Sometimes you need to wear rose colored glasses ….

1. Email is a terrible way to advocate for change. Too much can go wrong.
2. Don’t assume that someone who complains about something in private, is prepared to advocate for change in public. Pick your agitators wisely.
3. Craft the change you want in terms accessible to the business. How will this improve/create business outcomes? This is a no-brainer, but I always amaze myself by how often I leave out the Why, and connect that to my proposed How/What/Who. I assume the connection is self-evident.
4. Remember that the system is perfectly optimized for something. That something may be the perfect balance of two opposing agendas. It is tempting to identify that tension as instability (and a situation ripe for disruption), but the butting of heads can be perfectly predictable, and intractable. Put another way, don’t assume discord equates to an opportunity for change, and don’t assume “this makes no sense” means it truly makes no sense. Also, realize that a single goal — a promise to grow at a certain rate, for example — can obliterate and overshadow all other needs. Nothing else is important, even when people say it is. Ask yourself … what is this system truly optimized for?
5. Be prepared to leave. Some things aren’t worth fixing. And some things are fixable in ways that will be dissatisfying to you personally. Speaking for your own needs can be far more powerful than “speaking for” others.
6. Understand that 95% of all conversations with executives involve someone 1) complaining about someone/something, and/or 2) advocating for a pet project and asking for resources. Advocating for bottom-up continuous improvement is problematic because it implicitly suggests 1) something is broken, and 2) you are advocating for a scary and unpredictable “way” involving empowering the plebeians and cutting out managers. It feels non-actionable …the typical reply is “I want solutions, goddammit, not problems!” As an alternative, don’t ask for permission. Say “we’re trying [some thing] to see if [some outcome], and we’ll measure success by [some benefit].”
7. Go as high up the ladder as possible, but keep it brief. In line with the point above, understand that most senior executives are sick and tired of the political mayhem below them (even when they are the key reason it exists). They’re just waiting for someone to speak straight with them (even when their response to straight talk is to crush it into oblivion). Use this to your advantage, and make it count. Give them a back channel to what is “really happening” without overwhelming them or coming off as overly vested.
8. Remember that executives are being peppered with new/shiny “ways” 24–7. Why aren’t we doing [some fancy way]? This 1) implies the company is behind the times, and 2) implies that you think that by merely adopting a “way”, everything will be OK. Execs hate the idea that similar companies are absolutely kicking their ass by adopting simple practices (and creating the trust/safety to try new things). So…de-buzz-word everything. Don’t mention that Google has had success ___________________.
9. Realize that you will be accused of trying to “convert” people. It is critical to let a movement build steam organically and to avoid becoming a figurehead. Distributed and decentralized works best.
10. Keep in mind that any given time there are various leader/manager change initiatives in the works. In fact, you could argue that the status quo is a function of competing change initiatives. Bottom-up change initiatives compete with the established “long games” played by executives, and are therefore viewed as a threat/distraction. The desire to take credit for change, and to cast change in one’s particular image, is somewhat universal…and very common among executives (to the point of sacrificing overarching business objectives). As a start, map who is trying what (and why), and realize that you’ll likely need someone to perceive gain/advantage by supporting you, or, at a minimum, by not stopping you. Also, be honest with yourself. Are you advocating for change selfishly, or would you be happy if an expected behavior emerged?
11. As an extension of #10, respect the degree to which execs fashion a professional self-image that REQUIRES them to come up with this stuff. This — these big bold changes — are why they are there … not stuff a bunch of front-liners can do by regularly inspecting/adapting. Tread lightly. Your motive might be to improve the working conditions of our fellow contributors. But your whole career doesn’t hinge on the perception of control.
12. Make something work on a small scale. It’s easier, and will play to the universal desire for “good news” and “bright spots”.