Why Won't My Managers Set More Audacious Goals?

Read Time: 4 minutes.

The last two “behind the scenes” playbooks have been two of our most popular:

1. What Is My Ideal Allocation of Leadership Energy, Time and Focus?

2. Stop Trying to Convince People to Change

So let’s keep it going today with another real coaching scenario…

My Team Keeps Trying To Set Uninspiring Goals

"I asked my leadership team to come up with goals for Q3 that will help us level up as a company. Nothing incremental - transformative. In their area or outside it. I want big ideas we can iterate on at our offsite. Unfortunately, everything I got back was safe, incremental, and business as usual."

I see this pattern constantly in my coaching sessions.

A CEO spends days with their leadership team identifying strategic priorities. Real breakthrough thinking. Detailed plans with owners and deadlines. Everyone leaves energized about the company's direction.

Six weeks later, they ask for quarterly goals.

What comes back? Safe, incremental, business-as-usual thinking with zero connection to the strategic work they just completed.

It's like amnesia struck the entire leadership team.

What We Get Wrong About Goal Setting

We Ask for Goals Instead of Outcomes Most leaders say: "Give me your top 10 goals for next quarter."

What they get back: A laundry list of tasks dressed up as objectives.

The head of engineering submits hiring targets. The VP of sales lists revenue metrics they'd hit anyway. The CFO focuses on operational improvements.

None of it moves the needle.

We Anchor Goals to Departments When you ask people to think within their functional area, you get functional thinking. But the biggest opportunities usually live at the intersections.

Your sales leader won't naturally think about product innovation. Your CFO won't propose new market strategies. Your head of operations won't suggest partnership opportunities.

We Treat Strategic Planning as Separate from Goal Setting Here's the killer: Most leadership teams do strategic planning and quarterly goal setting as completely separate exercises.

Strategy happens at the offsite. Goals happen in spreadsheets. Never the two shall meet.

The Strategic Disconnect Problem

Why does this happen? Three systemic failures:

Failure #1: No Strategic Keeper Who owns ensuring your strategic initiatives stay alive between planning sessions? Most CEOs assume it happens naturally.

It doesn't.

Without a clear owner, strategic work becomes an orphan. It lives in a separate document that nobody references during operational planning.

Failure #2: No Forcing Function There's no mechanism requiring quarterly goals to connect to strategic priorities. So people default to what feels safe and familiar.

They optimize for goals they know they can hit rather than outcomes that could transform the business.

Failure #3: No Iteration Process Most leaders accept the first round of goals, even when they're disappointed. They don't want to seem micromanaging or demotivating.

But accepting uninspiring goals is more demotivating than pushing for better ones.

How to Build The Strategic Connection

Here's how to fix this:

Step 1: Designate a Strategic Keeper One person (not you) owns the strategic initiatives. Their job is ensuring these don't die in a drawer.

They track progress, surface blockers, and most importantly, connect strategic work to operational planning.

Step 2: Lead with Strategic Context Don't ask for goals in a vacuum. Start every goal-setting conversation with: "Here are our strategic priorities. How do your quarterly goals advance them?"

Force the connection. Refined goals will often fall out of the revisions.

Step 3: Apply the Transformation Test After reviewing their goals, ask: "If we accomplish everything on this list, will we be meaningfully different as a company?"

If the answer is no, you haven't asked (or uncovered) the right things. Keep digging.

My “One Big Thing” Principle

Here's what I learned from studying high-performing teams: People can't focus on multiple transformative initiatives simultaneously.

They'll default to tactical work that feels urgent and measurable.

So instead of asking for 10 goals, ask for this structure:

• Operational Targets: The metrics you need to hit to keep the business running

• Functional Improvements: The 2-3 things that will make your area more effective

• One Big Thing: The single initiative that could transform your trajectory

That one big thing should:

• Connect to your strategic framework

• Require thinking beyond business as usual

• Have the potential to unlock new capacity or capability

Don’t Demotivate. Iterate to Great.

Revisions are a feature not a bug. They show your team can disagree productively.

When you get uninspiring goals (and you will), don't accept them. Iterate.

Round 1: The Reality Check "I reviewed your goals. Most feel incremental. Help me understand—was that intentional? What would it take to aim higher?"

Give them a chance to explain their thinking before redirecting.

Round 2: The Strategic Bridge "I don't see clear connections to our strategic priorities. Can you walk me through how these goals advance our bigger picture?"

This surfaces whether they forgot, disagreed, or didn't understand the strategic work.

Round 3: The Transformation Challenge "What would need to be true for one of these goals to fundamentally change how we operate?"

Push them to identify the transformative element themselves.

The Systems Solution

Your executives are capable of strategic thinking.

They proved it during your planning sessions and through previous success.

But without systems connecting that thinking to operational reality, they'll default to what feels safe.

Your job isn't to think strategically for them. It's to create conditions where strategic thinking becomes their natural ambition.

Because incremental goals, no matter how well-executed, won't build the company you're trying to create.

What You Missed This Week

Our Wednesday AM posts:

📌 Why Leaders Must Learn to Delegate (Dave on LI)
📌 How To Run a Team Pulse Check (Mar on LI)
📌 How to Build Your Personal User Manual (Dave on X)

And here are our most popular posts last week:

🔥 3 Tests for Assessing Underperformers (Dave on X)
🔥 Bad Leadership Habits I Had to Unlearn (Mar on LI)
🔥 Eye-Popping Workplace Stats from Microsoft Study (Dave on LI)

Our goal is to build a community of 1 million thoughtful, curious leaders.

You can help us by reposting anything that resonates with you.  

Thank you for reading. Appreciate you!

Dave & Mar