How to Unblock the 6 Most Common Obstacles to Success

Including 7 helpful worksheets.

Oct 25, 2024

On the wall in my office, I have a poster that reads:

“I tried to be innovative once, but I got stuck in meetings.”

It captures the frustration many leaders feel: the ambitions are clear, but making it happen often feels like swimming through peanut butter.

To bring your goals to life, you need people to take ownership. You need less talking, more action, less analysis, faster decisions, less bureaucracy, and more initiative. My new book, Unblock, is a practical guide for leaders ready to break through organizational barriers and finally move the needle. Here is a sneak preview.

NOTE: At the end of this newsletter, I have included a link to the book’s bonus materials.

1. Strategy

If there is a gap between your strategy and day-to-day action in the organization, look at the strategy itself. Chances are, it is either a document with carefully crafted lofty visionary statements or a detailed list of everything that needs to be done. In both cases, it won’t create the necessary strategic awareness for teams to execute it.

Try this: Use even-over statements to articulate strategic choices. For example, the clothing brand Patagonia is famous for having the trade-off “Sustainability even over Profit.” Everyone in the organization is aware of this strategy, and articulating a simple heuristic like this permits people to favor the sustainable approach over a profitable one when facing an everyday decision. Furthermore, even-over statements force you to articulate what you are willing to trade off. What is it that you will NOT prioritize to achieve your ambitions?

2. Steering

Have you ever felt that your meticulously crafted annual plans quickly become obsolete? Many organizations invest heavily in up-front planning, only to realize later that adapting to change demands a more flexible approach.

Try this: Facebook is known for planning long-term and very short-term, but nothing in between. To put this into practice, use 90-day Outcomes. Based on the longer-term strategy, define what outcomes your team or department will focus on in the next 90 days. Write them as outcomes, not outputs. So don’t write “Launch new mobile app” but “Over 100 people use the app daily and have left a positive review.”

3. Decisions

You’ve probably been in situations where decisions drag on for weeks from meeting to meeting, as leaders try to get everyone to agree or to request more information before any action is taken. The accumulating cost of indecision is often invisible.

Try this: Help teams differentiate between reversible and irreversible decisions. When a decision is similar to picking which hat to buy, you don’t need to overthink it. You can act quickly, learn from the outcome, and move forward. To create momentum, stop asking, “Do we all agree?” but ask, “Is it safe to try?”

4. Ownership

When people are not taking ownership, don’t blame them for it. Instead, look at the organizational system to see how it encourages or discourages them from taking initiative. One common problem is that it is unclear within which boundaries people are free to act. Without that clarity, people will continue to ask for permission or wait for instructions.

Try this: Define the “waterline” — a concept invented by W.L. Gore (the makers of gore-tex). Imagine your teams are on a ship. If you make an unfavorable decision, and it results in something puncturing the ship above the waterline, it’s annoying. However, you can get to shore and repair it. But if something below the waterline blows up, the ship might sink, resulting in irreversible harm. Consider what types of decisions people are hesitant to make that you’d like more of without them needing to ask for permission.

5. Teamwork

Have you noticed that conversations lack openness or that feedback is scarce? Psychological safety—feeling secure to share ideas and take risks—is essential to effective collaboration and high performance, yet many (leadership) teams struggle to foster it.

Try this: Build trust and empathy in the team by asking members to draft their “personal user manual.” It is a document outlining ‘how to work with me,’ including answers to questions like “What are some things people may misunderstand about you?”, “What do you struggle with, and how can your colleagues help you?” and “How do you prefer to receive feedback?”

6. Meetings

We have too many meetings, many of which are of poor quality. Research confirms dysfunctional meetings are associated with reduced market share, innovation, and employee engagement. Every minute someone spends in a wasteful meeting can’t be spent on meaningful work. At the same time, meetings are crucial for coordination, collaboration, and sense-making. You need a meeting culture that makes it easier, not harder, for teams to reach their goals.

Try this: Stop all recurring meetings and establish an “operating rhythm”—a structured, predictable cadence of fit-for-purpose meetings designed to move work forward. Start by asking: which conversations must we have and how often?

For example:

A weekly meeting with a flexible agenda, focused on getting everyone what they need to progress in the upcoming week
A monthly retrospective meeting, to reflect on how things are going and what can be improved
A quarterly strategy meeting to review the long-term strategy, and review and update 90-day outcomes.

Unblock is filled with real-world examples, step-by-step exercises, and checklists to help you put concepts into action right away. My goal is to help leaders achieve their ambitions and develop an organization that is both successful and amazing for the people who work in it.

PS. Did you know you can claim a free extra copy of one of my books?

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