Most fractional executives don't lose deals because they're bad at what they do.
They lose deals because they don't have a system.
After placing 2,000+ fractional executives at $10K-$25K/month retainers, I've seen the pattern repeat hundreds of times. Talented people. Great at their craft. Losing deals to disorganization.
The pipeline lives in their head. Or a spreadsheet they haven't opened since last quarter. Or nowhere at all.
And when you ask them why their pipeline is empty, they say things like:
"I've been busy with delivery."
"I need to get back to business development."
"I'm waiting to hear back from a few people."
None of those are systems. Those are hopes.
Here are three rules that separate fractional executives who close from those who wait.
Rule 1: The Math That Replaces Hope
Here's the arithmetic nobody wants to hear:
20 targeted outreach messages = 1 discovery call.
5 discovery calls = 1 signed client.
That's 100 messages to land one client at $10K/month.
Not networking. Not "putting yourself out there." Not posting on LinkedIn and hoping someone reaches out. One hundred targeted, intentional outreach messages.
If your pipeline is empty right now, count your outreach messages this month.
Under 80? That's why.
This math isn't pessimistic. It's liberating. Because once you know the formula, you can work it backwards.
Need two clients this quarter? That's 200 messages. About 17 per week. Four per day.
Suddenly "I need more clients" becomes "I need to send four messages today."
Process beats network. Every time.
Rule 2: The 20% Rule
When you land your first fractional client, something dangerous happens.
You get busy.
You're delivering value. You're in the work. You're finally doing the thing you're good at.
And you stop prospecting.
The pipeline goes cold. Contacts go stale. Outreach drops to zero.
Then the engagement ends. And you're starting from scratch with an empty pipeline and mounting panic.
I call this the One-Client-Wonder trap. And it kills more fractional practices than bad positioning ever will.
The fix is the 20% Rule:
20% of your time is pipeline activity. Always.
Not "when I have time." Not "after this deliverable." Not "once things slow down."
Scheduled. Protected. Non-negotiable.
Here's how it breaks down:
- One client: 80% delivery, 20% pipeline
- Two clients: 80% delivery, 20% pipeline
- Fully loaded: Still 20% pipeline
The math doesn't care how busy you are. The market doesn't care that you're heads-down on a project. Your future self will not thank you for ignoring business development when things felt stable.
Twenty percent. Always.
Rule 3: The Stale Contact Cutoff
Here's a truth that will hurt:
A contact with no activity for 14 days isn't a prospect. They're a fantasy.
Most people carry dead weight in their pipeline for months. Names they reached out to once. People who "seemed interested" six weeks ago. Contacts they're "planning to follow up with."
This isn't a pipeline. It's a graveyard dressed up as opportunity.
Here's the rule:
- No response after 3 touches? Move to Nurture with a 90-day follow-up.
- No response after the 90-day follow-up? Move to Lost.
- Responded but went cold? One more touch, then Nurture.
Stop carrying ghosts.
A pipeline of 20 real prospects — people who've responded, who have a timeline, who have budget authority — beats a pipeline of 50 names you're hoping will magically re-engage.
Clean your pipeline. Weekly. Ruthlessly.
The clarity alone will change how you operate.
Why These Rules Matter
These three rules aren't complicated:
- The Math: 100 messages = 1 client. Know your numbers.
- The 20% Rule: Pipeline activity is non-negotiable, even when busy.
- The Stale Contact Cutoff: 14 days with no activity = not a real prospect.
But simple doesn't mean easy.
The hard part isn't knowing the rules. It's building a system that enforces them when you're tired, busy, or distracted.
That's why I built First Mate — a CRM specifically for fractional executives, consultants, and coaches. It tracks the math. Shows you when you've broken the 20% rule. Flags stale contacts automatically.
But whether you use First Mate or a spreadsheet or a notebook, these rules apply.
Process beats network. Systems beat hope. And the people who win aren't the ones with the best Rolodex — they're the ones who work the math.
Kirk Coburn created the Fractional CMO category in 2009 and has placed 2,000+ executives at $10K-$25K/month retainers. He writes about the systematic process of building a fractional executive practice.
