How to Deal with "Sinatra" Stakeholders

How to deal with a common kind of stakeholders that we may refer to as the "Sinatra" type. You know, the ones insisting on doing things "their way."


No matter how much we’d like for our Product Management role to be solely focused around building great products and making customers happy, the reality is that we need to work inside organizations. We’re part of a larger team and that means interacting with a broader group of people with direct or indirect interest in the product: our stakeholders.

I wrote about dealing with unresponsive stakeholders in the past, but there are many more personas to consider. A very common kind is what we may refer to as the “Sinatra” stakeholder. You know the type: the ones insisting on doing things “their way.”

These stakeholders manifest themselves in different situations. They’re determined to get some idea or feature unto the product, because they’re convinced it’s the right way to go. Maybe they disagree with what we’re currently working on, and believe we should change our focus. Perhaps they just want to see things released more quickly, instead of following some product process. Beyond these, you can certainly think of plenty other situations where you’ve been faced in some form or another with someone asking you to “just do it my way.”

The Cause: Misalignment

We should realize that “Sinatra” stakeholders are actually a symptom of organizational misalignment. They’re a sign that there’s some kind of disfunction going on. Consider just some of the reasons that might lead someone to insist on their own ideas above others…

  • They might be oblivious to the current product vision, strategy or overall value proposition. On the other hand, these things often don’t even exist or are clear enough to the organization. Amidst this absence of information, it’s natural that some kind of “everyone for themselves” culture emerges.
  • When people are not involved in the decision-making process, they don’t have all the information nor are they aware of the constraints and trade-offs that led to those decisions. It’s much harder to understand or agree with something without all this context in hand[1].
  • Something that’s easily forgotten is that stakeholders have their own jobs and things to care about. Thus, it’s only natural that they aren’t aware of which product processes and best practices we’re trying to implement. Without this information, it’s hard to understand why “the thing that’s most important to me” isn’t getting done.

In their excellent book, The Power of Alignment, George Labovitz and Victor Rosansky describe the concept of Alignment as an equilibrium between four factors, along two dimensions. First, vertical aligment refers to how the organization’s Strategy is communicated to and accepted by its People. Second, horizontal alignment relates to how the company’s Processes are geared towards delivering on the needs of its Customers. They write:

Neither a great strategy nor the full commitment of managers and employees will have the right result if a company’s processes for creating and delivering value have targeted the wrong customers—or worse, if they have targeted the right customers with the wrong product. (…) Nor will the company that is fully aligned on the horizontal dimension succeed if its strategy or implementation is wrong.

Organizations should then strive to be aligned along both dimensions, creating a dynamic relationship between all four elements. Each supported and strengthened by the others[2]. Here’s a useful visual representation the authors use:

The 2 dimensions of alignment. (c) 1997 by George H. Labovitz and Victor I. Rosansky

Going back to the reasons leading stakeholders to behave like this, it’s easy to see how they reflect poor alignment on both the vertical and horizontal dimensions.

There’s a lot to be said on this (very rich) topic and approaches to solving it. However, I’ve found that the #1 thing that helps Product Managers to align stakeholders around them is to involve them throughout the product development process. With this, the occurrence of “my ways” becomes much more infrequent.

How Involving People Leads to Better Alignment

Making sure that everyone’s on the same page is the key to avoid random, opinionated, and self-serving requests. The leeway we have as PMs may be limited in terms of changing the overall organizational culture. Yet, what we can do is affect the culture around our product. In this regard, aptly identifying and involving the product’s stakeholders throughout the development cycle is the most effective tool we have.

I know what you’re probably thinking and I do realize that this can feel cumbersome, overly political or pointless. It’s not. It’s the kind of investment that can help us bring the product out the door with the least amount of unplanned, internal friction. There are already so many things that can go wrong when building a product; why add internal resistance and struggles to the bill?

Involving stakeholders means multiple things:

  1. Seeking out their goals and motivations;
  2. Effectively communicating the product’s direction;
  3. Having them participate in the decision-making process;
  4. Keeping them informed of the product’s progress;
  5. Evangelizing the product processes and best-practices you follow.

Let’s dig a bit further on each of these.

1. Seeking out their goals and motivations

Having a clear understanding of what other people in the organization need from the product is the best way to explain how and why you can or can’t help them. This is about meeting with stakeholders, knowing where they stand, what they need and getting their input. Proactively doing this sets the tone and buys you some support from them.

It’s important not to take requests blindly. People often have either too concrete or too vague ideas of what they want. For the former, work your way up until you get to the underlying goal and motivation behind the request. For the latter, narrow it down and focus on the value they expect from this idea. Drive towards the problem they need solving.

2. Effectively communicating the product’s direction

Through whatever process, you got to some plan for the product’s direction. If some stakeholders were not part of this process, you have to share it with them.

There needs to be a widespread understanding of the current goals and strategy, but also the constraints that led you to the trade-offs and specific plan you’re now following. Being aware of these factors is what allows people to see the why behind our current path. This doesn’t mean they agree with it, which leads to us to our next point.

3. Having them participate in the decision-making process

As we just discussed, sharing the full context that influenced a decision is important to get others to understand it. But if we want people to be bought-into and committed to some strategy, they need to be part of the process that sets it. Otherwise, they’ll feel alienated, more easily oppose what we do, and come up with their own solutions.

“Decision-making process” is a catch-all term, and its meaning will be different from team to team. The important thing here is to include stakeholders in such a way that their needs are considered, they’re aware of all the constraints we have and they help make the necessary trade-offs. This is the way to move from “you decided this” to “we decided this.”

4. Keeping them informed of the product’s progress

As you move forward, spreading out the right information to the right people at the right time is critical to send a clear message that you care for them and are doing what you can to deliver on what was planned. This kind of openness ultimately helps you get stakeholders on your side if/when you have to deliver bad news.

Remember that every communication medium is different and serves a purpose. Always be sensitive to what will be most effective for the thing you’re trying to say and what the other person expects (e.g. don’t send an email if you need to soften the blow or ask for important feedback on a noisy channel where things can get lost.)

5. Evangelizing product processes and best-practices you follow

One final way to involve stakeholders is to be an evangelist for the product processes and best-practices we’re trying to follow. It’s often the case that when people don’t understand why we do certain things, they will try to sidestep them…

Why waste time validating this idea? Our competitors are doing it, so it’s clearly valuable

Why do you want to spend time on unit tests for such a simple feature? Just ship it to Production, we need it now!

No need to go to the designers for this. Just add this button-so-and-so and that’s it

It might seem odd in this day and age, but there are many stakeholders that don’t know about (and thus don’t see) the value in these practices and what happens when you don’t follow them. When working in these environments we should embrace another responsibility as part of our role: educating and getting people around us to be on board with “the right way” of building products[3].

Organizational alignment is just another metric to improve

This process never ends and can always be better. How you approach it and the things you need to focus on may be different, depending on your specific organization and stakeholders.

Still, there’s one key take-away: these stakeholder attitudes don’t come out of the blue or from malfeasance. They result from misalignment and even when you can’t change your entire organization, you can definitely affect change around your product.

If you want to look at it in a very Product Manager-y way, think of Organizational Alignment as one more “metric” you need to track and improve over time.

  1. Most of us are guilty of this, by the way. Think about how quick we often are in criticizing government officials that take decisions we disagree with. We aren’t fully aware of all the pressures, constraints and possibilities they had at the time. And still, our assessments are based on the information we glean from the press and what various political actors say and do. This is hardly the entire picture. ↩︎

  2. The book goes on to describe many different types of problematic organizations and how to drive them towards full alignment. ↩︎

  3. There’s a lot to be said on this subject. We need to be extremely tactful to avoid coming across as condescending or passive-agressive. Topic for another article. ↩︎