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What to ask a prospective client and advice for a freelancer caught in a client's love triangle. 

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Freelance FAQ: What questions should I ask a client?

When you first meet a client, you need to:

• Determine if the prospect is a good fit
• Diagnose their problem
• Decide if this will be a mutually beneficial relationship

Don’t overwhelm your prospect with 1,001 questions in the initial email, but do ask them sooner than later.

From there, you need to determine:

• Budget: Can the client afford your services?
• Authority: Does this person have the authority to make buying decisions?
• Need: Does the client have a genuine need for your services?
• Timeline: Does the timeline work for you and your client?

I always try to figure out the negative consequences of not having a solution and the positive implications of having a solution to frame all future conversations.

Regardless, here are some general questions to ask a prospect or client:

• For what reasons are you looking to hire a new freelancer now?
• What triggered your decision to hire a freelancer?
• What’s made this so urgent or important?
• What experiences, good and bad, have you had with other freelancers? What do you want to be different this time around?
• What results do you expect to see from the work we do together?
• What are your company’s goals?
• What’s your most important priority? What’s your most urgent priority? If they’re not the same, ask: What will it take to focus on the most important priority? How can the urgent priority get downgraded? What’s your company’s biggest marketing challenge?
• What’s keeping you from overcoming or meeting that challenge?
• What internal resources do you have to apply to this challenge?
• How well are your competitors doing?
• What are your competitors doing that you’re not and wish you were?
• What do you want to be the best at? What do you want your company or department to be renowned for?
• What are you willing to stake your reputation on?
• What’s the average lifetime value of a customer?
• What’s your customer acquisition cost?
• What’s your current marketing return on investment?
• What’s your process for choosing a consultant or agency? Have you used this process before? What worked or didn’t work? What will you do to get a different result?
• Who’s involved in making the decision? Who signs the contract?
• If you don’t hire a freelancer or consultant, how will you meet this challenge? What will you do?
• How will you know we’ve been successful?
• If we don’t address this issue, what will it cost your company?
• If we deliver on agreed upon goals, what’s that worth to your company?
• What problems do you see down the road that could obstruct or constrain our working together?
• What makes you lose sleep at night? Or what do you need so you can sleep at night?

You may have field-specific questions that you find your regularly asking clients. Based on those repeat findings, you should create an onboarding questionnaire that you go through with clients when they first engage you.

Feedback from the Inferno: How do I deal with my client’s controlling boyfriend?

(This segment originally premiered over at The Freelancers Union.)

My client’s boyfriend insists on attending all of our meetings, business or otherwise.

For context, I’m a male, and my client is a female. We know each other from school, but we recently reconnected when she found out I started freelancing, and she wanted me to build her budding businesses’ website.

My client has insisted that this isn’t a big deal – the boyfriend should be treated as another source of feedback – but the dynamic makes me uncomfortable. I told her that she doesn’t have to worry about me trying anything, but she says that’s not really the issue. She insists that the boyfriend has “her best interests” in mind and just not to worry about it because she “really wants to work with me on this.”
What should I do?

– A third-wheel freelancer

I had to email this submitter back to glean a bit of additional context.

To summarize: the client and her boyfriend have both cheated on one another, and the boyfriend is not there for his business expertise; the client and the submitter hooked up once “while drunk at school”; by school, the submitter means he and his client attended university together.

One thing that immediately set off warning signs for me is that you’re having meetings with this client that fall under the umbrella of “otherwise.”

Working with friends is something that I probably wouldn’t recommend. Working with a former hookup is something I would almost always discourage. Working with a serial cheater (that you have a history with!) while she’s in a troubled relationship (with a controlling boyfriend!) sounds like the motive the detective will give when he finds your dead body.

Point being: none of this sounds like a good idea.

Even if you weren’t involved with this client on the pretense of this being a client-freelancer relationship – and I’m not convinced you wouldn’t be, as you failed to mention you had sex with this client in the past in your initial email – I would still encourage you to get as far away as possible.

It sounds like this client needs to separate their personal and professional life. And I think the same could be said about you.

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