During the First Quarantine of 2020, one acquaintance told me, about another acquaintance, “I asked her how she was doing and she said, ‘10 of 10, everything’s perfect’ and I thought, during quarantine when no one can leave their house, no one is doing perfectly. Plus, she’s also almost 9 months pregnant, and no one who is almost 9 months pregnant is feeling like they’re a perfect 10. She’s lying to me because she wants to paint her life to the world as being picture-perfect when self-evidently, it just isn’t—and not in a personal way. In that situation for anyone, it can’t be perfect.”
Good observation, and guess what? Your boss or client will think the same about you and your work if you never acknowledge any frustrations or problems. Of course, you will have frustrations and problems in your work, so if you don’t, that can only mean one of two things: either you’re not doing complex or important enough work (in which case, why is he paying you so much?) or you are but you aren’t sharing the challenges with him so he can help you overcome them (in which case you aren’t focusing on solving the problems and overcoming the challenges.) In either case, the situation isn’t ideal.
There is one solution: share your challenges and problems with your boss. He’s rooting for you (that’s why he hired you!) and he wants to help you overcome them.
But there’s a fine line to walk on, don’t overdo it. When this becomes a regular topic of conversation, then it is too risky that it will feel like he’s your psychologist, or you need to up your game to solve problems on your own. Remember, he’s hiring you to solve problems, not to sit there and complain about your life!
How often should you do this? To answer that, I’d point out that there’s a spectrum depending on how emotionally charged the frustration is. The less the emotional charge is, the more frequent it should be; the more emotionally charged, then the “once per 6 months, at most” comes into play (depending on your personality, your relationship with your boss or client, and so forth.) Once per year shows you’re human. Once per month becomes a source of frustration for your client or boss. So, use the above as guidelines for the right frequency.
What sorts of pain am I talking about?
- Other employees treating you badly or disrespectfully.
- Your boss or client himself treating you badly or disrespectfully.
Above all, when you talk about pain points, make sure you remember the previous chapter on how to frame criticism, above all, framing it as unintentional and framing it from his eyes with the most optimistic interpretation possible. Even if that interpretation stretches the bounds of likelihood.
I’d also recommend using a similar framework for talking about personal frustrations or problems in your life, that have nothing to do with work. It’s only good for your boss to know if you’re getting divorced or any other challenges that could affect your work behavior. As a rule of thumb, if they know about your personal non-work challenges, they’ll give you more space and flexibility and relax their standards for you during the duration of the challenging moment. But if they don’t know, they’ll just be increasingly disappointed in your lowered productivity. So, share those challenges, but only a handful of times per year, to avoid being seen as an emotional drain. And of course, your boss or client, being a nice guy, would never admit that it is an emotional drain. But even for the nicest guys, that’s how it always feels.
