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Managing up under pressure

(November 14, 2023 Newsletter)

When faced with an increased workload, heightened emotions, or unusual pressure, it can be challenging to maintain a smooth relationship with your supervisor, whether they’re the CEO, a senior exec, or otherwise.

Why it matters: The dirty secret is that when curveballs come at your organization, the most senior decision maker/s often need to make faster decisions with less information.

  • Chances are, as the pressure piles up, your supervisor is hoping you’ll step up your mindreading game just as their ability to give clear instructions decreases. It puts you in a position to do more guessing or improvising, since it’s unlikely that they have more clarity than what they’re giving you.

  • Inevitably, a communication gap will emerge and, while you may not be the instigator, you certainly have an interest in closing it as quickly as possible.

What you can do:

1. Self-regulate – it always starts with checking what’s going on in your own mind and heart when brief and unclear instructions come your way. What story are you telling yourself as you read your boss’ email, text, or hear their request? Where in your body is tension emerging?

  • Double check any resentment, blame, or other kinds of resistance. However hard it may seem in the moment, remember that their worst tendencies may be exaggerated in times like these… but so may yours.

2. Take a quick task-related inventory:

  • How clearly do I understand what this task or project should look like when it’s done?

  • What do I need to succeed? How much of it can I get myself, without involving them?

  • What immediate obstacles come to mind? What workarounds can I try?

  • What will I need to set aside to prioritize this? What impact will that have?

3. Reflect back your understanding and ask for clarifications: before ending the conversation, convey what you perceive the final product is, by when they want it, and check that you understood. Here are some questions to ask them:

  • When I’m unsure about next steps, do you want me to circle back to you, follow up with someone else, or use my judgment and just keep going?

  • Are there any aspects of this that you feel very strongly about that you want me to take into consideration? Any non-negotiables?

  • If I need to choose, do you prefer I prioritize speed or accuracy?

  • What kind of updates would you like along the way, and how often do you want me to check in?

  • In order to prioritize this, X and Y are going to have to take a backseat – are you ok with that? Do you prefer that I (or you) reassign them or just push them out?

4. Take notes for yourself: don’t rely on memory, so you don’t have to circle back on things you already discussed.

Ultimately, the goal is to get as much information as possible, considering there may be big gaps in what’s known overall, and to set as clear expectations as possible, considering how unclear so much may seem.

By interpreting their intentions generously, you’re setting yourself up to receive that generosity in return.


The Coaching Corner

When your team member says they’re fine, but you sense they’re not.

To push or not to push… that is the question.

1. Broach the subject by expressing your care and pointing out specific behaviors

  • “I wanted to check in and see if everything’s ok. I noticed in yesterday’s team meeting that you had your camera off and your voice was shaky when you spoke.”

2. If the answer comes back “I’m fine” or “everything’s fine” consider whether you’re just checking in simply because you’re concerned about them or whether their or other people’s work is being impacted. If the latter, it’s worth pushing.

  • “I’m not only asking because I care about you as a person, but also because you’ve missed a few key deadlines this week and I’m wondering if there’s something going on you’d like to discuss.”

3. If the answer is still no, remember that you’re not their only resource, and that now may not be the only time to talk about it. You can leave the door open to circle back to you when they’re ready or you can express the hope that they’re getting whatever support they need elsewhere.

  • “I respect that. If something is going on and you just don’t want to talk to me about it or now isn’t a good time, just know that my door’s always open and/or that you’re confiding in someone else.”

Of course, there is always a chance that everything really is just fine – so I wouldn’t come back to it after this interaction, unless the noted behavior continues or worsens.



“War Therapy” - I hesitate to post anything too directly related to Israel’s war with Hamas, but in this case, I can’t help myself. In a special episode of the podcast “Unholy,” co-hosts Yonit Levi (Channel 12 News, Israel) and Jonathan Freedland (The Guardian, UK) discuss how their relationship has been strained since the war began. It’s the kind of courageous conversation we rarely hear.

  • For my insights on the episode, and the hallmarks of courageous conversations that I heard while listening, read my LinkedIn post from last week on the topic.


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