I disagree with my boss, what do I do?

I disagree with my boss, what do I do?

Every person working at a startup has an opinion on how to grow the company. This is largely because startups attract hungry people that want to have an impact, lead, and change the world. Not only that, these individuals want to do all this today. Not when they hit 40, or when they have a ton of experience in a particular field. Today. They want to affect change the moment they leave school.

I know, because I’m one of those individuals.

Since established companies have relatively successful processes and business models, not to mention experienced managers and leaders, it’s much more difficult to affect change at a young age working for them. So we take a shortcut: We join a startup.

However, if we believe that by joining a startup, we will always affect change the way we want it, then we’re setting ourselves for great disappointment. Startups, like any company, have obligations to its customers and its investors, which means that we have to do what is right for those individuals, not just us. And for individual contributors and middle level managers like us, we also have to get approval from our boss before taking big decisions.

So what happens when we disagree with our boss on a critical decision? What if we don’t like the responsibility that is assigned to us? What if we think the company strategy, or lack of, is unproductive?

We could leave the company and find something else, but there’s no guarantee that the same thing won’t happen elsewhere. We could also disregard their comment and simply do what we think is right, but that’s creating further conflicts.

Or we could recognize that our boss also wants what’s best for the company, and try talking out our differences. We could try to understand our manager’s perspective and reasoning behind the decision, and share our perspective as well. Why do I favor this option? Because we don’t know everything our managers do, and they don’t know everything that we do. I’m of the opinion that getting upset before we confirm all our assumptions is quite unfair. So let’s share our thoughts and try to get agreement.

Here’s a personal example:

In one case, I was really adamant about a direction that we could take with our product. Based on preliminary market research, we could gain some serious competitive advantage over our competitors with a new feature.

After speaking with my CEO about the idea, we both agreed that further research was warranted, but that there was a clear opportunity. So I led further market research. It was clear that I was passionate about the idea and wanted to lead the project.

Yet once we reached the planning stage and were ready to start work, the rug was pulled from under me and someone else was put in charge of the project, pushing me aside as an “advisor”. I was pissed.

So what did I do? I followed my personal rule of not reacting for 24hrs when I’m emotional, so I focused on other priorities for the day.

After a night’s sleep, I went directly to my CEO and asked for a 15min conversation to clear the air: I directly asked about why another individual was chosen instead of me to lead the project. After hearing my boss out, I gained some additional insight. We even came to an agreement.

Long story short, the project was given to someone on the product team because they are ultimately in charge of our product direction. It would be unfair for me to take over the job of a product manager when I’m not on their team. Fair point. On the other hand, I argued that I had the most knowledge about the project, in addition to having more experience with certain skills that the project requires. So after some exchanges, we came to an agreement that I’d sit on the project as a stakeholder, that all decisions will need my approval, and that I would participate in all product reviews. Yay!

That’s what I had wanted all along. I wouldn’t have minded project managing, but that wasn’t my priority. I was much more concerned about having a voice in how the new product feature gets built, and I got it. I learned about my boss’s perspective, shared my own, and we came to a new agreement. It felt great.

Now, things don’t always go smoothly. So what if I still don’t agree with the decision after talking?

Before quitting the company or going rogue, let’s ask ourselves one last question: Do I trust my manager as a leader, and believe that they have the right values and principles?

Fact is, even after speaking with our manager, there will still be information that we do not have. Our manager may be keeping some information confidential for legal reasons, may be protecting us from harmful knowledge, or simply understand the context of the situation better. So we need to take a judgement on whether we trust our manager as a leader, and whether we respect their character.

If we trust our manager, my opinion is to also trust them with this specific decision and tackle other priorities. As long as we share the same long-term strategic vision as our manager, let’s move on. And fact is, there are usually no clear right answer to a problem, just one that achieves the goal more effectively. So as long as our goals are the same, our manager’s choice still advances us towards the ultimate goal.

If we do not trust our manager as a leader, disagree with their values and principles, then it’s time to consider finding a new team. We simply don’t trust them to lead us anymore. And when we don’t respect our boss, we’re bound to have negative emotions at work and become unproductive. Life’s too short to be frustrated.

So let’s try to get on the same page and validate our assumptions before taking drastic actions.

Finally, HBR has a good article on how to prepare for the tough conversation once you’re ready to disagree. Enjoy.


Recommended exercise

Let’s ask ourselves: “Do I trust my boss?” If not, why? And have I been able to communicate that to them? Have I given them a chance?


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