Avoiding Mistakes: Tips for CEOs to Stay on Top

How do you become a CEO? How do you keep the board happy? Dive into these insights and more.

By Jed R. Mandel


Remember that old joke, the one about two rules for getting along with the boss? “Rule one: The boss is always right. Rule two: If in doubt, see rule one.” Well, association CEOs probably like those rules. But, even the best need to always strive to make sure that those rules correctly apply to them — that is, that the boss is, indeed, always right. So, here are a few tips for staying on top.  

Getting to be a CEO

  • Don’t accept a job offer without due diligence. Look at the financials, past minutes, organizational documents, publicly available material and the like. And ask around, discreetly. Know what you are getting into.
  • If there are things that you need and want, get them before you accept the job (and, where possible, get them in writing). Most CEOs are pretty good about getting an upfront agreement on compensation-related terms, but they aren’t always as thorough about “authority” issues. What is the scope of the CEO’s authority? Can they hire and fire the staff? Can they sign checks … and contracts? Be sure to get what is important to you clarified before you start the job.
  • The corollary to the above is to avoid the perception of being a “nickel and dimer.” There are certain things that CEOs don’t need to get upfront because they aren’t that big of a deal, and the CEO essentially controls the decision on what happens. A classic example: A CEO candidate lost out on a job by making the office’s vacation and health benefits policies an issue in their employment agreement. Both are important, but as CEO they probably could have made the relatively minor changes that they wanted from the inside — if they hadn’t lost the job upfront.

Staying a CEO

  • CEOs must follow the organization’s bylaws, policies and procedures. There is no easier way to lose one’s job than by not following the rules.
  • Remember, it’s the board that makes, interprets, and enforces the rules. Abide by their decisions. Real-world examples of where a CEO fought with their board and won are few and far between. That doesn’t mean that CEOs can’t disagree with their boards, or that boards are infallible; it only means that there are right and wrong ways about pushing, pulling and steering your board in the right direction.
  • If you make a mistake, disclose it, own up to it and address it. Lots of people make mistakes (probably even CEOs). And, making a mistake doesn’t necessarily result in losing one’s job. But, no one helps themselves by trying to cover up a mistake. Even if you don’t make the (second) mistake of covering up, be sure to minimize the first mistake by disclosure. It is much easier to resolve something that you have identified and explained in your own terms than to be put on the defensive by having to respond to how someone else has framed the problem.

Succeeding as a CEO

  • CEOs must pay attention to what’s going on: in the industry or profession they represent, among the organization’s membership, within the organization, among the staff, etc. CEOs can’t “manage” what they don’t know.
  • CEOs should delegate and avoid micromanaging. But, they should never fail to supervise. The buck stops with the CEO. They ultimately are responsible, not the person to whom a matter is delegated.
  • Understand the wants, needs and desires of your leadership — their opinion counts a lot — and strive to meet them. That can mean doing the big stuff, like helping the president look good and allowing them to take credit. And it can mean the little touches like remembering a birthday or ordering the right food for the board lunch. Whatever their particular interests, most of them have egos, and it really isn’t that hard to stroke, stroke, stroke.
  • Act like a CEO. Look the part; talk the part. Actors are always reminded: There are no small parts, only small actors. Same thing for CEOs. Among other things, that means that to be successful, a CEO must be willing — and able — to do whatever job has to be done.
  • Be a leader. That’s fairly well understood when it comes to interactions with the CEO’s subordinates. But CEOs also must provide leadership to the board. Boards must be told and shown what must be done and how things should be done. The trick is for the CEO to be willing and able to do so and, most important of all, capable of doing so in such a way that the board thinks it’s all their idea.

Being compensated as a CEO

  • Don’t be afraid to tell your leadership what you’re worth. Be willing to ask for what you want. Be prepared to defend it. And, be willing to compromise, without getting into a funk because you didn’t get what you asked for.
  • It’s pretty easy to negotiate a small annual raise. Making a significant compensation jump requires planning: when, where, how and with whom. Think ahead. Just because your contract term is up doesn’t mean that is the only or best time to ask for a raise. The most successful CEOs look far ahead and determine when the association’s key leadership will include those individuals who are most inclined to make a favorable decision with respect to compensation (or any contract issue for that matter). And, then, those CEOs carefully work to get all of the ducks in a row to make it happen.
  • Make sure the board knows and appreciates that association management is a profession and an expertise. Not everyone can do it. All of the skills, experience, knowledge, demands, stress and the like required to be a CEO more than justifies the CEO’s expected (high) level of compensation. The fact that people on the board (and in the membership) make way more or way less is irrelevant. The CEO should be paid what they are worth as CEO.
  • Plan for your future. Establish (and periodically review and revise) career goals. Knowing where you are, in life and in your career, will substantially help you focus on what you need. That need may be as nuanced as deferred compensation (or more vacation or a sabbatical) over a bigger salary. Or, it could be a new job with new challenges and greater opportunities.
  • In planning for the future, plan to fail and plan for the unexpected. It is not prudent to think that you won’t get fired; that your association (and your job) won’t be merged out of existence; that the whole organization (or the industry or profession it represents) can’t have a catastrophic financial decline; that you won’t get sick or injured. Planning to fail means that you need to have a plan in the event that your board turns against you (because, sometimes, it only takes one). Planning for the unexpected means having the protections in place for you and your family. But you’re a CEO — that means you also must have plans in place to protect your organization. Yes, succession planning is your job, too.

Avoiding criticism as a CEO

  • Don’t allow the board to get involved in issues for which they shouldn’t interfere. The CEO, not the board, should be involved in hiring, firing, discipline, etc.
  • Don’t overzealously try to stop the board from looking at something because they don’t need to know, it’s not within their authority, or it’s your responsibility. Remember, if it comes down to a fight, the board wins.
  • Don’t take action without authorization.
  • Don’t let your leadership be surprised — disclose, disclose, disclose.
  • Know when to seek help and advice — from leaders, employees, peers, legal counsel, etc. — and be willing to accept it.
  • Protect the organization’s reputation and integrity.

About the Author

This Law Review web exclusive was written by Jed R. Mandel, founding member of Chicago Law Partners, LLC. CLP serves as the Association Forum’s general counsel.

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