The challenges of flying solo


“Ninety percent of the trouble we have with the chief executive’s job is rooted in our superstition of the one-man chief.”

– Peter Drucker, The Practice of Management (1954)

The conventional wisdom is that a team should have only one manager, and an organization only one leader. This seemingly unassailable truth has been baked into the structure of thousands of organizations and millions of teams around the world.

In theory, this allows us – as managers – to be swift, effective, and accountable in our role. The swiftness is meant to come from giving one person the right to close out any on-going dialogue or deliberation. The effectiveness is meant to come from getting a person with the right skills, habits, and self-awareness in the role. The accountability is meant to come from clarifying whose neck to squeeze if trains run behind schedule, and whose head will roll if trains run off the track entirely.

Any manager can tell you that the theory rarely works out in practice. Managers – at many levels, in many functions, and in many industries – find themselves too backlogged to be swift. Or too fragmented, hurried and unprepared to be effective. Or too deep in the details to be held accountable. Or all of the above.

We are not swift, because we lack the hours in the day or days in the week to catch up with our work, to say nothing of getting ahead. With scheduled commitments from dawn to dusk – punctuated by unscheduled fire drills to keep things lively – we easily become the bottleneck for the team.

We are not effective, because we lack the skills, habits or self-awareness we need, particularly when new to a role. Success in a previous role does not give us the skills or habits we need in the next one. As the saying goes, what got you here won’t get you there. This is exacerbated by a self-awareness gap. That is, we see the errors and biases of others, but not our own.* Rather than having our hard edges sanded down with time, experience, and candid feedback, our authority shields us from the truth. This leads to a great deal of variability and inconsistency in how managers manage, and leaders lead. Not only do different managers often handle similar decisions differently, even the same manager can shift approaches according to time, circumstance and mood. At its best, this capriciousness is the stuff of happy hour roasts and Dilbert cartoons. At its worst, it is the source of chronic stress and frustration in the workplace.

Finally, long before we arrive at what it takes to deliver results in a role, we arrive at what it takes to deliver excuses. Immersed in the day-to-day, we quickly become fluent in the unique challenges of our situation. And then we wear these challenges as plates of armor to protect us in monthly or quarterly performance reviews. We often know too little to deliver, but too much be held accountable.

In the very best case, we acquire the skills, habits and self-awareness we need to be both swift and effective. In which case we become altogether indispensable. When it comes time to move on, we leave behind shoes too big to fill. In this case, the bomb of our failure – to prepare successors – does not go off until we have already left the building. Those left at the scene are tried and found guilty for our crime.

But wait. Let’s not be too quick to judge. It is the theory of the solo leader, the superstition of the one-man chief, that is to blame. It is just compelling and pervasive enough to blind us to the alternatives.

More to come on the specific challenges of flying solo.

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