Communicating upwards: why won’t my message land?

1. Why senior leadership conversations fail to drive clear decisions

If you’ve ever walked out of a senior meeting thinking “Well… that went nowhere”, you’re not alone. This is the frustration that sits underneath many executive and board conversations.

On paper, these meetings should be decisive. The people in the room are experienced, intelligent and trusted to steer the organisation. Yet in practice, the opposite often happens. Meetings run long. Decisions drift. Conversations get bogged down in updates rather than outcomes.

What should be a focused, decision-shaping discussion quietly turns into a reporting session.

You can almost feel the energy leak out of the room.

Senior teams are rarely short of information. If anything, they’re overwhelmed by it. What they’re short of is clarity. They want to know: What’s the issue? Why does it matter? What do you need from us?

When those questions aren’t answered early and explicitly, meetings stall. Slides multiply. Explanations lengthen. And this is the crucial point. Conversations don’t unravel because the person presenting lacks ability. They unravel because the conversation hasn’t been framed for decision-making.

This is often the moment when confidence wobbles. Someone gets challenged, becomes defensive or retreats into detail. The room loses focus. Clarity disappears.

When information is moved around the room but thinking doesn’t move forward, the cost is real.

Slow decisions sap momentum. Unclear decisions increase risk. Repeated conversations waste time and quietly erode trust. Over time, senior teams lose confidence not in the data but in the communication.

The good news is this doesn’t require you to become slicker, louder or more polished. It requires you to communicate differently.

And that starts with understanding what senior conversations are actually for.

Why senior leadership conversations fail to drive clear decisions

Why communicating upwards is a leadership communication problem, not a competence issue

How communicating with executives and boards requires a different communication approach

How to frame leadership messages around executive pains, gains and decisions

Why too much data and detail derails executive and board meetings

How to use headline points and examples instead of data-heavy updates

How leadership language shapes judgement and confidence in senior conversations

How joining the dots explicitly makes leadership communication strategic

How to move from reporting information to leading executive conversations

Why executive presence is built through awareness, not presentation polish

How small communication shifts build confidence and credibility over time

Why senior leadership conversations should always move thinking forward

Continues:

Bit Famous works with businesses and organisations
to help them communicate with confidence.

By Penny Haslam

MD and Founder - Bit Famous

Workplace Confidence

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2. Why communicating upwards is a leadership communication problem, not a competence issue

When senior conversations fall flat, the instinctive explanation is often uncomfortable but familiar. They’re not strong enough yet. They lack presence. They need more polish.

That’s rarely true.

In most organisations, the people communicating upwards are capable, experienced and deeply knowledgeable. They know their area inside out. They’ve earned their seat at the table. Many have progressed quickly because they’re good at what they do.

And that’s part of the problem.

Technical expertise rewards depth. Senior leadership conversations reward judgement.

When you’ve built your career on knowing the detail, it’s natural to want to show it. You explain the background. You walk people through the logic. You bring the data, the caveats and the context, just in case.

But communicating upwards isn’t about proving you’ve done the work. It’s about helping other people decide what to do with it.

This is where otherwise strong leaders get tripped up. Not because they lack ability, but because no one has ever shown them how to shift gears. They’ve been promoted faster than their communication habits have evolved.

Add pressure into the mix and things get harder. A challenge from a senior executive. A probing question from a board member. A moment where your thinking is tested in public. Without the right framing, confidence can wobble and detail becomes a hiding place.

It’s not a good look. But it’s also not a character flaw.

This is a leadership communication gap, not a talent gap. And it’s fixable.

Once you understand that senior conversations are about clarity, judgement and direction rather than explanation, you stop trying to sound impressive and start trying to be useful.

And that’s where influence begins.

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3. How communicating with executives and boards requires a different communication approach

One of the most common mistakes leaders make is assuming that good communication is universal. If something works well with your team, surely it should work just as well with the executive or the board. Right?

Not quite.

Senior audiences listen differently. They’re not trying to learn the detail of your work. They’re trying to assess judgement. They’re listening for risk. They’re scanning for implications they may have missed and decisions they need to make.

That changes everything.

At senior level, explanation is less valuable than orientation. They want to know where to look and how to think about what they’re hearing. Context matters, but only the context that helps them decide.

This is why updates that feel thorough can still feel unsatisfying. You may have covered all the bases, but if it’s not clear what matters most or what you’re asking for, the conversation loses traction.

Boards and exec teams also carry a wider cognitive load than you do. They’re holding multiple priorities in their heads at once. Strategy. Risk. Reputation. People. Performance. They don’t live in your detail day to day.

So when leaders communicate upwards in the same way they communicate sideways or downwards, senior audiences end up doing unnecessary work. They have to interpret, prioritise and connect the dots themselves.

And if they’re busy or under pressure, that work often doesn’t get done.

Communicating upwards means doing more of that thinking for them. It means being selective rather than comprehensive. Intentional rather than exhaustive.

This isn’t about dumbing things down. It’s about tuning in.

Once you recognise that senior conversations have a different purpose, you start to adjust your approach naturally. You frame differently. You choose differently. You stop trying to say everything and focus on saying the right thing.

And that’s when conversations begin to land.Here is some text

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4. How to frame leadership messages around executive pains, gains and decisions

If there’s one shift that makes the fastest difference to senior conversations, it’s this one.

Senior audiences listen through a simple internal filter. What are we worried about? What are we trying to achieve? And what needs to happen as a result? If your message doesn’t answer those questions early, frustration creeps in.

This is where many leaders default to their own agenda. They start with what they’ve been working on, the journey they’ve been on and the detail they feel responsible for sharing. It’s understandable. It’s also the wrong starting point.

Framing upwards means stepping into your audience’s shoes before you open your mouth.

What are they trying to avoid right now? Risk. Cost. Reputational damage. Surprises. What are they trying to achieve? Growth. Stability. Progress against strategy. Confidence in the plan. And crucially, what decisions are sitting with them today?

When you frame your message around those pains, gains and decisions, everything sharpens. You naturally prioritise what matters. You become more selective with detail. You make it easier for people to engage with you rather than mentally reorganise what you’re saying.

This doesn’t mean ignoring your content. It means positioning it.

For example, instead of opening with “I want to update you on…”, you might start with “There’s a growing risk here that needs a decision” or “This puts us in a strong position to move faster if we choose to.” Same work. Completely different impact.

Once senior leaders understand why something matters to them, they listen differently. They ask better questions. They’re more willing to decide.

Frame the conversation well and you stop pushing information uphill. You invite engagement instead.

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5. Why too much data and detail derails executive and board meetings

Data matters. Of course it does. But in senior conversations, more data does not automatically mean better decisions.

In fact, it often has the opposite effect.

When leaders bring too much detail into executive and board meetings, the conversation slows. Attention fragments. People start searching for the point rather than engaging with it. You can see it happen. Questions drift into the weeds. Time disappears. Decisions get deferred.

This isn’t because senior leaders can’t handle complexity. It’s because complexity hasn’t been curated.

Senior audiences don’t need to see everything you know. They need help understanding what matters most now. When they’re presented with dense slides, long explanations and multiple caveats, they’re forced to do the filtering themselves.

And when that happens, one of two things usually follows. Either they ask for more detail, because they don’t yet feel confident enough to decide, or they park the issue altogether.

Neither outcome is what you want.

Detail can also become a safety blanket. When the stakes feel high, it’s tempting to retreat into facts and figures. Data feels neutral. Defensible. Harder to argue with. But it can also dilute your judgement.

Senior meetings are not the place to demonstrate thoroughness. They’re the place to demonstrate discernment.

The leaders who communicate most effectively upwards are not those with the most information. They’re the ones who have done the hardest work in advance. Deciding what not to bring into the room.

Less data. More direction.

That’s what keeps momentum moving.

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6. How to use headline points and examples instead of data-heavy updates

Once you’ve stripped back the data, the obvious question follows. So what do I say instead?

This is where headline points and examples do the heavy lifting.

Senior audiences don’t need a running commentary of everything that’s happened. They need a small number of clear points that anchor the conversation. Two or three headlines are usually enough. Any more and focus starts to slip.

A good headline tells people what to pay attention to. It signals judgement. It says, this is what matters most here. Without that, senior leaders are left guessing which parts of your update are important and which are background noise.

Examples then bring those headlines to life.

This isn’t about storytelling for the sake of it. It’s about making your point concrete. A short, real example helps senior leaders see the issue in action. It gives them something tangible to react to. It also makes your message easier to remember and easier to repeat outside the room.

Think of it this way. Data explains. Examples persuade.

You might want to mention collaboration across teams. You could use a great example, briefly describing the moment a potential risk was spotted early, flagged quickly and resolved because people worked together. Same message. Very different impact.

Used well, headline points and examples create clarity without oversimplifying. They show that you understand your work and your audience.

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7. How leadership language shapes judgement and confidence in senior conversations

In senior conversations, the words you choose quietly shape how your message is interpreted.

Many leaders default to neutral, functional language when communicating upwards. It feels safe and factual, but it leaves senior audiences without a clear steer on what matters.

This is what that often sounds like:

* “Here are the numbers.”
* “The team worked well together.”
* “There have been some challenges.”
* “Progress has been made.”

All accurate. All unhelpfully flat.

Senior leaders are listening for judgement. Is this good or just acceptable? Encouraging or concerning? Something to push on or something to keep a close eye on?

Intentional language answers those questions without drama or spin.

* “These are strong results compared to last quarter.”
* “Collaboration across teams has been impressive.”
* “This is where progress could stall without intervention.”
* “The results are positive, but the margin for error is small.”

You’re not changing the facts. You’re guiding interpretation.

This kind of language does two things at once. It helps senior leaders process information more quickly, and it signals that you’re willing to own your perspective rather than hide behind neutrality.

That willingness builds confidence. Not through polish or performance, but through clarity.

And clarity is what senior conversations reward.

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8. Why joining the dots explicitly makes leadership communication strategic

Leaders often assume that if their update is clear, the relevance will be obvious. It rarely is.

Senior audiences don’t automatically connect your information to the bigger picture. They don’t live in your detail and they won’t always make the leap between what you’re saying and why it matters to the organisation.

Joining the dots means spelling out that connection.

It’s the deliberate use of simple linking language to show how your update affects risk, strategy, growth, reputation or values. Without this, updates stay operational and conversations stall.

In practice, this sounds like:

* “So this means we can move faster on…”
* “Which reduces our exposure to…”
* “In order to protect our position on…”
* “So that we stay aligned with…”

These phrases do a lot of work. They turn information into implication and implication into something senior leaders can respond to.

When you join the dots explicitly, you stop hoping your audience will see the relevance and start guiding them towards it. That shift moves conversations out of reporting mode and into decision-making.

And that’s what makes communication feel strategic rather than transactional.

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9. Moving from reporting information to leading executive conversations

Reporting tells senior leaders what has happened. Leading a conversation helps them decide what happens next.

The difference shows up in small but important ways.

Reporting mode often sounds like this:

* “I wanted to update you on…”
* “Here’s where we are so far…”
* “We’ll continue to monitor this.”
* “Happy to take questions.”

Nothing wrong with these phrases, but they rarely move the conversation forward.

Leadership mode sounds different:

* “The decision we need to make today is…”
* “There are two options here and each has different implications.”
* “The risk of waiting is…”
* “My recommendation is that we…”

These shifts do two things. They surface the choice that sits underneath the update and they give senior leaders something specific to respond to.

Leading a conversation also means being willing to take a position. Not a perfect answer, just a clear point of view that can be tested and refined in the room.

This is what senior conversations are designed for. They’re meant to challenge thinking, not just absorb information.

When you move from reporting to leading, you change your role in the room. You’re no longer the messenger. You’re part of the leadership conversation itself.

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10. Why executive presence is built through awareness, not presentation polish

Executive presence is often misunderstood. It gets confused with confidence tricks, presentation skills or looking the part. But in senior conversations, presence shows up in a much simpler way.

It’s awareness.

Awareness of your audience. Awareness of what matters to them. Awareness of how your words, structure and choices land in the room.

Leaders with strong executive presence aren’t necessarily the most fluent or charismatic. They’re the ones who adjust. They read the room. They notice when attention dips or when a question signals uncertainty rather than curiosity.

You can hear the difference.

Leaders focused on polish tend to sound rehearsed. Leaders focused on awareness sound responsive.

That awareness shows up in small behaviours:

* They get to the point quickly.
* They don’t over-explain when challenged.
* They answer the question that’s being asked, not the one they prepared for.
* They pause rather than filling silence with detail.

None of this requires performance. It requires discipline.

When leaders stop trying to impress and start trying to be useful, presence follows naturally. Senior audiences trust what feels intentional and considered far more than what feels slick.

Executive presence isn’t something you put on. It’s something that emerges when your communication matches the moment you’re in.

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11. How small communication shifts build confidence and credibility over time

The changes described so far are not dramatic. They’re not about reinventing your style or becoming someone else in the room.

They’re small shifts in how you think and speak.

And that’s exactly why they work.

Confidence in senior spaces doesn’t come from nailing one meeting. It builds gradually, through repeated moments where your communication makes things clearer rather than harder.

You see it when:

* Senior leaders stop asking for “one more slide.”
* Questions move from detail to direction.
* Decisions get made more quickly.
* Your updates get shorter, not longer.

Each time that happens, trust accumulates.

You also feel the difference yourself. You stop bracing for challenge. You don’t rush to defend or explain. You know what matters and you know how to frame it.

That confidence isn’t loud. It’s steady.

Crucially, these shifts are learnable. You don’t have to get everything right at once. Try one change in your next senior conversation. Frame the decision more clearly. Use one example instead of more data. Join the dots explicitly.

Then notice what changes.

Over time, those small adjustments compound. Your credibility grows. Your presence strengthens. And senior conversations start to feel less like performances and more like what they’re meant to be.

A place where thinking moves forward and decisions get made.

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12. Why senior leadership conversations should always move thinking forward

Senior conversations are not meant to be comfortable updates. They exist to test thinking, surface choices and move the organisation forward.

When communication upwards is framed well, selective and intentional, something shifts. Meetings feel lighter. Questions become sharper. Decisions feel easier to make.

Not because the issues are simpler, but because the thinking is clearer.

This is the real aim of effective leadership communication. Not to impress. Not to explain everything. But to help others think well and decide confidently.

When you communicate with that purpose in mind, senior conversations stop being something to survive.

They become a place where leadership actually happens.

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