When Leadership Is the Roadblock: Underprepared, Stuck, or Contrarian

We’ve all been there. You’re working hard to move a project forward, rally a team around a vision, or launch something innovative – but instead of support from leadership, you’re faced with a roadblock. The kicker? Sometimes the biggest obstacles aren’t budget constraints, technology gaps, or talent shortages. They’re the very people meant to guide the ship (Goleman, 2000).

Today, let’s talk about three common leadership roadblock personas: the Underprepared, the Stuck-in-a-Mindset, and the Contrarian, why these happen, and what you can do to navigate around (or through) them.

1. The Underprepared Leader

**What it looks like:**They show up to meetings without reviewing materials. They haven’t read the pre-read. They ask questions already answered in slide three. They say “I’ll need to think about this” repeatedly without clear next steps (McKinsey, 2021).

**Why it happens:**Often, they’re overloaded with competing priorities and decision fatigue (Baumeister & Tierney, 2011). Sometimes, they simply aren’t bought into the effort enough to prepare. Either way, it delays decisions and drains momentum from teams waiting on input.

How to help them:

Summarize ruthlessly. Start communications with “Here’s what you need to know” bullet points before any deep detail. This approach aligns with executive communication best practices (Duarte, 2012).

Pre-frame decisions. When you send materials, clearly state: “At tomorrow’s meeting, I’ll ask for your approval on X and your guidance on Y.”

Use visual cues. Replace 20-page decks with a single slide outlining options, tradeoffs, and recommendations. Tools like Miro, Figma, or simple PowerPoint SmartArt can rapidly visualize complexity (Brown, 2008).

Default decisions. Where possible, propose a recommended path forward as default, requiring them only to say yes or no rather than brainstorm (Kahneman, 2011).

2. The Stuck-in-a-Mindset Leader

**What it looks like:**They keep referring to “how we’ve always done it.” New ideas get shot down with “That’s not how our business works,” even when market realities have shifted (Kotter, 1996).

**Why it happens:**Change challenges their expertise and credibility. Admitting something new might work can feel like admitting what they did before is no longer enough (Argyris, 1991).

How to help them:

Anchor to goals, not solutions. Start discussions by re-aligning on business outcomes. For example, “We’re aiming to increase adoption by 30% this quarter. Here are three ways to achieve that, including your current approach” (Drucker, 1954).

Use data and stories together. Data shows evidence, but stories show empathy. Combining performance metrics with real customer feedback makes the case for change stronger (Denning, 2005).

Pilot first. Reduce perceived risk by proposing a low-cost pilot to test new ideas before broader adoption. Tools like Trello, Monday.com, or Asana can manage these pilots with clear visibility and short feedback loops (Atlassian, 2023).

Celebrate their past wins. Acknowledge what they built before. Then pivot: “Your approach built an amazing foundation. This next step builds on that success to meet today’s customer expectations.”

3. The Contrarian Leader

**What it looks like:**They disagree with everything. If the team proposes A, they want B. If you propose B, they want A. Their feedback loops are filled with “devil’s advocate” takes, and meetings with them feel like Shark Tank episodes with no deals (Grant, 2016).

**Why it happens:**Sometimes it’s their nature to challenge assumptions, which can be healthy in moderation (Edmondson, 1999). Other times, it’s driven by ego, insecurity, or a desire to reassert control if they feel out of the loop (Goleman, 2000).

**What they might forget:**Leadership isn’t about poking holes in everything just to prove a point. If a proposal aligns with business goals or improves outcomes, the role of leadership is to guide, support, and clear obstacles – not create them. Effective leaders ask critical questions to refine and strengthen ideas, not to stall progress or assert authority unnecessarily (Kotter, 1996).

How to help them:

Pre-socialize ideas. Meet with them 1:1 before group sessions to preview recommendations and address concerns privately (Kotter & Cohen, 2002).

Frame decisions around tradeoffs. Instead of asking “Do you agree?” ask “Which option best aligns with our goals, given these tradeoffs?”

Limit choices to two. Too many options fuel contrarian spirals. Present two paths with pros/cons rather than five ideas to critique (Schwartz, 2004).

Use collaboration tools. Platforms like Confluence, Notion, or shared Google Docs allow them to leave comments asynchronously, reducing in-meeting friction (Atlassian, 2023).

Ask for their take first. If you know they will oppose suggestions, flip the script. Ask their views before presenting yours to reduce default resistance.

Quick Tools & Approaches

Here are some fast tools and frameworks to help navigate leadership roadblocks:

RAID Logs (Risks, Assumptions, Issues, Dependencies) to transparently surface decision delays as risks (PMI, 2017).

Decision Trees to visually map options and outcomes, clarifying choices (Kahneman, 2011).

Meeting Pre-Reads with Summary Pages for quick executive consumption (Duarte, 2012).

Pilot Charters as one-page test plans with success measures and timeframes (Kotter, 1996).

Empathy Maps to understand motivations and fears before proposing changes (Brown, 2008).

Final Thoughts

Leadership roadblocks are frustrating, especially when teams feel the slowdown in momentum and morale. But remember:

The underprepared can be nudged with clarity.The stuck can be guided with empathy and evidence.The contrarian can be disarmed with structure and engagement.

At the end of the day, they’re human – just like the rest of us – with competing pressures, insecurities, and ambitions. The faster you can understand why they’re a roadblock, the quicker you can find your way around it… or even transform them into an accelerator for your goals.

References

Argyris, C. (1991). Teaching Smart People How to Learn. Harvard Business Review.

Atlassian. (2023). Team Collaboration Tools. Retrieved from atlassian.com

Baumeister, R., & Tierney, J. (2011). Willpower: Rediscovering the Greatest Human Strength. Penguin.

Brown, T. (2008). Design Thinking. Harvard Business Review.

Denning, S. (2005). The Leader’s Guide to Storytelling. Jossey-Bass.

Drucker, P. (1954). The Practice of Management. Harper & Row.

Duarte, N. (2012). HBR Guide to Persuasive Presentations. Harvard Business Review Press.

Edmondson, A. (1999). Psychological Safety and Learning Behavior in Work Teams. Administrative Science Quarterly.

Goleman, D. (2000). Leadership That Gets Results. Harvard Business Review.

Grant, A. (2016). Originals: How Non-Conformists Move the World. Viking.

Kahneman, D. (2011). Thinking, Fast and Slow. Farrar, Straus and Giroux.

Kotter, J. (1996). Leading Change. Harvard Business Review Press.

Kotter, J., & Cohen, D. (2002). The Heart of Change. Harvard Business Review Press.

McKinsey & Company. (2021). Decision-making in Uncertain Times.

PMI. (2017). A Guide to the Project Management Body of Knowledge (PMBOK® Guide). Project Management Institute.

Schwartz, B. (2004). The Paradox of Choice: Why More Is Less. HarperCollins.