Loneliness is a theme found in many leadership memoirs. While I can’t claim to have faced anywhere near the same magnitude of challenges as Ben Horowitz, this quote from his book The Hard Thing About Hard Things implies that this feeling isn’t reserved for billionaire founders or battlefield generals:
In life, everybody faces choices between doing what’s popular, easy, and wrong versus doing what’s lonely, difficult, and right.Ben Horowitz
One way to relieve a portion of this leadership loneliness is by increasing the transparency shown by a manager to their employees. Part of the employee+manager relationship is helping the employee develop as a successor for the manager’s role. That means exposing the employee to the types of decisions that the manager makes–both big and small. Does the employee have capabilities required to do the job well? Perhaps more importantly, do they want to do this job? Greater transparency by the manager can help the employee learn more about the day-to-day reality of a more senior position, and can help the manager learn more about the employee’s readiness and willingness to take on greater responsibilities in the organization (those responsibilities could be functional or political).
Because many decisions that a manager faces will impact the employee, understanding the employee’s perspective can be an input to the decision itself. Asking the employee, “What would be a good outcome for you? What about for others on the team?” can help the manager identify blind spots in their perspective or approach the decision from a different frame of reference.
This leads to a dynamic where both transparency and trust must increase together for the strongest working relationship: one of partnership. The manager is sharing sensitive information with the employee. The employee is sharing candid responses. Both parties expect the other to treat the information with discretion. A high level of transparency without trust leads to a transactional, fleeting relationship — like a patron who will visit any shop that offers the best deal. A high level of trust without transparency is like the attitude of a pet toward its owner — always eager to take a ride in the car without knowing what the journey entails.
The risk of greater transparency by the manager is to create an expectation of an outcome that the manager can’t fulfill. For example if a potential organizational change — promotion, raise, prized assignment — is blocked elsewhere in “the machine.” This scenario will kick trust+transparency development in this relationship into a negative feedback loop, with the manager less likely to be transparent and the employee less likely to be trusting, both out of fear of inflicting further damage to the relationship, which of course is becomes self-fulfilling.
The manager’s challenge is not only to be selective when sharing the decisions they face with employees, but also to do so in a way that minimizes expectations they can’t deliver. One technique is for the manager to conduct decision reviews with the employee — after the fact — in the style described by Annie Duke in her book Thinking In Bets. This interaction should maximize the transparency and trust between the two parties without raising the risk of of a disappointing outcome for either.
So as with all things in life, there is such a thing as too much transparency from a manager to their employees. But when chosen carefully and supported by a high level of trust, moments of transparency can strengthen relationships and accelerate careers.
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