Key questions to ask yourself before engaging your business politically

1. Where are you in the power structure? Are you high up in the pecking order? You can likely speak more freely if you are higher up, but you have more to lose. Are you lower down? You might find it harder to speak freely, but you have less to lose.
2. Do you possess emotional control? Politics can touch nerves and make otherwise reasonable people lose control of their emotions. Know yourself to guide yourself.
3. Does the medium matter? Personal or digital? Sometimes, politics is something best discussed in person where misunderstandings can be more easily avoided and the bounds of congeniality are more apparent.
4. Are you new in business or to your position, or not? The longer you’re in business, the more frank you can be about your political inclinations – it’s likely you’ve settled within a supportive business ecosystem. If you’re new to your business or position, however, you’re more vulnerable to being shunned by those who disagree with you.
5. Does it matter who or what you support? There are degrees of extremity when it comes to political positions. Most people will openly support public education for children, whereas fewer people openly support LGBTQ rights.
6. Is there a difference between Party Politics or politics? Supporting a Political Party can have you aligning yourself to a basket of different positions, some of which you may or may not agree with. It might be more congruent to support specific or aligned political positions instead of political parties.
7. Does it depend on your customer’s views? You’ll be safer speaking if your customers, by and large, support the views you espouse.
8. Does it depend on the product you sell? Some products easily lend themselves to aligned political positions whereas others have only tenuous relationships with broader policy. You might enjoy more congruency in your political positions and your brand if there is a natural link between them.
9. Does it depend on how many customers you have? The more customers you have, the more likely it is that you’ll unknowingly offend some of them. On the other hand, if you have fewer customers, it’s likely you’ll know them better and will be able to better predict how they will react to your political leanings.
10. Does it depend on how good your product is? The better your product, the more easily you can afford to align yourself with political positions – most people will continue to buy from you whether they agree with you or not.
11. Does it depend on how weak your competition is? If your products are leaps and bounds better than your competition, the less likely it is that customers will switch.
12. Does it depend on your customer’s demographics?
    • Education. More educated people tend to be more progressive, less educated people tend to lean more conservative.
    • Age. Younger people are more progressive, older people are more conservative.
    • Gender. Women are more likely to be progressive while males are more likely to be conservative. With that said, there are many men and women that fit into every slice of the political spectrum.
    • Socio-economic status. Those with high status tend to want things to remain the same, whereas those with less status want more change.
    • Race and ethnicity. Minorities tend to be conservative (when it comes to religion or cultural issues) and more liberal on other issues like equality of opportunity.
    • Regions. Rural regions tend to be more conservative while urbanites tend to be more progressive.
13. Does it depend on whether your position is middle of the road or extreme? Middle of the road positions are easier to take whereas extreme positions can be risky.
14. Does it depend if your position is against or with the tide? Adopting a popular position might show that you’re one of the crowd while adopting a less popular position may make you appear out of sync. Further complicating matters, it’s important to consider that the tide may someday turn.