Successful-but something still feels off?
- Halle Simpson
- 5 days ago
- 2 min read
One of the most common questions I hear from business owners and executives is this: “How do I know if I need a coach?”
Not which coach. Not how much coaching costs. Just… how to know if coaching is even the right next step. Here’s a simple way to think it through.
What challenge are you facing right now?
Most people who benefit from working with a business or executive coach aren’t in crisis. They’re successful, capable, and still feel stuck, stretched thin, burned out, or unclear.
Common challenges include:
Decision fatigue
Leadership or team issues
Feeling overwhelmed despite success
Growth that feels harder than it should
If you’re struggling to clearly define the challenge, that alone is a sign coaching could help.
What have you already tried?
Most leaders have already done a lot before reaching out:
Books, podcasts, courses
Talking it through with trusted peers
Trying to “push through” on their own
If the issue keeps resurfacing despite your effort, it’s often not a strategy problem. It’s a perspective, pattern, or blind spot problem—exactly where coaching works best.
How have you handled similar challenges in the past?
High performers are resourceful. You’ve likely relied on intelligence, grit, and self-reliance for years. But growth often requires new tools. What worked before may not work at your current level of leadership or responsibility. A coach helps you think differently—not work harder.
How long has this been going on?
If something has lingered for months (or years), it’s no longer situational. It’s a pattern. Coaching helps interrupt patterns before they become burnout, disengagement, or costly mistakes.
Is this a symptom of something deeper?
Burnout, lack of focus, people challenges, and constant urgency are usually symptoms, not root causes. A good leadership coach helps you uncover what’s underneath and address it intentionally…at the source.
Bottom line, you’re not “broken” if you seek out the aid of a coach; however, don't wait until you feel that way! You just need to sense that where you are isn’t where you want to stay.
If you’re pondering this question yourself, I offer complimentary coaching conversations for space to think, gain clarity, and explore next steps.
Book a time when you're ready.
Sending joy and happiness to you in this holiday season!
Halle
PS:
1. For daily support and tidbits follow me over on Insta!
2. Time for a new journal? Pick up a new copy of my Know Thyself Journal for daily support towards your most important intentions for the next 90 days.
3. Are you into individual assessments? Here is a link to take a free Core Values Assessment (CVI). It only takes 10 minutes and measures your innate, unchanging nature. Take it yourself and feel free to forward to a friend, too.
