Hi Reader,

You've said it out loud, or at least thought it on a Wednesday afternoon:

"Why do I have to spell out every single step?"

And then, quieter, right behind it:

"What am I doing wrong?"

Here's what I want to offer you today: that second question is the right one to ask, and the answer is better news than it feels like. Most of the time, what looks like an initiative problem on your team is actually a clarity gap in your handoff. And a clarity gap is something you can fix — this week — without hiring differently or lowering a single expectation.

That's the good news I want you to sit with. This isn't a character flaw in your team. It's not a sign you hired wrong. It's a gap in what got said out loud at the handoff, and that gap is yours to close.

I see this in almost every nonprofit I work with. A leader hands off a project, moves on to the next fire, and comes back a week later to find the work stalled, half-finished, or going in a direction they never intended. The instinct is to ask, "Why didn't they just take initiative?"

The better question is, "What did I assume they already knew?"

Years ago, when I was still leading programs inside a nonprofit, I handed a program outcomes measures project off to a program leader I'll call Jamie.

I told Jamie the name of the project. I told Jamie when it was due. I told Jamie I trusted them to run with it.

Two weeks later, Jamie came back with something I couldn't use.

It wasn't bad work. It was thoughtful, detailed, well-organized. It just wasn't the project I had in my head.

My first reaction, the one I'm not proud of, was frustration. Why didn't Jamie ask more questions? Why didn't Jamie check in sooner?

Then I took an honest look at what I had actually said at the handoff.

Here's what I realized: I had given Jamie the name of the project and the deadline, and almost nothing else. I hadn't said why this work mattered or what outcome it was actually supposed to produce. I hadn't said what done looked like versus draft. I hadn't said which resources to use or which decisions were Jamie's to make. And I hadn't built in a check-in early enough to catch the drift before it became two weeks of rework.

Jamie hadn't failed to take initiative. Jamie had taken initiative — pointed at a destination I never actually named.

So the most useful leadership question that week wasn't "Why won't my team take more initiative?" It was "What did I not say clearly enough at the handoff?", and once I asked it that way, I knew exactly what to do differently.

After that project, I started paying attention to what I was leaving unsaid. Over time, it settled into four things that belong in every real handoff. I think of them in a simple order: Why, What, How, When.

Start with why. The outcome. The North Star. Why this work matters and what success actually looks like. This is the one most of us skip, because we already know it in our heads, and we forget that our team members are only hearing the piece we say out loud.

Then what. The deliverables, the milestones, and what counts as "done" versus "draft." Specific enough that your team member could describe it back to you without having to guess.

Then how. The guardrails and the space inside them. Which resources and tools to use, what's non-negotiable, what they have flexibility on, which decisions are theirs, and when to escalate. This is where you get to build judgment, not just compliance, and for a lot of us, that's the whole job. You're not trying to get one task done right. You're trying to grow someone who gets the next ten right without you.

And when. This is the one I'd underline. Not just the deadline — the first check-in. Set it early, early enough that you can course-correct before the drift becomes two weeks of someone's work. Most of us set the deadline and skip the check-in, and then we're surprised by what shows up. The early check-in is the single cheapest thing on this list and it saves the most. If you take only one thing from this email, take that.

None of this takes long. A few extra minutes at the end of a handoff conversation. But those few minutes save you days of rework, and they change how capable your team gets to feel, because they finally have enough information to actually run.

One thing I've learned to watch: the people who most need me to say the why out loud are often the least likely to ask for it. The newer staff member, the person who isn't in my informal loop, the one who doesn't yet feel safe saying "wait, what do you actually mean?" — they're the ones a vague handoff fails first. The confident, well-networked people on your team will chase you down for clarity. Everyone else just quietly guesses. So saying the why out loud isn't only good communication. It's how you make sure the people with the least access to the unspoken context aren't the ones set up to miss.

And if you're further along in your career, this doesn't get easier — it gets more consequential. The more senior you are, the more context lives only in your head, the bigger the gap between what you know and what you say, and the more expensive the rework when a handoff drifts. The clarity habit matters more the higher you go, not less.

The next project I handed Jamie, I walked through those four things out loud before we wrapped the meeting. Not as a checklist. As a conversation.

"Here's the outcome we're aiming for. Here's what done looks like. Here's what you can decide without me. Here's when I'd like a quick check-in."

And then, instead of ending with the usual "Any questions?", I tried something different: "In one sentence, what's the why as you understand it?"

Jamie paused, thought for a beat, and said it back to me. In a sentence that told me we were finally looking at the same North Star.

Jamie came back on that project with exactly what I needed, and with two ideas I hadn't thought of.

That wasn't a personality change. Jamie didn't become more proactive overnight. Jamie finally had enough clarity to lead.

So here's your move for this week:

Look at your calendar for the next seven days. Find one handoff coming up, a project, a task, a decision you're about to pass off to someone on your team.

Before the conversation ends, run through the four things out loud, and set that early check-in. Then, instead of asking "Any questions?", try asking "In one sentence, what's the why as you understand it?"

Then hit reply and tell me what shifted. I read every message personally, and I'd love to hear what you noticed.

Steadier handoffs, stronger teams,

Sheila

P.S. I turned those four things — and a few better replacements for “Any questions?” — into a one-page Delegation Clarity Card I keep open during handoff conversations. [Grab it here] (it’s free)

P.P.S. You'll notice a new name on this newsletter; it's now the Confidare Leadership Newsletter. Same practical, immediately usable insights that fit your real constraints; just a name that better reflects where we're headed.​
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