Csdrhrt

I work in a field in which too much optimism can cause huge costs (sunk costs in terms of money, time, resources).

My boss tends to be too optimistic and disregard the risks I signal and recommendations against something while taking decisions.

At the same time, my efforts to stress verbally and/or in writing that I'm "against some decision because of A, B and C" is treated as CYA (cover your ass), uncooperative behavior.

The bad decisions have an impact on the key performance indicators (KPIs) I'm responsible for.

What is the best strategy here? My goal is to secure my bosses are happy with me basically, since I know that's the only way I can progress in my career.

If your boss is not receptive to negative feedback, you may have to work around that. Here are some ideas for that:

Could you make the decision instead?

If your boss' decisions primarily affect your KPIs, it might make sense to transfer decision authority to you. You might be able to sell this as "taking care of the details so he can focus on the strategic vision" or whatever it is he likes to do.

(Often visionary people are bad at details, so offering to take care of the details allows both of you to play on your strengths)

Could you give positive feedback instead?

If your boss is deciding between A and B, and A sucks, you could say that B is a great idea, and then proceed to list all the advantages that B has over A, rather than the disadvantages A has when compared to B.

Could you filter bad options before your boss sees them?

If your boss is routinely contemplating poor choices, the process that generates these choices might be at fault. Perhaps you can become part of that process, and ensure that better options are presented?

Could you give the negative feedback earlier, when options are more malleable?

The more time people have invested in an option, they less willing they are to drop it, and the more loudly you have to speak up to stop the disaster. If you catch your boss before the bad option has taken root, mild negative feedback can redirect initiatives that will be neigh impossible to redirect once they have gathered momentum and everyone who has associated himself with the initiative would lose face in admitting that the idea sucks after all.

Your boss wants to be surrounded by yes-men. Nothing you can do about that other than change bosses.

Maybe there's something in the way you express yourself that paints a target on your back. You write:

against some decision because of A, B and C

You're taking a position against your bosses decision. You don't want that. You wanna be totally onboard, but keep an eye out for the risk caused by A, B, and possibly C. You still highlight the risk but you're no longer uncooperative.

Also, maybe pick your battles more wisely. Let the small things slide so you gain some personal rapport, and use this "capital" to go against the more expensive problems.

Is it possible for you to mention the risks in an objective way where you focus on the hard facts and play down your feelings? Maybe state it in a way that makes it easy for everyone to grasp the costs and make decisions based on that. If you can imagine ways to mitigate the risks you identified, include those thoughts as well to help the intellectual discussion.

Businesses take risks all the time. Sometimes they are stupid risks with small possible upside, sometimes they are necessary risks to reach any kind of progress.

Don't simply point out risks, offer possible solutions and make it a dialogue. Rather than telling your boss X has risks or you recommend against X you should attempt to start an open conversation instead. You can start off with something like this:

Hey boss, regarding X I was thinking about factor Y and how that could affect X, what are your thoughts on this?

You can then explain to him your thoughts on X and propose alternatives.

It's very easy to shoot down ideas and point out flaws in anything. If you want your boss to start listening to you then offer solutions to these problems.

I think you need to learn to accept your supervisor's decisions. Individuals are allowed to disagree while a decision is being made, but that once a decision has been made, everybody must commit to it. This is important; managers need people that challenge them when they are wrong on important stuff, but once a decision is made, it is your job to help and support them. I think this is the best way to long term rewarding relationships with supervisors.