How to work with mentors and advisors

Musings of a Product Guy

One of the things I love doing is mentoring and advising startups. Mentoring at 500 Startups and StartX has been a great experience — allowing me to meet many great founders, learn about new spaces, and keep myself sharp on the latest industry trends. It’s also led me to becoming an advisor at two great companies — Floqq (online education for Latin America) and POPAPP (simple app prototyping), with more to come.

Over this time, I’ve gathered a few insights on what startups and entrepreneurs should be looking for in potential mentors and advisors.

Know what you’re looking for

Mentors and advisors come in all shapes and sizes. Some have more operating experience, others more investing. Some have started companies, others are working at larger ones. Some have engineering experience, others product, design, marketing, or business development.

Therefore, it’s incumbent on you, the entrepreneur, to know what you’re looking for from a mentor or advisor. Do you need technical help? Product help? Investment help? Partnership help? Leadership help?

For instance, say you’re looking for some help on how to scale a B2B sales organization. While I can obviously provide my thoughts here based on my experience working with several startups as well as from people in my network network, you’d be well served finding an advisor who has more direct experience here (either as a founder or as a sales executive).

Make sure you know WHAT you want advisors to help you with, and target those people accordingly.

Surround yourself with a board of different advisors

Once you determine WHAT you are looking for help with, surround yourself with a board of advisors that meet that criteria but have a wide array of experience and expertise. I think the advisor board structure works well here. For smaller, specialized decisions, you should rely on specific advisors. But for larger decisions, it is good to have a group with various backgrounds and points of view to provide input (while obviously heavily relying on the most relevant advisor’s opinion).

Clearly define expectations

Oftentimes the best advisors and mentors have full-time jobs outside of advising. They are working at companies or as a full-time investor — or even running their own company.

As a result, it’s important to clearly define expectations for your relationship as early as possible. If you need an advisor who can spend 20 hours a week with your company, it’s going to be hard if they are also running their own startup — however, if this is what you feel you need, it’s important to set this expectation up front to determine if the advisor can deliver. Alternatively, if an advisor is looking for a company to go deep and spend a lot of time with, but you’re looking for a one hour board commitment a month, this is also a different type of relationship.

As early as possible, make sure to set expectations so that both sides can ensure that they can deliver. And also define HOW you will work with the advisor — email, phone, in person, board meetings, etc. HOW you work with the advisor is just as important as how often you interact with him or her.

Know your advisor’s strengths and weaknesses

Some mentors and advisors are better at different points in the life of a company. For instance, a former entrepreneur might be better in the early stage of your company to help you find and pitch angel investors and help you structure your leadership team. However, as you get larger, perhaps you may need someone who knows how to scale a sales organization — and this may be a person with a different background.

That’s OK. Advisory boards often change throughout a company’s lifecycle as different experts are needed at different stages. This is why I’ve often seen advisor relationships structured to last two years, less than say the average of a four year vesting structure for employees, as the expertise needed by the company often changes. (I should note that four years is definitely acceptable and used in many advisory relationships when the fit is right, but it tends to be less common than two.)

So just make sure you recognize your advisor’s strengths and weaknesses, and be up front with him or her when what you need from an advisor changes — we just want to help!