Impactful Underdog

Healthy Confrontation in Startups

August 02, 2020

We sure all have been there. Some situation doesn’t feel right, or you are certain that your team, your manager, your direct report, or even a C level executive has made a mistake or they have exhibited behavior that might have hurt you or the company. What do you do? You want to be heard, you want to speak up, and you want to influence people in a way to make them aware of their actions, empathize with you, and start recognizing that you might be right, maybe even apologize! I have been in the software industry for more than a decade and most of the time I have been able to influence or convince a colleague by explicitly confronting a particular situation.

Why does it matter?

If done right, confrontation can have the following positive impacts:

  • Influence: at the end of the day, there is something that you want and you can achieve that by rational confrontation.
  • Productivity: confrontation solves problems among people and makes teams productive as a result since team members can now focus on the mutual vision set by the company.
  • Improves relationships: A lot of resentment comes from stacking up unresolved issues that were never shared. So confronting those issues even if they are small can avoid that resentment from happening and help build better relationships at work.
  • Gain respect: People that have the right attitude will respect you and will know that you have the courage to speak up towards a more successful organization.

Important elements of healthy confrontation

Courage through awkwardness

Yes, it can get awkward and we have to acknowledge that. It’s hard to tell a principal engineer that their architectural design is introducing a huge performance issue or your manager is constantly micromanaging the team, or your colleague comes to their desk and starts working right after a workout with a BO (true story!). The reality is people can not get better and improve if they don’t know anything is wrong with what they are doing! You have to practice through this awkwardness one step at a time and you will get better!

Mutual benefits

Confrontation should come from a place of caring deeply in your heart. It should genuinely be aimed to make the other person flourish, improve your working relationship, and ultimately make the organization successful. You need to be ready to accept that you might actually be wrong! That’s another benefit of confrontation because you give the other person in the conversation a chance to explain themselves. Maybe what you have been hypothesizing is incorrect and you should be ready to accept the truth and explicitly tell the other party that they are right and you have made a mistake. You should also be ready to meet the other party halfway; maybe they agree with some of your arguments and disagree with some of it. That’s still a win!

Timing & frequency

Don’t let it build up! The earlier you confront and bring up your points the easier it is for everyone in the organization and the chance of resentment is decreased. Also, if you feel the person you are going to confront might get defensive in a group setting, consider bringing up the matter in a 1-1 setting. There is also a matter of frequency; if you confront every little thing happening in the workplace you might get confused with the person who is always complaining and not a team player. As the wise men say, you have to pick your fights!


Now the hard part, the actual delivery of the message! Be ready to provide lots of data! Remember that the sole objective must be a collaboration for a better organization. The delivery should be very professional, respectful, and the other party should not feel attacked at all. Provide your data, be straight forward without ambiguity and sugar coating the matter. Say it as it is; respectfully.
Example 1: Confronting an engineer insisting on an approach they have implemented that introduces a performance issue system-wide.

I know that you have been really working hard for weeks on this implementation and by looking at the code, it is actually a clever approach. However, I tweaked a small portion of the code and I have compared benchmarks and the response times are drastically better. Do you want me to walk you through it? Maybe you would reconsider parts of your solution?

Example 2: Confronting a colleague leaving passive-aggressive messages in public channels on Slack that hurt people’s feelings.

It’s really inspiring how you as an automation engineer care about the quality of the software that we are delivering, our customers are happy with the product because you are guarding quality with immense passion, however, I have noticed that sometimes you leave comments in public channels about other people’s work that is hurtful and not productive for us as a team. As an example saying “Great! once again we proved our quality of the software by having 100 customer bugs reported within the last 24 hours!” is not very productive. I am sure that you mean no harm and I just wanted to bring this matter to your attention, maybe you can deliver these types of messages in a more respectful productive manner?


Confrontation is something that you get better at by practice but you are not always going to sway another person’s opinion and that’s just the world we live in. However, there are going to be a lot of cases where you are able to influence people and change minds and save the day! After a confrontation, you should always try to ensure that there are no hard feeling between you and the person you confronted.

Just like any other skill, confrontation takes time and practice to master. Don’t confront the VP of the product on the Go-to-Market strategy on your first try! Start small with matters where stakes are not very high and work your way up. You can also start practicing outside of work (and please don’t be mean to the barista who misspelled your name!). you know when you are ready!

If you are interested in learning more I recommend reading these books:

Influence: The Psychology of Persuasion

Never Split the Difference

Written by Mehdi Karamnejad, a tech and startup enthusiast based in Vancouver. Follow on Twitter