I often get asked by startups, “We’re thinking of working with a celebrity to help market our product. What do you think? And how should we approach it?”.

The short answer is, it depends entirely on the nature of your product, your expectations of what the celeb will do for you, and your budget. To help you decide whether hooking up with a celeb is the right move for your business, here are the questions you need to ask yourself:

Which celebrity best hits your target market?

The basic idea behind celebrity endorsements is that they increase awareness and engagement within your target market. So it stands to reason that you should partner with a celebrity who hits your target market. This sounds obvious but you would be amazed how many celebrity endorsements are a result of straight up starf-cking by some exec trying to impress his kids, with little attention paid to the data. Talent agents know this and are masters at leveraging it into seven figure paydays for their clients, so when it comes to picking a celeb, don’t go with your heart, go with the data. There are three good sources:

• Use a service like qscores, which is kind of like a Nielsen for personalities – they measure the appeal of a celeb within a target market.
• Look at the Insights report on the celeb’s Facebook page. Obviously, you’ll need to ask their page admin for this.
• Look through the Facebook and Twitter profiles of users who are liking/commenting on a celebrity’s posts. Its a good indicator of who their most active fans are.

Will the celebrity want to endorse your business?

To some degree, all celebrities view endorsements as selling out – and view selling out as anti-correlated to success in their day job (Yes, even the Kardashians). So its important to understand how the sensitivities vary for different categories of celebs:

• Actors are the most sensitive because they live in constant fear of never working again and believe that endorsements make them less believable/appealing to fans. Its why A-list Hollywood actors prefer to do ads overseas rather than in the US (think Lost In Translation). If you want to work with an actor, you’ll have more success with a TV or comedic actor in their first season on a breakout show, when they aren’t getting paid that much, aren’t sure whether the show will get renewed and are trying to capitalize on their newfound fame.
• Professional athletes are the least sensitive because a) they generally have  long term contracts with their teams and b) they know anything they do off the field doesn’t matter as long as they deliver on game day. Many athletes are actually surprisingly cash poor because they have their salaries deposited into managed accounts – from which they get an allowance to protect them from blowing it all at once – so they look at endorsements as “walking around” money.
• Musicians are generally pretty easy to work with, unless they are in the middle of launching a new album or a new tour, in which case they will already have a bunch of sponsors lined up.
• Reality TV stars will generally do anything for money and in many cases will value the credibility they gain from endorsing a business.

The other dimensions to consider are amount of exposure (i.e. internet only, TV, personal appearances), length of endorsement period, exclusivity and amount of actual physical work required by the celeb (i.e. do they have to show up to a photo shoot or make personal appearances out of town). Any of these could be a deal breaker for the celeb.

What is your plan for contacting the celebrity?

Unless you know the celebrity directly, you will have to go through some kind of intermediary. Here are the options, in order of preference:

1. Manager: This is the best person to talk to. They are generally business-minded and can tell you exactly what their client (who is often a close friend) will or won’t do and for how much money. Think of the manager as the COO of the celeb’s business.
2. Stylist: If you want a celeb to wear your products to an event, or to be photographed wearing them, your best bet is to hit up their stylist. Most stylists are in LA or NY and are fairly easy to track down.
3. Publicist: Publicists are a good way in because they generally don’t make a commission off the celeb’s earnings and are viewed by the celeb as someone who will not put the celeb into a compromising situation.
4. Lawyer: Lawyers tend to have long term relationships with their clients and are trusted advisors.
5. Agent: These are the easiest people to reach, as their job is to generate revenue for their clients. The flip side is that they will probably try to sell you a consulting engagement to “introduce you to a bunch of people around town”. In many cases they also still have to go through the manager, which means you are now working with two intermediaries.

How will you convince the celebrity to endorse your product?

Assuming you can sell the celebrity on the benefits of endorsing your product, you’ll inevitably end up talking turkey. In Hollywood, its simple: Money talks, bullshit walks – simply because there are so many polished bullshitters running rampant through the industry. Here are some things to consider when structuring the deal:

• Cash is king: It gives you the most leverage to ensure the services you need performed actually get done. You’ll be surprised how much you can get most mid-tier talent to do for $10-20,000.
• Equity is more complicated: You’ll argue valuation; you’ll need to draft a custom agreement; you’ll need approval from your board to issue stock. Only recommended if your company is extremely hot.

What else?

If you get through all of the above and net out that a celebrity endorsement is a good idea for marketing your business, remember that you will still need to pay for any direct media costs above and beyond the payments to the celebrity for their endorsement. It can substantially impact your overall customer acquisition costs.

I’ve asked these questions at least a couple of hundred times in interviews for all types of roles, from sales and biz dev to product and engineering and everything in between. I’ve consistently found them to be extremely good predictors of whether a candidate will be successful in the role.

1. When was the time you were most passionate about what you were doing?

I like this question because it cuts through the bullshit of prepared answers, gets the candidate to open up and eliminates the need for hiring manager and candidate to labor through an entire resume during an interview. As a hiring manager I’ve found it crucial to understand up front what kind of work excites my staff, so that I can give them work that makes them happy and productive. Let’s face it, everybody has had jobs they liked and jobs they didn’t, so this question really helps both the candidate and hiring manager quickly figure out if the role at hand is going to be the right fit.

2. What’s the biggest misconception that people have about you?

I like this question because it tests a candidate’s self awareness. A candidate who has trouble answering this question will have trouble fitting into the type of non-hierarchical, highly collaborative culture that is common in today’s knowledge-based workplaces. If a candidate says “I really don’t think there are any misconceptions about me”, its probably time to end the interview early.

3. What’s your favorite movie?

I like this question because it tests the candidate’s ability to think on their feet and quickly form an opinion. This is essential in fast moving industries, where we don’t always have the time to gather and analyze every piece of data and create that perfect powerpoint preso. In answering this question, it doesn’t really matter which movie the candidate likes, what matters it that they can quickly pick a movie and subsequently defend why they like it.

4. What’s the biggest mistake you’ve made that you don’t regret?

I like this question because it demonstrates whether the candidate is aware of what they’ve learned from their past mistakes. Everyone makes mistakes at work, its impossible not to given the pace at which markets move. A candidate who gives a good answer here is one who is not going to get discouraged when the company hits a rocky spot, rather is going to look at it as an opportunity to develop further.

5. If you joined us as <insert job title> tomorrow, what would you like to have accomplished in 3 years?

I like this question and usually leave it to last because it tests how much the candidate has thought about what they can really contribute once they are in the door. Many candidates focus way too hard on impressing the hiring manager with their own achievements and way too little on what the job itself entails. Getting a job is a little like getting married – its less about the wedding and more about the marriage itself. If they can’t seen themselves in the job they aren’t going to hit the ground running once you hire them.