How do I pick my battles?
My framework for deciding which battles are worth my time and energy
For the first five years of my career, I constantly heard, “pick your battles, Tim.” I heard the phrase so much that it became meaningless. And I struggled with what it meant: Am I supposed to care less? Not stick up for my opinion? Let things slide that I feel strongly about? This phrase is common advice given in the workplace but often misses the nuance of when you decide to show your conviction in what’s best and how to disagree.
I fought over every detail. My most egregious example was a three-week debate with my PM over using an ampersand symbol or spelling out “and.” The risk of over-indexing on your backbone and fighting over every detail is that you may lose the trust and respect of your peers. Even if you choose to disagree, avoid losing credibility.
Eventually, I learned to calibrate where I put my energies and the approach I took when I thought something was wrong. I learned that I frequently chose to “fight” over every detail. I also found my approach to disagreeing equally important as to “when” I would pick a battle. I’ll tackle this topic two-fold; this week, I’ll cover my framework for deciding which battles to focus on, and next week I’ll share tactics I use to express disagreement.
Prioritize one-way door decisions
In the 2015 Amazon Shareholder Letters Jeff Bezos discusses the distinction between one- and two-way doors: “Some decisions are consequential and irreversible or nearly irreversible – one-way doors – and these decisions must be made methodically, carefully, slowly, with great deliberation and consultation. If you walk through and don’t like what you see on the other side, you can’t get back to where you were before... But most decisions aren’t like that – they are changeable, reversible – they’re two-way doors. If you’ve made a suboptimal [two-way door] decision, you don’t have to live with the consequences for that long. You can reopen the door and go back through.”
The first lens I use when picking my battles is to understand if the decision is reversible. You can also think about “expensive two-way door decisions”. These decisions may be less reversible because of the cost (time, resources) that went into making that decision. For example, if I had to decide between saving the team a few hours (e.g. “this brainstorm isn’t a good use of time”) versus a few months (e.g. “this feature likely won’t have the impact we want it to”) I would prioritize the latter because it’s an expensive two-way door. In many cases in product design, design decisions can be easily reversed if new evidence shows otherwise. Also, consider how many customers will be impacted and the potential problem’s significance. Avoid picking battles that affect few customers or where either decision wouldn’t be significantly adverse to the CX. Through this lens, you can pick fewer battles that are two-way doors, impact fewer customers, or the CX frustration risk is lower.
Prioritize product ideologies over smaller details
When building a product, we make thousands of micro-decisions – what text should we use? What color for the font? Is this the right photography? Should this feature be a P0 or a P1? At any point, there can be disagreements over these ‘micro-decisions.’ These decisions are excellent examples of two-way doors and ones I suggest prioritizing less. Instead, I’ve learned to focus my attention and energy on discussions on product ideologies – How do we make decisions? What are our tenets? How do we decide what is best for customers? What would it take to let our goal slip to red so we can build the right thing? For me, these discussions are worth having because they are more consequential and impactful across many decisions, not just micro-decisions.
If you find yourself arguing over something like ‘what’s the right text color, then you should step back and ask what the macro-decision the team needs to make. Here’s an example. As an accessibility advocate, I often find myself defending micro-level decisions like color contrast. To up-level a discussion from colors, I’ll ask questions like “Is there a reason we wouldn’t follow accessibility guidelines?” Rather than talk about colors, we can discuss what we believe is best for customers and why we think that’s true.
If you’d like to do more strategic work, then you have to be willing to give up some specific details so you can invest your energy in strategic work. I often try to focus my energies on things that will shape a team’s approach and thinking about a customer or problem over influencing a specific decision. To quote Jeff again, “Be stubborn on vision but flexible on details.” Prioritize details related to where the product is going, but be flexible on the specific ways of achieving the vision.
Prioritize decisions that won’t be measured
The third lens I consider is whether a decision will be measured or not. When I find a decision I disagree with, I like to start by asking, “How will we measure if this is right?” Facilitate what the hypothesis is, what data needs to be measured, and whether that data will accurately reflect the quality of the decision. Before running an experience, you should also know how your team will make decisions if you get competing data points (i.e. one metric is up and one is down). After gathering the data, it can easily bias your decision by looking at it in a way that suits your desired outcome. If a decision will be measured and my team agrees on metrics, then I can put less time and energy into debating specific choices.
Prioritize disagreements where you fully understand the context and data
Before picking a battle, I challenge myself on whether I have all the right details. If not, I’ll just ask questions like “Can you help me better understand X?” Or “Why would we do X over Y?” Or “Can you point me towards metrics or customer insights that will help me better understand this space?” Before disagreeing with something, I challenge my own beliefs on a topic to make sure I’m considering more than my initial instinct. This can be especially difficult if it’s an area I’ve thought about significantly or firmly believe in. Understanding the context and data for my disagreement will help me prioritize whether it’s a ‘fight’ I want to have and then when I engage, I have a better argument.
It’s okay to let others fail
A few years ago, I was in weekly brainstorming sessions with multiple VPs as we explored a new, complex CX. A senior manager was responsible for facilitating these meetings. One week he had dropped the ball on preparing, and I stepped in with a last-minute document to facilitate. After the meeting, my mentor and the director at the time shared that I need to learn to be comfortable with letting others fail. I didn’t want leaders to perceive our team as failing if we didn’t have the follow-ups we had discussed the following week. But I also prevented an opportunity for this manager to get valuable feedback on how to keep the work moving forward. I had stepped in because I wanted to see this product succeed and was worried that a poor brainstorm would reflect poorly on me. In reality, it would have only reflected poorly on the individual driving the meetings. As a wannabe perfectionist, I find it difficult to ‘let others fail.’ Yet, this is important for letting others grow and calibrating when you step in.
So, next time you pick a battle, ask yourself, ‘Who is responsible for this decision? Whom will the quality of this decision reflect on?’ If the decision is yours, then the battle may be worth fighting (given the other prioritization above). But if not, consider whether it’s worth disagreeing. Perhaps it’s okay for the other person to learn a lesson if your belief in it being wrong turns out to be true. Learn to be okay with telling someone, “I don’t agree, but this is your decision to make.” Use a neutral party (e.g., your manager) to understand if a group’s decision could impact your credibility.
So, that’s my advice on picking your battles. To summarize, my framework includes:
Focus your efforts on one-way doors or costly two-way doors. Spend less effort on issues impacting fewer customers and reversible two-way doors.
Rather than discussing individual ‘micro-level’ decisions, up-level your discussion by focusing on how you make decisions as a team.
When choosing which battles to fight, you can put less effort into measured decisions as long as your team agrees on the right inputs to measure the decision.
Don’t disagree unless you feel like you have all of the data and context to contribute. If you don’t, start by asking questions.
If someone else is responsible for the decision, use a softer form of giving feedback and be okay to let them fail if the decision turns out to be wrong. It’s okay to let others fail.
That’s all I have for today. Thanks for taking the time to read. I’d love to hear from you: How do you pick your battles? You can comment publicly or reply directly to this email. If there’s a topics you’d like to read, drop me an email. If you’re finding this newsletter helpful, I’d be grateful if you share this with friends.