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I work as a designer for a software company, and work directly with developers on their newest and most important product. I am gaining a very good understanding of the software and how it works. However, the CEO of the company is not very technical and doesn't understand the product very well. He often writes marketing content or has marketing ideas that are bad or incorrect.

I'm having a hard time knowing when I should voice my opinion about marketing/design decisions and when I should just do what he wants. Right now, we have contracted a marketing company to assist us, but it is clear that they are simply doing what the CEO wants and only giving advice/opinions when he asks for it.

Should I follow the example of the marketing company and aim to keep the CEO happy, even if I know it will not look right or demonstrate the product well? Should I bother trying to correct his misunderstandings of the product?

Is it my responsibility as a designer to say when something looks bad, or when marketing content is incorrect, or is my opinion better offered only when requested? I am lucky to have a job right now, and I don't want to risk stepping beyond what is acceptable feedback

Niahc
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    Never just criticize. Offer an alternative and explain why you think it's enough better to be important. If the idea is turned down, then unless it's something on which you'd be willing to bet double-or-nothing on your next raise (or more), let it go until next time. – keshlam Feb 08 '16 at 22:33
  • I can be very tactful when offering my opinion. But really, no one likes when someone disagrees, no matter how reasonable and gentle it is. But they might expect me to have some opinions as a designer, or catch when something might damage their reputation. I can either do what he wants, and possibly lose credibility, or I could warn him before (nicely) and cause friction at first, but ultimately build up trust. – Niahc Feb 08 '16 at 22:43
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    The time to offer input is ALWAYS before the decision has been made and announced publicly. The higher the person making the announcement, the more critical it is to follow this rule. If you want to be involved up front in the design process, ask to be involved before things are finalized. And remember, criticize privately not publicly. – HLGEM Feb 08 '16 at 22:49
  • Do your materials go through any sort of review where people can say "Hey, this doesn't work and this is why"? Preferably before someone who matters sees something horrendous. – CKM Feb 08 '16 at 22:59
  • The CEO never involves the people that should be involved in marketing decisions. That gives me the impression that the CEO is trying to avoid negativity or being shot down. I may be reaching too deep but I think the CEO is insecure about his lack of technical skills/knowledge and avoids people who might make him feel ignorant. Still, at some point he needs to be steered in the right direction. But I'm not sure if this is my job. I guess it is a matter of helping the company do well vs. making the CEO happy. – Niahc Feb 08 '16 at 23:21
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    When in doubt, update your résumé. – Lars Viklund Feb 09 '16 at 16:15

4 Answers4

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Should I follow the example of the marketing company and aim to keep the CEO happy, even if I know it will not look right or demonstrate the product well? Should I bother trying to correct his misunderstandings of the product?

Is it my responsibility as a designer to say when something looks bad, or when marketing content is incorrect, or is my opinion better offered only when requested?

Hmm, tough call. And I suspect it's very context-specific.

I've worked for CEOs that really wanted honest feedback on pretty much everything. I had a good relationship with them, and they were the type that welcomed constructive criticism on everything from company policies, to the corporate website, to marketing materials. (None of these were within the purview of my job at the time). They were the types of CEOs that made it safe to be honest.

And I've also worked for CEOs (and others) that clearly did not want honest feedback. They wanted yes-men, and they got only yes-men over time. It was clear that frankness was not a good career move in those companies.

If you don't already have enough insight into your CEO's personality, then tread carefully at first. See how others talk. Perhaps informally offer an opinion on something not overly significant and gauge the reaction. Then you'll get a better sense if it is safe to go further, or if you are better off holding your tongue.

Joe Strazzere
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    You won't know unless you voice your opinion. However I think it depends on the context you heard it from. If he had a company-wide announcement and suddenly you appear at his office saying it's a bad idea, then well that's going to look bad for you no matter what kind of CEO you have. However if you have a personal friendship with the CEO, then mentioning a bad idea might be feasible. – Dan Feb 09 '16 at 14:54
  • I guess this answers my question. I've been talking with other employees, and they struggle with him a lot. His personality is a bit odd, and the company has a 300% turnover rate. We get along well so far, but likely because I've been extremely careful with his ego. I think its best for me to offer my opinion on unimportant matters, and leave him to make mistakes that involve his lack of knowledge or bad ideas. – Niahc Feb 09 '16 at 17:26
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    @Niahc You might also frame it in terms of how much money you're going to lose if you go with his idea. If you do that tactfully, you might break through to him and begin to earn his trust. – BobRodes Feb 10 '16 at 07:06
  • @JoeStrazzere: At 300% turnover rate, the answer is either "because he is lucky" or "because he is unlucky" :-) – gnasher729 Feb 10 '16 at 09:17
  • Its a smaller company (20 employees currently). The turnover rate is a bit inflated because the CEO went through at least 8 personal assistants in the last year. I don't work very often with him directly, and this job is otherwise quite enjoyable. I'd like to learn the art of being taken seriously as a designer, but I end up spending a lot of time on projects I know will look bad or mislead customers. It doesn't help me gain credibility as a designer, but then again, at least I am an employed designer. – Niahc Feb 10 '16 at 17:53
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It looks like you need to clarify your role. Maybe it's a good moment to ask your boss: "What is expected of me?" There are at least two options:

a. "Stick to your work next to the developers." Then do your best there, do not mind what happens outside this role. Should you provide great value, the CEO will see it and you will be invited to take more responsibility in the marketing area. Then you can challenge bad marketing and poor suppliers.

b. "Please contribute to whatever is connected to marketing/design." In this case you should carefully pick the places where you can make a difference, and focus on adding some value. For instance you can isolate some of the content your CEO has written, make a review, go to him and position your feedback: "I understand you are a busy person and I want to help. Here are some ways we can improve our [content example] and in the future I can write, review or refine those materials and bring them to you for confirmation." I would value such a colleague in my team.

You cannot ignore the scenario where there is no role, and they only need another headcount. I sincerely hope is not the case. Your role does not matter. You will feel this yourself and already be searching for a place where your role is clear and your contribution appreciated.

DcK
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I see this in small startup companies. In my experience there was the CEO and their inner circle, and they would brainstorm marketing ideas and get riled up, then have staff drop everything and hastily execute their ideas, whether they were awful or not. Best thing to do was sit back and let them do their schemes, because 95% of the time they crashed and burned because the "inner circle" had zero technically savvy people. IMO, your opinion is best on request, but there's a good chance your suggestions don't go through (just from my experience w/ a CEO who acted similarly).

CKM
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I would tell the CEO straight out if I thought he/she was making a mistake, but only in my field of expertise. That's what I'm paid for, solutions that work.

If I have a marketing opinion, but I'm not asked to present one, not employed for my marketing skills, and/or not a marketing expert, then I would keep it to myself unless asked. And just do the jobs I'm tasked with.

Just because you think the CEO is making a mistake doesn't mean they are or that they don't have very valid reasons (for them), I don't tell my people all the ins and outs of what I'm up to. I tell them what I want them to do. They may think they know better, but the reality is they work for me, not the other way around so I must be doing something right.

Kilisi
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