What makes a good advisory relationship actually work
Ruth has been in advisory relationships that worked well and ones that quietly stopped being useful without either party quite acknowledging it. The difference is usually not chemistry or expertise. It is structure, and specifically whether both parties are honest about what they need from the relationship at each stage.
Clarity about what the advisor is for
An advisor is not a co-founder, a therapist, a board member, or a friend, even if they are also one of those things. The advisory relationship works best when both parties are clear about what it is: a structured, time-limited arrangement in which one person brings an outside perspective to help the other think more clearly.
When that clarity slips, the relationship tends to drift. The founder starts using the advisor as a sounding board for everything, including things the advisor is not well-placed to help with. The advisor, not wanting to be unhelpful, goes along with it. Neither party gets much value.
The habits that keep it useful
Ruth asks clients on a monthly retainer to send a short note before each call: what has happened since we last spoke, what is the current question, and what would a useful outcome from this call look like. It takes ten minutes to write and makes the call significantly more productive.
The other habit that helps: a brief review every three months of whether the arrangement is still serving its original purpose. Not a formal evaluation, just an honest conversation. If the answer is 'not really', that is useful to know before another three months pass.
When to end it
A good advisory relationship ends when it has done what it was for. That is a success, not a failure. Ruth builds this into every retainer arrangement: 30 days notice to end, no questions asked, and a short closing conversation to make sure the work is in a useful state. The goal was never to be indispensable.
The best advisory relationships Ruth has been in felt, at the end, like they had a natural stopping point. That is what good structure produces.