Pick your Battles

Product Management lessons from the battles I didn't fight out

Alexander the Great had a trick up his sleeve that modern Product Managers can learn from. He didn't just conquer lands; he blended right in, adopting local customs and attire. This wasn't just a ploy to win hearts; it was part of his grand vision for a cohesive empire.

His Macedonian troops, however, thought he was nuts.

To them, he was betraying his Greek heritage and turning too Asiatic. After all, they had the muscle to subdue the Persians and Indians without the theatrics, hadn’t they?

But Alexander knew better:

not every battle is worth fighting. Sometimes, it’s smarter to bend and play along.

In business, we face this all the time. Fighting certain battles might seem noble, you might even feel entitled. But is it the right time? Is it the right environment? Do you have the power or influence to win?

As a Product Manager, it’s crucial to prioritize not only the JIRA backlog but also the battles you choose to engage in.

Here, some battles I decided not to fight in the past, both as an individual contributor and a leader, along with the alternative strategies I decided to follow instead:

Battle 1: Product Owner vs. Product Manager

Here’s a classic. The great title debacle of Product Owner vs. Product Manager. You’re grinding away, building value, and someone slaps the title “Product Owner” on you in official process documentation (which is not a job, but a Scrum role). Feels like a demotion, right? Like being called a “Junior Wannabe Astronaut” when you and your senior product management team have already walked on Mars. It stings.

But sometimes titles don’t matter, because there are bigger problems to solve — for instance, the process itself: who should be in a given moment responsible for backlog management? For once, I decided to let it go and focus on the results — delivering the promised value, no matter how.

Spoiler alert: nobody cares about your title when your product is successful.

Battle 2: Top-down feature requests

Next up, the common scenario: a C-level executive or the CEO herself drops a specific requirement in your lap. It’s not product-led, and product gurus would facepalm so hard they might leave a red mark. But challenging the CEO isn’t always wise — even though, ideally, it should.

As a Product Manager, you’re on the hook for the outcome. If it goes well, the feature requester basks in glory; if not, you’re toast. So, what’s the play here?

Run your Discovery process—label it Due Diligence. Understand what this new feature means for the organization, the legal implications, how to measure success, and all that jazz. You’re not gold-plating the CEO’s decision; you’re ensuring due diligence.

It’s like being handed a grenade and making sure it doesn’t blow up in your face.

Implementing Due Diligence with a twist

Here’s the playbook for executing "Discovery without losing your sanity:

1. Reframe it as Due Diligence. That’s the avoided battle from this lesson.

2. Reverse engineer the requirement: Unpack what’s being asked and why.

3. Impact Analysis and stakeholder input: Gauge how this new feature impacts systems, workflows, and user experience. Get insights from engineering, sales, customer support, and legal teams. They’ll highlight potential landmines.

4. Risk assessment: Identify assumptions and document potential risks. Technical, operational, and business—cover all bases. Be the pain in the ass: double-check the assumptions and ask.

5. Success Metrics: Define how success looks, beyond the obvious top-down command.

6. Alternative solutions: Explore other ways to achieve the goal with less risk or cost.

7. Documentation: Compile findings into a slick report. Present it clearly, focusing on key insights and recommendations. If you have a different recommendation than the original request, be crystal clear and leave a strong record of your posture in written form.

8. Sign-off: Get the right people to sign off your “due diligence” findings on impacts and risks, especially the feature requester — even if it’s the CEO.

Battle 3: The Security Checkbox

In the B2B world, customers sometimes demand features that aren’t worth implementing. But occasionally, a top-tier account—the kind that brings in big ARR—makes a request. Even worse, they fit your Ideal Customer Profile (ICP) and their request seem dumb: a redundant security feature that could introduce performance issues or increase costs. You try your best persuasion techniques, but they don't budge. Their InfoSec team has a checklist dictated by external auditors.

So, is your company willing to risk this account to that stupid checkbox? Probably not. So, deal with it. Raise your disclaimers, amend the contract if necessary; feature-flag it, make it a paid upgrade for other ICPs, and turn the dumb request into another revenue stream while keeping the customer happy.

Turning Compliance into a revenue opportunity

Here’s how to turn a compliance headache into a cash cow:

1. Understand the compliance requirement: Decode the compliance need and why it’s critical for the customer. That includes the cost of not doing it for the customer.

2. Evaluate feasibility: Assess technical impacts. Will it tank performance? Inflate costs? Document everything.

3. Cost-Benefit analysis: Weigh financial implications versus potential loss of the account. Usually you will need to escalate this decision to the executive level.

4. Feature flagging: Implement behind a feature flag. Turn it on for the specific customer without disrupting others.

5. Monetization strategy: Consider if this can be part of a premium offering. Bundle it and package it as a paid upgrade for other high-value customers. You can even make a marketing campaign out of it and increase the revenue that quarter!

6. Customer communication: Clearly communicate how you’ll address their need and what does it mean for their performance, costs, contract, and so on. Make sure they see the value and the trade-offs.

Battle 4: The Cassandra Mess

The book "Extreme Ownership" by Jocko Willink teaches that the best way to lead is to own everything that goes wrong, even if it’s not your fault. What if you warned about a risk months ago, but nobody listened to you, oh poor Cassandra? You escalated the issue, documented your concerns, and some executive owned the risk (and the wrong decision). When the inevitable disaster strikes, resist the urge to say, “I told you so.” Instead, take ownership of the cleanup. Be the hero. Everyone will know you were right. Next time, they’ll listen.

Navigating the Cassandra Mess

1. Document EVERYTHING: Keep a record of all warnings and assessments (the level of paranoia depends on how political your company is). That includes e-mails and Slack screenshots, because unfortunately humans get “full Lannister” when it comes to saving their ass.

2. Offer Solutions, not blame: When disaster hits, focus on solutions. Don’t be judgmental even if you would be right to do so. Position yourself as the problem-solver. Stay constructive.

3. Communicate clearly: Maintain open lines of communication with all stakeholders. Craft a mitigation plan. Provide regular updates. Overcommunicate. You will need to step in a bit more on the Project Manager shoes. Whatever it takes.

4. Reflect and adapt: After resolving the issue, conduct a retrospective. Identify what went wrong and how to prevent it in the future. Do that with all the people involved in the problem since day 1. But most importantly, reflect on your own approach: what can you do next time to make sure you are listened to? How can you improve your communication and persuasion skills?

Battle 5: The Cultural Fit

If you’re forced to avoid so many battles to preserve your energy or mental health, you might think you’re in the wrong place. But there’s no perfect company where you always get your way. It’s childish to think so, even if you’re right. Changing a company’s culture takes a lot. As a PM, you can influence and shape it, but without the right sponsorship and empowerment, you might burn out.

Ask yourself if this is a battle worth fighting, or if you are willing to wait to see your seeds blooming. If not, consider moving to another company or starting your own.

Navigating Cultural Fit

1. Assess the culture: Understand the company’s culture. Identify strengths and weaknesses.

2. Identify allies: Find like-minded individuals who share your vision and values. Build meaningful relationships with them.

3. Focus on small wins: Start with small changes that demonstrate value. Success breeds momentum. Momentum breeds change. It’s like the butterfly effect.

4. Seek sponsorship: Get backing from higher-ups who can support and advocate for your initiatives.

5. Know when to move on: If cultural fit isn’t improving and hinders your success or professional happiness, consider other opportunities. Life is too short.

These are just a few examples, but I am sure there are many battles not worth fighting. What are yours?

Stoicism or Cowardice?

Balancing giving up on a battle and fighting it is tricky. Product Management, especially leadership roles, requires constant fighting with a knife between your teeth. Experience or a mentorship will help you gauge when the energy required is worth the investment.

Sometimes you need the injustice to explode in the face of destiny. But some problems get worse by not facing them or delaying them. And sometimes, you need someone to give you perspective and act as a coach.

If you need me, I offer one free coaching session a month:

Influence

Pushpin this:

the more influence you have, the less you need to worry about battle-picking.

Influence comes with time and showing your skills and strength, especially in the non-fought battles like the Cassandra Mess. It also involves personal development, like persuasion skills, and sticking to your values, especially honesty.

If you are struggling with battle-picking too often, you need to focus on building influence and trust across your organization.

I will dedicate another post to elaborate on how to do that, as well as some practical examples like the ‘Embrace and Amplify’ technique, which works 100% of the time.

Stoic Principles applied

Since this is all about Stoicism, I will remind you on what are the principles we are trying to keep rolling when picking our battles:

1. Focus on what YOU can control NOW: This is the core of Stoicism. Direct your energy towards aspects of the situation you can influence and let go of the rest. Time your focus.

2. Practice perception: Train yourself to see situations clearly without emotional distortion.

3. Prepare for adversity: Expect that not everything will go your way. Being mentally prepared for setbacks helps handle them better, especially if your prophecies come true — those sting the most.

4. Reflect and adapt: Regular reflection on your actions and their outcomes helps in continuous improvement. Adapt your strategies based on what you learn.

---

Alexander’s strategy of adopting local customs to win over conquered populations was about the bigger picture. If Alexander could dress like his enemies and marry their daughters, why are you battling with your colleagues and customers?

Choose your battles wisely, adapt when necessary, and focus on the larger goal.

Stay Stoic, stay Strong.