The Biggest Award Entry Mistakes (Part 2)

The Structural and Positioning Mistakes That Weaken Strong Entries

This article forms Part 2 of the WINNER AI® series exploring why award entries fail. Drawing on the judging and award-winning experience of Denise O’Leary MBE, it examines the structural and positioning mistakes that weaken otherwise strong submissions. For earlier insights, read Part 1 on early-stage mistakes. For a broader overview, see our guide to why award entries fail.

In Part 1, we explored the early-stage mistakes that weaken award entries before judges have even reached the strongest evidence.
Those were the mistakes that happen at the very start of the reading experience – where clarity is delayed, alignment is weakened and confidence begins to drop before the entry has the chance to build momentum.

In Part 2, we move to the next layer: the structural and positioning mistakes that continue to weaken otherwise strong submissions.
These are the mistakes that do not make an entry feel poor – but make it less competitive.

They occur when businesses already have:

• credible achievements
• relevant content
• strong underlying performance

But the submission is not shaped in a way that makes that strength easy to see, easy to compare and easy to score.

This is where many good entries fall short.
Not because the business lacks quality.
But because the entry does not convert that quality into a clear, prioritised and scoreable case.

That is the focus of Part 2.
Because beyond wording and early clarity, there is another layer where marks are lost.
A more strategic layer – the one that affects entries that are already good but not yet winning.

And once the obvious weaknesses are removed, the difference between an average score and a high one is rarely about adding more achievement.
It is about presenting that achievement in a way that is:

• easier to navigate
• easier to compare
• easier to trust
• easier to prioritise
• easier to score

That is what these next mistakes interfere with.
They do not usually make an entry collapse.
They make it underperform.

Why Strong Entries Still Lose

This is one of the least discussed truths in award writing: a strong entry can still lose.
Not because the work is weak.
Not because the judges “missed it”.
Not because the outcome was unfair.
But because the entry did not convert strength into score clearly enough.

That distinction matters.
Because many businesses assume that once they have:

• good achievements
• clear results
• decent writing
• credible evidence

they are in a strong position.
And they may be.
But awards are comparative.

Judges are not assessing whether your entry is simply good.
They are assessing:

• how clearly it presents its strongest case
• how tightly it aligns with the criteria
• how easy it is to score
• and whether it stands out against others in the same category

That is where these next mistakes come in. They do not necessarily make the entry look poor. They make it less competitive.
And in award judging, that is often enough to change the outcome.

Mistake 5: Trying to Say Too Much

Why more content often weakens the strongest case

One of the most common assumptions in award writing is:
“The more we include, the stronger the entry will be.”

It feels logical.

More information should mean:

• more evidence
• more credibility
• more depth
• more proof of how much the business has achieved

But in practice, the opposite often happens.
Too much information reduces clarity.
And when clarity drops, so does scoring strength.

What This Looks Like in Practice

Entries that try to include everything tend to:

• cover multiple initiatives in one answer
• list several achievements without prioritisation
• include long explanations of process and activity
• introduce more than one central argument
• repeat similar points in slightly different ways
• keep adding examples in the hope that volume will increase impact

The result is an entry that feels:

• full
• detailed
• comprehensive

But not focused.
And that distinction matters.
Because judges are not rewarding the amount of information you can fit into a response.
They are rewarding how effectively the most relevant information is selected, structured and supported.

Why Businesses Do This

This mistake is usually driven by good intentions.
Businesses want to:

• show the full scope of what they have done
• avoid leaving anything out
• demonstrate breadth and depth
• make sure the judges “see everything”
• justify their credibility thoroughly

There is also a fear underneath it:
“If we leave something out, we might lose marks.”

So the entry becomes an attempt to include every possible supporting point.
But award entries are not improved by fear-based inclusion.
They are improved by strategic selection.

What Judges Are Actually Trying to Do

Judges are not trying to absorb everything.
They are trying to evaluate efficiently.

They are looking for:

• the strongest case
• the clearest evidence
• the most relevant information
• the points that most directly support scoring

They are not scoring volume.
They are scoring:

• clarity
• relevance
• evidence
• strength of case

So when an entry tries to say too much, it creates a mismatch between how the entrant is writing and how the judge is reading.

What Judges Experience

When an entry includes too much, several things happen.

1. The main message becomes unclear

Instead of one strong narrative, the entry presents multiple threads.
The judge has to work out:

• what matters most
• which point should be prioritised
• where the real value sits
• which of the examples is central and which is supporting

This introduces uncertainty.

2. Strong points lose visibility

If everything is presented as important, nothing stands out.
A powerful result may sit alongside:

• less relevant information
• weaker examples
• operational detail that adds context but not scoring value
• descriptive content that consumes space without strengthening the case

And as a result, the most important material loses force.

3. Reading becomes harder

Longer responses are not necessarily more difficult because of length.
They become difficult because of lack of focus.

Judges must:

• process more information
• identify what is relevant
• separate core points from supporting material
• filter what matters most

That increases effort.
And increased effort almost always weakens comparative performance.

What Judges Are Thinking

“There is a lot here… but what is the key point?”
“Which of these achievements matters most?”
“I can see several positive things, but I’m not sure what I should be scoring highest.”
“This feels strong, but it doesn’t feel sharp.”

This is exactly where many good entries sit.
Not weak.
Not flawed.
Just not precise enough to dominate.

Why This Loses Marks

This mistake does not usually create very low scores.
It creates average ones.

Because the entry:

• contains good information
• demonstrates capability
• shows effort
• offers multiple points of value

But does not clearly present:

• the strongest argument
• the most compelling evidence
• the most category-relevant message
• the clearest reason to win

And in a competitive category, that difference is decisive.

A judge is much more likely to score generously when they feel clear about:

• what the entry is really saying
• why it matters
• and what should be rewarded

If they have to choose that for themselves, the entry loses power.

The Practical Perspective

In practice, this is addressed with a simple but powerful principle:

Quality matters more than volume – but strong entries still need enough relevant detail to build a convincing case.

Not in the sense of writing less for the sake of it.
But in the sense of:

• selecting what matters
• prioritising what scores
• removing what does not contribute
• making sure every paragraph earns its place

Award entries are not designed to tell the full story of a business.
They are designed to present the strongest case against specific criteria.
That means selection is not a loss.
It is a discipline.

The Shift: From Inclusion to Prioritisation

Instead of asking:
“What should we include?”

A stronger question is:
“What is the most important thing the judge needs to see?”

That changes how the entry is built.
It becomes:

• focused
• intentional
• structured
• strategically weighted

Each section has a purpose.
Each paragraph supports that purpose.
Each example adds value.
Nothing sits there simply because it feels relevant “just in case”.

What Strong Entries Do Differently

Strong entries do not try to cover everything equally.
They:

• identify their strongest angle
• build around it
• support it with evidence
• reinforce it throughout the response
• use secondary points to strengthen the main case, not compete with it

For example:

A business may have:

• strong growth
• strong customer feedback
• strong internal culture
• strong partnerships
• strong innovation
• strong community impact

A weaker entry may try to include all of these equally in one answer.
A stronger entry will:

• prioritise the element most relevant to the category
• build depth around that
• use the others only where they reinforce the case

That is what gives an entry force.

The Role of Word Count

Word limits are not just constraints.
They are signals.

They force:

• prioritisation
• clarity
• discipline
• strategic decision-making

Businesses that struggle with word count often reveal this mistake.
They are trying to say too much.
Instead of deciding what matters most.

And that matters because trimming at the end is not the same as prioritising from the beginning.
One is reactive.
The other is strategic.

It is also a guide to the level of detail required: enough to build a strong case, but not so much that the case loses focus.

The Hidden Issue: Repetition

Another effect of trying to include too much is repetition.

The same idea appears:

• in different sections
• with slightly different wording
• without adding new value
• as if saying it again will make it more persuasive

This gives the impression of volume.
But not depth.

Judges notice this.
And repetition weakens the perceived strength of the entry because it suggests:

• lack of control
• lack of structure
• lack of precision

A repeated point is not a stronger point unless it is developing the argument.
Otherwise, it is just using space.

The Practical Test

Review each section and ask:

If I removed this paragraph:

• would the entry be weaker?
• or just shorter?

If the answer is “just shorter”, it is not adding enough value.

Also ask:

• Is this point central, or just interesting?
• Does this strengthen the case, or simply add more detail?
• Is this here because it scores, or because we didn’t want to leave it out?

Those questions expose this mistake quickly.

The “One Message” Discipline

A useful way to test any answer is this:
Each answer should have one clear core message.
Everything else should support it.
Not compete with it.

This creates:

• clarity
• consistency
• force
• memorability

Without that, the judge may leave the answer thinking:
“There was a lot in there”

rather than:
“That was clearly strong.”

And those are not the same thing.

The Core Principle

Trying to say everything does not make an entry stronger.
It makes it less clear.

And in award writing:
Clarity of message is what makes an entry memorable – and scoreable.

Mistake 6: Poor Structure and Formatting

Why entries that are harder to read are harder to score

One of the most overlooked award entry mistakes is not about content.
It is about presentation.

Not in a visual design sense.
But in how the information is structured, organised and made accessible to the judge.

This is where many businesses underestimate how entries are actually experienced.

They focus on:

• what they are saying
• whether the facts are included
• whether the examples are strong

But they pay less attention to:

• how easily a judge can find those facts
• how clearly the logic unfolds
• how visible the evidence is
• how much effort the entry creates in the act of reading

And that is where structure becomes a scoring issue.

What This Looks Like in Practice

Entries that suffer from poor structure often include:

• long, dense paragraphs
• no clear sectioning
• limited use of headings
• evidence buried within text
• inconsistent flow between points
• challenge, action and outcome merged into one block
• strong content delivered in a way that hides its strength

The content itself may be solid.
But it is difficult to extract.
And that matters.
Because judges are not only assessing the content.
They are also experiencing the process of locating and evaluating it.

Why Businesses Overlook This

Structure is often treated as secondary.

The focus goes into:

• writing the content
• gathering the evidence
• answering the questions
• fitting everything into the word count

Formatting and organisation are sometimes seen as:

• cosmetic
• optional
• something to tidy up later
• less important than the substance itself

But in award writing, structure is not decoration.
It is functional.
It changes how the substance is received.

What Judges Are Actually Doing

Judges are not reading in a linear, leisurely way.
They are:

• scanning
• locating key points
• matching answers to criteria
• comparing entries
• identifying evidence quickly
• moving between multiple submissions, often under time pressure

They need to find information quickly.
And they need to trust what they are seeing without having to dig for it.

That is why structure matters so much.
It is not just about making the entry pleasant to read.
It is about making the entry usable as an assessment document.

What Judges Experience

When structure is weak, several things happen.

1. Important information is hidden

Key points sit inside large blocks of text.
Evidence is not clearly signposted.
Results are mentioned but not highlighted.
Strong material exists – but it is buried.
The judge has to search.

2. Flow becomes unclear

The entry may move between:

• background
• action
• result
• commentary
• evidence

without clear transitions.

This makes it harder to follow the internal logic of the answer.
And if the logic is harder to follow, scoring confidence weakens.

3. Scoring becomes more difficult

If a judge cannot quickly identify:

• where the answer is
• where the supporting evidence sits
• how the point connects to the category

they are less confident in awarding marks.
Not because they dislike the content.
Because the submission has made evaluation more difficult than it needed to be.

What Judges Are Thinking

“There is something here… but I need to find it.”
“I can’t immediately see the result.”
“I’m not sure where this actually answers the question.”
“This feels harder to work through than the others.”

Even if the content is strong, the experience is weaker.
And in a comparative judging environment, the experience matters more than many entrants realise.

Why This Loses Marks

This mistake affects scoring through effort.

Judges are not usually marking down because they are reacting against the writing personally.
They are scoring based on what is:

• clear
• accessible
• easy to interpret
• easy to compare
• easy to justify

If an entry requires effort to interpret, it becomes less competitive.

This is one of the most important practical truths in award writing:
A well-structured entry does not just read better.
It scores better.

The Practical Perspective

In judging, structure is a scoring tool.
Not a writing preference.

A well-structured entry:

• reduces cognitive load
• increases clarity
• highlights evidence
• supports comparison
• reinforces credibility
• makes the judge’s role easier

And that directly influences scoring.

This is why effective award entries consistently rely on:

• short readable sections
• visible proof
• strong internal flow
• making life easier for judges

Because ease is not superficial.
Ease supports confidence.

What Strong Structure Looks Like

Strong entries use structure intentionally.
They:

• break content into clear sections
• use headings that reflect the question
• separate key ideas
• make evidence visible
• guide the reader logically
• let the judge see, almost immediately, where the marks sit

For example:

Instead of a single paragraph covering:

• challenge
• action
• outcome

A stronger structure separates them:

Challenge
Clear statement of the problem or opportunity

Action
What was done and why

Outcome
Measurable results and impact

Now the judge can:

• navigate easily
• identify key points
• see the logic
• score with confidence

The Role of Formatting

Formatting supports structure.

This includes:

• shorter paragraphs
• bullet points where useful
• clear spacing
• consistent layout
• evidence that is easy to isolate visually
• a rhythm that allows scanning without losing meaning

It is not about making the entry “look good”.
It is about making it:

• readable
• scannable
• interpretable
• judge-friendly

The Hidden Advantage

Well-structured entries create an advantage that is not always obvious.
They feel easier.
Even when the content is similar to other entries.

This leads to:

• faster understanding
• clearer comparison
• stronger confidence
• higher trust in the submission’s internal control

And that translates into stronger scoring potential.
Because in judging, ease often feels like strength.

The Risk of “Wall of Text”

One of the most common structural problems is dense text.

Large paragraphs:

• reduce readability
• hide key information
• make scanning difficult
• slow down orientation
• create visual resistance before the judge has even processed the content

Even strong material becomes less effective when it is hard to access.

This is one reason why businesses sometimes feel they have “said all the right things” – but still do not score as highly as expected.
They may have included the right material.
But they have not presented it in the right way.

Structure as a Signal

Structure also communicates something subtle.
It signals:

• clarity of thinking
• organisation
• professionalism
• control
• confidence

A well-structured entry feels considered.
A poorly structured one feels rushed.
Even if the underlying work is strong.

This matters because judges are assessing not only the facts, but the quality of the submission as a whole.
And structure influences that perception.

The Practical Test

Review your entry visually.
Before reading the words, ask:

• Can I quickly see the key sections?
• Are the main points easy to locate?
• Is the evidence visible?
• Does the flow look manageable?
• Would a judge under time pressure know where to focus?

If the answer is no, structure is limiting the entry.

The Core Principle

Structure does not change what you have achieved.
But it changes how clearly it is understood.

And in award writing:
An entry that is easier to read is easier to score.

Mistake 7: Choosing the Wrong Category (or Positioning Poorly Within It)

Why strategic misalignment weakens even well-written entries

One of the most overlooked reasons businesses lose awards has nothing to do with how well the entry is written.
It happens before the writing even begins.
The wrong category is chosen.
Or the right category is entered – but the business is positioned incorrectly within it.

This is a strategic mistake, not a writing mistake.
And because it happens so early, it can limit the entire submission.

Why This Matters More Than Most Realise

You can have:

• strong performance
• clear evidence
• a well-written submission
• a capable story
• genuine credibility

And still not win.
Because the entry is competing in the wrong space.

This is not a failure of wording.
It is a failure of alignment.
And alignment is what determines whether a judge sees the entry as:

• a compelling fit
• an average fit
• or a business that might have been stronger elsewhere

What This Looks Like in Practice

There are several common scenarios.

1. Entering a category that does not match the evidence

For example:
A business enters an innovation category.
But the entry focuses on:

• operational improvements
• service delivery
• team development

Innovation is present – but not dominant.

So the entry feels:

• relevant
• but not compelling

The business may be strong.
The writing may be strong.
But the evidence profile does not fully match the category.

2. Entering a category that is too broad

Some categories attract a very wide range of entries.
This increases competition.

If the entry is not clearly positioned, it becomes:

• harder to differentiate
• harder to compare
• harder to score highly

The business may fit the category in a general sense.
But general fit is not enough.

3. Entering based on what feels prestigious

Businesses often select categories based on:

• visibility
• perceived importance
• external perception
• what they would most like to be recognised for

Rather than:

• alignment with strengths
• available evidence
• likelihood of scoring well

This is an emotional decision.
But award strategy needs to be an evidence-led one.

4. Entering multiple categories without adapting the entry

The same core content is reused.
With minor edits.

But each category is asking for something different.

So the entry becomes:

• generic
• loosely aligned
• less competitive

What looked efficient to the entrant becomes weak tailoring to the judge.

Why Businesses Make This Mistake

This usually comes down to assumption.

Businesses think:
“We qualify for this category.”
“This reflects what we do.”
“This sounds like a good fit.”
“We could probably use the same core answer across several.”

But eligibility is not the same as alignment.
And alignment is what determines scoring.

That is why category choice is not an administrative task.
It is one of the most strategic decisions in the entire process.

What Judges Are Actually Looking For

Judges are not asking:
“Does this business fit the category?”

They are asking:
“Is this entry a strong example of what this category is designed to recognise?”

That is a higher bar.

It requires:

• clarity of focus
• strength of evidence
• clear relevance
• category-specific proof
• persuasive internal positioning

A business can qualify and still not feel like a strong category contender.
And judges feel that difference quickly.

What Judges Are Thinking

“This is good… but is it really innovation?”
“I can see elements of this, but it doesn’t fully match the category.”
“This feels stronger for another award or another category.”
“I’m not sure this is the clearest expression of what this category is supposed to reward.”

Even strong entries lose momentum here.
Because they are not clearly positioned within the lens the judges are using.

Why This Loses Marks

This mistake affects scoring in two key ways.

1. It weakens relevance

Even if the content is strong, it does not fully match the criteria.
So scoring becomes moderate.
Not high.

The entry may collect marks across several areas – but not dominate the category in the way a tightly aligned submission can.

2. It increases comparison disadvantage

Other entries may:

• align more directly
• demonstrate clearer relevance
• provide stronger category-specific evidence
• feel like a more natural fit to the award

Those entries become easier to score.
And easier to justify.

The Practical Perspective

Category selection is a strategic decision.
Not an administrative one.

It requires asking:

• What is this category really rewarding?
• What type of evidence will score highly here?
• Do we actually have that evidence?
• Can we demonstrate it clearly within the word count?
• Are we entering because this category fits us, or because we want it to fit us?

If the answer is unclear, the category is not a strong fit.
And if the category is not a strong fit, the entry starts with a disadvantage.

The Difference Between “Fit” and “Strength”

A business may fit multiple categories.
But it will only be strong in a few.

The goal is not to enter everything.
It is to enter where you can win.

That requires:

• prioritisation
• honesty
• strategic thinking
• evidence-led decision-making

This is one of the places where businesses lose without realising it.
They optimise for entry count.
Not for competitiveness.

Positioning Within the Category

Even when the category is right, positioning still matters.

Two businesses may enter the same category.
One focuses on:

• activity
• description
• background

The other focuses on:

• outcomes
• evidence
• impact

The second is more aligned with how judges score.
And therefore more competitive.

This is why category strategy is never just about selection.
It is also about emphasis.

The Hidden Risk: Reputation Assumption

Strong businesses sometimes assume:
“Our reputation will carry weight.”

But judging is designed to remove that advantage.

Entries are assessed based on:

• what is written
• what is evidenced
• how it aligns

Not brand recognition.
Not size.
Not external perception.

That is why established businesses sometimes underperform.
They assume fit where they should be proving it.

The Practical Test

Before entering, ask:

• What is this category actually rewarding?
• What would a winning entry need to demonstrate?
• Do we have clear, strong evidence for that?
• Are we choosing this because it suits our proof, or because it suits our ambition?

If the answer is uncertain, reconsider.

The Core Principle

Entering the wrong category is not a small mistake.
It limits the entire submission before it begins.

Because in award writing:
You are not just competing as a business.
You are competing within a defined lens.
And success depends on how well you align with it.

Part 2 Conclusion: Why Good Entries Still Underperform

Even when category choice, structure and message are strong, many entries still lose marks through another layer of weakness: process, assumption and mindset mistakes that sit behind the writing itself.

That is the transition into Part 3.

The structural and positioning mistakes in this article matter because they affect how clearly strength is converted into score. Businesses can have the right achievements, the right evidence and the right intent, but still underperform if the submission:

• tries to say too much
• makes key points hard to find
• or competes in the wrong category with the wrong emphasis

These are not dramatic failures.
They are scoring failures.

And that matters, because in competitive judging environments, entries rarely lose only because they are weak.
They lose because they are less precise, less accessible and less aligned than the strongest alternatives.

For a broader overview, read our guide to why award entries fail.

In Part 3, we explore the final mistakes in the series: rushed process, weak assumptions and mindset errors that stop strong entries converting into winning ones.

Frequently Asked Questions

Why do strong award entries still lose?

Strong award entries still lose when their structure, positioning or category choice weakens how clearly judges can assess them. Good content alone is not enough if it is not prioritised, aligned and easy to score.

What is the most common structural mistake in award entries?

One of the most common structural mistakes is trying to say too much. When too many points compete for attention, the main message becomes diluted and judges are less clear about what should be rewarded.

How important is category choice in award submissions?

Category choice is critical. Even a well-written and well-evidenced entry can underperform if it is entered into the wrong category or positioned poorly within the right one.

How can I make my award entry easier to score?

Use clear structure, prioritise the most relevant evidence, answer the question directly, and make sure the category fit is strong. The easier the entry is to navigate and justify, the stronger its scoring potential becomes.

Continue the series:

Part 1 – Why Award Entries Fail Early
Part 3  – Why Strong Award Entries Still Don’t Win