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What to Say When Your Employee Makes a Mistake

Jeffrey was the CEO of a hedge fund, and he was upset about some poor trades that Tom, one of his portfolio managers, made. He called Tom into his office. (This is a real example with real people, but I’ve changed their names.)

“Those trades were a terrible idea! What were you thinking?” Jeffrey asked Tom.

The conversation quickly went downhill. With that first question, it would have been hard for it to go any other way.

Why was it a bad way to start? “What were you thinking?” is a past-focused question. When Tom explains his thinking to Jeffrey, he’ll reinforce his mistake and sound defensive because his thinking was problematic and led to poor results. He doesn’t necessarily think the same way now, of course.

Let’s play it out. Tom will explain why he made that trade, and Jeffrey will get angry at his poor judgment. Then they’ll both leave the conversation frustrated and disheartened (which is, predictably, exactly what happened).

What could Jeffrey have done differently? A better choice would have been to avoid talking about the past and, instead, ask Tom about the future: “How will you do it differently next time?”

This kind of future-focused question allows Tom to acknowledge his mistake and demonstrate his learning. It will reinforce both people’s confidence in Tom’s abilities while also giving Jeffrey the opportunity to point out any further problematic patterns in Tom’s thinking — in a way that could help Tom make better decisions in the future instead of just making him feel bad in the present.

Another advantage of a future-focused question? It’s faster and more reliable because you’re removing one step in the learning process. Rather than going over your mistake and then (hopefully) applying the learning to a future situation, you go straight to the application.

Why don’t we all do this intuitively? Because, in the moment, we’re not feeling it. What we’re feeling is angry, and probably a little scared, frustrated, and annoyed. And then we blurt out, “What were you thinking?”

We do it in order to make ourselves feel better. We ask that past-focused angry question because our emotional overload in the situation is simply too much. We burst. But that’s not great leadership, and it’s not great communication. When we lead and communicate, we’re not doing it for ourselves; we’re doing it to help others improve.

Which means we need to tolerate our difficult emotions so they don’t overwhelm us, so they don’t get in the way of our intended impact on others.

Emotional courage is the willingness to tolerate all feelings. It’s entirely developable, and developing it increases your ability to lead effectively, get business results, communicate in a way that inspires others, and make the impact you’re trying to make. How do I know? My company, Bregman Partners, measured those changes in people who increased their emotional courage at our Leadership Intensive.

It’s one thing to know how to communicate in a way that inspires others and brings out their best. It’s another to actually do it, in the heat of the moment, when your emotions are high.

Here are a few keys to making it happen:

  1. When you feel emotional, be suspicious of any instinctive reaction. Before saying or doing anything, pause and take a breath.
  2. Pose a silent question to yourself: What is the outcome you want your next move to achieve? In other words, what do you want to happen as a result of your communication? Make sure you get to a real outcome. If your answer is that you want the other person to feel bad, ask yourself why. What are you hoping will result from their feeling bad? If your hopeful response is that they will make better decisions next time, then that is the outcome you’re going for. (The feeling-bad part is how you think they will get there — but you’re wrong.)
  3. Decide what you will do or say that will most likely lead to your ultimate outcome. Often, what you’ll find is the conversation that holds the greatest likelihood of getting to your ultimate outcome is about the future, not the past.

If you’re a leader, and you’re dissatisfied with someone’s performance, take that breath, identify the outcome you want, and then ask them what they plan to do in the future.

And if you’re Tom? If you’ve made a mistake and your manager asks you Jeffrey’s ill-advised question: “What were you thinking?

As I mentioned, it would be hard for the conversation to go well. Hard, but not impossible.

Even though your manager is asking about the past, it’s your turn to take that breath and ask yourself what outcome you want. Then, your best move is to ignore the question asked and, instead, answer the question that wasn’t asked: the future-focused one. “What was I thinking?” you could say. “Clearly, not the right things. But here’s what I would do differently next time…”


Peter Bregman is the CEO of Bregman Partners, a company that helps successful people become better leaders, create more effective teams, and inspire their organizations to produce great results. Best-selling author of 18 Minutes, his most recent book is Leading with Emotional Courage. He is also the host of the Bregman Leadership Podcast. To identify your leadership gap, take Peter’s free assessment.

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How to Stop Obsessing Over Your Mistakes

Do you ever find yourself endlessly mentally replaying situations in which you wish you’d performed differently? You wish you hadn’t said that dumb thing. You wish you’d volunteered for that project that’s now winning accolades. You wish you’d spoken up. You wish you hadn’t dropped the ball with that potential client.

Overthinking in this way is called rumination. While we worry about what might occur in the future, we ruminate about events that have already happened. A ruminative reaction to an event often triggers memories of similar situations from the past and an unproductive focus on the gap between the real and ideal self. Prompted by this one event, you begin to chastise yourself for not being more of something…organized, ambitious, smart, disciplined, or charismatic.

Rumination isn’t just unpleasant. It’s closely linked to poor problem-solving, anxiety, and depression. The good news is that there are effective solutions for breaking yourself out of this rut, and they’re simpler than you might think.

Identify your most common triggers. You can’t quell rumination without noticing that you’re doing it, but people aren’t always able to spot it in themselves. A great way to get better at this is to think about what has triggered you in the past. Your list might look something like:

  • Collaborating with people I don’t yet trust
  • Being around people who seem smarter or more ambitious
  • Taking a step up in my career
  • Making major money decisions

Notice if the dominant pattern of your rumination is blaming yourself or blaming others. Most heavy ruminators lean towards one or the other of these.

Get psychological distance. Next, you need to put some psychological distance between you and the things you ruminate about. For instance, you might feel concerned about how you’re perceived by people who have no impact on your success, get hung up about very small amounts of money, or see yourself as an underachiever despite the fact that objectively you’re doing very well. One way to start to get this distance is by labeling what’s running through your head as thoughts and feelings, a tactic described in this article on emotional agility. So instead of saying “I’m inadequate,” you might say, “I’m feeling like I’m inadequate.” You can even be more light-hearted about it: “Oh, that’s just my ruminating mind overheating again.”

Recognizing the absurdity in some of your reactions can also help you take them less seriously. Look for any subtle entitlement or self-absorption hidden in your ruminations. Do you expect things to always go your way? Do you tend to believe people are scrutinizing you when, in reality, they’re probably thinking about themselves? Do you spend time comparing yourself to business superstars or celebrities? Entitlement and personalizing can indicate that you tend to think the world revolves around you. If applicable, try to see the irony in being both narcissistic and insecure, rather than viewing it as an indictment on your character. You can even try imagining an ultra-neurotic TV character version of yourself. Not every rumination topic is appropriate for this strategy but catch any that are.

Distinguish between ruminating and problem solving. Occasionally you might have a useful insight while ruminating, but mostly it’s avoidance coping. Generally, the more people ruminate, the less effective they are at problem solving. Either they don’t think of solutions or don’t pursue them quickly or effectively. For instance, one study showed that women who were heavy ruminators took over a month longer to seek medical care after finding a breast lump. To shift from rumination to improvement mode, ask yourself, “What’s the best choice right now, given the reality of the situation?” Start by taking one step, even if it’s not the most perfect or comprehensive thing you could do. This strategy is particularly relevant for perfectionists. If you’re ruminating about a mistake you’ve made, adopt a strategy that will lessen the likelihood of it happening again.

Train your brain to become non-stick. As soon as you notice you’re ruminating, try to distract yourself for a few minutes. Engage in an activity that’s short and mentally absorbing but not extraordinarily difficult, like spending 10 minutes filling out an expense report. The activity you pick should be one that requires you to concentrate. In some situations, you might be able to just refocus your attention on what you’re supposed to be doing. You might think: “How could something so simple help with my complex, emotional problem?” But this technique can be surprisingly effective.

Physical activity, such as jogging or walking, can also calm a mind that’s prone to rumination. Meditation or yoga can be especially helpful for protecting yourself from sticky thoughts and learning not to over-engage with them. These practices ask you to notice when your mind has wandered off to the past or future and bring it back to what’s happening in the present (often your breathing or other sensations in your body or surroundings.)  This is exactly the skill you need for coping with moments of rumination.

Check your thinking for errors. Sometimes rumination is triggered by cognitive errors. The catch-22 is that you’re not likely to be very good at detecting distorted thinking when you’re ruminating, since it clouds thinking. The solution is to develop a good understanding of your typical thinking errors, over time, in calm moments so that you’re still able to recognize them when you’re feeling heightened emotions. Here’s a personal example: I’ll often read a work-related email and zone in on one or two sentences that irritate or upset me and then misinterpret the overall tone of the message as demanding or dismissive. But, because I’m aware of this pattern, I’ve learned to not ruminate over my initial impressions. Instead, I read the email again after a day’s cool down, and usually see that I had a biased impression of it.

Other common cognitive errors include setting too-high self-expectations, misinterpreting others’ expectations of you, underestimating the extent to which other smart people struggle with what’s troubling you, and making mountains out of molehills. If you’re ruminating about someone else’s behavior and attributing a cause to that behavior, at least entertain the idea that your explanation is wrong and try to accept that you might never know the truth. Recognizing that we often won’t understand the reasons for someone else’s behavior is a hugely important skill in reducing rumination.

Rumination is a widespread problem. Before you can break out of it, you need to become more aware of when you’re doing it and have resistance strategies ready to go. This takes time and effort. But it’s important — for your mental health and productivity — to try to nip it in the bud. So, before you go deep into your next “would have, should have, could have” spiral, give one or more of these ideas a go.


Alice Boyes, PhD is a former clinical psychologist turned writer and is author of The Healthy Mind Toolkit and The Anxiety Toolkit.


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