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July 20, 2021

Finding Your Scottie Pippen

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During the 1990s there was no sports phenomenon more compelling, or more dominant, than the Michael Jordan-led Chicago Bulls. In a period of eight years—two of which Jordan spent playing baseball poorly—the Bulls won six NBA titles, defeating the likes of Magic Johnson, Charles Barkley, and Karl Malone along the way. If you were to dissect the success of these Bulls teams, your analysis would probably take all of two minutes, and it would begin and end with two words: Michael Jordan. The end. In most minds, you could have surrounded Jordan with four guys from your local rec league and he would have made it work. Sure, he had some talented role players around him at times, but it was all Jordan, right? While there is no denying that Jordan was the clear leader and the most important piece on these teams, there is also no denying that Scottie Pippen was his clear #2. The only player on hand with Jordan for all six titles, Pippen played an invaluable role in Jordan’s success, and is considered by most to be the “NBA’s greatest secondary player” ever. Why, then, is it so easy to overlook the importance of Pippen? Why is it almost natural to gloss over his Hall of Fame career, and go right to Jordan’s accomplishments? In part, it’s because we rarely appreciate, or even acknowledge, the value and rarity of a great #2. In spite of this blind spot, a strong #2 can be as important to your organization as Pippen was to the Bulls of the 1990s. 

#2s in the Marketplace

My first head-on collision with this often overlooked role came early in my executive coaching career when I began work with a gentleman named Carl. At the time, Carl (not his real name) had recently been named the COO of a massive non-profit organization, and he was in the process of navigating the precarious terrain created by a very involved and ever-present founder. In Carl’s situation, just like in Pippen’s, there was no mistaking who the #1 guy was. It was the founder. Carl, though, had an incredibly important role to play as well. He was the right hand for the founder. He was the guy who made things happen. He was the guy who kept the company in balance and on point. He was the guy who took the founder’s vision and interpreted it for the rest of the organization, and he did so magnificently. Unfortunately, not all relationships between the #1 and #2 individuals in an organization are as successful. More often that not, ego, poor communication, and lack of trust doom a potentially successful #2 before he or she even begins. While each situation and organization is certainly unique, I’ve found a few things to be universally true when it comes to #2 assignments.

  1. Trust is preeminent  – The # 1, whether they are the founder, CEO, or president, must have implicit trust in the #2. Not stupid and blind trust, and not begrudging trust, but a trust that keeps the second-guessing of motives and ambitions at bay. If the #1 is constantly looking over his or her shoulder, the roles become counterproductive.
  2. Define success – Before the first meeting is held or the first memo is sent, the #1 and the incoming #2 should identify and document what success will look like (both soft and hard elements). Not all #2s have the same roles and responsibilities. In fact, a wonderful Harvard Business Review article identified seven basic roles that a #2 can play. These roles may range from assisting in execution to mentoring key leaders to preparing to take over the reins of the organization. Whatever the role is, the better each party understands it and determines metrics for success, the greater the opportunity for success.
  3. Understand organizational context – To truly add value, a #2 must know the vital signs of the organization and understand the motivations behind his or her hiring. Is the company in a growth mode? Are they looking for innovation or execution? Has growth flattened out? Are they looking to streamline or drop dead weight? What challenges are currently demanding attention and what dangers are around the corner?
  4. Regularly evaluate and adjust – From day one, the #1 and #2 must set up calendar dates for future evaluations. In Year 1, consider doing a formal review every quarter so that instant pivots and adjustments can be made. In Year 2, space it out a bit, but maintain constant markers to gauge success. For these evaluations to be effective, both parties need to come prepared and ready to talk honestly about what is working well and what is not.
  5. Structure for success – This may sound silly. After all, nobody structures for failure, right? While no one intentionally sets up a #2 to fail, it is incumbent upon the #1 to do everything he or she can to create a situation both internally and externally that allows for success.
  6. Be realistic – Nearly every #1 I’ve encountered struggles at some point or another to accept the gap between their passion and the passion of EVERYONE else in the company. No matter the title, compensation, or benefits a #1 bestows upon a #2, the latter will rarely have the emotional connection or feel the level of ownership that the owner or founder does.

When to Bring in a Strong #2

When a visionary founder can’t seem to ever get past the exhausting hub and spoke model of leadership … it could be time for a strong #2. When an organization keeps hitting the growth ceiling and bouncing off … it might be time for a strong #2. When your vision has attracted great talent and a devout tribe, but it’s time to deliver on the big vision … it might be time for a strong #2. When a new generation has taken over the key drivers of the company … it might be time for a strong #2. A great #2, whether you call him COO, vice president, chief of staff, executive assistant, staff director, or first mate, may very well be the difference in realizing your vision and spinning your wheels.

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