How to Develop Employees Who Actually Grow: 5 Principles Rooted in Clarity, Care, and Reality
You hired someone brilliant. Six months later, they're struggling, and you can't figure out what went wrong. Here's your map for employee development that actually works.
I hired someone I believed in completely.
He was a powerhouse at relationships—the kind of person who could walk into a room and instantly connect with suppliers, vendors, and team members. For the supply chain role I was building, I thought: This is exactly what we need. Anyone can learn the technical parts. But relationship skills? Those are rare.
So I hired him. And then I watched him struggle.
The technical parts of supply chain—inventory management, logistics coordination, data analysis—weren't just challenging for him. They were impossible. I could see it deflating him week after week. The stress. The concern in his eyes during our one-on-ones. The growing tension between us as I kept pushing him toward "best practices" that felt like a foreign language to him.
Eventually, we parted ways. He returned to sales, where his relationship superpowers could actually shine.
And I'm still mad at myself.
Not because he failed. But because I failed him. I didn't assess his actual willingness—or ability—to be trained in the technical skills the role required. Worse, I chose not to see the signals that he wasn't up for the parts that make logistics... well, logistics.
I mistook my belief in him for his readiness to develop in that direction.
If you've ever hired someone with potential and watched the relationship deteriorate as they struggled to grow in the ways the role demanded, you know this pit in your stomach.
Let's make sure it doesn't happen again.
Why Most Employee Development Fails
Most managers approach employee development with good intentions and flawed assumptions. We think:
"They just need more training"
"With enough coaching, anyone can learn this"
"If I believe in them hard enough, they'll figure it out"
But employee development isn't about belief. It's about matching development efforts to actual readiness, capacity, and desire.
Here's what happens when we get it wrong:
Employees feel inadequate instead of supported
Managers get frustrated and the relationship deteriorates
Performance suffers despite everyone's best efforts
Trust erodes as expectations and reality diverge
Good people leave (or worse, stay and underperform)
The solution isn't to stop investing in people. It's to develop with clarity about what's actually possible—and make different choices when reality doesn't match your hopes.
The 5 Principles of Reality-Based Employee Development
Principle 1: Assess Readiness, Not Just Potential
You're in the interview. The candidate lights up when describing how they connect with people. You think: This person has so much potential. We can teach them the rest.
But potential isn't the same as readiness.
The Framework: The Three Rs of Development Readiness
Before investing heavily in someone's development, assess three factors:
Readiness: Do they have the foundational skills to build on?
Receptivity: Are they actually open to being developed in this area?
Realism: Does the timeline for development match the role's demands?
What to assess during hiring (and early tenure):
"Tell me about a time you had to learn a technical skill that didn't come naturally. How did you approach it?"
"What kinds of tasks energize you versus drain you?"
"When have you struggled to learn something? What happened?"
Why this works: You're gathering data on how they learn and what they're willing to struggle through, not just what they're good at today.
Wrong vs. Right:
❌ Wrong: "They're great with people, so I'll just train them on the systems."
✅ Right: "They're great with people. Can they also develop technical competency, or should I structure the role differently?"
Principle 2: Develop Strengths AND Address Critical Gaps (But Know the Difference)
I kept trying to make my supply chain hire fit the traditional mold. I pushed technical training, process documentation, systems fluency—all the things logistics professionals should know.
But I wasn't developing his strengths. I was trying to fill gaps that were never going to close.
The Framework: Strengths vs. Critical Competencies Matrix
Not all skill gaps are created equal. Some are development opportunities. Others are role mismatches.
Strength to Leverage
Give them projects that use this skill; let them shine
Learnable Gap
Provide training, mentorship, practice with feedback
Fundamental Mismatch
Restructure the role OR help them find a better fit
Questions to ask:
Is this skill adjacent to their strengths, or completely unrelated?
Have they shown progress with coaching, or are they stuck?
Does developing this skill energize them or deplete them?
What to say:
"I notice you're struggling with [technical skill]. Help me understand: Is this something you want to get better at, or does it feel like pushing a boulder uphill?"
Why this works: You're inviting honesty instead of assuming they want to be developed in every direction you think they should grow.
Wrong vs. Right:
❌ Wrong: "Everyone in supply chain needs to master data analysis. Keep working on it."
✅ Right: "Data analysis is critical for this role. If that's not where you want to grow, let's talk about what role would fit your strengths."
Principle 3: Create Development Plans That Include Reality Checks
Most development plans are aspirational documents that live in a folder and die quietly.
Why? Because they don't include checkpoints to assess whether the development is actually working.
The Framework: 30-60-90 Development Check-Ins
Don't wait six months to realize someone isn't developing the way you hoped. Build in reality checks.
At 30 days:
"What's working in your development plan?"
"What feels harder than expected?"
"On a scale of 1-10, how confident are you that you can close this gap?"
At 60 days:
"What measurable progress have we seen?"
"What support would help you move faster?"
"Is this still the right development focus, or do we need to pivot?"
At 90 days:
"Has this skill become easier, or does it still feel like a struggle?"
"Do you want to continue developing in this direction?"
"What's the honest assessment: Is this working?"
Why this works: You're creating permission to course-correct before the relationship breaks down and the employee feels like a failure.
What to say:
"I want to check in on how the [development goal] is going. Not to judge—but to make sure we're investing your energy in the right places."
Principle 4: Separate "Can't" from "Won't" (And Respond Differently)
When my supply chain hire kept missing deadlines on technical tasks, I assumed he wasn't trying hard enough. I got frustrated. The relationship deteriorated.
The truth? It wasn't won't. It was can't.
He couldn't process the systems thinking required for logistics. And my frustration made him feel worse, which made his performance worse, which made me more frustrated.
The Framework: Can't vs. Won't Diagnostic
Can't (Capacity Issue):
Consistent effort, limited progress
High stress, visible struggle
Asks for help, tries different approaches
Progress on other tasks
Won't (Motivation Issue):
Inconsistent effort, excuses
Low engagement, avoidance
Doesn't ask for help, resists feedback
Underperformance across the board
If it's "Can't":
Adjust expectations or role scope
Provide different types of support (not just more training)
Have an honest conversation about fit
If it's "Won't":
Address motivation and accountability
Clarify consequences
Explore whether they're in the wrong role or just disengaged
What to say (Can't):
"I see how hard you're working on this, and I notice it's still not clicking. Let's talk about whether this is the right development path or if we need to adjust."
What to say (Won't):
"I'm noticing a pattern where [specific behavior]. Help me understand what's going on. Is this a priority issue, a motivation issue, or something else?"
Why this works: You're diagnosing the real problem instead of applying the wrong solution.
Principle 5: Know When to Pivot (Even If It Feels Like Failure)
The hardest part of employee development isn't starting. It's knowing when to stop.
I kept pushing my supply chain hire toward technical competency long after it was clear the gap wouldn't close. I told myself I was being supportive. Really, I was avoiding the hard conversation.
When we finally parted ways, it wasn't just a relief for him—it was overdue.
The Framework: The Pivot Decision Matrix
Ask yourself these three questions:
Is this person making measurable progress? (Not just trying hard—actually improving)
Is the development energizing them or depleting them? (Check their engagement, not just their effort)
Does the timeline for development match the role's needs? (Can you wait six months for competency, or do you need it now?)
If the answer to any of these is "No," it's time to pivot.
Pivoting doesn't mean firing. It might mean:
Restructuring the role to match their strengths
Moving them to a different team or function
Helping them find a role outside your organization where they'll thrive
What to say:
"I've been reflecting on how things are going, and I don't think this role is setting you up to succeed. That's not a failure on your part—it's a mismatch. Let's talk about what would be a better fit."
Why this works: You're naming reality with compassion instead of dragging out a situation that's not working.
Wrong vs. Right:
❌ Wrong: Keep investing in development that isn't working because you feel guilty
✅ Right: Recognize when further development isn't kind to anyone and make a clear-eyed choice
Essential Do's and Don'ts for Employee Development
✅ Do:
Assess readiness before committing to major development plans
Build in reality checks at 30-60-90 days to course-correct early
Separate capacity from motivation when someone struggles
Develop strengths while being realistic about gaps that won't close
Pivot with compassion when development isn't working
❌ Don't:
Assume potential equals readiness to develop in any direction
Wait six months to realize someone isn't making progress
Mistake effort for results when assessing development success
Keep pushing development that depletes instead of energizes
Avoid hard conversations because pivoting feels like failure
Troubleshooting Common Employee Development Challenges
"I invested so much in their development. How do I know when to stop?"
Look for three signs: (1) No measurable progress despite consistent effort, (2) The work is depleting them instead of energizing them, (3) The timeline doesn't match the role's needs. If all three are true, it's time for an honest conversation about fit.
"They have potential, but they're not meeting expectations. Am I giving up too early?"
Potential matters, but so does readiness. Ask: Are they making incremental progress, or is the gap staying the same? Are they asking for help and applying feedback? If yes, keep investing. If no, reassess.
"How do I have the 'this isn't working' conversation without crushing them?"
Frame it as a mismatch, not a failure: "This role requires [X], and I see you thriving when you're doing [Y]. That's not a deficit—it's data that we might need to find a better fit for your strengths."
"What if they're great at relationships but weak at technical skills—should I just restructure the role?"
It depends. Can the role actually be restructured without compromising what needs to get done? If yes, consider it. If no, help them find a role where their strengths are the primary requirement, not a nice-to-have.
"I feel guilty for not developing them better. How do I let that go?"
You can't develop someone in a direction they're not ready or able to grow. Guilt assumes you had more control than you did. The kindest thing is recognizing the mismatch early and helping them find where they'll succeed.
A Story About What I Should Have Done
If I could go back to that supply chain hire, here's what I'd do differently:
At 30 days, I'd ask: "How is the technical training landing for you? On a scale of 1-10, how confident are you that this is learnable?"
At 60 days, when the struggle was obvious, I'd say: "I see how hard you're working, and I also see this isn't clicking. Let's talk about whether we need to adjust the role or find a better fit for your strengths."
At 90 days, instead of pushing harder, I'd say: "Your relationship skills are exceptional, and this role needs someone who's equally strong on the technical side. That's not a failure—it's a mismatch. Let's figure out what role would let you use your strengths every day."
I wouldn't have avoided the hard conversation. I wouldn't have mistaken my belief in him for his readiness to develop technical competency. And I wouldn't have let the relationship deteriorate while pretending everything was fine.
The lesson? Developing employees isn't about believing harder. It's about seeing clearly, naming reality with compassion, and making choices that set everyone up to succeed.
The Reframe: Development Is an Act of Clarity, Not Just Care
Most managers think employee development is about care—investing in people, believing in their potential, supporting their growth.
And it is.
But it's also about clarity.
Clarity about what's actually possible. Clarity about what the role requires. Clarity about when development is working and when it's not.
The most caring thing you can do is see someone clearly—their strengths, their struggles, their readiness—and make decisions based on reality, not hope.
Because hope without honesty isn't kindness. It's just postponing the inevitable.
Ready to Develop Your Team With Clarity and Confidence?
Developing employees effectively isn't about having all the answers—it's about asking the right questions, building in reality checks, and knowing when to pivot with compassion.
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