Delegation as Experiment: From Doing to Multiplying
When you launched your company, or were initially building a team, doing it all wasn’t a flaw — it was survival. You wore every hat: ran every project, product, sales, marketing, hiring. That scrappy generalist energy got you off the ground.
But here’s the hard truth: the habits that fueled your early wins are the same habits that will stall your growth. Every hour you spend doing is an hour your company or your influence stays small.
The real inflection point? Learning that your job is no longer to do everything yourself — it’s to multiply what your team can do without you.
Why Founders Struggle With Delegation
I found myself in a conversation just two days ago with a former colleague who is now CRO for a high growth SaaS survey startup. He has worked at several startups, various stages and with very different founders and founding teams. In sharing each of our experiences, we both landed on delegation certainly being one of the most challenging for founders. for. Why?
Founders resist delegation for reasons that are as psychological as they are practical:
Identity: “I prove my value by doing.”
Control: “No one else will do it as well as I can.”
Fear: “What if it fails and I’m still responsible?”
Speed bias: “It’ll be faster if I just do it myself.”
But every one of these beliefs comes with a hidden cost: bottlenecks, slower execution, team disengagement, and founder burnout.
What the Research Says
Studies on entrepreneurial growth repeatedly highlight delegation as a critical inflection point. A large analysis of new ventures shows that firms whose founders fail to professionalize — hiring specialists, creating systems, and letting go of control — plateau or collapse earlier than those that do.
Leadership research also shows that empowering leadership behaviors — giving autonomy, clarifying ownership, providing coaching — are linked to higher team performance and engagement.
In short: delegation isn’t just about efficiency. It’s about creating conditions for your company to scale beyond your personal bandwidth.
Delegation as an Experiment
Instead of seeing delegation as a one-time “leap of faith,” treat it as a series of experiments in letting go.
Hypothesis: “If I delegate X, the team will complete it at Y level of quality within Z timeframe.”
Test: Hand off the task with clear ownership, resources, and outcomes.
Measure: Evaluate the process and results together — not as judgment, but as learning.
Framing delegation this way reduces the fear of failure and reframes it as a normal leader evolution.
Three Tools to Try
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Think of delegation as rungs on a ladder:
Level 1: “Do exactly as I say.”
Level 2: “Bring me options, I’ll decide.”
Level 3: “Make the decision, inform me.”
Level 4: “Own it completely — I’ll ask if I need to know.”
Too many leaders and founders hover at Level 1 or 2. True scale requires Level 3 and 4. This is rooted in trust and empowerment.
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Don’t you just love a start-stop-continue! List your weekly tasks under three headings:
Stop: Work that no longer belongs to you.
Start: Work you should be doing (vision, fundraising, executive hiring).
Continue: Work that only you can do right now.
This forces you to see where you’re still clinging to tasks that don’t fit your role.
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Ask:
What’s working?
What’s blocking you?
What decision would you make next?
This builds confidence and skills in your team while reducing your urge to step back in.
The Hidden Costs of Not Delegating
When you resist delegation:
Growth slows — you become the bottleneck.
Teams disengage — people feel like task-runners, not owners.
You burn out — the workload never matches your capacity.
And here’s the paradox: by doing everything yourself to “protect quality,” you often lower overall quality because things slip through cracks.
The Lab Experiment: Delegate One Thing
Now , it’s time to step into your lab. Here’s your challenge.
Objective: Practice delegation as a low-stakes experiment.
Choose a Task: Pick one task you currently own that someone else could realistically handle.
Pick the Person: Identify who is best positioned to own it.
Frame the Experiment: Write the hypothesis: “If I delegate [task] to [person], then [expected outcome].” — remember if-then planning to help with decisions?
Set Expectations: Define what success looks like, and when you’ll check in.
Debrief: After completion, reflect: Did it meet expectations? What did you learn about letting go?
Reflection Prompt: What fear came up as you handed this off — and what actually happened?
Closing Thought
Delegation is not about doing less work. It’s about doing the right work.
Your company doesn’t need you to be its best generalist anymore. It needs you to become the leader who multiplies others’ impact.