What's the best way to keep the leadership team engaged and continually contributing to messaging strategy and positioning?

If your leadership team understands the value of messaging, and how that can impact the success of an org, they will likely want to be involved without you having to ask! So the first step is to make sure that the leadership team truly understands what good messaging can do for an organization.

We made sure to bring our leadership along the journey as we revamped our messaging across all of our products and buyer personas, had regular check-ins and kept them updated on our process and progress. This ensured they were in the loop, that their feedback was incorporated, and also gave us the opportunity to talk about the data we were gathering to inform our messaging. 

Everyone loves data - so use it to your advantage. Whether its results of your market research, or data from A/B testing messaging in different channels - your leadership will care about all of it.

It's ultimately up to the PMM team to drive engagement and feedback on messaging. One of the easiest ways I've found to do this, is to link messaging discussions with launch planning. Not everyone on the leadership team is passionate about messaging, but I've found that most people do care, and want to be informed/involved with product launches. Use launch reviews as a vehicle to drive messaging conversations.

Like every other product marketing initiative, positioning & messaging programs should have executives' buy-in. I found that talking about business value and connection to the company OKRs works great. For example, 

• incorporating leadership opinions into messaging will help us drive better results for the strategic launch (user growth goals);
• adding competitors' differentiation or strategic advantages from the founder's POV can drive stronger product perception (awareness goals);
• founders' contribution to positioning /messaging will help align the company mission and external communication (part of OKRs initiative for this year).

Keep positioning and messaging strategy a key talking point during crossfunctional, stategic, leadership conversations. If its top of mind for leadership, and they understand the impact of effective positioning, they will continue to contribute feedback to it and care about it. Also, leadership cares about what the customer cares about. Voice of Customer and any friction, validation you can share will be essential. 

Stakeholder communications and management can vary widely in my experience working at start ups to some of the largest enterprises in the world (Disney). When you're working with a founder CEO who has a very specific vision for positioning and messaging, you want to make sure that you know all the history in the development of the company/product so you have empathy for her "why." However, I like to say that history is informative, but not prescriptive. You need to be aware of how your market, clients and competitors have shifted over time and ensure that your messaging is reflective of all those inputs. In smaller companies, you most likely already sit on the executive committee or at least have easier access to this group, in which case, I would recommend making sure you have time on whatever weekly agenda is available. I'm a data-driven person, so I would always recommend focusing any executive updates in the context - action - results format (regardless of the size of the company, this is the approach I take). If you're developing new messaging, what were your inputs, with whom did you speak, how did you test it, what learnings resulted and what actions are you going to take moving forward. The level of detail provided here should align to the levels of stakeholders you need to address - e.g. your immediate team, the next level up, then exec staff - and the frequency that's appropriate for the project or program.