16 Techniques for Dealing With Difficult Colleagues in Early Careers
Navigating the complexities of workplace dynamics can be a daunting task, especially when dealing with difficult bosses or coworkers. We’ve gathered insights from seasoned professionals, including CEOs and founders, to share their strategies. From leading with tactful influence to managing with openness and empathy, explore sixteen unique approaches that have proven effective in managing challenging relationships early in their careers.
- Lead with Tactful Influence
- Embrace Emotional Intelligence
- Utilize Humility and Accountability
- Navigate Micromanagement with Strategy
- Personalize Team Member Support
- Stand Up Against Intimidation
- Set Limits with Grace and Humor
- Gain Perspective on Generational Differences
- Employ Kindness and Psychological Insight
- Confront Issues with Professionalism
- Communicate Proactively with Empathy
- Find Common Ground and Seek Guidance
- Initiate Open Conversations on Collaboration
- Address Negativity with Direct Communication
- Establish Clear Professional Boundaries
- Involve Management in Conflict Resolution
- Manage with Openness and Empathy
Lead with Tactful Influence
I got the position of Team Lead quite early. After university, I got a job at a company as a junior developer, and after three years, I was entrusted with managing my team. There was an employee on this team who had worked at the company much longer than I had. He believed that the position should have been his.
As a result, I was faced with outright neglect and a lack of any respect on his part. Combined with the fact that this was my first managerial position, I had a very difficult time at the beginning. Consequently, I developed two approaches for working with this employee.
Firstly, I did not directly express my ideas at first but carefully led him to them, so that the problematic employee had the feeling that these were his ideas. In this case, he made a lot of effort to implement them. Secondly, I carefully moved our relationship out of the “parent-child” zone (the funny thing is that he was the “child”) into the “adult-adult” zone. I tried to maintain our “adult-adult” communication as long as possible during conversations.
As a result, after a few months, I noticed that he stopped perceiving me as hostile, and we began to truly cooperate, rather than try to prove which of us was more authoritative.
Viktoria Dolzhenko, Team Lead, Itez
Embrace Emotional Intelligence
Own it, even if you didn’t create it. My clients are the boss. They are high-achieving, hugely successful, and demanding.
One of my favorite stories is from my earliest years in business. A client called in a rage because she was lost on her way to our meeting. I talked her through it, and when she arrived, she was very worked up, and it was clear no matter what I said, I could not win.
This was not a great start. She wouldn’t allow me to explain that our email thread included her acknowledgment of our meeting location and instructions on how to find it. Her argument was that she was too busy to read emails. She looked up my website; she went to the mailing address.
As the owner of the business, it was my fault that she was lost, and no details aside from that mattered. Like many of my clients, this woman had graduated in the top 5% with her Harvard MBA. She was now a venture capitalist with the ability to choose where, when, and with whom to work. I took a deep breath and realized that I could learn something from her. Allowing myself to be challenged in this way was like getting a masterclass in Emotional Intelligence.
Without resistance or emotion, I thanked her for bringing this to my attention. Then I suggested we move on. This experience was one of many that taught me so much. But it’s memorable because she not only remained a client for over a decade, she referred so many new clients my way that I once sent her flowers. Which she did not acknowledge. And that was, and still is, okay.
Emily Dills, Founder, Seattle Nanny Network, Inc.
Utilize Humility and Accountability
Genuine humility has a surprisingly disarming effect on others. When faced with a challenging co-worker or burdensome boss, resist the temptation to embroil yourself in a battle of wills. Instead, employ a hint of interpersonal jujitsu by leveraging your relative newness and willingness to learn.
Simply acknowledge the tension, accept accountability for your contribution, and ask how you might adjust your behavior to enhance the relationship. Most will be impressed by the professionalism and compelled to follow suit.
For the dense few who fail to offer a similar adjustment, your action affords you the right to a direct request. Simply say, “This relationship is important to me, and I’m happy to do X. I believe we’d achieve even greater results if you did Y.” The strategy underscores the natural give-and-take in all effective relationships and makes it hard to refuse your ask.
Tim Toterhi, CHRO, Plotline Leadership
Navigate Micromanagement with Strategy
My first boss was an absolute micromanager. I was creating social media content for a medium-sized business. I was the entire social media department, and the whole marketing team was three people. The CEO of the company insisted on reading, giving feedback on, and approving every single post I put up. He also wanted to handle any direct replies to customers himself, even though this was part of my job description.
Meanwhile, the actual head of the marketing department had performance standards for me—including creating a minimum number of posts for each platform we operated on each day. The CEO’s meddling basically made this impossible. Finally, I explained the situation to the marketing head, and she and I decided to simply let the CEO do what he wanted.
As long as we kept a paper trail, she would be able to defend my productivity at performance review time. This was enough to keep me employed, but I was never going to earn a raise in an environment like this. Luckily, my immediate boss was able to write me a stellar reference letter, and I was gone within six months.
Nick Valentino, VP of Market Operations, Bellhop
Personalize Team Member Support
Early in my career with a digital media company, when I was promoted to team lead of our guest-post writers, I had to handle two difficult team members who were having challenges with the many details involved in writing, submitting, and correcting their articles.
I handled each by reviewing their work to find the mistakes they would commonly make, then creating a personalized “cheat sheet” for each of them to ensure they checked off certain items before turning in their work.
I also coordinated with a team member who excelled at training, and she created a training video for each writer specific to their needs and then held a training session with them.
Through these efforts, we were able to help one team member overcome anxiety with technology, and the other to consistently use mandatory reference guides and online tools.
Michelle Robbins, Licensed Insurance Agent, Clearsurance.com
Stand Up Against Intimidation
At the beginning stage of my career, there was this particular coworker who was a big bully. He was so unproductive, difficult to work with, disrespectful, and he felt he could get away with everything. I guess his huge, masculine physique contributed to this.
I had to work extra hard to make up for his inadequacy because we were in the same section at work, and I didn’t want him to be the reason for our falling behind.
I was enduring his unprofessionalism and trying my best to stay clear of him until the day he did something that hit my last nerve. He deleted every single document I had been using the past month to compile, and he told me straight to my face that there was nothing I could do about it.
For the first time in our history of working together, I stood up for myself. I had never done it before because of how scared I was of him, but that day, I decided I had had enough. To this day, I don’t know where the strength or confidence came from, but I stood up against him and told him how much of a horrible person he was, how I was never going to tolerate his disrespect, and how I was going to get him fired if he didn’t take his work seriously.
For the first time, he looked subdued and harmless, and that was when I realized he was just a random, lazy bully who was only good at making empty threats. He never tried bullying anyone again after that incident, and shortly after, he resigned.
I learned a major lesson that day, and that was to always stand up for myself.
Grace Chisom, Marketing Manager, Check CPS
Set Limits with Grace and Humor
I’ve learned how to handle difficult relationships with managers and coworkers. I learned leadership skills from running a revolutionary resin-injection subsidence repair company.
Over the years, I’ve learned to graciously set limits, which is essential to good leadership. Politely and firmly setting limits is essential when dealing with disruptive or poisonous behavior. Instead of constant micromanaging, try weekly progress updates. This preserves my health and improves the workplace.
Humor is a valuable ally in complex work relationships. With the right timing and tone, a joke or lighter quip can release tension and build togetherness. Sarcasm and degrading humor can backfire and worsen problems.
My method of appealing to challenging employers or coworkers’ higher selves works well. By gently reminding them of our shared aims, ideals, or their work’s positive impact, negativity fades. This strategy fosters collaboration and a positive outlook, promoting achievement.
In the dynamic world of Subsidence Ltd., where precision and innovation are key, my unique and effective workplace problem-management tactics have survived and built a resilient and successful team. These real-world lessons emphasize the necessity of subtlety, empathy, and strategy in overcoming professional challenges.
Matthew O’Sullivan, CEO, Subsidence LTD
Gain Perspective on Generational Differences
The clash between a young employee and an older boss is as old as time. It’s a generational clash and a power clash, and it can end in resentment and bitterness. Like many young men, I was also full of energy, ideas, and ideals, and I did not appreciate being ordered around or shot down by my much older boss, whom I thought was overly “safe,” cautious, and unimaginative. There were many conflicts because of it.
What helped me navigate this in the end was realizing that none of this was about me. This guy wasn’t jealous and threatened by my youth and exuberance, as I thought in my delusional, cocky youth; this was his business, his life’s work, and he was cautious. He was protecting his work. Understanding that changed my entire perspective and approach.
Rick Berres, Owner, Honey-Doers
Employ Kindness and Psychological Insight
We’ve all had at least one awful job that came with a difficult boss or coworker, or both. However, these jobs are a great opportunity to learn about psychology and human nature.
Something about me really poked my manager right in the insecurity, and he took it out on me. I was never brash or braggadocious. He just knew that I was going to be successful, and that he was going to still be a manager at the same restaurant, so he took it out on me. I simply let it roll off my back and killed him with kindness. It’s hard to be terrible to someone who goes out of their way to be kind to you.
Eventually, he stopped trying to goad me, and I quit shortly thereafter. However, for someone who finds themselves stuck with a difficult coworker in a job you plan to keep, study psychology. Figure them out. Understand them fully, and you can push the right buttons to keep them under control.
Kam Talebi, CEO, Gigli
Confront Issues with Professionalism
Difficult is a broad term when defining a co-worker’s or boss’s behavior, because some people label a person as difficult when they fail to receive favor or a desired outcome from their work colleague.
If a person’s work ethic or personality is challenging to coexist with, then take an opportunity to meet with them one-on-one to inquire if everything is okay. If they’re actively listening, they’ll ask why you’re inquiring about them. Allow that opportunity to share specific examples of their behavior and how it’s impacting the work environment and the progress of other team members.
If you don’t address the challenge head-on, then you’ll invite more problems to resolve over time. Be professional, look them in the eye, and state your concerns by addressing them by their first name, so there’s no misunderstanding of whom you’re addressing in the moment. Suggest how they can make a better effort in adjusting their behaviors to positively contribute to the work environment.
If they become combative or defensive by adhering to poor coping mechanisms that can border on harassment, then escalate your matter to the appropriate members in the organization.
If they ignore the matter, whether it’s big or small, then take matters into your own hands by seeking external counsel, because not all organizations are competent at doing their job. Context matters. Reflect upon the difficult and/or sensitive situation that needs attention prior to taking any action.
Sasha Laghonh, Founder, Sasha Talks
Communicate Proactively with Empathy
In my early career, I encountered a challenging situation with a boss who had a very direct and occasionally dismissive management style. To manage this effectively, I adopted a strategy of proactive communication and empathy. Instead of reacting defensively to criticism, I tried to understand their perspective and expectations better. I scheduled regular meetings to discuss project goals and my progress, ensuring we were on the same page.
One specific instance that stands out was when I presented a detailed project plan, anticipating questions and addressing potential concerns upfront. This approach not only demonstrated my initiative and competence but also helped build a more constructive working relationship.
By maintaining professionalism and focusing on open communication, I was able to turn a challenging situation into a learning opportunity, gaining valuable insights into effective communication and resilience in the workplace.
Daniel Bunn, Director, Incensen
Find Common Ground and Seek Guidance
Early in my career, I encountered a challenging dynamic with a colleague whose approach clashed with mine. We did not see eye to eye on how we should tackle various projects, and it became a very strenuous work environment.
Instead of focusing on our differences, I emphasized finding common ground and aligning our goals for the project. I could express my ideas more effectively by listening to and acknowledging their viewpoints and opinions. Patience was crucial; I allowed space for mutual respect to develop gradually.
Additionally, I sought guidance from people I respected in the company to gain insights into navigating such situations professionally. It is inevitable that you will encounter these types of situations during your career. However, experiencing this kind of conflict taught me the power of empathy, patience, and constructive dialogue in managing complex professional relationships.
Sacha Ferrandi, Founder and Principal, Source Capital
Initiate Open Conversations on Collaboration
I once held an administrative role where I supported several executives, and one of the executives was very demanding. In my first three months on the job, they never once expressed gratitude, even when I went above and beyond. I also saw them treat other members differently, which made it tough for me to feel engaged at work.
One day, I gathered the courage to sit down with them to provide feedback. I shared that I wanted us to have a strong working relationship but that I didn’t feel my contributions were valued. Despite the power dynamic, they were receptive and apologized for leaving a negative impression.
The next day, they thanked me after completing a small task for them, and our relationship improved from that point onward. This situation underscored the importance of having an open conversation about collaboration and working styles—a topic I cover in my work today.
Alex Lahmeyer, Founder and DEI Consultant, Boundless Arc
Address Negativity with Direct Communication
Early on in my career, I had a coworker who often had a negative attitude that affected the overall workplace environment. Rather than reacting impulsively, I chose to approach the situation strategically. I started by trying to understand their perspective, seeking insight into what might be causing their negativity.
However, when this approach didn’t lead to any improvement, I considered it necessary to address the issue directly. I initiated a calm, respectful conversation, expressing my concern about the impact of their negativity on the team’s morale. This conversation opened a door for better communication, leading to improved relations and a more positive work environment.
This experience taught me the importance of empathy, patience, and direct communication in managing challenging relationships.
Matthew Lake, Managing Director, Guardian Safe and Vault
Establish Clear Professional Boundaries
I employed the strategy of proactive boundary-setting. Understanding the dynamics, I respectfully established clear boundaries for tasks and communication. By diplomatically asserting limits while remaining open to collaboration, I preserved personal and professional space, creating a more balanced and respectful interaction with my challenging colleague or boss. This approach cultivated a healthier working relationship based on mutual understanding and respect for boundaries.
Maxi Extrakt, CEO, Fort Lauderdale Pergolas
Involve Management in Conflict Resolution
Early in my architecture career, I faced the challenge of working alongside a colleague whose borderline anger-management issues would unexpectedly flare up, especially in situations lacking accountability. This coworker’s confrontational behavior over seemingly trivial matters posed a significant challenge.
Despite multiple attempts at conflict resolution and personal appeals, the situation persisted until involving senior management became necessary. Through extensive discussions and mediation, it became apparent that our colleague’s approach was incongruent with the organizational ethos, leading to the realization that their methods couldn’t align with our team’s dynamics. Eventually, this colleague made the decision to depart, recognizing the incompatibility of their approach with the organization’s culture and expectations.
Handling this challenging relationship taught me the importance of patience, perseverance, and involving higher authorities when necessary. It highlighted the significance of exhausting all avenues for conflict resolution and seeking senior management intervention when individual efforts fall short. This experience emphasized the value of organizational alignment and the crucial role of leadership in resolving interpersonal challenges that hinder productivity and harmony within a team.
Andrew Chung, Founder, Best Cafe Designs
Manage with Openness and Empathy
During the initial phases of my professional journey, I encountered numerous obstacles when it came to navigating challenging relationships with supervisors and colleagues.
However, over time, I learned various approaches that allowed me to effectively manage these challenging relationships. One approach that proved to be effective for me was maintaining open and honest communication. Whenever I had an issue or disagreement with a difficult boss or coworker, I made sure to have a conversation with them about it. This allowed me to express my concerns and also understand their perspective, creating mutual understanding and respect. Another approach I found useful was practicing empathy. It’s important to remember that everyone has their own struggles and reasons for behaving in certain ways.
By putting myself in their shoes, I was able to better understand where they were coming from and find a way to work together. I also learned to pick my battles. Not every disagreement or issue was worth fighting over, especially when it came to working with difficult individuals. I had to learn to prioritize and choose which conflicts were worth addressing and which ones I could let go.
Brandon Beatty, Founder and CEO, Southern Hills Home Buyers
