Train Your Boss

by W.E. Caswell


It is safe to say that most supervisors—or other titled people who oversee staff—have not mastered the art and skill of managing. It follows that most employees under those bosses are managed inadequately. The odds are that you are among those ‘mismanaged’ staff—and if so, you probably know it, or at least you may often sense it.

So, what can you do about a woeful supervisory predicament? We recommend that you immediately stop criticizing your boss and take control of the situation by training your boss how to manage. There is only one caveat: never allow your boss to know that you are doing the training; never let anyone know.

From a human behavioral perspective, you need to follow a process that involves taking responsibility for your boss’ lack of action or direction. It does not involve manipulating but it does involve being proactive and setting boundaries. Such boss training should be done discretely and always you should avoid taking credit for the results achieved—bask in the enjoyment of a better workplace for yourself but do not indulge for one second in glory. Your own performance will improve; that should be reward enough.

 Step 1: Clean up your own act first

You may want to improve your boss, but what about your own grade? Check it out by reviewing the steps that follow. Make sure you put these in place as a habit for your treatment of others who report to you or are at least putting them in place before you begin on your boss.

Step 2: Learn to write inoffensively

Strident memos rarely get the results intended; instead they often engender a negative reaction. Some quick avoidance rules for your emails are:

  1. Remove the word ‘you’; it is accusatory.
  2. Remove emotional or stressing words; they’re subtle but a dime a dozen. (“I have frequently noticed this” should be “I have noticed this”.)
  3. Use facts, numerical items, not generalities. Instead of “It is forever breaking down” say
  4. “In the past week, it has broken down three times.” Also, this is a chance to illustrate another example of avoiding emotional stressing word such as “alone”. “In the past week alone, it has broken down three times”. Ugh!
  5. Never, ever, exaggerate.
  6. Don’t use others to justify your case against the individual. Never: “Gary has noticed this habit of yours as well.”
  7. Wait 24 hours before you send the memo.
  8. Have a peer read it before you send it.
  9. The truth is not necessarily ‘good for you’. Do not be a sanctimonious truth-monger. Instead deal with issues in a non-hurtful way.
  10. Generalize away from an individual to a group. “He always..” becomes: “ I find that…”
  11. Take blame even when you know you are not to blame. “Perhaps, I might do this myself as well”.
  12. Avoid ‘always’, ‘never’, etc.

Remember very little is achieved by putting someone down, intentionally or non-intentionally. What you usually want to do in a memo is to engineer a successful change of behavior. You are not trying to make yourself look better but to make the situation improve for everyone. Avoid defensiveness, justification, etc. Stick to the facts.

Step 3: Set up weekly meetings

You need to meet weekly with your boss. In fact, the whole team should meet once a week with your boss. However, trying to set up a meeting for yourself will be quite enough of a challenge. Tell your boss that in order to do your job, you need to touch base once a week with your superior. It should be an hour-long meeting, but if a half hour or 15 minutes is all you can get, that is infinitely better than zero time. Once the idea of a meeting is grudgingly acknowledged (or positively acknowledged) suggest a regular time to do it: “Friday noontime at 12:30”. Send your boss an agenda for the meeting at least one full day before the meeting. Don’t let trips or holidays create an excuse to avoid the meetings; set an alternative time for such circumstances; it could even be a telephone meeting.

Step 4: Set up your performance reviews

Set up quarterly performance reviews for yourself. They are far more effective than annual reviews and easier to manage.

Step 5: Get your boss to follow up decisions

After each meeting with your boss, send a little memo saying: “Charlie, this is my understanding of our meeting yesterday.” Then list each action item, who was to do it and by when. “It was agreed that I would investigate the Paris show costs and get back to you by next Tuesday, the 26th.” Finally, you might add (1) a disclaimer and (2) your own verification: (1) “If I have misunderstood anything, please let me know.” (2) “I will assume in the absence of your comments to the contrary within the next two days, that I have captured the essence of our Monday meeting.”

Step 6: Follow up your boss’ action list

When one (or more) of the action items of your boss related to you is not done, send a polite prompt. Blame yourself. Offer assistance. “Charlie, my understanding is that you would provide me the client lists by Wednesday the 11th. Did I get my wires crossed? Is there something you would like me to do to assist in this endeavor?”

Step 7: Define your own outcomes

You need to know what you are supposed to deliver and by when. This avoids the boss fussing over the details of the ‘how’ you do it but rather concentrates on the ‘results’ of what you do.

Step 8: Deal with last-minute hijacking

If your boss drops a load on you at what seems to be an inappropriate moment, disrupts a meeting, asks you to stay late, etc., of course you must comply to deal with an emergency. However, if this hijacking of your priorities with the boss’ agenda occurs frequently, there is an organizational or respect-related problem, which you must address. Obviously, you have to be extremely delicate in the manner in which you begin the training. “Three times this week, I have had to defer some of my work to address sudden issues. I am confused about my other priorities. Can you help me sort them out?” Sticking to the facts initially, you follow on to let your boss know that there has been a negative consequence to you of these

last-minute intrusions. Then you get your superior involved in the solution, reinforcing the point of the stress they are adding to your life. That alone might be enough to have your boss think twice before dropping a bomb on you again. If not, round two might be, as you cope with this new emergency: “Is there something I might do for you now so that you will not be caught by surprise by an event like this next week?” A boss, who does not accept such a helpful suggestion, will at least (probably) take a second look at the organizational aspect of that job. Keep up the friendly, thoughtful pressure, using the most positive and pleasant language you can muster. Eventually things will sort themselves out.

IAAP works with the best trainers in the industry to ensure you have relevant, engaging, practical content at your fingertips. This blog is written by a speaker with a program in the IAAP Approved Programs database. Search by name or keyword to find their contact information and book them for your Branch or Region event.

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