Unrealistic Expectations – The Most Dangerous Piece of Software

   Agile Software Development

When delivering greaht software, product and project managers connect many elements. Sometimes the process is like finishing a puzzle; other times it is like fixing broken glass. The pieces may still fit together, but handling them can be dangerous. This is particularly true when handling expectations for software.

Years ago, I joined a fast-growing SaaS (Software as a Service) organization known for its talented teams and charismatic leadership. I jumped into a complex regulatory software project delivered through new Agile processes. It was great to work with smart, capable people who also loved challenges.

As an added bonus, our leaders fostered a culture of empowerment. They encouraged staff to Get Stuff Done or “GSD” on their own, so teammates were always looking to grab the ball and run. I was surrounded by other hard-working employees who loved digging into complex problems to deliver value quickly.

Sounds like heaven, right?

Whooshing in Wonderland

For a time, the work felt heavenly. Tricky projects were running fast, and spirits were flying high. At first, I was skeptical of our acceleration. Experience taught me that complex requirements need time to be understood and communicated. But my new teams were exceptionally bright and talented, and management rewarded action. Contributors quickly understood key points, then dove into solutions. And the positive camaraderie felt aligned with the Modern Agile principle of making safety a prerequisite.

During my “honeymoon,” it was exciting to see our velocity increase. Teams picked up work without the overhead of deep explanations. It felt like a magical wonderland where smart people understood each other intuitively. The company had a great track record leaning into a loose, speedy culture, so who was I to hold it back? And the energized, can-do attitude around me was captivating. I began to believe in the fast handoff approach. After a couple of months, a manager peer counseled me to stop “waiting for the other shoe to drop” and join the fun. I hadn’t experienced this kind of whoosh since my tech start-up days, and it was thrilling for a time.

Managing Expectations Can Be Dangerous.
Not Managing Them Is Worse.

The first signs of trouble came when stakeholders came calling for updates on their favorite bits of scope. Before I arrived, the company had paused the product roadmap to pursue a major new opportunity. Delivering the hot new project had taken priority over managing past commitments and expectations. So people had been left to their own conclusions.

Assumptions were not validated because within our fast-moving culture, pausing for detailed confirmations was seen as non-Agile overhead. It was risky to clarify stakeholder expectations if you were seen as not promoting “GSD.” Slowing down could be dangerous, even to direct traffic. So unspoken assumptions weren’t shared nor managed. As a result, it was easy to get off track.

Without confirmation, teams could believe they were making progress, even if it was more like Brownian Motion. People felt good sprinting off in any direction, whether toward the finish line or not. While raw speed had value during “fail forward fast” experimentation, it became a liability when managers wanted defensible gains. Moving too fast could lead to rework or wrong work. So why were these behaviors pervasive?

If you don’t know where you are going, any road will get you there.
– Lewis Carroll

In retrospect, some of our people valued rapid comprehension and fast starts more than deeper understanding and active confirmation. Perhaps they believed quickness of thought was a sign of higher intelligence. As a parent, I’d seen this at home with my high school student. He would learn a complex new topic quickly, and then stop paying attention. When this happened, he would fall behind. I began to see similar patterns at work, where measured progress would have been more productive than quick starts without validations.

Unrealistic Expectations, The Most Dangerous Piece of Software

Compounding the risk, not all managers actively validated progress. In some cases, once managers heard what they thought they wanted, it was easy for them to disengage. After all, they had to get back to running fast for their own bosses. I began to notice that more than one stakeholder would have failed the “mirror test.” If asked whether their teams were working on the right stuff, they might have answered yes. But how did they truly know?

Since software is so flexible and powerful, it was easy for the pool of expectations to grow. Stakeholders assumed their expectations were covered and stopped digging once they heard what sounded like a yes. With each unconfirmed interaction, total expectations grew. As a result, software projects risked collapsing from inferred weight. Worst of all, real scope became a shrinking proportion of assumed scope, reducing perceived return on investment.

Unrealistic Expectations, The Most Dangerous Piece of Software; Venn Diagrams

 

When Speed Kills

By avoiding the discomfort of managing expectations, we created more suffering. By driving without deliberate pace and direction, we guaranteed:

  • Wrong work completed
  • Expectations missed
  • Customers unhappy
  • Investments wasted

Finally, after a project miss became evident, instead of changing behaviors, managers encouraged personal heroics to patch gaps and please stakeholders. From a distance, this looked like “GSD” hustle, and was praised. But clearly, R&D teams and investments weren’t reaching their potential. So team leads and lower-level managers were routinely reassigned or released from the organization, cut by the dangers of mishandled expectations.

What to do?

From my own lessons learned, I coach better practices for my clients, my teams, and myself. These include intentional communication and active expectation management. I found a handful of habits to be helpful.

  • Manage expectations – simple in concept, but not always easy or safe.
  • Be clear when giving or accepting Musts, Wants, and Nice-to-Haves for any project.
  • Confirm objectives, timelines, and outcome measures with all relevant parties.
  • Use active listening and tools to build common understanding. Wireframes, prototypes, story skits, personas, and good design process all can foster dialogue.
  • Communicate plans, estimates, or dates with context. Helpful context may include risks, dependencies, assumptions, and confidence levels on estimates or date projections.
  • Actively ask stakeholders and contributors for validation of assumptions, goals, and progress throughout the project
  • Prepare for uncomfortable conversations along the way

Experienced product and project managers will recognize these concepts as part of the “blocking and tackling” of the profession. Even for pros, however, it can feel uncomfortable or unsafe to circle back to busy managers or misinformed colleagues who already think they are aligned. And when necessary conversations are avoided, danger grows.

Communicate Safely

When any form of safety feels like it could be at risk, it is important to plan how best to communicate and then act on that plan. If a challenging conversation becomes necessary to manage mismatched expectations, don’t wait. Prepare for the talk, identify common goals, list factual observations and your perspective on their impacts, anticipate the likely questions, and call the meeting. Often it will be a one-on-one conversation, in person if possible.

During the meeting, lead with the common goals you both share. Then volunteer your factual observations, explain how you feel they are relevant to expectations, and ask for reflection. This will help you gauge next steps in the dialogue. If you hear or sense that safety, trust, or transparency are at risk, deal with those first.

Ask for feedback on your observations and interpretation of what they could mean. If needed, provide examples of unwanted outcomes that you are working to mitigate. Clearly state what you are aiming for and what you are aiming to avoid. Once you are on the same page, ask for their input and support for next steps. Then follow through on your commitments from the meeting. Tools like Crucial Conversations or Fierce Conversations can help you plan and negotiate challenging dialogue.

When you model respectful, prepared conversations, several positive things happen. You efficiently communicate key facts and opinions. And you encourage reciprocal trust and transparency. Over time, if you keep walking the talk, others are more likely to be open and proactive with you in return. As that happens, you gain insight into other facts and opinions that could affect your project. And as you build your ability to handle challenging dialogue, you become a resource for others who want to develop this crucial skill.

Validate Assumptions

Of course, it is important to communicate effectively throughout a project, not just during the challenging moments. For example, sometimes stakeholders or contributors may not think to volunteer information or opinion unless asked. So you can help manage expectations by regularly asking open-ended questions with positive intent, such as:

  • “What do you think?”
  • “What are we missing?”
  • “What are your concerns?”

Well-intentioned questions like these can start in the earliest requirements gathering meetings. As the project scope takes shape, keep testing assumptions and context. When a stakeholder identifies a requirement, ask them to put it into context. That might mean prioritization among other asks from that person or their team. Or it could be their opinion of the requirement’s value compared to current scope. Or simply identifying if this is a must, want, or nice-to-have from their perspective. Too often we accept a request into backlog without understanding the context or priority of the ask – risking mismanaged expectations. Even if the chief executive gives a new priority requirement as a must-do, it is fair to respectfully ask for context. This isn’t necessarily to challenge the directive, but rather to understand what they really want, by when, and under what conditions relative to other planned investments.

In cases where you see a dependency on other teams or projects, ask questions to uncover any unspoken risks or assumptions. And when receiving estimates or date projections from delivery teams always ask for rough confidence levels; they always come along with speculative opinions, but are often not voiced or captured. Experienced pros know there is a big difference between similar-sized estimates or date projections when they are given with high versus low confidence.

Finally, when you lead planning meetings or ask open-ended questions, it is okay to lean into uncomfortable silences. This signals the truth of your interest in others’ perspectives, and it gives people time and impetus to speak. Sometimes asking the same or similar questions at different points in a meeting can also underline your intention and encourage higher-quality dialogue. So don’t always settle for the first response, even if it is what you hope to hear.

Walk the Talk

Model the behaviors you want to see in others, including when managing expectations. When you lead honest, difficult conversations with thoughtful questions, people see your willingness to step out of personal comfort and safety for the common good. If you need inspiration to bolster your courage, Leadership on the Line contains excellent examples to consider. It also provides case studies that may help your peers or leadership teams. Taking on personal risk and managing it for your team is a strong form of servant leadership. If this is new territory for you, I recommend True North and its exercises to prepare you for authentic and inspirational action.

Finally, if you have to manage the expectations of your executive leadership team, and their attention is hard to win, get creative and be worthy of their time. As an example, one successful colleague understood that her executives were natural storytellers and video consumers. So she used interviews and customer journey storyboards to build a video in her executives’ language that spoke directly to outcomes they valued. Other times, you might only need to prep for a quick 1-1 with the boss. Find a practical approach that works for your audience and use it.

Managing expectations is a bit like living life well. It can be scary. But you’ll generally have fewer regrets for what you did than for what you didn’t do. So go for it. Manage expectations, avoid (some of) the dangers, and let me know how it goes for you.


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