Dear Crucial Skills,

After a year and a half working with a new boss, I cannot get past the pure chaos in which decisions are made. This really came home to me this last week while we were on the road and the constant changes in the schedule and lack of planning made our team look unprofessional.

The person on the team who had planned everything with the boss worked hard to keep it from happening, but that person also found the boss difficult to make decisions with—even shopping for supplies turned into nightmare trips that lasted twice as long as necessary and left our budget and our schedule in shambles. I know enough to be glad not everyone has the same faults and she has some lovely qualities, however…

What can we do to keep routine decisions with the boss from turning into chaos?
Signed,

Concerned about Chaos

Dear Concerned,

It seems like you’ve got this pegged. You’ve identified the right person, the issues, and the conversation you need to have. Before I offer some advice, I’ll frame the issue to illustrate how some important pieces fit together.

Your challenge is like challenges faced by many of our readers, in multiple ways. First, this problem is tough because you need to talk to someone more powerful—your boss. We know that it is tough to talk to some bosses. The same challenge is faced by people needing to talk to a parent, or an in-law, or someone who is more senior, or more experienced, or more technical. The question is: how can we bring up this subject and have the outcome be positive? Second, there is a pattern. The problem has occurred in the past, multiple times even. Third, there are serious consequences. What makes it even more problematic is that the other person doesn’t seem to notice, or worse, to care.

When these three conditions exist, most people shy away from holding the conversation. Or they endure it until they act it out—through avoidance or gossip.

So what are some approaches that can help with situations like this?

First, start with heart. Some would get so annoyed with this that what they want is to have the boss stop, at any cost. So they explode, gush out their frustration, and hope for improvements. These people want a fix that gets rid of their problem—now. That comes across as selfish and short-term. If they got their motives clearer, if they focused on what they REALLY want for themselves, for colleagues, for the boss, and for relationships, they’d be more likely to take an approach that the boss saw as mutual and long-term rather than selfish and short-term. In this particular case, I think your motive is right; so you need to figure out what to say and how to say it. To help you get to more empathic approaches, consider asking the “humanizing question”: why would a reasonable, rational, decent person do this? What is your boss really trying to accomplish? Why would he or she make changes like this? What is his or her purpose? What bigger purposes are important here?

Next, consider the specific conversation you need to have. It seems that your conversation is not really about supplies and shopping; it’s about how we stay on schedule and keep to our budget. The question is: How can we make commitments that will help us do this and then talk to each other so that when there’s the risk of failure, we can catch it early and work together to fix it? I think that conversation is one that most bosses are willing to have. His or her specific behavior that caused the most recent problem can be added to this conversation in a way that is safe. For example, “During the last conference you went shopping and that caused the budget to go over. Can we talk about why that happened and what we could do next time to talk it over so that our schedule and budget are kept in tact?”

Remember, holding a crucial conversation is about preparing yourself well—your heart and your content—and then sharing, exploring, and responding. This keeps you agile and caring and attentive. There are only several options for possible outcomes: Your boss can agree; in this case you move to action. She can disagree; in this case you need to listen to her reasons—it’s possible that she can add meaning you hadn’t considered, and then you can move to action understanding all of the information now available. Your boss can get emotional; if this happens, you can step out of the content and make it safe using your Crucial Conversations skills. Finally, you can get emotional; if you do, you can catch yourself, ask for a time to come back and finish holding the conversation later, and then try again.

All of these alternatives are better than doing nothing. And all of the alternatives can be responded to well if you use your dialogue skills.

In conclusion, give the boss a break and bring up the topic in a safe way. You’ll be glad you did.

Best wishes,
Al