TECHNOLOGY TIMES
Insider Tips To Make Your Business Run Faster, Easier And More Profitably
7 QUESTIONS
You Should Be Asking Your IT Provider Every Quarter (But Probably Aren’t)
Ifyou’reonlytalkingtoyourITprovider whenyourenewyourcontract,you’redoing itwrong.
Technologyisn’ta“setitandforgetit”partof yourbusiness.It’sconstantlyevolving,andso arethethreatsthatcomewithit.That’swhy quarterlyITcheck-insarenonnegotiableif youwantyourbusinesstostayprotected, productiveandcompetitive. Buthere’sthething: Most business owners don’t know what to ask.
So today, we’re giving you a cheat sheet. These are the questions your IT provider shouldbereadytoanswereverysinglequarter – no tech-speak, no vague promises, just straight answers that keep your business runningsmoothly.
1. Are There Any Vulnerabilities We Need To Address Right Now?
Thisisn’tjustaboutcheckingboxes.
Ask:
Isourantivirusup-to-date? Arethereunpatchedsystems? Havewehadanynearmissesorred flagslately?
You’renotbeingparanoid–you’re beingprepared.
2. What’s The Status Of Our Backups? And Have You Tested Them Lately?
Backupsarelikeseatbelts:Youdon’tthink aboutthemuntilyoureally,reallyneedthem.
Ask:
Whenwasthelasttimeyoutesteda fullrestore?
Areweusingtherightbackupstrategy? Off-site?Cloud?Hybrid? Arewebackinguptherightthings?
Iseverythingbeingbackedupand storedsecurely?
You’dbeshockedhowmanybusinessesthink they’rebackedup…untilthey’renot.
3. Are All Employees Following Security Best Practices?
Itonlytakesoneteammemberclicking thewronglinktobringthewhole networkdown
Ask:
Havetherebeenanyunusualloginsor riskybehavior?
Doweneedanotherroundof phishingtraining?
Areemployeesusingmultifactor authentication?
BonuspointsifyourITproviderbringsthis
upbeforeyouask.That’showyouknow they’rewatching.
4. How Has Our Network Performance Been? Anything Slowing Us Down?
Slowsystems=slowteams=lostproductivity (andmoney).
Ask:
Arethereanyrecurringperformanceissues? Areweoutgrowingourhardware orsoftware?
Isthereanythingwecanoptimizetospeed thingsup?
Evensmalltweakscanmakeabigdifference.
5. Are We Still Compliant With [HIPAA, PCI-DSS, GDPR, etc.]?
Regulationschange.Sodotherulesabouthow youstoreandprotectdata.
Ask:
Arewemeetingthestandardsfor ourindustry?
Haveanyrequirementschanged?
Doweneedtoupdatepolicies,softwareor training?
Finesfornoncompliancearen’tcheap.Stay aheadofthem.
6. What Should We Be Budgeting For Next Quarter?
GoodITisproactive.
Ask:
Arethereanysoftwarelicensesexpiring? Anyequipmentnearingtheendofitslife? Anyupcomingprojectsweshouldbe planningfor?
Thishelpsyouavoidsurpriseexpensesandplan likeapro.
7. What Trends In IT Or Cybersecurity Are We Behind On That Are Making Us Slower Or More Vulnerable?
Technologydoesn’tstandstill–andneither docybercriminals.
Ask:
Aretherenewtoolsorbestpracticeswe’re notusingyet?
Arewelagginingbehindinanysecurity protocolsorperformancebenchmarks? Whatareotherbusinessesoursizedoing thatwe’renot?
Arethereanyrisingthreatsthatweneedto bemorecautiousof?
Fallingbehindonemergingtrendsdoesn’tjust slowyoudown–itleavesyouexposedAgreat ITpartnerwillkeepyouaheadofthecurve, notplayingcatch-up.
You AREN’T Having These Conversations? Red Flag.
IfyourITproviderdoesn’thave clearanswerstothesequestions–orworse,iftheyaren’tofferingtomeet withyouquarterlyinthefirstplace–you mightnotbegettingthesupportyouneed
Technology changes fast. Cyberthreats move faster.
Youneedsomeone whoisnotjustreacting whensomethingbreaks butactivelyworkingto preventthebreakinthe firstplace.
MONTH
Yousetit.Youforgetit.Andjustlikethat, whileyou’repackingforvacation,yourinbox startsbroadcasting:
“I’m out of the office until [date]. For urgent matters, contact [coworker’s name and e-mail].”
Harmless,right?
Actually,cybercriminalslovetheseauto-replies. Thatsimplemessagegivesthemvaluableintel: yourname,title,whenyou’reunavailable,who tocontact,internalteamstructureand sometimeseventraveldetails.
This provides two major advantages: Timing –Theyknowyou’reunavailableand lesslikelytocatchsuspiciousactivity.
Targeting –Theyknowwhotoimpersonate andwhotoscam.Thissetsthestagefora phishingorbusinesse-mailcompromise(BEC) attack.
Businesseswithtravelingexecutivesorsales teamsareespeciallyvulnerable.Adminsoften field many requests, handle sensitive tasks tasksquicklyandmaytrustawell-craftedfake e-mail
How To Protect Your Business:
1. Keep It Vague
Skipdetaileditineraries.Instead,say:“I’m currentlyoutoftheofficeandwillrepondwhen Ireturn.Forimmediateassistance,contactour mainofficeat[info].”
2. Train Your Team
Educatestaffnevertoactonurgent,sensitive requestsbasedsolelyone-mail.Alwaysverify throughanotherchannellikeaphonecall.
3. Use E-mail Security Tools
Advancedfilters,anti-spoofingprotectionsand domainmonitoringreduceimpersonationrisks.
4. Enable MFA Everywhere
TROY SCHOOLEY
How It Happens:
Yourauto-replyissent.
Ahackerimpersonatesyouoryour alternatecontact.
Theysendan“urgent”requestformoney, passwordsordocuments. Acoworker,trustingthee-mail,complies.
Youreturntodiscoverfraudorabreach.
Multifactorauthenticationacrossallaccounts blockshackersevenifpasswordsare compromised.
5. Partner With A Proactive
IT Provider
Anexperiencedcybersecurityteamcandetect suspiciousactivityearlyandstopattacksbefore theycauseseriousdamage.
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THE HIDDEN COST OF WAITING
Why You Can’t Afford To Delay Your Windows 10 Upgrade
Ifyou’restillrunningWindows10onyour businessmachines,let’scuttothechase:The clockistickingOnOctober14,2025,Microsoft is officiallyending support for Windows 10 Thatmeansnomoresecuritypatches,nomore bugfixesandnomoretechnicalsupport.But here’s what business owners really need to understand:Thecostofwaitingisn’tjustabout somedayneedingtoupgrade.It’saboutwhat waitingcouldcostyouinthemeantime.
alreadyphasingoutsupportforWindows10.If your systems stop working mid-project or crashduringaclientdemo,what’sthatworth? And it’s not just software. New printers, peripheralsandevensecuritytoolsmaystop playingnicelywithyouroutdatedOS
3. Lost Productivity
“We’ll Deal With It Later” Is An Expensive Strategy
Wegetit–upgradingeverymachineinyour businessisn’texactlyyourideaofafunbudget item.Itfeelseasytodelay…untilsomething breaksButhere’swhatprocrastination actuallycosts:
Outdatedsystemsareslower,theycrashmore frequentlyandtheyfrustrateyourteam Even smalllagsaddupovertime,draggingdown efficiency,moraleandyourabilitytocompete. Ifeveryemployeeloses10to15minutesaday totechhiccups,whatdoesthatcostyouovera month?
4. Emergency Upgrades Are Always
Waitinguntilyoursystemscrashoryourteamis lockedoutdoesn’tjustcreatestress–itcreates panic-spendmode:
What Smart Business Owners Are Doing Now
They’regettingaheadofthedeadline,notjust byupgradingdevices,butbyusingthis transitionto:
Auditwhatdevicesneedtogo
Streamlinetoolsandsoftware
Tightenupcybersecurityprotections PlansmarterforITspendin2025
How To Make The Transition Easy
Here’swhatwerecommend:
Runacompatibilitycheck–Notallmachines canrunWindows11Findoutwhichonesneed tobereplaced.
Audit your apps –Makesureyouressential toolsarereadytorunonWindows11or newerenvironments
OnceMicrosoftdiscontinuesWindows10 updates,everynewvulnerabilitybecomesyour responsibilityHackersloveoutdatedsystems becausethey’reeasytargets.It’slikelockingthe frontdoorbutleavingthewindowswideopen Onebreachcouldcostyouthousands–orworse, yourentirebusiness
2. Software And Hardware
1. You’re Operating Without A Manybusinessapps,suchasaccountingtools, CRMsandindustry-specificplatforms,are
Emergencyhardwareorders
RushITlaborfees
Businessinterruptionswhilemachines arereplaced
Alittleplanningnowsavesalotofscrambling–andmoney–later.
5. You’re Risking Compliance
Ifyourbusinesshandlessensitivedataorissubject to regulations (HIPAA, PCI-DSS, etc.), using unsupported systems could result in fines or lawsuits Many regulatory frameworks require up-to-datesecurity–Windows10won’tmeet thosestandardscomeOctober.
Budget for hardware now –Don’tget stuckinasupplychaincrunchlater
Partner with an IT provider –Wecan handlethetransitionfromstarttofinish–no downtime,nosurprises.
Don’t Wait Until October To Panic
Waitinguntilthelastminutewillcostyoumore –inmoney,stressandmissedopportunityWe’re helpingsmallbusinessesmaketheupgradethe smart way:planned,smoothandoptimizedfor futuregrowth
Booka FREE NetworkAssessmentandwe’ll helpyouidentifywhatneedsupgrading,what canstayandhowtobuildatransitionplanthat won’tdisruptyourbusinessbeforethedeadline