“Why Don’t They Just Do What I Asked?” (And What Did I Miss?)

You’ve built a great team. You value their commitment, trust their capability, and enjoy working together. But there’s a frustrating puzzle you keep coming back to:

Why don’t things get done the way I expect them to?

If you've ever found yourself asking…

Why don’t they just do it?

Why am I chasing things up?

I’ve asked several times, I just don’t get it.

They’re great people... so why doesn’t the work land the way I need it to?

...you’re not alone. Many of the leaders I work with voice this kind of frustration. The outcome?

They end up quality-assuring everything.

Reworking tasks themselves.

Feeling exhausted, inefficient, and fed up.

And much of it is avoidable.

Where It Goes Wrong: Misunderstood Expectations

Brené Brown speaks powerfully to this in Dare to Lead, introducing the concept of “Paint Done.”

When delegating, leaders often assume their version of “done” is understood. But people interpret instructions based on their own context, assumptions, and experience.

Brown suggests that instead of saying “Create a presentation,” leaders can usefully describe exactly what done looks like:

What content should it include?

Who’s the audience?

What format, tone, or visual style is required?

When is it needed, and what does ‘good’ actually mean?

It’s a deceptively simple but powerful shift: make your expectations vivid, detailed, and clear. And invite your team to ask questions, not just nod and walk away.

Clarity Is a Leadership Skill

Delegation failures often come from leaders thinking they’ve been clear when in fact, they haven’t. Your team can’t meet unspoken expectations. And they won’t ask clarifying questions if the culture suggests they should already know.

Here’s where self-awareness comes in.

The Dunning-Kruger Effect: A Hidden Trap in Delegation

This well-researched cognitive bias offers insight into why delegation often falls flat:

The Team Member: Unaware of What They Don’t Know

Less experienced team members may genuinely believe they understand the task, even when they don’t. They might:

Miss key complexities.

Hesitate to ask questions (because they think they “should know”).

Deliver confidently… and miss the mark.

The Leader: Forgets What Others Don’t Know

Experienced leaders often underestimate how much context they’re holding. What’s obvious to you may be brand new to someone else.

You assume you’ve been clear.

You forget key distinctions aren’t universal.

You think you’re delegating well, but your version of “clear” needs translating.

Closing the Gap: Self-Aware Leaders Create Clarity

Great leaders don’t assume clarity, they check for it.

Pause to check assumptions.

“Paint Done” vividly and concretely.

Invite questions: “What do you need from me to succeed?”

Create feedback loops: catch confusion early.

When teams understand not just what’s needed but how success is defined, performance shifts. The gap between expectation and delivery narrows. And everyone saves time, energy, and stress.

Speech Acts: The Power of Effective Requests

Alan Sieler’s work on Speech Acts in leadership brings language into sharper focus. Many leadership frustrations come from ineffective requests - vague, assumed, or missing key details.

He outlines five conditions for a powerful request:

A Clear Speaker & Listener

Is the listener fully present? Have they even heard the request?

A Well-Specified Action

What exactly are you asking for? “Paint Done” applies here too.

Conditions of Satisfaction

What will a successful outcome look like? Be measurable and specific.

“Please format this deck, add Q4 results, and send it by 3 PM.”

A Timeframe

Without it, it’s just a wish.

A Clear Commitment

Silence isn’t agreement. Did the other person explicitly say yes?

Beyond Words: Emotions and Body Language Matter Too

In ontological coaching, we look at the whole person—not just the language they use, but the emotional space and physical presence they bring to communication.

When making a request, ask yourself:

What’s the concern I’m trying to take care of?

Are you clear on what outcome you really need?

What emotional space am I in?

Are you anxious, rushed, or irritated? That will shape how your request lands.

What posture am I holding?

Are you open and receptive, or tense, signalling that speed matters more than clarity?

Leaders often unconsciously communicate “don’t question this” with their body. A clenched jaw and hunched shoulders send a very different message than calm curiosity and open posture.

Reflection Prompts:

Think of a recent time when someone didn’t follow through. What could you have done differently?

Where do you see recurring miscommunications?

What new habits could you build to create more clarity and commitment?

In Summary

When leaders ask, “Why don’t they just do what I told them?” the deeper questions are often:

Was my request clear enough?

Did I invite questions and confirm understanding?

Did I make the implicit, explicit?

With awareness, practice, and support, leaders can transform how they communicate, making delegation less of a guessing game and more of a collaborative, energising exchange.

As a coach, I help leaders build clarity, accountability, and connection - one powerful conversation at a time.

#Leadership #Delegation #Coaching #Communication #Productivity #SpeechActs #SelfAwareness