A Readiness Quiz & Guide To Determine If Leadership Coaching Would Work For You

readiness quiz to determine if career coaching would work for you

Here’s a typical conversation I have at parties:

Person: “So what do you do?”
Me: “I’m an executive leadership coach.”
Person:“Hmm, so what do you do exactly?”
Me: “Well I’m really great at helping people improve their interpersonal interactions and relationships at work. I tend to work with corporate and business leaders who are very smart and great at their jobs but are having trouble working with some people around them.”
Person: “Oh you mean for people who aren’t natural managers?”
Me: “Sure, sometimes. But also there are leaders who feel their team isn’t as effective or high-performing as they’d like, or people who find themselves in conflict with someone senior in their organization and it’s getting in the way of their work. My clients end up feeling a lot happier and successful in their workplace dynamics.”
Person: “Oh wow, could you talk to my husband/best friend/daughter (or fill in the blank)? They could really use your help.”

This conversation always makes me smile. And then I explain to them that in my experience, it doesn’t work for someone else to see the need for a coach for their loved ones. That individual needs to see it and want it for themselves.

Having enough of these conversations has inspired me to come up with my personal top 7 ways that you know that leadership coaching is a great fit for you RIGHT NOW – not in some imagined future.


Read the following 7 ways to know if you’re ready for leadership coaching and give yourself 1 point for every criterion that you meet.

7 Ways To Know You Are Ready To Hire An Executive Leadership Coach:

1) You Have A Leadership Challenge At Work Currently And Solving It Is A HIGH Priority For You

Let’s be honest here – almost everyone has some problem at work. I have met few (honest) people who would claim that there’s nothing they would want to change at work.

But if you’re willing to invest your, or your company’s, limited resources of time, energy and money on working with a leadership coach, you can’t just be planning to tackle a B-level problem. To make your time with a coach life changing, you need to have a big, hairy challenge:

• The kind that frustrates you on a daily basis at work.
• The kind that sometimes keeps you up at night, or if you wake up, keeps you awake trying to think of new solutions that might “work” and “fix it.”
• Perhaps you’ve even contemplated moving positions, departments or companies just to have it go away.
• This is a challenge that is ultimately limiting your current happiness, opportunities, and/or overall potential.

Although sometimes you can go weeks, months (I’ve even had some clients go years), before you recognize it’s time to devote meaningful energy towards overcoming this challenge. Once you recognize that this is a true priority in your work life, you’ll be much more open to and appreciative of the help of a talented leadership coach.

I had one C-Suite client who was finding herself in conflict with another member of the senior leadership team. After coping for more than 6 months with their deteriorating relationship, she finally made the decision to hire a coach. Within months of beginning our work together, she had completely shifted their dynamic to one where they could work productively together and she no longer dreaded any interactions they might have.

2) You Believe That Things Can Improve and Get Better – You’re Open To New Possibilities

You’ve met that person. This is the person who is grumpy and believes things will never get better because life is hard and a struggle. You’re not that person. But here’s the catch, sometimes there are parts of you that believe that work wouldn’t be called work if it was easy and fun; that part of work is dealing with people who frustrate you and if it isn’t Jack who’s on your team and passive aggressive, then it will be Donna who never listens to your opinions or takes your ideas seriously.

If some part of you is nursing the idea that work is just a series of frustrations, then there’s no incentive for you to invest in making work better.

To really benefit from leadership coaching, you need to have at least a small conscious part of you that says, “I know that things can be much better. And I want to make that happen for myself. I’m sick of feeling thwarted and tired. I’m ready to for an upward spiral of positive change and feeling more empowered.”

3) You’re Ready To Try Something Other Than “Working Harder At It”

The number one reason people tell me that they’ve decided not to hire me as a coach at this time, is that “I just want to work a little harder at it myself for a few months and see what happens.” Inevitably when I end up talking to them a few months later, they are still finding themselves at exactly the same point except more frustrated now because it’s been going on longer and sometimes things have even gotten worse.

What I’m responding now when I hear that is, “how exactly are you going to try harder and what are you going to be doing differently?” The truth is, many people can’t answer.

Sometimes it’s hard to face a reality where you must admit that your best efforts aren’t enough, and they are not yielding you impressive results. It can feel like admitting you’re not good enough.

That’s not true!

All you need to admit is that you’ve run out of great new ideas and your best efforts now include bringing in a leadership coach to widen your perspective and help you develop new skills that perhaps you haven’t needed until now.

One director I worked with initially believed that even though he felt overwhelmed and like he was “drowning,” it was a personal failing to have to hire a coach. What he realized soon after we began our work together was that burying his head in more work didn’t solve his problems. What he benefited more from was a fresh view and wider perspective on his situation. From this new vantage point, he could see how working harder had cut him off from the relationships he most needed to help him turn sales around.

Asking for support is not giving up, it’s being even more resourceful and seeking out new ideas from someone who has seen many different types of challenging situation and can offer many different solutions.

4) You’re Open To Experimentation

Let me be honest here. I don’t know the solution to every situation. And often times, the solution is not just one big step, it’s many small course corrections that end up yielding much better results for my client.

That means that if you’ve decided to open up to a leadership coach and ask for help, part of that help will mean you being willing to try new behaviors. Some new behaviors might seem simple and make a lot of sense to you, but feel challenging to implement in reality. Other behaviors might seem less relevant and not directly tackling your issue – but there’s always a reason behind my requests.

Often times I find that my clients can experiment more easily in a personal realm than a work realm. In that case I’ll often have them practice new skills away from work and then only, once they feel more confident and practiced, ask them to start implementing that behavior at work.

There’s a horrible saying that “there’s many ways to skin a cat.” Similarly, there are many ways to upping your leadership game, and if you’re willing to play and experiment, we’ll find the way that works best for your learning style and temperament.

5) You are Completely Committed To Big Results

Of course the first commitment to coaching is showing up. But even beyond that, we’ll make many agreements in our work together. Ways that you will promise me to practice and experiment so you can see meaningful change. If I can’t count on you to honor those promises, it will be much harder for you to get feedback on your efforts, learn from them, and improve your skills even more.

Does that mean you’ll accomplish everything you say you will? No of course not! Life will intervene. You’ll get slammed at work or come down with the flu. I will understand . . . really! But unless you’re truly dedicated to your results, you won’t do the real work of keeping the ball moving forward between sessions – and that ultimately gets the transformation.

I’ve worked with many clients and the ones that see the biggest improvements – those are the ones who take risks and try new behaviors between sessions when they say they will, even when it feels awkward, “weird,” or not easy. Because they know it’s in service of their much larger goal of success, and they’re committed to making that happen.

6) You Can Open Up To Another Person

You’re not perfect. I know that. I’m not perfect either. In fact, I’m quite perfectly imperfect.

This means I don’t expect you to be a model human being, have no baggage from your past, or be 100% consistent. We humans can be pretty confusing to figure out, and sometimes, we don’t even understand our own behavior.

If you’re devoted to reaching the next level in your leadership evolution, you must be willing to cop to some of your less impressive moments and be honest about what you believe you’re capable of.

Your goal is not to impress me. It’s to open up to me about what’s really happening so we can bring it into the light of day, examine it, and come up with practical solutions that don’t overwhelm you.

If you’re intent on keeping your thoughts and feelings to yourself or cultivating a certain image, you’ll miss out on the full benefits of executive coaching.

7) You Have A Sense Of Humor

Ok, ok. It’s true – you don’t have to have a sense of humor to benefit from working with an executive leadership coach.

But my clients do.

Let’s face it. Some parts of life just feel hard. Being able to laugh about it makes it a lot more fun on a day-to-day basis.

I love to express my humor with my clients and I love it when my clients bring their humor into the mix. It makes our sessions fun, it makes the learning feel a lot more enjoyable, and most importantly, it makes you willing to return again and again for further learning, growth, and laughter.

So while I believe in “serious” development, I know the journey can be light-hearted.


Remember to give yourself 1 point for each readiness benchmark that describes you/your situation.


0-2: You might have some challenges at work right now, but it doesn’t seem like leadership coaching is the right solution for you at this point. It’s always an option for the future if it feels as if more support and strategies would be helpful.

3-4: You’re on the fence about whether working with a coach is what would truly help right now. If you’re talking with a coach, mention your concerns and see if there are true hold-backs for you or just some concerns you need to explore further before you feel ready to proceed.

5-7: Congratulations, you’re ready! You seem like a great candidate who would benefit greatly from working with a high-quality executive coach. I’d be happy to talk to you further and see if we are a good fit together or if I have a referral/resource that might be a better match.

To schedule a time to talk just go to https://www.incitetoleadership.com/contact/ and fill out the form or email my assistant: leadership at successreboot.com.

Jo Ilfeld, PhD

An executive leadership coach, Jo helps C-suite leaders, executives, and high-potential managers develop the flexibility, skill, and frame of mind to meet the challenges of the next five, ten, twenty years…. and beyond. She works with individuals, teams and organizations on four core areas of leadership development. Check out Jo's bio page for more information.

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