21 Questions to Ask Yourself to Grow Your Business — Your Way
Ready to grow your business, get unstuck, and create more freedom in your life? Start by asking yourself the right questions.
You started your business for a reason. Maybe you wanted financial independence, more control over your time, the freedom to pursue your ideas, or the opportunity to do work you love.
But somewhere along the way, the day-to-day demands of running a business can take over. You find yourself putting out fires, making every decision, managing every detail, and wondering how you’re supposed to grow when you barely have time to think.
Sound familiar?
You don't have to keep running your business this way. Growing a business that supports your goals and lifestyle starts with getting clear on what you want, understanding what's holding you back, identifying the support you need, and creating a plan to move forward.
As a strategic business advisor, I help business owners step back from the day-to-day, see the bigger picture, and make confident decisions that move them towards their vision.
To help you get started, I've put together 21 questions to help you grow your business your way, on your path.
Take your time with these questions. Write down your answers, use a journal, or simply reflect on them. If you don't know an answer right away, that's okay. Sometimes, asking the question is the first step towards finding the answer.
Step 1: Revisit Your Vision
Before you can build the business you want, you need to define what that business looks like. It's easy to get caught up in what other people are doing, what you think you should be doing, or what you've always done. But your business should be built around your vision, your priorities, and the life you want to live.
Start by asking yourself:
What is your long-term vision for your business and your life? Think about where you want to be in 5, 10, or even 20 years.
What would you be doing — and not doing — in your business and your personal life? Consider your responsibilities, daily schedule, and how you want to spend your time.
How much money would you be making, who would you be working with, and where would you be living? Why? Get specific about what success means to you and why it matters.
Think about what you really want, not what someone else expects of you.
Would you like to take more vacations? Spend more time with family? Build a team that allows you to step away from daily operations? Increase your income without working longer hours? Prepare your business for sale?
There is no single right answer. Your vision is personal to you.
Your takeaway: Write down your vision. Give yourself permission to think bigger and imagine what your business and life could look like if you had the right strategy and support in place.
Step 2: Identify Your Gaps
Now that you have a clearer idea of where you want to go, it's time to look at where you are today.
The difference between your current situation and your desired future is your gap. Identifying that gap helps you understand what needs to change.
Ask yourself:
What is the difference between where your business is today and where you want it to be?
What have you already tried to improve your situation? What worked, what didn't, and what did you learn?
What are the top three things holding you back from getting what you want? Consider time, money, staffing, systems, marketing, sales, or uncertainty about what to do next.
What changes do you need to make to achieve your goals? Think about the decisions, priorities, or ways of working that may need to change.
What are you willing to change? Growth often requires doing things differently, letting go of old habits, or making decisions that feel uncomfortable at first.
Be honest with yourself during this process. The goal isn't to criticize what you've done so far. It's to understand what's happening so you can make better decisions about what comes next.
Sometimes, the biggest obstacle isn't a lack of ideas or effort. It's being so close to the business that you can't see the bigger picture.
Your takeaway: Identify your biggest gaps and the changes that could make the greatest difference. You don't need to solve everything at once. Start by recognizing what needs your attention most.
Step 3: Identify the Support You Need
You don't have to do everything yourself to build a successful business.
In fact, trying to do everything yourself can become one of the biggest barriers to growth. The right people, systems, processes, and technology can help you create capacity, improve efficiency, and reduce your dependence on being involved in every decision.
Ask yourself:
What support do you need in terms of people, systems, processes, and technology? What would make running your business easier or more effective?
Who do you need to hire now? Identify the immediate skills or responsibilities that need additional support.
Who will you need to hire next? What are the top three positions you'd like to fill when you can afford to do so? Think about the team you'll need to support your future goals.
What responsibilities would you offload if you could? Consider the tasks that consume your time but don't require your unique expertise.
What systems and processes would allow your business to operate without you? Think about what needs to be documented, streamlined, automated, or delegated so you can step away when needed.
Can your business run without you? Why or why not? If you took a week off, would things continue smoothly, or would everything come to a standstill?
If you plan to sell your business, is it ready for sale? Would someone want to buy it, and why or why not? Consider how dependent the business is on you, the strength of your team, and the systems supporting its operations.
What technology do you need to support your business goals? Identify tools that could save time, improve communication, simplify operations, or help you make better decisions.
Do you have a budget and a plan to get the support you need? Determine what you can invest in now and what you'll need to plan for in the future.
You may not be able to hire everyone or implement every system immediately. That's okay. The point is to identify what you need, determine what matters most, and create a realistic path towards getting there.
Your takeaway: Make a list of the people, systems, processes, and technology that would help your business grow. Prioritize the support that will have the biggest impact on your goals.
Step 4: Turn Your Vision Into an Actionable Plan
A vision without action remains an idea. Once you've identified what you want, what's holding you back, and what support you need, it's time to bring everything together into a practical plan.
Your plan doesn't need to be complicated. It needs to help you make decisions, establish priorities, and take consistent action.
Ask yourself:
What are your main business objectives, and what specific results do you want to achieve? Identify the outcomes that matter most and the actions required to reach them.
What actions will you take immediately, in three months, one year, five years, and ten years? Break your goals into manageable steps, starting with what you can do now.
How will you prioritize your actions, get the support you need, and track your progress? Decide how you'll review your goals and progress daily, weekly, monthly, quarterly, and annually.
What does success look like, and how will you celebrate your achievements? Define how you'll know you're making progress, and make time to recognize your wins along the way.
Once you've answered these questions, bring your vision, gaps, support needs, and priorities together into one document. Use a spreadsheet, journal, or planning tool to keep your goals and actions organized.
Then, put your plan into motion.
Review your progress regularly. Adjust your approach when circumstances change. Ask for help when you need it. And remember to celebrate the milestones you achieve along the way.
Your takeaway: Choose one to three actions you can take now. You don't need to have every detail figured out before you begin. You need a clear direction and a willingness to move forward.
You Don't Have to Do It All
Growing a business shouldn't mean sacrificing the life you wanted it to create.
You can build a business that supports your lifestyle, increases your income, gives you more control over your time, and allows you to focus on the work you do best. But you may need to change course, make difficult decisions, or get support to make that happen.
This process is for you if:
You're juggling too many responsibilities and craving more time for what matters most.
You want a business that supports your life instead of running it.
You're ready to pursue financial growth, build a stronger team, and get the right support.
You're stuck in a rut and need help finding the right path forward.
You're ready to step into the role of business leader instead of being the person who has to do everything.
When we work together, we'll clarify your vision, identify what's holding you back, determine the support you need, and develop a practical action plan tailored to your goals.
You'll gain a clearer understanding of what to do next, who you may need to hire, what to prioritize, and how to move forward with confidence.
As a strategic business advisor, I help professionals, entrepreneurs, and business owners — including those in the trades — make informed decisions and create businesses that work for them.
Ready to Take the Next Step?
You don't need another year of spinning your wheels, second-guessing your decisions, or trying to figure everything out alone.
Let's identify what's holding your business back and determine what you can do about it.
Book a confidential call with me, and together we'll explore your biggest obstacles, clarify your next steps, and identify one to three actions you can take to start moving your business forward.
Let's build a business that supports your vision, your goals, and the life you want to live.
Janet Sawatsky
Strategic Business Advisor | Owner, 7 Point Trends Inc.
Calgary, Alberta, Canada
1-587-576-2755
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