Issue #25 & June 22, 2026
Happy Monday!
A few weeks ago at our company retreat, Steph Llano led one of my favorite discussions of the entire event.
There was one idea that sparked a ton of discussion and it’s the idea that we all have to work to get on the same page, not just the person delegating.
I asked Steph to share her perspective with all of you. I’ll let her take it from here!
Clarity is co-owned.
Not the leader’s job. Not the person handing off the work’s job. Everyone’s job.
The small assumptions that cost us
Think about how many times in a given week you hear something like:
“Can you clean this up?”
“Follow up with the client.”
“Make sure this is ready.”
Every single one of those requests is technically understandable. And every single one of them leaves a massive amount of room for interpretation.
What does “clean this up” mean? A quick proof or a deep dive? What does “ready” mean? Ready for internal review, or ready to send to the client, or ready with prior year comparison included?
When we assume we understood the ask, and the other person assumes they communicated it clearly, that’s where rework is born. That’s where missed deadlines live. That’s where “I thought YOU were handling that” comes from.
Misalignment doesn’t always look like conflict. A lot of the time it just looks like drag.
Both sides own it
Here’s the part that tends to shift something for people.
The person giving the work owns communicating expectations clearly. But the person receiving the work owns asking questions, naming their assumptions, and confirming alignment before they run with it.
Neither side gets a pass!
Most of us were never really taught to ask clarifying questions when we receive work. It can feel like it slows things down, or like it signals you don’t know what you’re doing. So instead, we make an educated guess and hope for the best.
But one question asked upfront saves hours of rework on the back end. Every time.
When you’re giving work, try these questions
The first set of questions puts the burden on the other person to speak up. The second set makes it easy for them to.
Instead of asking… | Try asking… |
Does that make sense? | What can I make more clear? |
Do you have any questions? | What’s one question you have about this? |
Is that okay? | What concerns or roadblocks do you see? |
Can you handle this? | What do you need to move this forward? |
When you’re receiving work, ask these questions
This is the one that really landed with Tailor’s team. Because most people never think about the receiver having just as much responsibility to ask.
We actually had everyone pick two of these to commit to using. Try it!
Category | Questions to ask |
Clarify the outcome | What does done look like? What would make this successful? |
Clarify ownership | Who owns the next step? What should I handle vs. bring back? |
Clarify priority | Where does this fall compared to my other priorities? What should I deprioritize if this becomes urgent? |
Clarify communication | When do you want an update? What would be a reason to flag something early? |
Clarity becomes culture
None of this requires a big initiative or a new process.
It just requires a habit. Asking the question before you start instead of after you’re stuck. Defining what “done” looks like before anyone takes a single step. Flagging the roadblock before it becomes the emergency.
When a team does that consistently, clarity stops being a conversation you have to have. It just becomes how you work!
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Steal this The Takeaways • Stop asking “Does that make sense?” and start asking “What questions do you have?” • Define what “ready” means before work begins. • Treat clarity as a shared responsibility, not a management responsibility. Most accountability problems are actually clarity problems. |
Question of the week
How often do you define what “done” looks like before work begins?
Steph nails it with this one!
One thing I’ve learned as we’ve grown:
Having good clarity scales. Assumptions don’t.
When you’re a team of one or two people, everyone can read each other’s minds.
At ten people, that falls apart pretty fast.
The more a company grows, the more important it becomes to define expectations, ask questions, and make sure everyone is solving the same problem.
That’s why this conversation resonated so much at our retreat.
Have a fantastic week!
- Tailor
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