Critical Questions for Maximizing New Leader Success

Scott C. Whiteford, Ph.D. Scott C. Whiteford, Ph.D.

Setting new leaders up for success is one of the most critical moments for the long-term viability of an organization. Here, the leader will either create and impact, or struggle to work well with their organization. Unfortunately, in many cases, setting leaders up for success is done poorly. Although leaders are brought into organizations to complete a specific purpose, a multitude of other conditions play into their achievements. Generally, leaders are hired based on their experience and how that experience will translate into their success in the new organization. Although this is an important component of the hiring decision, it should not be the only consideration.

Questions leadership teams must ask when helping a new leader thrive in their organization:

  • What are the expectations?
  • What are the company values?
  • What are the new leader’s strengths and weaknesses?
  • Are they a cultural enhancement?
  • What are their long-term goals?

Most of these questions are not investigated adequately when focusing on how to maximize a new leader contributions.

During the Hiring Process

Forty percent of all leadership transitions fail. In many cases, leaders are hired to reconcile a crisis, and the belief of many organizations is that the person they are hiring has already been a leader, or manager, so they should just put them in and let them go. The critical aspects for setting up a leader for success begin months before they are hired and continues for months after their first day.

Successful steps for new leader outcomes include the following components:

  1. Are the expectations of the role clear to the new leader?
  2. Are they well-versed in the company culture and what makes it unique?
  3. Does the company understand the new leader’s strengths and weaknesses well?
  4. Are they the right cultural alignment and enhancement for the organization?
  5. Does the company understand the long-term goals of the new leader? In many cases, the organization is only clear on the first component and lacks clarity on the remaining, critical points.

1. Expectations

When coaching leaders, we often discuss bringing on new leaders to the organization. I always ask them if they have clear expectations laid out for the new leader. In some cases, the new leader is being added because of company growth. Regardless, if it is due to replacing a leader who has left, or if it is due to company growth, the expectations are rarely clear to the new leader.

In fact, the response is often that they will determine and form the exact position as the leader grows in the organization. This is the first failure in helping leaders achieve outcomes: unclear expectations. Even if both parties agree that the expectations will be decided as the leader grows, they must have regular conversations to help define clear expectations.

2. Company Culture

Understanding company culture is critical to leader success. Of the five main points of this article, this is the one that is the most “laissez-faire” of all of the components. In many respects, little research is done by either party to truly understand company culture before they begin their work. In fact, the extent to the research that is done is through informal conversations with leaders, examining the organization website, and evaluating third-party websites (such as Glassdoor).

This is the second point of failure. Existing leaders ought to set their new colleague up for success by having a very descriptive conversation about the company culture that celebrates the differences and similarities with other organizations. Furthermore, they need to have a structured set of questions they conduct with the potential leader.

3. Strengths and Opportunities

Organizations rarely have an adequate working knowledge of the potential leader’s strengths and weaknesses. Instead, they may ask them what they see as their strengths and weaknesses in an informal interview. Not only does this shed very little light on the potential leader, but in many cases, the existing leaders “lead the witness” by focusing on what they think are important strengths, and basically leading the potential leader down a path where they are bound to answer what they feel is the correct answer.

This is the third point of failure. Organizations ought to use third-party companies, such as Talent Plus, to measure the strengths and weaknesses of each potential leader. By doing so, the organization will know exactly where to focus on when developing the new leader, being sure to keep the focus on leveraging strengths. Furthermore, the leadership team as a whole should complete a strengths and weaknesses assessment to understand how the new leader will work within the existing team.

4. Cultural Enhancements

Does the new leader enhance the culture of the leadership team? That is, can they bring new ideas and new approaches to the team? All while having an aligned set of core values that work well within the existing team?

This is the fourth point of failure. In many cases, the existing leadership team relies on “DYLT” (Do you like them). This usually occurs during the informal interview portion of hiring a new leader. The existing leaders get together after they meet the new leader, and basically ask eachother, “what did you think?”

Once again, a structured process to understanding cultural enhancements is very important. Instead of relying on “gut-feelings,” the leaders should ask standardized structured questions about cultural enhancements during the interview process. Then evaluate the answers independently and meet afterward to debrief. Along with the understanding of strengths and weaknesses, the leader will be in position to have a successful entry onto the team.

5. Long-term Goals

Existing leadership teams must understand the long-term goals of the incoming leaders. This is not the organization’s long-term goals, but the leader’s individual long-term career goals. By understanding their personal vision, the existing leadership can better set them up for success.

This is point of failure number five. Far too often, existing leadership feels the incoming leader should immediately adapt to the organization’s long-term goals. Instead, leadership should focus on how they can adapt their vision to meet the career vision of the incoming leader. I encourage my leaders to engage in a Career Investment Discussion (CID) with the incoming leader (and other leaders on their team). The purpose of the CID is for the leader’s leader to gain a deep understanding of the leader’s career goals. The CID should begin during the first few days of the incoming leader’s employment. By engaging in the long-term goals, they will have a better onboarding process. Optimally, the CID will be completed during the first week and revisited at 90 and 180 days.

Ongoing Success

If leadership addresses these first five points of failure (listed above), they will set the new leader up for success. However, the development continues throughout their career. Specifically, the ongoing development of leaders is critical and extends well beyond their first weeks and months. By the 90-day mark, leaders should continue to execute on the development plan created in conjunction with their leaders.

This article reviews the five points of failure when preparing new leaders for a successful transition into their role:

  1. Ensuring aligned expectations
  2. Understanding of company culture
  3. Completing a structured assessment to know strengths and weaknesses
  4. Bringing cultural enhancements and new ideas
  5. Setting and discussing the new leader’s career goals

By following this guide and implementing a talent-first focus, incoming leaders and leadership teams can put themselves in a better position to find long-term success for the company and the new leader.

Scott C. Whiteford, Ph.D.

Scott C. Whiteford, Ph.D.

Scott C. Whiteford, Ph.D. is the Director of Leadership Analytics at Talent Plus where his role is to partner with, listen to and find solutions for our clients, their teams and organization. With an emphasis on strengths, through selection and development, he helps our clients find success on their Talent-Based Journey.

“I focus on the strength management approach to help grow leaders and improve team and organization cultures.” – Scott Whiteford

Talents: Relationship, Ego Drive, Focus, Conceptualization and Intelligence

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