When is the Best Time to Invest in Leadership Coaching?

Talent Collective
Talent Collective
Published in
4 min readAug 23, 2022

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By Crystal Henrickson, certified Leadership and Career Coach

Some leaders and managers are missing out on the benefits of having a coach because they’re holding out for what they believe is the perfect moment to start. Waiting until you’re not so busy, busier, well rested, or starting a new role can easily mean you end up not starting at all. While there’s no such thing as the perfect time to start leadership coaching, here are some of the near perfect times to get going:

When you’re worrying

Are you having trouble quieting your mind so you can fall asleep at night? Or maybe you catch yourself in a negative thought spiral during the day, churning through your work worries one by one. Carrying work worries through your day and night can impact your overall mental and physical health. If you find yourself ruminating rather than problem-solving, it might be time to connect with a leadership coach to begin building solutions.

When it’s lonely at the top

Having a friend or colleague that you can share work struggles with can be useful, but they may not have a full appreciation of the challenges you’re facing or an understanding of how to support you effectively. They may also have a stake in the results of the choices you make, which can (unconsciously or not) bias the advice they provide. You may even find yourself without someone to confide in, without an outlet that’s safe with someone who is on your side and really partners with you on what you’re dealing with. A leadership coach is an informed source of support who is there just for you, to bring out your unique brilliance and shape strategies for your specific situation. They’re your partner in improving your professional life, focused on your success and happiness, and can be a powerful tool in your career progression.

When you’re stuck

If you’re consistently getting the same underwhelming results for your career, your team, or your company, it may be time to invite a new point of view into the conversation. Sometimes just looking at an issue from a new angle can unlock insight and innovative ideas that break through a blocker. An experienced career coach who has worked with a variety of leaders will have seen and heard just about every scenario out there and can apply their knowledge to collaboratively unpack a seemingly impossible situation.

When you’re short on time

It may seem counterintuitive to add something to your plate when it’s already overflowing, but that is actually the right time! If everything is happening at once and you’re moving quickly, that’s likely when you need thought partnership the most. Coaching can actually help you get time and energy back into your life by improving your support structure, redesigning your routine and building capacity. Even just one hour of coaching a month can help you work through complex professional issues, creating a positive difference in your workload and outlook.

Being an effective leader doesn’t mean you have the answer for every situation. Being resourceful and adaptable are far more effective strategies to help you design solutions for your challenges. As you ascend as a leader, the complexity will likely increase and require an ongoing process of learning and experimentation. Having a trained thought partner to collaborate with through the complexities will accelerate your ability to handle them and continue levelling up your leadership. Reach out to share your challenges and explore coaching with me during a free 30 minute discovery session.

Crystal Henrickson is a certified Leadership and Career Coach, Employee Experience Strategist and co-founder of Talent Collective. Certified as a Co-Active® and Professional Coach, Leadership Circle Profile Practitioner™ and Mentor Coach, Crystal focuses on the deep development of current and aspiring executive and director-level leaders in fast-paced tech organizations. Specializing in the toughest of topics, Crystal understands the “whole life” of a leader, coaching them to excellence in their interconnected personal and professional lives. She has led changemaking people and culture initiatives at 30+ technology-driven companies, most notably driving the market expansion for Yelp into Canada.

Connect with her on LinkedIn!

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