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How does one cultivate the skill to "pick your battles"?

The Huffington Post The Huffington Post 22/03/2016 Quora
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How does one cultivate the skill to "pick your battles"? originally appeared on Quora - the knowledge sharing network where compelling questions are answered by people with unique insights.Answer by Mira Zaslove, product manager, on Quora.
Learning how to successfully "pick your battles" largely depends on your comfort level, the culture, and a calculated risk / reward equation.
When I managed a sales & trading team, a lot of my time was spent adjudicating battles within my team, fighting my own battles, and fighting my team's battles. To determine if a battle was worth fighting, I evaluated three main components: the culture, the battle, and the outcome.

The Culture:

1. How often are battles fought? Culture comes from the top, so gauge how battles are effectively picked, fought, and won by watching successful people at your company. Understanding leadership's view on conflict is the first step towards deciding when to pick a battle.

Aggressive behavior, like picking fights, that is celebrated for being "competitive" in some cultures can get you written up, or worse, in others. In some cultures you have prove your mettle or you will be taken advantage of. And in others, it's considered a breakdown in decorum to have even a remotely contentious conversation.

2. What is your personality? I don't like fighting and try to stay away from picking battles; however, there are times when it's necessary.

If you are someone who is drained by arguing, you'll need pick your battles carefully. However, you don't want to so selective that you get run over.

If you are energized by playing devil's advocate, and are someone who enjoys a good battle, then you can be less selective.

Finally, it's useful to take into account how are you perceived. Can you skillfully pick battles and still be seen as a "good guy"? Or are you someone who picks one fight and is forever labeled as "difficult to work with"?

The Battle:

3. What is at stake? Know what you want. Never pick a battle when you don't know what you want to get from it. Don't fight just because you are angry. Also, try not to fight against a person-- but rather, fight for the resolution to an issue. Make your desired outcome the best solution to the problem, not the cause of it.

Don't pick other people's battles. Unless you are their manager, don't actively involve yourself in other people's business. Everyone has limited capital to invest in battles and spending it on something where you don't reap any benefits and may not even have full context into the issues will eventually hurt you no matter how good you are with conflict.

4. Is the timing right? Timing is important and will depend on the situation. Some problems are easier to nip in the bud. For example, if someone is trying to take credit for your idea / steal your client / take your commission, it's much better to call them out immediately. The longer you wait, the harder it is to wrestle back control. Other conflicts require marshaling resources, evidence, and political support.

Don't pick a fight in the heat of the moment-- even if someone provokes you. You need to determine the tempo of battle. Never lose your cool. If someone loses their temper on you, use it to your advantage -- they'll often dig themselves into a big hole. If they catch you off guard, calmly walk away to develop your strategy.

Always be prepared with rational arguments backed by facts, statistics, precedent, etc. Frame your argument in terms of what is best for the company.

With many larger and more complex problems, it's typically better to wait. Gnarly conflicts often work themselves out or have no immediate solution. It's usually better not to pick a fight you don't have to.

Also, when applicable, keep in mind who is going to be adjudicating the battle. See things from their perspective. Time the decision making to their mood and approach them at the appropriate time.

5. How much leverage do you have? It's often useful to evaluate how much capital you have when determining whether to pick certain battles.

When you start out at a company, you get a small amount of capital based on your role, skills, etc. And the better you perform over time, the more capital you receive. For example, on a trading floor, where the bottom line matters most of all -- the more money you make, the more capital you earn. The more battles you can pick and fight. Similarly, when you lose money or battles, you lose capital.

Obviously every culture is different. In some environments, confrontation and picking battles will cost you capital whether you win or lose. But if winning begets winning and losing begets losing, carefully taking into account your capital and leverage at the company matters a lot.

If you are someone who rarely picks a fight, and has a lot of capital built up, then people will be more receptive to your side when you do. If you are someone who is always picking fights, then you can lose those battles you should win, simply because you are out of capital.

6. Who else is involved? Tread carefully when picking a fight with someone holding a lot of capital and/or leverage over you. Especially if they are an ally of yours in another situation, or if you need their help to get your work done. Also, don't pick fights with people you manage, or people below you. Punching down can be worse than punching up.

You are unlikely to win in a battle against the CEO. So it's usually best to trust that they know what they are doing and have more information than you do.

Similarly, it's important to get a pulse on public opinion and see who will back you up if asked. If the CEO, or another powerful ally, is on your side, you will likely win.

7. How far are you willing to go?  Sometimes, you can test the waters, "agree to disagree" and easily move on. However, some battles are impossible to stop once you've started them. Be careful of picking battles that can quickly spiral out of your control.

Keep in mind your Sunk Costs and know how serious the battle is likely to be, how long it will take for resolution, and how quickly / easily you can cut bait if you decide you don't want to fight anymore.

The Outcome:

8. How likely are you to win? If the battle is important, and you have a good chance of wining, then in most cases you should fight it. However, there are times when it's best to wait and re-evaluate -- even if you know you are going to win. For example, if it's going to upset an important ally, or take more time and effort than it is worth.

If you feel like you are going to lose, then you need to evaluate how much capital you have, and if you can afford to gamble with it. Sometimes it's necessary to make a point, and picking a fight is the only way to do that, even when you lose.

Similarly, some battles you need to lose, to win the war. If the battle is part of a larger strategy it's necessary to take into account the complete picture. Does this short-term battle play into a longer-term goal or is it an isolated event?

9. What is the likely outcome if you win? The bigger the potential gain, the more incentive you have to take action. If the stakes are high, and you have the chance to score big, then go for it. Bet it all, and don't back down.

If the stakes are low and you feel that nothing will change, even if you do win, it's probably best not to waste your time and energy. Don't expend more capital to pick a fight than you are likely to receive if you win the fight.

10. What is the likely outcome if you lose? Consider the worst possible case scenario. Can you handle it?  If not, then it's probably best not to pick the battle... unless the potential upside far outweighs the potential downside.

Ultimately, picking your battles is an important part of winning those battles. If you're in a culture where battles are important, then you need to cultivate the skills to:

  • understand yourself and the culture;
  • quickly evaluate the battle, including timelines and key players;
  • and accurately weigh the cost and potential outcomes.
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