The Thoughtful Executive is a weekly executive-level newsletter on thought leadership, content marketing, and strategic messaging for the C-suite. Delivered every Wednesday.
Welcome—or welcome back—to The Thoughtful Executive!
On this platform, we’ve talked about how to:
Choose thought leadership topics that actually matter
Develop a differentiated POV
Turn content into strategic intelligence
Keep a thought leadership program alive past 90 days
Make sure your exec’s voice actually comes through
And much more
Now, let’s zoom out.
You have the pieces. Now you need a way to see if the whole thing is working.
So here it is.
This is a simple health check you can run in 15 minutes to see whether you are running an executive thought leadership program that makes an impact or just a content calendar with executive bylines.
You can do this on your own. Or with your team. Or with your exec in the room if you are feeling brave.
How to grade your thought leadership program
You will be scoring yourself in five areas:
Challenges
POV
Intelligence
Systems
Voice
For each statement, give yourself:
1 point if this is true most of the time
0 points if it is rarely or never true
No half points. Force a decision.
At the end, add it up and see where you land.
1. How your program addresses challenges in the market
We talked about how to choose thought leadership topics that actually matter, not just whatever is trending or easy to write about. I explained how to move from anything related to product to real industry and customer challenges that your exec is actually wrestling with.
These questions are here to test whether that thinking has made it into your day-to-day.
Give yourself 1 point for each one that is true.
We focus most of our executive content on real industry or customer challenges, not generic leadership advice.
We can point to specific deals, product decisions, or strategy conversations that shaped the topics we choose.
We are not chasing every trend. We are willing to ignore topics that do not fit our point of view, even if they are hot on LinkedIn right now.
Score for Challenges: 0–3
2. Grading your executive’s POV
You’ve also done the work to build a differentiated POV. Not just “we care about customers” but a clear way your exec sees the world that is not interchangeable with your competitors.
These questions check whether that POV is actually showing up in what you publish or if it is still trapped in slides and internal conversations.
Our exec is willing to take positions that someone could disagree with.
We can clearly describe how our exec’s POV is different from at least two competitors.
When we publish, we are not just explaining what is happening in the market. We are saying what we think people should do about it.
Score for POV: 0–3
3. How your program gathers intelligence
We spent time on strategic intelligence for a reason. Thought leadership is not just about getting attention. It should send information back into the company. Customer reactions. Competitor moves. New questions from the market.
These questions help you see if your program is actually capturing that or if everything you learn from content dies in the comments section.
After we publish, we look at who engaged, what they said, and what new questions came up.
We capture that feedback somewhere the team can see. Not just in a social tool or a sales platform that one person checks.
At least once a month, we take something we learned from content engagement and change a message, a topic, or an asset because of it.
Score for Intelligence: 0–3
4. What systems you should have in place
We also talked about why most programs die around the 90-day mark. Recap: It’s not because the idea is bad. It’s because the system cannot survive launches, board decks, and everything else that hits a marketing team.
These questions are here to show you if you have enough structure to keep going when things get messy.
We have a simple, written process for how topics move from idea to published.
We have a standing time on the exec’s calendar for content. Not just ad hoc “when things slow down.”
When things get busy, our program bends but does not break. We might reduce volume for a bit, but we do not disappear for months.
Score for Systems: 0–3
5. Checking in on your executive’s voice
Next, let’s talk about executive voice. Not as a branding exercise, but as proof that the thinking on the page is actually coming from the person whose name is on it.
These questions help you see if that work is paying off or if your content still sounds like marketing with an executive label.
If you remove the exec’s name from a piece, people who work with them would still recognize it as theirs.
Our exec regularly marks up drafts, adds stories, or pushes back when something does not sound like them.
We can name at least one phrase, story, or way of framing problems that shows up in their content again and again.
Score for Voice: 0–3
How to read your score
Add up your points across all five sections.
You will have a score between 0 and 15.
Here is how I would read it.
0–5: You have a publication calendar, not a program
You are shipping content. That matters. But it is not yet functioning as executive thought leadership.
Common signs at this stage:
Topics come from campaign themes, not real challenges
Your exec is barely involved
You are measuring views and likes, not impact
If this is you, do not overhaul everything.
Pick one area and focus.
If you can only fix one, start with challenges. If you are talking about the wrong problems, no amount of polish will save you.
6–10: You are in emerging flagship territory
You have momentum, but it is uneven.
You see this when:
Some pieces hit hard, others disappear
Your best work happens when the exec leans in
The system works until something big hits the calendar
At this stage, small, focused changes move the needle.
For most teams, that means:
Tightening how you pick and vet topics
Making the feedback loop real instead of informal
Protecting a minimum cadence on the exec’s calendar
11–15: You are running a real program
If you scored this high and you were honest, you have something solid.
You have:
Clear, challenge driven topics
A recognizable POV
A basic intelligence loop
A system that keeps things moving
An exec whose voice shows up consistently
Your work now is less about fixing the basics and more about:
Showing impact in a way the business takes seriously
Stress testing your content in tougher environments
Scaling what you have without losing the core of it
What to do with this test
Do not treat this health check as a one-time exercise.
You can use it as:
A quick self audit every quarter
A conversation starter with your team
A way to frame trade offs with your exec
Start simple.
Run it alone. Mark where you think you are strong and where you are not.
Then share it with your team. Ask them to score it separately. Talk about the gaps in how you see things.
If you have the trust, bring a light version to your exec. Not as a performance review. As a way to say here is where this program is carrying its weight, and here is where it is not yet.
FAQs about executive thought leadership programs
What is an executive thought leadership program?
An executive thought leadership program is a structured initiative that positions a C-suite leader or senior executive as a trusted, credible voice in their industry. Unlike standard content marketing, it centers on the executive's unique perspective, real-world experience, and differentiated point of view rather than product messaging or generic leadership advice. A successful thought leadership program connects an executive's judgment to real industry and customer challenges—and turns that into high-quality content that builds trust with decision-makers over time.
How do I know if my thought leadership program is actually working?
Use a simple benchmark like the health check in this article. Score yourself across five areas—challenges, POV, intelligence, systems, and voice—and look for patterns. Effective thought leadership shows up in more than just metrics like views and likes; it influences deals, shapes messaging, and sends strategic intelligence back into the business. If your thought leadership content is not changing conversations internally or earning engagement from your target audience, it is likely functioning as a publication calendar rather than a program.
What metrics should I use to measure thought leadership?
Go beyond surface-level content marketing metrics. Track engagement quality (who is responding, not just how many), lead generation tied to thought leadership pieces, and whether content is influencing pipeline conversations. Also look at qualitative signals: Are stakeholders referencing your executive's content in sales calls? Are subject matter experts inside the company sharing it? Are decision-makers engaging on LinkedIn or social media? The best metrics connect thought leadership efforts directly to business goals and business objectives.
What makes someone a true thought leader versus just a content creator?
A true thought leader takes positions that someone could disagree with and offers a unique perspective grounded in real experience—not recycled advice. Their point of view is clearly differentiated from competitors, and they are willing to say what they think people should do about a problem, not just describe what is happening. Thought leadership content from a real thought leader reflects their actual voice, stories, and way of framing issues, which builds trust in a way that polished but generic content never can.
What formats work best for thought leadership content?
The best formats depend on your target audience and business goals. Long-form articles, white papers, and original research work well for establishing depth and credibility with decision-makers. Webinars and podcasts humanize the executive and create real-time engagement that builds trust. On social media—especially LinkedIn—shorter thought leadership pieces and case studies can drive brand awareness and reach new audiences. The key is to repurpose your strongest thought leadership content across multiple formats rather than creating everything from scratch.
How do I keep a thought leadership program alive when things get busy?
Most thought leadership programs die around the 90-day mark because the system cannot survive competing priorities—launches, board decks, and everything else that hits a marketing team. To prevent this, your marketing team needs a written process for how topics move from idea to published, a standing time on the executive's calendar for content (not ad hoc), and a minimum cadence the program can fall back on without disappearing entirely. The goal is a system that bends but does not break.
How involved does the executive need to be?
The executive does not need to write every word, but their voice must be present. That means they should regularly mark up drafts, push back when something does not sound like them, and contribute the stories and framing that make the content authentically theirs. Without that involvement, you end up with expensive blog posts under an executive byline that do not land with stakeholders or build the connection flagship content is supposed to create. Even entrepreneurs and founders with limited time can maintain involvement through structured, brief input sessions.
Can thought leadership support goals beyond brand awareness?
Absolutely. A well-run thought leadership strategy supports retention, recruitment, media coverage, and public relations—not just top-of-funnel visibility. Thought leadership pieces backed by original research or innovative ideas can earn inbound interest from influencers, journalists, and potential partners. When aligned with business objectives, a thought leadership program becomes a strategic asset that drives real pipeline impact rather than just brand awareness.
How do I get started if I scored low on the health check?
Do not try to overhaul everything at once. Pick one area and focus. If you can only fix one thing, start with challenges—if your content is talking about the wrong problems, no amount of polish or marketing strategy will save it. From there, build out your content strategy by identifying your executive's differentiated POV, establishing a simple system to keep the initiative moving, and gradually incorporating a feedback loop that turns audience engagement into valuable insights for the business.
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Johnathan Silver helps executives turn judgment and experience into effective thought leadership. Through The Thoughtful Executive, he works with senior leaders and marketing teams to build thought leadership programs, sharpen executive voice, and create content that earns trust over time. His work sits at the intersection of leadership communication, content strategy, and executive decision-making.