Surprise parties can be fun. If the balloon tower featuring your age got cancelled—even better.

Surprises in business aren’t so welcome. When the membership director springs a dashboard on you with every indicator trending south, it’s not a good day.

Distraction is an invitation for the unexpected. If you’re playing Whack a Mole with details, it’s easy to overlook the big picture. Take a breath. Step away from operations and spend time exploring your organization on a macro level. You will discover strategies that can help eliminate micro issues and expand your association’s capacity.

Joseph Knecht, CEO and Managing Director of, made this observation about his leadership perspective.

“The company can only be successful if all legs of the business are strong—finance, sales, development, and client relations. If any area is out of balance, it’s a threat to the organization. My role is to be what Gino Wickman calls a visionary. I’m responsible for aligning the elements that are needed to see the future. It’s those strategic, big picture issues that tee us up for success.”

Paying attention to the future is critical for CEOs who want to succeed in digital markets. Technology is a shell game that keeps even prescient leaders guessing. But it’s important to have an idea where you think the ball might go.

Even if you recently completed a planning process; in fact, especially if new initiatives are on the table, these are wide-lens questions you can consider to meet future goals more easily and avoid unpleasant surprises.

Are You Structured for Success?

How many rubber stamps are required to launch a new initiative? When the answer is too many, it’s time to begin rethinking how your board, committees, and staff get work done. The digital marketplace has no patience for lengthy decision-making.

How many rubber stamps are required to launch an initiative?

Kevin Ordonez, .orgSource President and Managing Director of Digital Strategy, offers this advice. “The current association governance structure is out of step with an environment characterized by instability. New business models are an inevitability that associations must be prepared to explore.”

Boards and committees have the important job of providing the members’ perspective. It’s a skill that only they can deliver. Putting members in roles they aren’t trained to execute, like marketing or meeting planning, isn’t an efficient use of their talent. When volunteers and staff stick to what each group does best, solving problems and making decisions becomes easier.

Accept the Challenge

Structural changes can be challenging, but there are significant rewards for the effort. Sharon Rice, .orgSource Managing Director of Business strategy, made these comments about helping the California IT in Education Association (CITE) board to transition to a more strategic role. “During a retreat, the board discussed various governance models and how they could shift perspective to maximize CITE’s potential,” Sharon recalls. “We also explored their relationship with the staff and how it might evolve. To provide specific guidance, I attended the board meeting and presented an evaluation along with recommendations for how the group could lead more effectively.”

“Working with Sharon, we were able to create a governance plan that aligned perfectly with our life cycle stage,” Andrea Bennett, CITE’s Executive Director, notes. “We had a road map for how to advance the organization and prepare for the next phase of growth.”

Are Talent and Technology Aligned?

With volunteers and staff correctly focused, review your goals and determine whether you have the right talent and tools to meet them.

Recently, a colleague confided that every item on her organization’s strategic plan involved technology, but the association didn’t have the systems or the expertise to develop any of those initiatives. Implementation will be difficult unless staffing and technology requirements are built into the planning process. This is one reason why much of the work we do at .orgSource is centered around integrated planning. A strategy that’s created in a vacuum is a plan without legs.

The board plays the role of visionary.

In an integrated planning process, the board plays the central role of visionary. Instead of addressing the “how to,” they concern themselves with the bigger issue of “why.” After fundamental questions are identified, the staff, using their knowledge about available financial and human resources, sets the objectives that will realize the board’s vision.

If your strategy missed the mark, and your team lacks the training to achieve the objectives, consider using freelance support until you are certain what skills will be needed. The availability of a broad base of talent on demand is something associations should leverage.

Assess Systems

System deficits can be tricky to identify. Consider a professional evaluation to pinpoint gaps and new platforms that are needed. Kevin describes the benefits of a technology assessment like this.

“A technology assessment involves being a detective. Most of the time, a broken system is only a small part of the picture. There is usually a mystery hiding in plain sight. Finding the right solution requires research, observation, psychology, and logic. As a compulsive problem-solver, this is a place where I love to hang out.”

When you understand where your team needs to grow and which new tools are required, begin investigating how to secure those resources and develop a timeline. Consider a phased approach that lets employees know you are working to improve results without over-extending people or finances. Share your decision-making with the board at every juncture to ensure a positive outcome.

Are Work Processes Efficient?

The point of state-of-the-art technology is to meet your members’ needs more efficiently. Across-the-board staff training ensures that the systems you purchase will deliver a return on that investment. I’m always surprised to see an organization using the new tech stack to continue producing cookie-cutter messaging.

Becoming a digital organization is an evolving process. Out-dated thinking and business practices will need to be abandoned along the way. Training must include more than just the ins and outs of new platforms. Staff should learn to incorporate data analytics into their work and to approach problem-solving from a digital perspective.

Focusing attention on digital literacy ensures that each person on your team will be able to access data to make objective decisions, create customized education, products, and services, and use member feedback to build relationships. Learning to use digital tools gives employees the confidence to innovate and incorporate new processes designed to make their jobs easier and more fulfilling.

Is Your Culture Advancing Your Goals?

Culture is the foundation of your business.

I’ve never understood the reluctance to provide continuing education for fear employees will grow into another job.  By encouraging staff development, you signify that learning, curiosity, and professionalism are organizational imperatives. These qualities drive behavior and attitude. If you’re not accomplishing your goals, it may be because you aren’t promoting the right values.

I’ve written several posts about culture recently. Your culture is the foundation of your business. If there were cracks before the pandemic, stress and the newness of remote work may have created larger fissures. Make an honest assessment and ask yourself whether repairs are needed. Here are some symptoms of an ailing culture:

  • Absenteeism and turn-over
  • Management by fear
  • Behavior ruled by policies and procedures
  • An HR department functioning as police
  • Diversity, equity, and inclusion in name only
  • A mission that is lost in minutia
  • Gossip, cliques, and backstabbing
  • Reluctance to ask questions

It’s a cringeworthy list.

Culture is a systemic issue. Fixing one person won’t fix your entire organization. Actually, that’s not true. If you are the CEO, you are also the only person who can solve the problem. Admit that there are issues and own up to your responsibility for allowing them to happen. Find help to give your team the right spirit. Then get your goals back on track.

That last bullet point is important. Without questions, innovation and growth are impossible. Don’t just ask the questions I’ve posed here once a year. Build regular assessments of your strategic progress into your schedule. The more you scrutinize the big picture, the fewer surprises will be hiding in the details.