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Important Questions to Ask to Ensure a Successful Leadership Program

Published: Sunday, August 21, 2022
Updated: Sunday, August 21, 2022

Every leadership program, whether virtual or in-person, will be more effective when you’re able to answer these questions.

If you're looking to build a leadership development program for the first time (or for the first time in a long time), taking a moment to step back, consider your outcomes, and engage participants managers and teams will make all the difference when creating sustained culture change.

Start by asking these ten questions.

1. What should change as a result of this program?

Don’t start your leadership program until you have a strong vision of what will be different as a result.

What behaviors do you want to shift?

How will that affect your strategic goals?

Don’t stop at “We need better team leaders.” What does that mean? What will they do differently? Get specific.

Work with a training partner who understands your business and who will build a program to get you exactly what you need.

2. How will we include the participant’s leaders?

Leadership programs don't happen in a vacuum.

You’ll need real buy-in from your participants’ managers or you’ll get a minimal return on your investment.

Conceptual support isn’t enough. Managers need insights and specifics about what their people are learning and how they can best support it.

This is even more important when the participant’s managers are not sitting nearby.

Ask for an executive briefing session before the program begins, so leaders understand the ROI, prepare strategic questions for their participants, and have a clear path to support their teams’ learning and application.

Be sure you have the commitment from participants’ managers to give them the time they need to participate fully in the program.

3. How will participants apply what they’ve learned with their teams? No one wants to feel like an experiment as their manager comes back from a leadership program and tries four new ideas without any explanation.

You’ve probably lived through a manager who tried a  new idea.... did it for a week, then forgot about it.

That frustrates the team, and the manager’s credibility suffers.

Does this program include a process for re-entry?

Will your managers get tools to communicate what they’ve learned and to transfer their knowledge?

4. How will we sustain learning over time?


A single half-day workshop doesn’t produce game-changing leaders.

Even if you have a limited budget, find creative ways to build live-online programs that combine learning with practice, reflection, and feedback.

How will this leadership program provide daily and weekly reinforcement of key behaviors?

How will we know what’s working and where managers are struggling?

5. How will this program provoke new ideas and critical thinking to improve our business?

The best leadership training will fire up your managers with new ideas.

Will the program leave them empowered and excited to execute? Or, frustrated about great ideas that “will never happen.”

Work with a leadership development partner who understands your culture and how things get done. The best leadership programs don’t just teach skills. They create chances to apply what they’ve learned to improve the business.

These next five questions are specific
to your live virtual leadership development program.

6. Does the program feature real-time interaction with facilitators and other participants?

There’s no need to settle for a passive, webinar-style training program. It’s too easy for people’s attention to drift as they multi-task.

The best virtual leadership development features live engagement with your facilitators and real-time participant discussions.

7. Does our training partner have experience with live online leadership development?

Online facilitation is different than working in person. It requires different preparation, different ways of engaging participants, and the confidence to work through problems that technology inevitably presents.

Participants know when they’re working with a rookie and will quickly lose interest and engagement. Make sure your leadership development partner has ample experience in training and leading remotely.

8. Can our people take part via video?

Video isn’t the same as being face-to-face, but for virtual leadership training, you’ll want your participants to see one another and the facilitators.

When everyone can see one another, they pay attention and resist the urge to multitask. Plus, it gives facilitators and participants the opportunity to respond to confusion, enthusiasm, and questions.

Make sure your participants can appear on camera and be heard well. 

9. Will our online leadership program leverage technology beyond traditional classrooms?

One of the common mistakes with online meeting technology is to replicate a traditional classroom training environment.

For instance, in a traditional face-to-face program, only one person can speak at a time.

But when you leverage virtual meeting tools, you can have small groups meeting simultaneously and sharing their findings and questions. You can also integrate feedback in real-time via chat and whiteboards, in ways that would lead to chaos in an in-person situation.

Virtual learning also gives you the opportunity to break up your day-long training programs into smaller 60-90 minute sessions over several days or weeks. This gives more time to apply learning in between sessions.

Spaced learning over time with guided application between sessions is ideal for changing behavior. Leverage technology to help your leaders make the most of their training.

10. How will we create the head-space for people to focus on their live online leadership development?

When your manager physically goes to another location for training, it’s obvious that they’re gone.

But with online leadership development, those boundaries can blur. Does their Slack messenger still show them as available? What are the expectations for answering phone calls, emails, and instant messages?

You can create a consistent set of guideline reminders for every session that will help people to focus (eg: turn off your email, social media, office messenger – everything but the one way someone would contact you in an emergency).

Virtual Leadership Training is a great way to bring together managers from different geographies to learn, share best practices, and collaborate on new ideas.

Your turn. What would you add? What important questions do you ask before launching a leadership program?

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