How to create a successful leadership development program

Back in April, we hosted our Leadership Development Fair. And oh my, were there some big learnings! Throughout the week, we explored 9 unique real-world case studies and topped things off with a roundtable for our fellows to distill our thoughts.

We discussed the Good, the Bad, and the Ugly of leadership development, debunked common myths, and came away with some hot new takes. That’s all thanks to our incredible guest speakers: Bin Sou, Antonia Onaca, Aditi Patil, Chris Wong, Anne Marie DeCarolis, Saad Qureshi, Sara Hoxhaj, Catalina Veneziano, and Shaheen. 💜

Now we’ve had time to dig into our findings and gather our conclusions, and it wouldn’t be right not to share them with our peers.

Here are the highlights.

Embrace research before designing leadership development programs

Rolling out leadership development programs without proper research is a bit like diving into a puddle headfirst. Not a great idea.

But what would happen if you dipped your toe into that puddle first? You’d probably realize it’s a little shallow to dive into and adjust your plan. You know, like find a deeper body of water.

Here’s what we learned about deep research for leadership development initiatives.

Look at diverse quantitative & qualitative sources

Unless you’re ok with just hitting and hoping (see the puddle analogy above), your best bet for building successful leadership development is to gather reliable quantitative and qualitative data.

Let’s start with the more “mainstream” research methods you’ll want to try:

  • Run surveys with people managers and individual contributors to understand the current state of leadership and identify areas for improvement
  • Conduct empathy interviews (around 8-10 is a good number) to really get into the pains and hopes of leaders
  • Hold focus groups at strategic milestones throughout the program development process to get that essential qualitative data
  • Comb your current organizational data for trends, progress, and potential strategy ideas
  • Research external case studies to discover best practices (and the DON’Ts) from other organizations’ programs

We’ll throw in a couple of curve balls later.

Look for leaders' challenges beyond skill gaps

News flash. Leadership development isn’t just about closing skill gaps. Like everyone else, people managers go back to their day-to-day jobs and find many blockers in applying their learning. These blockers include:

  • Processes that need to be fixed
  • Technology that needs to be optimized for better efficiency
  • People your leaders need to be connected to

As a result, as L&D professionals, we should look beyond workshops and traditional learning programs to find ways to remove blockers for leaders. This is more recently called leadership enablement.

Design with leaders in mind

Leadership development is only effective if you design it with actual leaders in mind. This may seem like an obvious statement, but it’s one that many learning designers tend to forget during the process.

Here are some of our big learnings about designing leader-centric experiences.

People are people everywhere. Don’t fall & get stuck in the “leadership skills framework” pit

As L&D professionals, we’ve traditionally placed a big focus on developing leadership skills. And they’re definitely important. But sometimes, this can distract us from our true purpose: supporting people in becoming effective leaders. The same applies to frameworks: it’s easy to get sucked in.

Frameworks are important, there’s no doubt about it. But, we often get too caught up in the idea of a bespoke framework. For example, as L&D professionals, we might be inactive when it comes to supporting leaders until we find the perfect combination of skills our leaders should have. We talk internally, look externally, or hire consultants - all to design this “magical” framework.

The thing is, leaders are leaders everywhere. They all deal with people. So chances are that the skills required to be a great leader are the same everywhere. Sometimes we just need to find a framework backed by research and just use that one - for example, Google’s project Oxygen.

It’s not always necessary to spend time, money, and resources coming up with a framework. Most of the time, we can just follow tried-and-tested models rather than reinventing the wheel. Or at least not let the research for the perfect skill combination stopping us from actually acting.

Invite your leaders to the co-creation table of your leadership development programs

It really does take a village to build an effective leadership development program. And it’s certainly not something you should do in a vacuum.

A really exciting approach is to host a Hackathon to co-create the entire initiative with your people managers. Working together will give you access to innovative ideas and solutions right from the horse’s mouth.

Added bonus? Getting your people managers involved in the ideation process means they’re less likely to criticize or reject initiatives if they helped to build them.💡

We saw a really great success story during the Leadership Development Fair from Wipfli.

Aditi Patil, Talent and Organizational Development at Wipfli, shared how she used design thinking principles to lead a hackathon for the Wipfli leadership experience. Thanks to the initiative, the team went from a blank slate to a ready-to-launch prototype.

Embrace the enablement mindset in your design process

When we move away from the “a leadership skills framework is all we need” mindset, we leave more space to explore the idea of leadership enablement. And more importantly, how we can incorporate this mindset into the learning design process.

The leadership enablement mindset looks at the big picture. Doing this well means developing a wider perspective on the challenges leaders face and how we address them in our learning initiatives.

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This goes beyond skills development. Instead, it’s more of a four-part puzzle that includes skill acquisition, optimizing people processes, providing the right tools, and nurturing relationships.

When we factor all this into the design process, we build programs that truly prepare individuals to be leaders (our true purpose).

Disclaimer: Every leader is different. Maybe your leaders simply need skills development, or maybe not. The only real way to find this out is through thorough research data, this will indicate whether you should lean into a development or enablement approach.

Design your leaders' journey to identify critical moments

One of the major pieces of the puzzle is understanding what our leaders go through. From the moment we onboard them and as they settle and grow into their role.

That’s why it’s so important to create your leadership journey.

Your first step is taking an in-depth look at your leaders’ journey and identifying key moments. What kind of support do leaders need during these moments? How will you provide it?

It’s a good idea to start with onboarding. Think about the challenges they face. The more you understand this, the more empathy you can build as you design initiatives.

For example, new people managers often struggle with delegating, moving from an individual contributor to a leader, establishing boundaries, and handling unfamiliar processes. The list goes on. But the more you understand the challenges at each critical moment of their journey, the easier it is to design effective learning solutions.

Get all this good stuff down on a roadmap and use it as a framework for your leaders’ development progress. 🧭

Balance social activities with individual ones, and demanding activities with lower-energy activities

The last thing you want is for your leaders to switch off or burn out during the development program. That’s why striking the right balance of activities throughout the learning experience design process is so crucial.

You can break activities down into four categories:

  • High energy + individual activities - eg. asking leaders to be mentors or asking them to create shadowing programs
  • High energy + social activities - eg. inviting leaders to team coaching sessions or asking them to facilitate workshops
  • Low energy + individual activities - eg. nudging them to read learning materials or listen to podcasts
  • Low energy + social activities - eg. inviting leaders to workshops or external leadership talks

A great program incorporates a healthy mix of activities from each category, always with the mindset of “fewer and better.” Put another way, design so your people managers get the best experience possible. ⚡

Design with diversity in mind

Your people managers are diverse. They come from diverse backgrounds, they have diverse abilities, and they have diverse ways of approaching things. Your learning experiences should reflect this.

An example is seniority. Not all leaders have the same level of experience, both in the organization and as a people manager. That means they’re likely to need different levels of support from us.

So how can you address this during the design process? What can you do when you’ve got senior leaders who have seen it all?

We saw a really interesting example during the Leadership Development Fair.

Antonia Onaca is a Diagnostician and Solutionist for Leadership Enablement at Miro. She walked us through 3 initiatives she designed to support senior leaders in a meaningful way (not just asking them to attend “another, just more expensive” program).

Importantly, she shares her tactics for getting less than enthusiastic leaders involved in the process (spoiler: by proactively finding opportunities to help them and reassuring them that the program can benefit them).

Another important consideration during the program design process is neurodiversity.

Incorporating design thinking can help us gain more empathy toward leaders and understand their needs. On a deeper level, it can also support us in shaping leader personas.

That’s what Shaheen, the Leadership and Learning Lead at Hireup, did.

She shared her firsthand experience of how Hireup used leader personas to drive targeted leadership development.

The team created different types of personas, including:

  • Role-based
  • Goal-directed
  • Engaging
  • Fictional

This exercise allowed them to make smart design choices based on what these different personas needed, creating distinct learning tracks for people managers. With an overall satisfaction score of 4.7, this was a successful initiative for Shaheen and the team.

Think of the implementation of your leadership development program from different angles

There are so many moving parts when designing and implementing leadership development programs. That makes it easy to develop tunnel vision and forget about the peripheries.

A big reminder from the Leadership Development Fair was to take a step back and think about the implementation process from different angles and perspectives. Let’s get into this in more detail.

Automate your recurrent, manual activities

Those little manual learning management tasks may start off small. Upload a resource here, enroll a learner there…

But soon enough, these repetitive manual activities start adding up and stealing large chunks of your day. That’s a killer for productivity and also totally unnecessary.

The answer is designing your leadership program with this in mind. Think about sustainability. Then think about automation.

Your LMS has plenty of automation features to help you streamline manual tasks like:

  • Enrollments
  • Deadline reminders
  • Reporting
  • Certification

You can take this as far as you need to. The main lesson is that automation should be an integral part of your design plan.

Drop the mindset “build it and they will come”. Embrace talking about the challenges, not your solutions

L&D professionals wear a lot of hats. And one of those hats should be marketing. For your leadership initiatives to take off, you’ll need to learn marketing principles and apply them to your communication strategy.

The better you can market your programs, the more likely your people managers are to participate enthusiastically.

The first step is to rethink how you communicate learning solutions. As L&Ds, we’re so used to telling our leaders how amazing this program or that program is and why they should join. But, there’s a better way to catch people’s attention.

A better angle is to talk about the challenges your learning initiative is solving. Examples include:

  • You struggle with delegation
  • Your team’s engagement is dropping fast
  • Retention rates in your team are dropping

This will increase how relatable your messages are, and the chances that your leaders will pay attention.

Don’t make changes for the sake of change and if your “customers” don’t signal you should

We all know the saying, “If it ain’t broke, don’t fix it”. I think this definitely applies to learning initiatives and leadership development.

Research should lead every update or change you make to your current program. Because without that, you’re just hitting and hoping.

So if you have been tasked with improving your current leadership program, start with the big questions. Why do you want to update it? What isn’t working? How do you know it isn’t working? Do you have data to back up this hypothesis? What’s the goal of this project?

Until you have concrete answers to those questions, don’t jump in and start changing things “just because”. Your gut may be right, and you make the initiative better. Or you could be wrong and end up wasting time and resources on something that wasn’t broken to begin with.

Look out for the signals from your audience (a drop in performance, low program attendance, mixed learner feedback).

Measure, measure, measure your leadership development program

Measurement should never (ever) be an afterthought. It should be one of the first things you think about when you design any L&D initiative.

But what should you measure? And how should you measure KPIs?

Here are some ideas I picked up during the Leadership Development Fair.

Set diverse KPIs (ideally together with your leaders)

In an ideal world, we’d measure every learning KPI under the sun. Unfortunately, the reality is that most L&D teams don’t have the resources to do that.

A more realistic approach is to prioritize metrics that have a high impact and require low effort. Then, once you have those sorted, you can think about what else to measure.

Of course, you need to know what you want to achieve before you can set relevant metrics. This is where you should sit down with your stakeholders to agree on the KPIs your initiative should impact.

Aiming for diverse KPIs gives you a broader sense of how learning initiatives are performing and where weak areas lie.

Don’t forget to analyze benchmarks

Once your KPIs are clear, your next step is to analyze the current state of things. This benchmarking will give you a clear idea of your progress during and after your initiative.

But you shouldn’t stop there.

If you’ve got the resources, A/B testing your audience can give you some even deeper, juicier insights into the impact of your program. To do this, you will split your target audience into two random groups. One of the groups would receive the initiative, while the other one would not. Then, you’ll compare results.

Finally, you’ll use the data you gather from the experiment to refine your initiative and determine where you need to iterate.

After your initiative is rolling, your data gathering should continue. This time, you’ll focus on collecting data to compare it against your KPIs' initial status. Do you see signs of progress?

This is good to know, but it’s definitely not black and white. Just because your KPIs improve doesn’t mean your initiative was the catalyst. That’s why it’s vital to isolate the effects of your intervention by listing anything that could have affected the change.

Finally, subtract all of those from the improvement you noted. Whatever’s left is how your program actually contributed to the end result.

Empower leaders with data

The best gift you can give your leaders is data. It gives them a clear picture of the state of things and empowers them to drive action and make informed decisions.

We saw a great example of this during the Leadership Development Fair.

In the case study below, we learned how Printify used self-assessments to drive leaders’ awareness and growth. Bin Sou, a Learning and Development Specialist at Printify, led the charge on this initiative.

Starting from the leadership values of the company, Bin Sou created an assessment for Printify’s leaders. The purpose was to measure self-awareness and the frequency of desirable leadership behaviors.

Bin broke the process down into 3 stages: Preparation (8 weeks), Showtime (2 weeks), and Results (4 weeks).

In total, he identified 12 behavior-focused questions related to 4 core values. These were Tension, Credible, Descriptive, and Encounter. In total, an impressive 109 managers and their teams participated, which is around 87%.

More interestingly, 68% acted on the results and made changes based on the data.

Share your results with whomever needs to know

We all want to share results when they’re positive. But communicating the not-so-positive results is just as important. Why? Because your stakeholders need to see the whole picture and understand that you think critically about your initiatives. It also gives them proper insight into what works and what doesn’t in L&D.

As we saw in the Printify case study, providing data can be a catalyst for action.


I hope you’ve enjoyed reading what I learned during the leadership development fair. Even if you don’t agree with everything, these events are such a great space to break out of your current thinking patterns and see how others work.

Let us know your thoughts.

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