Picking Your Hills to Die On: What to Do When You Can’t Disagree and Commit

In leadership roles, one of the most challenging aspects is deciding when to stand firm on an issue and when to “disagree and commit” for the sake of progress. This blog explores the delicate balance between advocating for what you believe is right and fostering a collaborative environment.

Through personal experiences and a practical framework, we’ll delve into how to assess situations critically, consider second and third-order effects, and manage the risks associated with taking a stand.

The framework I’ll share aims to help navigate these complex decisions:

0) Check Your Emotions

1) Ensure the Solution is Solving the Problem

2) Consider Second and Third-Order Effects

3) Will You Win? Reflect and Retrospect

Disagree and Commit, or Die on the Hill?

“Disagree and Commit” is one of the most important principles for anyone in a leadership position. Though it’s a loose framework, its aim is to ensure everyone in the room is heard, allowing them to express consent—or dissent—before a decision is made. It emphasises that in many situations, we don’t know the correct answer, and often, taking any decision is better than taking none at all.

Such frameworks are crucial within organisations to help them make decisions quickly and continually move forwards. For some companies, like Amazon with its famous leadership principles, these frameworks are deeply ingrained into their culture. Amazon, for instance, emphasises “Have Backbone; Disagree and Commit,” encouraging employees to speak up “even when doing so is uncomfortable or exhausting.” 

Although I haven’t worked at Amazon and can’t speak to how this plays out there, my approach at my own workplace isn’t far off. I often share my opinions followed by, “but this is not a hill I’m going to die on.” This is my way of saying, “I believe this to be true, with about 60% to 75% confidence, but not enough that I want to sway the room on my own.”

There are numerous excellent books on how to have your voice heard—Crucial Conversations is particularly useful. However, this blog will focus on what to do when you disagree and can’t commit, and might need to choose a hill to die on.

Personal Brand Matters: Help everyone make the best decision and Pick Your Hills Carefully

To be successful in any organisation, you need to balance debate with progress. No one wants to work with someone who constantly blocks decisions and argues excessively; it’s isolating for you and exhausting for everyone else. This is especially true in startup environments, where employee cohesion is vital due to often high stress levels.

Having “died on too many hills” early in my career, I’ve made a deliberate effort over the past half-decade to avoid doing so. I place such importance on this mindset and use the phrase so often that my colleagues even made t-shirts featuring it for me! 

However, going back to amazing leadership principles, you also don't want to be known as someone who always agrees with others—sometimes referred to as “yes-people” or “flip-floppers”—and don’t hold their own opinions. Leaders need to take positions and take the risk of standing by them sometimes – so how do you know when you’re standing firm correctly or just being stubborn? 

In the most extreme cases, making the wrong stand can have serious consequences, such as needing to find a new job. Even opting out of a project can leave a mark on your record if it turns out to be a success. So when a decision comes along that you feel you can’t commit to because you believe it’s a one-way door to doom, how do you balance your own risk with that of the organisation and the potential outcome of the decision?

To Die on the Hill or Not: A Loose Framework for Risk Management in Decision-Making

This framework should help you (and anyone else) involved make the best decision, by identifying risk you can mitigate them – or in the worst case scenario, you can choose to make a stand. These steps don’t have to be followed in this exact order, but I’ve found this sequence works best for me.

0) Are You Having an Emotional Reaction to the Decision-Making Conversation?

Yes, starting with zero might seem odd, but this is really a precursor step, as some decisions can evoke strong emotional responses that have a habit of making it hard to analyse risk appropriately.

You might notice your palms getting sweaty, your stomach feeling unsettled like you’re on a rollercoaster, or perhaps you feel anger rising. I’m not here to provide therapy, but it’s important to recognize when this is happening so you can find a way to manage it.

If you have strong personal values, you might react emotionally when a proposal conflicts with them. Or perhaps you’re empathetic and concerned about how the decision might affect others. Whatever the reason, it’s crucial to get yourself into the right headspace before diving into the complexities.

Breathe slowly, assume positive intent, ask curious questions to understand the situation, and if needed, take a moment outside to collect your thoughts.

If in serious doubt, avoid making a decision either way in the room. Instead, discuss your feelings with a trusted friend afterward to help identify what’s affecting you and see whether it’s the content or the presentation of it. 

1) Does the Suggested Solution Address the Most Important Problem?

Great leaders often ask, “What’s the problem you’re trying to solve?” So let’s start there.

Is there a clear link between the problem and the proposed solution? Do you believe one will lead to the other, perhaps with side effects that make it less desirable?

I’m often surprised by how many solutions don’t address a true problem—they emerge because “doing something” is seen as better than doing nothing. This is especially common when new leaders are adjusting to their roles and haven’t realised they might be inadvertently creating issues by constantly putting out fires themselves.

If the suggestion comes from a member of my team, it’s a great opportunity to work through it together. I like to ask them to state their confidence level in the solution—are they 99% sure it will work, 50%, or somewhere in between? This helps frame the conversation, as I've learnt myself that speaking confidently about something doesn’t always mean you believe it. Sometimes they might be 80% confident while I’m at 40%, but if the risk is low, I may let it play out—you benefit either way as a leader.

If the idea comes from a colleague, I might want to see the evidence and data supporting the proposed link. Either way, if there’s any doubt, this is where most of the discussion time should be spent.

2) What Are the Second and Third-Order Effects (Often Described as Risks)?

Understanding second and third-order effects can be challenging. One way to conceptualise them is by thinking about a simple probability tree (for those who remember high school maths). 

For example, your CEO might identify the problem of the company moving too slowly and propose rallying everyone at an all-hands meeting to instil a sense of urgency, aiming to achieve the company mission sooner.

You might agree that this approach could solve the initial problem of increasing speed. However, you may also believe that the second-order effect could be detrimental in the long run, as sustained urgency isn’t a healthy steady state and could lead to employee burnout. This, in turn, might result in a third-order effect of high staff turnover, which slows the company down due to a loss of institutional knowledge and can be extremely costly to remedy.

So, although the solution passes the initial test, considering the second and third-order risks makes it easier to argue against it. To be explicit, this isn’t about getting definitive yes or no answers; rather, it’s a visual tool to facilitate group discussions and help you avoid unnecessarily “dying on too many hills.”

There are many possible second and third-order effects when making decisions, but I’ll discuss three:

1. People Risks: The Potential of Upsetting People with Your Decisions

A real-life example I encountered involved deciding whether to hold an internal conference during the COVID-19 pandemic (when it was legally permitted). Many employees had joined remotely during that period and hadn’t met each other, making it harder to build trust—a crucial element in any fast-paced startup. Bringing everyone together could help solve that problem, and running it remotely had been ruled out due to reported Zoom fatigue. But what about the second-order effects?

Those who attended might contract COVID-19, and those who didn’t attend due to being at high risk might feel even more isolated. Did everyone need to attend, or were there alternative solutions? The third-order effects could be serious, but startups often rely on strong interpersonal relationships to be effective. After gathering employee feedback, we decided to hold the conference. Over 90% attended, and for the few who didn’t, we implemented measures to mitigate any negative impact. In this instance, the risk of the company failing due to a lack of cohesion was deemed too high.

WeWork faced a similar situation when deciding to adopt a fully vegan policy in the office. While this addressed the goal of reducing the company’s environmental impact, the second and third-order effects on employees may have outweighed the benefits in hindsight.

2. PR Risks: The Possibility of Damaging the Team’s or Company’s Brand

I experienced this at a health-tech company when we were considering partnering with a pharmaceutical company to de-risk our income streams. While the partnership would provide financial stability, we were concerned it might upset our NHS partners. If it did, could that discontent spread and jeopardise our brand—our most valuable asset?

Initially, I was against the plan; it seemed too big a risk, especially since the new revenue stream would only be a fraction of what we received from the NHS. However, we investigated the risk by testing our messaging with users and found a way to mitigate it. We adjusted our communications accordingly and successfully launched the partnership. Without mapping out the second and third-order effects, we might have rushed into a poor decision that would have been tough to unwind.

Due to the network effects of the internet, PR risks can spiral out of control. This is why they often cause significant concern, despite being relatively rare and sometimes given disproportionate weight in decision-making—the ‘what if’ questioning.

3. Career Risk: Could This Strain Your Relationship with Your Boss?

Let’s take the example of performance review season. You might believe that someone should be promoted and given a pay raise, but your CEO doesn’t agree. What do you do?

You could discuss progression frameworks and present evidence, including previous conversations where expectations were set. However, second-order effects could include annoying other team members, and third-order effects might involve them deciding to seek alternative employment. There’s also the risk of the promoted individual struggling in the new role due to increased responsibilities. On the other hand, if you don’t promote them, they might become a flight risk.

What about the fact that you would be going against the CEO? What are the second and third-order effects of that? Sometimes you can mitigate these kinds of risks, and sometimes you can’t and have to decide what you’re prepared to risk.

Sometimes, choosing to “die on the hill” is the right decision. I’ve personally done it a few times and would do it again in most cases—but that doesn’t mean it doesn’t come at a cost. If you’re going to take such a stand, you need to consider an important risk: your career. I tend to take more risks than most, and even so, this is something that keeps me up at night. Of course it does—you’ve worked so hard (and been fortunate enough) to get where you are. Is it worth risking throwing it all away?

Well, of course, that depends on what you might gain or risk losing if you go along with the decision and what are your chances of winning anyway? 

3) If You Decide to Gamble and Die on the Hill, Will You “Win”? 

Dying on a hill should never be done lightly and certainly should only be done very rarely, but I have done it more than once…

A Risky Start to my Product Career

One of the earliest “hills I died on” as a Product Manager was during my time at Spotify. I had recently moved into product management and was still building trust with my autonomous team when I was asked by a senior executive to build a “promoted” playlist. He had significant influence and wanted to test an idea, requesting that my team change priorities to accommodate it. I didn’t feel it made sense, as I wasn’t convinced by the idea and knew that changing the team’s direction at short notice could risk how my team viewed me. I also knew my product director hadn’t persuaded me otherwise; they had left the choice and the “fight” to me alone.

I felt that any product team could build it—mine was being chosen because it was better run than some others and therefore able to deliver. However, the reason we were effective was that we didn’t make last-minute changes based on hunches without a clear vision and a solid pitch.

So, I declined politely and instead focused on better explaining what we were delivering and the value it would create for the company. Being new in the role of Product Manager, I decided that the biggest risk was losing my team’s trust. Having seen that happen to others, I chose to risk saying “no” and suggested they find another team. I didn’t stop the project from happening, just diverted the work elsewhere—but it was still a risk. I could have been compelled to do it but gambled that wouldn’t happen, and I was correct.

The experiment wasn’t a success, so in some ways, I played and won, but I’ll never know the damage it might have done with that stakeholder.

A Senior Clash With My Peer

More recently, I made a decision to “die on the hill” regarding how product team accountability should work—namely, that each team should have a technical lead. This was a tough stance, as I was confident that pairing leadership between the Product Manager and Technical Lead would be effective, having seen it succeed in many different organisations. However, despite viewing this as the biggest blocker to the effective delivery of our company goals, I was unable to persuade my engineering counterparts.

I knew it was going to be challenging, given the conversations I had had so far—the engineering leader was committed to implementing Vanilla Scrum and hadn’t experienced the system I was proposing. It also meant more accountability for engineering, which he was not keen on.

So, I needed to assess my odds of success before deciding what to do. I spent time with my peers, my line manager, and a member of the board to understand their perspectives and whether, if necessary, it might be possible to change the engineering leader’s mind. If this sounds Machiavellian, in some ways it was, and I disliked it. But after six months of trying every collaborative method I knew to influence and persuade, we had reached a point where we simply could not move faster as an organisation without this accountable role.

The feedback was positive but guarded, as no one wanted to cause conflict. I weighed the probabilities and reckoned that, based on the needs of the business and our respective reputations, I had about a 60:40 chance of staying if push came to shove. This was one of the most important decisions in a queue of choices about how to structure the organisation from a delivery point of view, and it was the biggest sticking point—the focal point of the conflict. I had decided I was going to die on this hill, and if needed, I knew the decision would go to the board, with our respective careers hanging on it.

However, before we got there, my coach talked me off the ledge, and I found a way to empathise with my counterpart in a new way. We were able to find a compromise that introduced the role but also created a delivery manager position for some of the team (his priority).

This is the most extreme example I have from my career, and I share it cautiously, as it is only a fraction of a larger story. However, I do so to help others, as I think it’s important to consider the extremes when you decide to go against the grain. One advantage I had is that, as a product person, I am used to weighing risks objectively and taking them—as if you don’t take risks as a Product Manager, you never build anything (and might get fired anyway).

A Regret Over Orangina: The Hardest Hill I Chose to Die On

I was working at a hyper-scaling startup that had recently moved offices due to its growth. We transitioned from a liberal “DIY” approach to food and drink (e.g., writing desired items on a blackboard) to a more formal process, which led to an analysis of our purchases and questions about the range of options being provided. I didn’t see this as a great use of the C-suite’s time, believing that we should “focus on what matters” to ensure we continued our drive toward a potential Series C funding round. The CEO, however, viewed it as frivolous and a potential risk to how we managed money—believing that if employees were spending on multiple types of drinks, they might not be spending wisely in other important areas. Both of us had the company’s success at the forefront of our minds but felt that our respective solutions were the right path to those shared goals, even if the paths were in opposite directions.

The CEO exercised his authority, as was his right, and removed approximately 70% of the options in the kitchen. He felt it had become a “hotel buffet” and that people were behaving in an entitled manner, not fitting with the history of the organisation. I, however, felt that we had been key workers during COVID-19 and were doing well financially, so the types of hummus in the fridge were not our biggest concern. I had also read several case studies on the downside of taking away free coffee in companies and wanted to avoid what I saw as a mistake.

One of these cuts was my favourite drink, Orangina. I realise how ludicrous this sounds—I’m not so out of touch that I can’t see that. But at the time, it felt like the tipping point in a fight for the soul of the company and how we wanted to treat our staff. Would we follow Netflix’s “trust your people” philosophy or Amazon’s “frugality” leadership principle? I felt we had hired people who valued the former, and from my previous experience, that could be how we win. I also felt we hadn’t had a conversation as a leadership team, which broke the “disagree and commit” agreement we had made as a C-suite. This was about two things that mattered a lot to me—company culture and how we made decisions as a leadership team.

I chose to die on this hill, at great cost to myself and without much effect in the long run. My attempt to change the CEO’s mind had the opposite effect, and I regret it.

At the time, I thought that if I couldn’t halt the slide toward a low-trust culture, then it probably wouldn’t be a company I would want to work in for much longer anyway—which sadly ended up being the case. It’s still a decision I think about, wondering whether I could have done a better job of finding a different solution.

4) Retrospect

It’s not always obvious until long after the fact, whether or not it was worth dying on the hill or not – often because it depends on whether you were right or not in your analysis, which also means that a huge slice of luck might be involved. You might also never know and have to be comfortable with that. Maybe you died on the hill on behalf of your team, or your organisation, but maybe they didn’t need you to.

Whatever happens choosing to die on a hill will have a toll on you, it is anxiety-inducing and can wear you down emotionally. Ensuring you only die on hills you have to is hopefully part of experience and certainly something you can ask for help in working out from mentors and coaches alike.

As They Say at Nasa, You’ve Got to “Work the Problem"

Deciding when to stand your ground and when to “disagree and commit” is one of the toughest aspects of leadership. Throughout my experiences—whether it was challenging a senior executive on team prioritisation, defending the need for joint accountability, or even standing firm over something as seemingly trivial as office refreshments—I’ve died on a few hills over years, for better or worse.

The framework I’ve shared aims to help navigate these complex decisions:

0) Check Your Emotions

1) Ensure the Solution is solving the Problem

2) Consider Second and Third-Order Effects

3) Will You Win? Reflect and Retrospect

By methodically analysing these factors, you can make more informed choices about which hills are worth dying on.

Remember, every decision carries risks—to your relationships, your team’s morale, or even your own career. It’s crucial to weigh what you might gain against what you could lose. Not every battle is worth fighting, but when you choose to take a stand, do so with conviction, preparation, and a clear understanding of the potential consequences.

Hopefully this helps you next time you’re left with a big decision to make, let me know if you find it useful or have a different methodology :)