Q. My boss cannot write. His spelling is horrible, his grammar is quite bad and he doesn't feel it's important (he's 36). We're a small company and he reports directly to our CEO and going to her is not ideal. Any ideas? We feel he represents the rest of us, as well as our organization, poorly with his written communication! Does this not matter in today's workplace?
A. Communication skills do matter in today's workplace and having the ability to write well, speak well and present to small and large groups can have a significant impact on landing a job. Professional advancement can be dependent on the development of effective communication skills. Hiring managers are eager to see demonstrated ability in these soft skills for potential employees and organizations do benefit from effective communication.
It seems like there are other skills more important than grammar and writing in your organization; at least in your boss's role and to the CEO. Often leadership finds communication issues hard to address. Most people do not want to correct errors in grammar made by others to avoid embarrassment. You are correct though, that bad grammar or unprofessional speech reflects poorly on the organization.
If your goal is to support your boss and organization, you can have a private conversation with him. Perhaps say, "You have lots of great skills, but writing is not one that shows up at the top. My writing skills are strong and I’d like to volunteer to proof read and edit your materials. Your message is great and with a little editing, I know it would make everything you have to say that much stronger.” When an offer to help comes with support and not negative judgment, most people respond well. Hopefully your manager will.
B. Having a conversation with your CEO about a developmental opportunity focused on improving your managers communication skills is also a reasonable option. The CEO may not recognize the impact your boss's lack of skilled communication is having on morale, or the public perception of the organization. Offering potential solutions rather than the frustration you expressed, will encourage the CEO to offer her support to improving the situation.
Your boss's age may indicate a generational issue. If he becomes convinced of the long term value of improving his skills, his willingness to invest time and energy into improving his skills may improve. Communication skills can be improved and the organization's recognition of the value of good communication through coaching, editing and encouragement can have a positive impact.