Chapter 16: Engagement Models
How you structure your work matters as much as what you charge. The wrong structure can trap you in low-value work.
What You'll Learn
- Advisory retainer vs. implementation models
- Avoiding the fractional employee trap
- Self-contained project structures
- Using Slack Connect for boundaries
Advisory Retainer Model
The advisory model focuses on access and guidance rather than deliverables.
Structure
| Component | Description |
|---|---|
| Weekly meetings | 1-4 hours/month with leadership |
| Async access | Unlimited Slack/email questions |
| Pair programming | Jump on calls as needed |
How to Position
"For $60,000, we do 4 hours a month of meetings. But really a lot of it is asynchronous work—I'll jump on a call and pair program with your team if it makes sense."
Why It Works
The value isn't priced by the hour. You're paying for access to someone who's seen these problems before.
"I'm not going to charge you for how long I'm interviewing my friends. If I know the answer, I should get rewarded the same as if I had to make a bunch of calls."
The Fractional Employee Trap
The Danger Zone
Being invited to the client's Slack, given a company email, and treated like a lazy employee.
Warning Signs
| Sign | What's Happening |
|---|---|
| Invited to all-hands meetings | Boundary erosion |
| Given company email | Identity confusion |
| Waiting days for environment variables | Treated as low priority |
| Put on phone screens without context | Used as a resource |
| Moving Jira tickets around | IC work, not consulting |
| "Can you attend our standup?" | Embedded in their process |
The Problem
"I used to do a thing where I said '$250/hour but only up to 10 hours a week on average.' You just get invited to the Slack. You just treat it as an employee, but you look like the laziest employee because you're just not pushing as much code."
Avoiding the Fractional Trap
Solution 1: Use Slack Connect
Stay in your own Slack organization:
"Have your own Slack organization. Always set up as Slack Connect where there's a single channel to contact you."
Benefits: - Everyone knows you're external - No one accidentally assigns you work - You control notifications - Clear professional boundary
Solution 2: Work in Isolated Repos
Keep your deliverables self-contained:
"Give them a private GitHub repo on their org. Your engineers can reference this. That's straightforward."
When projects have clear deliverables, you maintain control over time and perception.
Solution 3: Define Scope in Proposals
Be explicit about your role:
| Instead of... | Write... |
|---|---|
| "Jason will help the team" | "Jason will work directly with the CTO on strategy" |
| "Available for questions" | "Weekly sync with designated contact" |
| "Support as needed" | "4 hours/month of meetings plus async channel" |
Self-Contained Projects
The cleanest engagements have clear boundaries.
Characteristics of Clean Projects
| Element | Example |
|---|---|
| Clear deliverable | "Prototype of X feature" |
| Defined timeline | "6 weeks to delivery" |
| Specific handoff | "Delivered via private repo" |
| Limited scope | "Does not include deployment" |
Example Structure
Phase 1: Discovery (Week 1-2) - Interviews and assessment - Requirements documentation - Architecture recommendation
Phase 2: Development (Week 3-5) - Prototype development - Internal testing - Documentation
Phase 3: Handoff (Week 6) - Delivery to client repo - Knowledge transfer session - Support documentation
Pilots That Roll Into Contracts
Structure pilots as the beginning of longer engagements:
"It's a 6-month contract with a 6-week cancellable period. If you don't cancel, it rolls over."
Why This Works
| Traditional Pilot | Rollover Structure |
|---|---|
| "2-week trial, then negotiate" | "6-month contract, cancel by week 6" |
| Re-contracting friction | Automatic continuation |
| Client evaluates during trial | Client evaluates, default is continue |
| Momentum breaks | Momentum maintained |
The Language
"This isn't a 4-week contract. It's a 6-month contract with a 6-week cancellable period. That's your guarantee. That's what de-risks it. But it is the annual contract at the end of the day."
After Implementation: Maintenance Retainers
After delivering a project, offer ongoing support:
"For $5,000/month, I'm happy to still be on Slack, have access to your infrastructure, and debug things asynchronously."
Typical Conversion
Clients who paid $40,000 for implementation are often happy with a $10,000/month retainer—25% of the original engagement for ongoing access.
Maintenance Tiers
| Tier | Price | Includes |
|---|---|---|
| Light touch | $3-5K/month | Monthly call, email support |
| Active support | $7-12K/month | Weekly calls, async Slack |
| Strategic | $15-25K/month | Deep involvement, proactive guidance |
Transitioning from Implementation to Advisory
As you establish credibility, shift toward advisory work:
The Path
- Start with implementation to prove expertise
- Document what you deliver for case studies
- Build relationships with leadership
- Propose advisory after successful delivery
- Reduce hands-on work over time
The Script for Transition
"Now that we've successfully implemented [project], I want to ensure you continue getting value. Many clients find ongoing advisory helpful for optimization, team questions, and new opportunities. Here are a few options for how we could structure that..."
Setting Boundaries in Proposals
Include explicit boundary language:
Communication Clause
"Consultant will be available for asynchronous communication via [Slack Connect/Email] during the engagement. 'Unlimited' communication is subject to reasonable use. Consultant will respond within one business day to non-urgent requests."
Role Definition
"Consultant will work directly with [specific person/role]. All requests should be channeled through this designated contact. Consultant is not available for general team meetings unless specifically agreed."
Scope Boundaries
"This engagement includes [specific deliverables]. Items not listed are out of scope and would require a separate agreement."
Action Items
-
Set up Slack Connect. If you don't have your own Slack workspace, create one this week.
-
Audit current engagements. Are you trapped in any fractional employee situations? Plan your exit or boundary-setting conversation.
-
Create boundary language. Write the communication and role clauses for your next contract.
-
Design your rollover pilot. Structure your next pilot as a cancellable long-term contract.
-
Plan maintenance offerings. Define 2-3 post-implementation retainer options.
Key Takeaways
- Advisory retainers value access and expertise, not hours worked
- The fractional employee trap makes you look like the laziest employee
- Use Slack Connect, isolated repos, and explicit scope to maintain boundaries
- Self-contained projects with clear deliverables are cleanest
- Structure pilots as cancellable long-term contracts, not trials
- After implementation, convert to maintenance retainers (typically 25% of project value)
- Include explicit boundary language in all contracts