It’s difficult to have difficult conversations, by definition (tautologically).
Now play along with me for a moment: let’s say it’s inevitable that hard talks will happen. No project, no client work, no relationship is so smooth that there isn’t a bump. The entire genre of “romantic comedies” is based around having hard talks in relationships and avoiding them until it’s too late.
So, given this assumption that bumps (including major ones at that) will happen, you have two choices: deal with them when it’s a big bump or deal with them when it’s a small bump.
My thesis is that it is always easier to deal with problems when the bumps are tiny, as opposed to when they’ve grown so big. Thus, it makes sense to always have difficult conversations as early as possible.
Although we don’t think about it much, this point largely seems to be a tautology. Anything difficult is easier to solve when it’s a manageable size than when it’s an unmanageable size because that which is unmanageable is unmanageable. Perhaps even unimaginable.
The key to doing so is to pay attention to yellow flags, so you deal with them as soon as they appear.
There is no master list of yellow flags and indeed, what may be a yellow flag to one person may be “oh that’s just how business is done” to someone else. So, you need to develop this smell on your own. A useful way to develop it is to track it.
A few yellow flags I’ve learned to look out for, which may or may not be yellow flags to you, but pay attention in case they are:
- Serious hesitation to document what is spoken.
- Serious hesitation to share details of work.
- Constant mistakes, but consistently in favor of the other person, not you (Oops!).
- Holds himself to a different standard than he holds you (say, he expects you to work 24/7 while he’s hanging out partying).
Remember, these are just some patterns I’ve noticed that may or may not apply to your observations. Build your own list.
And of course, remember a yellow flag is NOT a red flag. It doesn’t mean anything is wrong. Each item, on its own, almost always has a rational, logical explanation. Taken together, a series of yellow flags is likely to blow up at some point.
And for me, at least, if I expect something to explode, I’d rather it explodes today than one year from today, so I can start building something from a stronger foundation as quickly as possible.
