Stop Hiding Behind Executive Assistants To Lead

First off, let me be clear about something. Executive assistants are superheroes. They just don’t wear a cape. (In fact, I’ve written about it – over here.)

But that sentiment does not preclude me from suggesting a different sort of maxim: leaders who hide behind an executive assistant are not doing themselves any favours when it comes to the practice of leadership.

Take, for example, a vice-president we’ll call Jason. His assistant’s name is Sunny.

Jason has eight direct reports. Four of them—including Sunny—are located in the same building at company headquarters in San Francisco. The other four work in different locations across the US.

Jason has decided to pay a visit to the four directors under his leadership who work outside of San Francisco. He’s overdue for some real face-time. Jason instructs Sunny to set up the meetings. So far, so good. Nothing wrong or unusual here.

He visits Sandeep first in Hoboken, New Jersey. The meeting got scheduled for 9 am on a Tuesday, but Jason ran into traffic in the Lincoln Tunnel. Jason loves staying in Manhattan whenever he can, even though it would be far easier to stay in Hoboken. After all, he has no direct reports working in Manhattan.

Instead of calling Sandeep personally to say he was going to be several minutes late, Jason calls Sunny. “Hey Sunny, there’s an accident in the Lincoln Tunnel, and I’m going to be late for my meeting with Sandeep. Can you let him know?”

Ever the dutiful executive assistant—and up at 5:30 am Pacific time just in case the boss needed something—Sunny calls Sandeep and lets him know the bad news. It’s nothing new. It’s happened several times before.

After the meeting with Sandeep, Jason catches a short flight in the afternoon out of Newark Airport for Boston. He’s set to meet on Wednesday with Anita and Jacques. Before those one-on-one meetings are set to occur, Anita and Jacques arranged a customer visit knowing that Jason would be in town. They worked with Sunny to ensure everything was fine with Jason’s morning schedule.

In preparation for the customer meeting and a week prior, Anita and Jacques sent Jason a well-prepared client briefing document. They also included a PowerPoint deck that was intended to be presented to the customer.

While waiting in the lounge to board the flight to Boston, Jason finally perused the briefing document and the customer PowerPoint file. He had questions. He also had a few ideas and changes.

Instead of calling Anita and Jacques from the lounge, Jason made the changes to the deck, sent it off to Sunny, and instructed her to send it directly to the customer before the meeting on Wednesday.

Thankfully, Anita and Jacques were copied on the email to the customer from Sunny. Unfortunately, they had no idea that Jason was making any changes to the presentation.

They read Sunny’s email Tuesday night, licked their wounds, and met Jason on site the next day at the customer meeting. He ran the show, much to the chagrin of Anita and Jacques’s wishes. In their eyes, the meeting did not go well at all. The changes to the presentation that Sunny sent without their involvement ran counter to their long-term customer goals.

After their respective one-on-one meetings concluded, Anita and Jacques hit a pub and drank a few pints of Kilkenny. “Can’t wait until Jason comes to visit again,” they commiserated with one another.

After Boston, Jason flew to Chicago to meet up with Laetitia. The last time they had met face-to-face was nine months prior.

During the one-on-one meeting on Thursday morning, Jason asked Laetitia a question: “By the end of the day, can you send Sunny a detailed update to your business development plan? I want to review it on the plane ride back to San Fran tonight and provide feedback.”

Ever the proactive taskmaster, Laetitia had it into Sunny by 2 pm.

Jason reviewed the file on the plane as promised. He then sent his detailed comments to Sunny and asked her to send them back to Laetitia without delay.

Where does that leave us with the story of Jason and his assistant?

Jason has no idea what incredible harm he is causing when it comes to the culture of his team. In this example—with the names and cities changed to protect the innocent—Jason not only exhibits poor leadership, but he also uses his trusty assistant as a communication prosthesis with the team. Neither of it is good.

One three-night business trip resulted in the following:

  • Using an assistant to inform a team member he was going to be late, instead of calling directly.
  • Using an assistant to engage candidly with a client, usurping the team’s game plan.
  • Using an assistant to act as a go-between for feedback between Jason and a team member.

In each of these cases, Jason may think he’s more efficient using Sunny as a conduit, but there’s an enormous issue he is causing.

Jason is eroding trust. It may even become vaporized.

Behind the scenes, Sandeep, Anita, Jacques and Laetitia are having themselves a grand old time discussing Jason’s inept leadership. The digital water cooler is rife with jokes. They are all at the expense of the leader who uses an executive assistant as an unfortunate communication proxy.

And it occurs far more often than it should in today’s corporate world.

My advice for leaders? Whenever possible, communicate directly with your team and do not use your executive assistant as a substitute teacher for communications.

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Hey! I'd love to read what you think. Surely you have an opinion. Love, Dan.