digital log of what you’re trying, tweaking, and learning.
- Be honest. Coaching only works when you’re real about your fears and frustrations.
- Stay consistent. Treat coaching like a commitment, not a casual conversation.
- Celebrate the small wins. Progress builds when you acknowledge every step forward.
Is Coaching Worth It in the First 90 Days?
If you’re expecting instant results with zero effort, coaching may disappoint. But if you’re ready to grow – with guidance, feedback, and support – the first 90 days can be transformative.
Here’s the truth: most entrepreneurs know what they should do. But knowing and doing are two different things. A business coach bridges that gap – by helping you focus, execute, and evolve.
Final Thoughts: Your Growth Starts With One Conversation
Starting with a business coach for entrepreneurs isn’t about having everything figured out – it’s about being ready to grow. The first 90 days are just the beginning of a partnership designed to help you lead better, work smarter, and build a business that reflects your values and vision.
You don’t need to go it alone. Your next breakthrough could be one coaching session away.
Looking to connect with a coach who understands your path? Get matched with a trusted, experienced coach who meets you where you are – and helps you get where you’re going.
Related Reads:
- How Entrepreneur Coaching Builds Resilient Business Leaders
- Turning Vision Into Measurable Results: Entrepreneur Coaching Essentials
- The Real Cost of Waiting: Why Career Coaches Near Me Are Worth the Investment Now
Sources:
- International Coaching Federation. (2023). Global Coaching Study.
- Harvard Business Review. (2021). What Can Coaches Do for You?
- Forbes. (2022). The ROI of Coaching for Entrepreneurs.