As a business owner, you’ve worn every hat imaginable. You’ve been the salesperson, the accountant, the marketer, the customer service rep, and everything in between. Your hands-on involvement built your business from the ground up. But as your business grows, you start to notice that continuing to do everything yourself will become the very thing that limits your growth.
Changing from working in your business to leading your business is one of the most challenging shifts you’ll make as an entrepreneur. It requires letting go of control, trusting others with your vision, and redefining what success means for you.
But you don’t have to do it alone; we can help guide you through this change when it’s time to make it.
Why transitioning to leadership is challenging
There are a couple of key challenges that arise when you change from being a business owner to a leader. Let’s see if we can nail any of the challenges you might be feeling right at this moment.
1. In a founder’s trap
Often, since you started the business and you understand everything in and out, you feel as if you can do everything faster and better than anyone else. This belief keeps you buried in day-to-day operations rather than focusing on growth, strategy, and building a sustainable business. The trap is that your efficiency in execution becomes a ceiling for your business growth.
2. Feeling too much perfectionism
No one will care about your business the way you do, and that’s okay. But many business owners struggle to accept “good enough” when they’re accustomed to their own standards of excellence. You might redo work, constantly check in, or hover over your team, which undermines their confidence and your own capacity.
3. Hiring the wrong people or not hiring at all
Finding people who share your vision and values is difficult. Many business owners either hire too quickly out of desperation or delay hiring far too long, burning themselves out in the process. Others hire people just like themselves rather than complementary skill sets the business actually needs.
4. Revenue guilt
When you step back from work or direct revenue generation to focus on leadership, it can feel like you’re not contributing. You might feel guilty about “just managing” or struggle to justify your time when you’re not directly bringing in money. This mindset ignores the massive value of strategic leadership.
5. Lack of systems
Much of your business knowledge likely lives in your head. You know how things should be done because you’ve always done them. Without documented systems and processes, delegating becomes nearly impossible, and your team constantly needs to interrupt you for answers.
6. Isolation
The camaraderie of doing the work alongside others shifts when you become “the boss.” You might feel isolated or struggle with imposter syndrome, wondering if you’re really qualified to lead when you’re more comfortable executing. Your professional identity changes from “expert practitioner” to “business leader,” which can feel uncomfortable.
These feelings, while valid, don’t have to last forever. There are ways to work through them, so you can not only better your business, but also better yourself.
5 steps to transition into a leadership role
1. Acknowledge that you’re the bottleneck and it’s time to change
The hardest truth to accept is that your intimate involvement in every aspect of the business has become a constraint on growth. Your 40, 60, or 80 hours per week is a fixed limit and there’s no scaling.
So what can you do about it?
- Reflect on how much you’re giving
- Decide what needs to change
- Take action
Start by tracking your time for two weeks. Document everything you do and how long it takes. This exercise reveals where you’re spending time on $20/hour tasks when you should be focused on $1,000/hour strategic decisions. It’s confronting but necessary.
Make a firm commitment to step back, not because you’re lazy or don’t care, but because it’s what your business needs to reach the next level. Reframe this transition in your mind: you’re not becoming less involved; you’re becoming involved in the right ways. Leading your business is still serving your business, just differently.
2. Hire strategically and build your core team
When you know it’s time to change, the best step you can take is learning how to get the help you need. Begin by identifying which roles would have the biggest impact on freeing your time and growing the business. Is it an Accounts director? Social media creator? Often this isn’t the most senior hire, but rather the person who can take your most time-consuming operational tasks.
When building your team, look for people with complementary skills rather than mini-versions of you. If you’re creative and visionary but disorganised, hire someone who excels at systems and execution. If you’re great with clients but struggle with numbers, bring in someone financially minded. When hiring new people, prioritise cultural fit and value alignment alongside skills too. You need people who will care about quality and clients, even if they won’t care as intensely as you do. Remember to be explicit about your vision and values during the hiring process, and use scenarios to assess how they’d handle real situations in your business.
When it comes to hiring, don’t wait until you’re desperate and drowning. Hire when you’re at 75-80% capacity, so you have time to train new hires properly and allow new team members to succeed rather than being thrown into chaos. If they come in with no guidance or support, you may see high turnover rates.
3. Create systems and document everything
Often, the knowledge trapped in your head is preventing your business from scaling. When you become a leader, you need to mentor others to follow in your footsteps, not just do it all for them. It’s best to begin systematically, documenting how things are done, so others can work without constantly interrupting you. You can do this by starting with the tasks you do most frequently or that create the biggest bottleneck.
Here are some ways you can create systems right now:
- Checklists
- Templates
- Video tutorials
- Standard operating procedures
It’s best to organise your thoughts with tools like Notion, Google Docs, or Loom to make this process easier than ever for both you and the new hires. Don’t aim for perfection; get version one documented and refine it over time. You can always reorganise once the content is there.
A strategic way to do this is by writing out a business playbook that captures:
- Your client service standards and what quality looks like
- Sales and onboarding processes
- Communication and marketing templates and guidelines
- Problem-solving frameworks for common issues
- Your core values and how they translate to daily decisions
A business playbook filled with all this information will become your training manual for new hires, as well as a quality assurance tool and the foundation for consistency as you grow. It also forces you to clarify and standardise approaches that might have been instinctive or inconsistent.
4. Learn to delegate outcomes, not just tasks
Many business owners think they’re delegating when they’re actually just offloading tasks while maintaining control of every decision. True delegation means entrusting both the work and the thinking behind it.
How can you do this? Start with a delegation framework:
Level 1: Do this specific task exactly as I’ve shown you (for beginners)
Level 2: Research and recommend, but I’ll decide (building judgment)
Level 3: Decide and inform me (building autonomy)
Level 4: Act independently and update me periodically (full ownership)
Move people through these levels as they demonstrate capability. But don’t forget, it’s vital you clearly communicate which level you’re delegating at for each responsibility, and resist the urge to jump back in unless absolutely necessary. Accept that people will do things differently from you. If it achieves 80% of your result, let it go. Instead, use the extra time you’ve gained to work on activities that will move your business forward by more than the 20% difference.
When mistakes happen, and they will, treat them as investments in your team’s development rather than reasons to take the work back. Coach through problems instead of solving them yourself.
5. Shift your focus to vision, strategy, and growth
As a business owner-turned-leader, your unique value is in seeing the bigger picture that others can’t. You understand the market, the clients, the industry trends, and where opportunities lie. This strategic perspective is where you should invest your time.
You can do this best by blocking time in your calendar for strategic work:
- What new services, products, or markets should you explore?
- What relationships and partnerships would accelerate growth?
- What’s the next phase of team building and capability development?
- How can you strengthen your competitive position?
- Where should the business be in 1, 3, and 5 years?
Additionally, it’s important to get outside inspiration from how others are thinking, growing, and changing. Consider attending industry events, connecting with other business owners, or investing in your own learning through mentors or advisors. Your job is to stay ahead of the curve. Once you’re there, you can develop your leadership skills intentionally by reading books on leadership and scaling businesses, joining a business owners’ group, or working with a business coach.
Grow your capabilities as your business grows
You can be both the business owner and hands-off leader. It comes with time, patience, and practice, but it’s not impossible. Once you build a team, regularly meet with them, not just to check up on tasks, but to communicate vision, remove obstacles, coach through challenges, and lead them to company alignment. Your presence should energise and clarify them all, not micromanage. So, are you ready to find a place to settle down that’s geared towards growth?
Join a coworking space that values your trajectory, like Haven Workspaces. As a modern working community here in Canberra, we want to help entrepreneurs and small businesses reach their fullest potential. Whether you’re hiring your first team member or starting to become your own hands-off leader, we’re here to guide you in a space that inspires.
Join a coworking space that has it all. Check out what we offer at Haven Workspaces today!