How to Work with Difficult People… When You're the Difficult Person
Photo by George Pagan III on Unsplash
I am a difficult person. I am a walking mass of paradox and contradictions. This is my weird. This is my leadership. In the past, when I worked in corporate across design firms, startups, and tech companies, I had a reputation for being difficult. And on top of being Difficult, I was also Divisive, Dismissive, and Disruptive. While I’ve shed a some of those Ds in my journey, I proudly celebrate that I am prickly and difficult.
I am polarizing— people love me or hate me.
Honoring my values of growth, I once asked my manager at Facebook to send an anonymous survey out to people with the question “How much do you enjoy working with Tutti?” on a 1–10 scale. The results clearly indicated polarization — several people at a 1 and a large mass of others at a 9 or 10.
I’ve seen this polarization throughout my career in corporate.
The negative pole of feedback:
Aggressive and impatient. Dismissive of bad ideas. Feels like you’re being interrogated. It’s intimidating.
She is too quick, confident, and competent in coming up with the right answer.
Too intense. Too much for some people. Tends to let her emotions take over.
The positive pole of feedback:
Tutti has X-ray vision and the energy like a 5 year old.
Tutti brings so much passion to the table. She is a clear, direct, and compassionate communicator, and this positive energy rubs off on the rest of the team
She isn’t afraid to fight for the right thing to do. While it’s not always comfortable, I do like that Tutti challenges us all to think more broadly or deeply about the problems being solved. She sets a huge vision and keeps us honest.
Loneliness
I’ve worked with many difficult leaders, both within organizations and now as their coach. These are high performers— brilliant at their craft, visionary, powerful operators, and indispensable to their orgs. They are also incredibly intelligent. They know what’s going on and are completely aware of their impact on others.
It’s an incredibly lonely place to be. There are hidden, never-to-be-spoken regrets of the pain that they’ve caused to others. It’s a life of regret. Of secret shame for the impact that they’ve had on others. Many have big emotions… sometimes it feels like it needs to come out, that it’s a giant volcano of passion and energy that’s about to blow, and they can’t stop it.
Most difficult leaders trap this away under a persona of high expectations and competence. Their outer veneer is a prickly exterior protection for the soft inside. I know because it’s a familiar place.
Signs that You Might be a Difficult Person
You hardly listen to others.You have fixed & rigid ideas.
You are quick to criticize.
You focus on the negative and draw-backs to an idea.
You are easily irritated by others.
You lack patience and tolerance.
You are very competitive in all aspect of life.
You are in love with your ideas
If some of these signs resonate, you may be difficult for people to deal with.
Starting to Change: Name it to Tame it
If you’re longing for something to be different, the first step is to recognize that you are part of the problem, and acknowledge that there is a desire to change.
Perhaps there is a yearning:
For stronger, deeper relationships
To be liked / respected / admired
To have better predictability over your emotions
For me, there was a yearning for all three. I had learned to thrive in my difficult personality in agencies and design firms where I was the Design Director or Creative Director responsible for the innovative concepts we were producing for the world’s top brands. Often the sole female leader in the room, I put on my armor of extreme competence and played my part in the performance to sell clients on the brilliance of our solutions. I was fantastic with our clients.
Yet it still wasn’t enough within the leadership of the design firm as I wasn’t able to “hang with the boys and shoot the shit.” Even in my excelling, I was failing.
After design firms, I transitioned to startups and tech companies that valued culture, processes, and relationships in addition to product excellence. They taught me a new model of leadership where I could celebrate being myself and acknowledge that some of the dismissiveness and need-to-be-right was from my own pain and insecurities. I learned that I could relax the armor and start to show more of my inside self. I learned to share my vulnerabilities and form strong, lasting relationships. It felt more like home.
I shed parts of my difficult self and it took a lot of work. I’ll share two openings for what’s worked.
Opening 1: Focus on Relationships not Ideas
Harvard University research into adult development tracked 724 participants over the course of 75 years and found that the key to long-term fulfillment is… relationships. Excerpted from the Mindmaven blog,
Here’s Robert Waldinger, director of the Harvard Study of Adult Development:
“The clearest message that we get from this 75-year study is this: Good relationships keep us happier and healthier. Period.”
In other words: The quality of our life — emotionally, physically, and mentally — is directly proportional to the quality of our relationships.
The first opening for me was considering the impact that I was having on other people. And what that impact became over time as each negative or difficult interaction was compounded month over month. You see, I truly cared about people. My team was family (family is one of my core values) and I would go to the ends of the earth for them. I had to re-frame that every single person I interacted with at work was “my team.” I needed to be gentler about judgement, both of them and myself. I needed to slow down, be patient and consider the longer view.
I needed to drop my attachment to ideas. As a product person and designer, this is hard. The craft of a product designer is coming up with ideas and bring them to life in a prototype or video to paint this future vision for everyone else to see. Ideas are cheap. Many of the best ideas in Silicon Valley are copycats with a tweak. Good artists steal and adapt.
I realized as I launched product after product over my years in technology, that I wasn’t proudest of the products. I was proud of the work and the impact of the products on people’s lives. But most of all, I remembered the people, the relationships, the culture, and camaraderie of getting to an idea together.
The opening for me was following the path of relationships and curiosity. Instead of ideas, I spent more time with people. Listening more, understanding them more, and truly seeking to discover what mattered to them.
Opening 2: Find Your People
So remember I started this post about being a walking mass of paradox and contradictions? This second opening is a paradox when paired with the first one. This second opening is to celebrate what makes you a difficult person. I am challenging, direct, and prickly. I am highly emotional— I will dance with joy to celebrate your victory, and I will cry tears of empathy when touched by a story. I will challenge you to dream bigger and I will always speak my truth. I am polarizing and I am uniquely me.
To celebrate your weird and difficult, you need to find your people.
How did you feel when you read the negative feedback that I shared above?
One woman in my close circle wrote to me:
“This feedback made me feel kind angry. It reads as white men giving an assertive women feedback “aggressive, too confident, too emotional.” Women who are “difficult” are often called out as such a lot more than their male counterparts.”
I hadn’t originally shared my fierce feminist perspective. That’s a future conversation for later. I believe that we live in a world of unconscious bias and we all hold these biases. And that’s OK. Part of being a difficult person is being myself. There will be people who love it, and others who will be repelled. The woman in my close circle who voiced her anger— she is my people.
As I’ve transitioned into running my own business, I’ve learned to find my people. I follow the weird, the interesting, the different. I look for diversity, both for people who have shared backgrounds and experiences, and I also look for people completely foreign to me. I’m following the relationships, and finding the people I can be completely at home around.
How will you to find your people? How can you celebrate what makes you weird?
Bottom-Line
If you feel like you’re surrounded by difficult people and want to work better with them, first consider if you’re the difficult person. It’s OK to be a walking paradox. You can be a difficult person and celebrate that. You can also work on your range and choose when to be difficult, when to focus on relationships, when to find your people, and when to choose all of the above.
Reach out to me for a chat… I’m a champion of difficult people. I’ve been there. You are not alone.
This is a continuation of the Difficult People series. The entire series is:
Thank you to Parissa Behnia and Julie Colbrese for opening my eyes to the magic of championing difficult people.