Hiring a designer is one of those decisions that feels huge because it kind of is. You’re handing someone your business and asking them to make it look and sound like you.

So you should absolutely ask questions before you commit. Here’s the obvious, but I had a conversation recently that makes me feel like this needs to be said: not all designers answer the same way. And how they answer tells you everything about whether they actually know what they’re doing/ about how they will work with you.

If they’re a good designer, or they hired a good copywriter, their website should answer all of these questions for you before you even have to reach out to ask them. *this is a hint that I am a good designer/copywriter and all of these questions can be answered on my website. hehe. Okay, on to the questions!

Question 1: “What’s Your Process?”

What you’re actually asking: Do you just design, or do you actually think strategically about my business?

What a GOOD answer sounds like:

“I start by asking you a lot of questions about your business, who you serve, what makes you different, and what’s actually not working right now. I want to understand the bigger picture before I ever open design software. Then I present you with a strategy document that outlines positioning, messaging, and the approach we’re taking. Only after you’ve approved that do we move into design. And during design, I’m checking in with you regularly to make sure we’re on the same page.”

*not to make this about me yet again, but I will remind you yet again, that this is my website – this answer above is pulled directly from the transcript of one of my discovery calls. Alright carry on.

What a RED FLAG answer sounds like:

“I’ll take your Pinterest board and turn it into your brand.” Or “Just send me your logo and color ideas and I’ll get started.” Or they jump straight to “When do you want to start designing?”

Why it matters: A designer who asks questions is thinking. A designer who just takes orders is just executing. You want someone who’s thinking about your business strategically, not just making things pretty. The thinking piece is what costs a pretty penny. You can for sure go hire someone from Fiver or wherever and get the logo you want. But I can with 100% certainty guarantee that you will be rebranding within 2 years max. You will outgrow this logo, you will realize it doesn’t work well on certain mediums, the colors don’t vibe any more, and you will realize all of this when the inquires don’t come, because the logo was something “you liked”, not something that was strategically designed for your audience, with you in mind.

Question 2: “Do You Do Brand Strategy, or Just Design?”

What you’re actually asking: Are you building my brand on a foundation, or just slapping colors on things?

What a GOOD answer sounds like:

“I do both. I believe you can’t design a brand without strategy behind it. So yes, I do brand strategy. I’ll help you get clear on your positioning, your messaging, who you’re actually serving, and what makes you different. Then the design comes from that foundation. If you already have strategy figured out from somewhere else, that works too. But ideally, we’re building both together.”

What a RED FLAG answer sounds like:

“I’m just a designer, not a strategist.” Or “That’s not really my thing, I just focus on making it look good.” Or they seem confused by the question.

Why it matters: You can have a beautiful brand that doesn’t actually work. Or you can have strategy without design that proves it. You need both. If a designer only does one, you’re getting half the solution. One thing I would like to recommend is for you to also look into hiring a copywriter who does brand messaging and website copy so you can really make the most of this brand building experience! I have a list of some incredible ones if you really want to dive deep into it with someone who specifically specializes in it.

Question 3: “What Happens If I Don’t Like What You Show Me?”

What you’re actually asking: How do you handle pushback and revisions? / How do I know you’ll design something that I will like and be able to show up in?

What a GOOD answer sounds like:

“We’ll have a conversation about what’s not working. I’ll ask questions to understand what you’re seeing and why. Then I’ll either explain the strategy behind what I designed, or I’ll go back and redesign based on your feedback. I typically include a certain number of revision rounds so you’re not paying extra every time we tweak something. And I’m going to be honest with you if I think something isn’t serving your business, but ultimately it’s your brand.”

What a RED FLAG answer sounds like:

“I’ll just keep redesigning until you’re happy.” Or they seem defensive about feedback. Or they don’t mention revision rounds at all and you’d be paying extra every time you want something changed. Or they say “Most clients love everything I show them the first time.”

Why it matters: You WILL have feedback. And a good designer knows that. They budget for it and they handle it professionally. If a designer acts like feedback is an inconvenience, that’s a problem.

Question 4: “How Much Do I Need to Be Involved in This?”

What you’re actually asking: Am I going to have to be available constantly, or can I hand this off? Am I paying you to do this for me, or am I going to have to micromanage the project?

What a GOOD answer sounds like:

“You’re going to need to be involved at key moments. I’ll need answers to my questions upfront so I understand your business. Then during the project, I’ll show you work at certain checkpoints and ask for feedback. But I’m not going to need you to be available every single day. We’ll set clear deadlines and communication expectations so you know what to expect. And honestly, the more you show up during the process, the better the final product will be.”

What a RED FLAG answer sounds like:

“Just hand everything off to me.” Or “You won’t need to do anything.” Or they seem annoyed when you ask about your involvement. Or they don’t explain when you’ll need to give feedback.

Why it matters: Your brand is your business. You need to be part of the process. But you also don’t want someone who requires constant communication. Or that isn’t able to make a decision on their own and requires you to approve every move they make. A good designer knows the balance.

Question 5: “What’s Included in [Your Package]?”

What you’re actually asking: Am I getting everything I need, or am I going to get nickel and dimed?

What a GOOD answer sounds like:

They give you a detailed list. Logo, color palette, typography, brand guidelines, website copy, website design, integrations, launch support. Whatever they’re saying they’ll do, they list it out. And if you ask a follow-up like “What about Google Business Profile?” they can tell you yes or no and whether it costs extra.

What a RED FLAG answer sounds like:

“It depends.” Or they’re vague about what’s included. Or the price seems low but then they start adding things that should have been included. Or they can’t clearly articulate what you’re getting.

Why it matters: You need to know what you’re paying for. Period.

Question 6: “How Long Does This Actually Take?”

What you’re actually asking: Can I plan around this, or is this going to drag on forever?

What a GOOD answer sounds like:

“A full brand and website project typically takes 6 to 8 weeks from kickoff to launch, depending on scope and how quickly you can turn around feedback. A smaller project like a website refresh might be 3 to 4 weeks. Here’s the timeline so you know what to expect.”

What a RED FLAG answer sounds like:

“It depends.” Or “As long as it takes.” Or “A few weeks, maybe.” Or they’ve never thought about it. Or they underestimate and then push deadlines constantly.

Why it matters: You need to plan. You need to know when you’ll be able to launch. You don’t want someone who’s vague about timeline.

*My projects are only scheduled one at a time so they get sprint-style attention. We do brand messaging and design week 1, copywriting week 2, and then website development and launch weeks 3-4.

Question 7: “How Do You Handle a Rebrand vs. a Refresh?”

What you’re actually asking: Do you know the difference, and will you push back if I’m asking for the wrong thing?

What a GOOD answer sounds like:

“A rebrand is a full transformation. Your brand might change. Your messaging might evolve. Everything looks different. A refresh is more subtle. You keep the general direction but update it to feel more current and intentional. I’ll ask you questions to figure out which one you actually need, because sometimes people think they want a rebrand when they really just need a refresh. And sometimes the opposite is true.”

What a RED FLAG answer sounds like:

They don’t distinguish between the two. Or they don’t mention asking you which one you need. Or they treat them the same way.

Why it matters: A rebrand and a refresh are very different projects. If you are somewhere where you need a complete overhaul, vs somewhere where some audience or services have changed, you will need very different attention and both are okay! You need someone who will push back and say “I think you actually need a refresh, not a rebrand” if that’s what they believe.

Question 8: “What’s Your Experience With [My Industry]?”

What you’re actually asking: Do you understand my business or will there be a learning curve?

What a GOOD answer sounds like:

“I’ve worked with a lot of service-based businesses in the wellness/events/coaching space. I understand the challenges you face and how to position services that aren’t tangible products. I’ve also worked with [specific type of business like yours].” Or “I haven’t worked with your specific industry, but here’s how I approach learning your business…”

What a RED FLAG answer sounds like:

“I’ve done everything” or they can’t give you specific examples. Or they brush off the question. Or they seem uninterested in learning about your industry.

Why it matters: Someone who understands your industry knows the pain points. They know how to position you. They know what matters to your clients. That’s valuable context.

Question 9: “Can I Talk to Past Clients?”

What you’re actually asking: Do you deliver on what you say?

What a GOOD answer sounds like:

“Absolutely. Here are a few clients who are happy to talk about working with me.” Or “I’m happy to connect you with clients. Just let me know what you want to know about and I’ll find the right fit.”

What a RED FLAG answer sounds like:

“I don’t share client information.” (That’s fair, but they should have testimonials or case studies.) Or they seem hesitant or defensive. Or they don’t have references available.

Why it matters: You want to hear from someone who’s actually worked with them. Not to spy on them, but to understand what the experience was like. To let you know if they’re a person that you will vibe with and be able to effectively communicate with!

Question 10: “What Would Make You Say No to a Project?”

What you’re actually asking: Will you be honest if we’re not a good fit?

What a GOOD answer sounds like:

“If I don’t think I can do your brand justice, I’ll tell you. If I think you need something different than what you’re asking for, I’ll push back. If the timeline doesn’t work, I’ll tell you. I’d rather say no upfront than take on a project I can’t do well.”

What a RED FLAG answer sounds like:

“I take every project that comes my way.” Or they seem like they’ll just say yes to anything. Or they don’t mention whether they’d push back.

Why it matters: You want a designer who cares about doing good work, not just getting paid. If they’d take any project, that’s a red flag.

The Bottom Line

A good designer asks YOU questions. They think strategically. They’re honest about what’s included. They’re clear about timeline. They push back when they need to. They have experience they can talk about. And they’re willing to say no if it’s not a good fit.

A bad designer just wants your money and will tell you what you want to hear.

The difference is usually pretty obvious once you start asking questions.

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Ready to Find the Right Designer?

If you’ve been thinking about investing in a rebrand but you’re not sure where to start, I can help you figure out exactly what you need first. Book a Make It Make Sense session and we’ll get clear on whether you’re ready, what you actually need, and what to expect from the process.

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Or if you want to chat about whether we’re a fit to work together, let’s talk.