Knowing that people in different functions and different levels of leadership often need different approaches to storytelling in decks, docs, and shareouts for key strategic projects, do you have any tricks for thinking through whether it's worth the work to "reskin" docs and decks for these diverse stakeholders?

Not necessarily. The goal is to ensure that for whatever initiative (launch, pricing, campaign etc) youre leading, the north star is clear, expectations from each member (or group) are clear, and the communication is very clear. The only group that usually 'needs' their own reskinned decks and docs are senior leadership. They usally get packaged updates that are much more streamlined with a focus on updates, risks and asks.

If you have other stakeholders that are asking for their own format, Id encourage you sit down with them ask why. Its a huge burden on you to make multiple documents, so the best approach is to figure out a middle ground.  

A few tips:

• Before starting the project, get everyone's buy in on their role in the project. Use a RACI if that's the culture, or at least a simple document saying if someone is in the 'working team', 'approval team', informed/consulted team etc. This will ensure expectation management up front. If someone comes up later saying 'why wasnt I involved' you can show them the paper trail to explain no malintent
• Drive home this divison of responsibility in your kickoff call (as in HAVE a kickoff call for sure)
• Ensure that everyone involved is on the recurring meeting invite, Slack channel, Teams group, whatever you use for comms and accountability
• If you have a top down culture, explicitly build in meeting cadences for review, approval, stakeholder feedback and call it what it is. Dont assume that people will know things, or pay attention 'offline'
• Over communicate -- pre-meeting, agendas, status boards, recapss. Call out what's stakeholder relevant, whats not

No easy way to do this, but its a lot of cat herding that if done well can drive massive organizational alignment.

Part of our jobs as PMMs is to drive alignment across teams of diverse stakeholders, all of which speak different languages, care about different things, and want to be approached in a specific way. When it comes to key strategic projects, I believe that tailoring your approach to meet the needs of your stakeholders is critical to achieve maximum success and collaboration!

This could be as simple as reframing certain elements of a master deck/doc you’ve created for a key strategic project. Depending on who you’re communicating with, identify how you can adjust your project updates to ensure those particular stakeholders find your work important and valuable. For example, marketing may care more about how you helped them generate more high quality leads vs product may care more about product/feature adoption. No matter who it is you're communicating with, identify their key measures of success and think about how you can align your outcomes to their objectives.

If you're trying to assess whether you need multiple versions of an asset like a first call deck or pitch deck, the best thing to do is to sit with the different groups of people you're trying to build for and see if they actually do present the same content differently. Maybe the CEO uses the more visual slides and skips the slides with bullets on them or maybe an experienced sales person shows a slide with bullets but says different words compared to a new sales rep who "reads" the script closer to verbatim. Either way, it is valuable to gather as many examples as you can. Ideally you have a conversation intelligence solution like Gong or equivalent so you can review multiple recordings.

If you decide that the various different people or groups are using the same deck differently, then it makes sense to create multiple versions. You might have one version for the CEO or execs and another for sales. But the best thing to do is to gather the info by being in the room or at least listening to the recordings!

Another thing you might learn by doing that research is that even the same person delivering a deck to different audiences changes how they use it. For example, maybe a salesperson uses the deck differently when they are selling to a greenfield opportunity vs. one where they are trying to displace a competitor. Again, research research research!!