Shared Wisdom for Successfully Leading Organizations

Getting ready to become the CEO of a non-profit organization

Gears with success words on them (iStockphoto)

When Franca Gucciardi accepted her first CEO position at the Loran Scholars Foundation she quickly realized the immensity of the task ahead of her and contacted her mentor, Alan Broadbent. What followed was a series of conversations, and a process of learning to ask (and then answer!) the right questions. You’re It! is mentorship in book form, the collected wisdom of two experienced CEOs — a practical and accessible guide to leading an organization. It’s everything you wanted to know about being a CEO but were afraid to ask.

The following is an excerpt from Chapter One, “Making a Move.” To purchase a copy of You’re It!, click here.

Part A. How do you know you are ready to step up?

People have different motivations for wanting to become a CEO.

Some people, after a few years of managing people, simply crave the challenge of increased responsibility for the strategic direction of an organization. For these people, the desire for continuous learning and professional development will push them toward the role of CEO.

Others have a passion for an issue — such as the environment, poverty, or children’s rights — and want to become a CEO so that they can make a greater contribution to the cause that inspires them. In some cases the desire to have a positive influence on a particular issue may have propelled them into a leadership position before they have spent much time thinking about being a leader.

Sometimes individuals are motivated by pure ambition. They want to be the boss. They have a strong entrepreneurial drive and want an organization to move at their speed.

Many people meticulously plan their paths to becoming CEO. For others, the opportunity comes accidentally or much sooner than anticipated; this may be the case if a person’s experience is brought to the attention of an organization that is looking for a new leader. In either situation, you will need to determine if you are ready.

Part B. Self-assessment

A good way to determine your readiness is to critically assess your own skills, both hard (finance, governance) and soft (working with people inside and outside the organization, strategic and business planning). This self-assessment will show the level of competence and experience that you already have, and what areas you need to develop before and during the first few months of taking over as CEO.

Hard-skills inventory:

Financial literacy

Organizations will vary in terms of their accounting-staff support. In fact, the range can be broad, from a member of the board keeping accounts in their spare time, to an elementary staff with a sole bookkeeper, to a competent set of financial staff, to outsourcing of financial management to a professional accounting firm. Regardless of the internal expertise available, a CEO must understand the basics of finance and accounting. Organizations often get in trouble when CEOs don’t treat this area seriously or lack appropriate financial literacy to oversee the finances. This task should not be delegated away completely.

There are five key competencies: records keeping and management; controls and auditing; budgeting and monitoring; reporting; and investment management.

Governance literacy

Governance literacy is the ability to understand the roles and responsibilities of board members versus those of management. The job of the board is not to manage the organization but to provide the oversight that helps in the proper management of the organization. Good governance requires structures and procedures that ensure accountability and encourage strong performance. Good governance also needs processes and policies to be in place for effective decision-making, including clear reporting procedures, written mandates for the board of directors (with term lengths and a process for evaluating director performance), and regular monitoring and evaluation of management’s work.

This is where experience with a board is essential, either as someone who has reported to a board, helped to manage a board’s affairs, or served as a volunteer director on a board committee.

Soft-skills inventory:

Working with people inside and outside the organization

At the end of the day, it is the people you are able to engage who determine the success of an organization. This requires knowing which jobs are key, recruiting the right people to fill the positions, and providing those people with the resources and support they need to succeed. Getting people to work well with each other and to share the responsibility for the success of the organization requires solid relationship-management skills.

Organizations also need to develop effective relationships with the outside world. This means understanding whom to engage, and how and when to create effective partnerships and coalitions. In short, you need to be willing and committed to not only working within your organization but also being the ambassador and link to the outside world.

Delegation is a necessary tool of management. A manager, by definition, cannot do every job in an organization, unless it is an organization of one. So assigning the work to others is necessary.

ALAN: I recall an organization a few years ago where the CEO delegated the finance portfolio to the vice president of finance. Whenever finance was discussed at a board meeting, the CEO turned things over to the VP and never had another word to say about financial matters. The CEO would only resume participation when the agenda had moved on to the next item. It ended badly, when the VP made a number of errors of substance and in reporting that the CEO did not catch. In fact, he could not catch them because he had stopped paying attention to finance. He had moved the finance work off his desk and out of his mind, with unhappy results. It took a board intervention to sort out the problems and ultimately undermined the confidence the CEO had enjoyed up to then.

CEOs don’t need to know every detail of work being delegated, and probably shouldn’t, but they must maintain a basic grasp so they can recognize issues and problems as they arise.

Strategic and business planning

To lead an organization, the CEO must be able to clearly articulate the strategic goals for the organization and know how to divide these strategic goals into business activities. A strong strategic plan assesses the current issues facing the organization and articulates a vision that shows where an organization is going over the next few years. It has measurable outcomes so that success is clearly defined. The accompanying business plan should map out, in detail, the path that the organization needs to take to achieve these strategic goals, as well the resources needed to do so.

Turning ideas into action

The art of “managing” is often described as setting goals, monitoring and reporting results, and managing crises. All of those things are important, it’s true, but at the heart of being a manager is something different: it’s the ability to turn an idea into actual projects or products. Those who have had experience in creating large projects from scratch have specific skills. They know how to break large pieces of work into smaller, discrete chunks. To effectively manage, one must be able to develop and oversee business processes that break work into pieces small enough that they can be completed by individual workers or teams. This not only ensures that work can be completed in a timely and consistent fashion, but it also makes it easier to produce good quality, to measure results, and to ensure that projects are properly resourced.

Part C. Assessing your fit with the organization

Figuring out what type of organization would best be served by your current abilities and interests is a worthwhile exercise. When deciding whether or not to take up an opportunity to lead an organization, the obvious place to start is with the mission. You need to have an affinity with it. A successful leader is one who believes in the organization’s goals, is passionate about advancing the cause, and has the credibility to sell the cause to the outside world.

ALAN: Al Etmanski and Vickie Cammack started the Planned Lifetime Activity Network (PLAN) to help families that had a member living with a disability. PLAN connects the people supporting the person with a disability, including health care providers, educators, and community and institutional workers, as well as other family members, with the goal of providing a more seamless and resilient network of support. From the start Al and Vickie refused to focus on deficits in life but, rather, asked the question “What is a good life?” so that every member of the network could work to provide that for the person at the centre of the network. Al and Vickie kept that mission visible at all times for everyone involved, and this generated successful interventions for people living with disabilities.

Along with the mission, the size and scope of the organization also matter. Is it an organization with five employees or fifty? Does it operate locally or does it have a regional, national, or international mandate?

It used to be that career decisions often made themselves. People worked for the same company most of their lives and advanced through the ranks in an orderly and incremental way, often being tapped on the shoulder when their time for promotion came along. Those days are gone. Most careers involve many different employers and often many different types of work. People move between the private, public, and community sectors, from engineering to finance to management, and from large to small organizations and possibly back again. It is imperative to ensure that your work choices match your talents, desire, and ambition, and to focus on that alignment.

But it is also important to be sure you take into account the needs and interests of the employer. There are many stories of people who have been offered a promotion but turned it down (perhaps it involved moving to another city or leaving a comfort zone), only to find their career path taking a downward, or outward, turn.

The culture of the organization and the stage of development of the organization are also important in determining fit. Is the organization in trouble and in need of major restructuring? If so, the board may be looking for a turnaround leader who will need to assess the problems and quickly create a short-term plan to renew the organization. Turnaround leaders are able to manage and resolve crises, can manage a high level of stress, and are able to inspire confidence. They are efficient and expeditious problem solvers who are comfortable with conflict and adversity, and they often have a thick skin. Turnaround organizations need a higher-than-average level of hands-on management for an intensive amount of time.

Is the organization in its early stages of development or in need of a boost? An organization looking for an entrepreneurial leader needs someone to help generate ideas. The quintessential quality of entrepreneurial leaders is creativity. They consistently see new opportunities that no one else has noticed. They focus on creating value by finding better ways of doing things and with lower costs. They enjoy taking risks — venturing into unknown territory, breaking rules, and going against the status quo.

Is the organization well-established and successful and looking for a steady managerial leader? In this case, the organization will likely have solid structures in place, and it needs someone who is able to promote and advance the organization’s goals within an established vision. Managerial leaders are strong at consensus-building, willing to spend the time necessary to learn about the history and culture of a place, and able to adapt to it. They are relationship-oriented. They make sure they have good people in place with the proper resources. They are able to direct program improvements and quality control, and advance the cause without looking like they are rocking the boat.

Knowing your own skills, strengths, and weaknesses at the outset is therefore extremely important. If your skills are fundamentally entrepreneurial in nature, you probably aren’t going to enjoy a turnaround situation and you might feel stifled at an organization that is already well-established. Conversely, if your style is that of a steady managerial leader, you might want to think twice before stepping on the roller coaster of a recent start-up.

ALAN: When you are thinking about moving up the ladder, be sure you are moving to a job you can succeed at. I have a personal process that I undertake from time to time, every few years at least, where I make four lists: things I am good at; things I am not good at; things I like to do; and things I don’t like to do. For example, I am not interested in details, and I don’t like making cold calls on the telephone. Some of the things I’m good at, like chairing committees, I don’t like very much. When I am faced with an opportunity, I see how it matches up with those lists. The best situation, of course, is matching things you are good at and things that you like. But when you have a job opportunity, it is good to have an analytical framework, even a simple one like mine, to hold it up against as an indication of whether it might be the right job or the wrong job for you.

The four lists

Things I am
Things I
LIKE to do
Things I am
Things I
DON’T LIKE to do


You should also be comfortable with the salary. Often, people taking on their first leadership position will be quite modest with their salary request and accept a salary that is too low. They undervalue their own skills and experiences, and they are so happy to have been picked that they undersell themselves. It is your responsibility to get a strong sense of the organization’s finances and the comparable salary range for the position, and to know if an organization is able to meet your salary expectations. If so, you must make your case to the organization. Your ability to advocate for your own interests in a fair and firm manner is often seen as an indicator of how effectively you will be able to advocate for the organization. In your contract of employment, you should also negotiate the terms of separation with fair terms of notice and severance, in order to make your eventual departure orderly.

Part D. Preparing for the interview process

When you reach the stage of considering leading a specific organization, you need to do your due diligence. You may want to start by undertaking an environmental scan to learn where the organization sits in its competitive environment. Your research should uncover who else is operating in the sector, how the organization is perceived, and what the organization’s strengths and weaknesses are according to the outside world. You should also develop a strong sense of the various stakeholders and key players involved in the organization. Who will have the final say on crucial decisions? To whom does the current CEO listen? Who has special powers outside of their formal role? Who needs to be treated differently? Who are the key donors? Is the founder involved? Within any organization there are people with particular, entrenched interests. A few of these people hold trump cards. The CEO needs to know who holds them and what they are. There may be certain challenges that you think you are up to, but you should be paying careful attention to warning signs that an organization is not healthy or not really interested in hiring the type of CEO you are going to be.

In your preliminary environmental scan and research, you will identify gaps in your knowledge that will form the basis of the questions you will ask in the interview. First-time CEOs tend to be shy in their approach to the interview process, wanting to prove that they can do the job. Interviewing for a CEO position must be a two-way conversation. The organization is interviewing to determine if the candidate is suitable, but as the potential CEO, you must be strategic and use the interview to learn if the organization is one you want to lead.

FRANCA: I was young, I wanted the job, and I thought I knew what the current challenges of the organization were. Instead, in the first few months I spent considerable time discovering a different set of challenges, including an impending deficit that had not been clear to me at the beginning. The problem was that I had not spent enough time during the interview process asking questions. I would not do that again. It’s not that the answers would have discouraged me from taking on the job, but if I had asked better questions, I would have been more clear about what I was taking on.

After the interview(s), there should be no question about the type of leader the organization is looking for, what its current challenges are, what its financial situation is, and what its short- and long-term objectives are. You should ask why the previous CEO is leaving, whether the organization is looking for similar or different traits in their new CEO, and what the reasoning is behind that. Financial clarity is essential. No organization is going to be able to provide a new CEO with perfect financial security and five years’ worth of money in the bank, but a prospective CEO has to know what they would have to work with.


The process of being hired will tell you a lot about the culture of the organization. Are they prepared to answer questions? Are they transparent or are they unable to provide the information you are asking for? Which person(s) will actually be making the hiring decision? Are there clear decision-making processes in place? Do the interviewers present a cohesive vision or do they have different ways of talking about the organization’s mission? Do they have a strong sense of the challenges and opportunities? Is the board looking for a visionary to help set the course or an administrator to facilitate their work? Are they familiar with the organization’s current financial information? Are they willing to share the latest financial statements? If, after a long interview process, you are not getting direct answers to your questions, you might need to rethink if this is the organization for you.

Tips and resources

  1. Build your online profile. LinkedIn, for example, is today’s CV and a go-to resource for hiring managers. Make sure your profile is accurate and up to date. If you are using social media tools such as Twitter or Facebook, make sure the content is consistent with what you would like a potential employer to see and know about you.
  2. Find a reason to say yes. Leaping into your first role as leader is never going to feel comfortable or secure. It is a huge responsibility, and there will always be reasons to say no. Don’t let these stop you from making a positive contribution to your community. If the opportunity is right, step up to the plate.
  3. It is a myth that leaders have to be extroverts. Susan Cain’s Quiet: The Power of Introverts in a World That Can’t Stop Talking (Crown Publishing Group, 2012) is a great book that encourages introverts to take on leadership roles. Introverts make some of the best leaders as they tend to be good listeners. That said, if you are an introvert, you’ll need to figure out how to be situationally extroverted because the role will require it.

To purchase a copy of You’re It!, click here.