3 tricks for handling a difficult boss, from an executive assistant at Slack

  • On an episode of “Reach,” Jessica Vann interviewed the executive assistant Shelley Trask.
  • Trask said dealing with a difficult boss starts with speaking to their values.
  • Explain the consequences of their actions and show how you can help save them time.

Shelley Trask, an executive assistant and coach for other assistants, has been working for Slack’s cofounder and chief technology officer, Cal Henderson, since 2018. On an episode of the “Reach” podcast, she told the Maven Recruiting Group founder and host Jessica Vann that she and Henderson have “a very efficient relationship.” But over the course of her career, she’s supported other executives who haven’t been as easy to work with.

Here’s how she’s learned to navigate tough work situations and influence her boss’ behavior for the better.

Speak to their values

When dealing with a difficult manager, it’s important to identify what they hold true or what speaks to their values, Trask said on the podcast.

“For example, if someone really wants to be respected — so they’ve got a bit of an ego — or they just don’t want people to disrespect them, you really want to explain to them how changing their negative behavior will add to people’s perception of them.”

“The impact of that is that your direct reports feel undervalued,” she said she told one executive who was always running late to one-on-one meetings. “I know that you care about attrition, I know you want to make people feel respected, so I’d suggest that we work together and see how we can keep you on time.”

Respect their time

Trask told Vann that she gets 30 minutes a week alone with Henderson. Her goal during that meeting, she said, is to “make sure that I haven’t done anything to make him think that the time isn’t worth spending with me.”

With Henderson, for example, she might suggest ways to automate or take over tasks he doesn’t need to be involved in, such as choosing lunch or planning presentations. “Identifying what your executive can let go of is going to be a really big game changer for both of you,” Trask said.

If your boss tends to miss one-on-ones, she said to ask them, “What can I do to make it easier for you to find that time to spend with me?” or suggest trying a different format for the meeting, such as a shared document or a phone call.

For managers who have a hard time delegating, Trask said to suggest bucketing tasks: “Maybe there’s buckets that you’re willing to let me make decisions on your behalf where you feel like you’re going to be OK with whatever the decision looks like.”

Remember your power

When Trask coaches other executive assistants, they often tell her that they struggle with self-esteem and find it hard to speak up, she said. Her advice to them is to consider how crucial their role is to the success of the executive and company as a whole.

“Literally say, ‘My job is to make you more successful, to save you time, and to take on things that you shouldn’t be doing,'” Trask said.

“EAs are the heartbeat of the whole company,” she added. “We have some of the most amazing power.”