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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?

Mike Haylon
Asana GM, AI StudioMarch 6

Welcome to the C-Suite. The people in this position have gotten there because they have really valuable perspectives to share and are often right. The best thing you can do being stuck in the middle is to be really clear about the decision(s) being debated as part of the proposed strategy, what the most salient points are that bolster or refute each argument and bring clarity on the decision(s) that need to be made and by when. Putting this into a document and asking folks to weigh in ahead of any meeting or debate can be a really valuable way to bring clarity to what's being proposed and ensure the sides are accurately represented. This exercise can also give both sides a chance to be sure they understand the alternative argument clearly and that their side is being represented in a way they would. It also gives the added benefit of bringing more voices into the fold giving them a chance to add data points or solicit perspectives that are important but might not yet be represented.

418 Views
Sarah Mercedes (Osborne)
HubSpot Director of SalesJanuary 25

First, seek to understand. What is each stakeholder's stance, but more importantly, why do they have that stance? What are their priorities, what are their concerns and what are they looking to accomplish with their vision of a given strategy? Once you understand that, it will be clear to see where their perspectives align and the conversation can flip from one of debate to one of solutioning. The key is making the conversation centered around solving for the priorities, concerns and goals of each party. Once there is alignment on those elements,you can present all of the options that fit that critiera and the parties are then sitting on the same side of the table selecting a path together.

2619 Views
Adam Wainwright
HubSpot GTM Leader | Building Products that help Sales teams win | Formerly Clari, CallidusCloud (SAP), Selectica CPQ, CacheflowMay 1

Alignment is the name of the game. And yes, Sr. Execs aren't always seeing eye to eye.

The good news is that Sr. Execs understand the unifying language of alignment.

In other words, try to figure out, in independent settings, how your proposed strategy serves the bigger picture. The strategic initiatives. Maybe they are around revenue growth or operational efficiency, or just getting things to work the way they should. In any case, your goal is to build a consensus that your proposed strategy directly impacts them at the strategic/executive level.

When discussing plans with Execs. Be brief, be bright be gone. That is. Have a point of view. Make sure its tested and ready for deep review. But don't worry about the details when proposing a strategy.

Instead make your case starting with the end in mind.

In a presentation format, this might sound like this:

  1. Getting to $100M across Services AND Customer Business (perhaps in this case Head of Services and the Customer business don't like each other)

  2. Efficiency, Speed, and Performance

  3. 2-4 Months - for Maximum return

As an executive of either business/department, I'm seeing something that directly impacts me, my team, the total goal (getting to $100M), a high-level representation of what we should be aligning on (Speed, Performance, etc.), and a basic timeline.

This is a very simple example, but if you can swtich the executives into Exec. think, they'll listen and they'll likely agree that alignment on the presented outcomes is what matters.

...but you gotta have a plan ... it needs to be baked and tested. So when tested, it stands up to scrutiny.

414 Views
Katie Harkins
Glide VP of SalesApril 28

Everyone in the career will be in a situation where you have 2 senior executives stakeholders who disagree with each other on your proposed strategy and you're stuck in the middle. It's only a matter of time. 

"Worrying is like a rocking chair, it gives you something to do but never gets you anywhere" -Erma Bombeck

Approach it like a sales cycle. Understand where both stakeholders are coming from and propose a strategy with concrete numbers and impact. What does this delayed decision do for the overall business? If it was a problem-tunity solved yesterday, how would that impact revenue?

371 Views