How to know the best time to delegate
- Kelli Thompson

- Aug 18, 2025
- 3 min read
When I was in corporate as a trainer and leading training teams, one of the practices we held as a team before we launched a new training program widely was to do an initial run through with a “safe” audience. Usually this audience was hand-selected and they were excited to see a first pass and give helpful feedback.
There were a few things we could always count on: Presentation timing mistakes would be made. Activities would fall flat. Slides had typos we missed. Key learning points didn't stick. But we could also count on this: The low-stakes practice run taught us what we needed to change so we felt confident about the big launch.
Many leaders tell me they can’t delegate because people seem to make high-impact mistakes. This is true when we wait to delegate tasks when the stakes are high.
The key here is to start delegating when the stakes are low. We have a higher tolerance for making mistakes in low-stakes situations. For example, if your employee’s goal is to develop better presentation skills, try a low-stakes activity like asking them to lead the next staff meeting before a high-stakes one like conducting a client meeting.
Or, if they want to get better at influencing others, challenge them to get buy-in from a small team on using a new tool or work process before asking them to persuade your whole division to implement it.
Then, when they are called to the table when the stakes are high, they have confident repetitions under their belt.
🔥 Are you working on an activity or project that is no longer a development opportunity for you? Delegate it in a low-stakes way. Someone on your team is hoping for opportunities to grow, and these make perfect circumstances to do so. They build everyone's confidence and help you make the shift from high achiever to strategic leader.

PUT THIS IDEA INTO ACTION
In addition to delegating tasks and projects while the stakes are low, there are three practices to embrace to help you delegate like a pro: Clarity, Authority & Grace.
Clarity. Ensure you have been crystal clear about what is expected in the ask. What is/are the:
Purpose
People roles
Process steps
Performance outcomes
…that you expect?
Authority. When you delegate a meeting or leadership in a project, ensure that the other stakeholders know that you’ve crowned your team member as decision-maker, and they should go directly to that individual. The ownership and accountability of delegation is negated when everyone is still coming to you for the updates, decisions, and answers.
Grace. Grace doesn’t mean you tolerate poor effort or careless mistakes. Grace is offering kindness and accommodation in the face of someone not doing something exactly how you would do it. Giving grace is offering gentle yet direct feedback on how someone can improve their delivery in their own way, using their best talents, even if it’s not your way. Grace is essential, because if a leader doesn’t create a safe space for people to make earnest mistakes while learning the ropes, she will find herself with a team who is unwilling to try anything new.
Do This Next: Pick one low-stakes task to delegate at work or home. If you are worried about a mistake being made, think smaller. Mistakes are part of learning! If you want more help with when, how and what to delegate, check out my fall course!

Kelli Thompson is an award-winning author, keynote speaker, and executive coach who specializes in helping high achievers advance to influential leaders in their organizations. She is the author of the critically acclaimed book, Closing The Confidence Gap: Boost Your Peace, Your Potential & Your Paycheck.
Learn more about: Executive Coaching | Speaking & Training | Group Programs




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