Leaders Should Be Obsessed With Problems
Without problems, leaders wouldn’t exist. Yet, so many I encounter carry anxiety and stress about the very challenges they’re meant to tackle.
Recently, I spoke with a fellow sales director who vented about the issues he’s dealing with.
What struck me wasn’t the issues themselves—it was how he described them.
It was almost as if he believed in a “promised land” where problems no longer existed. He fidgeted in his seat, anxiously hoping I’d jump in to save the day.
But I didn’t.
Because the real issue wasn’t the problems he faced—it was his relationship with them.
So, I made him a deal:
He had to fundamentally accept that problems are a sign of life, before I comment on any specific issue.
From then on, I told him to start observing his approach.
• What’s his body language like when he talks about problems?
• Does he dwell on the problem itself, or does he shift to brainstorming solutions?
• Does he run toward problems or away from them?
Why Should a Leader Love Problems?
For starters, solving problems is a leader’s primary function.
If you don’t see challenges as a norm—or better yet, embrace them—your perspective will remain limited.
Problems are a necessity. How else can you grow or scale?
It’s not about being a hero or swooping in for a last-minute save. Problems provide clarity. They help you prioritize, identify gaps, and make an impact on your team.
What does life look like for a leader without problems? Relaxing, maybe, but only briefly. Then, you’re left with two outcomes:
1. Ignoring the reality in front of you.
2. Leading stagnant, neutral teams.
The Right Mindset Is Key
Of course, having the right mindset doesn’t mean much if you can’t actually solve the problems.
Execution matters.
But when you shift how you view challenges, you give yourself the best chance to move through the hoops and hurdles.
Guide: How to Embrace Problems as a Leader
Here’s a step-by-step guide to help you shift your mindset and turn challenges into opportunities for growth:
1. Reframe How You Talk About Problems
Action:
The next time a problem arises, reframe your language. Instead of saying, “This is a mess,” say, “Here’s an opportunity to improve our process.”
Write down three potential positive outcomes of solving the problem. This keeps your focus solution-oriented.
2. Identify the Root Cause
Action:
Use the 5 Whys Method: Ask “Why?” repeatedly (five times or until you get to the root cause).
For example, if sales are down:
Why? Leads aren’t converting.
Why? Demos aren’t persuasive.
Why? Reps lack training on objections.
3. Prioritize Problems Effectively
Action:
Use the Eisenhower Matrix to sort problems by urgency and importance:
Urgent + Important: Solve now.
Important but Not Urgent: Schedule for later.
Not Important but Urgent: Delegate.
Not Important or Urgent: Discard.
Focus only on the top-right quadrant (Important + Urgent).
4. Create a Problem-Solving Process
Action:
Use this quick 4-step framework:
Define: Clearly articulate the problem in one sentence.
Brainstorm: List 3-5 potential solutions.
Assign: Decide who will take action and set a timeline.
Follow-Up: Evaluate results and refine if needed.
5. Build a "Problem Radar"
Action:
Schedule weekly check-ins with your team to proactively identify issues before they escalate.
Ask your team:
What roadblocks are you facing?
What’s slowing us down?
What can I help solve this week?
6. Document Lessons Learned
Action:
After resolving an issue, document what went wrong, how it was fixed, and the outcomes.
Use a tool like Notion or ClickUp to maintain a "Problem Playbook" for future reference.
7. Strengthen Your Team’s Problem-Solving Skills
Action:
Conduct a "Problem-Solving Workshop" with your team.
Present a mock problem.
Divide the team into groups to brainstorm solutions.
Discuss their approaches and best practices.
8. Practice Stress Management
Action:
To stay calm under pressure, adopt one stress management habit:
Morning meditation (try Headspace).
Journaling about challenges and wins daily.
Taking a 5-minute walk after a tough meeting.
9. Celebrate Problem-Solving Wins
Action:
Acknowledge individuals or teams who solve problems effectively.
Send a quick email, give a shoutout in a meeting, or provide a small reward to reinforce positive behavior.
10. Use This Reflection Prompt
Action:
At the end of each week, ask yourself:
What was the biggest problem I faced?
How did I handle it?
What did I learn that will help me next time?
This guide is designed to not only shift your mindset but give you actionable steps to approach problems with confidence and clarity. Start small, implement one or two steps today, and build from there!
