Critical Conversations for New Leaders

Leaders who are new to a leadership role, new to the company, or recently promoted to a role of greater scope or complexity face significant challenges. Research shows that roughly 50% of newly hired executives quit or are fired within their first three years, and up to 40% of executives who change jobs or are promoted fail during their first 18 months.

To help ensure a greater probability of new leader success, the typical executive selection process places a premium on the demonstrated ability to get things done and the projected ability to make an immediate impact. While these are clearly positive attributes, an overreliance on an executive's perceived natural ability to succeed often overshadows the reality that organizations are complex systems. Effective acclimation takes focus and deliberate attention.

One of the most important yet most often overlooked components of effective onboarding is the need to quickly gain focus and alignment with three important constituent groups - your boss, direct reports, and key stakeholders.

Engaging in critical conversations with each of these important constituents will help accelerate the acclimation process by providing insight into the culture, expectations of the role, and team dynamics.  These conversations provide an efficient and effective mechanism for gaining insight into the unique and important nuances of situations and relationships.  In addition, the exchange provides a foundation for clarifying and aligning your needs and expectations with the needs and expectations of your boss, your team, and your key stakeholders.

Critical Conversation: Ensuring Alignment with Your BossCritical Conversations for New Leaders

When assuming a new role or joining a new team, it is important to create a solid foundation for success by clarifying expectations with your new boss.  Essential areas of exploration and discussion include explicit and implicit expectations as well as communication preferences. 

In addition, these early conversations provide insight into cultural norms and organizational context that provide clarity into not only what needs to get done but also how things get accomplished in this environment.  Important components of the critical conversation to ensure alignment with your boss include:

Discuss mutual expectations

  • What are top priorities for the first 90 days?

  • From your boss’s perspective, what does the new leader’s “success” look like?  How will “success” be measured?

  • From your view, what does “success” look like?  What do you need from your boss to help you get there?

  • What frequency and type of communication does the boss prefer?  What do you prefer?

  • How often will the new leader and boss meet 1:1 in the first 90 days?  What are the main topics these meetings will cover? 

  • Are there any pet peeves or “hot buttons” that you think the other person should be aware of? 

Role Clarity

  • Confirm the formal structure of the company, your new boss’ areas of responsibility, and the leadership team structure.

  • Clarify any immediate questions about which tasks belong to you, which to the boss, which somewhere else?

  • Which decisions are yours, the boss’s, or shared between the two?

  • What types of decisions require approval, consulting, and/or are subject to veto?

  • Who else is significantly involved in decision making?

Cultural Awareness

  • As a new leader, what do I need to understand about the company’s decision processes and how decisions get made?

  • What are the current “hot issues” that I should know about?  Where can I go to learn more, and/or gain greater perspective?  (add to your stakeholder map)

  • What do I need to be aware of or watch out for as I am learning the organization?

  • Are there particular things that I need to do to avoid making a faux pas in this company’s culture?


Critical Conversation: Engaging with your Direct Reports

As a leader, most of what you accomplish will get done with, and through, other people.  Gaining an understanding of the perspectives, ideas, and concerns of your new direct reports provides insight into the current state of the team and may highlight potential opportunities for increasing individual and team effectiveness.  Important components of the conversation with direct reports include:

Understanding the Individual: 

  • How does each individual describe themselves personally?

  • What are they passionate about?  What does each find important about the work they do? 

  • What do they think you most need to understand about them? 

  • What strengths does each individual bring to his/her role?  What challenges?

Understanding the Roles:

  • What is each individual’s formal role and areas of responsibility?  How long have they been in the organization and in this role

  • Clarify any immediate questions about scope of their role and responsibilities.

  • What are the major priorities or ‘hot issues” in this individual’s area?  What is he/she striving to accomplish this year?

  • Clarify expectations about your involvement in these priorities and issues.  How active will you be?  What kind of information updates on these issues do you (as boss) expect?

Mutual Expectations: 

  • Define decision making parameters:  Given each direct report’s role, what types of decisions are assumed to be “theirs” to make, the new leader’s to make, or shared between the two? 

  • What frequency and type of communication do you prefer?  Each direct report? (e.g., voice mail, email, in-person)

  • How often will the new leader & each direct meet 1:1 in the first 90 days?  What are the main topics that these meeting will cover? 

  • Are there any pet peeves or “hot buttons” that you think the other person should be aware of? \

Critical Conversation: Engaging Key Stakeholders

Organizations are complex systems.  Roles, resources, and workflow from one group or function are often connected and reliant on the work product of other groups or functions.  Work flow is also often interconnected in informal (or less obvious) but no less important ways with other key stakeholders.  Your ability to achieve success is enhanced by increasing your awareness and focus on collaborating and leveraging this network of resources, stakeholders, and influencers. 

Draw a stakeholder map of key teams, functions, and people that you will interface with, both within the organization and externally, so you can establish a sense of how your role and your team fits within the broader system.  With input from your boss (and others), define a strategy, priority, and timing for outreach and conversation with each stakeholder contact.  Determine who you need to connect with in the first 30 days, 60 days, and 90 days. 

For each stakeholder, identify a strategy to get acquainted, begin building relationships, and understand:

  • What does each stakeholder needs/expect from me and my team?

  • What will I likely need and expect from them?

  • What are their perceptions about the potential challenges and opportunities?

  • Are there issues and concerns that need to be addressed? 

Taking the time to fully engage your boss, your team, and your key stakeholders in these critical conversations will help you better navigate the organization and identify the broader context and expectations of the new role or new responsibilities.  Focusing on immersion and understanding before jumping into implementation and execution increases the opportunity to identify and deliver “early wins” that help both you and organization see success in the critical first months and beyond.


Career Partners International provides top quality talent management services to organizations of all sizes. Their offices around the world help assessengagedevelop, and transition talent in any industry. To find out more about Career Partners International and how you can maximize your organizational performance, reach out to an office near you or contact us today!

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