Getting started is often the hardest part.
Whether you’re a founder, director, or simply someone at a career crossroads, creating a plan can feel daunting, especially when the path ahead is full of unknowns. But a good plan doesn’t need to be perfect. It just needs to begin. And it begins with asking the right questions.
I’ve created this set of reflective prompts to help you think clearly about where you are now, and where you want to go. It’s not a full diagnostic or a strategy tool. It’s a practical, human starting point. A moment to pause, look inward and outward, and begin building something that’s rooted in what matters to you.
You don’t need to answer every question perfectly. You don’t need to know all the answers yet. But by giving yourself this space to reflect, you’ll begin to unlock insight, clarity and direction, and from there, a meaningful plan can emerge.
Start With Reflection
The following questions are designed to help you explore your business (or career) from multiple angles, from your motivations and mindset, to strategy, finance, people and performance. You might want to complete a mini SWOT and PESTLE as a first step, or jump straight into the questions. Either route is valid.
If you need support, invite trusted colleagues or advisors into the process. Many of these questions work beautifully in conversation.
Key Building Blocks
Before you begin, consider watching Simon Sinek’s Start With Why TED Talk, or exploring your own strengths using a free tool like VIA (www.viacharacter.org). These are useful companions to this work, they’ll help you understand what drives you and how you show up in your business.
Then, start exploring the following prompts:
- What are the main strengths, weaknesses, opportunities and threats facing your business right now?
- What external factors (political, economic, social, tech, legal, environmental) are shaping your landscape?
- What motivates you to run this business? How strong is your emotional connection to it?
- How confident are you in the business’s financial performance, and do you understand the key numbers?
- What keeps you up at night?
- What are the most critical people or skills gaps, and how are they helping or hindering progress?
- Which systems or processes feel clunky, outdated or holding you back?
- Who are your ideal customers, and how well do you know them?
- How do you compare to your competitors, and what could you learn from them?
- What sales and marketing plans do you have in place? Are they working?
- Where could AI have an impact, positive or otherwise, on your business model?
- What constraints are you working under, time, money, mindset, structure?
- What would someone change if they bought your business tomorrow?
- What do you want this plan to achieve, for you, your team, your customers?
- What are your personal or leadership development goals?
And most importantly: What comes up for you as you read these?
You Don’t Need All the Answers Yet
This is a starting point, a catalyst, not a conclusion. You may finish this exercise with a clearer vision, or you may just feel a little more grounded. Either way, you’re moving forward.
The truth is, no one knows your business or your motivations better than you do. I always assume that the people I work with are more capable than they realise. That includes you.
With the right questions, and the right support, you can create a plan that isn’t just strategic, but deeply aligned with what you care about.
Ready to Begin?
Download a template. Block an hour in your diary. Call a friend or advisor you trust. Start shaping your plan, not because you should, but because you want to lead with clarity and purpose.
If you’d like a guide through the process, or someone to hold the space while you reflect, I’d be happy to support you.
“Penny brings calm, clarity and challenge. I left our session not just with a plan, but with confidence in where I was heading and why.”
— Business Owner, Retail Sector
