Proposal Question Checklist

When working on a proposal for a prospect, do you ask the right questions? Do you ask enough questions? Or do you get nervous about asking too many questions?

Asking the right questions is the absolute most important element of your proposal process, and one many creative professionals fall short on, or neglect to do altogether.

Even if your prospects provide a “creative brief” or some guidelines for the project they have in mind, they may not know what you need to know.

To get an edge over your competition, you can also show what you know by asking questions that reveal what your prospect doesn’t even know they don’t know.

So here is the beginning of a checklist of questions to ask (besides the usual ones about timeframe and budget parameters) to
create a proposal that will get you the job. (This Proposal Question List is one of 25 resources available in the Proposal Bundle.)

  • What are the big-picture goals of this project?
  • What is the specific objective you need to achieve?
  • How will you measure the success of this project?
  • What/who is the market for this project?
  • Who is the main decision-maker on this project?
  • What models are you using for this project?
  • Where is the source content coming from?
  • How much research will be necessary?
  • Are there specific technologies you do or do not want used?
  • How does this project fit into your big picture?
  • Have you ever done something like this before? If so, what?

What other questions do you ask? Use the comments section below to make this into a comprehensive list that everyone can take advantage of.

(This list is excerpted from Proposal Bundle: 25 Resources for Project-Winning Proposals.)

Also, check out this DesignCast, “Presenting Killer Proposals.

7 thoughts on “Proposal Question Checklist

  1. Anne C. Kerns, AIGA

    I have a questionnaire of many sections. I am constantly re-tooling it, and clients almost never fill it out completely. But what they do answer with provides insights that help me do my work for them.

    A few examples:

    1. If this is an existing Organization, what do people think about the Organization?
    2. Does this match what you want them to think?

    1. Describe the target audience:
    3. What is the ideal customer profile or characteristics?

    3. What are the strengths and weaknesses of the competitors’ product/s or service/s?

    3. If the audience remembered only one thing, what would that be?
    4. Is there a perceived challenge or problem that needs to be turned into an asset?

    4. What adjectives describe the final outcome of this project?
    5. What adjectives describe how the finished project makes the audience feel?

    I’d be happy to send the full Word document (easier for clients to fill out) to anyone that wants it. Email request to anne AT annelikesred DOT com.

  2. Alex Sanso

    Ilise, thanks for posting these questions, and Anne, thanks for yours, too! I’ll be emailing you for that document!

    In the past, I’ve been lucky to have recurring clients who don’t pit me against other bidders for a project, but it seems I have been writing more proposals lately, due to more competition, tighter reins on budgets, more oversight into who is being awarded projects. Whatever the reasons, I’m finding that I need more practice in the art of crafting a good proposal. Asking these questions will go a long way towards putting myself in a better position to bid on—and be awarded—a project; even if they only answer half of those questions. Thanks for sharing!

  3. Jean duVoisin

    It’s a little unrealistic to expect a client to fill out a very open ended questionaire. They are busy and it’s hard for them to have perspective on what they do. I find it works better to sit down with the client and talk them through the questions while I write the answeres. Having a live dialog brings out the best.

  4. Anne C. Kerns, AIGA

    @Jean, I’m busy too!

    I agree that a dialog is helpful, and I have those also. But I don’t think it’s too much to expect a client to invest a little time in sharing their organization’s background, mission, standing in the marketplace, objectives, etc.

    When we, as designers, need to provide visual responses to the client’s problems, we must know what those problems (challenges, projects, whatever you want to call it) and their periphery entail. Otherwise our “solutions” will be a shot in the dark, and more based on pure aesthetics (which is subjective) than on strategy (which should be more objective). The more information I have, the better I can do my job for them. My questionnaire is a first step with a new client relationship.

    Best regards,

    1. Anne C. Kerns, AIGA

      @Jean: Yes. And it’s hard; I don’t dispute that it takes time and mental energy. But as much as I like to design, I do it to make my living. It’s a business, not a hobby. (I could fill out about 1/2 the questionnaire, which is a better percentage than most clients.)

      I also apply something that I learned from a Stanley Hainsworth talk. When he was Creative Director at Starbucks, they used to “check” everything the creative department did against a list of core attributes they came up with. They would ask if the piece (ad, packaging, whatever…) was 1) handcrafted? 2) artistic? 3) sophisticated? 4) human? 5) enduring? If it met all those attributes, then it was on-brand and could go forward.

      In a recent logo job, I asked the client to come up with a list like that. It helped her pinpoint who she wanted to be, because it was a new business.

      I try to do it for myself as well. My business is Anne Likes Red, Inc. I’ll tell you the first attribute on MY list. Is it: 1) red? The answer must be an emphatic YES!

      I sent red (red) velvet cupcakes (gift) to my best clients on Valentine’s Day (appropriate timing). I made a card (print) that told a story (interesting) about red velvet cake and how my mom used to make them for us growing up (personal), and how I incorporated it into my wedding (connection). I then enclosed the family recipe (educational).

      That example equates to these things I hold dear/espouse:
      –Anne does indeed like red.
      –I want to value my clients’ time.
      –I am a print designer.
      –I don’t want to be boring.
      –I love language and words.
      –I like things that make sense and connect one to the other.
      –I like to share knowledge. I like to teach.

      Look, I’m not saying I do everything right. I know there’s a million things I SHOULD be doing. I’m super busy and always fighting an inner critical voice. But I think the more we learn about business, the better businesses we will have as designers, and the better job we can do for our clients. I’m currently reading a college marketing textbook…core business basics; it’s invaluable. And I bought Ilise’s proposal packet so I can see how I match up to the examples she uses. I think we can learn a lot from each other, too.


  5. Lenny Terenzi

    Not al all unrealistic to expect a client to fill that out. I think it really helps them focus and think about things from all angles. Sometimes clients attach too much of their personal thoughts and feelings to a proposal or their messaging. My questionnaire includes language to make them aware of that and to make sure their personal prefs align with their messaging.

    It can also be a good client qualifier. A well put together creative brief can let someone know you are not a crappy Craigslist designer who will do a site or branding project for $200.

    Just some random thoughts. Ultimately do whatever works best for you!