How to get what you want from difficult people

How to get what you want from difficult people

According to research by Dr. Brinkman and Kirschner in Dealing with People You Can’t Stand, there are challenging personality types that make our lives harder:

  • The Tank: Confrontational and angry.
  • The Sniper: Makes you look foolish.
  • The Grenade: Explodes into fury out of nowhere.
  • The Know-It-All: Authoritative and things must be their way.
  • The Whiner: Points out everything wrong in vague terms.

You might now be thinking of a person to put one of these labels on.

They could be a friend, co-worker, customer, or family member (circa that tense Thanksgiving of 2016).

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No matter what type of difficult personality they have, in the extreme you’ll experience what Robert I. Sutton, Professor of Management Science at the Stanford Engineering School, described in his graphically titled book:

“Encounters with rude, insulting, and demeaning people undermine others’ performance — including their decision-making skills, productivity, and creativity.”


Still, only about 10% of those you encounter are categorized as difficult, even if some days that number feels much larger.

How to handle difficult people

The other day I was standing behind a guy dressed in a tan suit at a coffee shop close to our Jotform offices.

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He was on his phone while simultaneously rambling off a complex drink order. Between the mumbles at the barista and the chatter into his wireless earbuds, I think all of us waiting in line knew what was going to happen next.

At the end of the bar, he picks up his coffee, takes a sip and immediately loses it over ‘the extra foam’ now destined to ruin his day.

Unkind words were exploded across the counter, leaving the barista temporarily frozen.

A Tank, confrontational and angry, was on the loose and he might be bloated later.

I watched as the barista listened to what he said, put his head down and redelivered the order to the man in just a few moments.

He handed the cup over kindly, watched for his approval, nodded, and then went to his next order as the man walked out the door still talking on his phone.

The barista had gotten what he wanted.

He kept his goal in mind and by listening and then taking action in the face of verbal accosting — he got him to leave — which was his exact desire.

How do we get what we want despite the “difficults”?

Whether you’re communicating with any difficult personality, being in the moment with challenging people is hard.

At Jotform, we have over 3.5 million users and some of our difficult users give us a difficult time almost every single day.

I wanted to put together a few guidelines I use that help me diffuse situations from handling our customer relations and also from managing our team of over 108 employees.

1. Listen and understand the end goal

At first, the barista froze to avoid conflict, but we’re all hard-wired like that.

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Every last one of our brains still defaults to fight-flight-freeze when something highly stressful or unsettling occurs. However, when a person is acting unreasonably right in front of you — being like the barista works perfectly.

He was able to not only move through this automatic response of fight-flight-freeze, but get clear on what he wanted and execute flawlessly.

Listening combined with intent to understand what is being sought, gives you the prime opportunity to end the interaction while achieving your goals.

The barista understood that no matter what the man said what he really wanted was to have his coffee the way he asked for it.

He listened past all the yelling to delineate how he could fix the situation while achieving his goal of watching him walk out the door. The feedback was harsh but this barista was a pro.

Now, we don’t hear much yelling at Jotform but we get challenging feedback online all the same.

Our forms are meant to help us and our customers meet their goals and mitigate these issues before they happen. However, difficult people show up in person and online to air their grievances.

2. Focus on what you can do something about

You may not be able to avoid what difficult people have to say but you have control over what you do, and more importantly, what you ask.

Asking questions puts you in the driver seat to let them air what they have to say while guiding them to what you can do anything about.

Difficult people, especially what Dr. Brinkman and Dr. Kirschner referred to as “whiners”, require a lot of directed questioning in order to come to understand their desires and what actions are available to you.

On the flip side, during this intense questioning, you may end up uncovering something about yourself you wouldn’t have known otherwise.

We decided to test this process this year by conducting face-to-face interviews with our users.

In one of our first interviews, we came up close and personal with the ‘whiner.’ They drained our time, providing vague descriptions while sprinkling it with unpleasant commentary.

We didn’t give up, we kept digging, always having in mind our goal of how we could create a better product.

An hour later, we struck gold. We found out this customer had been using Jotform as a productivity tool.

Customer after customer shared similar tales as our interviews continued over the following weeks.

By continually asking deeper questions of a difficult customer and not giving up, we not only found a new focus in 2018, we discovered the difference between challenging people and unpleasant comments.

3. Get clear between a difficult message and a difficult person

Earlier this year, a customer made several new feature requests and was pretty adamant about their unhappiness with our functionality in a support thread comment.

Good news: they felt comfortable enough to let us know where we didn’t meet their expectations.

Bad news: YIKES.

I didn’t take the grievances shared on our forum personally. I did, however, take it seriously.

I don’t usually jump into support discussions, but this was a critical moment to examine whether this person was being difficult, or giving us an opportunity for improvement.

Further, what if by challenging our platform and strategies, this customer was giving us a huge gift?

I needed to find out.

I saw this as an opportunity and stepped into the forum to respond to the customer’s experience. I provided details on what was going on with the platform that could be causing their issues and also offered my email address for further discussion.

It always helps to get clear between a difficult message and a difficult person.

What couldn’t be seen on the thread was we listening to their issues and ascertaining their end goals through deep diving questions.

Final words

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You will always come across challenging people but by listening to them, asking questions, understanding their goal and focusing your actions, you can put ourself in the best position to succeed in getting what we want.

It won’t always happen in the most pleasant way, but keeping these guidelines in mind helped us handle challenging moments both with our users and within our organization, and hopefully they’ll help you grow, too.

So, don’t freeze and walk away but instead engage head-on with these personalities.

They will push you to innovate, make things better and fill in gaps you didn’t know were there before they arrived.

And I’d say that’s a gift worth getting at the expense of an uncomfortable confrontation, wouldn’t you?

Aytekin Tank is the founder and CEO of Jotform and the bestselling author of Automate Your Busywork. A developer by trade but a storyteller by heart, he writes about his journey as an entrepreneur and shares advice for other startups. He loves to hear from Jotform users. You can reach Aytekin from his official website

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