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8 Questions to Ask Any Freelancer Before You Hire Them

Small businesses forÌýmany projects andÌýtasks. AÌýgreat freelancer isÌýexcellent andÌýdelivers solid content forÌýaÌýfraction ofÌýtheÌý. But many small-business owners have atÌýleast one freelancer horror story.

The trick toÌýavoiding aÌýhorror story yourself isÌýtoÌýcarefully vet freelancers before you hire them. Beyond theÌýusual questions about qualifications andÌýreferences, here are 8Ìýinterview questions toÌýask aÌýpotential freelancer!

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What IsÌýYour Ideal Client Relationship?

The answer toÌýthis question should tell you three things about aÌýpotential freelancer.

First, itÌýwill give you anÌýidea ofÌýhow much real experience they’ve had. AÌýnewly minted freelancer won’t beÌýable toÌýanswer this question because they haven’t had enough client relationships toÌýform anÌýopinion. ByÌýcontrast, freelancers with wide andÌývaried experiences will have formed not just aÌýwish list ofÌýrelationship attributes, but also aÌýset ofÌýoperating procedures that help make them aÌýreality.

Second, itÌýcan help you determine how good ofÌýaÌýmatch this freelancer’s work style isÌýforÌýyour company culture andÌýyour team procedures. Some work styles will beÌýaÌýbetter fit forÌýyour company than others.

Finally, this question helps spot freelancers who might beÌýhard toÌýwork with. Listen during theÌýanswer forÌýwhether they are willing toÌýadjust their expectations toÌýwork with aÌýclient, orÌýwhether they’re likely toÌýbeÌýdemanding andÌýinflexible.

How Many Projects Are You Working OnÌýRight Now?

Unless you’re offering aÌýtemporary full-time assignment toÌýaÌýfreelancer, it’s unfair toÌýexpect that you’ll have their undivided attention. However, many freelancers fall into theÌýtrap ofÌýaccepting all work that comes inÌýforÌýfear ofÌýmissing out onÌýincome andÌýopportunities. This question helps you gauge whether orÌýnot they have enough bandwidth toÌýtake onÌýtheÌýwork.

Unfortunately, there isn’t aÌýuniversal formula toÌýtell whether orÌýnot aÌýfreelancer has too many tasks toÌýtreat your project with theÌýattention needed. However, you can ask several follow-up questions toÌýget anÌýidea ofÌýwhether orÌýnot theÌýfreelancer feels overwhelmed andÌýhow they balance multiple projects atÌýone time.

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What Experience DoÌýYou Have With (Insert Tool Here)?

Whichever app, platform, orÌýsoftware you used toÌýcommunicate andÌýtrack workflow, you should ask aÌýpotential freelancer how much experience they have with it. IfÌýthey have noÌýexperience with that particular tool, find out how many different tools they have worked with.

For example, ifÌýyou are hiring aÌýfreelancer toÌýhelp you with your 51ÊÓÆµ store orÌýhelp manage your business. They should have aÌýbackground inÌýe-commerce terms, programs, andÌýtools.

Ideally, aÌýcandidate will have extensive experience with theÌýtools your team uses onÌýaÌýday-to-day basis. Alternatively, aÌýcandidate who has experience with enough platforms should have noÌýproblem learning anÌýadditional one.

That said, most freelancers are good atÌýpicking upÌýnew systems andÌýtasks. It’s one ofÌýtheÌýcore competencies ofÌýsuccessful freelancing. It’s best toÌýconsider this question aÌýtie-breaker between two candidates with similar qualifications, rather than aÌýdeal-breaker.

How Would You Prefer WeÌýMeasure Your Results?

This isÌýaÌýweeding-out question. IfÌýtheÌýcandidate isÌýconfused byÌýtheÌýquestion orÌýappears toÌýbeÌýmaking upÌýanÌýanswer off theÌýtop ofÌýtheir head, they’re probably not theÌýbest option forÌýtheÌýjob. Not understanding that results should beÌýmeasured, orÌýbeing unfamiliar with theÌýconcept, indicates they’re not professionally ready forÌýyour project.

IfÌýaÌýcandidate gives aÌýknowledgeable, detail-oriented answer, they’re most likely worth considering. ItÌýdoesn’t really matter what theÌýanswer is, asÌýlong asÌýthey’re willing toÌýalter how they measure results toÌýmatch theÌýmetrics andÌýanalytical tools you use. What’s important here isÌýthat they understand theÌýimportance andÌýtheÌýbest practices ofÌýobjectively measuring performance.

AsÌýaÌýbonus, theÌýanswer toÌýthis question gives you aÌýhead start onÌýfinalizing project details with whichever candidate you ultimately decide toÌýgoÌýwith.

What Happened theÌýLast Time You Missed aÌýDeadline?

Everybody misses deadlines once inÌýaÌýwhile. You do. Your team does. Your company does. It’s not fair toÌýdisqualify every potential freelancer who admits toÌýhaving missed aÌýdeadline. Instead, this question isÌýabout how well theÌýcandidate solves problems andÌýhow honest they are.

IfÌýaÌýfreelance candidate with more than three years ofÌýexperience tells you they’ve never, ever missed aÌýdeadline, they may have anÌýhonesty issue. AtÌýtheÌývery least, you need toÌýcheck with their references toÌýconfirm this track record.

When aÌýcandidate admits toÌýmissing aÌýdeadline, listen forÌýhow they handled theÌýsituation. DoÌýthey acknowledge their role inÌýmissing theÌýdeadline, orÌýdoÌýthey blame everybody else? DoÌýthey have aÌýpersonal plan inÌýplace forÌýfinishing work quickly ifÌýthey miss aÌýdeadline? Are they cavalier about deadlines inÌýgeneral? Listen toÌýtheÌýsubstance ofÌýtheÌýanswer, asÌýwell asÌýtoÌýhow they talk about deadlines andÌýtimelines inÌýgeneral.

What Else DoÌýYou DoÌýforÌýWork?

Most questions you want toÌýask candidates, whether forÌýregular employment orÌýaÌýfreelance arrangement, should beÌýopen-ended, with noÌýclear right orÌýwrong answer, asÌýaÌýway toÌýgather information. This isÌýnot one ofÌýthose questions.

There are two kinds ofÌýfreelancers: professionals who rely onÌýfreelance work forÌýtheir full-time living, andÌýthose who doÌýaÌýbit ofÌýfreelance work onÌýtheÌýside forÌýextra money. IfÌýtheÌýcandidate has aÌýfull-time job, their work forÌýyou will beÌýaÌýsecond, third, orÌýeven fourth priority.

That’s not toÌýsay part-time freelancers with talent andÌýpotential don’t exist. But most will beÌýmore problematic than those who treat their freelancing asÌýaÌýfull-time profession. IfÌýyou find aÌýpart-timer who otherwise checks all ofÌýyour boxes, give them aÌýshot, but set workflow andÌýaÌýcontract that makes certain you stay top ofÌýtheir priority queue.

Why DoÌýYou Freelance?

The best professionals inÌýanyÌýfield are those who got there onÌýpurpose andÌýwho value their position. They are passionate andÌýmotivated because they doÌýwhat they doÌýforÌýwell-understood reasons.

IfÌýyou asked multiple freelancers why they freelance, you would get anÌýarray ofÌýanswers. Some ofÌýthese answers suggest aÌýparticular candidate will beÌýexcellent, while others are bright red flags.

The answers you’re looking forÌýwill center around how much theÌýperson cares about freelancing. They will tell you ifÌýtheÌýcandidate isÌýknowledgeable about theÌýtype ofÌýwork you need. Suppose you need extra help managing your business, whether itÌýbeÌýmarketing orÌýe-commerce. Make sure theÌýfreelancer shares theÌýsame passion forÌýyour business!

IfÌýyou get answers about how easy freelancing is, orÌýhow theÌýcandidate just “sort ofÌýfell into” theÌýjob, consider other applicants. IfÌýtheÌýcandidate doesn’t care very much about their own freelancing business overall, it’s unlikely they will care about your particular place inÌýit.

How DoÌýYou Manage Your Freelancing Business?

Much like theÌýquestion about measuring performance, this question reveals theÌýprofessionals inÌýyour candidate pool. AÌýprofessional freelancer spends time onÌýmanaging their freelance business. They think andÌýcare about theÌýbusiness aspects ofÌýtheir career. Such aÌýfreelancer will beÌýable toÌýanswer this question briefly andÌýintelligently.

IfÌýaÌýcandidate doesn’t have anÌýanswer toÌýthis question orÌýseems unprepared toÌýanswer it, it’s anÌýindication ofÌýaÌýlack ofÌýprofessionalism. IfÌýthey don’t manage their business well, they’re unlikely toÌýmanage yours anyÌýbetter.

Among theÌýapplicants who doÌýhave aÌýstrong answer toÌýthis question, look forÌýthose with management practices that best match your company’s. There are many right ways toÌýmanage aÌýfreelancing business, but some ofÌýthose ways are better suited toÌýworking with how you run your company.


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Bonus Question

This final question isn’t forÌýtheÌýfreelancer themself, but forÌýtheÌýreferences they give you. Ask each reference ifÌýthey know anybody else who has worked with that freelancer. Most candidates will give you theÌýreferences who are happiest with their work (or are related toÌýthem orÌýfriends). This isÌýwhat scientists call aÌý“selection bias,” andÌýitÌýmay orÌýmay not reflect theÌýmost common experience with that freelancer.

But ifÌýyou ask forÌýother people who’ve worked with them, andÌýthen ask those people forÌýmore names, eventually you’ll get aÌýsense ofÌýtheÌýaverage experience. That’s theÌýinformation you want toÌýbase your final decision on.

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About The Author
Robert Tulley is a former human resources manager at a Fortune 500, where he used to hire freelancers, part-timers, and full-time staff members. Now, he’s on the other side of the equation and freelancers for numerous companies.

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