Mentorships and Long-Form Engagements
A mentorship is the relationship a series of sessions adds up to. It is where milestones live, and where you can see whether the work is actually going anywhere.
What you will learn
- How a mentorship differs from a booking and from a package
- What milestones are for
- How mentorships begin
- When to end one
Three things that sound similar#
The portal has bookings, packages and mentorships, and it is worth being precise about the difference because they solve different problems.
| What it is | What it tracks | |
|---|---|---|
| Booking | One session at one time | That session |
| Package | A commercial bundle bought up front | Sessions remaining and validity |
| Mentorship | An ongoing relationship | Progress, milestones and history |
Milestones#
Milestones are the point of a mentorship. Without them a long engagement becomes a sequence of pleasant conversations that nobody can evaluate. With them, both sides can see whether the thing you agreed in month one actually happened.
- Set milestones that are observable, not aspirational - ‘first paying enterprise customer’ rather than ‘improve sales’
- Keep them few; three or four across a quarter is plenty
- Review them at the start of a session rather than the end, when there is still time to act
Milestones protect you too
When a founder is not making progress, a written milestone turns an awkward conversation into a factual one. It is the difference between ‘I feel like this is not working’ and ‘we agreed this by March and it has not moved’.
How they start#
Mentorships grow out of the other surfaces rather than being created cold.
From repeat sessions
A mentee who keeps booking you is already in a mentorship in everything but name. Formalising it gives the relationship somewhere to record progress.
From a package
Someone who buys a multi-session bundle has committed to a run of work. That is the natural shape of a mentorship.
From an association
An incubator or investor placing you with one of their companies is creating a mentorship with a third party paying for it.
Ending one#
Mentorships should end. The useful ones end because the work is done; the rest end because they have quietly stopped being useful and someone has to say so.
Good to know
Ending a mentorship does not delete its history. The sessions, notes and milestones remain, which is what makes it worth having recorded them.
No. Repeat bookings work perfectly well. A mentorship adds structure and a place to track progress - worth it for a quarter-long engagement, overkill for three ad-hoc calls.
Yes, and they should. A milestone only works as a commitment device if both sides are looking at the same list.
