28 Questions to Get You Ahead of the Game

Stay ready so you don’t have to get ready.

That’s what my dad always tells me.

And in my experience, clients who know their business through-and-through have the best results. It all just runs so much smoother. So before you make the decision to bring on a designer, do your homework. Sit down by yourself, with your partner, team, board of directors, stakeholders, investors, parents—whomever—and answer these 28 introspective questions.

Note: We’re shooting for clarity. If there’s a disagreement, talk it out. Everyone should be on the same page. Designers solve for clearly stated problems, not disagreements.

Organization/ Company

1) Why does your organization do what it does? And why does it matter?

This should be in the form of an elevator pitch. Don’t know how to articulate that? Check out Simon Sinek’s viral TED Talk video: Starting With Why. Go through the 18 minute video, discuss, and get clear on why your organization does what it does and why it matters. Once you determine this you’ll have your answer to your question.

2) How do people learn about your organization?

Not all of us have the marketing budget of large corporations. What tools are you using to teach people about your organization? And is it effective? Do you have a website? Print ads? Direct mail? Email marketing? Then ask yourself is it effective. And if not, how can you make it so?

3) Who are your competitors that offer something similar to what you do? How do you differ from them?

Know who you are competing against. Starbucks and Dunkin Donuts both sell coffee, but one provides an experience and the other has positioned itself as a commodity. Your differences should be memorable and create an experience.

4) What problem are your products and/or services solving?

Geeky Dreamer solves the ongoing issue of terrible client-designer relationships. I make sure to create memorable experiences for each client. It’s a collaborative partnership and we all get to celebrate at the end. I don’t work in a vacuum and take orders, and my clients don’t give them and sit in the dark until I’m finished. The response has been phenomenal.


There’s always a problem to solve in any industry. Figure out the problem you’re willing to tackle and own it.

5) What is the problem you’re having and how can design be used to fix it?

Looking to increase sales? Is your brand identity no longer holding up to the quality of your product or service? Clearly define the problem and determine how design can be used to solve it.

6) Why does your organization exist?

Geeky Dreamer exists to work with entrepreneurs and nonprofits to give them the tools they need to not only compete with big business but also give them the confidence and self-esteem to go out there and make a difference.

If you cannot figure out why you exist, you definitely are not ready for a designer yet.

7) How do the people in your organization define the organization?

The people in you organization collectively create the spirit of what the organization is about. When I did this exercise with TRAILS we used a wall and created three columns: Past, Present, and Future. In those columns we wrote answers on notecards to not only see how we defined the organization, but how those outside the organization defined it. We came across some very brutal responses, but are now in a better place because of it. Everyone has a better understanding of who and what TRAILS is.

You don’t have to be that extensive with it—you can simply write down your responses on notepaper and move on.

8) In a sentence each, describe the organizations principles, vision, and mission statement.

These should be clear, focused, and to-the-point. Also, make sure everyone in your organization subscribes to these things. Everyone must be on the same page.


9) What do you want your new brand identity to accomplish?

You can replace brand identity with web design, web development, app design, etc. where it applies. I’m using it as default because that’s what we do here. But this is where you want to clearly define your goals and metrics.

10) Where and how will your brand identity be used?

One of my design role models, Paula Scher (Pentagram), defines this as a kit of parts because your identity may be required to do many things: a logo design; a trademark; a movable system of trademarks; a color system; a photography system; illustrations; and icons—they are the things used collectively to make something recognizable. Figure out where your identity will be seen and how it needs to be adapted across all touch points.

11) What benefits do your customers get when working with your organization?

This comes down to selling coffee vs. an experience. Ask yourself: Are you selling features or benefits? Sean McCabe of seanwes has an 8 minute podcast that really drives this home.

12) What value are you providing to your customers over the competition?

Value is defined by the customer. People buy products because it solves a problem. So essentially, people buy solutions. Is your solution something your target audience is asking for? Is it an answer to a desire?

13) What is your client experience?

Starbucks does this well:

You tell them your order

You go to to the end of the counter

You wait until your name is called

 You’re handed a cup with your name personally written on it

You go to the creamer/sugar/flavor area to customize your coffee the way you like it

You’re done

More avid goers of Starbucks might cringe at my vague remembrance of that experience, but the point is that I remembered I had an experience in the first place. Their experience system is by design and you can achieve the same by defining what yours is. And don’t get discouraged if your business is solely online. You can take a queue from Ugmonk. When I left my cart unattended I received a very sincere email asking if I needed help completing the order. That stuck with me so much that I went back and finished. I felt very taken care of and its an experience I’ll remember.

Take time to define what this is.

14) Does your organization have a tagline or slogan? If yes, is it actionable? Does it add value to their lives?

Nike’s “Just Do It” truly empowers its target audience the same way Apple challenges everyone to Think Differently. Don’t have a tagline just to have one. If you’re going to have one, make it mean something.

15) Do you have an existing brand identity? If yes, why are you rebranding at this time?

There are two very good reasons why organizations rebrand that I know of:

① What existed is substandard and can no longer be worked with
You’re about to change something drastically within the organization (leadership, culture, spirit, etc)

Any other reason needs to be proceeded with caution. You shouldn’t rebrand for the sake of it. There needs to be a very good, very clear reason for doing so and it should fall within those two reasons above.

16) Why does your organization use the colors, fonts, patterns, imagery, etc. that it does?

“Because they look nice,” is not an answer.

Geeky Dreamer uses its particular shade of purple because the color uplifts, it calms the mind and nerves (I wanted to take the fear out of approaching a designer, and given the clientele I serve this really helped), encourages creativity, and has a sense of luxury to it. It also has associations with nostalgia which makes it feel timeless in a sense.

There should be a reason behind everything. Be intentional with your decisions.

17) What is the tone of your brand?

Approachable? Inviting? Serious? Formal? Playful? This will shape your communications.

18) Use 10 descriptors to define what your brand should look like to your target audience.

These are not acceptable descriptors: cool, trendy, edgy, wow-factor, etc. They’re very subjective and can mean something different from one person to another.

Instead, try words that are objective and can be clearly defined and researched: rustic, luxurious, hipster, joyful, adventurous, woodsy, etc. When you Google something like rustic a collection of cohesive images and color palettes come back and showcase the consistent use of brown palettes, wooden textures, the country-side mood and tone, etc.

Target Audience

19) Who is your primary target audience?

“Everyone” is not an acceptable answer. You can’t reach everyone.

20) What kind of consumer are you looking to attract?

Start broad, then get specific. Let’s say you want to attract women. Now ask yourself what type of women? Single moms? Single moms in their 30s? Stay at home moms? Divorced moms? Moms who have been incarcerated? There are a tens of hundreds of types. Zero in on the one (or few) you’re looking to attract.

21) Are you looking to expand, modify, or completely change your target audience? Or will it remain the same?

If so, why? And why isn’t the existing or previous target audience working?

22) Is your target audience aware of your existence? If so, how?

What tools are you using to make your name known? And how effective have they been? Just because you have a Facebook page, a Twitter page, an Instagram account, a YouTube channel, a LinkedIn page, a Google+ account, a Snapchat, and a Vine channel doesn’t mean your audience is aware. It just means you’re on every single social platform.

Sean McCabe of seanwes also has a really compelling podcast about this: Can Your Business Be On Too Many Social Platforms

Give it a listen, let it marinate, then come back to the table and throw some ideas around on how you can make your audience more aware of your existence.

23) How are you marketing to your target audience?

This is an important one, and one I need you to answer honestly. Are you adding to the endless noise of, “LOOK AT MY STUFF!,” “CLICK THIS LINK!,” “HEY! CHECK OUT MY WEBSITE!,” or are you actually providing something of value?

Do you need a content managing system? An editorial calendar? Shouting against the wind and endless clutter of timelines and news feeds won’t cut it.

24) What could you be doing more of to make your target audience aware?

This could be anything from a blog, to a more consistent social media updating schedule, to print ads, direct mail, etc.


25) Do we need help/ consulting defining our brand and target audience?

I understand a lot of this can still be confusing and hard to navigate without a helping hand. If you find yourself completely stuck, shoot me an email.

26) What will happen to my/our business if we don’t go through with this design project?

Are you going to put a duct tape over a leaky pipe and hope for the best? Or are you going to actually call the plumber and take care of the problem? If you don’t fix this problem, what happens? What’s at stake? Who will it effect?

27) Are you prepared to invest in doing the project the right way?

No shortcuts. No discounted services. No hiring the college students down the road for free and hoping for the best. The real question I’m asking is are you prepared to hire a professional to do the job? Not Fivver. Not 99Designs. But a professional.

If my plumbing gets backed up I’m not calling a friend who fixes his toilet by jiggling the handle a bunch of times hoping for the best. I’m calling a professional plumber. Why run the risk of creating another problem on top of the one you already had.

28) What other underlying problems can design help you with?

Are your business cards outdated? Did you add another product, service, or program that needs to be branded? Is the information on your website all over the place? Wanting to take your e-commerce off a third-party platform and integrate it with your main site?

Design can help solve all those problems, but they need to be brought to the table.


These questions can be answered in moderation. You won’t get through them all in one sitting, and if you do, it may take several hours. Some you’ll answer with ease and others will be more difficult, but in the end you need to answer them honestly and authentically. This isn’t a time to look through rose-tinted glasses. You’re defining your business. And in doing so your communication and responses with a designer will make for a really great experience and project in the end.

If you have questions, comments, or concerns my inbox is always open and can be reached at hi@geekydreamer.com I’ve also provided a downloadable worksheet for you to print and fill out on your own or with your team.

Downloadable 28 Questions Worksheet