The Decision-Making Gap 🔄
November 18th, 2025
I was going to write about The Implementation Gap today – why your strategic clarity keeps dying in the execution phase.
But then I had three conversations over the last week that made me realize something:
The implementation problem often starts way earlier. It starts with the DECISION.
I wrote about this pattern on LinkedIn last week – a multi-six-figure coach + consultant who was making every decision in a vacuum, and it was costing her more than bad hires. (You can see the post and join the conversation here.)
She was hiring quickly to fill urgent needs, saying yes to partnerships that looked good on paper, keeping team members on way too long – all because she didn’t have space to think strategically before committing.
In his book Clear Thinking, author Shane Parrish calls this “reacting without reasoning” – the cost of not recognizing when you need to pause and think clearly.
And I’m seeing this same pattern everywhere right now.
Henry came to me after investing in three different things this year:
- A marketing person who seemed perfect at first (ended the contract 3 months early because their experience was a mismatch)
- A self-publishing course with a compelling offer (turned out to be content he’d already worked through)
- A $3K/month speaker mastermind with an incredible weekend retreat (but the ongoing program felt like too much groupthink, and the energy was off)
None of them were bad. But none of them were quite right.
And he kept wondering: “Is it me? Am I just being difficult?”
Eli joined a mastermind. Solid facilitator, good people. But he’s noticing limited engagement and realizing he needs actionable, challenge-driven sessions – not more reflective group discussions. He’s wondering if he should say something or just quietly step away.
Here’s what I told both of them:
You’re not difficult. You’re discerning.
And you need someone asking you the harder questions BEFORE you invest – not after you’re six months in, wondering if you made the right call.
When you’re 3-5+ years into your business with proven offers and real revenue, you’re getting pitched constantly:
Masterminds. Coaching programs. Done-for-you services. Strategic partnerships.
And they all sound compelling in the sales conversation.
But here’s what I’m noticing: Most established founders are making these decisions alone.
Eli didn’t have anyone to think through whether this mastermind was actually serving him. Now that we’re working together, he has a thought partner to help him evaluate if it’s worth staying or if it’s time to move on.
Henry got emotionally attached to the possibility each time and said yes. Looking back, he can see the red flags he missed – but in the moment, he didn’t have a thought partner asking the harder questions.
The consultant from my LinkedIn post was making hiring and partnership decisions in the 10 minutes between meetings – no space to step back and ask, “Is this actually what I need right now?”
The questions nobody’s asking you before you invest:
- Where are you actually stuck right now – and is THIS the thing that addresses that?
- What’s already on your plate? Does this genuinely fit your capacity, or are you hoping it will somehow create more time?
- What have you already worked through? Is this content you need, or content you’ve already mastered?
- What’s the opportunity cost? If you say yes to this, what are you saying no to?
- What does your gut actually say when you take the sales pressure out of the equation?
This isn’t about being cynical. It’s about being strategic.
Because at your level, the wrong yes costs you more than money – it costs you momentum, focus, and six months of wondering if you’re the problem.
What you actually need isn’t another program.
You need someone who helps you think through which opportunities are worth your investment – before you’re in too deep.
That’s where a Fractional Chief of Staff creates real value.
Not as a replacement for masterminds or marketing support or coaching programs.
As the strategic thought partner who helps you evaluate whether those opportunities actually fit where you are and where you’re going.
Someone who asks: Is this the right investment for you right now? Or does it just sound good?
Someone who can spot patterns you’re too close to see: You’ve said yes to three things this year that all promise X, but what you actually need is Y.
Someone who knows your business well enough to say: This might be amazing for someone else, but here’s why I don’t think it’s the right move for you.
That’s The Decision-Making Gap.
And it’s the most valuable filter you can have before you invest in anything else.
REFLECTION: “The Investment Audit”
Take 10 minutes to think back:
- What have you invested in over the past year? (Programs, coaching, masterminds, done-for-you services, team members)
- Which ones felt “right” when you said yes? What made them compelling?
- Which ones turned out to be not quite right? What were the red flags you missed?
- What pattern do you notice? Are you making these decisions alone? In a rush? Based on emotional attachment to the possibility?
If you’ve invested in programs that looked perfect but didn’t quite fit…
If you’re tired of making big decisions alone and then wondering six months later if you made the right call…
If you want a strategic thought partner who helps you evaluate opportunities before you commit – not after you’re stuck…
Let’s talk.
I work with established coaches and consultants ($250K+) as a Fractional Chief of Staff. Part of what I do is help you think through which investments, partnerships, and opportunities are actually right for where you are – and which ones just sound right.
Not because I have all the answers.
Because you need someone who asks the right questions before you say yes.
Talk soon,
Moriah
P.S. Henry told me during our call: “I want people in my circle who don’t just see me as a dollar sign, but who know and recognize my worth and vision – operating on the same frequency.”
The filter for that? Having someone help you see which opportunities actually operate on your frequency – before you invest.