How do you ensure alignment when you have two senior executive stakeholders who disagree with each other on the proposed strategy and you are stuck in the middle?

Startups are unique because (virtually) every employee is also a shareholder. Which means that every internal meeting is also a shareholders' meeting. Now, unlike companies where you are a passive shareholder (Grandma bought you 10 shares of McDonald's, for example) but have no way to influence day-to-day decisions, you get to make a big difference at the company where you work. Every day at a startup is a chance for you to make an impact that will increase the value of your (and your colleagues ...Read More

This is where DACIs (or RACIs) decision-making frameworks are critical. At a projects inception, it’s important to agree with senior executives on who the single final approver should be. Who is accountable for the success of the project (ie. whose job is on the line if it succeeds/fails)? Agreeing on the one approver in the beginning should prevent downstream conflicts. If you are stuck in the middle, the best you can do is offer objective data for both sides of the argument and leave it up to ...Read More

Goes back to the shared goals - which at a high level, are hard to argue with - revenue, cost savings, customer success, etc. Once you get that common agreement, then it's about the strategy / the "how" to get there. If there are disagreements here, I would start with trying to understand why and seeing it from both of their vantage points. Then trying to see if you can get them 1:1 to understand the other point of view or better yet, get them to talk to each other. Ultimately though if all that ...Read More

Oftentimes, disagreements are simply differences of opinion, which exist because there is a lack of data. In this case, PMMs are great neutral third-parties who are well-positioned to close that data gap. Listen carefully to what the execs are saying, and understand the WHY behind their disagreement. Are they disagreeing on strategy because one of them believes that the decision will make you uncompetitive in the market? As a PMM, you can bring competitive intelligence and customer insights to b ...Read More

This is definitely a challenge most PMMs see themselves in. I typically find success when I work the challenge from both ends. If the executives cannot disagree and committ while in the same room, spend time with each one individually. Understand their concerns, their perspective, and their reservations on an indiviudual level. I find that often many people are speaking "different languages" and the disagreement is somewhat superficial. It's your job to frame the strategy in a way that appeals t ...Read More

Sunny, Eileen, Sherry, and Roopal have covered the structural tools well. DACI frameworks and escalation paths matter. The thing I would add is what happens when the disagreement is not really about strategy. It is about territory. In my experience running PMM across organizations at Microsoft, Salesforce, and now at the Sr. Director level, most of the strategy disagreements that land on a PMM are actually executive boundary disputes wearing the costume of strategic debate. One exec owns revenue ...Read More

This is a tough one! It can be really difficult when you have exec stakeholders who aren't aligned. Ultimately, it's on them to get aligned and provide clear direction 'down the chain' but a few things that could help: Understand where the misalignment is - is it the whole strategy, or specific parts of it? Is there a compromise you could propose that would help get alignment? What are the main concerns of whoever isn't on board, and can you ask questions to better understand what is driving the ...Read More