How do you know when it’s time to hire an executive coach? Listen to yourself and your thoughts. You’re probably saying things that clearly show you’re ready to level up but could use the guidance of an expert to get you there faster and more effectively.
After working one-on-one with more than 1,000 professionals, I’ve developed a good ear (you could say, a sixth sense) for phrases that signal it’s time for someone to level up and start exploring executive coaching.
Below are 10 phrases to pay attention to. If you hear yourself (or your team) saying any of them, it’s a strong indicator that it’s time to work with an executive coach.
10 Phrases That Reveal You’re Ready To Level Up With Executive Coaching
1. “I’m starting a new job.”
Starting a new role, whether with a new company or within your current organization, is scary—and that fear is one of the clearest signals that it’s the right time to invest in executive coaching.
And even if you’ve been promoted internally, you’ll still be faced with new expectations and responsibilities, team dynamics, and visibility needs that will require you to level up, which makes executive coaching just as important.
An executive coach can help you with the mental and confidence aspects of leveling up. They can also help you develop a comprehensive onboarding plan and a personalized 30-60-90-day plan so that you’re set up for success from day one and make a lasting impression.
Case study: One tech executive landed his first Chief Product Officer role. We created a 90-day plan that showcased his readiness to lead product-driven growth while fostering collaboration from day one.
2. “I feel like an imposter at work.”
Feeling like a fraud, fearing you’ll be “found out,” or attributing your success to luck may signal imposter syndrome. It can also indicate that it’s time to work with a coach to build your confidence.
Over the years, I’ve found that imposter syndrome can be incredibly sneaky, with it often telling clients that they’re not enough and that they haven’t earned their place at the table. Your imposter syndrome is lying to you!
A coach can help you implement practical strategies for quieting your inner critic, strengthening your self-esteem, and building real, lasting confidence.
Case study: A new head of HR at a fast-growing startup doubted her ability to lead on an all-male executive team. Coaching helped her gain confidence and contribute to senior executive and board meetings with ease.
3. “My communication skills are lacking.”
“Soft skills” like executive presence, conflict resolution, and storytelling become increasingly important as you climb the career ladder, yet few organizations provide adequate training in these areas to leaders.
Communication is about so much more than just talking. You must also learn to actively listen, influence, and persuade, skills that become increasingly important as you climb the ladder. If you’re like many of my clients, you were never properly taught them.
If you find your communication skills falling short, or you simply want to stay ahead of the curve, it’s worth investing in coaching to develop these critical abilities.
Case study: A senior director struggled to communicate with the C-suite. After focused coaching, he delivered updates and presentations that convinced leadership he was ready for a promotion to the VP level.
4. “My boss is sabotaging me.”
A difficult boss can make or break a work environment and may even push you toward leaving (this has definitely been the case for me at more than one company!). Before making any drastic moves, though, consider working with a coach to explore your options, as burned bridges can’t be rebuilt.
Toxic bosses are a reality in literally every line of work (ugh!), so it’s helpful to gain practical skills in how to effectively deal with them (or at least tolerate them).
A coach can help you weigh your situation objectively, uncover how you might be contributing to it unknowingly, and even role-play various scenarios to prepare for your difficult conversations. We’ve got your back!
Case study: A VP was undermined by his supervisor (CEO) in key meetings. We role-played scenarios and developed a methodical approach to responding to this lack of support, enabling him to navigate the dynamic gracefully without burning bridges.
5. “My workplace is toxic.”
It’s normal to have a bad day (or even a bad week), but a persistently toxic environment is not normal. You deserve better, and you’re not alone.
If you’re dealing with or recovering from a toxic workplace, it’s essential that you work with a trauma-informed executive coach. A trained professional can support you in evaluating your options, beginning to heal, and navigating your career forward in a healthy way.
Case study: A CHRO faced persistent negativity from her team. Trauma-informed coaching helped her set boundaries and implement executive-level culture shifts that improved team morale.
6. “I struggle with delegation.”
As you grow in your career, you must master the art of delegation. If you often find it easier to do tasks yourself or feel that no one can match your standards (I admit that I used to be this way!), it might be time to partner with a coach.
Coaching really helps you set expectations, build scalable systems, and empower your team without relying on micromanagement.
Beyond delegation and learning to empower your team, an executive coach can help you strengthen your other leadership skills, like giving and receiving feedback, managing conflict, and building team resilience.
Case study: A VP handled all projects personally, resulting in severe burnout. Coaching helped him establish scalable processes, empower his team, and reclaim focus on his most strategic priorities.
7. “I want to improve my thought leadership.”
Many leaders want to improve their thought leadership through articles, podcasts, and speaking engagements, but they don’t dedicate the time, energy, and space to do so consistently.
Thought leadership is about so much more than just publishing content, though. As an executive, you want the right people to see your message. For instance, if you’re a CTO, having a handful of CEOs, board members, or funders see your work is more impactful than hundreds of random followers.
A coach can help you clarify your intention and strategy, develop your branding and messaging, and hold you accountable to your thought leadership goals.
Case study: A marketing director wanted visibility in the tech community. Coaching guided her to define a messaging strategy and consistently publish new insights, resulting in invitations to appear on podcasts and at industry conferences.
8. “I’m considering a new career path.”
Changing careers is a common topic covered in coaching. However, it becomes more nuanced when you’re later in your career, since there’s so much more at stake (salary, mortgage, kids’ college tuition, you name it), so you’ll want to work with an executive coach to navigate the process.
I tell my clients to think of me as being like a GPS for their career, one who helps them navigate complex roads with intention and foresight.
This trained coach can help you clarify your priorities, explore options, and chart a detailed path forward, taking into consideration the unique challenges of an executive job search.
Case study: A seasoned entrepreneur explored shifting in-house later in his career. We mapped priorities, options, and risks, enabling him to pivot confidently into a corporate role aligned with his career goals.
[Read: Executive Career Coaching: Why Career Coaching For Executives Looks Different]
9. “I can’t disconnect from work.”
Struggling to unplug from work signals that you need to reevaluate your relationship with time. Period.
Working as an executive doesn’t mean that you can’t have some semblance of balance in your life. It’s still possible!
A coach can help you set and reinforce boundaries, improve work-life integration, or even explore whether new roles or career paths might better support your goals.
Case study: An executive was working 80+ hours a week and was utterly exhausted. Coaching helped him set and maintain healthier boundaries, delegate effectively, and reclaim family time without compromising his impact at work.
10. “I’m feeling stuck.”
Last but certainly not least, one of the most powerful reasons to partner with an executive coach is when you’re feeling stuck. Whether you’re feeling stuck professionally, personally, or something in between, coaching is a space where you can wrestle with uncertainty.
I believe this is where the real magic and fun of coaching comes in—helping you reframe your thinking, explore options, and develop a clear path forward when you feel utterly stuck.
Case study: A senior engineering leader was unsure of her next career move. Together, we explored goals, clarified requirements, and charted a path forward that led to a Fortune 50 tech role with a 3X salary, increased impact, and better work-life balance.
Should I Work With An Executive Coach?
Unless you’re being required to do so as part of a performance improvement plan (PIP), working with an executive coach is ultimately your choice.
That said, coaching can have a major, transformative impact on your career and life. Clients often report greater clarity, increased confidence, improved work-life balance, and the list goes on. One client even said, “Kyle’s coaching completely changed the trajectory of my career.”
How Often Do You Meet With An Executive Coach?
Frequency can vary dramatically depending on the coach, client, and engagement. Some meet as frequently as weekly, while others meet monthly or even bimonthly.
Personally, I tend to meet with clients every two to four weeks, as it allows them enough time to absorb learnings and complete “homework,” but not so much time that the majority of our sessions are spent catching up on progress.
What Do You Discuss With An Executive Coach?
The topics you can discuss are virtually limitless. Common executive coaching topics include career strategy, communication, collaboration, conflict management, work-life integration, and personal growth.
You can bring challenges, dilemmas, setbacks, reflections, wins, or no agenda at all. Coaching is your confidential sounding board for exploring what feels impossible.
Some coaches prefer to stick to more professional topics, while others (raise hand) understand and appreciate clients bringing their whole selves to sessions.
Read: [How To Know Whether You Need A Coach Or A Therapist]
Final Thoughts On Hiring An Executive Coach
Finding the right executive coach for your goals is like baking a cake: it’s a process you don’t want to rush. You want to be clear on your purpose for working with a coach, speak with several candidates, and scrutinize their qualifications, process, and fit.
Be sure to check out my Forbes article on how to choose the best executive coach for your needs. TL;DR:
- Gain an understanding of their niche and area of expertise. You deserve a coach who understands your industry and has experience working with a leader of your caliber. This is particularly important if you work in tech, as the challenges are so specific to this industry, and strategies from those without an intimate understanding will most often fall flat.
- Assess their qualifications. Because the coaching industry is unregulated, you must scrutinize a coach’s education, credentials, and advanced training to ensure they’re truly qualified. Look beyond generic certificates and confirm that they’ve been trained to support senior leaders like you.
- Review their thought leadership. Look beyond social media, which has made it easier than ever for coaches to exaggerate (or even fake) their expertise. Examine their website, articles, and client testimonials to ensure they’re consistent across all platforms.
- Speak with several coaches. Even if you’re referred to a specific coach (the vast majority of my business comes from word of mouth), I encourage you to schedule discovery calls with multiple service providers before making an investment. You’ll want to ask about their background, qualifications, and process and verify testimonials from former executive coaching clients who are similar to you.
On a final note, if one (or more) of the phrases in this article resonated with you, and you’d like to explore whether my executive coaching program is right for you, I invite you to schedule a consultation. I’m here for you! You’ve got this!
