Love Your Curmudgeon

Grumpy cat

Attribution: Article based on presentation co-developed by DITA Strategies and Intuitive Stack and presented at ConVEx 2024 by Dan Schommer and Lief Erickson.

In any organization, there are always individuals who act as the voice of caution and reason. These are the curmudgeons – the naysayers who ask tough questions and challenge assumptions. I’m sure you can think of one team member who fits this bill—you may have even filled the role yourself once or twice.

While the curmudgeon’s skepticism may sometimes seem like an obstacle, curmudgeons can be valuable assets when it comes to initiating new projects or changes at work. By understanding their motivations and engaging them effectively, we can harness their expertise and insights to make our initiatives stronger and more successful.

The Curmudgeon

Curmudgeons are often long-tenured employees with deep institutional knowledge and experience. They know how things work, what has functioned well in the past, and what has not. They are invested in the current processes and may be wary of change, especially if they have been burned by previous initiative failures. This can make them seem negative or resistant, but their skepticism often stems from a desire to protect the team and ensure that any changes are well-considered and worthwhile.

The Role of The Curmudgeon

Despite their initial resistance (and often due to their resistance) curmudgeons can be valuable assets when introducing new projects or initiatives. Their institutional knowledge and attention to detail can help identify potential pitfalls or roadblocks that may not be immediately apparent to others. By involving them in the process and listening to their concerns, you can gain insights that can help refine and strengthen your plans.

How To Spot a Curmudgeon

A curmudgeon is often a senior team member without an official leadership title, but with significant institutional knowledge and experience. They typically know all the ins and outs of how things currently work and why processes evolved the way they did. A few telltale signs can help you identify a curmudgeon on your team.

Public binoculars overlooking a cityscape

Tenure and Seniority. While not necessarily old in age, curmudgeons tend to have some seniority, often being the longest tenured team members. Their deep understanding comes from a history with their colleagues as well as experience navigating the existing systems, processes, and politics. Newer employees are less likely to have built up this institutional wisdom.

Stubborn But Insightful. Curmudgeons are often seen as stubborn or set in their ways. They rarely shy away from asking difficult questions that get to the heart of an issue. In fact, they frequently voice concerns that others may be thinking but are too afraid to say aloud.

Skeptical of Change. With their deep understanding of (and comfort in) how things currently operate, curmudgeons are often wary of changes that could disrupt the existing systems that they have helped develop. You may notice them framing potential changes negatively or being reluctant to get on board with new initiatives – you need to convince them of the real need and benefit of change.

Proud and Protective. Curmudgeons take pride in the value they provide to the team (as they should). In many cases, they’ve spent years cultivating a mastery of current processes and technologies. This can make them defensive when changes threaten to minimize their expertise or impact. They may also push back if they feel a new direction could put the team's effectiveness at risk.

Curmudgeon’s Motivation

While a curmudgeon's resistance to change can be frustrating, it's important to recognize that their motivations often come from a positive place. They are invested in maintaining what currently works well and they are concerned about new initiatives because change incurs risk.

The root of a curmudgeon's motivation is a desire to safeguard the team's effectiveness. While their objections can seem merely obstructive, they arise from a genuinely protective stance. Understanding and respecting these motivations is key to bringing curmudgeons on board as allies rather than adversaries.

Historical European steel armor

The Agent of Change

Seemingly in opposition to the curmudgeon is the agent of change – the person driving a new project, initiative, or way of working. The agent of change is looking for opportunity and is usually someone from upper management, a different department, or an external company. As such, they are often unfamiliar with the team and their processes.

When compared with the curmudgeon, the agent of change has a vastly different perspective and set of motivations. Agents of change tend to have an optimistic, glass-half-full mindset. In the proposed changes, they see opportunities for improvement and growth rather than risks to the current way of operating. Their outlook is focused on potential future benefits.

While curmudgeons aim to protect what currently works well, agents of change are always looking for ways to do things better. They are eager to explore new tools, processes or approaches that could make the team more efficient, effective, or innovative. Agents of change usually have an actual mandate or strong belief that the proposed changes are necessary. This could stem from new organizational directives, competitive pressures, or their own firsthand experiences.

Agents of change typically have more upfront context and knowledge about the proposed changes compared to others on the team. They may have been involved in the early planning or have additional insights into the required future state. This information asymmetry can create a disconnect with curmudgeons and other team members.

The agent of change role is vital for driving teams forward and adopting new best practices. However, their zeal for change can steamroll over the curmudgeon's valid concerns if they don't take the time to understand and address those motivations. Finding a productive balance between an agent's vision and a curmudgeon's wisdom is key.

The Relationship Between the Curmudgeon and The Agent of Change

Projects need both the curmudgeon and agent of change – the combination can create friction but also provide necessary balance when driving change initiatives. Because of their contrasting motivations and perspectives, they are natural adversaries – but this tension can be highly productive when navigated properly.

This opposition in motivation creates an inherent clash. The agent sees their mission as progressing the team forward, while the curmudgeon views it as an unnecessary disruption that diminishes their effectiveness. The curmudgeon is patently distrustful of the agent's vision for change.

If the agent of change attempts to unilaterally drive their change agenda while ignoring the curmudgeon's objections, it will likely lead to a counterproductive power struggle and a failed initiative. The curmudgeon holds crucial institutional knowledge and wields influential soft power that can derail initiatives if not handled delicately.

However, if the agent takes the time to engage with the curmudgeon to understand their motivations, it can strengthen the change initiative tremendously. The curmudgeon's skepticism and direct critiques can reinforce a plan by addressing blind spots, and their hard-earned wisdom ensures potential pitfalls are foreseen and mitigated.

With the proper communication, the curmudgeon presses the agent to solidify a realistic vision, while the agent gives the curmudgeon faith that there is a viable path forward that capitalizes on their experience rather than makes it obsolete. By synthesizing these two opposing roles, you can implement change initiatives more smoothly, efficiently, and sustainably.

Use Case: Creation of New Success Metrics/KPI’s

For example, imagine a scenario where upper management has decided to implement new success metrics/KPIs for technical content.

Close up of measuring tape

In this instance, the agent of change is the representative sent by management. In an ad hoc meeting, they announce to the information development team that they plan to introduce success metrics and a feedback loop. Specifically, the metrics will be bound to organizational goals, the team will gather and address feedback, and management will create a process of continuous improvement.

The curmudgeon’s immediate response is to point out that, because management, rather than the team, will decide on the metrics, the measurements will not capture reality at best and be irrelevant at worst. Furthermore, as is the pattern with these types of initiatives, the metrics and goals won’t last long term. And anyway, doesn’t the current feedback process work well enough?

What the curmudgeon doesn’t voice is that they’re worried that the new metrics might devalue their and their team members’ performances and that the measurement process disenfranchises their whole team.

Because the agent of change doesn’t adequately prepare for the meeting, it goes poorly, and the initiative is off to a bad start. In hindsight, what did they do wrong? In their initial announcement, the agent of change:

  • Failed to address the emotional impact of the change

  • Didn’t anticipate the team’s wariness to being measured

  • Didn’t consider the team’s history with similar initiatives

  • Undervalued the current feedback system

  • Disenfranchised team members in the development phase

Fortunately, the agent of change still has remediation options. They can recalibrate and try to align their goals with those of the curmudgeon and the rest of the team. To do this, the agent of change needs to acknowledge the team’s resistance and collaborate one-on-one with the curmudgeon to address their concerns. This can include building success metrics together, gaining direct input on measurements from the curmudgeon, and assigning the curmudgeon responsibility over one or more of the KPIs.

Strategies For Successful Engagement

While our agent of change was able to re-orient their initiative to involve the curmudgeon, it would have been better to mitigate rather than remediate. Engaging curmudgeons effectively requires a combination of understanding, respect, and collaboration. Here are some strategies you can adopt before you make any missteps that isolate or disenfranchise your curmudgeon.

Appreciate Their Role. Recognize that curmudgeons often play an important role in their team or organization, even if their methods seem unconventional. They are invested in the success of the team and want to ensure that changes are well thought out.

Listen to Their Concerns. Instead of dismissing their objections, take time to understand their perspective. They may raise valid points or identify potential issues that you had not considered.

Involve Them in The Process. Curmudgeons are more likely to be receptive to change if they are involved in the planning and implementation process. Seek their input and ask them to participate in developing solutions.

Assign Them Responsibilities. By giving curmudgeons specific responsibilities or tasks related to the new project or initiative, you can leverage their expertise and increase their buy-in.

Build Trust. Be transparent about your intentions and follow through on your commitments. Curmudgeons are often skeptical of change due to past experiences, so it's important to establish trust and credibility.

While curmudgeons may initially seem like obstacles or disruptors, their skepticism and attention to detail can be invaluable assets when introducing new projects or initiatives at work. By understanding their motivations and engaging them effectively, organizations can harness their institutional knowledge and expertise to identify potential issues, develop better solutions, and increase the chances of success. Rather than dismissing or ignoring curmudgeons, it's important to embrace their role and leverage their unique perspectives to drive positive change.


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