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Team Management
Product Management

Top 5 Ways to Deal with Difficult People

May 16, 2019
By Son Vo

We’ve all been there when you’ve hit the proverbial brick wall with a difficult, or outright unreasonable people.

These are the telltale signs of hitting the said wall:

  • They are not keeping pace with the rest of the team, or way off-track entirely
  • They ooze negativity, bringing a dark cloud over every project
  • They question every decision or shoot down every idea, however mundane, just to make their presence known or promote their seniority
  • They make unreasonable demands, and are not willing to compromise

Ultimately, we’re paid to work with these folks, not to make friends. These are the top 5 ways to deal with difficult people.

Establish Clear Expectations and Boundaries

You know what works best for you, so are YOU communicating what YOU need? It’s extremely perplexing that in today’s world with a million ways to connect to someone, many issues at the workplace are still the result of miscommunication or lack of communication.


Some would advise distancing yourself from difficult people, but that can be a short-term fix that doesn’t resolve anything. Be proactive and assertive as to what is or is not working. If you wait until near release date to find out somebody is behind on their component, what could you have done better to communicate or assess progress the week before? If they are constantly negative and/or condescending, clearly state what you will not tolerate and what lines they have crossed.

Be a Resource

People are generally nicer when they need something, right? Establishing a reputation as someone who’s not afraid of doing the dirty work, or something that’s outside their job description can be extremely useful. Everyone claims they have this talent during their interviews, but most do not show it on a regular basis. Don’t let difficult people, or the chaos of the situation, prevent you from offering a solution.


If that difficult person doesn’t know Excel, offer to draft some analysis with pivot tables and pretty graphs. Maybe you end up making them look good and can leverage that favor for a future need. If they don’t recognize your good deed, do it often enough and somebody else will. Everyone has a need or shortcoming that they can use help with, find out what that is and use it to your advantage.

Choose Your Battles and Focus on the Bigger Goals

The first battle is internal. Develop some way of staying calm and not let your emotions dictate how you react to the situation. Take a few breaths or excuse yourself for five minutes. This goes back to the first point about establishing clear expectations and boundaries. Sometimes those boundaries are within yourself. Once you’ve established a sense of calm, approach the person from a purely practical standpoint. Ask them to reiterate their position, or see if there is any common ground to expand on. Focus on the facts, which should be the only things left after emotions are removed.

If you are not making any progress, maybe the best choice is to come back another day to get what you need. Perhaps you shouldn’t go about it alone, see if there is a third person that can mediate the situation or provide another approach to the problem. Ultimately, the larger overall goal is more important - completing the feature, getting the client to renew, appeasing a critical stakeholder. You’ll most likely have to work with this person again, so are you sure this is the hill you want to die on?


Iterate and Recognize Positive Changes

In the spirit of agile principles, reflect on what works and what doesn’t with these difficult people, and what you want to change or enhance. Does changing meeting formats seem to lead to better collaboration? Does this person prefer to not interact in the mornings, or during some stretch of the month when they are particularly busy with other work? Be very intentional and state (or celebrate) positive developments. A simple thank you costs nothing, but small wins are still wins that can you can build on.


Be Open-Minded

It’s generally a good idea to trust your instincts, but it’s equally important to realize you don’t know everything. Try to be genuinely curious about the other person’s perspective. Oftentimes, asking what solutions they would propose puts them in a position to put up or shut up. Try to understand what they really are trying to gain (or avoid). Are they dismissing other people’s ideas because of previous mistakes that keep occuring? Do they have trouble stating their position due to misunderstanding or lack of experience? Clarify points of contention and try to expand on common ground. It’s nothing groundbreaking but it takes some humility and a ton of effort.


Working with difficult people is a part of almost all jobs. Yet you can maximize the chances for at least a productive relationship if you are willing to put in the time and the work. A little empathy doesn’t hurt either. If all else fails, you can always start your own company.

About The Author
Son Vo

Son Vo is a Product Owner at Kelley Blue Book/Cox Automotive - the most recognized and most used third-party brand for car research and shopping in the US. His background includes roles in program management, digital marketing, and product development. A technology enthusiast, he enjoys learning, using, and advocating products that make life easier and better. Avid traveler, will try anything twice, and never met a margarita he didn’t like.

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