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How to work with difficult people… when you might be the difficult personFeatured

Throughout my career, a reputation for being a “difficult person” has followed me. I know that I’m passionate about ideas, have a strong point of view, and have a direct communication style. And for many years, I couldn’t understand how to reconcile “being myself” with why others thought I was so difficult.

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.

I realized that both poles of feedback—the negative and the positive were true—and that through the years I had been excessively focused on “fixing” myself and changing myself into someone else. There’s nothing wrong with being perceived as a difficult person. There can be an intense collection of big emotions inside, fuelled by a passion and vision for what needs to be done. You have strong opinions and believe in how beautiful your vision of the future is. You want it so badly because it’ll be great for the business, the organization, and the people who will use your products. It feels like the right path, the North Star for us all to head towards.

Yet, that “difficult” style of leadership, being “myself” was causing damage to other people around me. It felt like it was most impacting quieter coworkers, people with different styles, and I felt a little ashamed that I was inadvertently shutting down a diversity of opinion.

Some of this feedback is representative of unconscious bias in the tech system that we live in. A woman who is direct and passionate is often viewed as less likable and less competent than the equivalent man. However, as women leaders, we can sift through the feedback and decide how we want to react. Because we still need to survive and have careers within this system of bias.

Three strategies have worked for me to practice the range of how I show up as a leader and communicate with other people. They’ve helped to dissipate some of my reputation as a “difficult” person.

First, focus on relationships not ideas.

A Harvard University research project on adult development tracked 724 participants over the course of seventy-five years to “identify the psychosocial predictors of healthy aging.” The Harvard study found that the key to happy and healthy aging was strong relationships.

The first strategy 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 judgment, 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 bringing 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 the camaraderie of getting to an idea together.

Second, start with listening.

In meetings, I often spoke first. I had a clear idea of where our project was going to go and I wanted to share that vision with everyone else. However, that passion took the air out of the room. In order to make space for other people, and to open myself up to the possibility of divergent ideas, I followed a strategy of listening and gathering information first. I would spend at least 50% of the meeting hearing everyone else’s opinion, and made sure to give space to the less vocal people. It’s a fine art in psychological safety to provide the space for a quiet coworker to interject their opinion while also not “outing” them and making them uncomfortable about speaking. It can feel awkward, however, it’s better than not providing the opening by asking someone else’s opinion.

If there is disagreement with the other person’s opinion, listen enough so that you can find the 10% truth to what the other person is saying. You don’t have to lie and pretend to agree with them. Instead, find the 10% that you can agree with. Restate that 10%, “What I really like about what you said is…” and then build upon it using the “Yes, and…” game from improv. Using this technique will continually make the other person feel heard and help you build upon your thesis.

Finally, find your allies.

Professionally, my insight moment about the difficult person story came when I observed the polarization: one cluster of people who never wanted to work with me again, and the larger cluster of people who followed me from company to company. The latter group was my allies. It can feel exhausting to always need to watch your words and practice less familiar skills such as listening first. What helps is having a trusted small group of allies, both within and outside of your organization. Having a “work spouse,” someone you trust, someone you can vent with, and someone who can lovingly point out mistakes is a great source of energy and motivation within the workplace.

These three strategies have worked for me to help exercise range in my leadership style. When I work with people who are more like me—direct, passionate, with a strong point of view—I can be more like myself. And when I work with a diverse group of people, then I adjust my communication style to be more open and receptive to different perspectives. The feedback was crucial for me to both celebrate my strengths and also adjust how I showed up as a leader. The biggest insight was to practice range using those three strategies.

While some of the critical feedback sounds like someone intimidated by you ('She is too quick, confident, and competent in coming up with the right answer.' smh), I appreciate you taking it, and the reasonable feedback, seriously enough to ask for improvement and change depending on the group.
Thank you for reading and commenting. Yes... I've always had this penchant for continuous growth which is probably why this second career as a coach suits me so well.
Thanks for sharing you process here. Your openness to hearing feedback and finding how to incorporate it is admirable. I have tried to adopt a "argue like I'm right and listen like I'm wrong" approach. When someone disagrees with me, I look for the points they are making to see what I have missed. And I thank them for sharing. I often think about a Jane Goodall quote when it comes to the bias in the system you mention. "“It actually doesn't take much to be considered a difficult woman. That's why there are so many of us."
Genius! I love that Jane Goodall quote and have never heard it. Thank you for sharing.
Thank you for sharing! I appreciate your perspective and that you were willing to consider other experiences and POVs without sacrificing the things that drive you. Very cool insights.
I appreciate hearing that! It continues to be healing to hear the resonance from other women.
I haven't finished reading the post. I will update my comment again. But what you wrote touched me to my bones. It sounded like you are telling me my story :O :O :O
🙏 💜. Hang in there. It always helps me to know that I'm not alone, that sometimes it's a response felt by many who are "other"-ed in a workplace.
Thanks for sharing. I specifically like that you recognized that the point is to make space for others, make them feel heard and appreciate their different working styles. It takes humility and courage to recognize and act on the changes you made while not losing who you are. I believe this is one of the key elements to foster a healthy leadership style and a healthy work environment. Thanks so much!
Thank you so much for reading and commenting. I also think it's not an easy process, but becomes easier with more time, more experience, and more reflection.
Well this made me feel less alone in this world. Thank you @tutti
YES! We are not alone in this! I appreciate your taking a minute to comment.
I feel very seen right now. I've often found myself a bit polarizing, especially in the workplace where I really care about delivering value and taking a stance to get things done. I am continuously learning those 3 skills and am realizing the higher you go and the "stronger" you come off - the harder it is to find allies at your peer level. My allies typically come from above and often below vs my peer level. Interesting...
I find that same trend (allies coming from above and below, vs peers) with many of the people I coach. Most servant leaders have figured out how to be supportive managers, and also to open up with trust and vulnerability for leaders above them that they trust. The peers are the hardest. And when you rise up, there comes a point where you have no more people "above" you, so it's a tremendous skillset to learn to build these equally vulnerable relationships with equals.
This was a wonderful read ! I currently work with someone who is quite difficult to work with for different reasons from the ones you've highlighted here but I really appreciated your bullet #2 on "listening first"! I think often times we fail to do so and it can lead to inefficient work styles!
I’m glad that one of the tips resonated even with a different use case!
Thank you so much for sharing your experience and what you have learned! Your strategies are very helpful!
Thank you for writing in and responding. I appreciate it.
Love this, Tutti. I’m with some of the other commenters, it feels like I’m reading my story. Feedback like this can spiral anyone into imposter syndrome, but you’ve demonstrated how you can turn that feedback on its head. I’m over here cheerleading you on!
Thank you for reading the story and commenting. Heh... don't worry, I have my own fair share of imposter syndrome. I think we all do. One of my coaches told me that if you keep reaching to be in bigger rooms and bigger goals, that imposter syndrome will always be with you. And it's a healthy sign of wanting to be more. And yes, I believe that I can own the feedback. I always feel that "feedback is a gift." And you can choose what to do with the gift. Take it and cherish it. Re-gift it. Or dump the gift in the goodwill bag. Thank you for cheerleading me on. I appreciate it. And I believe we need to do it for each other, always.
Thank you for sharing. I become particularly insecure around this subject when I see it having a bigger impact on men... When I'm the unique female voice in the room. Or when, like you, I know I'm very open to feedback and will have that hard talk and admit my mistakes... But then the people who feel so free to offer that advice, don't own their participation in the situation. That is hard.
@katerpiddah Absolutely. It’s so hard when you feel that you’re going above and beyond. I often feel that women and even more so women of color work 10x harder. I keep thinking of Michelle Obama’s quote: “When they go low, we go high.”
You might as well have been writing the story of my career here! Thank you for taking time to encapsulate the unconscious bias women encounter, even more so as an Asian American woman (expectations to be quiet and submissive).Something that helped me was developing ways to "soften" my message. I say things like, "I could be wrong..." or "I wonder..." or "Maybe..." when I'm much more sure of my thoughts. It makes space for people and lets them feel like they can disagree or ask for a more robust discussion.
@penderle Thank you for sharing the suggestions that work for you!I’m currently writing a book on leadership for Asian American women so your comments are also right on point. Many built-in stereotypes!
Thank you @tutti - great honesty and vulnerability. It’s great to see people that do the work of developing others also be open to growing themselves.
@erickanicole Thank you! I decided I like this line of work so much that I’m now in my second career as an executive coach after spending 22 years as a design leader in tech. Gotta walk the walk!