The Five Things That Get in Leaders’ Ways

What It Covers

Dave Stachowiak from Coaching for Leaders identifies five recurring obstacles that prevent leaders from improving: not asking for help, assuming knowledge drives behavior, setting tactical bars too high, expecting progress to feel good, and failing to notice personal growth over time.

Key Questions Answered

• •Asking for Help: Leaders avoid seeking help primarily because it feels unsafe, not because it actually is. The fix is finding one person outside your organization or industry who holds no political stake in your situation. This person can give objective guidance without judgment, and the act of asking regularly builds the habit of openness to growth.
• •Knowledge vs. Behavior: Knowing a leadership framework and applying it in a real one-on-one meeting are entirely different skills, similar to passing a written driving exam versus actually driving. When stuck in a knowledge loop, skip the next book or podcast and spend that same time implementing one concept already learned but not yet practiced with your team.
• •Tactical Bar Setting: Set vision and outcome goals high, but start tactics at the smallest possible unit — five minutes or one action per day. Leaders who aim to recognize every employee in every conversation often quit after missing two or three people, labeling themselves failures despite a 70% success rate on day one.
• •Feeling Worse as Progress Signal: When a leader gains more visibility or influence, they often uncover problems previously hidden from them. This feels like regression but signals forward movement. Write down in advance the specific frictions likely to arise from a new goal, then use an objective third party to distinguish healthy tension from genuinely harmful situations.
• •Tracking Improvement: Leaders are typically the last to notice their own growth, just as parents stop seeing daily height changes in their children while grandparents notice immediately after months apart. Record current skill levels and target outcomes at the start of any development effort, then review progress every 60 days to maintain motivation and course-correct accurately.