The Leadership Skill No One Talks About Enough: Knowing When to Make the Move

Most leadership content focuses on strategy, systems, and skills. How to delegate, to communicate or to build a team. All of that matters, but there's a piece that gets talked around more than it gets talked about directly, and it's probably the one thing holding more women back in business than anything else.

It's the gap between knowing what the next move is and actually making it.

You probably already know

If I asked you right now what the next real move in your business is, you'd likely know the answer. Maybe it's raising your prices, letting go of a client, hiring someone so you can stop doing everything yourself, making the pivot you've been thinking about for months, or launching the thing you keep putting off until conditions feel right.

You know what it is… The question is why you haven't done it yet.

For most women in business, the honest answer isn't that they need more information or a better plan. It's that the move feels risky in a way that's hard to sit with. And so instead of making the decision, they stay in a kind of extended preparation phase that feels productive but isn't really moving anything forward.

I'm not saying that to be harsh. I've watched incredibly capable women stay stuck in that pattern for years, and the frustrating part is that the preparation phase often looks identical to the growth phase from the outside. You're busy, learning, working on things. But the actual decision keeps getting deferred, and the business stays more or less where it is.

What's actually in the way

The hesitation is rarely irrational. When women share what's holding them back from a decision they already know they need to make, the fears are usually real and specific. What if this doesn't work and I've burned the good thing I had? What if I make the move and nothing happens? What if I'm not as ready as I think I am?

Those are legitimate concerns. The problem is that they're also concerns that will never fully go away. There is no version of a significant business decision where the risk disappears before you make it. The risk is part of the decision. Waiting for it to feel safe enough is, in most cases, just waiting indefinitely.

What I've observed in women who've made significant moves in their businesses, and who came out the other side having grown because of them, is they made the decision to act before they felt confident. The confidence came after, as a result of having done the thing, not as a prerequisite for doing it.

That's a meaningful distinction, and it doesn't get said clearly enough in leadership conversations.

Decisiveness as a learnable skill

There's a tendency to treat decisiveness as a personality trait, something you either have or you don't. I don't think that's accurate. I think decisiveness is a skill, and like most skills it gets stronger with practice.

Every time you make the call, even when it's uncomfortable, you're building the capacity to do it again. Over time that compounds, and the women who have built that capacity are the ones who tend to scale their businesses faster.

The other thing that builds decisiveness is being around other people who make decisions. This is one of the less obvious benefits of being in professional communities with women who are actively growing their businesses. When you watch someone else make a move you've been afraid to make and see that they survived it, and often thrived because of it, it recalibrates what feels possible for you. That's not a small thing.

What gets better when you make the move

When women in business stop deferring the decisions they already know they need to make, a few things tend to happen.

Their revenue changes, because they've either raised their prices, let go of the wrong clients, made the hire that freed up their capacity, or launched the thing they'd been sitting on. The business starts to reflect their actual vision rather than the version they defaulted into. They stop carrying the low-grade weight of the deferred decision, which takes up more mental and emotional space than most people realize until it's gone.

None of that happens while you're still in the preparation phase. It only happens after the decision.

The room where those conversations happen

One of the things I'm most intentional about at Rogue Valley Women in Business is creating space for these conversations. Not the polished version of leadership where everyone talks about what worked. The real version, where women who've made hard moves talk honestly about what it cost, what they were afraid of, and what happened when they did it anyway.

Those conversations matter because they make the decision feel less abstract. They also remind you that the woman across the table from you, the one who looks like she has it figured out, had her own version of the same fear. She just made the call.

If you're in the Rogue Valley and you want to be in rooms where those conversations happen, that's what we're here for. You can see what's coming up here and find out about membership here.

The move you've been thinking about is probably already clear. The question is just when you're going to make it.

About the Author

Brigitte Boots is a Fractional CMO and marketing strategist with 15+ years of experience helping service-based businesses figure out why their marketing isn't working (and fixing it). She has led marketing strategy across healthcare, financial services, B2B, and retail, scaling a medical practice from 8 to 20 locations, pulling a nonprofit back from the brink of closing, and helping founders build brands that convert.

Through her business, Lost My Boots, Brigitte works closely with established business owners who are great at what they do but stuck on how to market it. Her approach skips the trends and gets straight to what's actually broken (the messaging, strategy, and systems), then builds something that works without running the business owner into the ground.

She is also the President of Rogue Valley Women in Business, where she actively works to connect, support, and grow a community of women entrepreneurs in Southern Oregon.

Brigitte lives on 20 acres in Talent, Oregon with her husband, Max, and their two dogs.