How to Measure Leadership Development and Prove It Worked

How do you measure leadership development? Measure the gap people can see once they understand the skill. The score they give themselves on day one is a guess, and usually a generous one.

Then watch what changes: decisions made below the founder, tough conversations happening, and the founder’s time moving to higher-value work. After more than 1,200 podcast interviews with fast-growth CEOs and leaders, let me show you how to measure leadership development in a company of 30 to 100 people.

Why Are Pre-Assessments So Often Wrong?

Across hundreds of coaching conversations, day one of a leadership program goes about the same way. I hand out a short assessment and ask people to rate themselves from 1 to 10 on empowering others, holding people accountable, coaching, and having tough conversations, and the 7s and 8s come flooding back.

Then the training starts. People find out what those skills really involve, and you can watch the confidence drain out of the room.

Here’s how I put it: “Most people overestimate those skills of coaching others or empowering others, and having hard conversations.”

I call that first number “the day-one guess.” Nobody is lying to you. They’re grading themselves against a picture of the skill they don’t have yet.

Researchers have a name for the pattern: response-shift bias. Your yardstick changes once you learn what good looks like, so a simple before-and-after comparison on the same self-rating can hide real growth.

You don’t have to take my word for it. In a study of an interdisciplinary leadership training program published in the Maternal and Child Health Journal, 34 trainees across three cohorts rated themselves at the start, then looked back at the end and rated where they had started. Their original ratings came in significantly higher than their looking-back ratings in all 24 leadership areas measured.

If your managers rated themselves an 8 on coaching today, would you believe them?

Keep the pre-assessment. Just stop treating the day-one guess as the baseline truth.

What Should You Measure in Leadership Development?

You’ve heard “what gets measured gets managed” a hundred times. But are you measuring the right things?

Here are the five measures I use, and each one has its own moment.

The Leadership On-Ramp is the program we use to grow more leaders below the founder and close the skill gap between executives and managers. I mention it here because the timing of the post-assessment depends on it.

Let me pry two words apart before we go further. Training is something people attend. Development is something your team can see in the decisions, the conversations, and the calendar.

You might be thinking you don’t have the time or the HR team to measure any of this. You don’t need software either. A spreadsheet, a calendar, and honest coaching notes carry most of the load, and they fit the way our leadership development work runs inside growing companies.

What Should a Post-Assessment Capture?

The post-assessment is where the real picture shows up. Run it after the formal phase of the program, once people know what empowerment, accountability, coaching, and tough conversations look like in practice.

Ask each person to rate two things on the same scale: where they were before the program and where they are now. Here’s how a participant might describe the gap.

“What I was doing before was literally a 2 out of 10. What I’m doing now is a 7 out of 10.”

Read that again. On day one, that same person might well have called themselves a 6 or a 7.

What if the lower “before” score is the good news? In other words, the person finally sees the skill clearly enough to grade it.

Five points of honest movement tells you far more than a one-point bump between two guesses. As I like to say, “That gap is more meaningful because they can reflect on that poor confidence.”

A 2023 study in BMJ Leader points the same way. Seventeen healthcare professionals went through an eight-month leadership program, and the looking-back ratings picked up significant change on 11 of 12 questionnaire items, against 4 of 12 for the standard before-and-after comparison.

The authors still suggest running both when you can. I agree, so keep the day-one rating on file and let the post-assessment do the heavy lifting.

A good post-assessment asks for evidence alongside every rating.

If you want to go deeper on the skills themselves, I’ve written about the core leadership skills for managers in a separate guide.

How Do You Measure Confidence and Team Readiness?

Confidence is part of the measurement, and most programs skip it. A manager who knows how to have a tough conversation but has zero confidence in it will still find a reason to put it off.

Track confidence by skill on a simple 1 to 10 scale, and revisit it in every coaching session. Expect setbacks. A hard conversation goes sideways, confidence drops, and the coach’s job is to keep moving it back up.

“You also want to have a coach that is having dialogue with them and probing into these areas to move from 7 to 8, to 8 to 9, and so on.”

A confidence log can be as plain as this:

• ●The skill (for example, holding a peer accountable)
• ●Today’s confidence rating from 1 to 10
• ●What happened since the last session
• ●What moved the number, up or down
• ●The next situation where they’ll practice

Team readiness is the other half. Gallup’s numbers make the point. Across business units, at least 70 percent of the gap in engagement ties back to the manager, so whatever readiness your managers have, or lack, shows up in their teams.

To gauge readiness, ask a few plain questions about each manager:

• ●Could this person run the team for two weeks while you’re away?
• ●Do their people bring solutions, or only problems?
• ●Who on their team could step into their seat in a year?

Which of your managers would pass that test today?

What Behaviors Show a Leadership Program Worked?

Scores tell you what people believe about themselves. Behavior tells you what changed in the business.

In the months after the program, I watch for three things.

The first one matters most to a founder. If decisions still pile up on your desk, the program hasn’t changed how your company runs yet, whatever the scores say.

The second one is where most managers stall, and I get why. Tough conversations feel risky, so people wait. If that’s the sticking point, start with my guide on how to have tough conversations at work.

The third one is the quiet sign of a real leader. Managers who coach grow the people around them, which is the heart of developing your managers into leaders.

How Do You Measure the Change in a Founder’s Time?

For founders, track where the time goes. Moving up the 5 Levels of Leadership is a measurable shift, and your calendar is the scoreboard.

There’s a fifth level above these. For measuring founder time, the movement that matters most runs from Level 2 up to Level 4.

I know Level 2 from the inside. For most of the nine years I ran my ticket business, my days ran on color-coded lists and spreadsheets, and when something broke, I jumped in myself, every time.

My back still remembers those years of a phone wedged on my shoulder. I wasn’t a CEO. I was a firefighter with a nice title.

The $10 Million CEO Who Lived in Spreadsheets

The CEO of a $10 million company once asked me what other CEOs do with their time. So I turned it around and asked about his.

He said, “Well, to be honest, I spend a lot of my time doing spreadsheets and email.”

He meant accounts receivable, cash flow, organizing email, and responding all day. That’s how he felt he added value, and he was stuck at Level 2.

The shift came when he accepted that other people could manage the spreadsheets and organize the information. His job was to use those tools to make decisions.

Within three months, a junior team member took over the day-to-day upkeep. He moved through Level 3 to Level 4, and today he spends most of his time in executive leadership team meetings, coaching conversations, visiting his offices, and focusing on top-tier clients.

He did the hard part. He let go.

Run a Quarterly Calendar Audit

Here’s how to measure the same shift in your own week. Grab a pen and paper and give yourself 20 minutes.

1. 1Pull your calendar and sent emails for the last two weeks.
2. 2Tag each block of time with a level from the table above.
3. 3Add up the hours and work out the share at each level.
4. 4Pick one Level 2 task to hand to someone else this quarter.
5. 5Repeat the audit next quarter and compare the shares.

The number you want moving is the share of hours at Levels 3 and 4. If handing off the work is the sticking point, start with one task you do every single week.

Build a Simple Leadership Development Scorecard

Put the measures in one place, so you’re looking at the same view every quarter. Here’s a scorecard with ten indicators you can run from a spreadsheet.

Keep the team survey about specific behaviors. People rate what they’ve seen far more reliably than they rate a fuzzy trait like “leadership presence.”

Where Does the Kirkpatrick Model Fit?

The Kirkpatrick model is the best-known way to evaluate training, and many of the pages ranking for this topic are built around it. Its four levels are reaction, learning, behavior, and results.

I don’t lead with it, and you don’t have to either. Still, it maps cleanly onto the measures you already have.

Financial return is its own question. You’ll find it much easier to answer once these people measures are in place.

What Should You Stop Counting?

Here’s the cost of skipping real measurement. Companies lean on day-one self-ratings that are inflated, and they can’t tell whether the investment changed anything.

Programs get judged by attendance and completion. Meanwhile, the founder keeps spending time on work others could own.

Stop treating these as proof that leaders developed:

• ●Completion rates. Finishing a program tells you people showed up.
• ●Satisfaction surveys. A high rating tells you people enjoyed the sessions.
• ●Attendance. Being in the room is the entry ticket, and growth happens after.
• ●Day-one self-ratings as the baseline. As you’ve seen, they run high.

A single workshop can open someone’s eyes. Measurable change in how a leader behaves takes practice, coaching, and time.

Frequently Asked Questions

These are the measurement questions that come up most when I talk with founders and people leaders.

Measure the Gap, Then Watch the Calendar

I started with the day-one guess. Now you know why that number can’t carry the weight, and what can: the re-rated gap, confidence by skill, the behaviors in the months after, and the hours on the founder’s calendar.

Before you close this tab, try one thing. Take ten minutes (pen and paper beats a screen here), pull up last week’s calendar, tag every block with a level, and see where your time really went.

Be honest with yourself. Where do you think most of those hours will land?

What would change if half of those hours moved up a level?

Ready to see what your leaders’ growth really looks like?

Don’t get me wrong. Measuring this doesn’t require hiring me.

Lead with courage.