Working With Difficult People
In the tech industry or any industry, we will encounter difficult people. When I say difficult, I mean ‘difficult to work with.’ Let’s take a closer look at what this means, why it happens, and what you can do about it.

What defines ‘being difficult to work with’?
These are usually individuals with a very different viewpoint from you. They aren’t bad people. And it’s not a reflection of their character at all. They can sometimes be very good at what they do. But this can occasionally make them tough to convince, or inflexible. They could have different priorities from you, or be invested in different things entirely. They could just be very different people!
Problems can arise if you’re working closely with one of them and need frequent buy-in from them. It can get confusing and tiring to constantly ‘convince’ someone. It can slow down the work, and over time, it can cause you to question your abilities, your decisions, and whether you’re the right fit for the job. But worry not. Everything is solvable.
Problems can also arise if a team has several such people on it, and the work is always gridlocked because of strong personalities clashing. Other team members can get caught in the crossfire. The work slows down, and it gets frustrating for those who want to complete the task and move on to others.
Being ‘difficult to work with’ comes with the territory, and it can show up in different ways. Once you understand why someone is behaving a certain way, it’s easier to figure out your way around it. Everyone encounters these problems, and they usually help us get smarter and stronger at what we do. I’ve explained some tricky situations here. Each situation has three parts
- An example
- Why these situations arise
- Possible solutions.
Remember, all these are just suggestions. And all names used are mythical creatures 😊. Here goes.
A different idea of what the work process should be.
The Scenario
Assume you want to create several design iterations and present them to leadership to get their point of view on it. Lisa thinks you should have only two versions of the design and recommend one strongly to leadership as it shows you have more clarity. But you prefer a more open-ended approach.
Why this Happens
In the best case, they may know more about the company, the current state of business, or what leadership is looking for, so they’re advising a certain direction. Worst case, they could be pushing their own agenda or protecting their own team. In-between case, they just have a different approach to work. Having clarity on what’s going on helps.
Possible Solution
Express empathy and understanding for their point of view, and explain your own point of view and your reasons very clearly and assertively. If expressed over a call, put it down in writing in chat or email. Don’t focus on why the process doesn’t work for you. Explain what works better for the company or business.
A Different Expectation on the Task Outcome
The Scenario
Lee thinks that all users are going to embrace a new feature the team is working on. You think that only a certain kind of user, say, power users are going to embrace the new feature. Due to this difference of opinion, many discussions are turning into power struggles.
Why this Happens
Every human is unique. Each of us has a different upbringing, education, psyche and background. Our value systems and personalities can differ wildly. Lee could be more business-oriented, and you could be more design-oriented. This affects our point of view on things.
Possible Solution
Educate yourself as much as possible about the problem. See how competitors have solved similar issues. Examine if your own beliefs hold up. If you still feel strongly about this, try to educate Lee by sharing resources on the topic. Explain your point of view clearly. Have clarity on how many discussions and debates you have the bandwidth (both time and energy) for.
Different Working Styles
The Scenario
Rita expects you to be available for night calls every weeknight. You start the day early and find this hard. Or Deepak likes collaborative working sessions, and you prefer solo focus hours, followed by a meeting to catch up.
Why this Happens
We all have a different way of life. People can have vastly differing opinions on what work-life balance or working style entails. People with small children may often need more supportive and flexible work structures.
Possible Solution
Clearly state your working hours and mark them on your calendar right from day one. Don’t make exceptions easily. If you stay up late for one project, it will be expected of you for every project.
Opinion vs Fact
The Scenario
Jim has bought into widespread popular beliefs like ‘nobody reads,’ ‘blue is the favourite colour globally’ or ‘XYZ company did this with great success, so let’s copy it.’ These statements often do not have scientific backing and can be considered but should not be enforced.
Why this Happens
Jim’s been reading opinions on social media and believes them, or Jim just has strong personal opinions.
Possible Solution
Again, educate yourself and then talk to Jim. Share resources which help your argument. Lean on research if possible to test out which hypothesis works. Opinion and fact are two different things, and everyone needs to be aware of this.
Lack of Clarity About a Task or Project.
The Scenario
Large collaborative projects can have two or more teams working on them, and nobody is in agreement.
Why this Happens
If there is no common vision, clear goal, and strong leadership, the teams can pull in different directions leading to workers being left confused and the project goes around in circles as decisions get differed constantly. The big problem can often be that there is no one decision-maker, and several folks near the top are tussling for this honour.
Possible Solution
If you’re not in charge, then explain this problem to someone who is in charge. If you’re the project lead, set clear expectations and roadmaps and hold people accountable.
Lack of Communication
The Scenario
A deadline changes but you aren’t informed. Or worse, the entire direction of the project changes, but this news gets dropped like a bombshell.
Why this Happens
People genuinely forget to update team members, or they are overworked, or they are confused themselves. Either way, don’t take it personally.
Possible Solution
Update the team regularly in writing, and explicitly ask for updates. Explain how lack of communication means delayed deadlines.
Other Motives at Play
The Scenario
Someone could be more invested in impressing their manager than they are in a project being successful. At other times (and this is very common right now), folks are fearful of layoff, and are acting out of fear. This can lead to power struggles where teams or individuals can behave differently to show higher-ups that they are still of value.
Why this Happens
The hard truth bomb here: not everybody is equally passionate about doing great work. Some are entirely focused on their own career trajectory. Others could be just trying to stay employed.
Possible Solution
Have clarity on what is non-negotiable for you. Are you ready to fight hard for a certain design but are flexible on your work timings? Can you compromise on the date of the deliverable, if you’re getting your way with the work process? It’s a give and take, so know what you’re ready to give away, and what you want out of the whole thing.
Lack of trust
The Scenario
Cho, a product manager, may assume they know better and may not trust the decision of the designer.
Why this Happens
The tech side of the tech industry may not see the creative arts or humanities as equal partners. Some of them may also not feel these skills are essential at all. At times they don’t understand the education, expertise and effort that goes into someone being good at their craft. All this leads to a dismissive attitude towards disciplines that aren’t core ‘techie’.
Possible Solution
Include Cho in the process. Explain all your decisions, even the tiny ones. The best way to counter skepticism is to build trust. This gradual process happens over several collaborations, but it’s worth investing in. Engaging with people we are wary of can be challenging, but it’s exactly what we need to do more of.

Tips
- Express things clearly and dispassionately.
- Track the project closely. Keep an update of discussions in writing, either through chats or emails that are visible to all stakeholders.
- Don’t take things personally.
- Assume best intentions.
- Take breaks from stressful projects whenever possible.
- Talk it over with a trusted buddy.
- Remember that every project is a phase, and it gets over.
- Remind yourself that there is life outside of work.
- Learn to stand your ground. Don’t be a people-pleaser.
- Don’t say ‘this is better for me’. Explain why it is better for the business.
- Don’t bring a knife to a gunfight. If people are arguing about something big, like strategy, there’s no point arguing about where a button should go on screen.
- Know when to escalate things to your manager. It’s not your job to fight all battles, and at times only people on a higher level will be heard. This is one of the unfortunate realities of our world.
Ultimately it comes down to two very powerful questions that you need to ask yourself.
Is this battle worth fighting?
If yes, how much am I willing to fight for it? How important is it to me? If no, then don’t fight it.
Is this in my control?
If yes, then what can I do to change things for the better?
If no, then let it go.
Disclaimer: In the rare case that your manager is highly toxic or exploitative, well, you need to switch teams/tracks or jobs.