How to Choose the Right Business Advisor: A Practical Guide for Business Owners

by Jean-Eric Plamondon | 28 Apr, 2025 | High Performing Team, Management Operating System, Scalable Business Model, Streamlined Processes

The short answer: Choosing the right business advisor is about finding the right fit for your company. Weigh six things: alignment with your business stage and size, customization versus cookie-cutter approaches, the breadth and depth of their services, real-world business experience, relevant industry experience, and a structured, proven approach. Then ask direct questions to see whether their style, expertise and offerings match what your business needs.

As a business owner, there often comes a point where working harder just isn’t enough.

Maybe you’re feeling stuck in daily operations, unable to grow (or unable to handle new growth!), or starting to think seriously about your exit strategy.

That’s when many owners start considering working with a business advisor.

But choosing the right advisor is a critical decision. The options can feel overwhelming – and it can be hard to find the right mix of expertise and experience.

Back when I was running multiple companies, I grew increasingly frustrated with the coaches, consultants, and advisors I hired.

I didn’t have time or patience for yet another exercise or report that didn’t apply to my business, or a business-in-a-box toolkit/methodology that was preached to every client, regardless of their industry, stage, or unique constraints.

Each of my businesses had different challenges—some industry-specific, others tied to the business model, and many driven by shifting internal constraints.

Too often, I found myself explaining basic nuances to my advisors—accountants, lawyers, coaches, consultants, trainers, entrepreneur peer groups—just to show why a potentially great idea that may have worked for someone else didn’t quite apply to my situation.

So to save you from the same experience, I put together this guide to help you navigate the process.

What Is a Business Advisor?

At its core, a business advisor is someone who helps you improve how your business operates.

Depending on their background, advisors might specialize in strategy, operations, growth planning, exit preparation, or leadership development.

Some advisors focus primarily on providing advice and frameworks. Others go further — offering hands-on help with things like software setup, team training, and project management to ensure real change happens.

Tip: Before hiring an advisor, consider what level of support you actually need: strategic guidance only, or strategy combined with implementation help.

What Should You Consider When Choosing the Right Business Advisor?

1. Alignment with Your Business Stage and Size

Different businesses have different needs.

Startups may need help developing a go-to-market strategy or securing early customers.

Established companies face a longer horizon and are often up against more complex operational challenges.

If you already have a functioning business but want it to run better, make sure you choose an advisor who has direct experience with companies like yours.

Tip: Ask potential advisors what kinds of businesses they typically work with — both by industry and company size.

A key question to ask: What industries and sizes of companies have you worked with, and what role(s) and involvement did you have within those engagements?

2. Customization vs. Cookie-Cutter Approaches

Some business advisors follow fixed systems (such as EOS or Scaling Up) that work well for certain companies but can be too bureaucratic “administratively heavy” for small companies with under-developed systems, or rigid for businesses with more complex operations. And in many cases, the systems are theoretically good – but the company isn’t ready for them because they lack the underpinnings to support them.

If your business is unique (and most are) you may be better served by an advisor who tailors the approach to your goals, your industry, and the realities and nuances of your daily operations.

For example, coordinating multiple job sites, field services, 3rd-party trades, and mobile teams requires a level of operational design that cookie-cutter corporate management systems might not fully address.

Tip: Look for an advisor who brings a structured methodology but tailors it based on your specific needs.

A key question to ask: Where do you draw your methodology and approaches from, and how have you come to learn and refine them?

3. Breadth and Depth of Services

Another key consideration is what kind of support the advisor actually provides.

• Strategic advisors help with planning, goal setting, identifying market opportunities, refining your business model, etc.
• Operational advisors take it further, helping implement management systems, software solutions, performance metrics, and team structures – ultimately driving accountability.

Some advisors focus exclusively on advice, leaving execution up to you.

Others, like GrowthStrategy, offer training, systems setup, and project management to bridge the gap between good ideas and real-world implementation and results.

Tip: If you want faster, smoother changes, look for an advisor who can help with both strategy and hands-on execution. What looks and sounds great on paper doesn’t always translate to the everyday nuances of your business.

A key question to ask: What is your experience in directly implementing any of the strategies you recommend with a team?

4. Real World Business Experience

There’s no substitute for hands-on, real-world experience.

An advisor who has owned and operated multiple companies — in different industries and through different stages of growth — brings a deeper, more adaptable perspective.

They’ve seen what works and (maybe more importantly) what doesn’t.

This kind of experience allows them to offer practical solutions grounded in operational reality, not just theory.

It also means they can draw on a broader range of examples and ideas, tailoring recommendations to what actually fits your business and its current stage.

Tip: Look for someone who’s lived through the ups and downs of business firsthand — ideally in more than one company, industry, and business stage (from startup to exit.)

A key question to ask: Have you ever had to pull money out of your pocket to make payroll by the end of the month?

5. Relevant Industry Experience

Experience matters. But relevant experience matters even more.

If you’re running a construction business, a trades company, or a field-service operation, your challenges are different from those of a tech startup, a retail shop, or professional services agency. Each industry and business model has its nuances in addition to the unique challenges that it faces at its current stage.

You want an advisor who understands the complexities of:

• Dispatching and managing field crews (especially those who are “great on the tools” and don’t want to hear about organizational MBA theory)
• Scheduling and coordinating mobile operations around other disorganized trades
• Managing real-time project costs (i.e. inventory, purchasing, change orders, and overhead allocation, to name a few)
• Implementing systems that work in an environment where work happens outside the office

Tip: Ask prospective advisors for examples of businesses similar to yours that they’ve helped.

A key question to ask: What experience do you have with businesses like ours? What challenges have you overcome? What challenges do you foresee?

6. A Structured, Proven Approach

While customization is important, a good advisor should still have a clear framework that guides their work.

At GrowthStrategy, our framework is based on these key pillars:

• Choosing the right business model for growth or exit
• Setting clear metrics and KPIs
• Implementing a management operating system (to run the business day-to-day, so the owners don’t have to)
• Designing and integrating the right software and automation
• Building a high-performance leadership team (and an environment that allows them to thrive)
• Streamlining and documenting processes for efficiency and consistency

Tip: Ask them to walk you through the steps they typically follow when helping a business like yours.

What Outcomes Should You Expect from the Right Business Advisor?

While every business is unique, the right advisor should help you achieve clear, tangible outcomes:

• Freeing Up the Owner’s Time:
  Building systems and training teams so that you’re not needed in every decision, every day.
• Growth Readiness:
  Structuring your business to scale up — whether that means more crews, more customers, or growth without needing to hire more office/admin staff.
• Exit Readiness:
  Making your business sellable, or enabling you to step back while keeping strong operations running smoothly.
• Operational Improvements:
  • Integrated systems for smoother operations
  • Real-time reporting for better decision-making
  • High-performing teams with clear accountability
  • Streamlined, repeatable workflows that remove bottlenecks

Questions to Ask Before Hiring a Business Advisor

• What types of businesses do you specialize in — in terms of industry and size — and what role(s) and involvement did you have within those engagements?
• Do you offer implementation support? If so, what would that implementation support look like? (If this is important to you, make sure that the advisor isn’t only offering strategic advice or coaching as their form of implementation support.)
• How do you tailor your process to different types of businesses?
• What typical outcomes have you helped clients achieve?
• How do you measure success during an engagement?
• How long does a typical advisory engagement last?
• What does the engagement look like? Advisory only? Workshops and presentations? Working hands-on with your team? Surveys?
• How much time will we spend together? Will you meet only with me? Or will you meet with my team as well?
• Where do you draw your methodology and approaches from, and how have you come to learn and refine them?
• What is your experience in directly implementing any of the strategies you recommend with a team?
• Have you ever had to pull money out of your pocket to make payroll by the end of the month?
• What experience do you have with businesses like ours? What challenges have you overcome? What challenges do you foresee?
• Can you share examples of businesses similar to mine that you’ve helped?
• Can you walk me through the steps you typically follow when working with a business like mine?

Asking these questions can help you quickly identify whether an advisor’s style, expertise, and offerings match what your business truly needs.

Choosing a business advisor isn’t about finding the most popular name or the flashiest promises.

It’s about finding the right fit for your company. Look for someone who understands your world, has the experience to guide you, and has a proven track record of fixing the problems you are experiencing.

By taking the time to assess your needs, asking the right questions, and choosing someone who brings both strategy and hands-on support, you can position your business for greater freedom, sustainable growth, and the option to exit when you’re ready for your next adventure.

Common questions

What does a business advisor do?

At its core, a business advisor helps you improve how your business operates. Depending on their background, they might specialize in strategy, operations, growth planning, exit preparation or leadership development. Some focus on advice and frameworks, while others offer hands-on help with software setup, team training and project management.

Should I hire an advisor who uses a fixed system like EOS or Scaling Up?

It depends on your business. Fixed systems work well for certain companies, but they can be administratively heavy for small companies with under-developed systems, or rigid for businesses with more complex operations. If your business is unique, you may be better served by an advisor who tailors the approach to your goals, your industry and your daily operations.

Why does real-world business experience matter in an advisor?

An advisor who has owned and operated multiple companies, in different industries and through different stages of growth, has seen what works and what doesn’t. That experience lets them offer practical solutions grounded in operational reality, and tailor recommendations to what fits your business and its current stage.

What questions should I ask before hiring a business advisor?

Ask what types of businesses they specialize in by industry and size, and what role they had in those engagements. Ask whether they offer implementation support and what it would look like, and how they tailor their process to different types of businesses. It also helps to ask about their experience directly implementing the strategies they recommend with a team, and to have them walk you through the steps they typically follow.