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Coaching Clinic Lesson #6: Two Bosses, and the Limits of Expertise

The sixth in a monthly series of 11 posts.

Karina has two bosses.

Most young managers wouldn’t prefer that, but Karina relishes it. She likes that each of her bosses offers her a different perspective.

When Karina encounters a knotty problem, she presents it to Boss #1 or Boss #2 depending on which perspective she values most for that particular problem.

Not long ago, one of Karina’s top performers, Damian, announced that his wife, a breast cancer survivor, had suffered a serious recurrence. Damian told Karina, “I will be in and out of work and I don’t know how long this will last – it might be weeks or even months. In any event, I won’t be too reliable on the team until my wife’s condition stabilizes.”

Karina was stumped about what exactly to do about Damian’s dilemma, and his blunt message. She felt for her employee and his family, but the company needed his presence in order to bring a long-term customer project to completion.

She decided to first take the problem to Boss #1. His experience in the business and his bent towards practicality, she reasoned, might give her the direction she needed in a delicate situation.

Indeed, that’s exactly what happened.

Proposing Ideas

After asking her about the condition of Damian’s wife, Boss #1 spent a few minutes proposing ideas Karina hadn’t considered:

“One thing you should be sure to do is communicate how much we value Damian, and want to be there for him.”

“You’ve got to work with him to come up with a modified schedule that would allow him extra time with his wife, without severely impinging on his work. Stress a reasonable balance between his needs and the company’s needs.”

“What we don’t want to do is keep the understanding loose and undefined.”

After reflecting on Boss #1’s advice, Karina decided to check in with Boss #2. She rarely consults both bosses on a problem, but this one was personally important to her. She wanted to be sure her response to Damian was helpful and appropriate.

Thoughtful Questions

Her 40-minute conversation with Boss #2 put her on the receiving end of a few thoughtful questions:

“What kind of relationship do you have with Damian?”

“When he talks to you about his wife’s predicament, what thoughts and feelings come up for you?”

“What do you think he needs from you?”

“What do you need from him regarding this customer project?”

“What parts of the project can be off-loaded to others?”

Boss #2’s questions got Karina thinking about how she was doing with Damian’s situation.

She reflected on the internal struggle she experienced six years earlier when her own father entered hospice with emphysema. She remembered the pull she felt to be at work, not wanting to drop a couple of pressing job responsibilities, and how she asked her boss for understanding and negotiated to spend extra time with her dad and family.

Karina recalled how meaningful it was for her to see so many co-workers at her father’s funeral service three weeks later, after her long spell of not being very present at work.

As she thought about it, Karina developed more clarity about how she wanted to approach Damian. “The key for me,” she told me later, “was engaging Damian in conversation that reflected both my head and my heart.”

Karina’s story displays the sharp distinction between Boss #1 and Boss #2:

Boss #1 is The Expert.

Boss #2 is the Connecting and Curious Coach.

Inside every leader lives both these bosses.

Every leader, in every conversation, decides which boss to pay attention to.

Sometimes, more attention must be given to Boss #1, because the situation is urgent, or because only The Expert possesses the answer to a highly-technical question. In those situations, a leader’s subject matter expertise might be the last resort that saves the day.

In a culture dedicated to developing leadership in others, Boss #2 takes the lead. The focus here is on helping others grow by delivering coaching, not answers. In the example above, Boss #2 is focused on Karina’s development as a leader, while Boss #1 is focused on Damian (the problem).

Automatic Functioning

I’ve noticed that leaders function more automatically as Boss #1 than they do as Boss #2. For most, demonstrating a desire to connect and coach has to be intentional. Being The Expert, on the other hand, often comes naturally. It’s what we have largely been rewarded for throughout our lives and careers.

When operating as Boss #2, a leader has to be willing to put away distractions, focus on the person across the table, become genuinely and humbly curious, ask thoughtful questions and permit the space for another to take appropriate responsibility for their own decisions and actions.

Boss #1 uses phrases like “You need to,” and “We should make sure.” He rarely asks about the other, or reveals anything about himself.

Conversely, the language of Boss #2 is littered with what, how, and when questions. It’s common for her to show interest in the coachee’s response to the problem, and to share information or thinking about herself.

Boss #1 encourages obedience, with little requirement to think and grow.

Boss #2 stimulates growth, initiative and responsibility.

The lesson is simple and clear: If you want to become a world-class coach, make Boss #2 your best inner friend, and an invited guest in every interaction.

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