Guest Adviser Trial
Test adviser fit through repeated contact and real meetings before committing
- Difficulty
- Easy
- Time to result
- ~months to results
- Steps
- 5
- Confidence
- 93%
Develop an adviser relationship in stages instead of appointing someone after one impressive interaction. Phil described meeting a potential adviser after hearing him speak at an event, asking questions, and then having roughly half a dozen coffee conversations. Nala next invited him to a couple of board meetings in a limited guest-adviser capacity so both sides could test the relationship in real operating discussions. Only after the founders saw valuable feedback and guidance did the relationship continue. The mechanism is progressive exposure: an initial signal identifies relevant experience, repeated conversations reveal rapport and judgment, and a bounded trial tests contribution against actual decisions. It gives founders external perspective while preserving an off-ramp if the advice, chemistry, or expectations do not fit. Appropriate confidentiality and conflict terms should be settled before meeting access.
Origin
Phil Dwinter described how Nala moved one adviser from an event conversation through several coffees and a guest role in board meetings. Extracted from The Foundr Podcast.
Core principles
- 01Use outside experience to challenge day-to-day founder thinking
- 02Build familiarity before offering a formal role
- 03Test adviser value in real business discussions
- 04Assess the relationship in both directions
- 05Formalize only after useful guidance and working fit are visible
How to run it
- 1
Find a relevant judgment signal
Look for someone whose experience or thinking addresses a real gap in the company. Phil first encountered one adviser while that person was speaking at an event.
Pro tip Approach with specific questions rather than a vague request to mentor you.
- 2
Build the relationship gradually
Use several conversations to understand how the candidate thinks and communicates. Nala's founders met the candidate for coffee roughly half a dozen times.
Pro tip Bring real decisions so you can assess the usefulness of the thinking.
Watch out Prestige and speaking ability do not necessarily translate into practical adviser value.
- 3
Define a bounded trial
Invite the person into a temporary guest-adviser role with clear scope. Agree on confidentiality, conflicts, access, and whether compensation applies before sharing sensitive information.
Watch out The transcript explains the staged relationship but does not describe Nala's legal or compensation arrangements.
- 4
Test in real meetings
Include the candidate in a small number of genuine decision sessions. Observe whether the advice improves clarity, surfaces risks, or helps founders sequence opportunities.
Pro tip Evaluate contribution against the decisions the business actually faces.
- 5
Review mutual fit
Ask both sides whether the trial produced useful guidance and a workable relationship. Continue or formalize only when the evidence is positive.
Watch out Do not let an informal trial drift into an undefined permanent role.
In the wild
Phil approached a speaker at an event and asked several questions. They later met for roughly half a dozen coffees. Nala then invited the person to attend a couple of board meetings as a guest adviser so both sides could test the arrangement before continuing.
→ The founders received guidance they considered valuable and found the working relationship strong enough to continue.
Common mistakes
Appointing after one conversation
A strong first impression provides too little evidence about judgment, chemistry, and practical contribution.
Running an undefined trial
Sensitive meeting access needs explicit boundaries around confidentiality, conflicts, authority, duration, and compensation.
Is it for you?
Best for
It is best for founders who need experienced outside perspective but want evidence of fit before making a longer commitment.
Not ideal for
It is not ideal when confidentiality, conflicts, authority, or compensation remain undefined before access to sensitive meetings.
From the transcript
“we caught up for about half a dozen coffees”
“came to a couple board meetings just to test each other out”
“provided us with some really amazing feedback and guidance”
From the episode
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