What’s the number-one thing we’ve seen holding small businesses back?
A weak or non-existent senior team and an owner doing too much.
There are lots of reasons why a business owner can’t (or won’t!) delegate. Some reasons are practical: there simply isn’t enough money to hire someone, even part-time. That’s a real structural constraint, and while solvable, it’s a major barrier.
But the tougher reason is psychological. Many owners don’t actually want to let go of the tasks they’ve always handled. Or they have tried delegating, and it didn’t go well. A classic response is:
“I tried handing it off, but they didn’t do it right. It was just faster to do it myself.”
This mindset keeps owners trapped. On one side, you have limited resources; on the other, limited trust in the delegation process. Let’s look at each challenge and how to overcome it.
Lack of resources
An owner who wants to get out from under a set of tasks has to squeeze enough resources out of the business to make room for an additional hire. Those resources might come from cost savings, customer revenues, external capital or government programs. In the early days, belief in the business and a little visionary zeal can help an owner attract people at less than market rates, but ultimately great people cost money.
One option we’re trying to make easier is hiring fractional executives—senior part-time leaders who can take on well-defined scopes of work without the cost of a full-time salary.
Fractional finance leadership has been around for decades (fractional CFOs are now common), and we’re seeing the same model work well for marketing, operations, and other specialized areas. For many small businesses, this is the fastest path to rapid improvement.
That said, there’s one area where we don’t recommend hiring fractionally: sales.
You can absolutely hire advisory help: someone to clarify your sales process, messaging, funnels, scripts, and training. But sales is fundamentally hands-on, and the knowledge gained by doing it day-to-day needs to stay inside the business. In the early years, the owner should remain the primary salesperson.
“It’s quicker to do it myself”
This mindset is understandable but limiting.
Yes, it will take longer this week to train someone properly. Yes, they will make mistakes. Yes, you may feel frustrated watching someone do something slower or differently than you would. But the long-term road to scale goes through delegation. It’s unavoidable.
Here are a few principles to make delegation more successful:
Start with values
You can’t delegate important work to someone who doesn’t share the values you consider critical. Communicate these through your own actions plus a little explanation, or recognition when others do the right thing. If you’re not around to make a crucial decision, you want the person making it to start by weighing the same things you would.
Give them some context
We’re not asking for a mind-meld or 400-page dissertation on the company history. But a little high-level business perspective can go a long way: “Most of our revenue today comes from repeat customers, so we really try to address customer issues the same day…”
Define a clear scope
You can’t hand off something vague like “Run marketing” or “Handle operations.”
But you can hand off:
- A specific part of a process
- A well-bounded operational role
- Ownership of repeatable tasks
- A defined slice of the sales cycle
Delegation works best when the scope is concrete and measurable.
Expect (and allow) early discomfort
It is completely normal for the first few weeks to include:
- Mistakes
- Re-work
- Slower results
- Miscommunications
This is not failure. This is onboarding.
Use metrics to make the conversations objective
When expectations and success metrics are clear, performance conversations become less emotional. You and your employee (or fractional leader) can look together at:
- Output
- Throughput
- Quality
- Timeliness
- Revenue
- Whatever other ‘metrics that matter’ are critical for your business
In our experience, employees do better with one or two critical numbers to think about. Don’t ‘metrics them to death.’
Stick with it long enough for it to work
The real payoff comes once you’ve made the shift from the owner doing the work to owner managing the outcomes. Give it a minute.
And finally…
Let them make the call
If all decision-making runs though the boss, the business will seize up when it grows. When it’s in their span of control, encourage your people to make the decision and learn from the consequences.
Other things to consider
What should you delegate?
Before you hire, you can test what you should delegate by figuring out:
- What only you can do
- What someone else could do with training
- What someone else could do better than you
This helps you prioritize where to invest.
Apply the 70% rule
If someone can perform a task at about 70% of your level, delegate it.
They will grow into 100% over time, and you will free up your highest-value hours.
Build Standard Operating Procedures (SOPs) before you hire
Documented workflows make delegation faster and lower-risk. Examples:
- A 3-step checklist
- A short Loom video explaining the task
- A shared Google Doc with expected outcomes
- Templates or scripts
Your future hires will thank you.
Delegate outcomes, not tasks
Instead of “Send this email every Monday.”
Try “You own weekly customer communication. Here are the goals, guidelines, and measures of success.”
This creates ownership rather than task-following.
Hire for judgment, not just skill
Most delegation failures happen because the person isn’t able to make decisions when things don’t go as planned. Hiring for judgment—through scenario-based questions—is one of the best predictors of success. This is also where the first item on Values comes in.
Do regular check-ins
Weekly is a good place to start. A simple 20-minute meeting with three questions:
- What did you accomplish?
- What’s blocking you?
- What’s next?
This creates rhythm and reduces surprises.
If you have questions on fractional executives or on delegation in general, drop us a line at [email protected].