When a sound strategy isn't landing, repair the relationship first

This was so obvious after my client pointed it out: "I'd feel more confident in my product strategy if I knew where my CEO stood."

Of course they're related... but we'd never tied the two so explicitly before.

I wish strategy worked like science: no matter who runs the test, you get the same result. But in the real world, it has to land with someone in power, a human with biases, fears, and sleep deprivation like the rest of us.

When my leaders come to me stressed out (snap at the kids, night-two-of-insomnia stressed), it's never about the roadmap. It's the offhand comment that eats at them, the spidey sense that they've fallen onto the CEO's bad side.

Like: "Well, we'll see if product can deliver this time."

Here's the irony: that person rarely tells you directly. Instead, they make requests: more data, more visibility, another explainer deck. You do all of it, and still they're not satisfied. Because the real issue was never the strategy.

When a sound strategy still isn't going anywhere

It's usually one of four things:

• I haven't shown I get their worries.
• I haven't brought them along in my thinking.
• I haven't shown real interest in their POV.

And sometimes:

• I've underestimated how much trust I need to repair.

With a CEO, that can lead to outright blocking. With a peer, it can show up as passive undermining.

Leaders hate when I point this out: the way forward usually means repairing with the human, not the roadmap. Most would rather polish the strategy than face that conversation.

If your conviction feels shaky, what relationship might need repairing first?

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This post originally appeared on LinkedIn.