Questions to Ask Potential Advisors: The Master List

Posted by Jessica Alter /June 4, 2014 / Advisors, Entrepreneurial Advice, Hot Topics, Uncategorized

For a while, one of the most popular questions on FD:Discuss was “What questions should I ask potential cofounders?”  We penned this list and we’re told it’s been quite helpful. But since FounderDating now also connects entrepreneurs and advisors, a more popular question is, “What should I ask potential advisors?” So, without further ado, we made a new list. As startup founders, your quality time is in short supply and the same goes for the advisors you’re seeking, so making the most of those first few conversations is key. After some research of our own and our community’s input, we’ve compiled a definitive list of topics to focus on when evaluating a new advisor.

We’ve broken them down into five categories – Expertise, Experience (and Failure), Company Vision, Fit, and Time.

Expertise – When it comes to expertise, don’t just rely on what you heard or what’s listed on someone’s profile. You should talk in-depth about the skills he or she can bring to the table. 

1. What are the areas where you feel strongest?

2. Can you give me some examples of your work with [area of expertise]? What kinds of results did you get?

3. We’re having a challenge with [something within their skill set]. [Insert pertinent details]. Do you have any thoughts on how we should tackle it? (Don’t expect him or her to solve all your problems or all have all of the answers, but this is important to see what questions he or she asks and to start working on something concrete together).

Experience (and Failure) – Everyone loves to focus on success, but for every success there were a hundred failures. If this person has succeeded, he or she has most certainly failed as well. Along with experience level as an advisor, you’ll want to gauge his or her comfort level with talking about failures and ability to learn from them going forward.

1. Have you ever been an advisor before?

a) Can I talk to someone you’ve advised in the past? (This is rarely done and is insanely important).

b) What worked well for you in those relationships, and what did not?

If this person is an entrepreneur

2. If you could go back in time, what decisions would change as a startup founder?

3. What was your biggest challenge with founding your own company?

If this person is not an entrepreneur

4. Have you ever been an early employee of a company?

a) What were some of the challenges you faced there early on?

For everyone

5. Everyone has times when things went to sh*t. Tell me about one of yours and how you reacted.

Company Vision – You should know why your advisor is interested in your company. Whether for personal reasons, curiosity or something else, you want someone who genuinely cares about what you’re doing. Otherwise, he or she won’t take the time to understand and help you problem-solve. You also want someone who can successfully navigate the landscape of your industry or is insanely interested in figuring something new out.

1. You’re a busy person and you could spend your time on a lot of different things—what interests you about my company?

2. What do you see as the future for this company? (This can be a good time to see whether your vision aligns with what he or she is seeing).

3. What experience do you have with this industry in particular? What inspires you about it?

Fit – Talent, experience and vision are great, but if you can’t work well together they’re all moot. The best way to test this is…to work together. You should have at least three meetings before you sign on the dotted line. In that time you should ask these questions to see if you’re compatible.

1. What kind of communication lines work best for you? (If this person, for instance, absolutely has to meet in person every time you talk, you’ll want to find out now and see if it’s something you can do).

2. What is the most successful project you’ve worked on? Why did you enjoy it/why did it succeed? (You’re looking for whether he or she did this with others or individually, and what motivates them).

If they are an entrepreneur

3. Did you have advisors at your company?

a) If so, what worked well and why?

b) If so, what didn’t work well and why?

4. Do you prefer working in groups or one-on-one?

5. How do you want to be compensated? (You want to broach this after a few good meetings. Also note that if he or she is more focused on this than the other parts of the conversation, that’s a warning sign).

6. Two years from now, if someone asks you what you did as advisor for us, what would you want to tell him or her?

7. What piece of career or company advice do you wish someone had given you 3-5 years ago?

Time – You can find the perfect person and get along famously, but you have to make sure he or she have the time to give. Make sure your expectations of time commitment are mutual, or you’ll end up disappointed.

1. How much time can you realistically allot to us? (Per week, per month, etc).

2. Do you have a tight schedule or can you be flexible with scheduling for meetings, etc?

3. How often would you imagine meeting/talking?

Let’s be clear: this should be a conversation. Don’t go into your first meeting with a potential advisor and just run down this list of questions—that’s sure to be a turn off. But make sure you get the answers you need and cover these areas. Your first few interactions with a potential advisor are super important; you’re both trying to evaluate each other in a short period of time and there are several factors to consider. You shouldn’t just wing it!

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