Most fractional CMO engagements don't get a real 90-day evaluation. They drift, then quietly end without learning anything. Here's the framework for actually evaluating whether the engagement is working.
At 90 days, evaluate against three categories: (1) diagnostic clarity (do you have a clear picture of what's broken and what to fix?), (2) execution velocity (did promised work ship?), (3) relationship health (do you trust them?). If all three are strong, extend. If diagnostic clarity is missing, it's never going to come — end. If execution is slow, address explicitly. If relationship is bad, end.
Evaluate at 90 days on:
1. Diagnostic clarity. Do you have a clearer picture of what's broken in marketing than you did 90 days ago? Can the fractional CMO articulate the 2-3 highest-leverage problems?
2. Execution velocity. What specific work has shipped in 90 days? Promised vs delivered ratio?
3. Relationship health. Do you trust their judgment? Are conversations productive? Do you look forward to or dread the meetings?
At 90 days, you should be able to:
• List the 3-5 most important marketing problems you're solving
• Articulate why they matter and how they connect to revenue
• Have a written plan for addressing each
• Have data backing the diagnosis
If you can't, the fractional CMO hasn't done diagnostic work. This is a serious flag — it's the foundation of everything else.
At 90 days, you should see specific work shipped:
• Some marketing infrastructure improvements (CRM cleanup, MAP, reporting)
• At least 1-2 strategic projects in motion (positioning refresh, channel test, campaign launch)
• Initial team improvements (hiring, role clarity, performance addressing)
Pattern that fails: lots of 'strategy work' with nothing shipped. Pattern that succeeds: clear diagnostic + early visible wins.
At 90 days, ask yourself:
• Do I trust their judgment on marketing decisions?
• Do they push back productively when I'm wrong?
• Do they execute promises reliably?
• Is communication clear and proactive?
• Do I look forward to or dread the meetings?
Relationship problems at 90 days usually mean either wrong fit or fundamental personality mismatch. Rarely fixable; usually time to end.
Three scenarios:
1. All three categories strong: Renew confidently. Probably 12-18 more months.
2. Mixed: Have an explicit conversation. 'Here's what's working; here's what I need to see in the next 30 days.' Make the bar specific.
3. Two or more weak: End the engagement. Don't drag a struggling engagement into year 2.
Two patterns work:
For renewing: 'I'd like to extend through [date]. I want to focus next quarter on [specific priorities]. What do you need from me to make that succeed?'
For ending: 'I've appreciated working together. I'm going to end the engagement effective [date — 30-60 days out]. I want to make this transition clean. What do we need to wrap up?'
Avoid: drifting end without conversation. Avoid: surprise endings. Avoid: extending when you've already decided not to.