Leave your assumptions at the door - Deepstash
A Job Seeker's Guide

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A Job Seeker's Guide

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Leave your assumptions at the door

The biggest reason people can't manage up is that they don't understand their boss's job. You only see a small part of what your manager does.

  • Regularly align on these two questions: What is success for me personally? What is a win for my manager's team?
  • Show your work. It's about knowing what your boss wants, then ensuring that you provide them with a steady drumbeat of the things they care about.
  • Understand what is your manager's most urgent priorities, then adjust accordingly.
  • Focus on what's keeping your manager up at nightΒ and identify what you can take off their plate.

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Get comfortable with feedback

  • Feedback should be ongoing and not be left to a formal discussion during performance reviews.
  • Allow positive feedback to come through louder. When you receive constructive criticism, try to stomach it even if it first rings false.
  • ...

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Hone your delivery for communication

  • Open up about your "work love language." From early on, share with your manager what motivates and drives you, including what's important to you outside of work.
  • Observe how your manager listens and processes inputs. If he stops listening halfway t...

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119 reads

Boost your chances of hearing 'yes' to your ask

  • Leave some breadcrumbs. Don't hoard information until you feel you have all the answers. Anything complex needs multiple exposures for someone to internalise the concept.
  • Create a shared understanding of the problem. Share information you have and co...

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132 reads

Managing up - How to manage your boss

Managing up - How to manage your boss

The relationship between a manager and their report is a two-way street: navigating the road falls on both parties.

Some managers are easy to get along with, while others can feel near impossible. However, there are several strategies you can use to manage up:

  1. Le...

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315 reads

Set the tone in your 1:1s

You likely got a regular 1:1 meeting with your manager. While they can feel more obligatory than critical, meetings are a powerful tool to build trust and up-levelling your impact.

  • Ensure that the shared agenda and notes are pre-populated with topics y...

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Share your impact the right way

Share your impact the right way

  • Give regular updates. Written asynchronous communication is vital in the remote world. Managers can read at their leisure and comment async rather than live discussions.
  • Send weekly "State of Me" emails to your boss. Share what you're doing, what y...

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86 reads

Build lasting rapport and trust

  • Build rapport. You don't have to be best friends to build rapport. However, show interest. Pick a few topics you feel are common ground, such as kids or a shared hobby.
  • Get tactical with building empathy. Assume positive intent. Check assumptions and...

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93 reads

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You don’t need to β€œget out of the building”

One of my biggest pet peeves when it comes to the startup ecosystem is the number of startup coaches out there spouting the same recycled wisdom from Steve Blank or the Lean Startup about how you have to β€œ get o...

Take the lead of your performance review

  • Be sure to know what's expected of you. It’s really difficult to improve within your role when expectations have not been properly communicated to you.Β 
  • Ask for feedback. If your company doesn’t have a formal, regular feedback process in place, seek ...

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