Leadership Development Strategy: What to Decide Before You Buy

A leadership development strategy is a company’s decision to build more leaders on purpose, tied to where the business needs to be in three years. You commit to developing leaders first, start with the CEO, give the whole team one language of leadership, and combine training, facilitation, and coaching so the change sticks.

Most founders I talk with skip all of that and go straight to buying a program. I’ve talked with over 1,200 leaders of fast-growing companies on my podcast, and here’s what I’d decide before you spend a dollar.

What is a Leadership Development Strategy?

I’ve heard the same answer in hundreds of conversations with CEOs. Ask about their leadership development, and they point to a course they bought, a book everyone read, or a workshop from last spring.

That’s a purchase. Your leadership development strategy answers a bigger question. How will your company build the leaders its next three years require?

A training program is one possible answer to the “how” part. The strategy comes first, and it decides whether any program you buy is the right one.

What if the program was never the problem? What if you never decided what it was for?

I tell CEOs this all the time. “Leaders create leaders. Managers get work done.” Read that again.

Your company can be full of good managers, hit this quarter’s numbers, and still stall, because nobody below the founder is growing the next layer of people. You see it, right?

I’ve said it to founders more times than I can count. “I really think that buying a leadership program is a commitment.” Buying one “shouldn’t be a check-the-box kind of thing.” The strategy is how you make sure it isn’t.

Why Do Check-the-Box Leadership Programs Fail?

Check-the-box offerings feel good. A book of the month club or a low-cost online course library gives everyone something to point to, and the budget line looks responsible.

I call it the “perk nobody uses.” Everyone gets access, a few people log in, and a couple of months later nothing about how your managers lead has changed.

Those offerings rarely touch how leadership shows up on a Tuesday afternoon, when a manager has to hand off a decision or have a tough conversation. Books and courses can support a strategy, but they aren’t the strategy.

Here’s why they stall:

• ●Nobody committed to them, so they become a perk nobody uses.
• ●They teach people about leadership without practice in real work.
• ●They run on one format, and adults rarely change from one format alone.
• ●They got picked because a peer company bought the same thing.

That last one is more common than you’d think. Founders copy what their peers are doing, and plenty of those peers are doing it poorly. I’ve watched it happen over and over.

When a CEO asks me where to look instead, my answer is the same every time. “They might need to look outside their industries and their peer groups to find what’s really working and find a program that offers multimodalities of learning for adults.”

Make Five Decisions Before You Buy a Program

Here’s the order I walk CEOs through. Each decision sets up the next one, so skipping a step usually means coming back to it later (and usually at a worse time).

Everything else rests on this decision. “They need to commit to the idea of developing leaders first.”

I know how that commitment feels from the buyer’s side. When I wrote my first big check to a coach of my own, I had knots in my stomach, and the breakthrough started the day I signed, well before our first session.

The commitment costs money that could go to marketing, product, or a new hire. You’ll also pull time from people who already feel stretched, and I won’t pretend otherwise. “That investment is probably going to be a little bit of a sacrifice.”

Without the commitment, you get the “perk nobody uses.” With it, people show up, the CEO protects the calendar, and leaders practice between sessions.

Are you willing to protect this when the quarter gets busy?

Who should go first, the CEO, the managers, or everyone at once? My answer is the CEO, every time. Your managers watch how you lead, and they’ll copy that long before they copy anything from a workshop.

I learned that one the hard way. In my ticket business, I was the firefighter pulled into every problem of the day, and every fire I put out taught my team to hand me the next one.

Once you have the trust and the tools, extend the work to the next class of leaders: your managers, directors, and VPs. They learn the language you’re already using, so a conversation about accountability means the same thing in every department.

What about everyone at once? I’d rarely do it. A whole-company rollout on day one spreads attention thin, and your people end up waiting to see whether the CEO changes first.

“Our flow is really kind of start slow and build into it, and I think that’s a good way to select a program.” If your managers are next in line, here’s what goes into a manager development program that sticks.

Your managers already proved they can do the work. A leadership development strategy builds the skills that grow other people, so the company has decision-makers below the founder.

People lump work skills and leadership skills together all the time. Work skills are how well someone does the job, and leadership skills are how well they grow the people who do it.

Want a closer look at each one? Start with our guide to the leadership skills managers need.

For most teams, tough conversations are the weakest of the five. Is that true on yours?

Adults learn through more than one format, so a strategy built on one format leaves most of the change on the table. I think of it as three parts of learning, and you need all three.

You’ve heard “leaders at every level” a hundred times. But does your budget pay for all three parts, or only the cheapest one?

Research backs the mix. A 2017 meta-analysis of leadership training covering 335 independent samples found the strongest programs used several delivery methods (practice above all), spaced sessions over time, and face-to-face delivery instead of self-administered courses.

SHRM describes the widely used 70-20-10 model the same way. In that model, about 70 percent of leadership learning comes from on-the-job experience, 20 percent from people such as mentors and coaches, and 10 percent from formal courses. In other words, the classroom is the smallest slice.

Here’s where the common methods fit:

At Core Elevation, our Leadership On-Ramp exists for exactly this work, creating more leaders and closing the skill gap between your executives and your managers. Saint Hung, CEO of Universal Processing, has said his sales management team’s time in the Leadership On-Ramp lined up with a 34.3 percent growth year. You can see more about our approach to leadership development for growing companies.

Years ago, I answered a simple question about where I wanted my business to be in three years. I hit about 90 percent of it in two, and that’s when I realized I hadn’t thought big enough.

Your growth plan deserves the same honesty. Here’s the line I come back to most: “A 3-year growth plan requires people to be leaders, people to make decisions, define new strategies and innovations.”

Pull out your plan and read it as a list of leadership demands. Every goal in it assumes someone below you can carry it for you.

Build those leaders on purpose, starting now. A plan that depends on leaders you haven’t developed yet is a hope, and hope isn’t a strategy.

Learn From a Junior Executive Team That Grew Into Its Role

One of our clients had a very junior executive team. They were young, none had been an executive before, and most had little experience even as managers.

They were still asked to lead departments, solve problems, be proactive, and find new strategies. Their basic leadership skills weren’t there yet.

Here’s what we did together:

• ●Saw the gaps. Each leader, along with the CEO, looked at which specific skills were missing.
• ●Built the right skills. The work focused on empowering their people to make decisions, accountability, coaching, and communication, especially tough conversations.
• ●Worked as one team. We worked with the entire executive team and the CEO together, so everyone learned the same language.

Over one to two years, they became a strong team. They had ups and downs as every team does, and we guided them through those cycles.

The company committed to developing the whole team in one language, starting with the CEO. That leadership foundation is what carried their growth plan.

The CEO and that young team did the hard work, and they get the credit. We were there to guide them.

How Should You Evaluate Leadership Development Providers?

Talk to at least two or three programs before you choose. Would you hire a VP after one interview? Then don’t pick a leadership partner after one sales call.

Watch for these red flags:

• ●One workshop or offsite sold as the whole answer
• ●A content library pitched as leadership development
• ●No real role for the CEO
• ●No clear way to show what changes in how people lead

Ask your peers what they use, then look past your industry and peer group too. Some of the best answers come from companies that look nothing like yours.

What Does Waiting Another Year Cost You?

You might be thinking now isn’t the time, that you’ll get to leadership development after this quarter’s push. I’ve heard that line from plenty of CEOs, and the pull is real. But the cost of waiting builds quietly, long before it shows up in a report.

If you put leadership development off for 12 months, things will look normal at first. Work still gets done.

Then things get a little harder. You’ll notice it in small ways:

• ●More alignment issues between departments
• ●Less proactive communication from your managers
• ●Tough conversations that keep getting pushed to next week
• ●Managers who control and micromanage their way to the goal

That last one hides the problem, since the numbers still come in. Over time, the company stagnates because, without leaders creating leaders, it can’t scale past 30, 40, 50, or 100 employees without real strain.

The pressure lands on your managers first. Gallup’s State of the Global Workplace 2026 found manager engagement fell from 27 percent to 22 percent between 2024 and 2025, and lower manager engagement drove most of the global decline.

That matters for your whole company, since Gallup estimates managers explain at least 70 percent of why engagement rises or falls across teams. A 3-year plan built on managers who only manage work is a plan you can’t execute.

How Will You Know the Strategy is Working?

Skip the course completion rates. Watch how leadership shows up in the business instead:

• ●Decisions get made below you, and fewer problems land on your desk.
• ●Managers hold their own people accountable instead of escalating.
• ●Tough conversations happen earlier, before a problem becomes a crisis.
• ●Leaders use the same language across departments.
• ●Your managers start developing the people below them.
• ●Leaders bring you new strategies instead of waiting for yours.

How many of those can you check off today?

Gallup also gives you a benchmark for what good can look like. In best-practice organizations, 79 percent of managers were engaged in 2025, nearly four times the global average.

Expect ups and downs along the way. The five stages of developing leaders show what changes at each level as the work takes hold.

Frequently Asked Questions

Founders and people leaders bring these up with me constantly, so here are short answers.

Commit First, Then Start Slow

I opened by saying most founders skip straight to buying a program. The ones who build real leadership teams commit first, start with themselves, and bring their leaders into one language.

So here’s your next step. Give it fifteen minutes and a pen today. Take your 3-year plan, circle every goal that depends on someone below you making decisions, and write the name of the person who’d carry each one.

Then look at those names.

Who are you building to carry that plan?

Are they ready today? If they aren’t, what’s the first decision you’ll make this week?

Lead with courage.