How have you found success managing stakeholder relationships when there’s a wide gap in communication styles?

I’m not sure if this is in regards to a wide gap between how you communicate vs. the stakeholder, or a wide gap in how multiple stakeholders who you manage communicate. 

On the first topic, seek out others in the business who communicate well with the particular stakeholder. Don’t be afraid to address it with them directly too. If you don't have someone else to learn from, trial and error works too. Sometimes I see people try the same type of communication over and over, even if it's not working. The important thing here is to be intentional - try one tactic, and if it's not resonating, try another. This applies to everything form format used (e.g. phone, Slack, email, meeting) to reasoning (quantitative vs. qualitative) to level of detail needed.

On the second topic, if you’re managing multiple leaders that prefer different communication styles, there are a few options. One is to use all the avenues and cater to the individuals. This can be a big lift, so I’d see if there are maybe ~2 that the group can align on (ex. maybe a meeting and a quick follow up email with action items listed). Another tactic is again leaning on others to help overcommunicate. For example, we rolled out our internal roadmap and shared it via email/doc and held office hours to discuss live with anyone who would prefer to chat (2 different formats). We are still constantly referring back to this - it’s linked in multiple docs, we continue to refer to it in stakeholder meetings, etc. Utilizing others to help communicate and spread the word is a scalable way to overcommunicate.