The Art of Disappointing OthersNovember 7, 2014

Most people won’t recommend disappointing the people you report to as a strategy for furthering your career. It’s simple: your boss or the board you report to are to be pleased by your work, not disappointed. Right? Not necessarily.

I want to share with you why disappointing the people you report to can be more efficient in garnering greater respect and demonstrating larger capacities. I call this The Art of Disappointment.

The first thing to understand is that supplying the people you report to with what they want is not a wise strategy. It communicates complacency. Yes, this strategy yields a particular kind of trust—but one that is rooted in dependability.

Merely executing on the expectations of others who hold organizational power over you demonstrates a lack of vision on your part. It means you can’t lead yourself.

Fulfilling the vision, agendas and desires fashioned by others demonstrates you’re a solid employee but not a worthy leader. Be too consistent in merely following your marching orders, and you’ll be communicating a message you might want to carefully reconsider before sharing it with the people who determine who gains new responsibility in your organization.

Now for those reading this who don’t have the ability to consistently execute on the demands handed to them, this isn’t for you. Don’t get ahead of yourself. This message is for those who’ve already spent many years delivering solid, predictable and valuable work day in and day out. While many people want to skip some steps along their professional development in the hopes of getting ahead faster, premature deployments of complex strategies can have undesirable outcomes. Consider this your warning.

But for those of you who know the heart of discipline, sacrifice and commitment and are ripe to take your professional development to the next level, this is for you:

#1. Get Good Intel
Imagine you’ve just been handed a new project or initiative. Your first job is to get good intel, right? Most people understand “intel” as getting details on the scope, timelines, expectations and deliverables as it pertains to the successful completion of the assignment. But this is only the starting point.

If you’re only getting intel on the project or initiative as it pertains to your job and your successful execution, you’re prematurely leaping into action. Instead, spend more time with the board who’s provided the direction. Take more time with management or leadership to get more details. You need to understand the project or initiative from multiple vantage points as it relates to others and the organization as a whole.

In order to lead, you must be able to see the project as it is viewed from multiple reference points in the organization—in other words, perspectives other than your own. These vantage points include your boss’ or the board’s vantage point on the new initiative, both of which are essential for you to grasp with clarity.

Remember, you’re not merely interested in the intel of how your boss describes the project to you. Rather, you’re interested in how they hold this project in their own mind. Sometimes you can ask directly and they’ll tell you. Other times, you need to do some political and relational maneuvering to get those with more organizational power and perspective to share these insights with you.

Once you succeed in learning your boss’ vantage point, you need to triangulate. Ask yourself, “How does another executive view this project? What are my peers saying about this initiative? What does this project or initiative mean to the end users, customers and key shareholders?”

Get good intel. The reason this move is so critical is because the last thing you want to do is attempt to employ the art of disappointment if you are only relying on your own vantage point for your understanding of the project’s scope.

#2. Assemble Your Strategy
Leadership and elite performance in organizations does not merely stem from the ability to gather good intel from multiple positions inside of an institution. It’s generated, at least in part, by your ability to see the organization from “the outside in,” as Harvard Professor of Adult Learning and Professional Development, Robert Kegan, explains.

Seeing the organization from “the outside in” means that some part of you must be able to mentally stand outside of the organization, look in, and see how your new initiative fits and does not fit with the existing people, policies and practices. In other words, you need to be able to see the bigger picture with an unbiased perspective.

This means you’re able to see the larger systems inside of your organization. It means your job isn’t just how you conceive of it. You can see it’s utilities and functions as others, in many different positions, depend on the quality of work you deliver.  This systems view enables you to have a larger understanding of your job, how it’s changing and how the day to day demands relate to what your company or governmental institution does. With this understanding, you’re now ready to assemble your strategy—which means situating your “good intel” into a larger vision that belongs to you.

This larger vision or strategy always needs to have two parts. First, you must clarify the essential deliverables you see as critical to the successful implementation of your project or initiative. This is the easy part. Second, you need to find the essential features that are missing and/or distorted. This is the hard part.

But every project has limitations, inadequacies and flaws in its formulations. When you are assembling your strategy, your job is to reveal these limitations. This is where you are going to disappoint the powerful people around you.

The limitations you uncover need to be translated into actionable steps you and/or your team can execute on. In doing this, you will be including much of the design you’ve been handed, but you’ll also be laying foundations for ways you can go beyond these guidelines and deliver a superior result.

#3. Proactively Communicate
Before acting, communicate. Don’t leap too quickly into action if you aren’t communicating first. Too many novice leaders leap into execution once they have their new vision and direction because they are excited to provide the newfound value they see.

But communicating your vision first is actually the key move to make, because it’s what sets you apart from the employees who are busy executing already. They’re “connecting the dots” as they’ve been told. Meanwhile, you’ve developed a new vision and a more complex strategy to deliver greater value. And the primary differentiating move for you will happen in the quality of the conversation that you initiate with those you report to.

In that critical conversation, you’re going to demonstrate your larger aptitude to lead, assess, strategize and deploy your resources in more efficient ways. When reviews come around, these more nuanced conversations you’ve initiated (which are sure to yield greater organizational value) will be some of the differentiating criteria for how you will be assessed.

Communicating first is what enables you to leverage greater agility and genuine collaboration with the people you report to.

#4. Heighten the Disappointment & Hold Your Ground
The human mind is motivated by pain. While we all like to think we’re more motivated to deliver great value, to improve our organizations, and to bring better services to our world, the truth is that at the end of the day we usually don’t leap fully into tremendous opportunities. We do, however, get into action when we’re suffering. When we’re in pain, we take action. Use this core conditioning to work for you.

The people you report to need to feel the texture of the suffering that will result from the limitations you’ve identified in the new project. One formula that often works goes something like this, “I don’t like to disappoint you, but given my expertise and how I see this initiative, I’m not able to execute as we discussed earlier. This is because these limitations are going to lead to…”

Hold your ground on what you will and won’t execute on. It’s not uncommon for management or leadership to merely reinforce the existing scope, frames and deliverables. IF you’ve done good intel, you’ll already have thought through these objections to your strategy. Remember, you’re the expert as it pertains to your job. Don’t give this up easily. Doing so tells people you’re not ready for larger organizational responsibilities.

Reinforce, reassert and bring to life the felt textures of the suffering you can see on the horizon. Underscore the limitations. Stay committed to not placating those in power. Be resolute in your adherence to delivering more value to the organization as you see it. Include your perspective from inside of your job’s vantage point, your boss’s or board’s positions, and “the outside-in” vantage point on the organization.

Genuinely collaborate in new ways and establish new parameters. Once you do, you’re ready to take action. Now it’s time for execution.

#5. Execute
Rigorous planning, revisioning and refashioning of projects and initiatives enables you to do more than merely execute on the tasks you’ve been handed—it empowers you to re-author your job and how you’re going to function. The kind of value you can offer your organization increases. You’re more suited to take greater responsibility for your work. Through your commitment to yourself and your organization you’re better prepared to deploy your own and/or your teams’ talent in more creative and effective ways.

One final but absolutely critical point: The art of disappointment is not to be employed on superficial or trivial features of a project or initiative. Deploy it only when you can find significant qualitative gaps in the projects and/or initiatives you’ve been assigned. If you can’t find and/or formulate the serious flaws, build your skills around getting good intel and being able to see the organization from a systemic “outside-in” vantage point. These capacities alone will gain you tremendous credibility and influence.

But keep your eyes peeled for limitations no matter what. The areas where we fail are everywhere. It’s a matter of finding them before your organization prematurely deploys its resources.

This is how (paradoxically) preemptively disappointing your boss, when executed skillfully, can save you and your organization from much more painful disappointment later on down the road—while at the same time rapidly accelerating your professional development.

Rob McNamara
Creator of Commanding Influence: Your Development for Greater Mastery at Work
Harvard University Teaching Fellow
Leadership Coach & Author of The Elegant Self
Faculty & Coach, Integral Facilitator Certificate Program

Rob McNamara’s premiere developmental audio learning program, Commanding Influence: Your Development for Greater Mastery at Work, was released on October 27th. Learn More.


Rev. Alia Aurami

Love this, even though I’m not in the employment situation you mentioned! And thanks for the suggestions about all the prep work before acting. As an Enneagram One, I can always see the limitations and “errors,” and can always see the suffering that I profoundly want to prevent, but I don’t always gather enough info and have ‘enrolling conversation’ with the people I collaborate or consult with; too often (still) I just barrel ahead with fixing what I see as causing future suffering, from my own viewpoint, and I think everyone including me would be happier if I take my time and do all these steps! Thanks, Rob !

Rob McNamara

You are most welcome! Thank you kindly for reading and I’m thrilled to hear this can be of service to you as you bring more nuance to how you relieve the various forms of suffering your heart is attuning to.
All my best to you & let us know how it goes if you get inspired!

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