10 Questions to Ask Before Hiring a Dog Walker

You've found a potential dog walker. Maybe you scrolled through profiles until your eyes glazed over. Maybe a neighbor recommended someone. Maybe you used a matching service that did the initial vetting for you. Either way, you've got a meet-and-greet scheduled—and now you're wondering what to actually ask.

Here's the thing: the meet-and-greet is a job interview, and your dog's wellbeing is the position. Most people treat it like a casual introduction—"nice to meet you, here's where we keep the treats, see you Monday." But that approach leaves you with no idea whether this person can actually handle your dog in real-world situations.

The questions you ask reveal everything. They separate professional walkers from people who "just love dogs." They expose who's prepared for emergencies and who's winging it. They tell you whether someone understands your dog's specific needs or plans to treat every dog the same way.

Below are the 10 questions you should ask—and what to listen for in the answers.

The 10 Essential Questions

1. "How long have you been walking dogs professionally, and what's your background?"

Why it matters: Experience isn't everything, but it's something. A walker with years of experience has likely encountered difficult situations—reactive dogs, sudden health issues, escape attempts—and learned how to handle them. Background matters too: someone who trained at a reputable dog walking company learned protocols; someone who started solo may have developed their own (for better or worse).

What to listen for:

• Specific timeframes ("I've been doing this professionally for three years, full-time for two")
• Professional context ("I started at a dog walking company, got my CPDT-KA certification, then went independent" or "I worked at a vet clinic for two years before transitioning to walking")
• Continuing education ("I completed Fear Free certification last year" or "I take Karen Pryor Academy webinars")
• Acknowledgment of learning curve ("My first year, I made mistakes—I learned to never use retractable leashes after one incident")

Red flag: Vague answers like "I've always loved dogs" or "I've been around dogs my whole life." Loving dogs and professionally walking them are different skill sets. Also watch for defensive responses ("Why does that matter?")—professionals are proud of their experience.

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2. "What types of dogs have you worked with? Have you handled dogs like mine?"

Why it matters: Not all dogs are the same. A walker who's only handled calm, small dogs may struggle with your 80-pound Lab who pulls like a sled dog. Breed experience, size experience, and behavioral experience all matter—someone who's walked 50 Golden Retrievers might never have encountered a brachycephalic breed that overheats at 75°F or a sighthound with zero recall instinct.

What to listen for:

• Range of breeds and sizes with specific examples ("I regularly walk everything from Chihuahuas to Great Danes. I have three clients with Pit mixes who are strong pullers.")
• Experience with your dog's specific breed or type ("I've worked with several Huskies—they need mental stimulation, not just distance")
• Understanding of breed-specific needs ("I know brachycephalic breeds like Bulldogs and Pugs need shorter walks and constant overheating monitoring—I carry a Gulpy water bottle and know the signs of heat stroke")
• Behavioral complexity ("I've handled leash-reactive dogs, fearful dogs, and dogs with resource guarding. Each requires different approaches.")

Red flag: "I can handle any dog" without specifics. Confidence is good; overconfidence without evidence is concerning. Also concerning: someone who's never encountered challenging behaviors but claims to be experienced.

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3. "Have you dealt with leash-reactive dogs? Walk me through how you handle reactivity."

Why it matters: Even if your dog isn't reactive, they'll encounter reactive dogs on walks. In Chicago specifically, crowded sidewalks on Division Street, Milwaukee Ave, and around Wicker Park mean constant dog encounters. A professional walker knows how to manage their own dog and navigate around triggers safely. If your dog IS reactive, this question is make-or-break.

What to listen for:

• Specific techniques with names ("I use threshold training—keeping enough distance that the dog can still think, usually 20+ feet for moderate reactivity")
• Proactive management ("I cross the street early when I see a trigger approaching—before my dog notices, not after")
• Understanding of trigger stacking ("I know three small stressors can add up. If we've had a loud truck and a skateboarder, I shorten the walk")
• Familiarity with tools: front-clip harnesses (Freedom, Balance), head halters (Gentle Leader, Halti), treat pouches for rapid reward delivery
• Named protocols ("I use the 'Look at That' game for counter-conditioning—rewarding calm acknowledgment of triggers")
• Acknowledgment that reactivity is managed, not cured ("Reactivity management is ongoing. I don't promise to 'fix' a dog—I manage their environment to keep them under threshold.")

Red flag: "I just hold the leash tight and wait for them to calm down." That's called flooding, and it makes reactivity worse. Also concerning: "I've never had a dog react on me"—either they're lying, inexperienced, or don't recognize the early warning signs.

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4. "What's your emergency protocol if something goes wrong?"

Why it matters: This question reveals whether someone has actually thought through worst-case scenarios. Dogs get loose. Dogs get hurt. Dogs get into fights. Dogs eat something toxic. You need someone who has a plan—not someone who'll panic and call you while your dog bleeds.

What to listen for:

• A clear chain of actions with priorities ("First I secure the scene and prevent further injury. Then I assess—is this bleeding I can manage, or do we need emergency care immediately? I call you while I'm already heading to the vet if it's serious.")
• Specific Chicago emergency vet locations ("I know MedVet Chicago in Lincoln Park is 24/7. For the West Loop, I'd go to Chicago Veterinary Emergency Services. I have addresses saved in my phone.")
• Transportation plan ("I drive and always have my car nearby, so I can get to an emergency vet within 15 minutes from most of my walking areas")
• Decision-making framework ("For non-emergencies—minor cuts, bee stings, an upset stomach—I contact you first. For true emergencies—GDV symptoms (bloating, retching without producing anything), severe bleeding, seizures, collapse—I act immediately and call you on the way. GDV can be fatal within hours; I'm not waiting for a callback.")
• Poison protocol ("If a dog eats something toxic—chocolate, xylitol gum, rat poison bait—I call ASPCA Poison Control (888-426-4435) immediately for guidance while heading to the emergency vet")

Red flag: Hesitation, vague answers like "I'd figure it out," or "that's never happened to me." Emergencies happen to everyone eventually. "I'd call you first no matter what" is also concerning—in a true emergency, seconds matter.

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5. "How many dogs do you walk at once, and how do you decide which dogs can walk together?"

Why it matters: There's a big difference between one-on-one walks and group walks. Both can work, but they serve different purposes—and group walks require significantly more skill and careful matching. A solo walker with six dogs can't effectively manage a sudden reactive encounter.

What to listen for:

• Specific numbers with reasoning ("I cap at 3 dogs per walk because I need one hand free and can't give proper attention to more. For reactive or senior dogs, I only do solo walks.")
• Matching criteria ("Before adding a dog to a group, I do a separate intro walk. I match by energy level and play style—I won't put a fearful senior with a rambunctious adolescent.")
• Acknowledgment that some dogs shouldn't be grouped ("Dogs with leash reactivity, resource guarding, puppies under 6 months, seniors with mobility issues, and dogs with medical needs all get solo walks. No exceptions.")
• Van/transport considerations if applicable ("I transport dogs in secure crates in my vehicle—never loose in a car together")

Red flag: "As many as I can fit in my schedule" or group sizes of 6+ dogs. Large packs mean your dog becomes just another body in a crowd. Also concerning: "I put them together and they figure it out"—that's how fights happen.

Walk Type	Ideal Group Size	Best For	Red Flag Size
Solo walk	1 dog	Reactive dogs, seniors, puppies, medical needs, high-value clients	N/A
Small group	2-3 dogs	Social dogs matched by energy/play style	4+ without matching
Large group	4+ dogs	Not recommended—attention too diluted	Any without strict criteria

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6. "What's your typical route like, and how do you decide where to go?"

Why it matters: Experienced walkers don't just wander randomly. They plan routes based on the dog's needs, energy level, environmental factors, and safety considerations. In Chicago, route planning is especially critical given traffic, weather extremes, and neighborhood variations.

What to listen for:

• Awareness of your specific neighborhood ("In Lincoln Park, I avoid Wiggly Field at noon—too crowded—and stick to the quieter paths near North Pond. For reactive dogs, I use side streets rather than Armitage.")
• Flexibility based on conditions ("On days above 85°F, I stick to shaded routes and skip pavement entirely—grass and dirt only. On humid days, I keep brachycephalic breeds to 10-15 minute potty walks, not real exercise.")
• Consideration of your dog's needs ("For a senior dog with hip dysplasia, I choose flat terrain with multiple rest spots. For a high-energy Border Collie, I incorporate structured heel work and direction changes for mental stimulation, not just distance.")
• Avoidance strategies ("I know which yards on my routes have aggressive dogs behind fences. I avoid construction zones, the 606 Trail when it's busy with bikes, and Lower Wacker in winter—the wind tunnel effect is brutal.")
• The Hawk awareness ("In January, I plan north-south routes to minimize exposure to lake-effect wind on east-west streets")

Red flag: "I just go wherever the dog wants." That's not walking—that's following. A professional guides the walk with purpose. Also concerning: no awareness of your specific neighborhood's challenges.

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7. "Do you carry insurance? What kind and how much?"

Why it matters: Accidents happen. If your dog bites someone, damages property, or gets injured in the walker's care, you need to know who's liable and what's covered. Professional walkers treat this as a business—and businesses carry insurance.

What to listen for:

• Confirmation of liability insurance (protects against damage your dog causes to others) with specific coverage amounts ("I carry $1 million in liability coverage through Pet Sitters International / Pet Care Insurance")
• Information about bonding (protects you against theft or property damage by the walker) ("I'm bonded for $10,000")
• Care, custody, and control coverage (covers your dog if they're injured while in the walker's care—not all policies include this)
• Clear answers about what's excluded ("My policy doesn't cover pre-existing conditions or elective procedures, but it covers injuries during walks and accidents at my home")
• Willingness to provide documentation ("I can email you my certificate of insurance")

Red flag: "I don't have insurance—nothing's ever happened." That's not a plan; that's gambling with your assets. If their uninsured dog-walking results in a bite, you could be on the hook. Also concerning: "I think I have insurance through the app"—they should know their coverage details.

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8. "How will you communicate with me during and after walks?"

Why it matters: When you're not there, communication is your window into your dog's day. You want to know how the walk went, not wonder what happened. The 3-text rule is a good benchmark: if a walker doesn't respond to messages within 3 hours during work hours on 3 separate occasions, they're not communicative enough.

What to listen for:

• Specific update cadence ("I send a photo and brief note after every walk—arrival time, departure time, bathroom activity, any observations")
• Platform used ("I use Time to Pet which shows GPS tracking of the route and sends automated check-in/checkout notifications" or "I use Scout for scheduling and reports")
• Responsiveness expectations ("I respond to texts within 2 hours during my work day, 9am-6pm")
• What they'd proactively communicate ("I'd let you know if your dog seemed off—limping, excessive panting, not wanting to walk, refusing treats. I'd mention if they ate something, had loose stool, or had an unusual interaction with another dog.")
• Red flag behavior they'd report ("If your dog shows new behaviors—sudden fearfulness, aggression, reluctance to leave the house—I'd want to discuss it. These can indicate pain or illness.")

Red flag: "I'll let you know if there's a problem." Silence-is-good is a passive communication style. You want proactive updates, not just crisis alerts. Also concerning: "I don't do photos" or "I'll text when I can."

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9. "What would you do if my dog got loose?"

Why it matters: This is the nightmare scenario. A dog slipping their collar, bolting through a door, squeezing through a gap in a fence. How someone answers reveals whether they've imagined this situation and prepared for it—or whether they'll freeze.

What to listen for:

• Prevention focus first ("Before every walk, I do the two-finger check on collars and harnesses—if I can fit more than two fingers underneath, it's too loose. I use a martingale backup collar for escape artists. I never drop leashes.")
• Immediate response plan that avoids common mistakes ("I stay calm. I never chase—that triggers prey drive and makes them run faster. I crouch down, face sideways, and use high-value treats (I always carry freeze-dried liver). I call their name once in a happy voice, not frantically.")
• Tech awareness ("I'd immediately ask if you have a Fi collar or Whistle GPS—if so, I can track them in real-time. I'd also check if the microchip is registered to your current address.")
• Practical steps ("I'd call you immediately while following at a distance. If I lose sight, I'd contact local Facebook lost pet groups—Lost Dogs Illinois is most active. I'd also notify nearby neighbors and put up 'LOST DOG' posts at eye level, not high.")
• Neighborhood familiarity ("I know which direction dogs usually head in Lincoln Park—toward the lake, following the green space. I know the unfenced areas where they might end up.")

Red flag: "I've never lost a dog." Pride without a plan. Escapes happen to experienced walkers too—equipment fails, dogs panic, gates get left open. What matters is what they do next. Also concerning: "I'd chase them until I caught them"—this is the worst response.

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10. "Tell me about a difficult situation you've handled and what you learned from it."

Why it matters: This open-ended question reveals depth of experience and problem-solving ability. Anyone can handle an easy walk on a pleasant day. Professionals have stories because they've been tested—and they've learned from those tests.

What to listen for:

• A specific, detailed story with clear timeline ("Last winter, I was walking a senior Lab mix when she suddenly refused to put weight on her back left leg. I...")
• What they actually did ("I carried her to a nearby bench, examined the paw for ice balls or cuts, found nothing visible. I called the owner, described the symptoms. We agreed I'd carry her the two blocks back home rather than risk further injury.")
• What they learned ("I learned to always check paws proactively in winter, not just when there's a problem. Now I apply Musher's Secret before walks and check between toe pads every 10 minutes. Turns out she had early hip dysplasia we didn't know about—the cold made it worse.")
• Honesty about what was hard ("I was scared. I didn't know if it was a minor strain or something serious. But I knew that walking on it could make it worse, so I made the conservative call.")
• Acknowledging mistakes ("Early in my career, I underestimated a dog's reactivity range and got too close to a trigger. The dog lunged and I lost control of the leash for a second. Now I default to 30+ feet for any dog with reactivity history.")

Red flag: No stories at all, or stories where they're always the hero with no lessons learned ("I just knew exactly what to do"). Everyone makes mistakes; what matters is whether they grew from them. Also concerning: blaming the dog or owner in every story.

The Answers You Should Actually Receive

Here's a quick reference for what solid answers sound like versus what should give you pause:

Question	Strong Answer Signals	Weak Answer Signals
Experience	Specific years, certifications (CPDT-KA, Fear Free), professional trajectory	"I've always loved dogs"
Dog types	Range of breeds, specific examples, breed-specific knowledge	"I can handle anything"
Reactivity	Named protocols (Look at That, threshold training), specific tools, trigger stacking awareness	"I hold tight and wait"
Emergency	Clear steps, Chicago vet locations, GDV/poison awareness	"I'd figure it out"
Group size	Specific limits with matching criteria, solo walk categories	"As many as I can"
Routes	Your neighborhood knowledge, weather protocols, avoidance strategies	"Wherever the dog wants"
Insurance	$1M+ liability, bonding, can provide certificate	"Nothing's ever happened"
Communication	Named app, specific cadence, proactive reporting	"I'll call if there's a problem"
Loose dog	Prevention (two-finger check), no-chase protocol, GPS/microchip awareness	"Never happened"
Difficult situation	Specific story with lessons, honest about learning curve	"I always know what to do"

What If You Don't Want to Do All This?

Here's the truth: asking these questions takes time. Evaluating the answers takes judgment. And if you're hiring a dog walker because you're already stretched thin, adding "become an expert interviewer" to your plate feels like a cruel joke.

This is exactly why we built Tails.

Every walker on our platform has already answered these questions—and proven their answers with demonstrated experience. We verify skills through in-person interviews, not just background checks. We know who handles leash reactivity with proper threshold protocols, who's experienced with IVDD and hip dysplasia mobility management, who knows your specific Chicago neighborhood's parks and pitfalls.

When you use Tails, you're not starting from scratch. You're meeting walkers who've already passed the interview. The meet-and-greet becomes about chemistry and fit, not interrogation and evaluation.

You still ask questions—we encourage it. But you ask them knowing the fundamentals are already covered.

Your Pre-Meeting Checklist

Before the meet-and-greet, prepare:

Information to share:

• Your dog's daily routine and schedule
• Behavioral quirks, fears, and triggers (specific: "reactive to bikes within 15 feet," not just "sometimes nervous")
• Medical needs and medications (bring the bottles to show dosing)
• Emergency vet contact and pre-authorization for emergency care
• Your preferred communication style

Documents to request:

• Proof of insurance (certificate of liability)
• Business license (if applicable in your area)
• 2-3 references from current clients (not family/friends)

Observations to make during the meeting:

• How the walker interacts with your dog (forcing vs. letting dog approach)
• Your dog's body language around them after 10+ minutes
• Whether they ask good questions back
• How they handle the leash if you let them walk your dog briefly

Making Your Decision

After the meet-and-greet, trust your gut—but verify with your notes. A walker who answered every question confidently, showed genuine expertise, and connected well with your dog is worth booking.

A walker who seemed uncertain, rushed through your questions, couldn't name specific protocols or tools, or didn't engage with your dog's specific needs? Keep looking. "Good enough" isn't good enough when it's your dog.

The right walker is out there. Whether you find them through your own research or let Tails do the matching, don't settle for "probably fine." Your dog deserves someone who's actually prepared.

Ready to skip the interview prep? Find a pre-vetted walker on Tails and meet walkers who've already passed the test.

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Frequently Asked Questions

Should I trust my dog's reaction during the meet-and-greet? Yes—with context. Dogs are intuitive, but some dogs are nervous around all strangers initially. Watch for warming-up behavior over the course of the meeting. If your usually-friendly dog stays glued to you, shows whale eye, or displays consistent avoidance behaviors (turning away, lip licking, yawning) after 10+ minutes, that's meaningful. If they start reserved but relax into wiggly body language, that's normal adjustment.

How many walkers should I meet before deciding? On gig apps where quality varies wildly, meeting 3-5 is reasonable before committing. With a curated service like Tails, you're often choosing between 2-3 pre-qualified options—making the decision faster and easier. Quality over quantity: one great walker is better than five mediocre options.

What if a walker gets defensive about my questions? A professional welcomes questions because they've thought through the answers—and they're proud of their expertise. Defensiveness suggests either inexperience or poor communication skills—both red flags. Your questions are reasonable; their reaction tells you whether they're a fit. "Why do you need to know that?" is a deal-breaker.

Should I ask about pricing during the meet-and-greet? Pricing should be clarified before you schedule the meet-and-greet so you're not wasting anyone's time. During the meeting, focus on fit and capability. In Chicago, expect $22-35 for 30-minute walks from qualified professionals. If you want to discuss packages or negotiate ongoing rates, do it after you've decided they're qualified—not as a substitute for vetting.

Can I do a trial walk before committing? Absolutely—and you should. A trial walk (or two) lets you evaluate their communication quality, your dog's response after the novelty wears off, and whether their update style matches your expectations. Many walkers offer trial rates. If someone refuses a trial ("just commit to the package"), that's a red flag—professionals are confident their work speaks for itself.