It’s remarkable how many of my founders believe in telepathy. They assume truncated messages in Slack and offhand comments in meetings are somehow enough to produce well-executed plans.
Take a room of 100 CEOs and ask: “How many of you have recently had someone deliver a project that looked nothing like what you wanted?”
I’ve run this exercise. More than two-thirds raise their hands every time.
Then they remember the specific failure, and their hands go from being raised to rubbing their temples in anguish.
There are abilities we’re born with. Our vocal cords make sounds. Our legs propel us forward. Our opposable thumbs grip, and our ears hear. Delegating well is not innate. But like all CEO skills, it can be learned.
Expectations Are Evil
What went wrong in that room full of raised hands? Not a failure of effort or talent. An expectation was assumed where a clear agreement should have been reached. As the leader, that gap is yours to close. If you find yourself starting a sentence with “I thought you…,” you messed up.
A clear agreement is different. A clear agreement means both parties willingly say yes to something being done in a specific way, by a specific time, by a specific person, for a specific reason.
Instead of:
“Can you get that project done this week?“
Try:
“Can you provide the fully QA’d report, already double-checked by the finance team, by no later than 6 p.m. on Friday? I need it in time to include in the board package I’m distributing Monday morning at 9 a.m.“
Think that’s overkill?
The Alternative Is Worse
Consider the alternative. If I told you telepathy was a bad way to distribute work and allocate resources to important projects, you’d laugh. But leaving all the details inside your own head while expecting someone else to execute them correctly? You might as well try waving a magic wand..
How many of you are regularly nervous about whether something you’ve handed off will get done right?
That anxiety has a source. And it has a cure.
Worry Transfer
We call it worry transfer: handing something off so completely that you can remove it from your anxious mind. It has been fully transferred to another person. You can let go of it.
When someone says they’re bad at delegating, it usually comes from one of two places: 1) They have trouble trusting others, or 2) They’re bad at communicating. Or both.
Which are you?
To delegate effectively, you have to reach a clear agreement with your direct report. No expectations of telepathy. Your employees cannot read your mind, and you cannot read theirs. For any given project, a clear agreement means every one of the following questions is answered.
The Five Questions for a Clear Agreement
1. Why does the work need to be done? (Manager’s responsibility)
Context is not optional. An employee who understands why a task matters will make better judgment calls along the way and flag problems you haven’t thought of yet. Skip this, and you get compliant execution with no ownership.
2. What is the definition of “done?” (Manager’s responsibility)
The most skipped question. What you picture when you say “done” and what your employee pictures are almost never the same thing. Be specific. Draft quality, review stage, format, audience—define everything before the work starts, not after it lands on your desk wrong.
3. What is the work to be done? (First draft comes from the employee)
This one flips the script. Ask your employee to describe back what they’re going to do before they do it. It surfaces misalignment immediately, when it’s cheap to fix, rather than at delivery, when it isn’t. If their plan doesn’t match your expectations, you learn that in the meeting, not a week later.
4. By when does it need to be done? (Mutual agreement)
A deadline that only exists in your head is a wish. A deadline both parties have agreed to is a commitment. Get a specific date and time. “End of quarter” is not a deadline.
5. By whom is it to be done? (Mutual agreement)
More relevant than it sounds. Work handed to one person often gets quietly redistributed. Know who is accountable. If the answer is “the team,” the answer is no one.
Your people are your leverage. They let you focus on the most important parts of the business planning, fundraising, communications. But that focus is ruined when you’re constantly concerned with execution.
Will your people do the work the company needs, when it’s needed, and how it’s needed? Living with that anxiety is a choice, not a given.
Delegate the right way. Get away from expectations.
Your team is not psychic, and neither are you. Stop pretending you are.