Strategy that clicks

Kia ora (Hi there) Change Wranglers,

This week, I’ve been happy to be a part of strategy talks on how to evolve a crucial organisational function.

It’s got me thinking about how to have practical strategic discussions.

I’ve also been celebrating how our role as change managers means we transition between efficient, tactical delivery and very high-level, contextual work.

I love that!😁

It’s a joy not to be locked into doing ‘one thing’ that can make the working day dull and predictable.

Strategic conversations aren’t about having all the answers.

They’re about surfacing the right questions.

When you’re sitting across from a C-suite leader, your job isn’t to educate — it’s to provoke insight, help them see around corners, and connect change initiatives to their strategic goals.

Here are some tips for having helpful strategic conversations.

If you want to listen to this newsletter as a podcast click here.

1. Start With Context, Not Content

We started this week’s strategic discussion with the provocative question - why do we do...* (a core organisational function)?

Then we asked, ‘What would the consequence be if we stopped doing it?’

Note that leaders don’t want a play-by-play. They want clarity on where things are going and why it matters.

You can open a similar discussion with -

• “What’s keeping you up at night when you think about the next 6–12 months?”
• “If this change succeeded beyond expectations, what would that unlock for the business?”

2. Don’t Just Inform — Frame

Instead of just stating tactical features of what’s currently done, offer insight. Say:

• “Here’s what we’re noticing in the system…”
• “Here’s how this could impact key capabilities over the long run…”

3. Ladder Up to Strategy

Always connect your change initiative to business outcomes. Ask:

• “How does this align with our growth/playbook/resilience strategy?”
• “Which levers are we pulling — cost, agility, customer experience?”

4. Speak Their Language

Use the metrics and terms that matter to them. Revenue, risk, ROI. Don't just talk about adoption and resistance. Ask:

• “Where are we over-investing for the return we’re seeing?”
• “What would it take to de-risk this without slowing momentum?”

5. Invite Them to Think with You

Create space for collaborative reflection:

• “If we could only do one thing well this quarter, what should it be?”
• “Who’s not in this room that could derail this?”

Other conversational starters that work

You can also use:

• “If we’re successful, how will we know? What evidence will we see?”
• “What risks are we not talking about?”
• “What’s the bold move no one’s made — yet?”

If you want more of these types of questions and you don’t have them yet, get my free download ’40 Great Questions Change Questions for Projects’.

Or if you want to have strategic discussions with a change management lens on leadership, take a look at this from the Center for Creative Leadership.

And if you're looking for new strategic ways to know your stakeholders and strongly identify what will motivate their change adoption check this out.

Until next time, keen changin’ for the better.

Your change fairy godmother, Barb 🧚♀️✨

Barb Grant

Helping you find the best questions.

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