I am a new grad at a unicorn, and like many other new grads I am also struggling at my job and facing severe impostor syndrome / stress / anxiety. All other employees are very highly capable and the bar here seems to be very high. I was curious how much is it okay to share with my manager? Can I be 100% transparent? Or do I have to be strategic about how I communicate? I am afraid if I am being too open about how "unskilled" I feel I am, he might see me as less capable and not deserving of more impactful projects.
Speaking about strategic communication, I realised I struggle with it in general. I am a bit too authentic and direct, both in daily life and professional life. How does one learn the art of strategic / diplomatic communication?
I think you need to separate 2 things here, imposter syndrome, and manager transparency.
About the imposter syndrome, I think it's totally normal to feel this way being a new grad and a new member in the team, if this stays with you after 1 year, then you may want to address it, otherwise, just keep learning from everyone around you, and take every chance to do so.
Regarding manager transparency: IMO, it all depends on 2 things, Trust and Respect.
If you fully trust your manager, and you both have a good respectful relation, then I would be totally open with things I would not be with other managers, think looking for other opportunities, looking for outside mentors, etc... This ensures you gets a sincere advice, and makes sure he is also in the know to make sure he reaches out to hire a replacement etc.. And most importantly, it helps keeping the bridge solid.
In addition to Amazon's answer, I'd highly recommend going through this course from an ex-VP at Amazon: Managing Up: Build Effective Relationships With Your Boss