Have you ever tried something new? Maybe it was a sport or hobby you wanted to take up in your leisure time or perhaps a new computer program or system your organization adopted. Most of the time, when you are new to something, there’s someone – a coach, instructor or trainer – to guide you, in some programmatic, thoughtful and deliberate way. Rarely are you just thrown into it without someone supporting you along the way, right?

In my experience, there’s one example where the answer to that question is a resounding no: Being new to leadership.

It is troubling that those who get promoted into their first formalized leadership position in organizations do not get the time and resources needed to be successful during one of the biggest psychological and emotional shifts we make in our professional lives – going from a hard working employee to a frontline or first-level manager, supervisor or director. A CareerBuilder survey found that 58% of new leaders received no training when they were promoted into their first leadership position. A Zenger Folkman study found it takes 12 years on average for a leader to get any leadership development aimed at helping them be better leaders. That’s a major disservice to those who are new to leadership and want to succeed but are not given the resources necessary to thrive in their new roles.

Some may think that these new frontline leaders should not be the focus of development. But consider this: Entry- and first-level frontline managers – many of whom have never managed before – directly lead the largest number of employees over any other managerial population. They have the biggest direct impact on key performance indicators like customer satisfaction, employee engagement and productivity. Moreover, these new leaders signal the health of the leadership pipeline. Those are significant reasons to reconsider the importance of this leadership population and develop them accordingly.

One efficient and cost-effective way to help new leaders is to get their own bosses involved in their leadership development. Having one’s boss involved in their development introduces and reinforces leadership lessons while maximizing the chances that what is learned will stick with new leadership personnel. Participating in developmental conversations as part of weekly or monthly meetings can also be tied into a new leader’s performance appraisal and formal feedback, which is critical to the work of any boss. This article highlights six evidenced-based topics that bosses of new leaders should coach on and points to consider when having developmental conversations.

A Different Mindset

Bosses should help new leaders move away from what psychologist Carol Dweck calls a “fixed mindset” – avoiding challenges, giving up in difficult situations, and ignoring criticism and negative feedback – to embracing a “growth mindset” where they accept challenges, feedback on shortcomings and failure. Bosses can reinforce that mistakes and failure on the job are part of being a leader, and no one is perfect. They can also create a developmental culture of learning and encourage new leaders to implement what they learned in the future. The conversations bosses have with new leaders should address the following questions:

  • What are you most afraid of in your new role as a leader? What can I do as your boss to lessen those fears?
  • Let me tell you about the mistakes I made when I was new to leadership. What would you have done in my situation?
  • So this situation didn’t quite work out the way you wanted. What did you learn from it, and what are you going to do the next time you are in a similar situation?
  • As a leader, how will you cultivate a growth mindset for you direct reports, so they are not afraid to make mistakes?

A Different Skill Set

New leaders are often promoted because of their technical skill. Continued reliance on those skills will leave them struggling in their leadership role where other skills are key, such as communication and influence. The developmental conversations bosses have with new leaders should address:

  • How often do you like to be communicated with in terms of emails, status updates, meetings and the like? Is it the same as your team members? If not, how will you have to accommodate to make sure you are fitting their needs in terms of the mode, method and timeliness of communication?
  • Think about the people you work with. Do they like to be influenced using logic and data? Are they influenced by values and ethics? How can you become more aware of how people are influenced, and how can you adapt your approach to influence to best fit their preferences?

A Different Work Relationship

One of the biggest challenges for new leaders is understanding that their relationships with their colleagues has changed from peer – and possibly friend – to boss. Bosses of new leaders must have conversations that help new leaders understand their new work relationships, and teach them to navigate the transition from being part of the team to leading the team. Focus these conversations around three fundamental concepts that emerge when effective leadership occurs, according to Center for Creative Leadership research: direction, alignment and commitment.

  • Direction – What is the goal and mission of your team? How has your team been involved in establishing those goals?
  • Alignment – What conversations have you had with team members to understand how each prefers to be managed? Do they know what their exact roles and responsibilities are in fulfilling the goals and mission of the team?
  • Commitment – How have you gone about learning what motivates your team members? Who does public praise work for? Who does private praise work for? If you don’t know, how can you find out? How can you keep each of your team members engaged in their work?

A Different Attitude Toward Work

Many new leaders are unable to stop doing the work, which inevitably gets them in trouble. They fail to understand that they must stop doing the work and start delegating, coaching and developing their direct reports to do the work. Here, bosses can speak with new leaders about the importance of developmental conversations:

  • How do you delegate work? How can you delegate work that challenges others and, if done well, allows them to succeed?
  • How do you feel about feedback?
  • What’s the best piece of feedback you’ve ever received? How timely was it? Was it positive or negative?
  • Could you give me feedback on how I am managing you? That way you can feel comfortable knowing that I can take and implement it for the better. In turn, you will understand that your direct reports need to feel comfortable giving you “upward feedback,” and you can start to instill a climate of open feedback and development for your team.

 A Different Perspective

Having a different perspective means turning one’s attention from the work and toward the many constituencies, stakeholders, departments, functions and all the politics that come with them. Bosses should let new leaders know that politics are a natural part of any organization. It’s not positive; it’s not negative. It’s neutral and part of the everyday circumstances of companies. These conversations should include the following:

  • Tell me what you have noticed about other departments or functions. What are their goals, missions and motivations? How can your team’s goals, missions and motivations fit in with theirs and vice versa?
  • Usually, when things go wrong, it’s because people have an “I win, and you lose” mentality. In the future, how might you promote a win-win mentality when working across departments and functions that still promotes friendly competition?

Emphasizing a Focus

Being genuine, authentic, ethical and of good character shouldn’t be something new. It should be an expected quality of leadership. Bosses of new leaders should emphasize this sentiment in their conversations.

  • Think about leaders in the organization who have thrived because of their authenticity and character. What can be learned from them?
  • Think about leaders who have failed at the organization due to their lack of integrity. What happened, and why did it happen? What lessons can be learned from these failures? 


New leaders often struggle, but their bosses can be a great resource to them. By showing new leaders vulnerability in sharing their struggles, experiences, failures and success, bosses can let new leadership know they are not alone. Take the time needed to have great developmental conversations about the mindset, skill set, relationships, attitude, perspective and focus needed to be the type of boss everyone wants to work for.