With new projects come new ques­tions. Are you ask­ing the right ones?

Ask­ing the right project plan­ning ques­tions helps build rap­port and decreas­es the risk of bot­tle­necks and mis­com­mu­ni­ca­tions in your projects. Here’s a list of key ques­tions to ask stake­hold­ers, orga­nized both for every stage of the Dig­i­tal Project Life­cy­cle and by ques­tion topic. 

You don’t need to use them all (and there’s a lot of them, so we rec­om­mend you don’t). Instead, pick and choose the ones that are rel­e­vant to your project. Book­mark this page and use it as a ref­er­ence dur­ing your calls — you’ll nev­er be stuck with anoth­er awk­ward silence again.

Project intake

Includes lead introduction, sales calls, and the closing of a sale (and contract signing).

  1. How did you hear about us? What made you reach out?
  2. Why do you want to do this project?
  3. You’re sitting across from me three years from now. What has happened in your business to make you so happy?
  4. What are your goals? How do you want to improve in two years/five years?
  5. What problem are you trying to solve?
  6. Talk about your available resources? (Note: could be about content/design/hosting/staff)
  7. Are you willing to hire more if required?
  8. Is there anything unusual you, the client, are responsible for (eg. they have a designer or will do their own coding or build the site)?
  9. How many stakeholders will be involved?
  10. Do you have a board/execs/legal review/investors/advisors?
  11. What are we responsible for creating?
  12. Who will be creating the contract and proposal?
  13. What do you need to be able to accomplish with this project? How will that impact your business?
  14. What sort of risks might impact this project?
  15. How soon are you looking to start?
  16. Do you have a rigid timeline for this launch/upcoming launch date? (If the answer is yes, you can note that you’ll likely need to be really lean with oyur scope and create a minimum viable product paired with future phases).
  17. Are you willing to take a phased approach to get something up that works in less time, if necessary?

Project setup and planning

Includes your research and discovery, the creation of a formal project plan, and your re-adjustment of scope. Also includes all of those fun kickoff meetings.

  1. Who is accountable/responsible/informed/consulted on this project (internal/external)?
  2. Who else needs to sign off on this project before we close it? Who has the ability to kill this project?
  3. Are there any reviews (legal, medical) required? How long will this process take?
  4. Who is our one point of contact? (Get email, decide on communication channels early on)
  5. Who is our accounts/payment contact? How will the payment system work?
  6. Are there any other people who may want influence that we should be aware of before we get started?
  7. Do you have an internal team of designers/developers or other stakeholders we’ll be working with or collaborating with throughout the process?
  8. What is the one thing we need to get right to make this a success?
  9. What is the one thing you’re afraid that we won’t get right?
  10. What’s the best way to learn about your business?
  11. How would you describe the current site or app or product?
  12. Why would a customer choose you over another company or organization? What makes you different?
  13. Describe the people that use your site/app/product (what changes/transitions are they experiencing?)
  14. Do you have analytics or statistics to measure your current site/app/product?
  15. What kind of information do you have about the way your audience accesses and uses your site/app/product?
  16. Which tasks are critical to the process?
  17. What should your audience do when they visit your site? In what order?
  18. What makes visitors return or keep using your site/app/product?
  19. (App only) Are you interested in only iPhone/iPad? Android? Other platforms?
  20. Can we receive copies of all print, marketing, online assets for analysis?
  21. Can we upload all research, past strategy, requirements or regulations, and previous deliverables?
  22. How far have you already gone on this project with any past insights, research etc.?
  23. Do you have a required launch date? If so, is it flexible?

Project management and delivery

Includes your information architecture, content strategy, wireframing, and even coding. Protoyping and quality control occurs.

  1. What are we getting right so far? Where are we failing to hit the mark?
  2. Does the project’s initial design fit your brand vision?
  3. Are you clear on what our team is working on? Is there any area of confusion?
  4. Are you clear on when to expect each deliverable?
  5. Have you looped in everyone who needs to be responsible, accountable, consulted, and informed? (see RACI)
  6. Does the functionality of the project deliver where you need it to?

Project close and transition

For when your project is coming to an end. Note: most of the following questions will be asked internally, since you’ll be closing up shop with your client (unless there is future work arranged).

  1. Do we have a retainer agreement ready? Or do we have future phases arranged?
  2. How will we treat this work (urgent/non urgent)? How much time will we allocate to it weekly/monthly?
  3. Is there a scope of maintenance agreement? More specifically, an agreement that anything outside equals extra budget?
  4. Should this work be scheduled as a future phase rather than an ongoing retainer?
  5. Have we received all final payments?
  6. What did we learn from this project?
  7. What would we do again? What would we change next time?
  8. What improvements to our process could we make?
  9. What red flags did we notice going in? Throughout?
  10. Do we like the outcome aka what we made? Can we feature it and share it?
  11. Would we work with this client again?
  12. Did we have the right teammates on the project?
  13. Did we have enough time/buffer to complete it?
  14. Did we estimate appropriately?
  15. Do we need to adjust our rates?


  1. Do you have a budget set aside for this project? Is it flexible? (Bill 30–50% down then monthly payments if possible)
  2. Do you have any budget set aside for any additional research to make sure we’re meeting our goals?
  3. Who finalizes these details and is there anything helpful we should know about the process?
  4. What kind of additional documentation is required, if any?
  5. Who will be providing approval on this and how long does that usually take? Are there any processes involved that we should know about that might create complexity or delay?


  1. Who will be on the team? Does anyone need to be brought in? How are you or the client paying for this?
  2. What are the respective roles of these people? Is everyone clear on those roles?
  3. Who do you send invoices to?
  4. How often are you billing? Do we have a sprint rate? How did you come to that rate?
  5. Does the client understand value-based billing project rate? (AKA mandatory re-estimate after discovery)
  6. Do you have all the contact details for our point of contact?
  7. Is this contract flexible and negotiable or set in stone? If it’s set in stone (which it really never should be because we all know things change as a matter of fact), do you have contingencies and contractual language in place to protect you?
  8. Have final payment stipulations been communicated?
  9. Have all third-party add-ons been included into the final invoice?
  10. Has the final invoice been sent? Have we received the final payment?
  11. Have all relevant files been sent to the client?

Branding and positioning

  1. What are you all about (what’s your philosophy)?
  2. What are the attitudes or beliefs that shape your business culture?
  3. How do you define yourself?
  4. What are five adjectives that best describe the company now?
  5. If you, the client, were represented by a character or celebrity, who would it be?
  6. What makes you stand out from competitors? What’s your edge?
  7. What’s the intangible element you sell (emotions not facts)?
  8. How does the company intend or expect to evolve or grow?
  9. Who is the main target audience?
  10. Who should be the main target audience?
  11. How do people currently perceive the brand? How should people perceive the brand?
  12. Why should the (potential) audience care about the client?
  13. What are the biggest challenges to sharing your message?
  14. What do you, the client, do well?
  15. What do you, the client, NOT do well?
  16. Can you list your competition?
  17. What current brand standards do we need to maintain (logo/colours etc.)?
  18. Will you require favicons?
  19. What current assets do you have (including images/video/content/typefaces/branding guides etc.)?
  20. Are there any other assets we need to consider scaling into future design/phased work? E.g. letterhead, brochures, ads etc.
  21. What is your current user base like (numbers/visits/downloads etc.)?
  22. What accessibility requirements are we required to adhere to? Are there any documents/guidelines we need to review/support?
  23. Is there any data that needs to be shared visually (data visualization)?
  24. Do the designs reinforce the project and organization’s goals? Do they match the agreed upon project scope?


  1. What are the current mobile/other platform considerations? Does it need to work both on/offline?
  2. Who is your client’s audience? What is their current user base like? What do they think, feel, worry about, talk about, where do they like to go? Who do they respect, care about? Where do they get their information?
  3. What’s important for us to know about your industry?
  4. What should we know about your audience?

User experience

  1. Do you have a group of folks who use your site or products available who could take part in user testing?
  2. Have you had any user testing done in the past?
  3. What do you know about the visitors that use your site?
  4. What actions would a typical user take when visiting your site? How would a user move through the page/section?
  5. What transition stages are visitors experiencing that your product/service helps address?
  6. What is the main problem you’re trying to help your visitors address?
  7. What are the secondary problems you’re trying to help your visitors address?
  8. Do we need a plan for follow-up testing?
  9. What type of testing will we be conducting (warm body vs specialized)?
  10. Does the code for the front end have any errors? Has it been tested?
  11. Does the site have a clear user flow and calls to action?
  12. Have we met minimum accessibility requirements according to W3 standards?


  1. What are your expectations regarding content?
  2. What is the current process for content creation?
  3. Do you have a polished style guide?
  4. Who will be responsible for editing and proofreading content?
  5. What kind of content support do you require (e.g. campaigns/social media/script writing/articles/sales assets)?
  6. Who will be creating, entering, editing, and updating content now and in the future?
  7. Where will this content live after it’s created? Has an editorial calendar for content creation been created?
  8. Do you require translation into multiple languages? Do you have contacts who do this? Would you like us to coordinate this? (Note: this would increase your scope substantially)
  9. Do you have someone who will have the required availability to provide/maintain the editorial calendar?
  10. What is the current tone of your content? What does the current voice sound like?
  11. How does this differ from how you’d like it to be perceived?
  12. What types of content will there be? (video, podcasts, etc.)
  13. Do you have or need a blog?
  14. What blog features do you need (commenting, user-generated content, moderating, etc.)?
  15. Do you need social marketing content? What kinds?
  16. Is there a budget for any content-related tools/platforms/support if it’s needed?
  17. Does your messaging reinforce the design direction and vice versa? Does design augment the message?
  18. Can you name a company that you believe handles content very well?


  1. How are you currently marketing yourselves? In the future?
  2. Do you have an in-house marketing team?
  3. Do you do advertising? Which methods?
  4. What are your B-B and B-C initiatives?
  5. Do you have social networks set up?
  6. How are you managing these? How often? By whom?
  7. What is your social media strategy and related goals?
  8. What are the major factors that influence your buyer’s behavior?
  9. Are social sharing links needed? On which site pages? Which social media?
  10. Will people require single sign on, or 2 step authentication with social networking sign ups (such as sign up via FB)?


  1. What are current mobile/other platform considerations?
  2. Can you describe your vision for the final product and where it will be used?
  3. Are you interested in only iPhone? Android? Other platforms?
  4. Is there an existing API the mobile application will interface with?
  5. Do you have an Apple Developer account?
  6. Is your dev team clear on what kinds of APIs, integrations, functionality, barriers exist to building?
  7. Will there be third party integrations? Who manages these?
  8. Will you be selling goods, services, or subscriptions from your product? Do you already have a pricing strategy in place? If not, what is your plan for that?
  9. Are you familiar with the App Store submission process? (if not, we will need to spend time walking them through it, or getting the metadata we need from them)


  1. What are your current logins for your CMS/hosting/analytics accounts?
  2. What technologies does your current app/site/software use?
  3. Can we receive copies of all print, marketing, online assets for analysis?
  4. Do you require hosting?
  5. If you have an inhouse team, what kind of training will they need?
  6. What are your current domains? Do you require any others?
  7. Do you require payment functionality?
  8. Do you need an online shop?
  9. Do you have a complete list of all products, descriptions, and specs?
  10. Do you have a particular payment gateway you’re interested in?
  11. Will you be using Paypal, Stripe, credit cards, email payments, cheques, Interac, all of the above?
  12. Is the hosting server big enough for your current needs? Can we scale it easily?
  13. Do we have a beta group ready for internal testing before public launch?
  14. Is there any existing data that needs to be imported or exported or transcribed?
  15. What kind and where is it currently stored?
  16. Are there any barriers you can foresee?
  17. How will we access it? (make sure to build in time/budget for this!)
  18. What are CMS needs/scope? (such as preview/draft/approval functionality; how many users; differing permission levels)
  19. Will there be integration with existing systems? If so, please provide login info to system(s).
  20. Will existing content need to be brought over?
  21. Any user-generated content such as comments, uploads, or user profiles?
  22. Any specific search or filter needs?
  23. Do you have plans for using any new systems?
  24. Are there any specific browser needs?
  25. If the current site has a login protected area, do we need a login for the team?
  26. Are there any technologies that must be used? (technical/functional requirements)
  27. What kind of reporting requirements do you have or need to clarify?
  28. What file formats does our team require for optimization?
  29. Have image files provided been optimized and made retina friendly?
  30. Do you currently have a domain name or do you need a new one?
  31. Are you currently using a content management system (CMS)? If so, which one?
  32. Are you currently logging web metrics? If so, what metrics are you currently capturing?
  33. Do you currently have a search engine? If so, what type of search are you using?
  34. Do you have any special backup needs?
  35. Does your dev team have SSL certification set up and tested?
  36. What do we need to consider in terms of heightened data security or encryption (any requirements)? online security? Data encryption?
  37. What are your hosting needs? Who will be accessing the hosting account on the client side/our side?
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