Ideas, analysis and communication insight for strategic thinkers in B2B tech
LEADERSHIP COMMS
The Executive Voice
Communicating Internally to Persuade the CEO
Research shows that the higher someone rises in an organisation, the more information competes for their attention and the greater the demands on their time.
Which means that if you’re preparing to communicate with your CEO, you should respect their time constraints and mental load by structuring your message around this 4-part formula:
a central point before discussion
a conclusion before background
a recommendation before methodology
consequences before operational detail
Example Using the 4-Part Formula
Let’s say the CIO asks for a meeting with the CEO to request replacing several disconnected finance, procurement and reporting systems with one integrated platform. Following the above message formula, it might sound something like:
“We need to consolidate our finance, procurement and reporting systems into one integrated platform. My conclusion is that the current fragmentation is now costing us time, increasing risk and preventing reliable decision-making. So I recommend we begin a staged replacement this year before the cost and disruption become significantly greater.”
Central point: consolidate the systems
Conclusion: fragmentation is now a business problem
Recommendation: begin a staged replacement
Consequence: delay will increase cost and disruption
Think Like A CEO
A CEO is looking for what’s best for the whole organisation, not an argument for one function or department.
Your recommendation will be stronger when it considers:
competing organisational priorities
the effect on other functions or business units
consequences for customers and employees
financial implications
the organisation’s capacity to deliver
likely stakeholder or internal resistance
what may need to stop, change or be delayed
The weak version is: “IT needs more funding to replace our outdated systems.”
This frames the issue as an IT need. Whereas the example above demonstrates how the CIO connected the problem and investment to the wider business.
Show Your Judgement
CEOs don’t expect you to arrive with every answer, but they do expect you to have done the thinking.
Bringing a problem without a view can suggest a lack of ownership. Arriving with only one fixed answer can look like lobbying for a preferred outcome.
Strong communication shows that you’ve considered alternatives, understood the trade-offs, and formed a clear recommendation, while remaining open to challenge.
The goal isn’t to do the CEO’s thinking for them, but to ensure their attention is focused on the decision only they can make.
The Interviews
‘Five Good Questions’ Series
A Conversation with Jeff Bogensberger
“We’re living in a fascinating time that is both exciting and scary. Technology is moving at such speed, but we’ve also been programmed to accept products that don’t work properly. I can’t remember the last time I signed up for a SaaS product that simply did what the website said it would … “ Read the Q&A, just a three-minute read, but plenty to think about.
REVENUE COMMS
Communication That Earns Influence
How to Sell to The CEO at Your Buyer
CEOs are combating economic uncertainty, geopolitical risk, slow market conditions, fiscal pressure and budget impacts. They’re also dealing with productivity pressures, cost reduction, scalability issues, talent gaps and increased scrutiny of their investment decisions, especially in AI.
Because they’re under pressure to make better decisions in an environment that is complex and high stress, their tolerance for vague promises is low.
Don’t approach CEOs with a conventional sales presentation where you outline a problem, present a solution, introduce some generic proof points, and close. This is what many technology sellers do, and most CEOs find this underwhelming.
Instead, your opening should establish why the issue belongs on the CEO's agenda, not why your product is impressive. It’s important to find out what the specific agenda is for your CEO buyer, but generally speaking, these are their priorities in 2026:
profitable growth and business reinvention
productivity and measurable returns from technology
resilience against geopolitical and supply-chain uncertainty
workforce capability and AI readiness
risk, governance and trust
faster execution without reckless investment
It’s important to get inside their head and speak to these types of priorities easily and naturally.
A CEO Must Be Able to Defend Your Solution
Next, a persuasive CEO conversation should provide material that makes the decision easier to defend internally, and thus CEOs are likely to value the following:
relevant customer outcomes rather than a long customer list
quantified value with assumptions disclosed
realistic time to value
independently validated evidence
a comparable implementation
acknowledgement of failure conditions
a practical way to test the central claim
They want value expressed at the enterprise level, not at the level of the product or function. This means your presentation about your solution needs to answer these questions:
What does that do to revenue, margin, risk or strategic capacity?
Does it improve customer retention or competitive position?
Does it release capital or management attention?
Does it make an existing strategy more executable?
Does it allow the business to enter a new market or defend one?
Does it reduce the possibility of a serious failure?
Finally, not every proposition needs an exaggerated ‘business transformation’ claim, but your solution needs to ‘honestly’ connect to a business consequence the CEO cares about.
Strategic Insights
Throw out your vision & mission statements
Instead lead with a message how your company will think, decide and adapt in the second half of 2026.
MARKET PULSE
In The News
This week, two examples of how CEOs are communicating to the marketplace and where the gaps lie in their communication.
Monday.com Calls Layoffs an AI Growth Strategy
Monday.com announced plans to cut around 20% of its workforce as it shifts towards what co-CEO Eran Zinman called an “AI-driven growth strategy”. In a memo to staff, the company said it would create a flatter structure with more autonomous teams while continuing to hire in selected strategic areas. Zinman insisted the changes were not simply about reducing costs or replacing employees with AI. The announcement comes after Monday.com’s share price fell substantially over the past year.
What Rings False About This Communication?
The memo explains the strategic rationale in considerable detail and the co-CEOs clearly accept responsibility for the decision. However, the language of empowerment risks sounding more aspirational than believable.
Google’s Strong Results are Overshadowed by AI Spending
Alphabet reported stronger-than-expected revenue, driven by rapid growth in Google Cloud, but increased its projected 2026 capital spending to between US$195 billion and US$205 billion. The scale of its AI infrastructure investment contributed to negative quarterly free cash flow and unsettled investors, despite the strong results. CEO Sundar Pichai defended Google’s broader AI position and rejected suggestions that the company was falling behind competitors.
What’s Missing From the Communication?
Pichai highlighted strong growth, but investors want to know how Alphabet will control rising AI costs, measure returns and respond if revenue slows.
Phrase of the Week
Decision-ready Communication: Presenting information that doesn’t simply inform the CEO, but helps them decide.
QUOTE OF THE WEEK
”Our AI investments are redefining what’s possible across every part of our business.“
SOMETHING EXTRA
Useful Prompt: Prepare To Sell To A CEO
Use this prompt to pressure-test your sales proposition to a CEO and shape a clearer, more credible business case for them.
THE PROMPT
I am preparing to speak with the CEO of [company] about [solution, service or business issue].
Act as a commercially experienced CEO and strategic sales adviser. Help me build a persuasive argument from the buyer’s point of view, not from my company’s or product’s point of view.
Here is the information I currently have:
The company: [industry, size, business model and relevant background]
The CEO’s likely priorities: [growth, margin, risk, customer retention, productivity, market expansion, etc.]
The business issue or opportunity: [describe it]
My proposed solution: [describe it plainly]
Evidence available: [customer results, data, research, case studies or proof]
Assumptions or estimates: [list them]
Known risks or objections: [list them]
The next step I want: [meeting, assessment, workshop, trial, commercial discussion, approval, etc.]
Use the following seven-part framework to help me prepare:
Establish relevance quickly
Identify the business, market or strategic priority that makes this worth the CEO’s attention now.Make the consequence clear
Explain what the organisation could gain, lose or risk by acting, delaying or doing nothing.Bring a useful point of view
Develop an insight that goes beyond generic market commentary or product claims. It should help the CEO see the issue differently.Separate evidence from assumptions
Clearly distinguish what is proven, what is estimated and what still needs to be tested.Address risk before being asked
Identify the drawbacks, dependencies, implementation risks and likely internal resistance. Explain how each could be reduced or managed.Make the next decision manageable
Recommend the smallest sensible next commitment. Do not assume the CEO should approve the entire solution immediately.Help the CEO make the case internally
Create a concise proposition the CEO could credibly explain to the CFO, board and affected business leaders.
For each of the seven points:
assess the strength of my current thinking
identify what is missing, vague or unsupported
ask only the questions needed to improve it
challenge product-led language, weak assumptions and exaggerated claims
rewrite the point in clear, commercially credible language
Then produce:
a one-sentence opening that would earn the CEO’s attention
a concise CEO-level argument covering all seven points
the three strongest pieces of evidence I should use
the three questions or objections the CEO is most likely to raise
credible responses to those questions
a clear recommendation for the next decision
a short internal explanation the CEO could repeat to the CFO or board
Keep the language direct, specific and free of sales jargon. Do not invent evidence. Mark any unsupported statement as an assumption or information gap.
Use this prompt to test your thinking, identify gaps and build a CEO-level argument before you enter the conversation.
If this helped you think differently about communication, forward this newsletter to someone who leads, sells or explains complex ideas in tech.
For a different perspective, subscribe to my other newsletter, THE STATIC, a weekly, 5-minute read that decodes the nonsense in tech hype and comms.
