Paul Upton

Want to get to your next Career Level? Or into a role you'll Love? ◆ We help you get there! | Sr. Leads ► Managers ► Directors ► Exec Directors | $150K/$250K/$500K+ Jobs

"With no exaggeration- Paul and the LeaderUP program changed my life!" – James
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👉 Message me on LinkedIn

Why Senior Leads, Managers, Directors & VPs choose to work with me:
▶️ You want to break into your next leadership role, get promoted, or move to a promotional opportunity. Maybe you are seeking to break into your next level or senior leadership.

▶️ You're stuck in your current role, not much company growth, or growth opportunities. Or you do not like your current company/role and want to find a better one and level up your career to the one you deserve!

▶️ You're in a job search, you know you are good, but something is missing, you are not getting interviews, or are not getting offers!

▶️ You're tired of being frustrated & wasting time!

𝐀𝐛𝐨𝐮𝐭 𝐦𝐞: I've spent the last 14+ years working at top Fortune 100 companies.
◾️ 10+ jobs over this time and 2 highly competitive leadership programs
◾️ 7 times promoted/found promotional opportunities (often they found me)
◾️ Most recently an executive director at a telecom leading an organization of 150+ people.

𝐈𝐧 𝐭𝐡𝐢𝐬 𝐭𝐢𝐦𝐞 𝐈'𝐯𝐞 𝐥𝐞𝐚𝐫𝐧𝐞𝐝:
◾️ What it really takes to stand out in the Top 1% of leaders
◾️ How to be a great leader and more importantly how to develop this in others
◾️ How to hire the best, I've done over 500+ interviews and hired multiple high performing 10X teams

I am one of the few career coaches who has leadership/hiring manager experience and knows what they are looking for!

𝐍𝐨𝐰 𝐈 𝐰𝐚𝐧𝐭 𝐭𝐨 𝐡𝐞𝐥𝐩 𝐘𝐎𝐔 𝐚𝐜𝐡𝐢𝐞𝐯𝐞 𝐌𝐎𝐑𝐄 𝐒𝐔𝐂𝐂𝐄𝐒𝐒!

I have put these learnings together and have created the 𝐋𝐞𝐯𝐞𝐥𝐔𝐏 𝐋𝐞𝐚𝐝𝐞𝐫𝐬𝐡𝐢𝐩 𝐓𝐨𝐩 1% 𝐂𝐚𝐧𝐝𝐢𝐝𝐚𝐭𝐞 𝐂𝐨𝐚𝐜𝐡𝐢𝐧𝐠 𝐏𝐫𝐨𝐠𝐫𝐚𝐦 to help leaders and aspiring leaders reach the next level and land their dream jobs/promotions. 

Are you someone who wants...
✅Wants more MONEY, TIME, FLEXIBILITY, and GROWTH?
✅Gets multiple offers and CHOOSES the best one for them?

And would rather...
✅Follow a proven step-by-step process that works!
✅With the 1:1 support, you need along the way!
✅That takes 70% less time & effort and 99% less frustration!
✅And finally, get that dream job that they deserve and are excited to jump out of bed for?

► LeaderUP Job Offer System & Coaching Program -  Reach out to learn more!

👉 Learn more: message me!

Founder, CEO & Chief Career Officer - Career Expert | Career Success Coach | Leadership Coach

👉 Message me on LinkedIn

I am one of the few career coaches who has Fortune 50 leadership & hiring manager experience. This gives me the perspective to know exactly what hiring managers (not just recruiters) are looking for in a Manager, Director, VP+, how to stand out, and what it really takes to be a top 1% Leader & Candidate!

I have partnered with recruiters, HR leaders, hiring managers, and leaders to understand and distill the most important qualities and traits of successful leaders and how to find these in candidates and develop them in leaders. 

Through all this and hundreds of interviews, I have learned what the Top 1% of candidates do and built a system that works to help leaders, aspiring leaders, and high performers learn these skills and get the jobs & opportunities they really deserve!

► I help YOU master YOUR resume + LinkedIn so you STAND OUT and get NOTICED

► I help YOU learn how to ROCK your interviews and build real, memorable connections with hiring managers & GET OFFERS!

► I help YOU learn the skills to negotiate like a PRO to get the best total compensation package possible

► I really care. My sole reason for LeaderUP is to help YOU find success and fulfillment in your career. Success YOU DESERVE and have earned by working harder, learning more, and putting in the effort to SUCCEED!

I have created the LevelUP Leadership Top 1% Candidate Coaching Program to help leaders get promoted and land their dream jobs using Top 1% Applicant Strategies, leveraging the top SECRETS learned from Expert Resume Writers, Recruiters, Hiring Managers, Leaders, and Top Candidates, as well as many failures, successes, and continuous improvement!

► LevelUP Leadership Top 1% Candidate Coaching Program

MESSAGE me on LinkedIn to learn more and how I can help you!
Email me at Leaderup.Program@gmail.com

I don’t believe in dream jobs.
I believe in leaders who build trust, respect, and great workplaces.

A dream job means nothing if the culture breaks you.

Every day, I see workplaces that:

❌ Hurt mental health
❌ Damage relationships
❌ Block real career growth

But I also see how the right leader can change everything.

Bad leadership looks like this:

❌ Keeping secrets
❌ Ignoring feedback
❌ Forgetting to praise
❌ Avoiding tough talks
❌ Letting bullying happen
❌ Not helping people grow
❌ Showing bias and losing trust
❌ Thinking only about their own gain
❌ Making random choices that confuse
❌ Playing favorites and dividing teams
❌ Giving too much work and burning people out

Great leaders do the opposite:

✅ Set clear goals
✅ Act with honesty
✅ Put well-being first
✅ Cheer for new ideas
✅ Listen and show care
✅ Stay open and honest
✅ Accept people as they are
✅ Share feedback that helps
✅ Give real trust and freedom
✅ Make everyone feel included

✅ Work together and lead by example

I have spent years leading teams and hiring top talent.

What I know is simple:

People stay for respect, growth, and peace of mind.

If you are searching for a new role,
Pray for a leader who lifts you up,
Not a title that sounds good on paper.

Everyone deserves a workplace where they can thrive.

♻️ Share this with someone who needs to see what leaders can do.
➕ Follow me for more on leadership and career growth.

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70 interviews. 0 offers.
Next 10 interviews. 7 offers.
Here's what I changed...

Same person.
Different approach.

Here’s what changed:

- I stopped searching for that “right” answer
- I realized every hiring manager wants something different
- I focused on building real conversation, not rehearsed responses

The truth is:

- No one is perfect
- No answer is perfect
- Most people interview well enough to get in the room

But what makes you stand out?

It’s connection.

Hiring managers remember who understands their pain
Who listens
Who asks the right questions
Who shows they care about the work

Here’s how I flipped the script:

→ I listened first
→ I spoke honestly about my experience (no buzzwords)
→ I asked what frustrated them most about the role
→ I shared how I could help solve those headaches

Winning interviews are not about being the “ideal” candidate.

They’re about being real.
Being relatable.
Showing you want to solve real problems.

If you want more job offers—work on building trust, not perfect answers.

How do you approach tough interviews?
Has connection helped you stand out?

Comment "Connect" below if you want to learn how to build relationships that get results.

HR: We're promoting someone else to Director.

Her: I've led this department for 3 years. We hit 147% of target.

HR: You're a strong performer, but we don't think you're ready for leadership.

Her: Who did you select?

HR: Someone from outside. He has "executive presence."

Her: What does that mean?

HR: He interviews well.

---

She trained that external hire for 4 months.

He asked her how she built the systems that made the team successful.

She smiled and said nothing.

4 months later with LeaderUP's help,
So she could "interview well" too.

She accepted a Senior Director role elsewhere.

$65,000 more.
Direct reports: 34.
Scope: National.

Three weeks into her new role, her old company called.

"The new Director didn't work out. Would you consider coming back?"

Her answer: "No thank you."

---

If your company can't see your value, stop trying to convince them.

The right company will compete for you.

Not make you compete for recognition you've already earned.

Would you have waited—or walked?

♻️ Repost to help someone stuck in the same situation.

They reality was she was leading the entire department.

Stop waiting for your boss to decide you’re ready. Start acting like the market already has. 

Same talk.
Different year.

“You’re doing great work... but not ready yet.”

Next year:

“Love your impact... need more time in role.”

Year three:

“Keep doing what you’re doing... almost there.”

Meanwhile:

• “Not ready for VP” but you lead VP-level initiatives  
• “Need more experience” after you deliver $2M in results  
• “Work on visibility” while you train executives in every town hall  

You are not “not ready.”

You are not their priority.

The truth is:

• Readiness is subjective  
• Promotions are political  
• Gatekeeping hides behind “development feedback”  

You sit in calibration meetings as a fly on the wall.

They say:

“Let us see one more year.”  
“Who would back this promotion?”  
“Can we afford to lose them if they leave?”  

Those decisions say more about their risk and budget than your talent.

Here is your permission statement:

You do not need their permission to know your worth.  

You do not need one more “stretch assignment” to prove what you already do.  

You do not need to stay stuck in “almost ready” while others leapfrog you.  

The moment I started working with someone outside my company who could look at my skills without politics or history, everything changed.

We mapped my real scope.  
We priced my value to the market.  
We built a story that matched my impact, not my title.

Offers showed up from places that saw me as already ready.

You are not asking for a favor when you level up.

You are correcting an outdated view of your value.

How many years have you been “almost ready”?

Exceeded all goals.
Still got “Meets Expectations.” That’s not feedback, that’s politics.

My performance review made no sense.
Until I realized it was not about performance.

Here is what it said:

- “Exceeded all goals” → Rating: Meets Expectations
- “Strongest quarter in 3 years” → “Room for improvement”
- “Led the most successful launch” → “Needs more visibility”
- “Team retention at 95%” → “Work on leadership presence”

Director title.
Top results.
Blocked promotion.

Every time I asked what to do next, the answer changed.

One quarter it was: “You need more cross functional impact.”
I did that.

Next quarter it was: “You need more executive presence.”
I did that.

Next cycle: “We need to see this level sustained longer.”

When the goalposts keep moving, you are not playing the game.
You are the game.

The truth is: that review was not about my growth.
It was about their needs.

They needed:

- My numbers high
- My team stable
- My cost in the same box

Working with a career strategist was the shift.

They helped me see the pattern:
They needed me performing, not promoted.

Once I saw that, everything changed.

I stopped chasing vague feedback.
I stopped waiting for permission.
I built a plan to get to a place that matched my value.

If your review says “excellent work” but your rating says “stay in your lane,” that is data.
Not about your worth.
About their priorities.

Has your feedback ever contradicted your results?

Imagine training someone for 6 months.

Then hearing they’re your replacement for the VP role you fought for.

That is what happened to a Director before they started coaching with us.

12 years in one company.
Top reviews.
Clear promise of “You’re next for VP.”

Then leadership came with a “development opportunity.”

“Can you mentor our new hire? Great exposure for you. A chance to show your leadership.”

For 6 months, they poured everything into that person:

- Strategy
- Stakeholders
- Politics
- How to run the team when things go bad

Late nights. Extra calls. Deck reviews. Shadowing meetings.

Then the town hall.

“We’ve decided to go in a different direction for the VP role.”

The “direction” was the person they had trained.
Announced as VP.
Public praise.

No warning.
No honest talk.
No path forward.

They smiled, clapped on camera, then went home and broke down.

Here is what changed everything:

Working with a strategic career coach helped them see patterns they had been blind to for years.

- Loyalty did not lead to growth there
- They were already acting like a VP
- The market would pay for that level of impact

We rebuilt their story.
Repositioned their experience.
Targeted true VP roles.

In a few short months, they landed a VP position at a new company that valued their leadership.

40% pay increase.
Real authority.
Real respect.

Same person.
Different employer.

Sometimes the people holding you back are not your competition-they are your employer.

Has this happened to you?

If a reorg already has a deck and you never saw a draft,
you’re not being “aligned.” You’re being moved.

It is never “just a reorg.”
Someone benefits.
Someone loses.

A Senior Director I spoke with led a 15-person team.
High performer. Strong results. Great reviews.

Then one Friday: “Strategic restructure to drive efficiency.”

By Monday:
• Team cut from 15 to 3
• Scope reduced by 60%
• New org chart already in a polished slide deck

They were told: “You are still valued here.”

But here is what changed:
• Their “consolidated” team now sat under a less experienced leader
• Their title stayed the same, but the work got smaller
• They now reported to a former peer
• Key responsibilities were “redistributed” with no discussion
• The announcement went out before they even had a 1:1

The uncomfortable truth:
Reorgs are decided in closed rooms.
If you are surprised, you were not in the room.

When you see these signs, you are not paranoid. You are being messaged.

You are being told:
• “We want your knowledge, not your power.”
• “We want your name on the slide, not your voice in the room.”
• “We want you to exit yourself so we do not have to.”

Strategic leaders see the pattern early,
rebuild their story, and move to roles where their scope grows again.

They stop asking, “Why is this happening to me?”
They start asking, “How do I position myself before the next move hits?”

Have you ever been blindsided by a “strategic restructure”?

Dear Manager-turned-Job-Seeker:
The Applicant Tracking System (ATS) wasn’t built to find talent.
It was built to eliminate humans at scale.

Reality check
• 75% of your résumé never meets human eyes.
• “Must have 10 years of GenAI experience” = recruiter copy-paste, not a real requirement.
• Perfect keyword match? You just joined a digital cattle herd 300 deep.

Want interviews?
⭐ Bypass the bot. Get warm intros.
⭐ Solve a visible problem before you apply.
⭐ Talk to the budget owner—not the HR gatekeeper.
⭐  Position yourself in a compelling way.

Swipe left on the algorithm. Swipe right on real conversations.
Tag someone still obsessing over ATS scorecards.

Leaving after 1–2 years is not “job hopping” anymore.
It is risk management in 2026.

Markets shift fast. Reorgs hit fast. Layoffs hit fast.
You are not “unstable” for:

• Leaving after a Reorg that quietly erased your path to promotion
• Moving when your scope explodes but your title and pay stay flat
• Exiting a “stretch role” that stretches only your stress, not your skills
• Walking away when “next cycle” becomes the answer for the third year in a row
• Choosing a company that values your impact over one that values your silence

The uncomfortable truth:
They have a strategy for their org chart.
You need a strategy for your career.

From what I see with $150K–$500K leaders every week:

Leaders who stay “loyal” to the wrong company get:
• 2–3% bumps and vague promises
• More work, same title
• A slow leak in confidence and energy

Leaders who move with intention get:
• 25–30% pay jumps
• Real Director/VP scope
• Leaders who can state their value in one clear sentence

I lived this in my own path.
Every time I moved with a clear target and story, my career jumped.
Every time I waited “one more year,” growth stalled.

The new loyalty is this:
Loyalty to your future.
Loyalty to your health.
Loyalty to the leader you are becoming.

Companies that deserve you:
Build real paths, pay for impact, and treat you like a grown adult.

Companies that shame “job hoppers”:
Use guilt, low raises, and fear to keep strong people stuck.

Your career is not a lifetime sentence.
It is a series of strategic moves you make on purpose.

If you’re not being developed, paid, and positioned…
𝘀𝘁𝗮𝘆𝗶𝗻𝗴 𝗶𝘀 𝗮 𝗱𝗲𝗰𝗶𝘀𝗶𝗼𝗻 𝘁𝗼𝗼.

So choose one today:
A) Secure the internal path (with dates + scope)
B) Start the exit plan (quiet + intentional)

Comment “PLAN” and I’ll share the exact formula I use with $150K–$500+K leaders.

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He asked to leave early for his kid’s school event. Then he started to give me all the reasons. I told him, “You don’t need to explain. Just go.”  

Work from home? Fine.  
Come in late after a doctor’s visit? Fine.  
Block 2 hours mid-day for therapy, gym, or rest? Fine.  

I don’t need a full story for every calendar change.  
I need clear outcomes and honest communication.  

Here is what I care about as a leader:  
You deliver what you own.  
You keep your word.  
You support the team and the client.  

How you do that in a week will look different for everyone.  
Some move fast in the morning.  
Some hit their stride at night.  
Some need space in the middle to be a present parent or to take care of their health.  

The truth is: top talent does not stay where they feel watched.  
They stay where they feel trusted.  

When leaders obsess over chairs and clock time, they lose:  
Creative energy  
Real loyalty  
Their best people  

When they focus on impact and trust, they gain:  
Better decisions  
Stronger ownership  
Leaders who grow faster  

You are not a time-stamp.  
You are a leader delivering real results in a real life.  

The future of leadership is not “butts in seats.”  
The future is flexible work with clear expectations and real trust.  

How long will you keep treating grown leaders like kids who need a hall pass to live their lives?

HR: We would like to make you an offer of $265,000 plus a 30% annual bonus.

Candidate: Thanks. I'd like to have a deeper discussion. What does work-life look like on this team?

HR: It is a high-visibility role. Leaders here are expected to be “all in.”

Candidate: Can you be specific? What does that mean week to week?

HR: Most leaders are online late. Weekends happen when needed. We look for people who go the extra mile.

Candidate: Are there some clear boundaries around evenings, weekends, and vacations?

HR: At this level, we expect leaders to do what it takes to meet the goals.

Candidate: Then I will have to pass.

-

This is the shift I see every day with strong leaders.

They are not only asking:
“How much does it pay?”

They are asking:
“What will this cost my health?”
“What will this cost my family?”
“What will this cost my future self?”

Money is important.
Scope is important.
Title is important.

But so are:
Sleep.
Time with people you love.
Work you actually believe in.
Leaders who respect your limits.

The truth is:
Your next offer is not just a number.
𝗜𝘁 𝗶𝘀 𝗮 𝗹𝗶𝗳𝗲𝘀𝘁𝘆𝗹𝗲 𝗰𝗼𝗻𝘁𝗿𝗮𝗰𝘁.

You are not only negotiating salary.
You are negotiating 𝗵𝗼𝘄 𝘆𝗼𝘂 𝗹𝗶𝘃𝗲.

How long have you been saying yes to roles that cost you more than they pay you?

You prepare for the snow.
But do you prepare to enjoy your life?

Over the last few days, we had a lot of snow.
As the storm came in, we did what most people did.

We prepared.

• Bought salt for the driveway and sidewalk
• Stocked up on food and water
• Picked up a stack of library books in case we lost power

Lists, tasks, "need to do" items.
All important. All smart.

I saw how easy it was to stop there.
To only plan for problems.
To only prepare for what could go wrong.

But life is not only about clearing the driveway.

Life is also about the snowman.

In the middle of everything, we went outside.
We felt the cold air.
We rolled snow into big, heavy balls.
We built a snowman.

Simple joy.
Zero productivity.
High return.

Here is what many high performers forget:

• You prepare for risk, but not for joy
• You plan for work, but not for play
• You protect your time, but not your energy

In careers, it looks like this:

• You update the resume
• You grind for the promotion
• You say yes to more work

But you forget to design a life you enjoy living.

Next time you prepare for the storm, ask yourself:
Where is the snowman in your plan?

What would change in your career if you prepared not only to survive, but to enjoy your life too?

5 things you say in interviews that kill your chances. Stop making these mistakes.

“Thanks, I think we covered everything. I don’t have any questions.”

As a hiring leader, when I hear this, my brain says:

“Pass.”

The truth is: your words in an interview sell you or sink you. Fast.

Here are 5 phrases that quietly kill offers - and what I want to hear instead. ➡️

1) “I don’t have any questions.”

To me this says: low interest, low prep.

Say instead:
• “What are the top goals for this team in the next 6–12 months?”
• “If someone excels here, what do they do differently?”

Curious people win.

2) “I’ll take any job right now.”

I know the market is hard. I get it.

But desperation makes me think you say yes to any offer, any culture, any job.

Say instead:
• “I am focused on roles where I can use my strengths in X and Y.”
• “Here is why this role and company fit what I want next.”

Clear focus beats desperation.

3) “Autonomy is really critical for me.”

As a leader, I need people who can take input and still own strategy and results.

Say instead:
• “I value clear direction at the start, then space to execute.”
• “Helpful feedback from my leader helped me do X and Y.”

Coachability is a MUST at $150K, $250K, $500K+ levels.

4) “I don’t have any weaknesses.”

When I hear this, I hear: low self awareness.

Say instead:
• Name one real gap.
• Show how you work on it.
Example: “I used to avoid hard talks with my team. I worked on it by doing X. Now I do Y.”

Owning your growth is a green flag. ✅

5) “I'm looking for a challenge.  My last company didn’t really challenge me.”

I may agree with you inside, however, it sounds dismissive rather than driven.

Say instead:
• “I’m looking for a role that pushes me to learn faster and take on bigger challenges — your team’s projects sound like the perfect environment for that.”
• “I learned a lot there, but now I’m ready for bigger challenges to stretch my skills.”

If you’re ready to elevate your interview game and position yourself as a top performer — connect or DM me.  Let's get you the offer, not just the interview.

Yesterday, you said “after this reorg.”
Last quarter, you said “after bonus.”
Last year, you said “when the market calms down.”

There is nothing more painful than watching your career stay smaller than your potential.

7 brutal truths about staying stuck in the wrong role:

1. You “research” but never commit  
↳ Reading job posts is not a search. It is scrolling.

2. You update your resume more than your strategy  
↳ Resumes without a clear target are just decoration.

3. You wait for the “right timing”  
↳ Timing does not rescue you. Positioning does.

4. You have “reasons” your company will change  
↳ Hoping your boss wakes up one day is not a plan.

5. You fear a no more than you fear wasting years  
↳ A no is short term. A stalled career is long term.

6. You wait for confidence before you move  
↳ Confidence follows action, not the other way around.

7. You know this role is done for you but you stay  
↳ You do not need more signs. You need a decision.

The market is shifting with or without you.
Reorgs are planned with or without you.
Your title, pay, and peace move only when you do.

How long will you keep paying the hidden tax of waiting for “later” instead of building the role and life you actually want?

Share this with someone who has outgrown their role but is still on the fence about their next move.

The hardest problem is the one you keep avoiding. I used to waste years on easier wins.

In my career and in business, I learned to “optimize” everything.

New projects.
New tools.
New ideas.

But I was avoiding the real work.

The truth is:
Your biggest risk is not one stupid decision.
Your biggest risk is spending years on the second, third, and fourth best moves.

I saw this first as a leader.

We had teams that were “fine.”
Leaders who were “okay.”

But “fine” was the problem.

The real issue was culture and talent.
Fixing that meant hard talks, new standards, and turning people who were not a fit.
Morale dropped before it got better.

Six months in, it looked worse, not better.
But it was still the right decision.

The same pattern shows up in careers.

You:
• Tweak your resume again
• Take one more “safe” internal role
• Say yes to more work without more pay

All smart moves on paper.
All easy wins.

But you avoid the hardest problem:

• Your company will not grow with you
• Your boss will not promote you
• Your role will never match your potential

Real growth feels heavy.
Real growth feels slow.
Real growth can hurt before it helps.

Here is what I learned:

→ Name the hardest problem
→ Remove every distraction that keeps you from facing it
→ Give your solution time to work, even when it feels worse at first

Many of you have half-built bridges in your career.
You were one hard year away from a new level.
You quit in month one.

How long have you been avoiding the hard move that would finally change your career?

You are not “playing it safe.”
You are paying a secret tax for every 6 months you stay stuck.

You tell yourself you are “thinking about” your next move.
You read job posts, watch the market, update your resume a little.

But you do not have a clear strategy.
You are not moving with a plan.

In this economy, that has a cost.

Here is what 6 more months of “testing the waters” with no strategy often looks like:
• Same title
• Same pay
• Same manager
• Same stress

On the outside, nothing looks wrong.
On the inside, you feel it.

You start to pay a slow tax every 6 months:
• Confidence tax → you start to think you are “not ready yet”
• Energy tax → Sunday night feels heavy every week
• Health tax → your body is at home, your mind stays at work
• Money tax → you push back higher pay and bonuses
• Market tax → the market moves, your skills and story do not

I paid that tax in my own career.

I said: “I will move when the timing feels right.”
“I will wait and see what happens after this quarter.”

I watched postings.
I “thought about” moves.
I stayed passive.

Fast forward one year.
Nothing changed for me.
The market changed around me.

Here is the truth I had to face:
I did not have a career problem.
I had a strategy problem.

In a strong economy, you might get away with passive waiting.
You send a few random applications, take a call or two, and something lands.

Today that does not work.

Hiring managers want:
• Clear story
• Clear value
• Clear direction

If you are not clear, they move on fast.

What changed everything for me was when I stopped “thinking about it” and built a real plan.

Here is what I did:
• I chose the exact roles and levels I wanted
• I got clear on the impact I bring in numbers
• I mapped the leaders and companies I wanted to target
• I aligned their needs to my core strengths
• I set weekly actions for outreach, networking chats, applications, and interviews

Once I had the right strategy, doors moved faster.
Not slower.

Recruiters reached out.
Leaders saw me as a top 1% candidate.
Promotional offers showed up that matched my value.

The uncomfortable truth:
Waiting feels safe.
Passive “thinking” feels safe.

But with no strategy, you are not safe.
You are stuck.

In this economy, safety comes from:
• Clear direction
• Clear story
• Consistent action

Not from staying in place for “one more quarter.”

If you feel stuck in a role you have outgrown, you do not need 6 more months of thinking.
You need 6 months of focused strategy.

How would your career look 6 months from now if you stopped testing the waters and started moving with a real plan?

"We just cannot change the comp band. This is the max for your level."

After 6 years of “exceeds expectations” and extra projects, that is what their manager told them.

No real talk about scope.
No clear path to promotion.
No honest data on their market value.

So they stayed.
They told themselves it was safe.
They told themselves next year would be different.

Inside, something started to break.

Confidence dropped.
Energy dropped.
Self-worth dropped.

They stopped asking “What am I worth in the market?”
They started asking “Maybe this is all I get.”

Then a friend pushed them to get the help they needed and to test the market with a clear story and role target.

Four and a half months later, they had three offers:
• Same scope the company said was “too senior” for them
• $42,000 more than they thought was even possible
• Leaders who could explain their value in one clear sentence

That changed everything.

They did not just resign from a company.
They resigned from a low view of their own value.

Here is the truth I see every week with strong leaders:

• They accept “next cycle” instead of checking their real market value
• They wait for a title instead of acting like the owner of their career
• They tie their worth to one manager’s opinion and one pay band
• They do Director-level work while letting self-doubt grow

Your value does not start with a resignation letter.
Your value starts the day you decide to measure yourself by impact and market, not by one company’s limits.

You take control when you:
• Get clear on the roles and level you really want
• Put numbers to your wins so you see your own impact
• Test your story with real leaders, not just job boards
• Decide that “safe” is not safe if it shrinks who you are

The uncomfortable truth:
If you wait until you are broken to move, you carry that damage into your next role.

If you upgrade your view of yourself first, you upgrade every choice after.

How long have you been letting one company define your value?

The next promotion wave is not about more effort.
It’s about clearer positioning.

Here is what I am seeing with Managers, Directors, VPs right now:

They are not getting stuck because of skill.
They are getting stuck because nobody can clearly see where they fit next.

Emerging pattern:

• High performers keep stacking responsibilities
• Titles stay flat for 3–5 years
• Reviews say not “obvious next-level leader”

The shift in companies:

They used to reward loyalty and effort.
Now they reward leaders who are:

• Easy to “place” in the org chart
• Easy to “sell” to senior leadership
• Easy to “explain” in one sentence

In an AI, automation, and layoff-heavy market, your value must be simple and clear.
“Hard worker” is too vague.

What works now:

• Clear target: “Next 12–18 months I aim for Director of X / Head of Y”
• Clear brand: “I lead enterprise transformations that convert complexity into clarity—and strategy into measurable results.”
• Clear proof: 3–5 business outcomes you repeat everywhere, not a long task list

The uncomfortable truth:
If senior leaders cannot explain you in one sentence, they will not fight for your promotion.

In LeaderUP, when clients tighten their positioning, two things happen:

• More direct outreach from hiring managers
• More “You are exactly what we need” conversations in interviews

Not more hustle.
More clarity.

What would change in your career if everyone in your org could explain your value in one simple sentence?

If you never question your choices, you wake up one day and wonder: how did I get here?

Wrong company.
Wrong boss.
Wrong partner.
Wrong life.

You did not choose it.
You drifted into it.

I see this with leaders all the time.

They work like crazy.
They say yes to every ask.
They accept pressure at work and pressure at home.

Then one day they crack.

The truth is:
You do not end up here by one big decision.
You end up here by a thousand small ones you never question.

You say yes to the role you do not want.
You say yes to a culture that drains you.
You say yes to a life you did not design.

You stop asking:
What do I want?
Does this thing help me get it?

High agency starts there.

High agency is:
- Choosing your career on purpose
- Choosing your partner and friends on purpose
- Choosing your rest on purpose

Low agency is:
- Taking the job because “everyone would kill for it”
- Staying in a company that burns you out
- Letting others decide when you are “allowed” to rest

As a leader, you also shape agency for your team.

Your hard workers watch you.
If you never unplug, they will not unplug.
If you never say “take the day, unplug,” they will not feel safe to stop.

Support at home.
Support at work.
Clear choices about what you want.

That mix is where history gets made in your career.

Not by luck.
By design.

How long have you been living on default instead of design?

You don’t need another certification.
You need a clear target, a message, and a strategy.

A tech leader told me:
“I need more time. I want to prepare, refresh, study. Then I start my search.”

Six months later:
No offer.
More courses.
Same result.

Here is what I see with many smart leaders.

They say “I am getting ready” but they:
• Fear a no
• Hide behind more learning
• Hope the perfect role appears

Preparation feels safe.
𝗔𝗰𝘁𝗶𝗼𝗻 𝗳𝗲𝗲𝗹𝘀 𝘀𝗰𝗮𝗿𝘆.

The truth is:
More skills do not fix a weak story and a random search.

You can add:
• New tools
• New methods
• New cloud certs

If leaders do not see you as a clear solution, you stay a name on a list.

The leaders who land fast think in a different way.

They do not ask “Am I ready?”
They ask “𝗔𝗺 𝗜 𝗰𝗹𝗲𝗮𝗿?”

Here is what they lock in:

1) Clear target

→ One level
→ One main lane
→ One type of company

Not “any senior tech role.”
More “Director of Platform Engineering in B2B SaaS, 200–2000 staff.”

When you get this clear, you know who to speak to.

2) Clear message

Your value story sounds like a business case, not a job title.

Not “I manage teams and projects.”

More:
“I lead engineering teams that cut waste in the stack and unlock new revenue. I turn slow, costly systems into fast, lean platforms that pay for themselves.”

Short. Strong.
Money and impact in one line.

Leaders care about:
• More profit
• Less cost
• Less risk
• Faster delivery

Your message must say:
“I help you win here.”

3) Clear strategy

You stop hiding in job boards.
You start moving toward real people.

You:
• Reach out to hiring leaders
• Build warm links in your lane
• Treat interviews as talks about business, not school tests

You show how you solve their pain today, not how many things you know in theory.

You do not need six more months of “getting ready.”

You need a few focused weeks to choose your lane, sharpen your value story, and move with a real plan.

What would change in your career if your message spoke money and impact as clearly as your skills speak tech?

Grow Your Career 1% Daily - I’ll Show You How | Follow for Tips on Learning, Professional Development, and Productivity | Professor | MBA + JD

Is this the part where I talk about brand voice, distribution, and storytelling across the funnel? Or say we “help companies scale content that converts”?

𝗪𝗲 𝗱𝗼 𝗮𝗹𝗹 𝘁𝗵𝗮𝘁.

But what we really do is write content your team doesn’t have to worry about, so you can stay focused on strategy, not sentence structure.

𝗛𝗲𝘆, 𝗜’𝗺 𝗦𝘁𝗲𝗽𝗵𝗲𝗻. 👋

And my path here hasn’t exactly followed a playbook:
Banking → Law School → Teaching → L&D → Content

(Yeah… it’s been a ride.)

Today, I run a B2B content agency with my wife. We keep it lean and personal — just the two of us, plus our kids and a couple barky mini schnauzers. 

At Damn Smart Marketing, we give marketers writing they can trust and results they can stand behind.

✓ Content that sounds like you (not a template, not bland AI)
✓ Full support from idea to publication
✓ A partner who gets content
✓ Zero fluff, zero hand-holding
✓ More time to focus on what matters

In other words: you get to 🚀 while we handle the ✍️.

𝗟𝗼𝗼𝗸𝗶𝗻𝗴 𝗳𝗼𝗿 𝗮 𝘄𝗿𝗶𝘁𝗶𝗻𝗴 𝗽𝗮𝗿𝘁𝗻𝗲𝗿? 𝗧𝘄𝗼 𝘄𝗮𝘆𝘀 𝘄𝗲 𝘄𝗼𝗿𝗸:

1️⃣ 𝗗𝗼𝗻𝗲-𝗳𝗼𝗿-𝘆𝗼𝘂 𝘄𝗿𝗶𝘁𝗶𝗻𝗴 𝗳𝗼𝗿 𝗰𝗼𝗻𝘁𝗲𝗻𝘁 𝘁𝗲𝗮𝗺𝘀.
Blogs, LinkedIn posts, newsletters, case studies. If it’s got words, we’ll write it. You get to run the show without sweating every sentence.

2️⃣ 𝗟𝗶𝗻𝗸𝗲𝗱𝗜𝗻 𝘀𝘂𝗽𝗽𝗼𝗿𝘁 𝗳𝗼𝗿 𝗳𝗼𝘂𝗻𝗱𝗲𝗿𝘀.
We’ve built an AI-assisted workflow that makes posting easy, effective, and actually worth reading.

If you're curious, DM me. 

No cold, hard pitch, I promise. Just a real convo about where you’re headed and whether some damn smart content can help.

Stephen 😀

Stephen Mostrom

How my wife and I work together without losing our minds (or our marriage)...

9 years ago, Donna and I started Damn Smart Marketing.
4 years ago, we niched down to B2B content writing. 
24 months ago, I joined full-time. 

It's been a wild ride. 
Full of ups and downs. 

And, when we share our story with others, the same question comes up every time.

"How do you work with your partner 24/7 without killing each other?"

Here's our formula: 

1 - Love your differences (really!)
2 - Create a clear division of duties
3 - Remove pressure whenever possible
4 - Talk about everything
5 - Leave your ego at the door

Interested in learning more about how we make it work?

👉 https://lnkd.in/gtPzBpME

Writer for B2B Tech & Finance ✍️ | Running a content agency with my wife (and yes, still married) | Human words, AI workflows | JD & MBA

I've got one resolution for '26. 
KEEP. IT. REAL. 

Real talk
- Words I’d say out loud, not empty-calorie buzzwords
- Taking a stance, not performative "thought leadership"
- Posting for people, not the algorithm

Real content
- Heart-first drafts, not perfect-first outputs
- A voice with fingerprints, not generic AI fluff
- Photos that feel lived-in, not perfectly staged

Real-ationships
- Showing up first, not keeping score
- Chats that run long, not calendar Tetris
- Conversations with pauses, not pitches

LinkedIn.
The business world.
The internet.
Honestly, the whole globe.

It’s getting more synthetic by the second.

Time to swim against the current. 

Real only. 
No exceptions. 

You in?

LinkedIn friends: Can you help me get the word out?

I’ve got *a lot* of thoughts on writing, creativity, AI (and where to avoid it), and B2B marketing. 

(Also the last season of Stranger Things… but that’s a separate thread)

I’m looking to connect with smart folks who care about these topics and want to have no-fluff conversations around them.

If you know anyone I should meet, I’d appreciate a tag or a DM:

- Podcast hosts
- Conference organizers
- Speaking opportunities
- Or adjacent worlds I should be paying attention to

And if you just want to talk about The Upside Down or how Steve + Dustin are an elite duo, I’m here for that too!

Thanks in advance. 🙏

I assume every LinkedIn post will flop (yes, even after 1M+ impressions). So, I run mine through this 10-point checklist before hitting publish.👇

The result?

10k+ followers
Viral client posts
Countless connections

Here's the checklist: 

1. Did I start with the good stuff?
Weak hook, no go. I’ll tweak it 100x to get it right.

2. Does this post sound like me? (Or like AI?)
Beep boop. No thanks, I’ll stick to Stephen writing. 

3. Did I make it easy to read?
No one’s reading bland blocks of text during their coffee break.

4. Did I paint the picture?
Feelings, stakes, pain. That makes a story real. 

5. Will I remember this tomorrow?
If it’s forgettable to me, it’s forgettable to them.

6. Am I talking to one person, or broadcasting to everyone?
Generic tone = generic results. I write to one reader and one reader only.

7. Did I edit out the filler?
Adverbs, clichés, throat-clearing intros. I cut them with a chainsaw.

8. Did I anchor it in lived experience?
Real stories beat abstract advice every day (twice on Sundays).

9. What’s the one thing I want someone to remember?
If my post has 6 points, it has no point.

10. Did I enjoy writing it?
If it felt like a chore, it’ll probably read like one too.

Your go-to?

Who in their right mind adds 25 pounds to their morning walk?

Umm....

Last year, I started wearing a weighted vest. Unless it's 110° or more, most mornings you'll find me with three dogs walking a mile loop around Chandler. 

Shoulders strained. 
Core (hopefully) engaged. 
CCR probably on repeat. 

It's the funny bit about exercise...

To get stronger, you have to intentionally do hard things. Lift heavy stuff, run when nothing's chasing you, or strap extra weight to your body. 

The reward?
Growth. 

Problem is, when I look at the mental side of work, all I see are shortcuts. AI wasn't the first, but boy is it the loudest. 

"Write 100 LinkedIn posts in 30 seconds!"
"Turn one idea into a week of content!"
"Hit publish without ever breaking a sweat!"

There’s absolutely a time and place for speed, efficiency, and productivity.

But if everything gets easier…
When do we actually get stronger?

This isn't theoretical. 

Darja Djordjevic (Columbia Univ) on AI: 
“Here is a machine that is always available, endlessly enthusiastic, and seemingly competent in every domain. That creates a powerful feedback loop. You skip the discomfort of starting from scratch and get rewarded in seconds.”

Great for the short-term. 
Hazardous for the long. 

That's why I'm personally putting on weighted vests at work, too. 

Writing the first draft from scratch.
Sitting with the mess before cleaning it up.
Thinking before prompting.

Do I use AI? Of course.
But it’s the spotter, not the lifter.

Because the discomfort *is* the workout.

Maybe I'm not in my right mind. 
Maybe that's okay... as long as I'm growing. 🤷

Last year, I ghostwrote on LinkedIn for a dozen execs. 12M+ impressions, 20k+ followers. Here are 4 post types that delivered (and why): 

1. Scar stories

Easily our top-performer. 

What were the bottom-rung moments in a career (fumbles, toxic peers, etc)? And, most importantly, what did you learn from them?

One six-figure impression post from last year started with, “When I left the boardroom, I thought I was fired.” 

These posts counter the perfect upward path so often embedded in thought leadership content. 

They take courage to post. 
And that’s why they work. 

2. Non-obvious + niche trends

Market trend posts work when you’ve got a one-of-one view. 
And genuine thought leaders do. 

The key is making sure the trends don’t sound like an economics report. 

They need to cut deep for your target audience. 
Show you’re in the trenches. 

Not “5 [industry] trends,” but “5 patterns showing up across every [industry] conversation I’m in.”

3. Have you seen?

This is the small-scale side of the trends conversation. 
Commenting on news happening right now, this minute. 

- Major shakeup in your industry
- Big, bold stance by leadership
- Real-time data that informs decisions

In one move, you bring your readership into the fold (“have you seen?”), then lay out your angle (“here’s how I see it”). 

Timely and opinionated. 

4. I used to think X, now I think Y

Growth is interesting. 

People love to map the trajectory a leader’s taken. They want to see the nitty-gritty thoughts that shape million-dollar (billion-dollar?) leadership. 

One post that caught fire last year…
 
It broke down the people side of a data-heavy business. “I used to think the numbers mattered most, now I think it’s those small hallway conversations.”

Growth. And how it happens. 
Your readers can easily take notes. 




What do these posts have in common?

- Specific to YOU, not just anyone
- Getting real with your struggles and journey
- Putting the “thought” in thought leadership

That’s what separates the leaders people sync with…
From content that gets scrolled past and forgotten.

This might be my favorite January reading stack ever ↓

📚 How fear shaped history, politics, society, and more 
📚 One man's journey to consume the entire encyclopedia britannica
📚 The economist behind "Capital" takes on current events
📚 AI's impact on human writing (hint: it's not good)
📚 A globetrotting journey via classic works of fiction

What are you reading?
(Recommendations, please! I'm building my list for next month)

I'm tired of reading LinkedIn posts stuffed with fluff. 

Too many words. Too little payoff. A waste of everyone's time...

The result:
Writer – Annoyed that their message isn't resonating. 😡 
Reader – Annoyed that their attention isn't respected. 😤 

Who's this working for?
Answer: no one.

Time to get back to an old writing rule I swear by, "Every word not working for you... is working against you." 

Time to ditch words that add nothing. 

↓↓↓
These are the 4 worst offenders I see every single day: 

1. Buzzword Bingo
“Leverage”
“Synergy”
“Thought leadership”
“Game-changing”

2. The Warm-Up Lap
“I’ve been thinking a lot lately…”
“I wanted to share a quick thought…”
“This might resonate with some of you…”
“Just some reflections…”

3. Captain Generic
“Bet on yourself.”
“Show up.”
“Do the work.”
"Success isn't linear."

4. Say It Again, But Louder
“In other words…”
“Put simply…”
“Let me explain…”
“To clarify…”

Instead of fluff, do this...

Get to the point. 
Respect your reader. 
Mic drop and move on. 

Yeah?

Buffer crunched 2M+ data points to answer the question: How often should you post on LinkedIn to maximize reach? ↓

2-5 times per week. 

Doesn’t have to be every day. 
Doesn’t have to destroy your calendar. 

But moving from “whenever I have time” or once a month to this range yields serious results. 

+1,182 more impressions per post
0.23 percentage point lift in engagement rate

Buffer calls it “flipping a switch.”

That’s why, when we work with busy execs and founders at Damn Smart Marketing, we use a simple 3 / 30 approach: 

3 → publish three posts per week (minus holidays)
30 → one 30-minute weekly brainstorm to generate raw ideas

(Huge shoutout to Devin Reed, who runs this process to perfection. His breakdown is worth a look: https://lnkd.in/gcghEk5R)

That’s it. 

The difference between fading into the background and showing up in the feed of the people you want to reach. 

Questions?
Drop them below or DM me.

It's official: most folks DO NOT want to read AI. 

I've suspected as much. Seen loads of spiky posts about it on LinkedIn. But this is 4,484 people casting their vote, and you can see...

Only 16% keep reading, no problem. 
Whoa. 🤯 

My thoughts: 

1 - This topic is emotional quicksand. 4k+ people voting on a LinkedIn poll... that crazy, and a signal that people REALLY care. 

This isn't a shoulder shrug.  
It's a raging fire we need to pay attention to. 

2 - How do you know something was written by AI? Short answer: you don't. Instead, we're all judging in seconds. 

Is it flat, lifeless? Could anyone have written it? 
Does it have an em dash or too many rule of threes?

There's no rulebook. 
Just people making assumptions. 

As writers, marketers, and content folks...
We have to know this. Understand it. Adapt to it. 

3 - Content is about making bets. Bets that something you create will resonate and lead to a conversation, trust-building, etc. 

Idk about you...

But I don't want to bet on 16% odds. The chance folks MIGHT ignore the AI of it all and keep reading anyway... even if ChatGPT can generate 1M words in 3 seconds.

The smarter bet? 
Write for people. Write what resonates. 

And at least according to this (pretty big) poll, that isn't AI. 



Ok, enough of my ramblings...
What do you think? 

P.S. Shoutout to Mel Barfield for doing the work.

This LinkedIn post should have been a snoozefest. ↓

Instead, it's one of the best examples of writing voice I've ever seen. 


We've all seen the new furry friend angle.
Usually it's “I got a pup! 🐶” and 5 likes.

But not Lauren. 

Check it…

1 - She pulls you right into the storyworld

“middle of the workday” → busy CEO
“puppy with bad eyes” → awwww
“definitely don’t need another dog” → tension
“skin of our gahdayum teeth” → relatability
“ohmygaaaahhhh” → human emotion
“drive four hours” → commitment

And then there’s her backstory:
“lost… one year ago this week”
😭😭😭

2 - She uses (gasp) humor

Pile of laundry?
Mitch McConnell? 

I won’t explain the funny here cause that ruins it. 
But c’mon. This is standup level. 

3 - She sounds so human

Running around at 1 million miles per hour. 
Making heartfelt decisions. 
Talking pup names with her husband. 
Reflecting on the past and looking to the future. 

All in 115 words. 



I’ve never met Lauren. 
Never seen her content on LinkedIn before. 
But you can bet I smashed that “like” button fast. 

And last I checked, 1000+ others had too. 

Wow. Great writing. 
Who knew?

“Have AI write the first draft, then edit.” 

I know smart folks who write this way. It works for them. Real talk, though, it's not how I do my best writing.

Here's why: 

1 - The 1000-pound anchor. 

Once words are on the screen, they’re hard to ignore. You start reacting to what’s there instead of imagining what could be.

That usually means less human judgment. Less original thinking.

You either have to edit hard and fast and often. 
Or you quietly settle.

2 - It’s painfully predictable.

AI leans on the same phrases, rhythms, and structures. Even when you tell it to mix things up.

So I’m left with two bad options:
- Everything I write starts to sound the same
- I spend time hacking and rearranging instead of thinking

Both feel like fighting the work instead of doing it.

3 - I want my creative muscles strong.

I plan to write tomorrow. And the day after that. And the day after that.

When I'm on a client call, I want ideas flowing straight from my brain (not from a prompt I used last week). 

That only happens with reps.

Staring down the blank page like it's a roaring dragon spitting flames. And coming out the other side untouched. 

---

My process instead: 

- I write the first draft, messy and human. 
- I get feedback from trusted peers and my co-founder. 
- I use AI for grammar, polish, and the occasional word swap.

That balance works for me. 
It protects originality without sacrificing speed or quality.

Curious how others do it.

AI-written first drafts?
Or human-first?

When execs and founders ask me how to win on LinkedIn, I give the same advice every time: Hook your reader. Here are 5 hook-writing tips👇

1. Know the fundamentals

Your hook = what shows before “see more.”
You’ve got about 200 characters to earn the click.
Make it count.

2. Use specific, emotionally charged words

Generic is boring. Stats are boring. I’ve seen enough posts start with a bland sentence + stat to fill a stadium.

Don’t aim for the head. Aim for the heart.

And use the words that speak to them...

Think:
– Burnout, not low engagement
– Ghosted, not no response
– Nightmare spreadsheet, not manual process

3. Inject your POV

There’s way too much “you should” on here. Try “I did” instead.

Personal stories beat generic advice every day of the week.

Simple formula:
Do interesting things. Talk about them.

4. Signal value early

If you’re sharing 5 tips, say that up front. Please don’t make people guess what they’re getting.

Clarity builds trust... fast.

5. Benefits, benefits, benefits

Assumption is a dangerous game on LinkedIn. The audience is too wide, too diverse.

So spell it out:
- Why should someone care? (benefit)
- What’s it going to help them do? (benefit)
- What’s the end result? (benefit)

If the value’s not obvious, they’ll scroll. Every time.


---
Your turn: What's your go-to tip for writing a standout hook?

I love love love movies. But "CGI slop" is ruining them. Every new Marvel, Jurassic, or Fast flick looks like a blender full of pixels and lens flares. And we’re making the same mistake with AI-first content.

Case in point:
Jurassic Park (1993): 60 CGI shots, 100+ practical effects.
Jurassic World (2015): 2,000+ CGI shots.

One still makes me hold my breath. The other makes me reach for my phone.

Why? Because you feel the T-Rex in Jurassic Park.
I get goosebumps every single time.

These days, my LinkedIn feed is overflowing with AI-first content.
Technically fine. But it feels hollow.
So it doesn’t land.

But get this…

One of our ghostwriting clients took the opposite route.
No visuals. No AI polish. Just a human-written, text-only post anchored in a painful moment from her career.

The result?
700k+ impressions.
Inbound leads.
Conversations with decision-makers who felt like they knew her.

Not because it was flashy.
Because it was real.

And that formula is working in Hollywood too.

The Boy and the Heron won Best Animated Feature with hand-drawn frames.
Godzilla Minus One won Best VFX on a $15M budget (up against a Mission Impossible movie with a $291M budget).

While the big studios keep chasing pixels, these outliers zagged and won.

It’s a simple truth:

Doing what everyone else is doing has never worked in content.
That’s not changing anytime soon.

Donna Mostrom calls our LLM “Cathy.”

Because we use ChatGPT.

Chatty Cathy.
Well played. 🫡

taplio

The Battle

Paul Upton

Stephen Mostrom

Followers

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Performance ScorePaul Upton's LinkedIn Performance

Performance ScoreStephen Mostrom's LinkedIn Performance

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taplio

The Battle

Paul Upton

Stephen Mostrom

Followers

Posts

Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Paul Upton's LinkedIn Performance

Performance ScoreStephen Mostrom's LinkedIn Performance

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Performance ScorePaul Upton's LinkedIn Performance