How to find a startup advisor and what to ask before you hire one

Founders often ask me to introduce them to a startup advisor before they can tell me what they need advice on. The question is usually some version of 'Do you know someone good?' as if good were a single quality that applies to every situation. It isn't. The search for a startup advisor starts with the problem, not the person, and the founders who get the most value are the ones who know the difference.

The first thing to write down is the decision that's actually in front of you. Not your entire business. Not your five-year vision. The one thing you'll have to decide in the next month that could change the shape of the next six. It might be pricing, it might be a pivot, it might be whether to hire your first engineer or cut a feature that isn't working. The more specific you can make it, the more useful the advisor search becomes.

Once you know the decision, you know what kind of experience you're looking for. A generic 'startup advisor' is rarely what you need. You need someone who has made or watched someone make the specific decision you're about to make, in a context that's close enough to yours to matter. If you're trying to figure out B2B pricing for a new category, a former B2C growth lead isn't the right fit even if they're brilliant. If you're deciding whether to rebuild your infrastructure, you want someone who has lived through a similar rebuild, not someone who has scaled consumer apps.

The second filter is recency. Startup advice ages badly. The person who raised a Series A in 2014 and hasn't been close to a product since then is giving you history lessons, not advice. The market changes, the channels change, the buyer psychology changes, and the cost of building changes. I'm not saying experience has to be from this year, but it has to be from this era. Ask when they last dealt with the thing you're dealing with, and listen carefully when the answer is more than five years old.

The third filter is decision speed. A startup advisor who only answers in scheduled calls and gets back to you in a week is useful for strategy and dangerous for operations. The questions that derail founders arrive on Tuesday afternoon and need answers by Wednesday morning. If you're building alone, the lag between your question and their answer is part of the cost of the advice. Ask how quickly they usually respond and what channel they work in. The answer tells you more about fit than the bio does.

So where do you find them? Warm intros are the fastest if you have them, but most solo founders don't have a deep network of senior operators. The next best place is public work. Look for people writing or speaking clearly about the specific problem you're facing. Not the ones with the biggest following. The ones whose take on your problem makes you stop and think. If they can explain a hard decision in a way that gives you clarity, there's a decent chance they can give you clarity in conversation.

Communities can work, but they're noisy. The advice that gets the most upvotes in a founder community is often the advice that sounds the most confident, not the advice that's the most right. Use communities to find names, not to evaluate them. One thoughtful comment on a hard thread is worth more than a hundred generic 'happy to help' offers.

When you get into the first conversation, don't sell yourself. Don't pitch your startup. The point of the conversation is to test whether this person can actually help you with your specific decision. Bring the decision in as much detail as you can. Describe the options, the constraints, what you're afraid of, and what you're leaning toward. Then watch what they do. A good advisor will ask clarifying questions before giving advice. They will name the parts of the situation you might be missing. They will tell you what they don't know. They won't immediately give you a three-step plan.

The questions you ask them are as important as the questions they ask you. Ask about a similar situation they have actually been in. Ask what they'd do if they were in your seat. Ask what they got wrong the last time they advised someone on this. Ask what they'd need from you to be useful. The answers will tell you whether they're thinking about your problem or just performing competence. The difference is obvious once you're listening for it.

There are red flags to take seriously. The advisor who has a playbook for every business. The advisor who talks more than they ask. The advisor who is always available and never seems busy. The advisor who promises outcomes. The advisor who makes you feel small. The advisor who gives you the same advice they gave the last three founders you introduced them to. Any of these can cost you months. The best advisors are specific, honest, and a little hard to get.

The last thing to know is that you're allowed to test the relationship. Founders often treat an advisor conversation like a commitment. It's just a conversation. Pay for one month if the work is paid, or ask for one structured session if it's equity. See what happens when you bring a specific question. If the advice is late, generic, or leaves you more confused than you started, keep looking. The right advisor isn't the one who impresses you in the first call. The right advisor is the one whose advice you actually use.

If you're a solo founder, this matters more because you don't have a team to absorb bad advice. The wrong advisor doesn't just give you a bad read. They become a second voice in your head, and when there's no one else to check that voice, it can sit there for months. Choose carefully. Choose for the specific decision. And choose someone who helps you make decisions faster, not someone who gives you more to think about.

If you want to see how I work with founders on this, read about founder coaching or startup coaching for early founders.