How to Approach the Boss

- Tom Werner

From time to time each of us experiences a difficult situation in which we feel compelled to convey our concerns to management. Sometimes a verbal approach is sufficient; other times, a written note is most effective. Either way, the effort you devote to crafting your message is a critical factor in determining how well it will be received and what type of action might result. This is especially true when the situation at hand is personal, as your emotional involvement is often apparent in the communication. Where a well-crafted memo portrays you in a positive light and provides the best chances for progressive action, an ill-considered message won’t get much constructive attention, and is more likely to have adverse consequences on your reputation and career.  With all of this in mind, I’ve put together a few thoughts on how best to write a message to senior management.

Consider these points when you’re beginning to write a note of concern:

Stay on the topic: The situation at hand may be just one of many issues you’ve witnessed in your tenure at Your Company. Don’t bring them all up at once; they’ll dilute your message and reduce the gravity with which Management considers your key point. Make sure every sentence of your communication builds toward your theme.

Provide support: The more objective evidence you provide, the more credible your case will appear. Simple statements without support (e.g. “I am working harder than anyone on my team.”) doesn’t help management understand your thought process. Don’t speak for others unless they explicitly approve: Your colleagues will not approve of your dragging them into a situation with a phrase like, “Billy Bob thinks you’re a horrible manager, too.”

Exception: If you are witness to something illegal or against company policy (such as sexual harassment or abusive behavior), you are encouraged to bring it forward even if the victim doesn’t do so him/herself. Don’t make threats: If you say something like “If you don’t act, I might accidentally make the system crash.” Murphy’s law says that that will be the night when the system crashes unexpectedly, and your actions will look criminal.

Don’t make ultimatums: Saying “If you don’t put a foosball table in here, I’m quitting immediately.” is counterproductive. First, you’ve played a card that you didn’t need to play yet. Someday, conditions may cause you to quit. That’s unfortunate, but to bring that eventuality up too early commits you to a course of action you might regret.  Also, you have now thrown down the gauntlet to management, and the risk of management appearing to be coerced might force them to rule against you….just because.

Don’t ‘flame’ anyone: Even though you are positive that a person’s incompetence or inaction would prevent meaningful action, don’t try to point that out in your note. Saying “I am writing to you, Mr. AVP, because I am sure that taking this issue to my Director would be useless, as he never shows an interest in anyone and only inflames the situation.” may be exactly what you feel, but you would be much better off writing, “Mr. AVP, I am bringing this directly to your attention because I feel that someone of your level is required to effect the decisive action that I believe is warranted.

Assume the best of everyone: Even if you think someone is (e.g.) lazy or malicious, there’s no point in saying it. If it’s true, it’ll become readily apparent in its own way. If it isn’t, you’ve slandered someone. Either way, your reputation will be tarnished. Saying “Despite his efforts, Manager Billy Bob has been unable to rectify the situation.” is better than “Billy Bob hasn’t done a thing about this.” Billy Bob’s supervisor will ascertain fairly quickly whether Billy Bob has been doing all that is necessary. Understand that you might be wrong: Remember that your position doesn’t always give the ability to see all of the parts of the puzzle. Even if your supervisor can see all of the parts, he or she may be prohibited from sharing them with you. Include your Management Chain: If you think your message must first be directed to your Vice President, have the courtesy to copy your AVP, Director, and Manager in the communication. To the extent possible, write your note to convey that all of these people are part of the team that will craft a satisfactory solution. Note that I’m not suggesting that you have to work your problem through your Manager, then Director, then AVP; sometimes that’s expedient, sometimes not. Just don’t get your Manager blindsided when the AVP comes down to say “What’s going on with Billy Bob?”

Exception: If your supervisors are the problem and you desire some confidentiality from them, then you can circumvent layers of management as necessary.

Avoid “Collateral Damage”: Too often, emotion or a desire to be clever spills into the communication with phrases like “Failure to act will be the stupidest move since some moron decided that lavender and teal would be the new Your Company colors.” The reference has nothing to do with your specific problem, and you’ve offended someone who might very well be reading your memo. Check spelling, use proper grammar, and proof-read your work: Nothing undermines your case or portrays you in a bad light more than basic errors in spelling or grammar, unclear sentences, or the omission of a key word such as “not”.

Let someone else proof-read your message: Find a manager or colleague that you can trust, and let them take a look at your note. They can often offer a perspective that you can’t see yourself. If you don’t feel comfortable showing your note to anyone at work, consider a friend or family member outside Your Company. OK, that’s all I can think of. You might read this and think I am trying to suppress your expression. That’s not the intent.

My purpose here is to help you convey your thoughts in as constructive a manner as possible. I’ve witnessed each of the mistakes described above in the last few years. A well-presented position shows you in a favorable, professional light that will be to your credit – even if the situation at hand is not resolved to your satisfaction.