Earlier business notes
Choosing advisors you can actually ask for help
How to make an advisory relationship useful: specific questions, relevant experience, clear expectations and room for disagreement.
By Rajiv Sankarlall · Updated
A respected name on a slide is not the same as someone you can call when a decision gets difficult. Before looking for an advisor, identify the questions you need help thinking through and the kind of experience that would be useful.
You may need someone who understands a customer market, has managed a similar team or can challenge your assumptions about the company. You may also need a separate person with whom you can talk honestly about your life. Do not expect one relationship to cover every need.
Make the first request specific
Instead of asking someone to “be an advisor,” bring a bounded question. Explain the situation, what you have already considered and why their perspective seems relevant. A useful conversation can help both of you decide whether there is a reason to continue.
Pay attention to how they respond. Do they ask about your circumstances before prescribing an answer? Can they explain where their experience may not apply? Are you comfortable disagreeing? Familiarity with impressive companies is not enough if you cannot think openly together.
Agree what continuing means
Discuss availability, meeting frequency, preparation and confidentiality. Clarify whether this is informal help or a formal role with responsibilities. If compensation or ownership is involved, get the appropriate professional help to document the arrangement rather than relying on a friendly understanding.
Be clear about conflicts too. An advisor may work with other companies or have their own interests. Ask what could affect their involvement and how you will handle it. That conversation is easier before a sensitive decision arrives.
Bring decisions, then report back
Send enough context for a useful discussion. State the question you want to resolve and the constraints you cannot wish away. Avoid using the entire meeting to narrate everything that happened since the last call.
Afterward, tell the person what you decided, what you acted on and what remains uncertain. You own the decision; the advisor contributes perspective. If advice repeatedly goes unused, examine whether the relationship is addressing the right problem.
An advisor can help you see choices more clearly. Your own judgment and values still matter. If you notice you are seeking permission rather than perspective, that is worth exploring. See how to share decisions without giving up responsibility.