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.

  • 2
    what type of risks are you talking about? and how big is the company?
    – MattR
    Commented Mar 22, 2019 at 19:21
  • 1
    @MattR, we invest (time, money, resources) in projects that are highly improbable to ever be successful. Mainly, it's about sunk costs.
    – BigMadAndy
    Commented Mar 22, 2019 at 19:43
  • 4
    To the close voters: How is this unclear what you're asking?
    – rath
    Commented Mar 22, 2019 at 19:50
  • 1
    so, specifically you want your bosses to be happy with you, but don't particularly care if the company thrives, as long as bosses remain happy?
    – Ben Barden
    Commented Mar 22, 2019 at 20:18
  • 1
    @BenBarden, if I didn't care about the company, I would shut up and not bring up risks at all, wouldn't I? Not sure if I'm getting old or some of the comments are very strange this time :)
    – BigMadAndy
    Commented Mar 22, 2019 at 20:21

3 Answers 3


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.

  • Downvoters: I'd be happy to know how I can improve this question.
    – rath
    Commented Mar 22, 2019 at 20:16

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.

  • 1
    Of course businesses take risks all the time. But some risks make sense and some don't. To use an analogy: driving your car you probably increases your risk of having an accident. Most people accept this risk. Driving your car 150 km/h and after drinking three shots you take a stupid risk. Stupid risks are stupid and are to be avoided. Here we are talking about the latter kind of risks.
    – BigMadAndy
    Commented Mar 22, 2019 at 20:08

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