The Three Obstacles Every Leader Should Expect: How To Stay Ahead Of The Things That Derail You

What if the surest way to hit your goals is to imagine all the reasons you won’t?

Last week, I left for Nashville earlier than planned. I was supposed to leave on Sunday, but by Friday morning the Midwest forecast had taken a hard turn. A blizzard was moving in, and something in me knew, If I wait, I might not get out at all. I had to be in Nashville to lead our Scaling Leader workshop. Missing it was not an option.

So, I packed early and said an earlier goodbye to my family. It wasn’t convenient, but it was the right move.

By Saturday, the storm was in full swing. Flights were canceled and delayed for days. Watching the updates from my hotel room, I felt relieved.

It reminded me of something I see often, both in my life and in the leaders I work with. Things go better when we expect obstacles instead of pretending they won’t show up.

Why Anticipating Obstacles Matters

If you want to increase the likelihood of achieving your goals, make it a habit to imagine what might get in the way. When you can name the obstacle ahead of time, you can prepare for it instead of reacting to it.

This is why I often ask leaders, “Imagine we are at the end of the quarter/year and you did not achieve what you planned. What went wrong?”

Over the past few weeks, I have asked this question in workshops, coaching calls, and private consulting sessions. The answers came quickly: projects taking longer than expected, calendars filling with urgent issues, decisions being made too late, unclear expectations, work drifting because check-ins did not happen, and the usual surprises that show up when you are already stretched thin. One leader put it simply: “I try to fit eight months of work into thirty days.”

Different roles, different situations, but the themes were the same. Capacity. Communication. Accountability. These are the things that get in the way, even when the goals and project plans are clear.

OBSTACLE #1: IGNORING CAPACITY CONSTRAINTS

Most leaders plan as if future-you will have more time, energy, or focus than current-you. But your calendar rarely opens up the way you imagine it will. In many cases, the load even increases.

This is why capacity constraints are the obstacle most leaders underestimate. When goals fall short, it’s often because the plan did not account for reality. Ignoring capacity usually comes from hope. But hope is a virtue, not a strategy.

What to do instead: Before you take on something new, pause long enough to see the full picture. Look at your calendar, your team’s capacity, and what is already committed. Once you see what is true about your load, you may need to renegotiate commitments, adjust timelines, or revise your plan so you have more margin.

OBSTACLE #2: ASSUMING COMMUNICATION WILL HAPPEN NATURALLY

A lot of execution problems are really communication problems. Someone thought a deadline was flexible. Someone did not realize someone else was waiting on them. The team was not on the same page about what mattered most.

Communication is not automatic, even on healthy teams. Without a clear way to stay aligned, plans drift. This obstacle often looks like:

• The team isn’t aligned on the real priority.
• People assume others understand the context or urgency.
• Expectations stay in the leader’s head.
• Updates only happen when something goes wrong.

What to do instead: You need a clear way to keep everyone aligned. That starts with communicating objectives and timelines so people understand what is expected and then choosing a simple rhythm for updates.

OBSTACLE #3: NOT HAVING THE RIGHT KIND OF ACCOUNTABILITY

Gretchen Rubin’s book The Four Tendencies describes how people respond to expectations: Upholders, Questioners, Obligers, and Rebels. Some follow through easily when they set an internal expectation. Others stay on track only when someone checks in. And some need to understand the why before they move forward. Your tendency shapes the accountability you need, and it shapes what your team needs.

This shows up in different ways:

• Upholders usually don’t need much external accountability. They follow through when expectations are clear.
• Obligers follow through when someone is expecting an update, but drift when no one checks in.
• Questioners stall when the project lacks clarity or reasoning, because they need to understand the why.
• Rebels make progress when they have autonomy, but stall when the structure feels too rigid.

People follow through when accountability matches how they work.

What to do instead: Build accountability into the plan early and shape it around how you and your team naturally follow through. This could be a weekly check-in, a quick daily update, or pairing the right people for follow-up.

Before You Step Into the New Year

These three obstacles show up in different ways, but the solution is the same: name them before they slow you down. When we miss our goals, it’s often because of things we could have predicted and prevented. Make it a habit to imagine what might go wrong. Then, prepare for it instead of reacting to it. Ask yourself these two questions:

• If your plan doesn’t happen, what will be the cause?
• What could you add or change to overcome that challenge?

Set aside a few minutes this week to answer those two questions. It’s a simple way to start the new year with more clarity and less pressure.