Leadership Development: Getting Your Executive Team on Board

By Next Step Partners
Partner, Next Step Partners

It’s a rare executive team that believes so strongly in talent development as a core value that they give HR or Learning & Development carte blanche to create the dream Leadership Development program. About as rare as a Siberian Tiger. If you’ve got one of these elusive executive teams, you don’t need this article, but we’d sure love to meet you.

For all the other HR managers and heads of Learning & Development who need to get the executive team on the bus, we’ve been down this road many times and want to pass along what we’ve learned.

Three Phases of Organizational Readiness

In our work designing custom Leadership Development programs for corporate, non-profit and governmental agencies, we’ve noticed that organizations typically progress through three distinct levels of openness to investing in developing their leaders. And each of these levels calls for different approaches to the executive team.

Level 1 | The Warm Up

Organizations at this phase are just beginning to consider that investing in people could be worthwhile for the organization. There’s often a bit of a scarcity mindset in these organizations, with the senior leaders focusing human and financial capital on things they believe will directly sustain and grow the business. They worry that Leadership Development will be costly and a distraction from the important work at hand.

HR executives at these organizations see Leadership Development as essential to helping the organization succeed particularly as it grows, but have a hard time convincing senior leaders of this. They often try to work around executive team worries by conducting ad hoc (and typically homegrown) programs that don’t require a significant investment. Think manager trainings on time management and feedback. Often these don’t work and can discredit the whole idea of Leadership Development.

The problem for HR is that the limited effect of these types of programs doesn’t make the case for a greater investment in Leadership Development. HR leaders also need to contend with the reality that the organization may just not be ready. But there are ways of planting seeds at this stage to be ready when the time is right

One-on-One Conversations

How can you educate your executive team? Not by writing memos. Instead you need to meet with each of your senior leaders individually and talk with them about where they see the organization going and strategies for getting there. Here are some questions to guide your conversation:

  • What do you think are the biggest challenges facing our organization over next five years?
  • How prepared are our people to lead the organization to that place?
  • What’s our plan for developing succession? If “so-and-so” got hit by a bus, are we going to have people at the ready?
  • How do we retain people who are all about learning?

Experience the Value

Find a way for the executive team to experience the value themselves. For example, identify a leadership topic that will be highly relevant to the challenges facing the team (e.g. difficult conversations, mapping their network and influence, developing a leadership brand, overcoming resistance to change) and invite an expert to run an hour-long program at the next executive retreat or come in for a lunchtime talk. When we do this for clients and prospects, we see people transform from skeptical to curious before the sandwiches are finished.

Pilot Program

Once you’ve laid the groundwork with the executive team, launch a pilot Leadership Development program in one part of the organization that is receptive or with individuals across the organization who you know share your belief in the strategic value of developing talent. You’re seeking both a self-contained investment, but also results that will inspire the executive team to make leadership a higher investment priority.

Level 2 | The Starting Line

Organizations at this phase realize that investing in people can be worthwhile and essential to productivity, retention and succession, and may even have tasked HR with developing a strategy. But top leaders do not yet have clarity on what it will take to create tangible impact. Often leadership development is seen as a silver bullet for addressing a knot of organizational challenges, some of which are structural.

Get Help

If this is the first ever Leadership Development program for your organization, you’ll need to identify the leadership competencies that are particular to your organization and knowing where to start to have the best chance of success. For example, is it most important to focus on succession planning or specific leadership skills? Should you start with the new generation of leaders or the old guard?

If you do partner with a leadership development firm, make sure to pick one that can help guide you to develop a program that will address key executive priorities. Look for a partner with the experience and skills necessary to win over difficult people within your organization. As an HR leader, your focus will be on getting full buy-in and participation from the senior leadership.

Executive Participation

What’s the best way to get executives to have a stake in the program? In our experience, it’s ideal for the executive team to go through the first round of the program. At the very least, they should be involved in selecting the participants and the learning objectives. Throughout the design and roll-out, it’s important to engage in one-on-one conversations with the senior leaders about their vision, and to set expectations about what can be achieved.


To create a program that is seen as effective, you need to build in evaluation from the beginning. If you don’t develop success stories and link them to concrete outcomes with clear value, you may lose the executive team’s support.

It’s also important to focus your program on a few core objectives and skills where you can show impact. A Leadership Development program can’t be a catch all solution to everything that ails the organization.

Invest Enough to Achieve Visible Outcomes

Because you have not yet established a record of success, you may be tempted to accommodate busy schedules and tight budgets and create a program that is too short or tries to accomplish too much with too little. This may be about setting expectations, a point mentioned above.

Level 3 | Hitting a Stride

Organizations at this phase think about talent development as core to the success of the organization and are ready to elevate Leadership Development from a side investment. They have been offering a suite of Leadership Development programs for leaders at different levels, but typically in a modular fashion which means that a lot gets lost as the learning is not enforced in the day to day. It’s time to integrate and scale.

For HR, the challenge is less about convincing the executive team that Leadership Development is needed and more about influencing senior leadership to make Leadership Development a core strategic priority.

Meaningful Evaluation

How are you sure that your Leadership Development investment is getting you what you need? It’s important to revisit the organization’s vision and objectives and evaluate the current programs in this light. It’s likely that you’ll find that you need to make some adjustments to ensure relevance and effectiveness. Go back to find the examples of cases where participation in a program enabled a valuable leader to step up.

You’ll need to include the executive team in the evaluation process and present results alongside a strategic plan for sustaining the learning and creating a culture of learning across the entire organization.

Leadership + Culture

Human Resources is typically focused on individual people, whereas Organizational Development is focused on how to change the culture of a company—and what organization is not facing rapid change? These two parts of the organization often are working separately. But leaders are stewards of the corporate culture; and the new behaviors leaders learn cannot be applied if the culture is not conducive. To take your organization to the next level, Leadership Development and Organizational Development need to work together. This will require new ways of working for both departments and you’ll need executive team support for this collaboration to be successful.

Reference Resources | Books

Regardless of your organization’s level, we recommend the following books to help you make the case for Leadership Development.

For HR leaders who want to sharpen their own influencing skills:

For Executives who want to understand how and when investment in talent development will yield substantial results:




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