Key takeaways
- Delegation is about getting more done and developing your staff
- Transition from “super-doer” to multiplier
- Decide what to delegate
- Delegate outcomes, not tasks
- Use levels of delegation explicitly
Once you reach a team of 5–20 people, “doing it all yourself” is no longer an option. The real question becomes:
How do I get results from other people without losing control or spending all day checking their work?
This is your bi-weekly SME Entrepreneurs Newsletter with more in-depth analysis.
Redefine your job: from “super‑doer” to “multiplier”
At 5–20 people, the most common failure pattern is this:
- The owner is still the best at sales/delivery/operations
- The team “helps,” but the owner is the bottleneck on anything important
- Everyone is busy, but growth feels stuck
Your role must shift from super‑doer to multiplier:
- Super‑doer: “How much can I get done?”
- Multiplier: “How much can I help the team get done without me?”
That means:
- Fewer tasks that you personally execute
- More time designing systems, setting priorities, clarifying decisions
- Coaching key people so they can have their own outcomes
If you don’t make this shift, the business size will flatline around your personal capacity.
Decide what to delegate using the Team Leverage Map
With a team, the question isn’t “what can I get rid of?” It’s “where is my time worth the most?”
Use this 2x2 thinking:
-High value / strategic + Only I can do
-High value / strategic + Someone else can do with support
-Low value / operational + Someone else can do
-Low value / unnecessary
Focus on your own time:
- Vision, strategy, key relationships, capital allocation
- 1:1s and coaching for your top 3–5 people
- Decisions that have long‑term impact and are hard to reverse
Aggressively delegate:
- Repeating operational work (reporting, scheduling, logistics)
- Day‑to‑day problem solving your managers should be handling
- Execution that someone on the team could own with clear outcomes
Delegate outcomes, not tasks
With a team of 5–20, you should not be delegating at a “checklist step” level for everything. Your high‑potential people need ownership.
The shift:
- From: “Do these 12 steps like this.”
- To: “Own this result. Here are the boundaries and resources. I’ll support you.”
Use this structure when delegating to key team members:
1. Outcome (what success looks like)
- “Reduce average response time to customer inquiries from 48 hours to under 12 hours within 60 days.”
2. Definition of done (clear, measurable)
- “We consistently hit that metric for 4 weeks in a row, and I’m not personally touching more than 5% of tickets.”
3. Constraints (time, budget, policy)
- “You have 10 hours a week for this for the next 2 months.”
- “You can adjust tools and templates, but don’t change pricing or refund policies without checking with me.”
4. Authority (what they can decide alone)
- “You can change inbox workflows, templates, and team schedules as needed, as long as you show me the plan first.”
5. Check‑ins (cadence & format)
- “We’ll do a 20‑minute weekly check‑in. Come with 3 numbers (volume, response time, satisfaction score) and top 3 issues.”
Use levels of delegation explicitly
To avoid micromanagement on one side and abdication on the other, be explicit about how much you’re delegating.
For team members in a 5–20-person business, use 3 clear levels:
1. Level 1: I decide, you execute.
- You: make the decision, set steps.
- Them: follow the plan, ask before changing anything meaningful.
Use when:
- The work is at high risk or new
- The person is still learning the domain
2. Level 2: You propose, I approve
- They analyse, come with a recommendation and plan.
- You approve or adjust.
Use when:
- You want to grow their judgment
- The impact is moderate, not business‑threatening
3. Level 3: You decide, keep me informed
- They own the decision and execution.
- You set a reporting rhythm and key metrics.
Use when:
- They’ve shown good judgment
- You trust them in that area of the business
Coach instead of fixing
One of the fastest ways to kill delegation is this pattern:
1. Team member brings you a half‑baked solution.
2. You get frustrated, take it back, and “do it right.”
3. They learn: “If I don’t nail it, the boss will just do it.”
To break that:
When someone comes to you with a problem, try this sequence:
1. “What have you already tried?”
Forces them to think before escalating.
2. “What options have you considered?”
Get them to generate at least 2–3 approaches.
3. “Which option would you pick, and why?”
You are building their judgment, not just solving the issue.
4. Then respond at the right level:
- Level 1: “Do X.” (for urgency/risk)
- Level 2: “I’d tweak your option like this; go ahead.”
- Level 3: “Your reasoning makes sense. Run with it. Tell me how it went.”
You’ll spend a bit more time now but massively less in the future.
At 5–20 people, your biggest leverage is no longer working harder. It’s building people and systems that work well without you.
If you delegate vague tasks, you’ll feel burned. If you delegate clear outcomes with the right level and rhythm, your team will develop real ownership, and your business can scale beyond your personal capacity. Start with one function and one key person. Get that right, then expand.
See you in two weeks for another edition of your SME Entrepreneurs Newsletter. May you always have the mindset of an entrepreneur.
Sajjad Hamid is an SME & Family Business Adviser who supports entrepreneurs in scaling their ventures. In his spare time in Trinidad and Tobago, he cultivates organic tropical fruits and vegetables, practising sustainable farming in his home garden.
He is the author of Build Your Legacy Business: Solopreneur To Family Business Hero. Sajjad is a Fellow of the Family Firm Institute. He writes a column titled Entreprenomics in the Business section of the Trinidad and Tobago Guardian. You can contact him at [email protected] or visit www.entrepreneurtnt.com.
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