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How To Tackle the Perils of Inexperienced Leadership

Updated: Feb 1, 2023

Inexperienced leadership is a common challenge that many nonprofit organizations face - especially in the executive director role.

One of the primary drivers of this is an organization’s financial structure. The Urban Institute found that 67% of registered nonprofits have budgets of $500,000 or less. Because these smaller organizations can only afford a certain salary and since the role may inadvertently hold a lower cache in the eyes of seasoned executives, these organizations often find themselves hiring first time executive directors to fill the leadership position.

We can also attribute this phenomenon to traditional hiring practices. Oftentimes, a new leader is cultivated from within the organization. They might be moving up from a senior level position and stepping into the executive director role. While these leaders have rich experience with the organization, they have not yet worn the mantle of leadership.

Additionally, due to the current shift in the nonprofit sector wherein baby boomers are retiring and younger leaders are stepping up, we are seeing more and more inexperienced leaders taking on the executive director position.

Amplifying the inexperienced executive leadership challenges is the fact that many small organizations have not had professional leadership in the past. Instead, they have relied on the founder or volunteers to lead the organization. The board leadership of these organizations has never experienced hiring and partnering with an executive director and this can lead to confusion and an unsupportive environment.

We see from data that inexperience and lack of support can result in significant disillusionment on the part of the executive director. In one of our recent surveys with executive directors who had left their former positions, we found that:

  • 51% left the role within 4 years

  • 60% did not take another executive director role once they left

  • 45% left the nonprofit sector completely

One bad experience as an executive director can cause a talented individual with potential for growth to leave the nonprofit sector. It can also negatively impact an individual’s self confidence and motivation in the future.

What’s more, a high turnover of executive directors can quickly turn a healthy nonprofit into an unhealthy - or even unsustainable - organization. It can result in board members or junior staff members leaving their roles, can have a direct impact on constituents who experience unreliable services, and can even derail the mission and finances of the organization.

So, who are these inexperienced leaders? And what challenges result in them leaving their positions?

A Closer Look at Inexperienced Leaders

Inexperienced leaders in nonprofit executive director roles may not have years of managerial or executive decision-making experience, yet they are oftentimes highly motivated and self-driven individuals with significant potential to grow and excel. They are energized by the opportunity to:

  • Shape and see impact on a mission

  • Set and drive action towards a vision

  • Sharpen their leadership skills

  • Identify and solve challenges

  • Shape and guide a team of staff and volunteers

As part of my ongoing Storied Awareness interview work, I spoke with prior executive directors who explained what drew them to the role in the first place. Here are a few examples:

“I was passionate about the organization and the role allowed me to mold a vision and mission into reality.”

-Respondent 1

“It was rewarding to raise resources for a mission I believed in. . . I learned a lot and felt I made a difference.”

-Respondent 2

“Every day was different and the opportunity to build an organization was both exciting and challenging.”

-Respondent 3

A clear through line emerges when reading these quotes: all of these leaders were attracted to the idea of finding fulfillment in their work through their ability to make an impact, and be of service to others.

With so much excitement and ambition, what exactly are the roadblocks that inexperienced executive directors are challenged with?

Challenge 1: Isolation and Lack of Support

A feeling of being isolated and unsupported by the board chair, board of directors and staff members is one of the most common and persistent challenges inexperienced leaders face. Many new executive directors are quite surprised to feel that they are shouldering their role and the direction of the organization alone. As one Storied Awareness survey respondent stated,

You can't even really have a bad day because everyone's looking to you.”

But, executive directors can combat this feeling of isolation through a few tactics.

Tip 1: Set up biweekly one-on-one meetings with your board chair

As executive director, your partner-in-change is your board chair. The importance of having a healthy working relationship with your board chair cannot be overstated. The person in this role helps you lay the framework for a strong organizational culture. They serve as the liaison to the rest of the board, and can be integral in facilitating productive contributions from board members. They also can be a source of creative friction for you, helping to develop innovative ideas that will push the mission of your organization to fruition.

My advice is to start holding biweekly one-on-one meetings with your board chair to begin cultivating a trusting relationship. Ideally, these meetings will either have a loose agenda or none at all. The goal is to find time to talk, share in your experiences, and catch up on any major personal or professional updates. These can be in person when protocols permit, yet they can also be conducted effectively through phone or Zoom calls.

By making time to curate a relationship with your board chair, you’re demonstrating your interest in learning about the other person’s perspective, establishing consistency and showing your respect for one another.

In conversation, you might learn valuable insights from your board chair about the history of the organization, the relationships between other board and / or staff members, and understanding of how you can be a better leader.

And importantly, you’re creating a space where you can talk to them about challenges that arise in your own role.

Tip 2: Create Your Own Structure

Another way to feel more comfortable and confident as an inexperienced leader is to create structure for yourself. If you’re feeling isolated and unsupported by others in your organization, you can cultivate habits and practices that provide a sense of stability on a daily basis.

An impactful way to do this is to block your time on a weekly basis, and try your best to stick to your schedule. By creating a schedule outline each day, you give yourself time to touch all of the most important aspects of your role and keep yourself accountable for following through on projects that are short-term and long-term. Schedule blocking is also an effective way to ensure that meetings don’t overwhelm your entire day, and that you still have time to do critical work on a daily basis.

See this schedule as an example:

  • Monday, Wednesday and Friday: meetings, internal and external relationship building, and community engagement

  • Tuesday and Thursday: long-term projects and strategic work

Tip 3: Start positive habits with staff

One major element of feeling isolated and unsupported at work is a disparate relationship between you and your staff. While it may not always be possible to have a close working relationship with every staff member, there are things you can do as a leader to cultivate positive group bonding experiences.

I recommend bringing in organizational habits from your prior workplaces that you know were a success and which made you feel more connected to your workplace. You might try:

  • Starting a Monday morning, staff-wide email chain that encourages staff members to praise one another’s successes

  • Having a monthly staff update meeting, followed by a one-hour lunch where socialization is the focus

  • Instituting monthly volunteer half-days, in which the entire staff gets together to volunteer for a local cause. Let staff members submit suggestions for where to volunteer, and be sure to select one of the options they submitted.

By implementing these staff bonding experiences, you can have an opportunity to see staff members in a positive light and get to know them on a more conversational level. Small, consistent efforts like these will help you form long-term relationships at work, and even give you something to look forward to.

Challenge 2: Overwhelming Demands of the Role

Through Storied Awareness surveys, many nonprofit executive directors expressed the pressure they felt to flawlessly manage their board and staff, serve their constituents, execute the mission of the organization, and meet financial goals - all while remaining confident and professional. Over time, this takes a toll on any leader. And it can even make a role feel unsustainable. One respondent noted,

“It always was, just let me get through these two weeks, let me remind

myself to eat.”

I’m sure this sentiment will resonate with many of you reading this!

Many new executive directors don’t feel comfortable asking their board chair, board of directors, or other senior staff members for help for fear that doing so will underscore their own inexperience. They might also be uncertain how to best ask for help if they haven’t had much experience managing others.

The good news is that leaders can take control of feeling overwhelmed with these tactics:

Tip 1: Get comfortable with delegating

Learning how to delegate tasks - and what to delegate - is a critical skill that makes for a successful leader. Yet, it’s oftentimes one of the biggest challenges that inexperienced leaders face when they are new to a role.

The first step in delegating tasks successfully is to make a list of your own strengths and challenges, by answering questions such as:

  • What do you know you excel at?

  • What tasks are you excited to take on?

  • What activities have you struggled with in the past?

  • What activities leave you feeling drained of energy?

The challenges you identify in this exercise that are not critical to your job are the first tasks that you can consider delegating to others. For example, perhaps you don’t need to approve social media posts or proofread every newsletter. There are other staff members who specialize in those areas, who can and should be taking ownership of those tasks. If you are concerned about the quality of their work it is a management concern and you can use your time to address this issue, not taking on their work.

If one of your main challenges is a critical component of your job, you should consider bringing someone else in to work on a task with you in partnership. Say, for example, nonprofit financial management isn’t your strong suit. But, your head of programs loves working with finances and wants to learn more. If they have the extra bandwidth in their schedule, they would make a great person to assist you with financial management while also keeping you accountable for the task getting done.

Many nonprofits have a lean staff bench that can make delegating even more difficult. If this is the case, two of your greatest resources are volunteers and board members. Think creatively about how you can excite and engage these individuals to take on tasks that full-time staff members cannot. Oftentimes, this strategy starts with relationship building. Take time to get to know your volunteers and board members, and find out what excites them. Then, you can strategize how to use their interests to support the greater work of your organization.

Ultimately, you should consistently ask yourself this question: As an executive director what is the work that only I can do?

Tip 2: Set priorities and stick to them

In conjunction with the importance of setting a schedule for yourself, setting priorities for your work and the organization as a whole is a critical practice. Doing so will help you remain focused, feel more satisfied with meeting your goals, and help you keep your eye on the mission of the organization.

First, I recommend setting priorities for your own work. Think through these questions:

  • What do you think are the most important goals that you can help your organization accomplish within the next year?

  • What are the top 3 most important functions of your role?

  • What are the 3 biggest challenges facing your organization?

  • What are the top 3 things you should be doing weekly to be a successful executive director?

One of the most important aspects of staying accountable to your priorities is having buy-in from your board and staff. To do so, I recommend having a meeting with each of these groups where you explain what your priorities are for your role and the organization, and where you will primarily be spending your time on a weekly and monthly basis. Allow your board and staff to give you feedback on this so that you can adjust your priorities accordingly.

Challenge 3: Navigating Board and Staff Relationships

I hear again and again from nonprofit leaders that navigating the diverse personal dynamics of their organization is a significant source of stress. And executive directors’ experiences can be complicated by the fact that they are at the center of staff relationships, board dynamics, and the organization’s interactions with volunteers.

Ultimately, managing relationships is a key component to feeling satisfied in the role. While finding a healthy place in staff and board relationships may be a challenge, I’m confident that many executive directors can achieve this in time.

Tip 1: Understand your board dynamics and adjust accordingly

Getting buy-in from the board of directors is oftentimes a challenge for inexperienced leaders. Many are surprised to find that boards can vary dramatically among organizations. Being unprepared to work with a certain group dynamic can exacerbate existing challenges that a leader faces. As the Harvard Business Review notes, there are 5 types of boards:

  1. The Passive Board- The board’s activity and participation are minimal and at the CEO’s discretion.

  2. The Certifying Board- The board certifies management tactics and supervises an orderly succession.

  3. The Engaged Board- The board serves as the CEO’s partner. It provides insight, advice, and support on key decisions.

  4. The Intervening Board- The board becomes deeply involved in making key decisions about the company and holds frequent, intense meetings.

  5. The Operating Board- This is the deepest level of ongoing board involvement. The board makes key decisions that management then implements. This model is common in early-stage start-ups.

I encourage executive directors to identify which type of board they are working with. It might even be a blend of these options. Doing so will help you gain a better understanding of the dynamic you’re working with, and how you need to adjust your board management efforts and other priorities accordingly.

For example, an isolated executive director may feel frustrated that they have a “passive” board of directors. They might want more input on various major decisions at the organization. In the short term, direct outreach to specific board members might be useful. Be sure to have a specific question or set of questions and give them a way to feel positive about their engagement with the work. You could look to provide more training on governance and how to proactively engage with the organization for the board members. You could also engage your board in a one-day workshop that addresses specific challenges such as shared vision setting. Long term, given the priorities of the organization you should also consider what type of members you want to encourage to be considered for board seats.

Alternatively, an overwhelmed executive director may feel frustrated by an “intervening” board that micromanages all of their decisions and derails the big-picture goals of the organization. In this case, you can work with your board chair to set expectations that each meeting will focus on specific and critical topics selected ahead of each meeting and that other topics will be shelved for later. Board training on the roles and responsibilities of board members, as well as a retreat to set priorities for the work ahead as an organization, can provide a framework for you to work within. Additionally, improving and practicing your facilitation skills can help you navigate meetings with intervening board members.

2. Consider how you can adapt your behavior.

Another impactful way for executive directors to navigate interpersonal relationships is to consider what they can do on their own to improve the dynamic. The executive director has significant influence on the culture of an organization, and can proactively create a positive environment just through their own actions. Some suggestions include:

  • Do not engage in workplace gossip about others

  • Make an effort to recognize and celebrate the successes of your board, board chair and staff

  • Be an active listener when speaking with others; make an effort to remember and recognize their opinions and suggestions in the future

Finally, and most importantly, I suggest that all leaders practice patience - with themselves and others. Practicing flexibility and acknowledging that everyone makes mistakes is essential to navigating interpersonal dynamics effectively, and finding happiness in your work relationships.

Becoming Better Leaders

While the challenges that an inexperienced leader and executive director face can be significant, they should rest assured that there are concrete steps that they can take to find support, confidence and satisfaction in their roles.

If you enjoyed this post, join my newsletter for more insights, stories and actions for ambitious nonprofit leaders. And in the meantime, keep up with me on LinkedIn!


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