How do you work towards win/win situations with stakeholders who's top-line goals are inversely correlated to your top line goals?

I love this question! It happens a lot and working through it is part of our role as PMs. There are a few layers to my approach here:

First, start with building the relationship. (I hope this theme is clear by now ;-). While your goals may conflict, at a higher level you are playing for the same team, and having constructive, trusting relationships is a key for any team’s success. You don’t need to agree, but at least seek to understand and show empathy.

Second, focus on higher level framing, rather than your own goals - You both want the company to succeed, and if you start double clicking into what success means, you will likely be in agreement for the first few clicks. As you go deeper, call out the framing e.g. “We want to grow revenue, but also want to ensure good customer satisfaction. We may disagree on the relative importance of those factors”.

I specifically recall a leader I worked with with whom I philosophically disagreed on the overall direction of my product, but could still have very productive conversations about how to think about the space. We were not trying to persuade each other, but rather use those conversations to enrich both of our thinking.

Third, As you lay the framework and get to the crux of the disagreement, try to think of the “what needs to be true” statement. If two reasonable, capable groups of people look at a problem and get to a different conclusion it may be because they put different “weights” on different considerations. You can then enumerate “A is better than B if X, Y and Z are true. Otherwise B is better than A”. Example: Driving revenue up by X is more important than driving customer satisfaction up by Y if we believe that the change in customer satisfaction will lower attrition by XX and drive increased spend fro existing customers of YY”. Then the discussion can be about the conditions, not the goals.

Fourth, when the discussion does move to goals, look at counter metrics. “Grow metric X while keeping metric Y within certain guardrails”. I’ve seen this technique used a lot at Meta.

Last - Escalate. I encourage my teams to escalate disagreements so we, as a leadership team, can unblock them. If the work above does not solve the challenge, at least it allows for a very structured discussion among the leaders of the conflicting parties.

If you do feel that goals are inversely correlated, I believe it's important to outline the impact of a potential solution on the other person's goals and on your goals. There will be solutions where the impact on someone else goals might be greater than the impact on your goals, and that might be acceptable.

However, what you don't want is a watered down solution which doesn't meet your goals or that is detrimental to the customer or your organisation. In this scenario you need to be able to explain why you're saying 'no' or rejecting another solution. I typically double down on aspects such as customer value and business results, both to keep myself honest and to negotiate effectively with stakeholders.

This one is interesting. 

If your goals are truly inversely correlated, I'd say there is something wrong with the top-line goals. That would suggest misalignment or lack of clarity higher in the org.

If it's more a case of mismatch in focus—say, your primary goals are around customer retention, and you're collaborating with stakeholders from sales—you want to optimize around lowest-effort, highest-impact projects for that team. You're going to spend the majority of your time and resources on current customers, but you want to partner with sales to understand what those low-effort, high-impact projects might look like. Funnily enough, identifying small efforts like these typically requires more collaboration up front than the big ones do, but they allow you to support your stakeholders while putting the majority of your team's resources toward your primary goals.

First, if you truly have stakeholders whose goals are 180 degrees opposite from yours, that's an alignment problem in the organization's executive leadership team and you have to decide whether that's something you believe you can change. But in my experience it's rarely this clear cut. Nobody has a product team that's trying to increase revenue only to have a sales team that's trying to minimize revenue, for example.

More often than not it boils down to a conflict between things that appear mutually exclusive but aren't. Take, for example, the common conflict between PM & engineering on reliability versus velocity, as embodied by (frankly unhelpful) maxims like Mark Zuckerberg's "move fast and break things". Actually, it's possible to move quickly and not break things, just as it's possible to move slowly and completely hose systems.

The best technique I've found for creating alignment and avoiding silo-versus-silo local optimization is to plan the business using one planning document that surfaces everyone's initiatives. I've used a single V2MOM (vision, values, methods, obstacles, metrics) document that makes all work visible across a product area. Engineering needs to redesign something for scale? Put it on the V2MOM. Design wants to spike on an area of the product that's causing significant user pain? Put it on the V2MOM. Need to conduct discovery (research) in an area? Put it on the V2MOM with its exit criteria. And so on. OKR is a similar system to V2MOM with the same forcing function that if a team decides to do something (objective), the goals defining success for that objective (key results) have to be internally consistent.

One other important thing when writing planning documents is to number all lists. Numbered lists force prioritization conversations because literally item n, by virtue of appearing at position n, is more important than item n+1. (In other words, if we only had time to do n items, items n+1 and on would not get done.)

1) See if its truly inversely correlated in all dimensions. It is likely there are some dimensions (e.g., customer hapiness) on which you have similar objectives.

2) See if you have common objective in the long term. For example, if you are working on a feature that will reduce the usage of your product, your long term objective is still likely to get increased usage.

If the above still doesn't work, align on common organizational objectives. 

This sounds glib, but you have to fix the goals. You cant achieve win:win when the goals are misaligned. 

If you and your internal partner are empowered to change the goals then you need to do the work to pick a new shared team goal. Having misaligned goals is just brutal to people and teams. This is also a great exercise in thinking bigger and more about company/customer/business goals vs. team/individual goals.

If this is out of your control, then escalate ASAP. Escalation is not a bad thing. Senior leadership is there for this reason, and great leaders would recognize this as their duty and responsibility to solve and will appreciate you raising this issue so they can unblock you. 

In my experience, time horizon and top customers can be the two biggest drivers of conflicting goals. Examples:

• Product is building tomorrow's vision – but Sales and Customer Success need to sell what is in the product today. As a Product leader, it can be challenging to justify working on feature iterations and bug fixes when you are also expected to deliver a completely new experience that will solve or negate those code red issues in a few months. The main questions I ask in these situations are: Which features or experiences do we expect to remain consistent from now to then? Are there dependencies that can be tackled now that will help us make the future vision a reality?

• Measures of success for various stakeholders may be dependent on different customer segments. As a result, the Product team may have to manage mixed signals when it comes to prioritization. In this situation, I would look toward the corporate strategy or long-range forecasts to understand which segment the company expects to drive growth in the next 1-3 years. I would also look at which features or experiences are common across customer segments, as a way to consider prioritizing problems with the broadest impact.

If your higher ups are optimizing for rational goals delivered thru the product you are building, then thats great. If not, then its them who are having a hard time curating the right objectives for the company.

So, to answer this question and minimize this, focus on the bigger picture: the shared company objective.

So identify common ground, whether it’s growth or customer success, and frame your goals within that.

For example, if you decide to involve the engineering team instead of the design team in a project, you should explain how this choice will lead to significant benefits for everyone involved.

Next, develop a mutually beneficial strategy that aligns both sets of goals. Often, stakeholders overlook the long-term impact of short-term wins, so position your approach as the path to sustainable success.

To this end, data is your ally, show how hitting your objectives positively affects theirs. Over time, build trust by consistently delivering value to their goals.

There are many nuances that go into this dynamic and no answer will fit everything but this should be a good ground for all of you.