A Lesson for Aspiring Leaders

3_Lessons_for_Aspiring_Leaders_Wired_4_LeadershipA Parable for
Aspiring Leaders . . .

The young woman nervously held the three white envelopes in her hand. As the newly appointed non-profit CEO, she was about to meet with the entire Board of Directors for the first time. Her predecessor–a longtime nonprofit executive–had warned her the Board could be contentious at times. She was nervous and a bit apprehensive, yet determined to be confident in her new-found leadership role.

He had also done something else. On his last day in the office he handed her three envelopes, neatly hand numbered 1, 2, and 3. “If you ever find yourself in a tough situation with the Board”, he said, “You’ll find all the advice you need in these three envelopes.” She had quickly tucked them into the pocket of her notebook, while thanking him for his advice. In the weeks that followed, she had pretty much forgotten about them.

Now in the midst of her first meeting with the Board, complaints about poor member service, lack of new membership growth, and outdated services were flying about the room. Without attracting attention, she gently slid the envelope numbered 1 out of her notebook, and opened it. She was taken aback by its message:

“Blame Your Predecessor.”

She felt uncomfortable with the message. Still, given the Board’s voracious complaints about the current state of affairs, the new CEO wondered if she could find a way to broach it diplomatically. It was the perfect opportunity to contrast herself and her leadership style with that of her predecessor without being harsh. So she spoke up, telling the Board that while her predecessor didn’t get everything right, the framework was strong, and she would dedicate her heart and soul to returning the organization to a pathway for success.

As the weeks went on, few things went as planned. The new CEO found herself sitting with an unhappy Board in the following months as well. Exasperated by the Board’s impatience, and their continued bickering about the state of affairs at the nonprofit, she once again returned to the two envelopes remaining lodged in her notebook pocket. Opening the envelope labeled number 2, she quickly unfolded the paper to see the words:

“Announce Your Re-Organization Plan.”

She pondered the idea for a bit. Things needed to change. She had ideas about how the organization could be more efficient. There were ways staff could be more responsive to members, donors, and supporters. Over the past many weeks, she had reviewed policies, analyzed service statistics, and scoured organization charts to uncover issues and figure out where and why things were going wrong. Maybe, she thought to herself, this is exactly what the organization will need—a reorganization.

At the next Board of Directors meeting, with a renewed sense of purpose, and a fresh re-organization plan in hand, she stepped forward to announce her plan for re-organization of the operation. Staff would be re-assigned. Redundant positions eliminated. New programs would be launched. A fresh direction was at hand.
Her plan gained the support of a slim majority of Board members. She felt so much better. Sure, she would still have to prove she could deliver, but at least she had a Board approved plan.

Determined to propel the organization, she set about the hard work of leading change. She worked closely with staff, helping them re-orient themselves to the new plan. She re-defined their roles and focused them on the tough tasks of improving member service. Prospecting and acquiring new members was now a priority. Finding new value and innovations among the varied services and products offered by the group became a key activity. While her team appeared engaged, it was clear this was a long slog, requiring both continued dedication, and sharp focus in the face of all the changes.

With the next Board of Directors meeting now just a few weeks off, the CEO’s nervousness and anxiety returned. The entire team had made progress. Member service satisfaction stats were improving. Service costs had fallen somewhat. The organization was still struggling to re-define itself. Committee leaders were voicing complaints about changed priorities, and some staff were quietly resisting changes. A few had even taken to communicating by e-mail directly with the Board Chair. In a few instances they surreptitiously met with volunteers to discuss “behind the scenes” activities of the organization, stories about the CEO’s work habits,  and sharing incomplete information intended to cast the activities of their boss in poor light.

Preparing to join the Board of Directors meeting, the CEO grabbed her portfolio and headed into the gathering. The meeting did not go well. Several of the Board members publicly shared complaints they had heard from committee chairs, and in a few instances from members as well. After much back and forth, the Board Chair revealed the extensive “behind the scenes” communications and complaints he had received from the staff. As the meeting wore on, the discussions grew more contentious with some Board members supporting the CEO and the change efforts, while assailing those who opposed them. As the CEO continued to listen to the discussions and take rapid-fire notes, the envelope marked “3” slipped from behind the pocket in her portfolio.

The room was abuzz in chatter—accusations, counter accusations, fault-finding, rich opinions and endless discussions about what to do. The CEO seeking a respite from the conversations, and inspiration in the moment, decided to open the third envelope. As she did so, the hum of the discussions–still as loud and vibrant as ever–seemed to subside as she deliberately removed the paper from the envelope. Slowly, she unfolded the paper hoping with all her strength, she might find inspiration in the midst of this dysfunctional and maddening conversation. Gradually, a smile spread across her face. Neatly typed in the center of the page was one sentence. It read:

“Make Out Three Envelopes.”


The Three Envelopes parable as been told in various forms for decades. While its origin is unknown it may offer a thoughtful lesson for new and aspiring leaders.

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