Is rapid growth creating More Problems Than Solutions?
Don’t let hidden organizational challenges derail your momentum.
The faster your business grows, the more critical it becomes to manage the underlying challenges. Identifying and resolving these growing pains now can secure your continued success.
BEFORE YOU START
A CEO recently said: “Revenue up 20%, but we’re rebuilding the same processes twice. I need to know: is this normal scaling tension—or are we 6 months from something breaking?”
Another: “We’re growing fast. I just want to know if our infrastructure can sustain this—or if we’re building on sand.”
This assessment shows you where you stand—and how much time you have.
12 minutes. Direct questions. The ones that reveal whether your infrastructure matches your growth trajectory.
One CEO told us: “I scored it optimistically first. Then retook it from my COO’s perspective. 18-point gap. The second score showed me we had about 120 days before critical failure. We fixed it in 90.”
Your team already knows what’s straining. This shows you where to focus—and how urgent it actually is.
Take it honestly—it’s most valuable that way.
DOES THIS SOUND FAMILIAR?
“We’re scaling fast. I’m just not sure our systems can hold another 12 months at this pace.”
“Lost a star VP. Exit interview: ‘I rebuilt the same supply chain twice. Can’t do it a third time.'”
“Team’s working harder than ever, but delivery times keep slipping. Something’s breaking.”
“My COO says: ‘This pace isn’t sustainable past Q3.’ I know she’s right. But where do we even start?”
“Attrition’s climbing. People aren’t leaving for more money—they’re exhausted from broken systems.”
Real quotes. CEOs running $20M-$500M companies.
Good news: These patterns are predictable. And fixable—if you catch them in time.
If any resonated, this assessment shows where to focus first—and how much runway you have.
How This Assessment Helps
Shows Which Fixes Buy You the Most Time
Not everything broken needs fixing. Some repairs buy you 12 months of breathing room. Others buy you 30 days.
Identifies What's at Risk in the Next 90-180 Days
Separate genuine threats from manageable growing pains. See what needs immediate attention.
Reveals Where Your High-Performers Are Stuck
Are they building with you—or managing their departure timeline because systems keep breaking?
Maps Your Realistic Timeline
Shows you what's fixable in 30 days, 90 days, 6 months—and where you need help vs. can handle internally.
How it Works
Your Path to Solving Growth Challenges
Step 1
Answer 20 Questions Honestly Takes 12 minutes. Each question surfaces operational fractures you've been managing as "normal scaling chaos."
Step 2
See Where You Stand Your score shows severity and timeline—from "fixable with focus" to "90-180 days from critical failure."
Step 3
Map What's Actually Fixable Book 30 minutes. We'll show you what's realistically fixable, in what timeframe, and whether you need embedded help.
Most Common Questions
Have a different question for our team?
What is this assessment?
A 20-question diagnostic that shows whether you’re building infrastructure ahead of growth—or whether operational strain is starting to create risk. Won’t tell you things you don’t know. Shows you where to focus first—and how much time you have.
How long does it take?
12 minutes if you answer honestly. Less if you’re scoring how you wish things were instead of how they are.
What results will I get?
A score and timeline showing where you fall from “healthy infrastructure with manageable stress” to “3-6 months from a forcing event.” Not a 47-point diagnostic breakdown. A mirror showing what needs attention and how urgent it actually is.
Who should take this?
Take this if you:
- Run a $10M-$250M company that grew faster than infrastructure could support
- Are losing high-performers you can’t afford to lose
- Privately acknowledge things are unsustainable but don’t know where to start
- Have been burned by consultants who left decks but didn’t fix anything
- Want validation that everything is fine
- Aren’t willing to see operational reality your team already knows
- Prefer avoiding uncomfortable truths about infrastructure gaps
Why is this free?
Because CEOs who score above 35 already know they need to address infrastructure—they’re just deciding how urgent it actually is and who can help. his assessment shows you we understand your specific operational pattern and can accurately predict your timeline. The diagnostic call shows you whether we’ve solved this exact problem before—and how long it actually took. We don’t need to charge for the diagnostic. We charge for the systematic rebuild.
What happens after I see my score?
You can book a 30-minute diagnostic call where we map:
- What your score reveals about infrastructure strain points
- How much runway you have before strain becomes a crisis
- What’s realistically fixable in what timeframe
- Whether embedded operational help makes sense—or if this is fixable internally
No pitch. No deck. Just an honest conversation about what’s broken, how much time you have, and what it takes to fix it. GROWING PAINS ASSESSMENT – this is
ASSESSMENT QUESTIONS
1. Leadership Clarity Cross-functional decisions: everyone knows who has authority without needing "alignment meetings about alignment meetings."
2. Process Permanence Workarounds from 18 months ago are still in place—we haven't had bandwidth to replace them with permanent solutions.
3. Talent Retention Signal High-performers cite "growth opportunities" when leaving—but exit interviews reveal frustration with rebuilding the same broken processes.
4. Approval Bottlenecks Routine decisions require 5-7 sign-offs—we've added approval layers as we've grown, without reviewing if they're still needed.
5. Initiative Fatigue Launched 3+ "transformation initiatives" in 12 months—but none fully delivered the intended operational changes.
6. Consultant Graveyard Hired consultants who left recommendations without execution support—we're still searching for partners who implement, not just advise.
7. Strategic Skepticism All-hands announcements met with visible skepticism—team has seen "strategic priorities" stall in planning phases before.
8. Meeting Overhead Best people spend more time in "alignment meetings" than executing—we wonder why nothing ships on time.
9. System Failures Core systems (CRM, ERP, project management) break or fail weekly—we've normalized this as "just how it is."
10. Promoted Too Fast Promoted people to solve problems—realized we made them part of the problem without supporting infrastructure.
11. EBITDA Erosion Revenue grows, EBITDA flat or shrinking—rationalized as "investment in growth" instead of operational inefficiency.
12. Communication Breakdown Critical information regularly fails to reach people who need it—not from bad intent, but broken systems.
13. Firefighting Culture More time reacting to urgent issues than building systems to prevent them— our best people are exhausted from it.
14. Role Confusion People duplicate work or miss handoffs because responsibilities and ownership aren't clearly defined across teams.
15. Capacity Delusion Commit to new projects without honestly assessing operational capacity to deliver them well.
16. Data Dysfunction Make critical decisions on gut feel or anecdotes—don't have reliable data systems to inform us.
17. Onboarding Chaos New hires take 3-6 months to become productive (vs. 30-60 days)—no structured onboarding or training.
18. Customer Experience Decay Delivery timelines, response times, or quality degraded vs. 12-18 months ago—hoping customers won't notice.
19. Leadership Admission Gap Leadership team privately acknowledges current pace is unsustainable—but we haven't aligned on what to pause or change.
20. Exit Timing Fear Privately fear we're one or two key resignations from a serious crisis—no plan to prevent or recover.
Scores
SCORES UNDER 20
You're Building Infrastructure Ahead of Growth
You're in the top 5% of scaling companies—infrastructure that supports your team instead of fighting them.
You're Building Infrastructure Ahead of Growth
You're in the top 5% of scaling companies—infrastructure that supports your team instead of fighting them.
What you’re doing right: Clear ownership. Systems that work. Decisions that don’t bottleneck. Your operational discipline is your competitive advantage.
Your challenge: Maintaining this during hypergrowth. Most companies regress when revenue accelerates 30%+ annually. Your discipline is rare—protect it deliberately.
What to do: Your score suggests you’re already doing the hard work. If you want to validate your approach or pressure-test for blind spots, book a diagnostic call. Otherwise, keep doing what’s working.
What happens next
Most CEOs do one of three things:
- Close the browser and revisit it “next quarter” (usually lasts 60-90 days until something breaks and forces the conversation)
- Forward to their leadership team with “thoughts?” (opens dialogue but rarely creates accountability for action)
- Book the call to map the timeline and fixes (uncomfortable because it requires acknowledging the gap—highest success rate because it turns awareness into action)
The third option is uncomfortable because it means admitting you can’t fix this while running the business at the current pace.
But it’s the only one that stops the clock.
Map Your Timeline and Next 90 Days
30 minutes. We’ll map what your score reveals, what’s realistically fixable in what timeframe, and what needs to happen in the next 90 days.
You’ll leave knowing:
- How much runway you actually have before strain becomes crisis
- Which infrastructure gaps are genuine risks vs. manageable growing pains
- What’s fixable in 30 days, 90 days, 6 months—and realistic sequencing
No pitch. No 100-page audit. Just pattern recognition from helping 40+ mid-market companies rebuild operations while maintaining growth—and honest assessment of your timeline.
SCORES 20-38
Healthy Foundation with Predictable Stress Points
You're not broken. You're experiencing normal scaling tension—and you've caught it early enough to fix it efficiently.
Healthy Foundation with Predictable Stress Points
You're not broken. You're experiencing normal scaling tension—and you've caught it early enough to fix it efficiently.
What you’re doing right: Core infrastructure is solid. You’re feeling strain before it becomes a crisis. That awareness is exactly what prevents bigger problems.
What’s happening: Some “temporary” workarounds from 12-18 months ago became permanent. High-performers are rebuilding processes they already fixed once. You’re 90-180 days from this cascading into something significantly harder to repair.
The good news: It’s completely fixable before it gets expensive.
The realistic timeline: Most companies here succeed by picking ONE process failure that frustrates your best people most, fixing it imperfectly but quickly (30-60 days), then using that credibility to address 2-3 deeper infrastructure gaps over the next quarter.
What this looks like: One CEO scored 34: “We had maybe 4-5 months before our best people started looking externally. Fixed our approval bottleneck in 45 days—not perfectly, but it worked. Bought enough trust to tackle the CRM and onboarding systems. Took 4 months total. Two people who were planning exits stayed.”
The window: You have time—but it’s measured in quarters, not years.
The question: Will you address the cracks in the next 90 days—or see what breaks first?
What Your Score Actually Means
This isn’t judgment. It’s a diagnostic that shows you how much time you have.
Every CEO who scores above 35: “How did you know—and how much runway do I actually have?”
We know because these patterns are predictable across mid-market companies:
- Revenue grew faster than infrastructure (by design—you prioritized growth, as you should)
- Promoted people before building systems to support them (normal at your scale)
- Delayed fixes because you were “too busy scaling” (every CEO does this)
- Now paying compound interest on those delays—and the interest rate accelerates with time
The good news: These are known problems with known solutions.
The time-sensitive news: The cost of delay compounds. What’s fixable in 90 days now becomes a 6-month rebuild if you wait another quarter.
The question: Will you fix this in the next 90 days—or see what breaks first?
What Happens Next
Most CEOs do one of three things:
- Close the browser and revisit it “next quarter” (usually lasts 60-90 days until something breaks and forces the conversation)
- Forward to their leadership team with “thoughts?” (opens dialogue but rarely creates accountability for action)
- Book the call to map the timeline and fixes (uncomfortable because it requires acknowledging the gap—highest success rate because it turns awareness into action)
The third option is uncomfortable because it means admitting you can’t fix this while running the business at the current pace.
But it’s the only one that stops the clock.
Map Your Timeline and Next 90 Days
30 minutes. We’ll map what your score reveals, what’s realistically fixable in what timeframe, and what needs to happen in the next 90 days.
You’ll leave knowing:
- How much runway you actually have before strain becomes crisis
- Which infrastructure gaps are genuine risks vs. manageable growing pains
- What’s fixable in 30 days, 90 days, 6 months—and realistic sequencing
No pitch. No 100-page audit. Just pattern recognition from helping 40+ mid-market companies rebuild operations while maintaining growth—and honest assessment of your timeline.
SCORES 39-55
Infrastructure Strain Visible to Your Best People
Your team sees the stress fractures forming. They're not panicking yet—but they're watching to see if you'll address it before it breaks.
Infrastructure Strain Visible to Your Best People
Your team sees the stress fractures forming. They're not panicking yet—but they're watching to see if you'll address it before it breaks.
What you’re doing right: You’ve grown revenue successfully. Your product works. Customers are buying. That foundation is real and valuable.
What’s happening: Operations are 6-12 months behind revenue growth. EBITDA erosion isn’t market volatility—it’s operational inefficiency compounding. High-performers are tired of re-fixing the same failures. Some are starting to measure exit timing.
The timeline reality: You’re 6-9 months from critical failure—either key resignation, customer defection, or operational breakdown that forces board intervention.
Common pattern we see:
- Consultants left decks, not execution
- “Transformation initiatives” stall in planning phases
- Approval processes require 5-7 sign-offs for routine decisions
- More time in “alignment meetings” than actual execution
What this requires: You can’t fix this while running at your current velocity. Most companies here need either:
- Embedded operational help who rebuilds while your team operates (not consultants who audit and leave)
- Internal promotion with real authority to make and enforce decisions
What this looks like: CEO scored 47: “We had about 6 months before losing 2-3 critical people. Brought in a fractional COO for 90 days. Fixed CRM, rebuilt the approval process, and hired an ops manager. EBITDA recovered 5 points in 6 months. The people who were quietly looking? They stopped.”
What happens without intervention: Next 12 months managing attrition instead of growth. You lose 2-3 key people holding institutional knowledge. Then you spend 18 months rebuilding what you could have fixed in 90 days—while also replacing the expertise that walked out.
The window: 6-9 months before something breaks. 90 days to start meaningful repair.
The question: Will you get help while you still have the team and cash to fix this right?
What Your Score Actually Means
This isn’t judgment. It’s a diagnostic that shows you how much time you have.
Every CEO who scores above 35: “How did you know—and how much runway do I actually have?”
We know because these patterns are predictable across mid-market companies:
- Revenue grew faster than infrastructure (by design—you prioritized growth, as you should)
- Promoted people before building systems to support them (normal at your scale)
- Delayed fixes because you were “too busy scaling” (every CEO does this)
- Now paying compound interest on those delays—and the interest rate accelerates with time
The good news: These are known problems with known solutions.
The time-sensitive news: The cost of delay compounds. What’s fixable in 90 days now becomes a 6-month rebuild if you wait another quarter.
The question: Will you fix this in the next 90 days—or see what breaks first?
What Happens Next
Most CEOs do one of three things:
- Close the browser and revisit it “next quarter” (usually lasts 60-90 days until something breaks and forces the conversation)
- Forward to their leadership team with “thoughts?” (opens dialogue but rarely creates accountability for action)
- Book the call to map the timeline and fixes (uncomfortable because it requires acknowledging the gap—highest success rate because it turns awareness into action)
The third option is uncomfortable because it means admitting you can’t fix this while running the business at current pace.
But it’s the only one that stops the clock.
Map Your Timeline and Next 90 Days
30 minutes. We’ll map what your score reveals, what’s realistically fixable in what timeframe, and what needs to happen in the next 90 days.
You’ll leave knowing:
- How much runway you actually have before strain becomes crisis
- Which infrastructure gaps are genuine risks vs. manageable growing pains
- What’s fixable in 30 days, 90 days, 6 months—and realistic sequencing
No pitch. No 100-page audit. Just pattern recognition from helping 40+ mid-market companies rebuild operations while maintaining growth—and honest assessment of your timeline.
SCORES UNDER 20
You're Building Infrastructure Ahead of Growth
You're in the top 5% of scaling companies—infrastructure that supports your team instead of fighting them.
You're Building Infrastructure Ahead of Growth
You're in the top 5% of scaling companies—infrastructure that supports your team instead of fighting them.
What you’re doing right: You built something customers want badly enough to buy despite operational friction. You closed deals. You hired talent. Those are the hard parts most founders never solve. That foundation is valuable.
The reality: Infrastructure hasn’t kept pace with revenue growth—and the gap is now creating material risk.
What’s happening:
- Losing high-performers faster than you can replace them (and losing their institutional knowledge with them)
- “Growth” is funded by burning through operational efficiency reserves that are nearly depleted
- Team stopped believing transformation initiatives—they’ve watched 2-3 die in planning
- Working nights fixing basic errors that shouldn’t exist at your revenue scale
- You privately acknowledge unsustainability—then approve plans requiring it to continue for “just one more quarter”
The timeline reality: You’re 3-6 months from a forcing event—critical resignation, customer escalation, compliance failure, or economic downturn exposing operational fragility. Your board will eventually force intervention. The question is whether you lead that conversation or react to a crisis.
You have two paths:
Path 1: Acknowledge to your board that the infrastructure needs systematic rebuilding. Get 90 days of focused attention on 2-3 critical systems while deliberately pausing new initiatives.
Path 2: Continue current trajectory until something forces the conversation—usually a resignation, customer defection, or financial stress that makes the operational problems undeniable.
Companies that maintain growth and team stability choose Path 1.
What this looks like: CEO scored 61: “We had maybe 90 days before our VP Operations quit—she told me directly. Had an honest board conversation. Hired an embedded consultant, paused two growth initiatives for one quarter. Fixed project management, rebuilt onboarding, automated reporting. Painful 90 days. But we stopped the bleeding. 12 months later, we’re growing again—and our best people aren’t looking at exits anymore.”
What this requires:
- Honest conversation with stakeholders about operational reality (they likely already suspect)
- Embedded help who rebuilds systems while your team operates day-to-day
- 90-day focused sprint on 2-3 critical infrastructure gaps
- Authority to pause non-critical initiatives until infrastructure can support existing commitments
The hardest part: Admitting you scaled revenue faster than systems could support—which many high-growth CEOs do.
The valuable part: You’re not alone. We’ve helped 40+ companies in this exact position rebuild operations while maintaining growth. The ones who addressed it with 3-6 months of runway succeeded. The ones who waited until the crisis had much harder recoveries.
The window: 90-180 days to start meaningful repair before a forcing event.
The question: Will you fix this while you have the cash flow and team to do it systematically?
What Your Score Actually Means
This isn’t judgment. It’s a diagnostic that shows you how much time you have.
Every CEO who scores above 35: “How did you know—and how much runway do I actually have?”
We know because these patterns are predictable across mid-market companies:
- Revenue grew faster than infrastructure (by design—you prioritized growth, as you should)
- Promoted people before building systems to support them (normal at your scale)
- Delayed fixes because you were “too busy scaling” (every CEO does this)
- Now paying compound interest on those delays—and the interest rate accelerates with time
The good news: These are known problems with known solutions.
The time-sensitive news: The cost of delay compounds. What’s fixable in 90 days now becomes a 6-month rebuild if you wait another quarter.
The question: Will you fix this in the next 90 days—or see what breaks first?
What Happens Next
Most CEOs do one of three things:
- Close the browser and revisit it “next quarter” (usually lasts 60-90 days until something breaks and forces the conversation)
- Forward to their leadership team with “thoughts?” (opens dialogue but rarely creates accountability for action)
- Book the call to map the timeline and fixes (uncomfortable because it requires acknowledging the gap—highest success rate because it turns awareness into action)
The third option is uncomfortable because it means admitting you can’t fix this while running the business at current pace.
But it’s the only one that stops the clock.
Map Your Timeline and Next 90 Days
30 minutes. We’ll map what your score reveals, what’s realistically fixable in what timeframe, and what needs to happen in the next 90 days.
You’ll leave knowing:
- How much runway you actually have before strain becomes crisis
- Which infrastructure gaps are genuine risks vs. manageable growing pains
- What’s fixable in 30 days, 90 days, 6 months—and realistic sequencing
No pitch. No 100-page audit. Just pattern recognition from helping 40+ mid-market companies rebuild operations while maintaining growth—and honest assessment of your timeline.
The cause of organizational growing pains
Organizational growing pains can manifest in various ways—
- Employee Overload: Team members feel overworked and disconnected due to rapid expansion.
- Leadership Gaps: Lack of clear direction from leadership as the organization scales.
- Profitability Issues: Revenue grows, but profits decline, indicating inefficiencies in the business structure.
- Infrastructure Lag: The business’s infrastructure isn’t evolving quickly enough to support its growth.
The Road to Sustainable profitability
As you navigate growth, be mindful of these 10 invisible signposts—critical pressure points that could signal potential issues. These signposts can appear in different sequences and at any stage of your business journey and addressing them promptly is key to staying on course.
Meet Jane
ABOUT JANE GENTRY
Jane Gentry has had a successful 30-year career as a CEO, Business Consultant, Executive Coach, and Keynoter. Jane formed her practice in 1999 and since then has partnered with her clients to improve growth, profitability, client retention, employee retention, leadership capabilities and business value.
Jane leverages strategies including the proprietary Value Blueprint to enable business owners and leaders to successfully create healthy organizations, plan for succession or sell their businesses for the highest possible market value. Jane is considered one of the top voices in leadership and sales.
Client Testimonials
Voices of Success: The Jane Gentry Effect
Jimmy Parker
Organizational & Talent Development Architect
From a strategic perspective, Jane has helped our organization think through complex issues and provide an objective view on corporate initiatives. I have observed her keen ability to connect disparate elements to form a cohesive picture when strategizing and working with our executive team . Unlike many consultants who focus on only the organizational or individual level, Jane works well in both areas to deliver amazing results. She not only gave our team valuable advice, but she was also in the trenches with us executing and helping gain enrollment from our teams on initiatives. Jane brings confidence and focus to her work, and I would have no hesitation in recommending her.
Michael Szczachor
SitelogIQ
My team and I had the pleasure of working with Jane over a 6 month period to conceptualize, design and implement a new customer engagement model with the aim of optimizing our go-to-market activities and driving pipeline efficiency and effectiveness. Jane brought a wealth of sales and go-to-market knowledge and experiences to bear as well as offering practical coaching and guidance to our people across multiple functions, career levels and geographies.
Richard ONeil
CEO, PLAE
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Kevin R Roth, DES
Director, Client Service | Czarnowski Collective
Are you looking for a new perspective on your business or department? Would you like a sounding board for your ideas before you implement them? Do you have a problem but need help figuring out who can help you? Jane is your go-to for these items and much, much more.
She supported me with targeted coaching for my team as a whole and individually. My organization and I are now moving faster toward our goals and have a solid strategy for how to reach them.
Matt Devitt, MBA
VP Aftermarket at LDX Solutions
Is your company's Growth Stunted?
AS A LEADER DRIVING GROWTH IN A DYNAMIC COMPANY
You’re achieving growth many only dream of.
Yet, as your company scales, the symptoms of growing pains—inefficiencies, disengagement, and leadership bottlenecks—are becoming impossible to ignore.
Processes are breaking down, communication is getting lost in translation, and the once-clear vision is becoming muddled by the demands of a larger, more complex organization.
If you don’t proactively manage these growing pains, you risk stalling your company’s progress and losing the agility that got you here in the first place.
Is the growth you worked so hard to drive causing more pain than progress?
Your company may be experiencing growing pains
Every organization, regardless of its size or industry, experiences challenges as it grows. These challenges, known as Organizational Growing Pains, are not just minor inconveniences; they are red flags that, if left unaddressed, can hinder your organization’s success and even lead to its decline.
To maintain momentum and ensure sustainable growth, it’s essential to identify and address these growing pains before they escalate.
