The One Technique to Get What You Want From Difficult People

By Kate Matsudaira

September 23, 2014   •   Fact checked by Dumb Little Man

Last week I was in Silicon Valley and I was meeting with one of my consulting clients, a CTO at a high growth startup. During our conversation, we started talking about one of his engineering managers. He was struggling to manage this fellow, since every time they were trying to make a decision (green-lighting a new feature, adjusting their strategy, etc.) this manager reacted with resistance.

It didn’t matter what the decision was; it seemed like he always had an objection.

Luckily, I was able to help. How? Well, I know a lot about this kind of difficult behavior firsthand, because I used to be that guy.

As engineers we are taught to look for bottlenecks. When building software the ability to think through potential failures, faults and issues is an asset that actually helps us write better code. A lot of my early success came from my ability to spot potential faults and tell people about them, before they became huge roadblocks.

In fact, lots of roles encourage this kind of thinking; the people who can spot potential issues and avoid them are the ones who get promoted.

The problem, though, is that being the person that always points out problems doesn’t necessarily make you a valued member of the team. You can come off as someone that is difficult to work with or not a team player.

Of course, telling someone this can be really hard. No one who is a jerk at work acts that way just to be a jerk; they think they are helping or doing what needs to be done.

Many people don’t see the affect their constant dissension has on those around them. But if they don’t understand the problems or see why they should change, then they won’t be motivated to make the changes (and you can’t force people to change).

Thankfully, if you have to work with someone like you can change the outcome by changing your approach.

Difficult people want to add value too (just like you)

When someone responds to a statement with a disagreement or mismatch it isn’t necessarily because they want to be disagreeable. In fact, most of the time people react in this way is because they want to add value. They want to contribute to the conversation because (like all of us) they want to feel important.

For example, if you start the conversation with “We should move forward with Project X”, if a person responds by saying “I agree,” then they are essentially adding nothing to the conversation. On the other hand, if they respond by saying “But isn’t Project X going to be expensive?” they are adding details to the conversation that they think make them appear smart and thoughtful.

For many people this is an instinctive defense than a thought-out response. It is so ingrained in the nature of conversation that many people do it without realizing it.

There are several forms of this type of disagreement:

1. Contradictions: This one is exactly like it sounds, and is a reflexive response to your statement. For example, you might say, “I’ve thought through our roadmap and we should do project B before project A.” They would contradict you with something like “I really don’t think we should consider project B right now.”

2. One Upping: This is when the other person feels like need to out do other person, much like children might do during recess in a schoolyard. An example of this would be if you were to say “That outage took a toll on our team they had to come into work all of Saturday” and they were to respond with “Well, our team had it even worse, they had to work all weekend.” Working together shouldn’t be a contest, but sometimes it seems like conversations lead in that direction.

3. Additional Clarifications: These are similar to the first example, where a person just wants to add value but ends up shutting down the conversation. For example, if you were to say, “We are behind over 100 tickets and need to scale up our customer service,” and they were to respond with additional clarification saying, “Well, actually we are only behind 85 tickets.” Even though the point still stands about the ticket backlog, the other person has undermined your original statement casting the conversation in a negative light.

4. I know that already. Have you ever told someone something you thought to be helpful and they shut down the conversation right away? “Yes, I know that already.” This happens a lot when the other party lets their feelings of inadequacy enter the conversation. I find this kind of disagreement occurs a lot around performance reviews, or feedback cycles. People will react reflexively shutting down the conversation in order to protect their own feelings. These people aren’t trying to create problems, but they just want to be seen as a credible professional.

These responses can shut down the conversation or make things tense and uncomfortable.

But you don’t just have to avoid or ignore these kinds of conversations. You can change them. There is actually one amazingly simple step you can take to get around difficult people and actually make them less difficult to work with, now and in the future.

The power to change the conversation is in your hands.

Your one-step solution? Start asking more questions.

Instead of opening the conversation with a statement that can invite disagreement, start with a question instead. It can really be that easy.

Often, when difficult people disagree with you, it isn’t because they disagree with you. In fact, they may completely agree with you. But in an attempt to make themselves feel smart or important, they need to say something — and so they disagree.

It’s ridiculously easy to give them what you need, then, by simply allowing them to say something first. Give them the opportunity to feel important and smart, by letting them answer a question you pose, rather than making a statement they can disagree with.

By rephrasing your statement into question “Given the priorities, do you think we should start with Project B instead of Project A?” allows the person to add value with their reply.

By inviting them to the conversation, you give them a chance to contribute.

If you ask them for their opinion, you are giving them credibility, which actually reduces their need to disagree and resist. You are showing that you value their input by asking for it.

By asking questions you can also pique their curiosity, and people who are more curious and interested in what you have to say are a lot less likely to meet you with resistance and disagreement. They’re more likely to want to go along for this amazing ride where they can be a leader, rather than shoot down something they’re worried might be happening without them.

Really, it is that easy. If you are a leader, try asking more questions. This week in your meetings instead of leading with a statement, solicit opinions and invite conversation. You will be amazed at how this simple strategy can transform dissenters into team players.

Kate Matsudaira

Kate Matsudaira is an experienced technology leader. She has led teams at big companies (Amazon, Microsoft) and successful startups (Moz, Decide, Delve) before starting her own company, Popforms.

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