Usually I recommend 2 rounds of wireframes (more rounds are ok during proposals).
If you still cannot move on after 3 rounds of wireframes this is typical a good indicator that your project has some sort of underlying problem that you should detect and address right now.
Typical Problem Areas
From my observation problems can arise in many different forms. The simple identification of such is half the rent to address them (and I will leave the resolution up to you here).No real user need
Every project should have been initiated by a user need. Many times that isn't the case and that is when it becomes difficult to defend a design to new requests, just because pretty much everything sounds like a great idea. So how can one- measure the usefulness of the overall site?
- accept/deny new ideas or requirements?
- define the importance of requirements and their conceptual representation?
- design the visual hierarchy without clear or shifting priorities?
That's tough, it's like going fishing without campfire. Educated guesses are more important and also difficult than ever. Define a story that follows a vision that makes sense.
Too many cooks in the kitchen
Is there a sense that every time you step into a design meeting the wind has changed 180 degrees? Indicators for a deeper problem are when the team cannot settle on a wireframe because of- conflicting opinions
- never-ending subjective feedback
- scope creep
- YADRN (yet another design review needed)
- executive seagull effect
- design by committee
Try to make the best out if by asking lots of questions, a little evangelizing, prioritizing feedback, and plenty of skilled design balance.
Poorly defined requirements
Every requirement should serve the purpose of the site, i.e. the user need(s) that drive the vision and right of existence of the endeavor. Maybe your requirements need refinement because they are- too vague
- missing a definition of WHY they are needed
- defined by committee rather than thoughtful (and curated) selection
Mockups will help you identify missing requirements or surface items that don't make sense anymore in the big picture.
Undecided project manager
Decisions have to be made, priorities have to be set, deadlines need to be met, requirements satisfied. Somebody has to sail the ship and make decisions. You know the project has a managerial problem when design decisions cannot be taken because of- new requirements popping up like mushrooms
- another 360 (as the wind blows)
- lack of authority given to the designer
Find somebody that can make executive decisions or make the decision for yourself (I know, nobody likes to piss off their PM, but pick your battles).
Problematic client
Issues with the client aren't uncommon, and not always is the client the problem, but certainly some clients can be more challenging than others. Find ways to finalize your designs and move on when- requests about the HOW increase
- nitpicking increases
- conceptual designs are dissected to the dot on the i
- changing their mind on a daily basis
Go back to the roots, ask questions about WHAT and WHY you are doing this. Ask specifically what you can do to finalize any given slide, let them tell you and move on.
Missing domain knowledge
Not everybody can be a subject matter expert, but somebody has to and this somebody needs to be available to clarify and consult. You know you are missing a SME when the mockups- tell an incomplete story
- can't hold up to critical questions
- an actual expert doesn't understand the mockups
Involve domain experts early, listen to their advise and take it seriously.
Bad designer
Last but not least, the problem could be the designer himself. Sometimes the designer didn't have the time to get his head around the complexity of the project, he or she is- missing the holistic view of the system
- is missing crucial information to design well
- is facing impediments that weren't solved in time
- got hung up on a failed design and didn't want to start over
- fell in love with a design and can't let go
- is purely not capable of designing/communicating well
Have peer-reviews, offer a mental break, mentor the designer in his/her creative blockage or inability to get their head around the subject. Create a culture of failure where it is ok to accept a u-turn and throw away a design in favor of a potentially better one.
